My first shemale

The day had been dragging. It was almost lunchtime and as a regular John I started looking to take and extended lunch and get my nut off. Browsing through escort pages had been a hobby but actually committing to it had been a recent thing. I’d still get the dry mouth and butterflies in my stomach whenever I would head over. He’ll, I still texted them and would refuse to use the ones that said you had to call out of fear.

Once lunch time was approaching I decided to peruse the usual sites and pick something for a nooner. The perks of being in management were no time limits on lunch and a handsome compensation that fed into my newfound hobby. This particular day I picked a girl I’d seen many times but never chose, I guess there was something deep inside I knew was wrong but today was the day I would find out what it was. I texted her and set up the date and like a well oiled machine, the plan flowed with no issues. I arrived at the motel where she was, Sweaty palmed and scared as hell I just wanted to nut and get back to work. A failed jack off session had frustrated me that morning and the need to feel that hot cum shoot out of my dick consumed me far more than any reasoning. She texted me she was showering and would call me soon to let me know the room.

My phone rang and my anxiety was at a peak. Her voice was soft but raspy and although soothing it felt different than all I’d experienced. She tells me to go to room 110 and park in the front, she would open the door once I arrived and make my day. I did as told and once I knocked she led me into a dark room, the smell of cigarette permeated the air but all I could focus on was the ass on this girl. Her mini skirt rode up so the bottom of her ass cheeks showed and my hand gravitated to grab it as if my life depended on it. She led me to the corner of the bed and proceeded to unbuckle my pants and suck my throbbing cock. Feeling her mouth on my bare cock was amazing. She looked up and I could see those eyes water as she took me down to the base. I was in heaven. She received a call and contrary to what I though she picked up and spoke to another John asking for her as she manhandled my dick with her mouth. She would use her other hand to play as she spoke and then take me deep into her throat as she listened. After a short conversation she hung up and said that she was all mine.

She peeled her thong off the back of her glorious ass and poured oil all over it. She then laid me down and massages my aching cock with her ass cheeks, slowly grinding up and down with those lubed checks. She never turned towards me and kept the thong over the front of her, which peaked my interest but I was so caught up that I could not act on it. She then got on all fours and that beautiful ass was once again in display. She handed me a condom and told me to put it on But still she refused to remove the thong fully. Now I was fairly new at this but I sensed something was wrong, however before I could do anything she pulled my wrapped cock deep in her ass and I was in heaven. Feeling that tightness was amazing and listening to her groans and moans just made my dick harder than I’d ever felt it. As I tried to feed her up she kept guiding my hands towards her tits and I guess she noticed my hesitance in fucking her when I was unable to feel more of her. She asked me if I was ok and that if I was uncomfortable I was more than free to leave, I didn’t even have to pay but I assured her I was ok and wanted to continue. By then I realized the blue balls would’ve killed me and I needed some release. She peeled off the condom and took me in her mouth again, she noticed my curiosity as I was now putting the pieces together but she was so nice that I couldn’t bring myself to confront her. She laid with her ass to me and told me to cuddle with her and I couldn’t help but oblige. She rubber her ass on my bare cock and slowly but surely my raging hard on was sliding between her cheeks. This is where I lost all control and guided my cock into her ass. She moaned and kissed me. I knew by then she was not who she said but I was still balls deep in her fucking her raw and wanting more.

I proceeded to fuck her like there was no tomorrow, condomless and fully aware I was not going to stop. I whispered in her ear that I was about to cum and she said do it baby. I sprayed her bowels with the strength of a thousand men. Leaving me weak in the process. She said if I liked it and I told her that she was amazing but I wanted more. She looked perplexed and I said I want to see your dick. She was taken aback and shyly asked how I knew. I told her the signs but quickly put her at ease saying I was ok. She peeled the rest of her thong as my cum leaked from her asshole like a pro I licked it all up letting my mouth explore her balls and then coming up to her cock. I sucked the tip and was amazed by how good it felt. I continued till she came in my mouth and then I told her that my asshole was next.

---