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First time with a guy... my roommate and best friend. [true]
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prettylilpiss is in true
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I have been crossdressing for awhile, I have gone down on a few guys. Nothing like what is going on right now. I recently moved back to a larger city I lived in for awhile. I have quite a few friends here and I am living with one of them and their wife. We were getting drunk one night and I decided to tell my friend I was bi and that I crossdress. He was very supportive and made me feel super comfortable about it. I was pretty happy because not many people know about that side of me and I have been nervous what friends would think. He said it would be fine if I felt like dressing up around the house. "Just be you" he said.

So I started dressing up when I got home from work and going about my day. It felt great to be comfortable and confident in my own skin. We do a lot of stuff together. Well one of these days he asked for some help hanging some shelves in his and his wife's room. I was wearing a cute short black skirt, garter, and fishets. I was looking delicious. We were also both having a few drinks and getting other household chores done. While doing all of this I noticed he had a half chub going on. Being a little tipsy, I teased him a bit about it. He brushed it off and kind of clammed up. I dropped it.

I know he is frustrated with his sex life with his wife. She just never wants to be intimate with him. The more we hung out when I was in girl mode and the more I found out about how sheltered he was when it came to sexual experiences, the more I wanted to have sex with him. I think he did too.

It all kind of came to a point where one night, we were chilling, drinking, and I was in regular guy mode. The conversation was kind of hot and heavy. He admitted to thinking I was really hot dressed up and that he had been masturbating to thoughts of me. Being drunk and horny, I told him we could fool around if he wanted. I'd give him a bj and we could take it easy. He shyly agreed. I went to my room and got dolled up and messaged him to come in. He nervously walked in and laid across my bed. Very stiff and wary. "Are we really doing this?" He said. I just saddled up next to him and laid my head above his waist and began to wiggle and run my hand up and down his thigh and gently over his crotch. "Oh shit" he whispered. I pulled at his shorts and slowly exposed more of his quickly stiffening cock. Gently blowing air directly onto it. Tracing his girth with a soft and careful stroke. I started to tease the swollen and smooth head of his cock with my wet whore lips. It was exhilarating. I felt his body tighten when I wrapped my warm lips around his head and began to suck softly. I worked that dick with my mouth and hands until I thought he was going to explode. I could tell he wanted more and was also still very nervous. I mean his wife was sleeping in the room nearby. "Do you want to fuck me?" I asked with him still at my mouth. He nodded and I laid on my back ad presented my virgin hole to him. He picked up my thick thighs and pushed my legs back giving him better access to my pussy. He grabbed my semisoft clit as he pushed against me hungrily with his wet cock. I felt him slide in and I moaned like the slut I am. I was immediately his. The first real cock was now pushing deep into me, owning me and it was one of my best friends. Should I continue?

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2 years ago