Home > Blogs > kenderby > > Blog Post

Transsexual (kathoey) Lilly

9:57 am Thursday, 18th April, 2019

I was on a business trip in London which meant that I had to spend an evening at one of the modestly expensive hotels near the centre. Which gave me a perfect opportunity to sample the night life of London. It was getting late and I already had a few drinks when I walked into a wine bar. I decided to have a cocktail and I had just taken my 1st sip when I noticed a group of young Asian ladies in the corner. One young slender thing caught my eye and I couldn’t help staring at her. She was exquisite with fine oriental features with shoulder length black hair with blue highlights. She was wearing a short tight skirt that moulded itself around her lovely bottom and her small round breasts and pert nipples were clearly visible through her camisole top. I could see her friends were nudging her and trying to egg her on to approach me. I smiled at her which seemed to make up her mind. She came over and introduced herself as Lilly and told me that she was from Thailand and was a kathoey. I didn’t know what that meant at the time, but I was soon to find out. Lilly went on to tell me that she was touring England as part of a Cabaret and were playing at Dartford. I loved her Thai accent and I desperately wanted to get into her knickers. As we talked I felt her fingers touch my leg under the table. Emboldened by her intimacy I stroked her naked thigh in return. I felt her fingers stroke my hard shaft through my trousers and I new she was mine. Several drinks later found us on the way to my hotel. Her friends were clearly happy for her to leave with me and even escorted us out of the bar and waved us off. We stumbled into my room laughing and carrying on. I couldn’t wait to get her top off and suck her perfect tits. I slipped my hands up her skirt and around her tight little bottom and drew her close to me and we kissed with tongues. I helped her out of her top and sucked her little titties. She knelt down on the floor in front of me and unbuckled my belt and undid my trousers to expose my Calvin Kline briefs and my furious hard on trying to get out of them. She cooed with delight as she explored the size and shape of my manhood through the thin material of my briefs. She slid her delicate fingers inside my waist band and lifted my hard shaft out, pulled back my foreskin and licked the pre cum from my bulbous end. I held the back of her head and pushed my cock between her warm willing lips and started to fuck her mouth, gently and slowly enjoying the pleasure it was giving me. She moaned and I noticed her playing with herself between her legs. She looked up at me with her horny brown eyes and I could feel myself beginning to cum. I tried to hold back and warned her that I was coming. But she just smiled and swirled her tongue around my mushroom end as I exploded into her mouth. She lifted my shaft out of her mouth and a second cum blast covered her face and tits. She stud up and looked at me with cum on her face and I noticed her cock for the 1st time. Like her it was small and beautiful, it stud upright from the top of her knickers, it was about 4 inches long and poked out from underneath her short skirt. She clearly saw my shocked expression because she pouted and looked down in a subservient fashion and said in her heavily accented broken English. “Please suck my cock”. She tugged on her shaft when she said this. It only took me a moment to make up my mind and I knelt down in front of her as she had done for me and licked the end of her cock. I pulled back the foreskin and wanked her shaft before I inexpertly sucked the end of her member. She groaned and mewed with pleasure. It wasn’t long before she came in my mouth, her milky cum tasting salty but not unpleasant. Afterwards, we stumbled into bed and with our naked bodies entwined we fell asleep. Later in the early hours of the morning I woke up and tucked myself behind Lilly’s bottom in a spooning position. I reached round and cupped her little tits in my hand and pinched her nipples, waking her up. I felt her wriggle her shapely bottom against my cock and felt immediately horny. My growing shaft was nestling between Lilly’s firm bottom cheeks. I reached round her and felt Her cock in my hand and started to wank it, slowly. She groaned as I started to move my cock between her arse cheeks until end of my cock found her tight anal opening. I felt her push against me and I tried to penetrated her but she cried out in pain and told me I was too big for her. “Just wait”, Lilly said as she got out of bed. I watched her take out a tube of lubricant from her bag and squeeze it contents on her hand and apply it to her bottom. She came over and rubbed some of the lubricant over my bulbous end and down my shaft. She returned to fetal position and allowed me to spoon her from behind. This time I felt my shaft penetrate her. I reached around and felt Her cock stiffen in my hand as I started to fuck her. She groaned with pleasure as I felt her loosen up and I was able to shaft her with long firm thrusts. She moaned and I felt her cock jerk several times in my hand as she ejaculated. I continued to wank her as I reached my vinegar strokes I paused and let myself go and filled her arse with my cum. We slept after that but we were woken up in the morning by my phone alarm. I groaned because I had forgotten that I had set my alarm for an early rise so I could go for a run before attending a conference at the Barbican. I felt Lilly stir in my arms. She turned around to face me as I shut my alarm of. I thought sod the run I have got better things to do. I felt Lilly’s firm shaft against mine as we kissed. I hugged her close to me and felt her tits against my chest. She simulated fucking against me and said. “I enjoyed last night”. I told her that I had as well even though I had never done anal or sucked a cock before. She answered me with another kiss and said. “Shall we have a shower together”. “Come on then”, I said and I pulled Lilly out the bed and guided her towards the shower. She giggled as I playfully spanked her bottom. “Oh sir”, she said. “You are so masterful”, she joked. We soon had the shower running and we started washing each other. It had nothing to do with getting clean. It was more about having an excuse to touch each other. I felt her hand on my cock as I applied soap to her tits and nipples. I trailed my fingers over her flat tummy and took hold of her hard shaft and started to tug on it. We eventually settled down to rubbing our cocks together and I could see by the look on Lilly’s face that she was enjoying the sensation of our two cocks together. She took hold of both our shafts and started to wank us both together as we kissed under the warm water. I could feel my cock tingle with pleasure and by the look on Lilly’s face I was fairly sure she was feeling the same. With both my hands free I took to caressing her bottom while I watched her delicate hand play with both our shafts, rubbing our soft bulbous ends together. Suddenly she tilted her head back and started to thrust her cock against mine vigorously while she held onto us both. She cried out and ejaculated, covering me with her cum. I took her by the hand and guide her back to the bed. I picked up the bottle of lubricant and with Lilly on her back I knelt between her knees and applied the oil to my cock and her tight hole. My cock touched her anus and I felt her cock recover and grow in my hand. I pushed my bulbous end into her and started to shaft and wank her at the same time. After a while Lilly indicated that she wanted to tug on her own shaft while I continued to fuck her. It wasn’t long before she came again, spraying me with her cum. I followed close behind and I came filling her with my cum. We went back to the shower but this time we managed to finish and keep our hands of each other. After breakfast I went to my conference and Lilly left to catch up with her friends.



Blog Introduction

Get full access to all site features
Register Now