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My First Time With a Shemale
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When first assigned to Germany I spent two weeks at the Replacement Depot in Frankfurt. Each day after I failed to receive an assignment I was free to wander. After a few days I decided to explore the town and took the U-Bahn into the city.
It wasn't long before I found the redlight district. Too young and nervous to enter a brothel I began wandering the sex shops. I was amazed at the variety of porn and the fact that it was much more hardcore than the stuff easily found in the US. It was still before lunch and most of the shops were all but deserted. I entered one to find a beautiful bored looking shemale standing inside near the door. I was a bit shocked and began to wander the aisles pretending to look at the magazines while sneaking peeks at her. Everytime I looked at her I fould she was looking at me with a slight smile on her face. She walked over to one of the private movie booths, stopped and looked at me with a questioning look. My mouth went instantly dry, my legs started shaking and my cock went rock hard. I nevously looked over my shoulder to see the shopkeeper making himself busy and ignoring us.
I walked dream like up to her and she took my hand and led me into the booth and shut the door. We managed through the language barrier to agree on a price and she began kissing me and rubbing my cock through my jeans. I tried to fondle her breasts but she stopped me explaining they were a recent addition and sore. After a few moments she slid down the wall of the small booth to a crouch balancing on her high heels. She undid my pants and dropped them to my knees and took my aching cock into her mouth. Now my legs were shaking like jackhammers and I had to concentrate hard not to cum in the first few seconds. She grabbed my ass and began drawing me in as she sucked. I was in heaven as she gently began circling and probing my asshole with her fingers while pulling me in to fuck her face even harder. I didn't last long and began to cum and cum. She continued to suck my cock but I just had to pull away. She let out an approving "Mmmmm" as she swiped the cum and drool from her lips with her manicured fingers. I thought we were done. I was wrong.
She stood and took me by the arms and switched positions making me face the wall. She began kissing my neck and ear. Then she again crouched down and parted my butt cheeks and began licking my ass. Soon her tongue was darting deeply in and out of my asshole. She pulled a small bottle of lube out of her purse and stood behind me. I could feel her putting lube on her cock and my ass. I was really nevous now and almost bailed but she pushed my head and shoulder toward the wall with one hand a pulled my hips back with the other to get better access. I felt her take her hand and press the head of her cock against my ass. I gasped as the increasing pressure gave way and the head of her cock popped into my ass. She hestitated a few seconds and asked "Ok?" It hurt but I wanted it now as badly as I had wanted anything in my life so I nodded yes. She pushed her cock the rest of the way in and began slowly fucking me. The pain subsided quickly and soon I was pushing my ass back to meet her thrusts. I remember being embarrased as hell when the sound of her body impacting my ass made loud slapping sounds as she fucked me harder knowing the shopkeeper could probably hear it. Soon she tensed up and dug her nails into my hips and I could feel her cock pulsing as she shot her cum deep inside me. She pulled out and we caught our breath and dressed. I paid and thanked her and she gave me a "sweet silly boy" kiss and we exited the booth. The shopkeeper snuck a peek at me and I felt my face flush, I almost ran out of the shop. Walking down the street afterward I could feel the mixture of her cum and lube greasing my butt cheeks and felt everyone I walked past somehow knew I'd just been sucked and fucked by a shemale just by looking at my face which was bright red, hot and flushed.
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Posted on : Jul 16, 2021
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