A Virgin Crossdresser

I strolled into his room with my sluttiest walk and he was pleased with what he say instantly he pulled me in for a kiss which we both fell into. He was instantly hard nice 6 inch cock to break me in, I went down on my knees pulled the boxers down and sucked my first cock. It tasted weird at first but I was soon used to it strolling the shaft and sucking on the head just as I had watched some many shemales and pornstars had done in the videos I watched. Tasting pre cum I knew he was ready to pop my cherry.

I got on all fours and almost instantly he knew what I wanted he applied some lube and a condom and I felt the head press against my hole. When it entered I almost let out a scream in pain he said sorry as well how sweet but we soon eased into it he pounded me for almost half an hour It was a blur of emotions for agony to dullness then to pleasure I started to moan and he started to pound faster I was in heaven. He flipped me over on to my pack and went to town now completely moan like a slut he finished inside me.

I was still lucid and hard as a rock he quickly went for a shower then came back and he was hard again. Lucky me I went straight to work and sucked him while he wanked me off for another 15 blissful minutes he didn’t even warn me when he came and I took it down my throat like the slut i’am. At that moment I came as well and my horniness has gone feeling disgusted with myself .

I cleaned myself up and said thank you and walked out a 18 year old boy with a secret and the taste of cum in my mouth.

I never met him again and my meets have been sporadic since. Twice a year Jessica comes out to play since I was 18 and I’ve had many girlfriends but nothing ever beats that blissful pounding and reward at the end .