At the time, I was living in the street that was full of the shemale working girls. I had the opportunity to watch them every night and listen to their amazing shemales stories.
After a while, from all those shemales stories I realized that their customers were not after the anal sex as I imagined. Actually, they were but they came to my neighbor shemales in order to be fucked and not to fuck them. “You should try it sometimes”, Daisy used to say to me. “Everybody wants a hard cock in their ass at some point in their lives.”
“You’ll be the first to know if it ever happens to me.” I replied. And I have to say that she was right. I got curious. Very curious. So, I had to wait a while and get amazingly plastered before I gathered my courage to go to Daisy one night and say “I think it happened”.
“I’ve been waiting for this for a long time” she said, and gave me a good, wet kiss. We began making out but I was reluctant to touch her anywhere below the waste. She had to encourage me, and she showed me her dick.
It wasn’t particularly big, which was great because I was totally scared. I took all mu clothes off and asked her “Now what?”. “Now, you get on my bed and let me do the rest. Trust me, I’m a professional”. I grinned and surrendered to her feminine but very strong hands.
I could feel the lube first and then her cock. She pushed it gently but I was too tight. She didn’t force it but worked her way in. Gradually, she could put only the top of her dick in, and I clenched every time she tried to push it further in.
“Just relax, if you fight it, it’s only going to hurt you more.” I wanted to relax but I couldn’t do it. And then she decided that it would last forever if we paid attention to my pain and she shoved her cock all the way inside right to the root.
I screamed because of the pain, but soon enough, the pleasure replaced that feeling but kept its intensity. Shemale stories were right. You really crave a dick up your ass at some point, and this was my point. Daisy fucked me in the ass and I loved every second of it.
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