Since leaving my wife after several unhappy years, I’ve been visiting escorts to satisfy my urges. I started seeing escorts a few years before we finally split up actually. I’m not a very gregarious person and I’ve never been the type to pick up girls in a bar. I’m the kind of person that needs to get to know somebody before getting close to someone.
My name is Steve and I’m 39 years old. I never thought I’d get divorced because I loved my wife dearly. I still do and we parted as amicably as possible, both realising we were unhappy all the time. For me, a big part of the unhappiness was down to the lack of intimacy and sex. I tried to be understanding, but I eventually reached my limit. Did we get married too young or did we just get old? Having ended a 21 year marriage, I’ve been reluctant to get really close to anybody since. Once bitten, twice shy, as the saying goes.
I’ve found visiting escorts very exciting and enjoyable. When I stumbled across a transsexual escort named Rose, the excitement grew to a level I never knew existed. Rose blew me away, metaphorically and literally! I’ve been lucky enough to fuck some very beautiful girls over the last few years, but Rose really was special. Not only was she physically beautiful with a body that would be the envy of 95% of genetic girls, her personality was amazing. I’ve really felt a connection with this girl every time we’ve been together. She’s either the best actress I’ve ever met or she feels the same about me. The story on here, “Trans Delight”, tells of our first mind-blowing encounter. https://noveltrove.com/story/2191/trans-delight
After I divorced, I moved to a new apartment which is in the town where Rose lives. This wasn’t a consciously deliberate decision, but I’m sure on a subconscious level, I knew I wanted to be closer to her. It meant I could visit her more frequently and pretty soon, I stopped visiting any other escorts, keeping all my available funds to spend on Rose. She remarked how nice it was that I could see her more frequently now, so I told her I was free and single and living not too far from her. Her eyes twinkled when I told her this. At least, I think they did. I hoped they did.
Now Rose and I were so well acquainted, I would text her for an appointment. I dropped her a text one day and she replied immediately, as always. “Sure Steve, tomorrow at 5pm is great. See you then, I can’t wait! X” read her text. I got the familiar weak feeling in my knees, knowing another great session was booked. Friday at 5pm, so no hurry to rush back to work afterwards. Perfect! It had been a long week and I was in dire need of some R&R. I couldn’t think of anybody else I’d rather spend an hour or two with than the beautiful Rose.
I pressed her buzzer at one minute to five, knowing she’d let me in with no words. Sure enough, the door lock clicked, I pushed it and went in, walking straight to her apartment door, which was already ajar for me. I closed it behind me and heard “Hi Steve, come on in.” Rose was waiting for me in her lounge looking stunning, as always. She was wearing a clingy see-thru top, with obviously no bra, and a pair of silk cami-knickers. “Hi Rose, how are you Honey. Oh, you’ve changed your hair, it looks lovely,” I said. She smiled a warm smile. “Trust you to notice and thanks, I’m glad you like it.” We kissed a proper hello and as usual, it turned into a full-on deep French kiss, arousing me instantly.
“Wow, I’ve missed you Babe,” I breathed as I kissed her neck. “Me too, Steve,” said Rose, as she cheekily squeezed my crotch! She knew I always liked a shower before we got too intimate and today was no exception, especially as I’d been cooped up in my car all day. Rose released me from her grasp and I slipped my jacket and tie off. She waved her hand towards the bathroom and I took the hint, stripping down to my boxers and taking the towel Rose handed to me. “I’ll be with you in a moment,” she said, “I just have to get something from the bedroom.” I never gave that another thought as I walked into the bathroom and started the shower. I dropped my boxers to the floor, tested the water which wasn’t too hot, and climbed into the bath. I stood under the flow of water and washed away the woes of the week, soaping myself thoroughly. Within a few minutes, Rose was standing behind me, her hands helping to lather up my body. I reached my arms behind me and felt her sexy bum. Rose was paying extra attention to my own ass today, with lots of soap rubbed all over my cheeks and in-between them too. She always liked to do things a bit differently at every meeting and it kept things fresh and exciting. Sometimes she would suck me off in the shower, sometimes I’d suck her. At one meeting, I was so horny that I actually penetrated her ass with my cock while rubbing it up and down her soapy ass crack. She moaned loudly as my cock slipped in to her and I so wanted to fuck her hard and deep right then, but as we didn’t have a condom to hand, I pulled out quickly and replaced my cock with two fingers.
Today, she was working on my ass. At our last meeting, she’d offered to fuck me, something which I’d never tried. I liked her tongue or her finger down there, but I wasn’t sure if I wanted her big cock in my anus. It wasn’t that I was prudish, it was just so big. Call me a hypocrite if you like, but I remained to be convinced that receiving anal was for me. I continued to enjoy her attention around my ass hole though and when she let the water rinse the lather away, I was delighted to feel her tongue push into me. My cock was standing tall and Rose reached around with one hand to stroke it as she tongued and fingered my tight hole. She usually makes me cum in the shower so when we really get down to it later, I can last much longer. I felt what I thought was more soap around my ass and I wondered why she would lather me up a second time. Then I felt her lips kissing my bum cheeks and something was pressed up against my anus. My sphincter relaxed a little and I felt something bigger and smoother than a finger slide into me. It felt amazing and I gasped as Rose started to fuck me with her favourite yellow dildo, all the time jerking my engorged cock. So that’s what she had to get from the bedroom!
“You like how it feels, Baby?” Rose asked. I was almost too stupefied to answer. The feeling of being penetrated was breath-taking, all I could do was sigh and nod my head. Rose pushed the dildo into me as deep as she could then turned me around to face her. She held the dildo inside me then took my cock into her mouth. She didn’t suck but just held it there and continued to push the dildo in and out of my ass. She cupped my balls in her free hand, ran her tongue over the head of my cock and pushed the dildo into me one last time before I groaned a deep, primal groan and came hard, filling Rose’s mouth and throat with my seed. My ass was contracting like a girl’s does when she cums and my cock spasmed long after my cum had stopped flowing. This was the best showergasm I’d ever had by a country mile! Rose looked up at me as she licked my cock clean, let the dildo slide out of me then stood up, put her hands around the back of my head and kissed my mouth deeply, quite deliberately dribbling cum from her mouth into mine. We shared this dirty kiss for a good few minutes before she released me, giggling. “Well, how was it?” she asked, already knowing the answer. I looked Rose in the eyes, shook my head and said “You are fucking perfect!” She giggled again, reached down and gave my knob another kiss and jumped out of the bath, taking the yellow dildo with her. With what little energy I had left, I finished washing myself, got out of the bath and followed Rose back into the lounge, drying myself as I went.
Rose was already dried off and grabbing some water from the fridge. She handed me a bottle and I rehydrated myself, flopping down on to Rose’s plush sofa. I’d been at her apartment for precisely 30 minutes and already felt relaxed, spent and sated. The problems of my week had drifted away and I felt mellow and calm. “I think you quite enjoyed that, Baby?” Rose asked teasingly. “Honey,” I replied, “it was absolutely amazing. Now I know why you like it up the bum!” Rose smiled at me and said “Oh, you haven’t felt anything yet. My cock is so much nicer than that dildo, so whenever you’re ready, just say the word!” Wow, could this get even better, I asked myself. Knowing Rose, it probably could!
She sat next to me on the sofa. We were both completely naked and Rose’s cock was hard and ready for action. We kissed again and I ran my hands over her insanely hot body before reaching her cock. I loved the feel of it in my hand and how it throbbed when I wrapped my fingers around it tightly. I also loved that Rose moaned when I held it and started to jerk her foreskin back, exposing her glans. It was just too good not to suck, so I dropped onto the floor, positioned myself on my knees between her legs and started to feast on her perfect cock. I remember the feeling the first time I sucked Rose, and each time I’ve done it since, I get the same heady feeling. Her musky odour fills my nostrils and the unique taste of her sex fills my mouth. I try and copy the way Rose sucks my own cock, so I give her balls plenty of attention with my fingers and my tongue, taking each one into my mouth gently while jerking her. She must have been exceptionally horny today because I was only down there a few minutes before her hips started to buck, her tummy muscles tighten and she let out a huge moan. “Oh Steve, Baby, yes!” and her cum started to spurt out and fill my mouth. I sucked and swallowed as I felt her balls contract and her cock pulsate. Rose’s cum tasted sweeter than ever and I just had to share it with her. I reached up to kiss her on the mouth and for the second time in ten minutes, we shared a dirty kiss, cum dribbling down our chins and a glob landed on Rose’s left nipple. I quickly dropped my head to lick it off, then went back down to her cock to make sure I’d got all her cum, licking her cock head clean.
“Oh Baby, I love you….. doing that,” stuttered Rose. Wow, she almost said she loved me then. Did she correct herself to save face? I didn’t care. I looked her in the eyes and said “I love doing it and,” pausing for dramatic effect, said “I love you.” I kissed her again and we cuddled up together like lovers do.
My head was really spinning now. Had Rose got carried away with the moment? Probably, but I knew what I heard her say. I really did feel very loving towards her and she hadn’t said anything when I told her I loved her. Rose broke the silence and said “I really want you inside me Baby, come on.” She stood up, held her hands out to me to hold and lifted me up from the sofa. She led me into the bedroom and she crawled onto the bed, patting it next to her, inviting me to join her. I eagerly obliged and we immediately started to kiss again. I kissed her lips and her neck, her ears and her shoulder. I feasted on her hard nipples, tasting the remnants of her cum on one of them. I squeezed her ass cheeks as I kissed all the way down her firm, fit body and down to her thighs. Rose was moaning with every kiss and caress and squeaked as I turned her over on to her tummy so I could continue kissing her, this time all over her peachy ass cheeks. My tongue grazed up and down her crack and I used my hands to pull her cheeks apart. I ran the tip of my tongue all around her anus then pushed it into her, enjoying hear her say “Oh my God, yes!” I tongue-fucked her ass hole like this for several minutes, letting my saliva flow to lube her ready for my cock. Rose knew what was coming and handed me a condom. Without any manual stimulation, my cock was fully hard and ready to go again, ready to plunge into Rose’s tight, sexy ass.
I rolled the condom down my throbbing cock and with Rose still lying on her tummy, I sat astride her thighs, positioned myself with my knob pressed against her ass hole, and pushed in firmly. Rose let out a huge sigh as I buried my cock deep into her tiny asshole. Fucking in this position is like doing push-ups, although much more fun! I was glad I’d been spending more time in the gym lately because I wanted to set the world record for how many push-ups a man could do on a bed while penetrating a beautiful transsexual girl underneath him. I haven’t seen that listed in the Guinness Book of Records, but being the pioneer I am, I like to be the first to set the standard! Unfortunately, despite my best efforts, I couldn’t manage more than about twenty or thirty thrusts. Not because my arms couldn’t take it, but because Rose’s ass was so tight and sexy and made me want to cum so damn quick! I eased out of her to give my poor little feller a breather. I didn’t want to cum again yet. Rose understood and said simply, “Oh, good idea. Your turn now!”
I climbed off her and Rose saw I was a bit apprehensive. “Trust me, Steve, it’s gonna be awesome.” She turned over and her cock was rigid. She rolled a condom onto it and squeezed some lube out of the tube, covering her knob. She got some lube on her fingers and reached forward to lube my ass hole as well then said “Ride me, Baby!” I thought, OK, this is it. I straddled her legs again and lowered my hips until I could feel the tip of her well-lubed cock touching my anus. I eased down further and felt the tip slide into me and it was easier than I’d thought it would be. My muscles must still be relaxed from the dildoing in the shower. Rose had her hands on my hips and she was guiding me, allowing me to slide lower and lower until her cock was balls-deep in my hole. It was an overwhelming feeling. No pain, just an urge to go to the toilet, which passed quite quickly and a feeling of being completely full. Rose encouraged me to lift up and sink down onto her again and I established a gentle rhythm. I was loving this and moaning loudly each time her cock penetrated me.
The intense stimulation of my prostate had my cock twitching wildly and as I hadn’t cum when I was fucking Rose a few minutes earlier, the urge welled up in me very quickly. I didn’t know if it was as satisfying for Rose as it was for me until she started to moan as loudly as I was. I heard her say “Shit!” and felt her fingers dig into my thighs as she came hard. This was a whole new sensation for me, feeling a big hard cock cumming inside my ass, pulsating and spurting cum into the condom. I sat still for a moment, completely impaled as my own orgasm erupted, shooting five or six streams of cum all over Rose. I came so hard, the first spurt hit her full in the face, the second one shot over her head and splashed against the bed headboard, and the last three or four splattered her breasts and belly. “Oh my fucking God!” blurted Rose, “that’s fucking amazing!” I couldn’t speak, I was shaking and gasping for breath, trying to take in the amazing view of a cum-splattered beautiful girl underneath me while my ass was contracting and my cock aching with the force of my cum shot.
I leant forward and Rose’s cock, which was now softening, slipped out of me. I collapsed on top of her, kissing her deeply, her pretty face covered with cum and now my lips and tongue hungrily licking it from her mouth. Our bodies were stuck together with the rest of my cum and I wanted to stay in that position forever! We kissed for ages and eventually, we peeled apart from each other, making us both laugh. “I guess we’d better shower again,” said Rose, through little snorting laughs which made me laugh too. We tiptoed into the shower and had a good soapy wash, rinsed off and dried ourselves as we wandered back into Rose’s bedroom. It was now around 7pm and I was conscious of the time. I didn’t want Rose to think I was taking her for granted by overrunning every time we met. I needn’t have worried.
As we were dressing, Rose said “You don’t have to go yet, do you?” I hesitated and said “Nope, nowhere to go except home alone!” with a forlorn look on my face. “Good,” said Rose, “I’ll make us some dinner.” With that, she jumped up and headed towards the kitchen. She popped a fresh pizza in the oven, tossed a salad and asked “Beer or wine, Darling?” I walked up behind her, slipped my arms around her tummy, kissed the back of her neck and said “You cook for me and give me beer? Are you sure you don’t want to marry me for real?” I loosened my hold on her and she span around. “I’m not sure about marrying you just yet, but I’d love you to stay with me tonight,” her big eyes looking hopefully at me. She reached up and kissed me on the lips and I wondered if she saw the look of disbelief in my eyes? “My darling, nothing would give me greater pleasure. To spend the night holding you would make my day, my week, hell, my life complete!” I kissed her tenderly and I’m sure I saw a tear in the corner of her eye. She pulled away from me and said “That’s settled then,” and went to the drawer to fetch some cutlery. I saw her wipe her eyes when she had her back turned to me and I knew she’d caught the same feelings as I had. When she returned to the table, I sat down and held out my hands. She took them and I pulled her towards me and she sat on my lap. I kissed her and said “Rose, I really love…. spending time with you, Baby.” She smiled and said “I really love…. spending time with you too, Steve.” We both knew what we meant.
We ate, we chatted, we laughed and we teased each other. I told her about my work and she shared some of her stories from her modelling work. It was the best date I’d ever been on. After dinner, Rose put some music on her iPad and we cuddled up on the sofa, totally relaxed in each other’s company. I stayed over that night. I went home Saturday after lunch and returned with fresh clothes. I stayed with Rose until Sunday. This became our routine for the next few weeks. I’d turn up on Friday evening after work and stay all weekend. I never paid Rose again, and we made love several times each weekend. Each time felt better than the last to me. I wasn’t just fucking a goddess, I was getting to know a lovely person, truly beautiful both inside and out. I’d already fallen in love with her and I didn’t want to be with anybody else.
Rose had stopped advertising and her client base was tailing off. She only had one or two clients a week now and whilst I wasn’t keen on other guys fucking her, I couldn’t be that hypocritical and ask her to stop working. She never hid the fact that she still saw a few clients, but always apologised to me before each meeting, like she felt she was cheating on me. Her modelling assignments were picking up again. Just modelling, she assured me, no more porn, so she wasn’t short of money. I figured the time had come to pool our resources and move in together. I wasn’t sure how to broach the subject, knowing how much Rose valued her independence. Maybe she’d had enough of that now, I’d just have to ask and find out. I was quietly confident that she’d say yes. The way she’d been with me recently and by reading between the lines, I could tell she was ready.
I got to her apartment one Friday evening surprised to find she wasn’t there. She’d left a note saying she’d be late and she sent me a text a few minutes later saying she’d been delayed further, but she’d be home as soon as she could. I was a bit annoyed because I had a special evening planned. I’d bought a bottle of champagne which was now chilling in the fridge. I’d tied a little silver pouch around the neck of the bottle.
Inside the pouch was a sparkling engagement ring.