From the first time my girlfriend Sandra and I had sex, I knew she had strange urges. Her sadistic tendencies were evidenced in subtle ways at first. Early in our sex life, she enjoyed pinching my nipples when we fucked. The force applied would increase the closer I came to climaxing. Before long, she was leaving marks, including scratches and small bruises. Sandra would often ask to see the marks the day after we had sex.
A few months into our relation, Sandra began introducing humiliation into our day-to-day sex. The first time she spanked me was after we had conventional sex. We were lying naked in bed when she rolled over and started rubbing my butt, then patting it, and before she was finished, I was on my knees with my face planted in a pillow and my ass and she was full-on spanking me with her open hand. An hour later, she asked me to drop my drawers to admire her handiwork.
The pain and humiliation escalated over the coming months. Whenever we fucked, she’d have me wear a cock ring with a bell that rang as I copulated. She also introduced cock-and-ball torture. She liked to squeeze and slap my balls. Once she bruised them so bad that were bright purple. The discoloration excited her, and she made me shave my pubic hair so she could get a better look.
One day she came home with a strap-on. Without a word, she showed it to me. Later that night she used it for the first time. I had never been penetrated before. It was both painful and humiliation. She knew I did not enjoy pegging, which I believe was in part why she liked doing it. While initially, the strap-on was used in our bedroom during sex. Later she would fuck me different places in the house as a form of punishment. We once went camping and she pegged me in an open field while I laid across a fallen tree.
After about a year, she would have me wear panties when she wanted to spank or peg me. Later, she would have me wear a frilly nightgown. I hated these acts of feminization. When I worked around the house, she started asking me to wear different uniforms. For example, in the kitchen, she asked I be naked except for an apron. When vacuuming and generally cleaning, she asked me to wear a black dress that was so short that my penis was visible.
All the time that she was upping the ante with respect to feminization, Sandra also stepped up the punishment. She started using a paddle instead of her hand to spank me because she could hit me harder. Then she started using a cane because she liked the stripes of red and the ridges of swollen tissue the cane produced. She loved passing her fingers over the welts. Once she took me to a public restroom inside an art gallery during a reception and spanked me. A line had formed in the hallway as people waited to use the restroom. When we left, I am pretty sure some of the people understood what had happened.
Emboldened by this almost-public exposure of her kinky sex, Sandra started talking about exhibitionism. Once in a Walmart we were checking out and she produced a box of extra small condoms. When the woman behind the register picked up the condoms, Sandra pointed at me and said while wiggle her pinky “He has a little dick.” Both laughed. It was the first time she had purposefully humiliated me in pubic. In a related incident, while shopping for groceries, she sprayed my crotch with water using a squirt bottle she had obviously brought for that purpose. For the rest of the excursion, I was forced to walk around with sodden trousers, as if I had peed in them. Another time she asked me to pee in my pants while in public. I refused to do it, and she punished me when we got home.
Public humiliation became more common after these incidents. At a dinner party once, the subject of kinks came up. Sandra offered that I had a small penis humiliation fetish and I “loved” wearing knickers. She also suggested I would probably enjoy licking her out after another man has come inside her. The other guests laughed, and I was mortified by her revelations. This was also the first time she suggested having sex with someone else.
Shortly after to dinner party incident, Sandra started flirting with other men. The next incident occurred at a bar. Sandra chatted up the guy that was sitting next to her while I was sitting on the other side. I was shocked when she asked for his number, and he gave it to her. I was even more shocked when at home she told me to go down on her while she sexed the guy. She read out loud the messages that were exchanged as I licked her.
Sandra: This is Sandra, the woman you gave this number to at the bar tonight. I wanted to tell you how hot you looked. I would love to know all the terrible things you would want to do to me.
Dude: Well, I think I would have you walk through the door, then push you up against it and pin your hands above your head as I kiss you. Use my hands to feel all over your body and take off your clothes. Then put you on your knees and put my cock in your mouth while I grab your hair. Then take you to my bedroom and eat your pussy. Gently using my teeth and sucking on your clit while I use my fingers.
Sandra: Yes please pin me down and have your way with me. I would love to show you how good I can make you feel while I shove your cock down my throat and cup and play with your balls.
Dude: The sounds fantastic. What else would you want me to do?
Sandra: I’d like you to fuck my pussy, but before you cum, I’d want you to stick your cock in my ass.
Dude: I can imagine sliding my cock in and out of your dripping pussy right now. And, now I am fucking your tight hole. Where do you want me to cum?
Sandra: I want you to cum in my mouth, and I want to suck your cock dry.
At this point Sandra had a massive orgasm. When she finished, she started texting again.
Sandra: I just had an orgasm while my husband was licking my pussy. I have been reading your texts to him.
Dude: That’s wild. Is your hubby one of those cuckolds?
Sandra: Maybe. You want to be my bull?
Dude: That would be cool. Would he let me fuck you?
Sandra: It’s not really up to him. You should fuck me and he can clean up the mess.
Dude: What does that mean?
Sandra: You can fill my pussy or ass full of spunk and he can lick it out of me.
Dude: That’s nasty, but I’m game.
Sandra: I’ll meet you at the bar on Saturday at 6. Goodnight.
Dude: Nite Nite
Sandra passed me her phone so I could read the messages. I asked, “Are you really thinking about fucking this guy?” Sandra just smiled. The subject did not come up again. Saturday came and went. It seemed that the whole scene was an effort on her part to humiliate me.
About two weeks passed, and Sandra blindsided me with a suggestion that we visit a sex club. Living in the Bible Belt, there were no such clubs in our state, but she had done her homework and had an actual date at a BDSM club in Colorado. I thought she was kidding, but she wasn’t. She asked me to make the arrangements for the flights and local accommodations. I booked the flights and the and a motel room for the date, about five weeks away.
As the date approached for our trip to Colorado, Sandra started preening me. She arranged for me to visit a salon where my hair was cut, and I received a manicure and pedicure. I was beginning to feel pampered. Two days before the trip, Sandra arranged for me to “get cleaned up.” I didn’t realize what she meant by that is my body hair would be removed with wax. Looking at myself in the mirror afterwards, I felt like a juvenile.
The plane trip to Colorado was uneventful. We arrived mid-day and settled into the motel room. After getting a bite to eat at a Mexican restaurant, we returned to the hotel room to get ready to attend the session at the club. When we arrived at the hotel, Sandra handed me a Fleet enema and told me to “get cleaned up.” I retired to the bathroom and did as she said. As I was cleaning my bowls, I thought to myself that she intended to peg me. After the enema, I took a shower. When I came out, Sandra was dressed. She was wearing an outfit I had not seen before. It was black and tight-fitting. She held up an article of clothing that were apparently for me. It was feminine, but different than the nighty that she had me wear before, a black corset.
I protested, but she insisted that I try the corset on. Standing behind me in a full-length mirror, she tugged at the string that cinched the garment tight. My torso had an hour-glass shape and the skin on my chest was pushed up making it look like I had breasts. From the neck down, my hairless body could be mistaken for that of a woman, if not for my exposed genitals. Smiling at my appearance, Sandra went into the bathroom for a minute and returned with a handful of makeup. She applied gel and slicked my hair back, mascara, a foundation and blush, pinkish eyeliner, and bright read lipstick. This was the first time I had worn makeup. When she finished, she produced a pair of black silk panties and helped me put them on. I stared at myself in the mirror. I was no longer a man.
Sandra ordered an Uber and informed me when it arrived. As she approached the door, I asked her what I was supposed to wear. Her response was, “You have it on.” The Uber pulled up in front of the motel room door and I hid behind the door as Sandra grabbed her belongings and got in the car. Motioning for me to join her, I ran over hoping no one would seem me. Just as I approached the car, Sandra closed her door and motioned for me to go around to the other side. I could see there was a woman behind the wheel as I got into the backseat behind her.
We arrived at the BDSM club about twenty minutes later. When the car stopped, the driver got out to open my door, but it was obvious she just wanted to get a better look at me. She giggled. I made my way to the front door of the club knowing with some relief I would not be the only person dressed in such a costume. After checking in at the front desk we joined a group of perhaps forty people who were already gathered in the large, main room.
Shortly after we arrived, Sandra pulled my panties off me and put them in a bag she was carrying. She purposfully exposed my genitals to the other guests. As we mingled with the other guests, Sandra introduced me by the fictitious name Ruby. We stopped at several “scenes” where people were being flogged, tied up with roped, and treated like pets. I noticed while there were other feminized males at the club, I was the only one who had his penis exposed. This was the first time in my life I had been exposed to strangers.
After about ninety minutes, Sandra told me it was time for our scene. She led me to a piece of BDSM furniture, bondage stocks that clamped down around my neck and wrists leaving me in a standing position, albeit bent over at the waist. Leather straps were fastened around my ankles causing my legs to be spread apart. I could feel my penis and scrotum dangling in the air. People started gathering around as Sandra secured me to the stocks.
Sandra started with a leather strap. I had never been in bondage before and couldn’t move an inch as she struck my ass. After a few dozen blows, my butt was on fire and I begged her to stop, and she did, but only for a minute as she selected a different weapon, a cane. Tapping it first against my right cheek to take aim, she struck me three times. Each time I yelped in pain. Then she moved to my left cheek and duplicated three blows. She repeated this three times until a total of nine blows were delivered. By the time she finished, I was crying.
Sandra stepped in front of me to see the tears and the pink eye shadow that was flowing down my face. She had a whip in her hand. I did not even know that she owned one. It was braided leather and was terminated with a cracker. She snapped it twice in the air before stepping behind me. I heard the whip crack twice more without striking me. The third time it hit my right butt cheek. I had never felt such pain and screamed out. Before I could speak, she struck me three more time, a total of twice for each cheek. I was wailing, unable to speak. After a moment’s rest, she struck me four more time before I could plead for her to stop, which she did.
I sat in the stocks about five minutes trying to gather myself when I felt Sandra touch my ass. She was tracing the welts left by the cane and the whip. I could tell the difference. The marks left by the cane were horizontal. The marks left by the whip were vertical. As she traced the vertical welts, they felt slick and wet. She had drawn blood.
I expected to be released, but when I was not, I knew she was not finished. She spread my ass cheeks. It was painful when she grasped them in her hands. She was examining my anus. She was going to fuck me in front of forty people. She let go of my butt and I felt the tip of her cock pressing against my anus. She pushed it in with one thrust, without allowing me to relax. It was painful, but not as painful as the cane or the whip. When she started fucking me, it was relatively pleasurable, except when she met my raw skin. People clapped as my ass was publicly violated. After about ten minutes, Sandra experienced an orgasm. It was the first time she had experienced one while pegging me, evidencing her excitement as a result of hurting and humiliating me in public.
Sandra released me. I asked to leave, and she ordered an Uber. Just before it arrived, she handed me my panties and I put them on. When the ride arrived, I could see it was the same one that had delivered us. The driver got out of the car to open the door. She wanted another good look at me. Before I sat down, she asked me to wait a second, and she got a towel out of the trunk. She didn’t want blood or other body fluids on her upholstery.