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First Time Fucked as a Crossdresser

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Author's Notes

"This story is true"

When I was 30 I went to a Rocky Horror show with a friend. She wanted me dressed as Frank so loaned me a basque, stockings, suspenders and thighboots. It felt very odd being out like that. After the show we went back to the hotel and I fucked her still dressed. A story for another time. She gifted me the outfit saying it looked better on me.

There was a male friend I had been playing with for a couple of years, he was a few years younger, 6'2", with an 8inch uncut cock and Top.

I started wearing the outfit around the house, just for myself but hadn't told anyone else. One night, around 10pm my friend texted asking if I was horny. I was, I was also wearing the outfit and we had never discussed anything like this. I took a chance and texted him I was wearing something on the "feminine side", at which pointed he texted back demanding I head over, dressed. I was terrified at the prospect of going out like this, but reasoned it was friday night, those not in bed would likely be clubbing, and he only lived a few stairs from me, maybe a few hundred feet away. So I put on my longest coat, which came to my ankles and headed out, basque, stockings, thighboots, no knickers. The sound of my heels clacking on the pavement seemed incredibly loud to me and I worried I might attract attention. I got to his flat without incident though and his door was unlocked as usual when we were going to play. Heading in I found him in his robe, reclining on his Lay-Z-Boy. His cock already pointing at the ceiling. He ordered me to drop the coat. I did and I could swear I saw his cock literally vibrate when he saw what I was wearing. He motioned me over and I got down between his knees. I started stroking his shaft, I don't think I had ever felt it that hard! I started licking and kissing his cockhead before wrapping my lips around it. He grabbed my head and pushed down. Lifting his hips at the same time he started fucking my mouth deeply, almost throatfucking me, my saliva ran down his shaft, beginning to coat his balls. He suddenly stopped his cock thrust deep enough that I could feel my gag reflex react but he held my head so I couldnt get away. His cock began spasming and cum spurted into my throat. I felt like I was sucking down a maccy d's milkshake there was so much. I had finished swallowing, and begun cleaning his now softening cock, when I heard his front door open. Someone walked in and my friend said "cool, you made it. This is the cockslut I told you about."...

Written by Lilmisskinkyboots

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