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Section 1
This all happened about two years ago when I was 18. I always had fantasies of having a manhood in my mouth and backside, but I wasn’t attracted to men—just the member itself—so I decided to find a shemale. I live in a small town, so that’s hard to find. I found one about an hour away in the city. I talked to her and decided to leave work early—I was already horny anyway. The worst part was the drive because it gave me time to think and second-guess myself, but I kept going.
When I arrived, she was waiting outside, all dolled up. She welcomed me and I followed her in. As soon as I got inside, she told me to strip, so I did, and she did the same. She had a little bed set up on the floor. I told her what I wanted to do, and she laid down and told me to take her in my mouth. It was average girth, an eight-inch black member. I stared at it for a little while, then dove in, trying my best to pleasure her. I could only take about five inches, so I used my hand to stroke the rest. I worked on her until she was fully aroused—I loved feeling her grow in my mouth until she was ready.
She got up and went to the bedroom; she came back with a condom and some lube. I was a little nervous—her member was big compared to anything I had ever taken in my backside. This was my first time, but I had tried some toys, not many. Remember, I’m a smaller guy, only 5'5" and 120 pounds, so not much room back there. She laid me face down with my rear up and put lube all over her and on my shaved skin. It was a little cold. I was so hard and ready to explode, with my bottom up, feeling so vulnerable. The smell of her and the taste on my lips was almost intoxicating, along with the thought of being this woman’s plaything.
She slapped and fingered my opening for a few moments, then I could feel her warm member pressing against me. It hurt—she could tell. She pushed and backed off probably five times until the head spread my untouched entrance. She worked in nice and slow until I took that black member completely inside me. I almost fainted; it was awkward for her because my bottom was too low, so I lay flat on my belly now and wrapped my legs around hers. I remember my toes curling and her picking up the pace. She was moving frantically, pulling out and pushing back in. When her member left me, I could feel the lube running down my crack over my balls. I was so horny that I came from the friction against the covers on the floor. It was the most intense orgasm of my life. My body tightened, and then, as always, I lost my desire—I always did when I masturbated—but I couldn’t tell her to stop now, so I let her continue. My head banged against the wall, and she held me down. It almost felt like pain now, but that turned me on again. She was ready to climax; she pulled out, yelling she was going to come. I just lay there, and she released all over my back.
I quickly got up and wanted to get dressed. I could feel my rear still open, leaking lube. I was embarrassed, so I quickly thanked her and left. I thought about all the events on my way home, still feeling that stretched sensation. When I got home, I touched myself again and climaxed all over.