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Forced crossdressing in real life
#1
Some time ago I stumbled upon a couple of threads on Quora, where forced crossdressing was discussed. Assuming the comments are genuine, it's the "it happened in real life" what makes the subject really interesting.
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#2
Quote:One night my past wife and I were laying in bed watching TV. As usual, she had her head on my stomach and was playing with me, with an occasional lick and suck thrown in to make sure I retained my erection. After probably an hour or 2 she decided she wanted to get me off.She was playing with me and paying extra attention to sucking and licking. This was a normal thing for us. What was not normal was when she got me real close, she just stopped! OMG! I don’t remember what I said, but it probably wasn’t anything anyone could understand. She asked if I wanted her to finish me off. I probably screamed “YES” so loud the neighbors 1/2 mile away could probably hear me. She asked what I would do for her if she did. I once again screamed “ANYTHING”. She then proceeded to finish me off (probably took all of 2 seconds). After I recuperated, we switched places and I took care of her, totally forgetting what she did to me.

A few days later, she told me to go take a shower and to shave real close for a big surprise. I did as requested and, when I was done, she said she laid out my clothes for the evening. When I went into the bedroom, I saw her clothes laid out but not mine, so I called downstairs to her. She told me I couldn’t see my nose in front of my face. She came up and harassed me about not being able to see anything, that they were right in front of my face. Getting a little irritated I asked where? She said right their on the bed! The only thing I could see were her clothes. That’s when she asked If I remembered the other night and I promised her anything if she would finish me off? Guess what the “ANYTHING” was! I figured she wanted to play a sex game and wanted me dressed as a woman, so I agreed and started putting them on, including panty hose,panties, a wig, and a bra with falsies. When I was finally done, she started getting undressed and, before she could get dressed, I interrupted her progress, thinking that was her plan.

We finished and I started getting undressed. She asked what I thought I was doing? She asked me to put everything back on and she then did my hair and make up. She then got dressed and informed me we were going out to dinner. WHAT! NO F&%$ING WAY! She reminded me of my promise to her, was I going to go back on my promise? After a lot of discussion, I relented, with several stipulations, like she drove and I hid on the floorboards in the back seat and we would go someplace where we wouldn’t run into anyone we knew. Off we went to a restaurant many miles away.

I did survive the dinner without being caught. I even managed to use the woman’s bathroom at the restaurant. That was one of the most embarrassing times in my life.

After that, we did a repeat 3 times and, after that first time, it did get easier, but it still wasn’t something I would just bring up to her and say “why don’t I dress as a woman and we can go to dinner?”.

I learned that their was one upside to wearing a dress or skirt. She had complete access to me. After we got home, she ducked under my dress and had her way with me.

I should add that since she passed away, I have never done it again.
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#3
Quote:My high school was an all boys prep school. Spirit Week was filled with activities for each homeroom to compete and earn points to show their spirit. One activity was a womanless beauty pageant. It was held on the last day of Spirit Week and was a highlight of the week. There were a number of rules for contestants in the pageant, including: you had to wear a prom dress, you could not have been a contestant in a previous year, and you had to have your parents permission. Normally the moms were needed to get their boy dressed properly. Each homeroom had to have a contestant. When my homeroom teacher asked for a contestant for our class no one volunteered. Since I was small and the skinniest guy in our class, there was some pressure to volunteer. I wouldn’t volunteer and my excuse was that my parent wouldn’t approve.

A day or so later, I got home after school and my older sister was spreading some dresses out over my bed. “Pick out one that you like,” she told me. I was confused. “Mom volunteered you for the womanless pageant,” she added. I immediately went to my mom. She said that she received a call from my teacher who asked if it was okay for me to serve as my homeroom’s contestant. She talked with my teacher and it sounded like a good idea to her because I aeady had an older sister who had dresses that I could use. My mom also thought that I could be a hero to my homeroom by earning a bunch of points by winning the competition.

After dinner my mom helped me into a bra and girdle and pantyhose. Then I tried on about a dozen different dresses. My sisters served as judges and instructed me on how to walk the runway, and twirl, and curtsy. They also scored me on my appearance and presentation. Yes, everyone had a good laugh at my expense. The whole thing made me feel vulnerable and nervous. It was obvious that I wasn’t comfortable with the whole idea. So my family determined to fix this by getting me used to wearing a dress. Yes, I was instructed to dress for the pageant every day until the pageant. Practice makes perfect. My mom also had to purchase a wig and shoes (I had the biggest feet in my family).

The day of the pageant the moms starting arriving after lunch. The contestants and moms all got in the gym’s locker room. I thought I was well prepared for the event. However, my mom was surprised by how competitive some of the other moms were. They took it even more seriously than my mom! She did her best to add makeup on me, but I wasn’t wearing earrings, or any accessories. I still did pretty well. I did come in 4th place, and earned a respectable amount of points for my homeroom. My sisters were disappointed because they expected me to win the whole thing. There was plenty of talk in my family about what I should have done. My sisters were upset when they learned that I wouldn’t be given another chance. My career as a beauty pageant contestant was over.
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#4
Quote:Yes, by my two nieces one is same age as me the other is one year older. I don’t remember at what exact age it happened but we were some where between age of 12–15 if I recall correctly not sure what exact age I cannot recall if it happened more than once but if it did then it was maybe twice at max. One day when we were over at one of my nieces house they both came to me and suggested if they could dress me up as girl. I said sure as I was usually good sport when they came up with some thing fun to do. When they were done applying make up on me and help me dress in some girly clothes. I basically felt nothing towards it when they were done..when looking in the mirror what I saw was the most unconvincing girl ever…and when I analyze why: one thing is obvious of course I wasn’t wearing any hips shape forms so no hour glass figure, two the bra was stuffed with toilet paper so it felt very unconvincing on me and in mirror it did look kind off to me. I don’t remember if I was wearing any wigs, but if so they must have given that to me…since it was not my own hair it did look fake…but if I wasn’t then some was obviously missing from completing the final look. But there might have been other reason why this didn’t do anything for me. When I was young I always disliked cosplay not seeing other doing it but doing it myself, back then Halloween was not thing in my country and kids in 1980s and 1990s kids did not dress up back then. We on the other hand had day called Ash Wednesday where kids did dress up in various costumes and basically go trick an treating around the town minus the spooky part of Halloween. (Halloween did not start getting some attraction attention until after I became an adult although kids in my country now have started to cosplay for Halloween also.) But back then I always disliked dressing up in costumes and pretend being something or someone I’m not so that might be another factor why dressing back then up as girl with help of my two nieces didn’t do anything for me in the end minus the lack off some seriously realistic requirements to make a convincing girl. I must admit sometimes i wonder what might have been if we had some proper widgets back than such as quality wigs, breast-forms and shape-where and proper makeup skills but since I don’t care about cosplay and cross-dressing to pass ass the opposite sex is nothing but a cosplay in grand shame of things and whole lot of pretending thus I doubt that will ever actually happen.
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#5
Quote:Yes, a girl who was 2 years older than me asked me if I was going to the fall dance. At that time I was full of myself and loved teasing girls and being rotten to them. I told her I would if I had a date. She said she would find me a date but I had to do everything she wanted. I agreed thinking I had a chance with her. A couple of weeks later she told me she had everything ready to go. She picked me up and we went to her house. One of her friends was there and before I knew it I was dressed as a teenage girl. I still thought she was my date until I was led to the living room and there three guys in tux's. She told me now I would find out what it was like being a girl 😞
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#6
Quote:Was caught by my mother with several cheap bras from Wal-Mart when I lived at home. I didn’t know it at the time, but she came downstairs and shoved them in my face and asked where they came from. I told her I bought them and she was mad. Later that evening, she came into my room with a pink bra and make me put it on. I had to wear it all night sleeping and then she was going to make me wear it to school as well. However, she had me take it off the next morning for some reason unknown. That was the only time I was forced to do something

Quote:My brother when he was 8 was put into lingerie a dress and makeup and had his hair curled by my mother after he was caught wearing my petticoat and skirt. He was suppose to wear it as a punishment for a day, but at the end of the day he wanted to keep it on, so mother let him wear dresses around the home.

Quote:This is how I got started crossdressing. It started with my sister wanting to give me make overs when we were barely teenagers. It was fun, but at first I didn’t want to keep doing it. She rather enjoyed doing it, and threatened to tell our mother and father if I didn’t let her continue. It escalated to wearing her clothes, and jewellery. By this point I was getting addicted, and I gotta admit, I really got off on being very submissive to her (I still would, but life has moved on)
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