When I was 21, I had a one-night stand with Imelda, a young Latino woman. Imelda was the first dominant woman I had been with, and that evening she used me for her pleasure and amusement, before discarding me in the morning. Imelda was also the first person to play with my ass. Although I was naive to the concepts then, while sitting on my face, she edged me. She did not allow me to fuck her and instead milked my prostate. She further humiliated me by forcing me to swallow urine, taste ass, and eat the semen she had milked from me. I never mentioned the incident to anyone, and embarrassed, I successfully expunged it from my conscience for more than a decade, until through a “chance” encounter, Imelda and I met again.
Rooting through the fridge in a convenience store, I found my beverage of choice. As I stood up from a crouching position and closed the door, I saw the reflection of someone behind me. Thinking I was in their way and without turning around, I instinctively apologized and tried to step aside. As I began to move, there was a tug at my waist. The person had stuck a finger in a belt loop and used the purchased to spin me around. Although significant time had passed, I recognized Imelda. Perhaps a foot shorter than me, my first thought was she looks smaller than I remember her to be. I wondered how I could have let her bully me the way she had that night. Before I could say anything, she offered, “I was thinking about you the other day.” It seemed like an odd thing to say as we had not communicated since our only previous encounter. It was at that moment that I realized she had sought me out.
Imelda explained she had enjoyed our “fun”, as she put it, was hosting a party this coming weekend, and she wanted to invite me to attend. While processing my feelings about seeing Imelda again, thoughts of our first encounter flooded my mind. Before I could respectfully decline, Imelda “accepted” the invitation on my behalf. I subsequently tried to formulate an excuse for declining, but only mumbled an inarticulate word salad and she responded, “my party will be much more fun than your other plans.” She then tugged on the collar of my shirt to bring my ear to the level of ear and whispered, “I will pick you up at 8:00 on Saturday” “Wear something nice.” As she started to turn to leave, she remembered “Oh, do you live at the same place?” The word “yes” passed by lips; my single-syllable response sounded like consent. Imelda turned and walked away, leaving me wondering what I had agreed to.
My anxiety grew as the weekdays passed. Precisely at 8:00 on Saturday, there was a knock at the door. Practically paralyzed, I had procrastinated getting dressed, so I found myself standing in my living room in my underwear. I began to sweat and I grabbed a pair of pants to cover myself as I stumbled my way to the door. Pausing at the door to collect my thoughts, a second, more forceful round of knocking was heard, and I opened the door. I stood before Imelda half-naked as she threw me a disapproving look. Without speaking, she placed her hand on my bare chest and pushed me backwards as she stepped through the door. “You appear to need some help getting ready. Take those pants off”, she commanded. “They are too casual.” I offered no resistance and my pants fell to the floor. Imelda stepped behind me, grabbed the elastic waistband of my briefs, and tugged them down to my ankles. “Let’s start from scratch. Stand there, in the light”. Correcting me, she commanded “Stand up straight.” Stiffening my spine, I stood at attention before her. She looked down at my groin and smirked. “It is smaller than I remember. Actually, I find your tiny penis a bit offensive.” I cowered in shame and covered my genitals with my hands. I thought my penis was average, certainly not “tiny”, but it had shriveled under the circumstances, making it appear smaller than it really is. “We’re going to need to get you cleaned up before you’re dressed.” “Come with me”, she ordered, as she made her way to my bathroom.
I hadn’t noticed, but Imelda was carrying a small black leather bag. Once in the bathroom, she told me to stand in the tub, facing her, with my legs spread. As I complied, Imelda reached into her bag and withdrew a pair of cordless electric hair clippers. Standing in front of me, I was in shock when Imelda reached down and grabbed my genitals, both the penis and the testicles, with her free hand as she flipped on the clippers that she was holding in her other hand. Going to work on my pubic hair, she started by shearing the mound of hair above my penis, then pulling my genitals alternately to the left and right, she did the sides before pulling up and shaving beneath my testicles. Stretching out first my penis and then the loose skin of the sack, she quickly removed the last of the hair before commanding me to turn around, bend over, and touch my toes. As I complied, I felt her spread my ass cheeks as she shaved the hair around my anus. Standing erect, I saw myself in the mirror. My face was beet red. Imelda reached down to the tub faucet and twisted one the handles. Without waiting for the water to warm, she turned on the shower, grabbed the detachable shower head, and began hosing my down like an animal. I looked down at my hairless genitals. They looked juvenile. My penis looked even smaller. Shame kept my eyes directed at the ground. Tossing me a towel, she left the bathroom and walked to the bedroom. I knew to follow.
Imelda opened my closet and selected a pair of slacks, a dress shirt, a dinner jacket, and a pair of black leather shoes. She laid the clothes out neatly on the bed. Expecting to dress, I was taken aback when she told me to lay down, face up. I complied and she set her black leather bag down next to me. “Let’s start with the basics” she said, and she withdrew something shinny from her bag. I could hear disassemble something, I then felt cold metal in my groin. “I am going to cage you for the party tonight.” “There will be a lot of young women there, and I don’t want you to get any ideas.” Before I could protest, my genitals were locked in a chastity device. I complained “It is too tight.” Imelda simply put her finger to her lips signaling me to be quiet. I asked her if she would remove it after the party, but she did not respond to the question and instead said “now for undergarments.” I thought it an odd choice of words until she withdrew a pair of frilly panties from her bag. “Put these on, and then the rest of your clothes.” “Quickly.” “We are late.” Imelda left me to dress myself.
After dressing, I found Imelda standing by the door with her bag in her hand. “Do you have a phone with you”, she asked. I took my cellphone from my jacket to show her, and before I could put it back, she snatched it from my hands and placed it on a shelf. “You won’t need that.” “We’ll take my car.” Riding in the car, she asked me about my sex life. She wasn’t interested in my love life. Rather, she wanted to know if I was having sex. I simply responded “yes”, but she wanted details. “With women?” “Yes” With men? “No” “Often?” I did not know how to respond to that question. She wanted details. I explained there were three women I had sexual relationships within the past couple of years. I told her how often we had sex. At her insistence, I provided details of the sexual encounters, which could only be described as vanilla. She asked me if I had every worn a cock cage. “No” She asked me if I had ever worn woman’s clothing. “No, not until now.” She asked me if I had ever been fucked. I was confused by the question, but she did not clarify.
I took about half an hour to drive to her house. I had not paid attention to the route, but it was clear we were outside of town because she had no neighbors as far as I could see. The house was offset from the main road by perhaps a quarter mile. When we pulled up to the house, we passed several cars that lined the road. She clicked open her garage door and parked the car. Stepping out of the car, Imelda motioned me to follow her inside. The entrance from the garage led through the kitchen. I noticed hors d’oeurves neatly organized on trays and I heard music and people talking in the next room. As we walked into the living room, the conversations paused, and everyone in the room looked at us. There were eleven women, twelve with Imelda, and I was the only man. I heard one of the women in the back say under her breath, “Ah, the entertainment is here.” “Ladies, this is Michael. He will be serving us this evening.” Imelda then turned to me and said, “You don’t mind do you?” “Be a gentleman and bring my guests some refreshments. You’ll find everything you need in the kitchen. Realizing I hadn’t really been invited to the party, but rather just solicited to help serve the guests, I retreated to the kitchen.
I might have left the party to return home, but I didn’t actually know where I was, I had no transportation, and without my cell phone, I couldn’t call for a ride. As I walked to the kitchen, I could feel Imelda following me. Once in the kitchen, she presented me with a shear apron. “We don’t want to get your clothes soiled. Put this on. You can leave your undergarments on as well.” I looked at her confused and she clarified, “Take everything off except your cock cage and panties and put this apron on. When you’re ready, start by serving some sparkling wine.” I hesitated. There was no way I was going to serve a bunch of women dressed like a sissy. Imelda initially scowled, but then her expression softened to a smile. “My apologies, we should have discussed these matters before the party.” I let my guard down and prepared to explain that I was not comfortable exposing myself to her guests. She nodded, seemingly agreeing that her expectations were unreasonable. Placing her hand on my arm, she gently turned me away. Thinking perhaps she was going to return me home, I began to step forward. Before I took the first step, Imelda exhibited martial art skills, pulled my arm behind my back and pushed me forward towards the island in the middle of the kitchen. Off balance, I fell forward. With my legs back away from the island and now both arms behind me, I heard the distinctive sound of handcuffs clicking around my wrists. I wanted to roll around and stand up, but Imelda held onto the handcuffs. I felt her hand reach around to my belt, and a moment later my pants were about my ankles, further hobbling me. “Positive attitudes will result in a positive experience tonight. Negative attitudes will not.” Opening a drawer in the island with one hand while pulling my arms in the air via the handcuffs in the other, Imelda fumbled around until she found the tool she was looking for, a heavy wooden spoon, She commanded, “Count for me.” My face pressed against the cold marble of the countertop, I noticed three women had stepped into the kitchen to observe my punishment and I heard the rest in the next room giggling. Wack! I had never felt such pain on my backside. Leaning down once again to whisper in my ear, “That one did not count because you did not count it off.” Wack! “One!” Wack! “Two!” Wack! This continued until struck me eleven times, ten plus the one that did not count. The panties I was wearing offered little protection from the blows. My eyes watered.
Having witnessed the punishment the guests returned to the living room, leaving me alomne once again with Imelda. While I laid limply across the top of the island, Imelda reach down to removed my shoes and my socks, then she removed my pants that were still around my ankles. Imelda reached back into the drawer and produced a pair of scissors. She stepped within my view and began to cut the pants into pieces, as if to make clear to me that there was no going back at this point. After rendering the pants unwearable, Imelda stepped behind me as I still laid chest-down on the kitchen island, and she began to work on my dinner jacket, cutting it away like I was an injured patient in an ER. She didn’t bother with the scissors for the dress shirt and instead pulled on it from behind until the buttons have way, then she nicked the shirt in a few places with the scissors and tore the shirt from my back. Wearing nothing by the panties, a chastity cage, and the handcuffs, she stood me up and asked a simple question. “Will you comply?” I nodded “affirmative” while staring at the ground.
The handcuffs removed, Imelda handed me the apron. Putting the apron on, I felt an odd sense of relief that I had something to cover myself before assuming my responsibilities to serve the guests. That relief was of course unfounded as the sheer apron left little to the imagination. I took two bottles of champagne from the refrigerator, opened them, and poured twelve glasses. Being inexperienced at serving, I placed six at a time on a tray and bought them to the women. I could not look the women in their eyes as I served them, but I could tell they were of similar age, early thirties. They represented different ethnic groups. They all wore party dresses. As I handed out the glasses, I could sense they were smiling. More than one woman giggled as I served them. As I returned to the kitchen to fetch the second tray, they saw my backside and I heard whispering and outright laughter. My hands shook as I returned with the second tray. After the first round of drinks were served, I returned to the kitchen to fetch trays of hors d’oeurves. By the time I returned with the food, the women were once again conversing with one another. They hardly seemed to notice me, which was a relief as I could focus on my duties serving. Focusing on the work took my mind off the embarrassment of my attire … and the cock cage. As I was serving the third round of drinks, I felt a hand caress my butt cheeks. Slipping her hand underneath the panties and rubbing my butt, the woman leaned over my shoulder and said “That spanking left marks, Sweetie.” She traced the outline of the welts with her fingers. With her other hand, she tugged at the strings of my apron, loosening the knot and causing the apron to fall to the floor. Still holding the tray of drinks, I lacked the coordination to retrieve the apron. No longer wearing the “shield” that afforded some modicum of dignity, I now stood there wearing nothing but the pair of frilly panties. Although only Imelda had seen the cock cage up to now, the panties clearly revealed the outline of the cage I was wearing. The woman who undid the apron strings reached down, picked up the apron, and slung it over her shoulder, wearing it like a prize.
As I turned around to return to the kitchen, I heard Imelda’s voice behind me, “One second.” She pulled the panties down around my ankles and I stepped out of them so as not to trip. Facing away from the women, I raced back to the kitchen where I pondered my fate. Embarrassment paralyzed me. I couldn’t return wearing nothing but the cage. As I sorted out my few options, Imelda stepped into the kitchen and asked why I had been delayed. I asked her to show me some mercy, but she only laughed. “Actually, you don’t need to serve any more. Come with me.” Leading me by the hand, the women watched as I was paraded by them wearing nothing but the cock cage. They all laughed as Imelda explained that I felt embarrassed and wanted to put some clothes on. We walked down a hallway and into a bedroom. It did not feel like the master bedroom, but like a guest room. There was strange art and photographs on the wall. One wall was completely covered by 8×10 photographs in frames, perhaps twenty of them. The photographs were all similar in appearance, standing portraits of women in strange frilly dresses. “Let’s find you something to wear.” Opening the doors to a closet, Imelda started rummaging through the clothes that were hanging in it. Off to the side, I could not see what was in the closet, so I was shocked when she pulled out a dress. “This should fit you.” Standing next to the wall of portraits, I looked more closely and realized the photographs were of men who were dressed like women. I began begging her to let me wear something “normal”, but she said had nothing else for me to wear, and if I wanted something to wear, this was all she had that would fit me. Knowing that the clothes I had worn to the party had been destroyed, I felt I had no option but to wear the outfit, as I simply couldn’t return to the party wearing nothing but the cock cage. She began laying items on the bed: a pink taffeta dress with white piping, a pair of white lacy panties and matching bra, white stocking and a garter belt, and pink silk ballerina slippers. She also laid out a blond wig. “Sit on the edge of the bed.” “Let’s work on your makeup.” She began applying makeup to my face: foundation, blush, mascara, and finally lipstick. During the ritual I was numb, paralyzed, and unable to speak. Accepting that I was going to serve the role of a clown, I sat still as Imelda worked on me. When she finished applying the makeup and arranging the wig. I stood up and looked in the mirror. I did not see myself. Someone else stood there. She handed me the panties and I slipped them on. The same with the stockings. Imelda helped me with the garter belt and the bra. The bra had some padding to make it appear that I had breasts. Finally, I slipped the dress over my head and Imelda helped me button it from behind.
Standing me against a blank wall, Imelda took out a camera and said “smile”. I produced the same face of horror that I now realized everyone wore in the photographs on the wall. Strangely, on second thought, I was in fact more embarrassed by these garments and the makeup than I was of being naked. Walking back down the hallway, I noticed the guests were no longer conversing. Entering the living room, I found the women were mostly naked. Some were kissing and caressing one another, and the others watched as I was put on display. Even the women who were making out looked up to see the “art” that Imelda had created. They all smiled and many nodded in approval. Imelda sat me on a stool at the side of the room. Most of the women went back to making out. Imelda explained to me in hushed tones that I would have new responsibilities for the remainder of the party. I was to be the “whore”. My lips quivered as I asked what that meant. Imelda explained, “You will use your tongue and your holes to service my guests. This is a whore party and you’re the whore. Any sexual service my guests ask for, you will provide. Let’s start with me. You remember how to worship my ass, don’t you?” Imelda began to strip off her clothes. When naked, she leaned against the wall and spread her legs. “Get to it, Whore. Lick my asshole.” I flashed back to a decade earlier when Imelda had degraded me in the same way. But, it was private sex then, and now we were in public. Feeling powerless, I kneeled behind her. She reached behind as I did and pushed my face between her butt cheeks. and she began rubbing her ass on my face. “Show me some tongue or I’ll kick you in the balls.” I licked her anus. It was musky. It did not taste clean. “French kiss my asshole, Whore.” I hesitated, not knowing what she meant. “Tongue fuck my butt, Bitch.” I did my best to put my tongue inside her, but her anus was tight. Seemingly frustrated, Imelda dragged me to the ground, sat on my face and stated thrusting up and down. I curled my tongue to make it more rigid. Eventually her muscles relaxed and my tongue entered her. She fucked my face until she was satisfied. When she finally stood up, I realized the other eleven women had stopped what they were doing to watch Imelda humiliate me.
“Let’s fix your makeup.”, Imelda said as she took me by the hand and led me back to the room where I was dressed. Wiping the makeup from my face, she carefully reapplied it and said “You’re much prettier now,” Grabbing my cock cage, she pulled me to my feet, turned me towards the door, and slapped my bottom, as if I were livestock being herded back to the party. To my horror, I entered the living room to face eleven naked women wearing strap-ons. I couldn’t process what that meant. Was it going to be some lesbian orgy? Why was I there? Imelda’s hands were still placed on my shoulders, and she pressed me to the ground, in a doggie position. Walking around me, she kneeled in front of my head, stretched out my arms, and pinned my wrists to the carpet. The women behind her began to file in behind me. Their plastic cocks bobbed as they walked past me. The didoes were larger than my cock. They were in fact enormous, larger than a normal man’s erect penis. Larger than porn stars penises. The plastic phalluses were all shinny and black. Most had fake veins or ribs. I knew my fate. Imelda leaned down and said “relax” as the first woman in the pegging train kneeled behind me. Lifting the dress, she pulled the panties I was wearing. While rubbing her “cock” against my anus, she said, “What a pretty boy pussy.” I heard her spit, then she started probing my ass. At first, I must admit, it was pleasurable to have my anus caressed by the dildo. But, as she began inserting it, I panicked and started bucking. I pleaded to no avail. I saw in my periphery, two women step out of line and join Imelda to hold me down, one to my left and one to my right. Imelda held my arm in front of me and the other two women pinched my shoulders to my knees, causing my ass to rise into position. This was not the women’s first rodeo. The person behind me did not hesitate once I was constrained, and she pierced my rectum in one thrust. I screamed in pain. Imelda’s response was to stuff something in my mouth.
Later, I realized what she put in my mouth were the panties I had been wearing. I recognized them only after they were removed my mouth and replaced with a dido. The dildo did not taste of plastic, but rather of fecal matter. One of the women had pegged me and then forced me to clean her dildo with my mouth. After that, being fucked in both my holes became routine. It was a fuck train. A woman would fuck my ass and then step forward for me to clean the dildo. After three or four women, Imelda let go of my arms and the women who flanked me joined the line. I was a wore. I was there to amuse the party guests. Twelve dildos in my ass. Most of the women pegged me for 10-20 minutes, long enough for most of them to experience an orgasm. Doing the math, my asshole and my mouth were used by them for almost three straight hours.
Imelda was the last woman to peg me. Before she penetrated me, she flipped me over onto my back. Pushing my knees to my chest and grasping and pulling on my caged genitals, she smiled as she put her plastic dick in me. My gaping anus offered no resistance. The other women stood in a semicircle behind her, cheering her on, some clapping in rhythm with the thrusts. One of the women stepped past Imelda and stood over me, straddling my head. I thought for a moment she was going to sit on my face, but then she started urinating on my face. I tried to move my head out of the stream, but she dropped to her knees and pinned my head such that my mouth was directly below her urethra, I closed my mouth, but she stopped peeing and held my nose until I was forced to open my mouth to breathe. I chocked as the warm salty fluid flowed into my mouth. When she finished urinating in my mouth, she pressed her wet pussy against my mouth and ordered me to clean it. I complied. After a moment she changed her position, pressing her asshole to my lips. I knew what she wanted and offered no resistance. After the first woman was done, most of the other women took her place, while Imelda continued to fuck my ass. I had never been with more than one woman at a time. Tasting all these women in turn caused me to realize that they all tasted different. Their urine, their vaginas, and the anuses had unique smells and flavors.
Imelda stopped fucking me as the last woman finished with my face. Imelda then took her place and I served as Imelda’s toilet. When I has finished cleaning her, Imelda handed me the dress I had worn earlier in the evening. I looked up at her and she said, “We don’t have your clothes anymore, so I suppose you will need to wear the dress home. I’ve called up an Uber.” Smelling of urine and feces, I asked if I could clean myself up. Imelda replied, “You can do that when you get home.” She then escorted me past the sated guests to the front door. “You can wait outside for your ride. Thanks for coming to my party.” As I stepped outside, I realized I was only wearing the dress, no underwear, and I was still wearing the chastity cage. The short dress barely covered my groin. I knocked on the front door to ask for the cage to be removed, but the only response was the porch light being turned off.