Sex Show

When I was a young man, I used to enjoy going to strip clubs. I wouldn’t get the chance to go very often, usually because a friend was getting married and there was some sort of stag party to celebrate. During a few business trips overseas, I went to sex clubs and watched shows. Those shows usually catered to the sexual preferences of heterosexual males. There was often an obligatory lesbian sex, although to me the performances looked simulated. I once saw penetrative sex between two women, one of whom wore a strap-on. Another time I watched a man fuck a woman doggie style.  I have also seen BDSM shows where the women were placed in bondage kinbaku-style. I have never seen a femdom-themed performance, nor have I even heard of. Such a show. Flash forward nearly twenty years and I found myself forced to perform as a submissive in a performance for women. That performance changed me forever.

I was not always submissive to my girlfriend Anne. In fact, when we met five years ago, I considered myself dominant. Although I enjoyed the BDSM lifestyle, I participated “just in the bedroom”. When Anne and I first started having sex, I would occasionally spank her, just for fun. Although I first I thought she enjoyed light BDSM, she sat me down after a few sessions and told me that she would prefer to do the spanking. I told her had not been spanked since I was a little kid, when my mother would occasionally punish me corporally. She responded, “I can tell, Michael. You could use a good spanking.” While I was curious about Anne’s kink, I had to leave for work.

As usual, I was the first home from work. I went in the kitchen, made myself a snack to hold me over until dinner, and a grabbed a beer from the fridge. I was watching the news on the television when I heard Anne come home from work. She walked into the living room a few minutes later. Standing over me, she said “You left a mess in the kitchen.” I apologized and told her I’d clean it up soon. Telling me she did not like to come home to a mess, I could tell she was serious about her disapproval. “I would like you to do something for me.”, she said. I offered, “Clean the kitchen?” She replied, “No, take your clothes off.” I thought things had taken a strange turn. First, she was complaining about my behavior and now she seemed to want to have sex. Horny, I quickly stripped off my clothes, letting them drop to the floor in a trail as I followed Anne into the bedroom. Once in the bedroom, Anne asked me to lay on the bed. “Oh boy, I love cowgirl style”, I said. Laying on my back, Anne asked me to roll over. “Okay, but why?” In a stern voice, Anne insisted I comply with her commands. I had never heard her so dominant. I rolled over submissively. Standing over me, Anne suggested, “You needed an attitude adjustment.” She patted my butt with her hand as she spoke. “You want to spank me?”, I asked. “No, I want to cane you.” I was shocked as she walked to the closet and produced a bamboo rod. “Do you agree that you should be punished for your behavior, Michael?” She was serious. I replied with some ambiguity, “I suppose.” Not satisfied with my answer, she replied, “I expect clarity from you.” My second reply to her question was unambiguous, “Yes, I should be punished.” While tapping my butt with the cane, she clarified, “I am going to strike you ten times for leaving a mess in the kitchen.” “I want you to count off the blows.” I nodded in the affirmative, but unsatisfied with my non-verbal response, she commanded, “Use your words.” “Yes, I will count.” Still not satisfied, she made it clear that I needed to show more respect and wanted to be called “Ma’am.” “Yes, Ma’am”, I replied, wondering what I was getting myself into. Raising the cane she struck me hard. I bucked. Once I had recovered, I responded, “One, Ma’am.” She acknowledged that I was learning. As she delivered nine more blow, I counted them off obediently. When finished, she asked if I had anything to say. I said, “No, Ma’am.” She responded that I should thank her for correcting me. I said, “Thank you for correcting me, Ma’am.” “Good, you can clean the kitchen now. I got up, rubbed my raw ass cheeks, and walked towards the kitchen. Passing my clothes on the floor, I picked them up and started putting them on. Anne made it clear that I had lost clothing privileges for leaving my clothes on the floor. “In fact, in general when you do housework, I would like you to be nude.” A sea change had occurred in our relationship. I could tell here was no walking this back.

I was nearly done cleaning the kitchen when Anne came in to “inspect” my work. “You’ve cleaned up the mess you made today, but the kitchen is not clean. She pointed at dishes that needed to be washed and trash that needed to be taken out. After putting the dishes in the dishwasher, I asked if I could put something on before taking out the trash. Anne said no. I flashed her a stupid look and she threatened to get her cane. The trash can was on the side of the house, outside the fence and within clear view of the road and the next-door neighbors. It was getting dark, so I felt I could take the trash out stealthily. Carrying the trash, I opened the side gate and under the cloak of near darkness I moved carefully towards the trash cans. Suddenly, the outdoor lights came on. Anne was exposing me. I quickly put the trash bag in the receptacle and dashed back inside. Anne offered no apology as she switched off the outdoor lights. This would not be the last time Anne would discipline me, nor would it be the last time she would embarrass me.

Over the intervening years, our relationship became increasingly steeped in BDSM.  Anne had new expectations, both in the bedroom and out. Away from the house, our relationship probably appeared largely on even footing, although I am sure our friends noticed how polite and apparently doting I behaved when it came to Anne. At home, I was often expected to be nude. I had many chores. I was expected to keep the house clean. I kept Anne’s anus clean too. One day I came home from work and there was a present waiting for me, a small black box with a black ribbon. I opened the card tucked under the ribbon, it read, “It would please me if you were wearing this when I get home.” The box contained a chastity device. Anne and I had talked about such devices before, but I had not actually agreed to wear one. Curious, I tried the steel cage on. It fit. I closed the padlock, thereby consenting to genital bondage. It would be the last time I would be able to touch my penis.

I was sitting on the couch when Anne came home. I was naked, as she expected. Anne walked to the couch, took my hand, and helped me to my feet. She smiled and simply said, “Good.” “When will I be released from chastity?”, I asked fearful of the answer. “You won’t be released”, she replied to dead silence. “There is no key.” “But how will I ejaculate? How will we have sex?” We had been fucking less as our sexual relationship became more one-sided. While we fucked once a month or so, whenever she got the urge, I would perform cunnilingus on her nearly every day, sometimes more than once a day. She allowed me to masturbate, which was my main form of release. She explained, “We need to talk about some new rituals.” What more did she want from me? “You will be milked periodically. You will learn to release your semen through stimulation of your prostrate.” “What does that even mean”, as asked, panic in my voice. Anne had me wear anal plugs periodically, usually as a form of punishment, but she had never otherwise expressed an interest in assplay … at lease with my ass.

Our routine was pretty much normal for the following few days. I took care of my responsibilities, both domestic and sexual. As a week approached since the cage was put on, Anne said she wanted to have weekly date nights. We used to have date nights earlier in our relationship, dinner and a movie, or something like that. I agreed that date nights would be nice. She said every Saturday evening at 8:00. I thought it strange that she was so specific about the time. Saturday evening seemed like a strange time for a date, but I did not ask any more questions. On Saturday morning I asked Anne what she wanted to do for our date. She opened a drawer in her dresser and removed a strap-on. I did not know she even had a strap-on. She didn’t elaborate. The strap-on sat on the bed for the remainder of the day. Early in the evening, Anne explained there were certain thing I needed to do to get ready for our date. I would need an enema and I would need to bathe. I would also need to dress for our date. The strap-on was still on display on the bed, so I understood the significance of an enema. I asked Anne what I should wear for our date, and she said she would lay out some clothes for me to wear.

At 7:00, I was just finishing cleaning up the kitchen after dinner, nude of course, when Anne came in. “It’s time for you to get ready. I have laid out some clothes for you to wear. I want you to look pretty for our date.” I thought it was a strange choice of words, “pretty”, until I went into the bedroom and found a pair of white bikini panties and a pink nightgown laid out next to the strap-on. Anne was standing behind me and she spoke, “You’re not really a man anymore, are you?” I turned to face her and she was tapping her palm with the cane. I offered no resistance. I went into the bathroom to get cleaned up. Stepping out of the bathroom into the bedroom, I picked up the panties. I had not noticed, but they were sheer and thongs. I put the panties on. They felt strangely comfortable, but they barely covered my cage. Coverage was a moot point though as the panties were nearly transparent. I slipped the pink, lacey baby doll nightgown over my head. I have a long torso. The nightgown barely covered the panties. I believe it was called a babydoll nightie. I looked at myself in the full-length dressing mirror and was horrified that I was being feminized. 

Anne walked in precisely at 8:00. I was still standing in front of the mirror. From behind me, I heard Anne simply state I looked lovely. “Lovely.” I turned to face her and she said “I would like you to assume a position for me by 8:00 each Saturday so I know you are ready for our date. I asked what position and she simply responded, “Doggie. You remember the doggie position, don’t you, Michael? I mean from when you used to be a man.” I blushed. “Yes, Ma’am” “It wouldn’t be a date without sex, right?”, she queried. “No, Ma’am”, I responded, knowing what came next. I assumed the position in the middle of the bed and Anne corrected me. “I would like you to back up, so your knees are on the edge of the bed.” As I moved into position, Anne nodded approval. “This is where I want you to be at 8:00 every Saturday.” “Yes, Ma’am.” Anne stepped behind me. She was still fully dressed in a blouse and yoga pants. I could hear her put on the strap-on. I could hear the snap of a rubber glove. She pulled down my panties and flipped the nightgown over my back. Then, for the first time in our relationship, she penetrated my anus with her finger. I felt the rubber glove. It had been lubricated. After finger fucking me a few minutes I felt her slip in a second finger. She began twisting the two fingers back and forth, loosening my rectum. The third finger did not go in as easily as the first two and the fourth had to be forced in over my vocal objections of pain. Although not that day, eventually she would fit her entire fist in me. She worked on loosening my rectum for about twenty minutes before I heard the rubber glove being removed. Pushing first the tip of her plastic phallus in me. Eventually, the entire eight inches were in me. She left her cock sit still for a minute or two. During that time she verbally humiliated me. “I love that you dressed for me. The nightie makes you look so sexy. I wanted to fuck your pussy the first moment I saw you in it.” She reached down to the cage and touched the tip. There was pre-ejaculate. “I can tell you are excited to be fucked sweetie.” She began to thrust in and out. “Head down and ass up, bitch.” I complied and she fucked me like a whore. After about ten minutes I felt a new sensation. I was cumming, but without an orgasm. “There you go you, cum for me. Get all that nasty jizz out.” She had placed a bowl beneath the cage, and she continued to fuck me until no more semen dripped from my cage. Withdrawing her cock, she ordered me to kneel in front of her as she sat on the edge of the bed, still wearing the strap-on. “Yes, Ma’am.” “Pull up your panties, you slut.” “Yes, Ma’am.” 

Once kneeling submissively in front she explained, that I would have two new responsibilities after each of our dates. Handing me the bowl she said, “First, spunk offends me. I expect you to lick your bowl clean at the end of our dates.” The thought repulsed me. She pushed the bowl towards my mouth. “Do it!” There were perhaps five milliliters of fluid. It did not look like semen. It was clearer. I complied and licked the bowl clean. It was the first time I had tasted semen. “Great! Good job! Now, when I am finished fucking you, I’d like you to return the favor by giving me a blowjob.” I gave Anne a puzzled look, but she put her hands behind the back of my head and pushed my mouth towards her dildo. I resisted, but she forced it into my month. “That’s right.” I started to gag when she withdrew the cock from my mouth and ordered me to lick it clean. I was disgusted for allowing myself to be degraded like this. I could taste lube and my ass on the plastic dick. I wanted to throw up, but I did as she asked. When I was finished, she removed the strap-on and told me to put my “pretty outfit” in the laundry and get cleaned up for bed. I obeyed her. About 9:00 I noticed she had gone to bed, and I joined her. She spooned me and whispered, “I told my girlfriends I was going to fuck you today.” The was the first time I had known our sex life was mentioned to anyone else. I started trembling. “It’s already, dear. They already knew about us.” I would be several hours before I finally fell asleep.

The next morning, I was serving Anne her breakfast. I returned to the kitchen to get my breakfast and then joined her at the dining table. While I had stepped away, Anne had spread out some photographs. They were of me. I had not noticed she had taken photos the night before. There were photographs of me being feminized. There were photographs of me being pegged. There were photographs of me performing my after-sex duties. “Which ones should I share with my girlfriend?” I blurted out, “None of them.” She replied, “That was very disrespectful.” I tried to make amends. “I apologize, Ma’am. I really would prefer if you didn’t share the photographs.” It was too late. I had already offended her. She said I needed to be disciplined, now. Naked, I went to the living room and kneeled in the middle of the room with my face pressed to the floor and my ass in the air, as I had been programmed to do. Anne finished her breakfast. My knees were becoming sore waiting for her while I knelt on the wood floor. After about fifteen minutes, Anne walked past me, into the bedroom, and returned with the cane. Anne would always tell me how many before she started. “Fifteen.” I counted the blows off as I received them. When she finished delivering the punishment, she dropped a photograph on the floor next to me. “I have chosen this one.” fifteen The photograph looked down at the dildo penetrating my ass. It showed the white panties around my knees and the pink nightie hiked up my back. It did not show any faces, but I knew if she shared it with friends, everyone would know who was being fucked and who was doing the fucking. “Yes, Ma’am.”

The week went by without any further discussion of the photographs or any of the events that transpired during our date night. I laundered my panties and the nightie. At 7:00 on Saturday I began preparing for date night. By 8:00 I was clean, dressed, and in the doggie position. At 8:00 sharp, Anne walked into the room. She was already wearing the strap-on. She didn’t say anything before she started probing my anus. She loosened me more quickly that the first time and within a few minutes she was pegging me. It took longer to be milked than the first time, perhaps fifteen or twenty minutes. When she finished, she sat down on the edge of the bed. Without prompting, I kneeled in front of her, ate my semen, and cleaned Anne’s cock. Looking up at her, I said “Thank you for date night, Ma’am.” You’re welcome, sweetie. You have a pretty cunt and I enjoy fucking it.” 

The date night ritual was repeated every week for several months. The process was always the same. Ten week after our first date night, I was dutifully in position at 8:00 on Saturday when Anne walked into the bedroom. As usual, she was wearing her strap-on. “Sweetie, it’s a lovely night. Let’s fuck in the backyard.” We have a privacy fence around the backyard, so this proposal did not concern me. Anne handed me a blanket, I went outside and spread it out on the ground, and I assume the doggie position in the middle of the blanket. As I waited for Anne, I heard the neighbors who live behind us. They were having a party. Anne walked up behind me. “How does it make you feel knowing there are so many people a hundred feet away as I fuck you?” I did not have an answer. “Should I invite our neighbors and their friends over to watch?” I spun around in horror and pleaded, “No, please, Ma’am.” She smiled and replied, “Well, I suppose it would be impolite to interrupt the party.” Anne began loosening me, then she fucked me pile-driver style until she was convinced, I was drained. When finished, I licked the bowl clean and kneeled before her as she stood in front of me fucking my mouth until her cock was clean. I had become used to swallowing her cock and could take most of it down my throat. “You know, our neighbors would not have been the first people to see you getting fucked.” I looked up at her, the strap-on just a few inches from my lips. She elaborated, “My girlfriends were curious about pegging, so I sent them a video. Some of them say they want to try pegging.” I looked down at the ground in shame.

The next Friday I returned home from work. Anne was entertaining. Two of her girlfriend, Alex and Peggy, were in the living room with Anne. The three women held a glass of white wine. “Hi, Sweetie! You know Alex and Peggy.” The two women smiled and waved at me. Normally, I undress as soon as I get home, but when there are guests, Anne lets me stay dressed. Sometimes Anne likes to be left alone with her girlfriends and sometimes she likes me to serve them. “Can I get you anything ladies?” I was typically allowed to speak at Anne with less deference then in public.” Anne replied, “Sweetie, Alex and Peggy know about our lifestyle.” Understanding the nuance of what I was being told, I replied, “Yes, Ma’am. Can I get you anything, Ma’am?” Anne put down her glass of wine, stood up, and walked up to me. “Sweetie, are you properly dressed?” Knowing she was implying I should be nude, I dumbly reminded, “But we have guests, Ma’am.” What Anne said next was shocking … “Sweetie, I have told Alex and Peggy about your cage, and they would like to see it.” I pleaded, “No, please, Ma’am.” She replied, “They didn’t ask to see you disciplined, but that could be arranged.” Resigning, I simply replied “Yes, Ma’am.” And I retreated to the bedroom. I removed my clothes and stood naked in from of the full-length mirror. From the living room I heard Anne call out, “Sweetie, the girls would like to see your date night outfit too. I wanted to lock myself in the bathroom when Anne walked into the bedroom to supervise my dressing. “The girls have already seen you in your nightie.” I realized at that point that she had shared more photographs of me being pegged with her girlfriends. Reaching into my dresser drawer, Anne handed me my panties and I put them on. The nightie followed. Taking my hand, Anne led me into the living room. Her girlfriends began giggling. “Pirouette, dear.” Anne held my hand in the air, and I rotated in place. Alex offered, “You make a very pretty girl, Michael. Would you lift your nightgown for me?” Anne looked at me and motioned with a nod of her head that I should lift the nightie. Pulling it up to my chest, the women gawked at my sheer panties and the outline of the cage below it. Peggy said, “Turn around and let me see your butt.” I turned around. My ass cheeks were exposed by the thong. “You have marks on your butt, Michael.” There were bruises from a caning I had received a few days before. Anne explained the marks. The women had other questions about the process of discipline. Anne answered their questions in some detail, and even showed her girlfriends her cane. I stood at attention during the conversation. “Dear, please bring us some more wine.” “Yes, Ma’am.”

When I returned from the kitchen with three glasses of wine, the three women were sitting side-by-side on the could. “Can you give us a little striptease, Michael?”, asked Anne. I know of course she was not really giving me a choice. She asked Siri to play some striptease music, and “The Stripper” by David Rose & His Orchestra began playing on the speaker. Bwaaa na naaaaa, bwaaa na naaaaa … Bwaaa na naaaaa, BWAA NA NAAAAA Na. I was never a very good dancer, so I simply mimicked some archetypal moves: Lowering the string straps of the nightie, turning around, looking over my shoulder. The women began whistling. Alex cat called, “Show me your titties.” My back to the women, I allowed the nightie to drop to the floor. Turning around with my arms crossed over my chest to hide my “breasts”, I kicked the nightie into the air. It landed near Peggy, who picked it up and put it in her lap. Letting my arms fall to my side, Anne shouted, “It’s time to see your pussy.” Her girlfriend laughed. I turned my back to the women once more, in embarrassment, and I began tugging at the sides of the panties, pulling them partway off, then returning them to the beat of the music. Knowing there was no way out of my situation, I pulled the panties to my ankles and stepped out of them with my back to the women. Turning around, I covered my groin with my hands. The eyes of the two girlfriends were laser-focused on my crotch. Anne stared at my eyes nodding as if to prompt me. I let my hands fall to my side. Alex spung to her feet, looked at Anne, and asked, “Can I touch it?’ Peggy chimed in, “Me too.” Anne gave them permission and signaled for me to come to the couch. Alex was the first to pull on the cage. This was the first time the cage had been touched by anyone but Anne. When Alex was finished, Peggy took her turn. Their curiosity sated, Anne ordered me to continue serving them, which I did for another hour or two.

Two weeks later I was out shopping at a big box store when someone tapped me on my shoulder. It was Alex. She was with a young lady I did not recognize. “Hi, Michael. This is my friend Shelby. You know Anne told me I could share what happed at the party with our circle of friends. I told Shelby about your chastity device. She has never seen one. Would you show her?” I explained that would be inappropriate without discussing the matter with Anne, thinking that would be the end of the conversation. Alex replied, “Oh, I knew that would be the case, which is why I texted Anne. She says it is fine.” I told Alex that I would rather not. “Michael, Anne actually wants you to.” Alex then showed me the text messages on the phone. Anne had told Alex that I would likely resist and that I should know that it was an expectation that I comply with Shelby’s request. She said, “I would know what that means.” It of course meant discipline if I did not comply. “Where?”, I asked. Alex said we could go to the dressing room. Alex then said, “You know Anne wants you to treat all women with the same respect that you show her.” I replied, “Yes, Ma’am.” I walked behind the two women as they led me to the dressing room. Once inside, I stripped naked. The women stared at my cage. Shelby looked me in my eyes and said, “I hear you like to dress like a woman. Please put these on for me.” Shelby produced a basket of mostly lingerie. “We girls just love trying clothes on together in the dressing room of stores.” Shelby picked out a black bra and matching panties. Having no more respect for myself, I put the lingerie on. Struggling with the clasp of the bra, Alex help with the hooks. Pushing me into the corner of the dressing room, the women assessed their handiwork. Shelby did the grading. “Beautify and sexy, Michael. You know, Michelle might be a better name for you.” I pretended to agree. “Let’s try some more”, Alex said. This continued for several outfits when there was a knock at the door. We’d been in the dressing room too long and an employee was checking on us. Shelby scooped up the clothes and put them in the basket. I was still naked. Alex was holding my street clothes. For a moment I thought she was going to leave me in the room naked. Leaning over, she whispered in my ear, “I can see why Anne likes to fuck you when you are dressed like a sissy.” I knew at that point that there were no secrets between Anne and her girlfriend. I quickly put my clothes on, just before Shelby opened the door to the dressing room. She smiled as she handed the basket to the employee. The employee looked at me, smiled, and wished us a good day. I returned home, exhausted by the ordeal. When I walked through the front door, Anne was sitting on the couch. She greeted me, “Welcome come, Michelle.” When she called me “Michelle”, I realized she had been made completely aware of what had transpired. I took my clothes off and asked if I could take a shower. I felt dirty.

I few more weeks passed without any thing happening out of ordinary. I performed daily cunnilingus, I did my chores in the nude, I got milked on Saturdays. I began to look forward to being fucked during our weekly dates. It was a relief to have the release. Also, I began to enjoy the feeling of being penetrated. Leading up to one of our Saturday dates, Anne suggested I expand my wardrobe. She wanted to take me shopping. “I’ve heard you enjoy shopping for clothes.” This was the first and only specific reference Anne had made to the incident in the dressing room. “Let’s go back to the same store.” When we arrived, we went straight to the lingerie department. We were there only a few minutes when Shelby joined us. Anne had invited her. Shelby suggested more appropriate clothing might be had at a sex shop. Anne agreed and suggested we meet at one. The sex shop was a short distance from the big box store. Within minutes Anne and Shelby were selecting crotchless panties. Holding the panties up to me to gauge the fit, the store’s manager, a woman, smiled. Most of the panties were lacey, exposed my butt cheeks, and were crotchless, which of course meant my cage would be exposed. After picking out several pair of panties, the ladies turned to clothing for sissies. Two outfits were selected. Both had built-in padded bras. Both were short. One was a classic maid outfit. It was black with white trim. It had white frilly matching apron. The other dress had pink ruffles, was trimmed with pink lace, and it had a matching petticoat. The store did not have a dressing room. Anne asked the manager if she would mind if we tried on the dresses to make sure they fit. “Sure, no problem. You are the only shoppers, so you can change right here.” Anne looked at me, “Take off your cloths.” When I got down to my underwear, male briefs, Anne pointed at them, “You know I don’t like you wearing those. Take them off too.” I glanced at the manager. She smiled. I turned my back to her and removed the briefs. Anne looked at the manger told we would be buying the panties as she handed me a pair. I slipped on the white crotchless panties. My cage was exposed. Anne handed me the petticoat and I pulled them up to my waist. Handing me the pink dress, I slipped it over my head and Anne helped lace up the back of it. The women nodded in approval. “You look lovely, Dear”, the manager said. Anne, followed up, “Show us the panties.” I pulled up the dress and showed Anne and Shelby. Anne followed up, “Don’t be rude, show the manager.” The manager had not yet seen my chastity cage. I turned to the manager and lifted the dress. The manager giggled. “Bend over”, Shelby asked. I turned my back to her and touched my toes. The short dress lifted, exposing my ass. “Spread your legs”, Anne commanded. Shelby and Anne could see the cage between my legs. “I’d fuck that”, Shelby offered. It was clear everyone knew I was being fucked by Anne. I tried on the other dress and the garments were purchased. 

The following Saturday, Anne had laid out the pink dress, petticoat, and the white crotchless panties. Her strap-on was also on the bed. There was something different about it. It had a bigger dildo. I cleaned myself, dressed, and assumed my position. Anne walked in at 8:00. “Michelle, we’re going to do something a little different. The girls have never seen a man pegged, so we’re going to livestream our date if that’s okay with you.” She walked over to me a slapped by ass. “It’s okay with you, right?” I barely moved my head in agreement. “Use your words, Michelle. Do I need to fetch the cane?” I replied in a mooted and shaking voice, “Yes, Ma’am. You can stream our date.” Anne leaned her smart phone against a lamp on the dresser and adjusted the view. Anne created a Facetime group and started the streaming. Narrating as if performing, “Ladies, I know you have been curious about our weekly dates on Saturdays. Michelle, you know Alex, Peggy, and Shelby. I don’t believe you have met Brenda, Sandra, Susan, Elizabeth, or Donna. I mean, you know them as Michael, but you have never met them as Michelle. Ladies, Michelle prepares herself and is in this position waiting for me every Saturday at 8:00. As I have explained previously, Michelle wears a chastity device and consequently cannot have manly sex. Nasty man goo builds up each week and needs to be removed. Since he is caged, masturbation is not an option, so he is milked by stimulating his prostate. While such milking can be formed in several ways, I prefer to stimulate his prostate by fucking his pussy.” I know none of you have used a strap-on before, much less on a man, so you may find this interesting. After buckling her strap-on, Anne turned theatrically towards the camera and stroked the dildo. “We’re trying a new, larger cock tonight. I start by loosening his pussy.” Anne pulled my panties off. Unexpectedly, Anne pulled the panties over my head. My nose protruded from the slit. I could smell my musk. Anne was performing for the camera. Stepping behind me, I heard the rubber glove snap and I felt lube being squirted on my anus. Anne went to work opening me up. One to four fingers were easily and quickly accommodated. By now I had been fucked more than a year. I expected to feel the dildo next, but instead Anne kept stretching my anus. I felt her shape her hand like a duck’s head. She was trying to fist me. “Dear, the new dildo is much larger than the old one, so we need to make sure you are stretched out.” Five or ten minutes later, Anne’s fist was in my ass. She fucked me with her fist until she had inserted half her forearm. Since my back was turned to her, I did not realize Anne was wearing a new type of glove, one that went well past her elbow. Pulling her arm out of me and removing the rubber glove, the enormous dildo was stuck in me in one rapid stroke. Without pause, she rapidly thrusted in and out. I moaned and semen began to leak past my cage. The humongous dildo was at the same time painful and pleasurable. Anne grabbed my hips for purchase, and thrusted harder and faster than she had any other time that she had fucked me. I squealed like a girl as fluid continued to stream into the bowl. After perhaps twenty minutes, Anne pulled her cock out of me. She walked over to the camera, picked it up, and began to film me. First, she showed her friend my asshole, stretched out and gapped. She pulled the cage between my legs and showed the audience. Sitting down on the edge of the bed, I assumed my position at her feet. She directed the camera at my face and handed me the bowl. Ann pulled the panties off my head, I took the bowl, and I licked it clean. I had almost developed a taste to semen. Holding the camera with one hand, she used her other hand to direct my mouth towards the dildo. It was too large to swallow. My mouth was stretched just the accommodate the head of Anne’s new cock.  I had to lick the shaft of her cock to clean it. Anne would occasionally slap her cock against my cheek. “Get cleaned up.” Anne removed the strap-on and walked towards the living room with her phone, no doubt to be debriefed by her friends.

A week passed. When Saturday came around, the maid’s uniform was on the bed together with a pair of black crotchless panties. In place by 8:00, Anne came in, tapped my shoulder, and said “We are going to have a group date tonight. I need you to serve our guests.” There was a knock at the door. “Don’t be rude, answer the door, Michelle.” I went to the door. There was a half dozen women on the porch. I recognized some of them. I invited them in. As I began collecting their coats, I became conscious of my clothing, the maid’s outfit. Inviting the women to sit in the living room, Anne asked me to bring wine. I returned to distribute the wine. When everyone was served, Anne said I could return to the bedroom for our date. I took that to mean I should assume my position. I adopted the doggie position on the edge of the bed. I heard laughter from the living room. After ten or fifteen minutes, I heard the women filing into the bedroom. Most were behind me, but a few were on either side of the bed. Anne sat down next to my head, ran her hand through my hair and explained that the ladies want to learn how to peg men. “I suggested they could practice on you. That’s okay, isn’t it?” I replied, “I enjoy be fucked, Ma’am.” A stranger pulled my panties off. The women began probing my anus. I could not see who it was, but I looked between my legs and could see a strap-on. It wasn’t Anne’s strap-on. The dildo was a different color. The stranger was practically fisting me before she stopped stretching me and began pegging me. I could hear her moaning. I think she experienced an orgasm. She continued to fuck me for another five minutes or so. I was confused by what was expected of me. Sensing my confusion, Anne explained I should clean her cock. She said I could eat my semen later. I scooted off the bed and dropped to my knees. Shelby stood in front of me. She was naked except for the strap-on she was wearing. Her cock was not as large as Anne’s new one. I could deep throat Shelby’s cock. Grinning broadly, she seemed impressed at my abilities as she thrusted her cock down my throat. When I finished cleaning the dildo, I turned to resume a doggie position. I saw the rest of the women were wearing strap-on. One after another they would fuck me, and I would clean their cocks. Anne was the last person to fuck me. Her cock was twice the size of anyone else’s. At this point, after being fucked for hours, I had no problem accommodating Anne’s cock without any additional stretching. When all the women had been serviced, Anne passed me the bowl. There was more fluid than normally. I licked the bowl clean as the women looked on. Anne asked me to return to my duties serving them. I returned to the kitchen and poured glasses of wine. I felt lube drip from my pussy. As I passed a glass of wine to each woman, I looked her in the eyes and said, “Thank you for fucking me, Ma’am.” Each smiled and said, “You are welcome, Michelle.”

The week past. I had no idea what to expect. On Saturday morning during breakfast, I asked Anne of there was anything special I should do to prepare for our date, hoping to glean some insight into her plans for me. “You can prepare yourself like you usually do. Live streaming was so popular, we will stream our date every week. Then Anne revealed, “We will only have one guest tonight.” The rest of the day passed slowly. When I finished cleansing myself, I saw Anne had chosen the pink dress, the petticoat, and the crotchless white panties for me to wear. While dressing, I heard a knock at the door. Anne answered the door. I distinctly heard a male voice. When dressed, I assumed my position at the edge of the bed. I heard them come in behind me. “Michelle, assume your position on the floor.” I slid off the bed and onto my knees. Anne and her male guest sat on the bed next to me. I immediately noticed two things. First, Anne was not wearing a strap-on. Second, the guest was huge, perhaps a body builder. “Michelle, I have missed cock. I thought about releasing you from your cage so you could fuck me, but I decided that would be cruel. You have grown accustomed to your life and it would be confusing for you to be temporarily given the responsibilities of a man. This is Buck. The three of us are going to have a date, a sort of threesome. A MFF threesome. Do you know what MFF means.” “Yes, Ma’am.” The only real difference between you and me tonight is you have two holes and I have three. However, I don’t really enjoy giving blowjobs, so we really both only have two holes that can service Buck here. You will have some of the usual responsibilities, except you will clean up Buck’s cum as well as your own. Also, there are no plastic cocks tonight, but you will have an opportunity to clean a real cock. Is everything understood?” I replied confidently, ”Yes, Ma’am.” Anne continued, “My lady friends like to watch gay porn. Funny isn’t it that women enjoy watching two men fuck. I suppose that is not exactly what is going to happen here as Buck is the only man in the room. Nonetheless, you are going to be sodomized. One last thing before I turn the camera on, I expect you to show Buck respect. You are to refer to him as Sir.” “Yes, Ma’me. It is nice to meet you, Sir.” “Michelle, you can sit in the corner for the time being,” Turning on the camera, Anne greeted her virtual guest, introduced Buck and explained he was her bull, then turned the camera towards me. “Most of you have met Michelle. He is a cuckold.” It was at that moment I truly understood my new role. That evening for the first time in my life I had been cuckolded. My girlfriend was going to have sex with another man. I knew there was no use protesting, but I motioned for Anne to come to me, which she did. I asked her if she was really going to have sex with Buck. Her reply, “Buck is going to fuck me silly, just like my friends fucked you last week.”

Like the week before, Anne was getting off performing for the camera. She slowly stripped her clothes off in front of her bull, then she undressed him, finally pulling down his underwear to reveal an enormous cock. It wasn’t as large as Anne’s unhuman plastic appendage, but it was the largest real cock I had ever seen. Anne and Buck began kissing. Buck caressed her breasts. Anne stroked his cock. Hard, it looked like it 9 or 10 inches long. Anne looked at me and then told Buck, “You know, Michelle loves to deep throat.” Buck replied, “I’ve never met anyone who could swallow my whole cock.” “Let see if you can”, Anne challenged. She motioned me to my knees and Buck presented his cock. It was smaller than Anne’s cock but larger than anything I had previously had in my throat. I began suck the head of the cock. It was the first time I had touched another man’s penis, much less had one in my mouth. It was ironic that I could touch his, but I couldn’t touch my own. Buck looked down at me and said, “I like to see girls’ eyes when they give me blowjobs. I like to watch them bulge as I try to fit my cock in their mouths.” He began to inch forward. I raised my chin and began to accommodate Buck’s cock. Anne had picked up the camera and brought is closer for a better view. I struggled as Buck started forcing his cock down my throat. It took the almost ten minutes before Buck’s ball sack was pressed against my chin. I was gagging, but I was determined to satisfy Buck. As he began to fuck my throat, he looked down to my watering eyes and blurted out a single word, “Amazing. I’ll come back to you later.”

Buck returned to the bed. Anne set up the camera and joined him. He rolled her over, pointed her ass in the air, and began performing cunnilingus. Anne moaned. After a bit, Anne suggested that she could get her pussy licked anytime. Taking the hint, Buck rolled her over on her back and positioned himself for Missionary sex.” Anne squealed as Buck start to insert himself into her pussy. It was a tight fit, in part because it had been a long time since her pussy was fucked. It took almost as long for Buck to get his cock in Anne’s pussy as it took him to force it down my throat. Once in, Buck started to slowly thrust in and out. Anne called out, “Harder. Faster.” Buck started fucking Anne like an animal. They both dripped sweet. After ten minutes or so, Buck flipped Anne over, raised her ass, pushed her head into the mattress, and started fucking her doggie-style, just like Anne fucks me. Ten more minutes of thrusting and Anne lets out an orgasmic scream. Collapsing to the bed, Buck and Anne laid side-by-side. As far as I could tell, Buck had not yet cum. 

I thought the two of them were going to fall asleep, but after a few minutes, Buck raised himself to his elbows, looked at me, and said, “Come here boy and make me hard.” I joined the two of them and began to give Buck a blowjob. Semi-hard initially, he was rock hard within a couple of minutes. Once hard, Buck asked, “Who wants their ass fucked.” Expecting it was my turn, I was surprised when Anne offered, “I have not been buttfucked in ages.” Anne had never allowed me to fuck her ass. Anne raised her ass in the air, “Michelle, come get my ass wet.” I responded by performing analingus. Understanding my roll, I also began probing her ass with my fingers, loosening her rectum, just like she would do for me during out “dates.” After a while she suggested she was ready for the real thing. Buck pushed me aside and began testing Anne’s anus with his cock. After ten minutes of so, he was only able to get about a quarter of his cock in her. It was too much cock for her ass. “Damn, I was looking forward to some anal”, Buck complained. Anne rolled over and suggested there was certainly an ass that could accommodate his huge cock, then she looked at me. 

Buck didn’t ask. He picked me up like a doll and dropped me face-down at the edge of the bed. Anne grabbed the camera and positioned herself. Pulling my panties off with one hand, Buck grabbed a tube of lube, squirted some of it on his cock and then some more on my rectum. Without any preparation, Buck rammed his cock in my ass and began to fuck me. Anne slipped the bowl under me with her free hand. Within minutes there was a steady stream of semen flowing into the bowl. Buck continued to fuck me hard. I could feel his cock swelling. He grabbed my hair and continued to thrust. Asking for Anne’s permission, “Can I come in his ass?” She replied, “No, the girls want to see you come in is mouth.” Pulling his cock out of my ass, Buck flipped me over on my back, pulled me by my legs off the bed, and stuck the head of his cock in my mouth. A few strokes of his hand and my mouth filled with cum. After the ejaculation stopped, Buck began fucking my mouth he had before. Anne offered, “Part of Michelle’s responsibilities are cleaning cock and swallowing cum.” Buck’s cock was nasty. It tasted of cum, fecal matter, and lube. Unlike plastic cocks, none of that was masked by the taste of plastic. I dutifully cleaned Buck’s cock, licking, and sucking it until it grew limp. Buck sat on the edge of the bed and said, “I have never done ass-to-mouth before.” I thanked Buck, “Thank you for fucking me, Sir.” Anne passed me the bowl with my semen, and I cleaned it as well. A sat on the floor. Buck cuddled Anne in the bed. Anne said the women has sent a plethora of messages. They had enjoyed the show. Ann turned the camera off and fell asleep with Buck, I slept on the floor.

In the morning I was still wearing the pink dress when Buck and Anne woke up. I had made them breakfast and served them in bed. I noticed the smell of sex in the room as I served them. After serving the food, I asked Anne is they needed anything else. Anne replied, “Yes, fluff Buck. I need another good fucking before I start my day.” Buck thew aside the covers and spread his legs. I gave him a blowjob as he ate toast and drank coffee. “I need to become wet as well”, stated Anne. She thew aside her coverings and I alternately sucked Buck’s cock and licked Ann’s pussy. After a few minutes Anne said, I want you to lick Buck’s asshole while he fucks me. Lick is balls as well. In fact, I want you to worship us while we fuck. Anne straddled my face and began rubbing her pussy on my face. Buck Kneeled behind her and began fucking her doggie-style. I could feel Buck’s balls slapping against my forehead. Anne orgasmed. Her juices flowed into my mouth. Buck continued to fuck her. “Cum on my ass, Buck.” A few minutes later, he shot is load, aiming for her anus. The cum flowed down past her slit and onto my face. Anne Sat up on her knees and positioned her anus over my mouth. “Lick!” I licked her clean. When I was finished, Buck presented himself to me. I licked his cock clean. “My asshole too.” I accommodated him. Buck wanted to shower before leaving. Anne joined him in the shower. I stood ready with clean towels and dried them when they were finished, Buck left. I never saw him again.

I was curious about Anne’s experience with Buck. She was apparently curious about my experience as well. During the week, she would catch me off guard with a question. “Do you feel gay for sucking Buck’s cock?” “What did Buck’s semen taste like? The same as yours? Were you humiliated cleaning Buck’s cock? Licking his asshole?  What did it feel like when you watched a man fuck me?” I wanted to ask her questions but was embarrassed to do so. Nonetheless, Anne offered unsolicited thoughts about her experiences. “Buck was the best fuck of my life. I enjoyed being licked by you while Buck fucked me. The ladies thought you make a fine cuckold.” By the middle of the week, Anne had not asked me to perform cunnilingus. On Wednesday I offered, and she said, “I am still sore from the fabulous fucking I received.” By Saturday she said, “I am ready for more sex. Let’s plan on a date tomorrow.”

At 7:00 I found my maid’s uniform had been laid out with the black panties. Anne usually only had me wear the uniform when I served guest. Before getting cleaned up, Anne informed me we would indeed have a guest. She said one of the viewers of the livestream the previous weekend wanted to join in the fun. “Monica was my roommate in college. You don’t know her. She and I will have sex tonight and you will serve us.” Anne told me to get cleaned up and dressed, then go to the kitchen and prepare some hors d’oeuvre. I did as she asked. I was in the kitchen, dressed in my maid’s outfit, and making olive tapenade when the doorbell rang. I answered the door. It was Monica. She complemented me, “You are prettier in person Michelle.” Inviting her in I directed her to the living room. I returned a moment later with a glass of sparkling wine. I told her I would tell Anne that she had arrived. Anne was in the bathroom getting ready for her date. She was wearing a cute dress. She smelled of perfume, something she never wore for me, and she had done her makeup. She told me to make Monica comfortable and make certain she had anything she wanted. “Yes, Ma’am.” I turned to leave, and Anne added, “She is very curious about you.” Answer any questions she might have.” I returned to the living room and told Monica that Anne would join her shortly. I started to turn to leave, then I remembered what Anne had told me.” I said, “Anne told me you are curious about me and I should answer any questions you have.” Monica responded, “I want to see your cage.” I lifted my dress and showed her. She asked to touch it. I gave her permission. She held the cage and asked if it hurts. I said no and she pulled on it, giving it a twist for good measure. I winced. “Does it hurt now?” Monica was a masochist. I said, “Yes, Ma’am. It does hurt now.” She let go. “Is there anything else I can do for you, Ma’am?” She reached for her glass and asked me to bring her more sparkling. When I returned, she had prepared some questions for me. “How does it feel to be fucked by women? How can you stand putting things in your mouth that have been in your ass? Isn’t eating cum discussing?” Before I could answer most of her questions, Anne walked in. Anne and Monica smiled at each other. “It’s been a while. I’ve missed you, Monica.” I had the feeling the two of them had been more than roommates. I left to get Anne a glass of sparkling wine. When I returned, Anne and Monica were making out on the couch.  “Michelle, Monica used to be my lover.” I had no idea that Anne was into women, but it made sense now that most of her friends were female. She clearly enjoys having sex with men. Anne went on and on about what a great fuck Buck was. Anne was bisexual. If Monica’s treatment of me was any indication, it seemed she was not into men. Monica didn’t mince words, “Michelle, Anne and I are going to go to the bedroom for a bit. You can wait here.” They left for the bedroom, and I took their place on the couch. I heard them making out in the next room. Both were breathing heavy, and they were moaning. After twenty minutes or so, Anne called me. When I entered the room, the lights were dim. Anne had her back on the headboard. Her legs were spread, and Monica was preforming cunnilingus. They were both nude. Anne said, “We’re thirsty, bring us some wine.” “Yes, Ma’am.” When I returned with the wine Anne was still leaned up against the headboard and Monica was standing beside the bed. The lights were on. Monica and Anne were naked. I passed them both a glass of wine. As I turned to leave, Monica said “I bet you’re thirst too.” I turned to look at her and before I could reply, she pointed to floor, obviously indicating she wanted me to sit there. I complied. “Lay on the ground.” I did what Monica asked. She straddled my face. “I want you to be my toilet. Will you do that?” I stared at her pussy. I would have preferred licking her. I replied, “Yes, Ma’am.” Monica began peeing in my mouth. She used her index finger to press on her urethra, thereby controlling the flow. I swallowed as she urinated. When she finished, I stood up and thanked her. 

I was about to leave the room when Anne said, “Monica is curious about milking, how you can cum without touching your penis.” I thought she was going to pull out the strap-on. Instead, Anne produced a vibrator and a bowl. “Stimulate your prostrate and show her.” The only way I had ever been milked was by being fucked. I didn’t know if it would work. Monica joined Anne leaning against the headboard. I removed my panties and got on my hands and knees at the foot of the bed. I placed the bowl between my legs, just below my cage My ass faced the two women as I turned on the vibrator and slowly inserted it in my ass, The vibrator felt good. Before long, semen began to stream from the cage into the bowl. The vibrator was intense. I moaned and then cried. The “anal orgasm” was intense. My whole body shook. After a few minutes I turned the vibrator off and pulled it from my ass. A final spurt of semen shot from the cage into the bowl. Sitting up, Anne said, “You know what to do.” I put the vibrator in my mouth and licked it clean. I then picked up the bowl and licked the semen out of it. Monica watch intently, then suggested, “You must be a great asslicker.” Anne answered on my behalf. “Yes, he is.” Monica asked me to show her. She got on her knees and presented her ass to me. I crawled over and began to lick. Her anus as musky, unclean. I suspect she knew that. She asked me to clean the inside of her butt. Being practiced with Anne, I curled my tongue at set about penetrating her anus. It seemed loose and I had no problem inserting my tongue. Monica pressed back and forth, anal fucking my tongue. “Boy, you’d make a great toilet slave.” She got off humiliating me. Anne made it clear they wanted to be left alone. I went to the couch and waited. I heard them having sex. The noises last for about ninety minutes. I heard multiple orgasms but was uncertain who was having them. I heard them whispering for a while and then lights went out. I was never invited back into the room. I got a blanket from the closet and slept on the couch.

In the morning I got up early to make breakfast. I wasn’t sure about Monica, but I knew Anne needed to go to work. I took off the maid’s outfit. It smelled of urine. I assumed Anne would want me nude, so I didn’t put clothes on. Monica came out first. She grabbed my cage and twisted, “I am grumpy in the morning before my coffee.” I told her I would get her some and she let go. Anne came out fifteen minutes later. She wanted coffee too. Both women were only partially dressed. Their breasts were exposed. Sitting down at the dining room table, I served breakfast. While I was clearing the table, Anne said goodbye at the front door. The kissed and Monica left. Anne got ready for work without any further discussion. I was already home when Anne returned. Without elaborating, Anne simply said, “Monica will be joining us for date nights for a while.” I did not ask for any more details and Anne offered none.

The week went by slowly. On Saturday there were on clothes laid out for me. Before getting cleaned up I asked Anne what she wanted me to wear for date night. “Monica prefers you nude. Nude at all times when you are with us.” Do you want me it be in my position at 8:00?” “No, Monica is coming at 7:30. I will be getting ready. I need you to answer the door.” Almost as an afterthought, she said, “You are still a cuckold, only Monica is my bull now.” I didn’t understand what that meant but went with the flow. I got cleaned up and sat in the living room waiting for Monica to arrive. Anne was in bathroom getting ready for her date. I was uncertain what I was supposed to be doing. A few minutes before 7:30, the doorbell range. I looked through the peephole to make sure it was Monica, then I opened the door. She was smartly dressed. She had had hair done. I asked her in, lead her to the living room, and asked her if I could get her anything. “I could really use a martini. Gin, dry, and a lemon twist.” I excused myself to make her drink. When I returned with the martini, Monica has standing at the window. I set her drink down on the end table by the couch and asked if I could get her anything else. She asked me to have a seat. I sat in a chair across from the couch. I felt uncomfortable in nothing by the cage, especially when Monica was dressed. Monica started the conversation. “This is your date night with Anne? This is the evening when you are milked?” I responded, “Yes, Ma’am”. “I can see you are trying to show me respect, but I like to be called Mistress.” The obvious question was then answered without prompting, “Anne is okay with you calling me Mistress. She has also afforded me other liberties.” I asked, “What are those, Mistress?” She responded by telling me the obvious, “I am a disciplinarian. Anne has asked me to provide some order. But let’s keep with the original subject. You are to be milked today. I will milk you. You will explain the process to me. But, to return to the second subject, I will disciple you. Discipline first, then I will milk you. I will spend the remainder of the evening with Anne.” “What disciple is required, Mistress?” She explained, “That of course depends on this week’s transgressions. Anne has shared with me a few things you did this week that are unacceptable. First, you left the toilet seat up twice. I am of course not talking about the horseshoe since I know you need to sit down like a girl toc pee. I am talking about the lid. You left it up twice. Anne had to remind you she prefers it to be kept closed when it is not in use. There were other transgressions. You drank the last can of soda water. You forgot to bring the mail in on Tuesday. Anne told you the lawn needed to be mowed this week, but you didn’t do it. There were other, less serious transgressions.” “What is my punishment, Mistress?” “Well, issues that involve the bathroom has two consequences. First, you have lost your bathroom privileges until next Saturday. You will pee outside. You will make a latrine hole and defecate outdoors. You will shower outdoors using the hose. Second, you will drink every bit of urine that is produced in the house this week. Is that all clear?” “Yes, Mistress.” As for the other transgressions, I prefer to use a cane. I believe you have some experience with the cane. Do you know where it is?” “Yes, Mistress.” “Bring it to me.” “Now?” “Yes!” I returned a few minutes later with Anne’s cane. And tried to hand it to Monica. She refused it and asked, “Is this how Anne receives her cane.” I explained this was the first time I had touched Anne’s cane. “I see. Go to the middle of this room, Sit kneel and hold the cane out in front of you in your hands, palms up.” I complied with her orders. Monica followed, stood in front of me and took the cane. “When I take the cane, you are to assume the position, face to the ground, arms stretched out in front of you, and your ass in the air. You know to count, right?” I responded by assuming the position and saying “Yes, Mistress.” By this time Anne had joined us. She sat on the couch and observed. Monica explained, “I have tallied up the number of strokes. There will be fifteen.” She began tapping the cane on my ass, then whap. “One, Mistress.” Whap. Whap. Whap. Monica struck me harder than Anne, I counted off the blows. I was afraid I would pass out before she was finished, but I soldered through. When finished, Monica explained I should receive the cane the same way I delivered it. I kneeled and put my arms out with my palms up. Monica placed the cane in my palms then said I should thank her. “Thank you for disciplining me, Mistress.” I returned the cane to the closet and then returned to the living room.

Monica was finishing her martini and talking with Anne, who was drinking a glass of wine. “Oh, Michelle, let’s get that milking out of the way”, said Monica. It was clear that Anne has delegated these tasks to Monica. “Bring me my bag. I left it by the door.” Fetching the bag, she pulled out her strap-on. “I am used to using a strap-on with my female lovers. I have never fucked a man, but I suppose the principles are the same. Go to the place where you are milked. I will be there soon.” I went to the bedroom and assumed the position. Monica followed a few minutes later. She was nude except for the strap-on she was wearing. “I don’t want to soil my clothes.” Placing a bowl underneath the cage, I heard a tube of lube open and a squirt, presumably on Monica’s cock. I did not hear her put on a glove. It was clear she did not believe in going easy on me. She did not loosen me. She pressed her dildo on mu anus until it surrendered, and she started fucking me immediately. At first it felt like she was not using lube, but in a few minutes the lube was spread around, and my anus relaxed. She pounded me violently and semen dripped from the cage. When she finished fucking my ass, she pulled me to the floor by my cage and stuck her cock in my mouth. She fucked my mouth with about the same violence that she fucked my ass, then handed me the bowl. After licking the bowl clean, Monica put one of her feet on my chest and pushed me to the ground. Positioning herself over my face, she urinated in my mouth. When the flow stopped, Monica said, “You are not only urinal, but you are also the toilet paper. Lick my pussy clean after you swallow my pee. I complied. I took a moment before collecting my thoughts. Walking through the living room, Monica was once again dressed and was sitting on the couch. I excused myself and went to the back yard to pee.

When I returned to the living room, I asked if anything was needed. “More wine, Michelle”, said Anne. I left and returned with the botte and a glass for Monica. I filled it and topped off Anne’s. “Give us some privacy, Michelle”, said Monica. Since I thought it poor form to occupy the bedroom, I left the women in the living room and went outside where I sat in a lawn chair. After an hour or so, Monica came to get me. She was naked. “We want you.” I followed her to the bedroom. Anne was in bed, also nude. Monica explained, “You are the ass licker. If a rosebud is exposed, I want your tongue on it.” Monica then straddled Anne’s face and Anne licked her pussy. While Anne performed cunnilingus, I licked Monica’s anus. After about ten minutes, Monica stood on the floor and Anne kneeled in front of her licking her clit. I kneeled behind Monica, spread her ass cheeks, and licked Monica’s anus. After a while Monica laid on her back and pull her legs into her chest. Anne licked Monica’s pussy. I serviced her asshole. A few minutes of this and Monica experienced an orgasm. Monica was a squirter. Anne stepped away while Monica’s urine squirted in rhythm with her orgasm as I continued to fuck her anus with my tongue. When the spasms subsided, I felt Anne tap my shoulder. She pointed to the floor, and I laid down. Anne straddled my face the same way Monica had earlier and urinated in my mouth. I swallowed enthusiastically and licked her pussy clean when she finished. Standing up, Anne pointed at the door, and I left.

Laying on the couch, it was clear from the sounds that Anne and Monica were fucking each other with strap-ons. Like the weekend before, the lights were turned off and Anne slept for Monica. In the morning I carried out my responsibilities and showed Monica off. Before she left, Monica turned to me with some instructions. “I will be back next Saturday. I will let myself in. I would like you to prepare for me. Fetch the cane, my strap-on, and a bowl. I would like you to be in the disciplinary position in the middle of the living room floor, cane in your palm, and the strap-on and bowl within reach. Be in place by 7:30.

The weekdays passed. On Wednesday Anne had a guest, a former boyfriend. They had separated on good terms and would get together a few times a year to catch up. Anne let me wear normal clothes while her guest visited. John and Anne talked about shared experiences and matters I knew little of. I served them drinks but otherwise tried to stay out of their way. At one point John asked where the bathroom was. I gave him directions, but Anne overheard. “Michelle, you know your responsibilities this week. Monica would be very disappointed if you shirked those responsibilities. “John, Michelle is a submissive and she is being disciplined for a transgression. This is awkward, and I don’t know quite how to explain, but Michelle is expected to drink all the urine that is produced in the house this week. John laughed. “You’re kidding right?” “No, I am quite serious. You can pee in a cup if you like and Michelle and drink it later, I mean if this makes you uncomfortable.” John replied, “Is that what you do?” “No, Monica and I pee right into his mouth.” “Su casa”, John replied. What other kink are you into?” Anne replied, “Michelle is a cuckold to me and my lover. He wears a chastity device.” John exclaimed, “Wow, I didn’t know you are so kinky. I am into some stuff as well. You know I am bisexual.” Anne told John she was aware of his sexual preferences. John had a male lover before Anne, and he did not keep it a secret from her. “I’d find it sort of a turn-on to pee in his mouth, but do you need to watch.” Anne replied, “Of course not. I will give you some privacy.” As Anne turned to leave, John said, “Actually, my dick is nothing you haven’t seen before. You can stay. Can I see the cock cage?” I ordered Michelle to take his clothes off and kneel in front of John. But this time, with the delay, there was some urgency, and John whipped out his cock, stock it in my mouth, and peed. It was like a fire hose, and I choked as my mouth and throat filled with urine. When finished, I asked, “Sir, may I clean you?” John let his cock dangle. I put it in my mouth and cleaned it. Watching John urinate, Anne felt the need and she ordered me to lay down. Pointing aways from John, not giving him a very good view, Anne urinated in my mouth. I cleaned her when she was finished. The rest of the evening was unremarkable.

When Saturday arrived, I prepared for Monica. At 7:30 I was naked, kneeling in the middle of the living room, and displaying the cane. Monica let herself in and glanced over at me. I stared at her. “Lower your eyes in my presence.” I immediately looked at the ground. Monica walked over to me and took the cane. “I received a good report from Anne about you this week. There were a couple of minor transgressions. I am returning bathroom privileges to you. You may pee, shit, and shower in the bathroom again. However, I believe it is a good reminder of your responsibilities for you to continue to serve as a urinal when called upon to do so.” “Yes, Mistress.” Also, on second thought I believe there was some value in feminizing you, so I will ask you to wear feminine clothing except when called upon to be naked. You should wear such clothing when inside this house, regardless of who else may be present. I understand you have three outfits, two dresses and a nightie. Wear the maid’s outfit whenever you are serving. Wear the pink dress when you are not serving. Wear the nightie when you are going to be fucked. Put on the nightie now.” “Yes, Mistress.” I returned wearing the shear white panties and nightie. I would like you to wear lipstick. When you are wearing the nightie, I want you to wear fuck-me red. When wearing the pink dress, pink lipstick. When you have your maid’s outfit on, wear white lipstick. By this time Anne had joined us. Anne offered, “Come with me. I will show you where the lipstick is.” Minutes later, Anne I returned, and I had on red lipstick. “Go to the bedroom and wait for me.” I left the room. A few minutes later, Monica joined me. “I understand Anne has fisted you before.” “Yes, once, Mistress”, I replied. “Interesting. I have never fisted anyone’s ass before. I am going to milk you tonight with my fist.” It should have been a clue that Monica had no intention of fucking me with the strap-on because she was still dressed, and she always took off her clothes before putting on her strap-on. Monica pointed pulled down my panties and I stepped out of them. Pointing to the edge of the bed, I assumed the position. Monica returned a minute later wearing a black latex glove that went practically to her shoulder and a large bottle of lubricant. Like Anne used to, Monica started.  with a few fingers and worked her way up the duck-head. Within five or ten minutes, she had her entire fist in my ass. Thrusting it in and out up to her elbow, it felt different than a strap-on. More personal. More organic. Soon my semen squirted out into the bowl. Monica had successfully milked me by fisting. Unknown to me, Anne was standing by her side. When Monica was finished, she removed the glove and handed me the bowl of my semen, which I dispatched within a few seconds.

“You will serve us the rest of the evening.” I took that as a cue and went to the bathroom to clean up before putting my maid’s uniform on. I returned to the living room and asked if anything was needed. Monica looked at me and said, “Yes, the cane.” I fetched the cane and assumed the position in the middle of the living room to deliver it to Monica. Monica took the cane from me and asked, “What color lipstick are you supposed to be wearing.” I had forgotten. I was still wearing my “fuck-me red” lipstick and I was supposed to have white on. I said, “White, Mistress.” “Yes, ten blows. Count them.” Monica pulled down the black crotchless panties I was wearing to expose my bare skin, then she delivered the punishment. When she was finished, I pulled up my panties and continued the tasks associated with serving. The rest of date night was unremarkable. Anne and Monica slept together after their sex and I slept on the couch, as usual.

Early in the week, Anne informed me we were invited to a party on Friday. Friday morning before work, Anne told me, “We both need to take off work early today. Be home by noon.”  When I got home from work, Anne was already there. I had made an excuse at work and pretended to be ill to take the afternoon off. “I bought you a new outfit for the party, Michelle. It’s on the bed.” When Anne called me Michelle, I always knew she was thinking of me as a sissy. I went into the bedroom and examined the clothes. For the first time, I had been given a complete outfit. There was a sheer white blouse, a short green plaid skirt, white nylon stockings with a garter belt, a stuffed A-cup bra, silky white thong panties, and a pair of white slippers. There was also a white wig with straight, shoulder-length hair. Anne called from the living room, “Don’t get dressed yet. We need to do your makeup first. Monica is coming over to help.” I gave myself an enema and took a hot shower. Monica was standing in front of me when I stepped out of the shower. Curling her finger, she motioned follow her. I dried myself off as we walked to the bedroom. There was a plastic sheet laid over the bed. There were also cuffs at the corners of the bed. “Lay down on your back.” I laid down and Monica cuffed my wrists and ankles. “We need to get you cleaned up.” Then to my surprise she produced a pair of bolt cutters and removed the padlock on my chastity cage. The cage came off for the first time in about 18 months. I understood the bondage. She didn’t want to fight being recaged. Monica left the room. There was a knock at the door. Monica returned a minute later with a petite Asian woman. “This is Ming. She is going to get you cleaned up.” Ming set up her equipment while I laid spread-eagle in bondage, completely nude. Just before she began work on me, she said in broken English, “This hurts. I like hurt men.” She spread wax on my chest and went to work. I yelled at she ripped the hair from my body. She removed all the hair she could reach, leaving my groin for last. “This hurt most.” As she removed my pubic hair she said, “Your penis small.” Finished with the top, she called Monica into the bedroom. Monica was carrying a new chastity cage. It was much smaller than my old one. She delighted in showing me the device, which was not so much a cage but rather a plate, and it had a urethral tube. Monica kneeled between my legs and started to put the cage on me. Anne had come in to watch with Ming. The ring was slipped around my junk. She lubricated the urethral tube and forced it in. The tube burned as it was inserted. Monica had to push my atrophied penis into the shaft’s cavity to position the plate. I expected to hear a padlock close, but instead Monica produced a riveting tool and used it to secure the chastity device. Once recaged, Monica released me from bondage. “Flip over. Ming will do your backside.” Ming did my backside the same way she did the front. She left my anus for last. Monica came into the bedroom just as Ming was finishing up. “Now for your face.” Monica motioned for me to sit in a chair. Ming removed hair from my ears, nose and parts of my face. She then worked on my eyebrows. Finally, she produced a pair of electric clippers and gave me a buzzcut. Having completed her work, Ming packed her tools and left without saying anything else. I stood in front of the mirror. I did not recognize the person I saw in the mirror. Monica stood behind me a smiled. “Now your makeup. Pay attention because I expect you to do this yourself going forward.” Monica applied foundation, blush, mascara, and lipstick before fitting me with a wig cap and arranging the wig. “You can get dressed now.” I walked into the bathroom and looked in the vanity mirror. I looked like a 25-year-old woman.

I began by putting the panties on. Nearly flat on my pelvis, you could hardly tell I was wearing a chastity device. I noticed how smooth my butt cheeks felt, which were exposed by the thong. I put the bra on. It made me look like I had breasts, albeit small ones. I put the stockings on and struggled to understand how the garter belt worked. I put the blouse on. It was so shear; you could see the bra beneath it. I put on the skirt, which was so short that you could see my underwear if I bent over. Finally, I put the slippers on. Looking at the myself in the full-length mirror, I thought I could fool myself into thinking I was a woman. Anne can into the bedroom as I examined myself. She stood behind me, slipped her hand underneath the skirt and rubbed her hand over a butt cheek. “Perfect. They’re going to love you.” I didn’t ask who she was referring to. I had learned that such matters were beyond my control. “One last thing.” Anne dabbed some perfume behind me ears. It smelled floral.

I walked with Anne into the living room. Monica was standing by the front door. “Ready.” I nodded affirmative. “Let’s take my car.” As we walked to Monica’s car, she corrected me. “I would like you to walk with more confidence. I want you to sway your hips like a woman.” She had me practice on the sidewalk in front of the house. It was the first time I had worm women’s clothing outside the house. I was being paraded in front the neighbors. When I had performed satisfactorily, we left in the car. The drive took about a half hour, just to the other side of town. The house had a large driveway that was lined by a dozen cars. We parked, exited the car, and I did my best to walk as a woman to the front door. Monica and Anne walked behind me, no doubt admiring their handiwork and grading my performance. Anne ran the bell. I did not recognize the woman who answered the door. She was pretty. She knew Anne and Monica and gave each a kiss on the lips. Once inside, Anne introduced me. “Donna, this is Michelle.” Donna smiled, “Lovely to meet you, Michelle.” We were led to the backyard where there were several dozen people mingling. There was a pool, and a few women wore bathing suits Probably three-quarters of the people were women, but there were a few men as well. I counted four. Food and drinks were being served by two waiters. I noticed the men and women were segregated. The men were grouped together, and the women were mostly talking with other women. We joined a group of women who were sitting on lawn chairs. There was an empty bench long enough for the three of us. Anne and Monica sat on either end of the bench and Monica patted the space between them, indicated I should sit there. I sat down careful not the expose myself and I modestly crossed my legs. There were introductions. Most of the women seemed to know each other. I did not speak, believing my deep voice would reveal the charade, although I suspected everyone was in on the joke. We joined other groups and within an hour had met most of the women at the party, but none of the men. Curious, I asked Monica who the men were and she, “They are the guys who are going to fuck you later.” I apprehensively followed up, “Where will the sex be, Mistress?” Anne answer on Monica’s behalf, “You are going to be the entertainment.” I shifted anxiously in my seat. I began noticing the women were throwing me glances. Everyone had known the plan before the party except me.

An hour later, Monica pulled me aside and said it was time to get ready. She explained, the women had parties once a month and there was always a sex show. I was told the women in the audience are mostly into women, but they enjoy watching gay sex. They had never seen a sissy gangbanged by men, so that was scheduled for tonight. I tried to protest, “But, I am not a sissy, Mistress.” Monica laughed, “Have you seen yourself in the mirror, bitch. You are the most girly boy I have ever met.” I realized I had been transformed. It was slowly at first … chastity, pegging, the role playing in the bedroom and domination. But in the last eight hours everything had moved very quickly. I was hairless, in a chastity device that seemed to eliminate my penis all together, and out in public in the most elaborate makeup I had ever worn. “Let’s introduce you to the men.” I was led into the living room where the four men were talking. They stopped talking and faced us when we walked in. “Gentlemen, this is Michelle. She is going to be your date for tonight. The men circled around me. They were larger than me. They were bodybuilder types, like Buck, the man who cuckolded me for a day. They were also all taller than me. They all had stubble beards and tattoos. They began introducing themselves: Josh, Alan, Malcom, and John. John was the first to touch me. Facing me, John seemed to place me in his shadow. He placed both hands on my ass and pulled me closer. Smelling the perfume, he kissed my neck and whispered in my ear, “My cock is humongous, but you should see Josh’s.” He chuckled. “Oh, I guess you will.” Malcom walked behind me while John continued to hold me. Malcom lifted my skirt as to examine the merchandise. Alan and Josh took their turns manhandling me. Alan rubbed my cage while he suggestively stuck his thumb in mouth. While Alan was doing that, I heard Josh pulled the thong aside and rubbed his index finger on my anus. Monica interrupted the foreplay to suggest they should “save it for the show.” Monica took my hand and led me into the next room. The men followed. The room seemed to be too large for a bedroom, but there was a bed in the middle of the room. Chairs lined the room. There were bright lights overhead. Clearly this was the stage. Monica led me to the bed, and I sat on the edge. The men stood at the four corners of the bed. I had not yet quite gotten my bearings when the women started filing in. They all had drinks in their hands. Anne joined Monica and they sat together on the two seats that were closest to the bed.

Donna, the woman who had greeted us when we had arrived at the party was the MC. She welcomed everyone to the party and to the “main event.” She first introduced me. “This is lovely Michelle. Michelle is a whore who cannot seem to get enough cock.” Donna seemed to be making things up as she spoke. She then in turn introduced the men. As each were introduced, they artfully stripped off their clothing. This was not the first time they had performed for a crowd. Once the four men were naked, Donna simply said “enjoy.” She was looking at me when she spoke the word. Did she expect me to enjoy this? The men? Or was she referring to the women in the audience. No matter, the men did not wait for an invitation. My eyes focused on their mostly flaccid cocks. Their limp cocks were larger than my erection used to be. In fact, there were larger than the first dildo Anne had fucked me with. Josh did have the largest cock. It seemed twice as large as the others. It wasn’t human. Alan was the first to approach me. “On your knees, whore. Make me hard.” I kneeled in front of him and took his penis in my mouth. Alan grabbed the back of my head and put the whole thing in my mouth. Even flaccid, his penis went down my throat. I focused on keeping my gag reflex in check as Alan forced my head back and forth. His erection grew in my throat and in a few minutes, he was rock hard. Pulling his stiff cock out of my throat, I noticed lipstick on his shaft before he slapped my cheek with it. Picking me up like I was weightless, he set me down on all fours on the corner of the bed. John took his place and put his flaccid penis in my mouth while Alan hiked up my skirt. The garter belt covered my panties, Alan kneeled behind me, he pulled out the thong strap from my ass crack and bit two notched in the panties before ripping them off me. As I worked to get John hard, Alan spit on my anus and started probing it with his thumb. It was clear he had no intention of using lube. Alan began stretching me as John grew in my mouth. After a few minutes, Alan inserted his cock. Without lube is burned as he humped me. I could hear him spit periodically. John was now hard. I expected him to get in line with Alan, but instead he fucked my throat. Alan and John pumped in rhythm. They both penetrated at the same time, Alan in my rectum and John down my throat. Alan was the first. He filled my ass cum. He continued to fuck me. His cum lubricated his cock, which slid in and out without friction. In unison, Alan and John switched places. John began sodomizing me. Alan stuck his dirty cock down my throat. As he started becoming semi-flaccid, I could taste the last of his semen flow in my mouth. Alan sat on the edge of the bed, clearly winded, and Malcom took his place using my mouth. John was pounding my ass even harder than Alan had, but I was well-lubricated by Alan’s semen, and I enjoyed being fucked as I noticed for the first time that I had been leaking semen, which was pooling underneath me. In a streak that traced the path of the thrusts. John lasted longer than Alan had. After fucking me for at least twenty minutes, John switched places with Malcom, who was now hard. John had not yet ejaculated. John began fucking my mouth, working his cock down my throat. Malcom was busy pounding my ass. Without any warning, John released his load in my mouth. I was shocked by the amount of cum. I had eaten a lot of semen, mostly my own, but I usually licked it in small quantities from a bowl. I had never been required to swallow such a large quantity. I gagged. John put a finger under my chin and redirected my face until my eyes were looking up at his. He smiled and said, “That’s my first load cocksucker.” 

Josh was the last of them to use my mouth to et hard. I was terrified by his freakishly large cock. Josh’s flaccid penis filled my mouth and only half of it was in. Before Josh was hard, Malcom grunted as he orgasmed. Josh was occupying my mouth, but he pulled out long enough to clean Malcom’s cock. When I finished that task, Josh resumed using my mouth. Able to focus my attention on one person, I gave Josh a proper blowjob. I remembered back to the relatively few blowjobs I had received for inspiration. I polished the glans. All four of the men were circumcised. Since my ass wasn’t be used, I moved to sit on the edge of the bed. I felt semen flow and realized it wasn’t mine. It was leaking from my asshole. I saw my ripped panties on the floor. For the first time I noticed the audience. Because the bright light focused on the bed, it was hard to make out faces. Josh stepped in front of me, and I held his cock. I couldn’t span the circumference with one hand, so I gripped it with both. The head of the cock practically filled my mouth. I stroked him as I suck as much as I could fit in my mouth. The cock would not fit in my throat. After perhaps twenty minutes of sucking him, Josh removed my blouse. Like Alan, Josh couldn’t be bothered to undress me conventionally. He pulled the front of the blouse apart until the buttons gave way and tugged the blouse off my back. Pushing me backwards, he also pulled off my skirt. I was left wearing the bra and stockings that were held up by the garter belt. I had lost the slippers I was wearing somewhere along the way. Josh flicked the flat disk of metal that covered my penis making a ringing sound, and he pushed my legs back behind my head. His cock was so stiff he didn’t have to guide it with is hands and instead just moved forward pressing its head against my asshole. The hole had been stretched by the previous cocks, giving Josh a target, albeit one that still wasn’t large enough to accommodate Josh’s cock. I reminded myself that my ass had accommodated Monica’s fist, but sizing up Josh’s cock, I realized that it was bigger in circumference and longer than Monica’s forearm. As he pressed harder, the tip of his cock passed the rings of my anus with an audible pop. The area behind the glands had significantly less girth than the shaft that followed, the middle of which was swollen like a balloon. As he penetrated deeper, it was like a giant tapered butt plug stretching my anus. I began noticing how full my rectum felt. I had no way of gauging how much of his cock had been put in me. He just kept pushing and a seemingly endless supply of Josh’s cock was forced into my ass. I finally felt his pelvis bottom out. Josh left his cock in place for a minute, then he began pulling is halfway out before slowly reinserting it. I could tell he was being careful. After ten minutes of this in-and-out, Josh started really fucking me.  He would pull out until just the head was in me, then drive forward until his pelvis slammed against my hips. This continued for a while. While still impaling me, Josh grabbed me by the waist and stood up. I held him by his neck as he executed a few more thrusts, then he sat down on the edge of the bed. He wanted me to do the work. I got my knees underneath me and began lifting myself up and down. I looked down and watch my belly swell as Josh’s cock penetrated me. I was still wearing the bra, garter belt, and stockings. I might have been a woman if not for the shiny chastity device in my pelvis. Josh leaned back on his arms as I continued to ride his cock cowgirl style. It was clear he seemed to enjoy watching his cock slide in and out. I noticed him staring at my chastity device. He seemed amused. I grew tired and began slowing down. Josh was ready to fuck now. He lifted me off his cock and dropped me on the bed face down. Grabbing my hips, he pulled my ass to his cock. One thrust and he was completely inside me. I moved several feet as he thrusted back and forth. I had never experience suck a fucking. It seemed to go on forever. He grunted like a bear each time he thrusted forward. The grunts became louder and the tempo quickened as the minutes passed. I imagined his eyes were closed and he was just focused on humping a hole. After perhaps 30 minutes with Josh’s dick in me, he started slowing down the pace. His thrusts seemed more deliberate, and the grunts morphed into shouts, almost screams. I felt him cum. The stream felt like there was a hose in me with the faucet turned wide open. Pulling me back by my legs onto the floor, Josh was still pumping cum when he stuck his cock in my mouth. I choked, but I couldn’t tell if it was because of the gooey mess he was pumping in my mouth or the fact he was making his best effort to fit his shaft in my throat. As the stiffness began to relax, I sucked him, cleaning the cum and ass off his cock. He pressed me to lick the semen from his pubic hair as well. Finally, he reached turned me around, pressed my head to the floor and stuck his fingers in my rectum, scooping out semen. His fingers covered, he turned me around and stuck his fingers in my mouth. I licked them clean. Sitting on the floor and leaning against the bed, I looked over and observed the other three men stroking erections. They were ready for round two.

John was the first one to jump in for round two. He lifted me off the ground, unclipped the bra and pulled it off. He pulled the garter belt over my hips, pushed me to a sitting position at the edge of the bed, and pulled the garter belt off together with the stockings. Reaching down, he pulled me to my feet by my cock cage. I squealed in pain. Taking my place on the edge of the bed, he pulled me face-down across his lap. Not understanding what he was trying to do, he began to spank me. First one cheek then the other. My ass became more sensitive the longer he spanked me. He stopped as I started to cry.  Grabbing me by my hips, he pulled me across his lap until his semi-hard cock was in my face. Still wearing the wig, he pulled it off and the wig cap so he could see what he was doing as he stuck his cock in my mouth. The angle was odd, but he pushed on the back of my head to force his dick in. I sucked on him until he was hard again. Twisting me around, he sat me in his lap with my back to his chest. Lifting my hips, he lowered me onto the shaft. Laying down, he wanted me to do the work, so I got on my knees and fucked him reverse cowboy style. He gripped the cheeks of my ass, one in each hand. My butt was inflamed from the spanking, and his grip on me was uncomfortable. He assisted by pushing my ass up and letting drop back down with a thud. John set the pace. I imagined from his vantage he was watching his cock slide in and out of my rectum. I faced half of the audience. I could make out the faces of the women who watched the show enthusiastically. Except for the piece of steel that covered my nub, I was naked. The steel was covered with cum, I imagine a combination of mine and theirs.  Without any hair on my body, I saw scratches and rug burns all over. My naked ball sack bounced with each thrust. John lasted long the second time around. Exhausted, at the point I could no longer lift myself. John pushed me off, stood up, and push me face down on the bed. Intend to finish himself off, I laid flat on the bed when John mounted me. Laying on my back, he fucked me hard. Sweaty, he slid along my back, and he slid his cock in and out of me. It didn’t take long at this point for John to cum. He pushed his cock extra deep as he was drained. John laid on top of me until he began to go limp. His penis slipped out of my ass. Rolling me over, John kneeled over my face. He first put his ball sack in my mouth. It was gooey with cum. While sucking his balls, his limp penis oozed semen onto my cheek. John scooped up the cum with his finger, took his balls out of my mouth, then stuck the cum-covered finger in my mouth. This was followed by his penis. John got off me and I saw him leave the room.

Malcom stepped forward. He already has an erection. He held out his hand and helped me to my feet. Turning me around he pushed on my back. Still standing, I supported myself with my arms on the edge of the bed while Malcom entered me from behind. My balls felt bruised, and I felt Malcom’s sack slap into mine with each thrust. This was essentially my only sensation as my ass was numb after hours of being penetrated. Malcom was all business. He just fucked. But he fucked and fucked and fucked. I lost track of time but eventually Malcom stopped hammering my rectum, turned me around, pushed me to the ground, and finished himself by jerking off until he came in my mouth. I sucked his cock clean. I watched him pick his clothes off the ground and leave.

I looked up and saw only one man left. It was Alan. He fucked me a second time while I laid on my back on the bed and he kneeled. Most of the time he my gripped the back of one of my thighs with one hand and he held onto my balls and cage with the other. Pulling the cage to the side and pushing one leg back presented my hole at an angle that allow him to drive himself deeply into my ass. It felt like his cock was sideways in my abdomen. After a while, he let go, pressed his body forward to drive my legs to either side of my head and he pile drove straight up and down. At one point he pinched and twisted my nipples. I screamed. Near orgasm, he withdrew and jerked himself off. I prepared to take his load in my mouth like Malcom had done, but I was surprised that Alan let his cum fall in a pool on the floor. When he was finished. He grabbed me by the back of my neck and pushed my face into the pool of semen on the floor. No longer having any respect for myself, I licked up the cum. Like John and Malcom, Alan collected his clothes and left. All the lights came on. It seemed the show was finished.

I watched the women make their way to the door. Anne and Monica walked up to me. Monica said, “Let’s get you cleaned up.” Donna directed us to a bathroom. Monica handed me an enema and told me to clean myself out. Walking past the mirror I got a good look at my appearance. What was left of the makeup was smeared all over my face. Anne drew me a bath and I got in it. I washed the filth off and cleansed my wounds. After bathing Monica suggested I needed to reapply my makeup. “It is important to look after your appearance.” I did not argue with her logic.  I applied the foundation, blush, mascara, and lipstick as she had taught me earlier in the day. Anne was brushing the wig behind me, and when I had finished with the makeup, she put the cap and wig on me. I looked very feminine again, but I had nothing to wear. My clothes had been destroyed. Monica returned holding clothes. “Donna had clothes for you to wear.” She spread them out on the counter. There was a black lace-up corset. A pair of black see-through panties that had a silk bow in the back, a black garter belt and stockings, and a pair of black, elbow high gloves that did not have fingers. I held up the corset and said, “I don’t even know how to put this on, Mistress.” Monica loosened the laces and put the corset around my waist before lacing it up again from behind. Tugging on the laces, my abdomen shrank. The corset pushed my chest together and made it look like I had breasts. It gave me an hourglass shape. I put on the panties, stockings, garter belt, and gloves. I looked at myself in the mirror, not recognizing the person I was looking at. I turned to face Anne and Monica. Monica then explained the situation, “Josh really likes you. He wants to spend the night with you.” I protested, “I have nothing more to give, Mistress.” Monica elaborated, “This is not a show. He will be gentle.” I was too tired to argue, and I’m not sure it would have done any good. I was dressed like a whore, had no money, and I did not have a car to get home. I agreed to spend the night with Josh. Monica reiterated, “This is not a show, but there may be a few people watching you.” I asked who, and Monica said, “Donna.” “Where will you two be, Mistress.” Anne replied, “After the show, Monica and I are horny. Donna is giving us a room for the night.” 

Anne went to their room while Monica took me to Josh. Outside the door of the bedroom, Monica gave me some instructions. “Behave yourself. Give Josh anything he wants. Oh, you should also obey your host, Donna.” “Yes, Mistress.” I knocked on the door and Josh opened it. Josh was wearing black dress pants, a black leather belt and matching dress shoes, and a white button-down dress shirt with just the last button unfastened. He handed me a flute with sparkling wine as I stepped into the room. I thanked him, “Thank you, Sir.” Josh smiled, then he leaned over and kissed me on the lips. It was the first time a man’s lips had touched mine. I almost recoiled but controlled my visceral response. Josh took my hand and lead me outside to a balcony. The balcony overlooked the pool. It was dark, but the pool area was well-lit. Several people were socializing around the pool. I could make out Anne, who had been joined byMonica. They were sitting in chairs by the pool, holding hands. I looked at Josh, he was holding a flute and reached over to click mine. Josh looked about 6’6”, at more than half a foot taller than me, and perhaps 250 lbs. at least 70 lbs. more than me. He looked eastern European, perhaps Hungarian, or Czech, but his English was native American. He moved closer to me and asked if I was cold. Only then did I become aware how I was dressed. I sat the flute down and asked if I could use the restroom. Josh sat his flute down, took my hand, and led me to the bathroom. I walked into the bathroom and started to close the door, but Josh stopped me. “I like to watch.” I stood over the toilet like I was going to pee standing up, then I turned around and lowered my panties as I sat down. Who was I kidding. The cage made it necessary to pee like a girl and Josh knew it. Furthermore, I had to wipe myself with tissue when finished, just like women do. Josh watched me perform the ritual. “You know, I didn’t like the way the other boys were treating you. That’s why I left. Can we start over?” I nodded affirmative while facing the mirror. Josh walked back out to the balcony, and I joined him a minute later. Josh put his arm around me and drew me close. “You are beautiful. I love your outfit.” “Thank you, Sir.” “Do you mind me touching you.” “No, Sir.” Josh asked me question about my sexual preferences. “Do you enjoy having sex with men?” Not wanting to insult him, I replied with ambiguity, “I don’t know, Sir. I do not have very much experience with men.” “Do you enjoy being fucked?” I responded, “My mistresses peg me. Being fucked with a strap-on is my only sexual release.” Josh followed up, “What about real cocks?” I repeated, “I don’t have much experience before tonight, Sir.” Josh’s hand moved from my waist to my ass. He traced the crack of my ass with his index finger, working his way down to my anus. Caressing my anis he asked, “What do you call this.” I responded, “My asshole.” He asked, “Do you ever call it your pussy?” I responded, “Sometimes some people do.” He followed up, “Do you mind me touching your pussy, Michelle?” I thought a moment, then responded, “No, Sir.” Asking for clarity, “Do you enjoy it.” I was clear, “Yes, Sir. I enjoy you touching my pussy.” Although other people had referred to my asshole as a pussy, it was the first time II had. Josh followed up, “Do you like to have your pussy licked?” I did not respond. Josh stepped behind me and began pulling down my panties. As he did, I put my hands on the balcony rails, stepped back, and spread my legs. My panties around my knees, Josh spread the cheeks and began to lick my … “pussy”. No one had ever licked me there. I moaned loud enough that it caught the attention of people by the pool and some of them looked up at the balcony. Josh pulled my panties back up and suggested we go inside.

I sat on the couch and there was a knock at the door. Josh was in the bathroom. I was uncertain if I should answer the door. When the person knocked a second time I got up and opened the door. It was Donna. She invited herself in. “Do you have everything you need?” I told her we did and thanked her for her hospitality. “Thank you, Ma’am” Donna ran her hand across my waist. “I love the look of corsets on people.” “Thank you for loaning it to me, Ma’am.” “Of course.” She traced the top edge of my panties with her index finger. “Will you show me your chastity device?” I responded by pulling down my panties, exposing myself. She reached down and fondled my balls. “If you didn’t have these you wouldn’t be a man at all, would you?” At that moment Josh walked out of the bathroom, and I pulled up my panties. “No, Ma’am.”, I responded. Josh joined us. Donna turned her attention towards Josh. “Josh, you have the biggest cock I have ever seen. Will you show it to me again?” Josh began to unbuckle his belt and let his pants fall to the floor. He hiked his boxers underneath his balls and enormous member fell out. “I could have sworn I heard a thud.”, she quipped. Without asking permission, Donna ran her finger along the length of Josh’s flaccid dick. “I like to watch. Do you mind?”, Donna asked. Josh answered, “Fine by me.” Then Josh turned to me and asked, “Michelle, do you mind if Donna watches us?” I was beginning to enjoy my time alone with Josh, but I answered, “No, Sir.” Donna walked to the bar, poured a glass of sparking wine, and then took a seat on a chair in the corner of the room.

I tried to ignore the presence of Donna and engage again with Josh. Following up along the themes of our earlier conversation, I asked Josh what his sexual preferences were. He replied, “I am bi-sexual, but I really enjoy spending time with feminized men like you.” I was going to object to the label, but I knew at my core that I had been indeed feminized. Josh asked if I enjoyed the role I was playing, without putting any label on it. I told him this was new to me. “Let’s experiment and learn what you enjoy, Michelle.”, Josh suggested. I nodded in agreement. Josh stepped in front of me and stripped off his clothes. He then took my hand and helped me up. Kneeling in front of me, Josh lowered my panties to my ankles, and I stepped out of them. Josh put his hand behind my hairless ball sack, pulled them away from my body. He began licking and sucking my balls. I looked down at him play with me. The corset compressed my abdomen, giving me a clear view of Josh performing oral sex on me. After a few minutes, Josh rubbed his finger across the front of the cage, licked the tip of his finger, and said, “Pre-cum. You must enjoy this.” He dribbled spit on the end of the same finger, put his hand between my legs, and he started fingering me. “You have a pretty pussy, Michelle. It’s soft and inviting.” Josh started searching for my prostrate with his finger. Finding the spot, he started a “come-hither” motion with his finger, massaging the spot. Once a rhythm was established, Josh returned to licking my ball sack. He only paused for a moment to look up at me and ask, “Do you enjoy cunnilingus?” I was becoming emotionally excited. After a few minutes of massaging me, I began to leak semen. Josh began to lick the semen as it oozed from the holes in my chastity device. I moaned and my knees felt weak. When the fluid stopped flowing, Josh stood up, put his hands on my shoulders, and drew me in. I could taste my semen on his lips. Josh stuck his tongue in my mouth. I was being French kissed by a man.

Josh picked me up like a bride and carried me to the bed, where he gently laid me down. He piled some pillows against the headboard and laid on his back. “Come here.” I crawled toward him, and he directed me to his cock. Perpendicular to him, I began to suck it. After a few minutes, Josh urged me to lay on him, in the opposite direction. I continued to work on his cock. He was positioned to lick my pussy. I felt his warm tongue work its way up the perineum to my anus. My pussy. He sucked, licked, and tongue-fucked me as I worked on his cock. He was so large. I couldn’t put more than a third of it in my mouth. It became stuck in my throat at the point where his shaft began to bulge. I felt confident that I could learn to stretch my esophagus with practice. Indeed, I felt that even during the brief time I had Josh’s cock in my mouth, I had learned how to accommodate more of it. Josh suggested I enjoyed “69”. This was the second time he referenced terms that were usually applied to sex with a pussy. First “cunnilingus” and now “69”. Josh began to stretch me. It was clear he intended to fuck me, and I wanted him to. 

Josh scooted down and tugged on me until were laying in the same direction. He rolled me over and began spooned me. I felt his hand reach down and locate my pussy. The tip of his cock followed. I felt the head of his cock probe me. Finally, my pussy let him in. The head popped past the rings like before. I relaxed and Josh cock slid inside. I felt his hips against my ass. The whole thing was in. He sat motionless for several minutes, then he started pulling it out and pushing it back in slowly, rhythmically. He wasn’t so much fucking me as making love to my pussy. I joined him in the motion, going at the same speed by in opposite directions to allow for a larger range of penetration. Josh increased the pace, and I matched his motion. He began to breath hard and a few minutes later he experienced an orgasm. His whole body spasmed. I felt his cock throb inside me as he squired cum deep in my pussy. When his excitement subsided, he did not pull out. I fell asleep with a man’s cock in me … in my pussy.

I was awakened by sunlight coming through the window. I was alone in the room. Josh and Donna were gone. I was still dressed except for my panties. I went to the bathroom and gave myself a sponge bath. I would have taken a bath, but I couldn’t figure out how to unlace the corset without help. The toilet had a bidet. I directed the flow towards my pussy and inserted fingers to help the water wash me out. I dried myself, found my panties, and put them on. Making my way downstairs, I did not run into anyone under I entered the kitchen. Donna was there. She smiled and greeted me, “Good Morning, Sweetie. Would you like some breakfast?” I was parched, so I asked for juice. As I drank the juice I asked about Anne and Monica. She said she would take me to them. She led me back upstairs and opened a door. Anne and Monica were laying in the bed. The bedding was piled on the floor, and both were naked. I motioned we should leave. In the hallway Donna showed me a video of Josh and me performing “69”. After the video played, it was followed immediately by a video of Monica fucking Anne with a strap-on. Donna intended to show me the second video. She had watched everyone have sex, and she liked people to know that she watches them. I asked where Josh was, and Donna told me he was by the pool. I told her that I wanted to see him, and she suggested I “freshen up” first. I asked her to help me get the corset off and she followed me to the room. Donna helped me undress and she offered to bring me something to wear. I thank her, draw a bubble bath, and soak for a while. I was very sore after being used, repeatedly, by four men. After bathing, I reapplied my makeup. I “kissed” a piece of toilet paper as Monica taught me to remove the excess lipstick and then found myself staring at the lipstick kiss on the paper. I was becoming a woman. I was still staring at the paper when Donna returned. “Pool time.” She handed me a swimsuit. There was practically nothing to it, a string a white bikini. I put the bottoms on. They tied on either side. I struggled tying bows and Donna helped. I reached for the top. Donna said, “Wait”, and she started rubbing and then pinching my nipples. “Men like perky breasts.” I put the top on, and Donna helped me with the knots. I looked at myself in the mirror. I noticed my white wig complimented the white swimsuit. I saw the outlines of my swollen nipples behind the shear top. The bottoms barely covered my cage and balls. Donna quipped, “The suit would look better on you if you didn’t have those.” She reached down and flipped my scrotum. That was the second time she made vailed reference to castration.

Josh was sunning himself. He was wearing a black Speedo that barely covered his cock and balls. There were two other people at the pool. I believe they were women who has attended the party. They both smiled as I walked by. Josh appeared to be asleep. I laid down in a recliner next to him. After a few minutes, he rolled over and opened his eyes. He smiled and reached across to touch me. Sitting up, he complimented my bathing suit and asked me to stand up so he could have a better look. I modeled the bikini for him. The back was just a string that ran up my crack. Still sitting on. The edge of the recliner, Josh cupped one of my ass cheeks and drew me close before kissing my cage through the suit. The two women stared at us. Josh looked up at me and asked, “Which of the experiments did you enjoy last night?” I had forgotten that he suggested we “experiment” to learn what I enjoyed. I replied, “Everything we did, Sir.” The cunnilingus?” “Yes, Sir.” “The 69?” “Yes, Sir?” “The spooning.” “Yes, Sir.” “Did you enjoy it when I fucked your pussy?” “Yes, very much, Sir.” Josh reached between my legs, pushing the string aside, he lightly touched my anus, tracing its circumference with the with the tip of his finger. I spread my legs apart to give him better access and my sack and cage slipped out from underneath the small triangle of cloth that had barely covered it. Josh quipped, “There is not much to this is there?”, referring to the swimsuit. “No, Sir.” Josh pinched the ends of the bows of string on either side and tugged them simultaneously. The bottoms fell to the concrete. “Not much at all, Michelle.” The two women were enjoying the show. Josh noticed them looking at us and he suggested we go inside. I agreed, picked up the suit bottoms, and modestly used them to cover myself as we walked by the women.

Josh took me by my hand to our room. Once inside, he asked if I wanted to “make love”. I replied, “Yes, please, Sir.” I put the bikini bottoms I had been carrying on the dresser and I untied the top and took it off too. As I did, Josh took off his Speedos. I was still facing the dresser when Josh stepped up behind me. There was a mirror on the wall behind the dresser. I noticed Josh seemed to tower over me. He took my wrists in his hands and guided my hands to the edge of the dresser, then he pulled my hips backwards until I was supporting my weight with my arms. Josh then kneeled behind me and licked my pussy while he stroked himself to erection. Josh stood up. I caught a glimpse of his enormous erection in the mirror. He found my pussy with a finger before he guided the tip of his cock inside me. Josh then grasped my hips and pressed himself against me until most of his cock was inside me. He reached around and played with my nipples, which were still sensitive from Donna pinching them. I pressed my hips backwards to force the rest of Josh’s cock into my pussy. Josh held my waist and began sliding his cock in and out. Our eyes were locked in the mirror as Josh fucked me slowly, gently. Josh seemed to be in no rush to orgasm. After half an hour, Josh was still fucking me from behind. Without pulling his cock out of me, Josh lifted me up and placed me on the bed on my hands and knees. His rhythm quickened and his breath seemed labored as he prepared to finish himself. After a few minutes my legs began to shake as I felt a new sensation. I was having an orgasm. I wasn’t like a male orgasm. My pussy was spasming and my whole body tingled. I moaned and cried. Josh sensed my reaction to being fucked and pounded me harder and faster. The sensation was overwhelming, and I let out a scream the moment Josh came in my pussy. We both shuttered and collapsed on the bed. We were both covered in sweat. After a period of recovery, Josh held our bodies close. My first thought was to get up and clean Josh’s cock, but he wouldn’t let go of me. Kissing my neck, he asked me if I would consider moving into his apartment with him. I said, “Yes, Sir.” Josh corrected me, “You mean, Yes, Josh.”