Shemale Phone Sex with Carla: School Boy Crush

There is this guy I have known for years. Just a big bully. We went to school together when I was a traditional boy. But I was never really traditional. I mean I always felt like a girl trapped in a man’s body and that was obvious to the other school boys, Jordan in particular. He called me fag and freak and really made my life hell.  He never left our city either. I have to see him sometimes at the gym. I just avoid him. The other day he approached me while I was on the treadmill. I was stunned. He didn’t recognize me as a girl. In fact, he asked me out.

I was pleasant but told him I don’t go out with strangers. He asked to friend me on Facebook in an attempt to not be a stranger much longer. Well I reluctantly agreed. I really despised Jordan, but perhaps he had changed? His Facebook feed was filled with gay bashing. I just hated him more, but now I thought maybe I should fuck him to teach him a lesson.  After a few days of interacting via social media, he realized we had a bunch of mutual friends from our youth and that we went to the same school. I thought I would be sly. I asked him if he knew Carlton Heinz? I passed myself off as his half sister. Jordan actually admitted to being mean to my brother, well um, me.  Then the most shocking thing ever, he admitted he had a crush on him/me in school but was afraid to admit it because he never considered himself gay. I said we are all bisexual if you really think about it. So I guess he taunted me to deflect his own feelings for me and now lives in the land of denial about his own sexuality, so he gay bashes.

He needed my help. He needed my cock. So, I finally agreed to go out with him. Jordan was attracted to me still after all these years, but he just didn’t realize it. I had to fuck him now. After a wonderful dinner and a play, we went back to my loft. We started making out and his cock was throbbing in his pants. Mine was throbbing in my panties, tucked under my ass as not to show through my dress.  I went down on him, swallowed his cock. He guided my head up and down his shaft. He came in nothing flat. He wanted to pull my panties off and return the favor. I told him I very much wanted him to reciprocate but I had a small confession. He thought I was on my period or was having a personal grooming issue. He was shocked, but pleasantly so when he saw my throbbing rod. I explained I use to be Carlton. His cock got hard again almost instantly. He admitted he has been carrying a torch for me  since our school days and I looked even more amazing than I did then. He fell on my cock. I could tell I was his first cock, but it still felt great.

We continued to fuck in my steam room. I am usually a top, but I was a bottom for Jordan. He clearly had been waiting a long time to fuck my hot ass and now he finally had his chance. Not sure if I like him yet, but his cock felt good in my ass. I have issue with closeted guys who can’t accept who they really are. But didn’t stop me from jacking my cock as he pumped inside me, jizzing all over my stomach and tits as he came. It was an incredibly hot experience. He got to fuck his school boy crush, I got a hot load of cum.  Still hard to believe he crushed on me all these years when he was so mean to me that I hated him for decades. Guess it is no different than a traditional boy pulling the pigtails of a traditional girl because he likes her. Now we are grown up and pulling on cocks instead!

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