It was the summer of 2017, I was 27 and I'd only ever been straight but had been curious for some time prior, as well as increasingly starting to watch gay/bi encouragement porn and Shemale porn. Eventually one night while slightyly tipsy from a night out and very horny I decided to search on my phone for TS escorts in Glasgow and came across the website birchplace. After browsing for a little while I started calling the numbers of the ones I liked the look of with limited success, either no answer or weren't available, until eventually I got through to Luciana. From her profile pics I could see she was a stunning italian in her late 30s with a thick 8 inch+ cock and it explicitly stated she was top only.
I introduced myself, asked if she was available for an hour and told her I'd like to come over ASAP, after discussing for a few minutes we agreed on the time & price and once off the phone she text me an adress in merchant city, not too far from where I was. I started to walk in that direction, my heart feeling like it was going to beat out of my chest the whole way. Once outside the address I gave her a call and she buzzed me in. As I headed up the stairs to her flat I did start to have second thoughts but thought well I'm already here and as I reached her floor she opened the door and quickly got me inside where she had other TS friends in the living room checking me out as she led me into her bedroom where we got the business part out of the way before she offered me a drink then pulled me in for a kiss as she grabbed my ass.
She then offered me a shower which I agreed to so I was led to the bathroom and left to it and once I was done not really sure if I should get changed back into clothes or not I just put the towel around my waste and made my way back to her room where she was lying on her bed stroking to some porn. She quickly got up and came over to me again to start kissing, as soon as she embraced me my towel fell to the floor and i could feel her semi hard cock pressing against me as her hands continued to explore the rest of my body which made the blood start to rush to my dick too. Before I knew it she had manouvered me to her bed and told me to lie down.
At this point she crawled over the top of me and stradled my chest, her cock was still semi hard but very big and I could see her making it twitch, instinctively opened my mouth and started sucking the tip before taking the shaft in my hand and taking more of her into my mouth, feeling her getting harder and tasting some precum leaking out. Eventually she told me to relax my throat and attempted to fuck my face. I hadn't told her this was my first time so I struggled and everytime I gagged she took it out slapped my face with it and told me to relax my throat. after a while of this with not much success other than getitng her fully erect she climbed off from my chest and positiond herself between my legs, which she lifted up towards my chest to reveal my hole. she told my to hold my legs up for her as she started to rub the head of her dick and precum in between my ass cheeks and pressing it gently against my hole, I remember tightening up a bit at this as she was bare still and she asked me if I liked it which I still said yes to.
She then got me to get into doggy on the edge of her bed while she went and got condoms and lube from a drawer and got herself ready, she placed a towel underneath me and I could hear her squirting the lube out onto her cock and stroking herself as well as fingering it over and into my hole. Then she positioned herself behind me and pressed her cock up against my hole again slowly applying more & more pressure to slide it in. I tried to relax but as I felt the head of her dick pop in she also took a quick hard thrust which sent a pain through me that made me try to get away, I'm not sure if she realised I was a virgin at this point but she grabbed my hips and just held me still with her inside me and told me to relax and get used to the feeling of her in me. we stayed there for a few minutes like that before she eventually started to slowly pull out and thrust in again. It wasn't long before she started to pick up the pace, going a little deeper with every thrust, her hands grabbing my hips tightly and once she finally managed to start fucking me balls deep she spanked me, I could feel myself tighten around her everytime she done it and I could hear her let out a moan every time it happened.
Once she was into full flow, I tried purposefully tightening myself around her cock as she fucked me and that really made her moan, I could feel her grabbing my hips tighter pulling me back onto her and her balls slapping against me with every thrust. We must have been going at it like that for about 25-30 minutes, occasionally I would reach back grab her legs or ass and pull her all the way into me just so I could get a break. Eventually after maybe the 4th or 5ht time of me doing this she pushed me flat onto my stomach on the bed, moving one of my legs to still give her easy entry and she lay her full weight on me and began to start pounding me harder and fast than she had done so far, i could feel her heavy breathing against my neck and in my ear and turned my face around to start kissing her as she fucked me, our tongues exploring each others mouths as we both began moaning quite loudly.
This went on again for maybe 10-15 minutes, still occasionally spanking me before she pulled me back up into doggy while still inside me, occasionally slowing down her pace but doing long strokes or pulling out completely and slamming it back in balls deep before finally I felt her speeding up again, grabbing my hips and moaning increasingly louder when I felt her pull out, heard her take the condom off and lay it on my back as she shot her warm sticky load over my ass cheeks. All I could do was stay there with my ass pointing towards here, no doubt gaping and winking at her and before I knew what was happening I felt her rub her cock over her load and guide it back into my bareback, I hadn't wanted her to go bare but knowing that she was in me unprotected and had used her cum as lube sent me over the edge as ropes of cum started shooting out of my cock onto the towel she had placed down while she fucked her load into me.
once she started to get soft again and pulled out she gave me some tissues to clean myself up before we started to put our clothes back on and she rolled a joint for us to share while we chatted and composed ourselves. as I was leaving she once again kissed me and did ask if I would like to go clubbing in polo with her and her friends which I wish I had as I imagine it would have led to more fun afterwards but as I wasn't out at that point in time so I politely declined, we kissed one last time and I started to make my way home.
As I was walking home, I could feel wetness squirting out of me ass into my boxers, not sure if it was lube or cum but either way it made me feel very slutty and horny again and I was thankful it was dark so nobody could see the wet patch that had appeared on my jeans!
