1. Crossdressers first time


    Date: 3/9/2015, Categories: Fetish, Gay Male, Shemales, Author: Missterious999, Rating: 95, Source: xHamster

    So let me begin and say this is my actual first time of being dressed in front of someone and my first time with a guy. It all started when i was 21. I was in college but on christmas break and my friend pat was having a party. Living only 5 minutes away i said i would go. Party was small 5 guys and 3 girls there. The girls were getting bored after a while and were going to leave but they started whispering to each other and said lets play truth or dare. With all the guys desperate to not let this party turn into another guys night we all agreed to play. It started out typical all the girls picking truth only asking sex based questions to them. After a few rounds nobody had yet to pick dare then we decided to draw cards. Lowest 2 had to choose dare to liven up this boring game. I got one and so did alycia. Alycia was the first dare. She was dared to make out with one of the guys which she did. My dare was blindsiding out of nowhere. One of the girls dared me to dress up as a girl ! I was reluctant and put up a small fit about it but eventually gave in. The guys all thought this was hysterical. Pats parents were away for the weekend and the girls took me upstairs to his parents room where i would be made into a girl using pats moms clothes. At this time i was about 5'6 and couldnt have weighed more then 140 pounds which was very close to his moms size. After i had realized that this wasnt going to be a quick makeover i decided to have fun with it. I stripped down to my ...
    boxers and the girls picked out some underwear for me and said we will turn around while you put them on. It was quite a skimpy thong that was pink and had lace trim on it with a matching bra. I felt humiliated when they turned around even more so due to some tenting in my panties. They all had a good laugh. Then i tried on 3 different dresses and heels for them which at this time i was very much enjoying the whole experience when the guys yelled up to us hurry up already. The girls then decided it was to formal to wear downstairs and they had me put on a denim mini skirt whit a white cami and a pink top to got with it they made me wear some black strappy sandals with a small heel. They did makeup on me in about 5 minutes flat and i was ready to go except for my hair. I have very short black hair which they could do nothing with so they yelled down to pat does your mom have a wig or we have a butch up here. He looked around his basement and found a old one from several halloweens ago. It was a short blonde wig cut into a bob haircut. They put it on and said what so you think. Looking at myself in a mirror i actually looked like one of the girls. I told them it looked good and laughed. As we came back downstairs sarah gave me a kiss and said dont do anything we wouldnt do. I was shocked. Having a crush on sarah for years and she just kissed me as im dressed up like a girl. So as we got downstairs the guys obviously were laughing but not jokes were to bad. Until someone said i see ...
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