[MM] How I became my roommates sissy….

I haven’t told this story in so long but after slowly getting back into cross dressing I can’t get it out of my head….

Back during my first year of college I was roomed with a theatre major who was quick to become one of the lead actors in our schools productions. This was awesome because I would be allowed to go to the cast parties and assumed I would be able to have my chance with all of the actresses that would be there….unfortunately that was not the case and at best I was just the dorky kid who hung around the leading man.

In my attempts at getting closer to the girls I would let them put stage make up on me and wear the costumes “as a laugh”. It was all in good fun until I started noticing how my roommate would look at me whenever I was dressed up. I didn’t think much of it as my mind was on the actresses and less on the actor, but then came that fateful night….

It was the end of the year cast party and once again I was made the princess in makeup and clothes, they even included a nice blonde wig! Well the night became late and I was bold enough to wear my new outfit back to our dorms with my roommate, he would “joke” and have his arm around me as if I was his girlfriend, offered me his coat and was a true gentleman…until we got to our dorm. Soon his hand was against my ass, I tried to slap it away but I was beginning to get turned on by his assertiveness and by the time we got to our room I was no longer attempting to stop his wandering hands….

Soon after we were in his bed, kissing, groping, not slowing down for a second. Before I knew it I was taking off his pants and worshiping his fat cock, he soon had me on my knees talking about how much of a cock slut I was, how he’s wanted to use my mouth ever since I first dressed up. My eyes watering and my cock leaking I didn’t do anything aside from let him use my mouth and before long I had the first of many loads dumped deep into my throat. Shortly after I fell asleep in his arms and that began a clandestine relationship over the next 3 years that I still think about…

Source: reddit.com/r/gonewildstories/comments/kampzn/mm_how_i_became_my_roommates_sissy