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The idea terrified me. I did have a girl friend in 7th grade for a total of two hours!This continued in high school. I went to a good private high school. I played multiple sports (not good in any of them), got good grades, and did a ton of activities. But I still had no luck with the ladies. I had two sets of friends; my high school friends and my neighborhood friends. My neighborhood friends didn’t know I had no luck with the ladies so it occurred to me to lie to them. I started telling all. My bf went deeper than he had ever been with me. Making my eyes water. They stung from the make-up running into my eyes. He pushed down deep and hard making me hold him all the way down my throat, I was making little gagging sounds as everyone cheered him on to keep it deep. Then he pulled out and said “That’s how I want it done boys except I want you to be as rough as you can with her pretty little mouth. What are you waiting for? Line up, come on!”About 10 or so guys lined up straight away.. After a few minutes and he lifted up my dress and took it off over my head, my chub was hanging down over my white knickers but I didn’t care I was too turned on.We carried on kissing as he unclipped my bra my 42DD tits swung down and he fondled them my nipples getting harder by the second. Then the door slid open and as I looked two other lads got in and shut the door, as Josh and I were kissing he said “These are my brothers” as he pointed he said “He’s Jake and he’s Steven” I smiled.Then. Like most crossdressers, for most of my adult life I have had the urgeto dress-up as a woman for short periods of time, and I often used todress in my wife's underwear when she was away on business. Since thedivorce some two years ago, me, Michael, the respectable businessman,likes to transform into Michele, the sexy secretary (or naughty nurse;or whatever takes my fancy at the time) whenever it pleases me to do so.Living alone, and having the privacy to dress when it suits me, I havespent many.
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