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A New Leaf (Shemale Story)

Posted by: SoloTouchArchive Author: PlumpLvr Posted on: 25 Apr 2006 2 comments
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[i]There's a thread going on now about she-males. I finally found this story I wrote a while back, hope you enjoy... PL[/i]A New LeafChapter 1What a bitch. We'd lived together for almost two years. As long I as had good money coming in, she was happy to give me all the suck and fuck I wanted. But not two weeks after I'd gotten laid off, she dumped me. Not even in person at that, I got back from the employment office to find my place cleaned out, and a "Dear Jay" note from her. Which was appropriate I guess, as my name is Jay. Hi there, didn't mean to sound so bitter, but I suppose you need to know the frame of mind I was in. I guess if I sounded bitter it's because I was. I had actually thought to marry the bitch. It was quite a blow to find out I was nothing more than a sugar daddy for her. Unencumbered by ties, or furniture (she'd taken most of it) I prowled the net until I found a new job, in a new town. Hell, not just a new town, a new country! I moved from the sunny south (Atlanta) to Toronto. I told everyone I was going to turn over a "new leaf" in the land of the Maple Leaf. I found a tiny but affordable apartment in the downtown area, near where I worked. I had been there about three months before the lonliness really started to set in. By that point the rush of a new job had calmed down, and I found my evenings free. Stressed out, I finally decided a massage was in order. But from where? I checked through the paper, looked at several ads, and found one for in home massages. Perfect, I thought, I won't even have to go out. I placed the call, and set the time for Saturday afternoon.I'd had massages before, but it always ran the gambit so I wasn't sure what to expect. Deciding to play it safe I wore my bathrobe and underwear while I waited for Dale to arrive. Dale was the name of the person who I'd ordered the massage from.Right on time the door bell rang. I opened the door to discover Dale was a real looker. She was probably five foot eight, with a pretty face and long blonde hair. Her thin frame made her huge breasts look even bigger, had to be a D cup under that tiny black dress. The skirt stopped just below her crotch to show off her long legs. She came in, and I offered her a beverage. Dale was cheerful and friendly, so I suggested we talk for a bit first. I guess the lonliness was apparent as she agreed. We talked for almost an hour, me giving my sob story and her telling how she was working her way through school. Comfortable, I finally suggested we get started with the massage. Dale got a funny look on her face, and got serious."Look Jay. You seem like a real nice guy, so there's something you really ought to know."I shrugged my shoulders. "Sure, go ahead.""Well, it's like... you see, most of my customers already know and I just... well I mean it's not a big deal it's just that some guys expect certain things and before we start I guess you... well I just...""Look, it's cool. Just spit it out. I'm easy.""Well OK, now don't freak or anything it's that... well... " Dale took a deep breath. "I'm a transsexual.""Pardon?""I.. uh... well most of me is a girl but I got guy parts down... there.""Oh. OK." I paused for a moment to reflect, but she went on."If you want me to leave just say so, it's just that some guys well they get to expecting things and others just want a massage and don't care and well you seem like such a nice guy and all I just wanted to make sure and be upfront and all."Frankly her (his? well I had thought of Dale as a her so I'll keep it up) revelation didn't bother me too much. In my early teens I'd had a few male playmates, and we'd played around with each other including sucking each other off. I was in college in the very early 80's and it was rather in vogue then to be bi, and a few times I'd had some fun with guy friends including my roommate. Of course that was twenty plus years ago, and since then I'd been a devoted pussy chaser. "Look, it's cool." I said as assuringly as possible. "I don't have a problem with it. I called for a massage, and that's what I'd like."Dale let out a deep breath, in relief. "Great." she said, a big smile coming to her face. "What say we get started?"We adjourned to the bedroom where she covered the bed in a blanket from her bag. She noticed me standing in my underwear and said "You might want to remove your briefs as well. I use a lot of oils, and wouldn't want to mess them up. If you want we can cover you up with a smaller towel."I thought about it, but have never been that hung up on nudity, besides which I figured it was nothing Dale hadn't seen before. I dropped my drawers and streached out on the bed face down. I felt her small hands begin to work the oils into my skin. Soon she was rubbing all over, and I was lost in pleasure. During the massage we talked about past relationships. It got pretty graphic as I described some of the things my exgirlfriend and I used to do. I told Dale how she was a real cumslut, loved for me to spunk all over her face and tits. Also how we loved oral and anal sex. One example I told was how she used to fuck me with a double headed dildo, one end in her twat the other in my backside. Then we'd swap and I'd ram my cock up her sweet ass while reaching around and pumping the dildo (still in her) with the other."So how about since you moved up here?" Dale asked. "Nothing." I replied, a hint of disgust in my voice."Nothing? Nothing at all?" "Well, just me jacking off. Been so busy I haven't had time to meet anyone.""Must be awfully frustrating." she said. I agreed and told her so.Dale continued the massage in slience for several minutes. Finally she said "Look, I don't usually mention this on a first time massage and all, but um... well for a few extra dollars I can make sure you are... well TOTALLY relaxed."Intrigued, and more than a little horny, I asked "Let's be candid. You're offering to get me off. Just how would you do it?""A variety of ways. Some of my customers request a hand job. Others enjoy a titty fuck. For a select few, I will perform oral sex for them.""And will you be naked for this as well?" "If you want. Some of my customers want me to leave on my panties, others like to see it all."It was a no brainer decision. Really, my dick made the decision for me, no brains were used at all. "OK. I want the full thing. And if I'm paying that much, you'd better be nekkid."Dale stood up beside the bed. I rolled onto my side to enjoy the show. She peeled the black dress up and over her head tossing it to the floor. Her black panites were french cut, riding high on the thigh. She grabbed the waist band and asked "Are you sure you want it all the way?"I nodded. "Let's see it all." She dropped them to the floor, kicking them off. I got to see her dick for the first time. It wasn't huge, but not tiny either, probably about five inches. Her crotch was totally shaved, completely hairless. "Well?" Dale asked nervously."Nice. I like it." I rolled onto my back. "You go ahead, I'm putty in your hands." Dale smiled and slid back onto the bed. She really applied the oil now, getting a lot of it onto both our bodies. Wordlessly she rubbed me all over, teasing my stiffining cock. She then began stroking it, bringing it to full erection. I groaned in delight. "Jay." Dale said quietly. "Would you prefer a blow job, or a titty fuck.""Gosh, I dunno. What YOU prefer to do?"She seemed taken back that someone might actually care what she wanted. She thought for moment then said "Me? I want to feel your stiff cock in my mouth. I want to feel it slip past my lips and hit the back of my throat. I want to run my tongue over the tip, I want to taste your hot spunk as it floods my mouth."Damn, that was all I needed to hear. "You got it." I replied. "Go for it." I gasped as Dale leaned in, taking my manhood into her hungry mouth. I spent several minutes of glorious bliss, as she sucked and licked my cock. I fought back the urge to cum several times, although I don't know how. The way Dale was positioned on the bed, her head was pointed down, and legs near the head of the bed. That left "her" cock near my head. I reached over and tenatively touched it. I have received many massages over the years, some of the sexual. While they were happy to give me sex, most did not want any reciprocation. No touching I guess meant they kept it professional. Dale, however, was happy to oblige, and spread her legs giving me easy access. I fondled and stroked, bringing her to full erection. Her dick was velvety soft to the touch, smooth as silk. I rolled onto my side, and being unable to resist took Dale's cock into my mouth. It had been twenty years since I'd sucked a dick, but I'm happy to report you never forget how.Dale gasped, and said "You don't have to do that if you don't want." I ignored her and kept going, so she resumed sucking me. Dale was fondling my ass, so I reached around and fondled hers. On a hunch, I worked a finger up her asshole. Dale moaned in delight, then returned the favor sliding a slick finger up my own back door. Shit! I had forgotten how good it felt. In just a few seconds my orgasm hit me by suprise and I filled Dale's eager mouth with my cum. Only seconds later I felt Dale stiffen beside me, then tasted her cum as it filled my mouth. I'd love to say her cum tasted wonderful, but in reality it didn't have much taste at all. I was though, extremely turned on and still sucked up every last drop. We collapsed, lying beside each other breathing heavily. My cock was starting to soften a little, but Dale kept stroking it so I kept stroking hers. "You didn't have to do that. I was supposed to be bringing you all the pleasure.""I know." I said. "But it's been a long time since I got to suck a cock.""Oh, you're bi then?""Well, a little. Through junior high and into college I had a few close friends. Some of us just masturbated together, with a few we used to suck each other off. My college room mate was probably the wildest, we used to do about anything, oral, anal, whatever. Even shared his girlfriend pretty regular. Nothing since then. You?""I tend to prefer guys, which is why I'm having the operation. But I still enjoy females from time to time. You'd be suprised how many women get off on being fucked by someone with big tits." We both chuckled at the thought. By now, both our dicks were fully erect again. "I'd like to do more, if you're interested." Dale said. "How much?" I asked worriedly, my budget limited.She smiled. "No charge, this one's one me.""OK then, what would you like? Name it.""You mentioned you liked anal?" Dale asked hopefully. In response I spread my legs wide, exposing my backside. She smiled, and moved around between my legs.Dale grabbed the oil off the bed and lubed up both our crotches. Moving forward, she slowly and gently slid her dick into me. "Go slow." I whispered. "I'm a little out of practice." Dale nodded. With great gentleness she slowly worked "her" penis into me. Oh man it felt good, sliding against my prostate like that. Soon I felt it bottom out. Slowly she worked up a rhythm, sliding in and out of me. I fondled her big tits as she penetrated my ass. My cock was rock hard, pressing against her belly. We were both moaning with delight. "Oh, fuck me good." I said."I'm close!" Dale whispered in a sharp breath. "Oh fuck I'm gonna cum.""Shoot all over my cock!" I commanded. Dale pulled out and pointed her cock at mine. Hot cum dribbled out, soaking me down. Her cum wasn't very powerful, but had a lot of quantity as it really soaked me down good. She let out a huge sigh then collapsed on the bed beside me. My cock though, was ready for more action. I reached an arm under her and pulled her close. I then slid her slender frame on top of me, so that her back was to my chest, me still lying on my back. My cummy cock slid between her ass cheeks as I reached around and began fondling her d-cups. "Oh yes!" she said happily. "Take me." Her legs spread, I quickly found the opening to her back door. My wet cock slid in easily. "Oooo that's nice." I whispered in her ear. "Guess it hasn't been as long for you."She shook her head negatively. "Nope. I have a big dildo I like to put up my ass when I masturbate. I had it up there just this morning."I kept pumping, her ass felt great. While one hand continued fondling her tits, my other reached down and started playing with her cock. Our cheeks were nesteled against each other, and all of a sudden we started kissing. Yeah, I know what you are thinking. But even though Dale had a dick, everything else just screamed woman. Pretty face, long hair, huge tits, shapely ass, all just told my brain "woman". So it seemed pretty natural.Besides, I have to admit Dale wasn't the first "guy" I'd kissed. Remember mentioning my roommate in college? Well, one night we were face to face, our well oiled cocks sliding around on each other. It was dark, and we were holding each other tight. All of a sudden we just started kissing. As now, it just seemed like the natural thing to do. After that, when we were both really horny we might engauge in a little kissing in addition to whatever else we were doing. We especially had fun taking turn giving blow jobs, then kissing the other with a mouth full of cum to swap. His girlfriend loved to see us do it too. We didn't do it all that much though, maybe not more than a dozen times, and until Dale was the only guy I'd ever kissed. Anyway, my cock was feeling really great as it fucked Dale's tight ass. I broke away to say "I'm gonna cum!" "Fill my ass baby, fill it with your hot spunk!" Encouraged, I rammed it hard up her tight ass and began pumping a huge load of jism up her shit hole. As I came, I felt my hand get wet and realized Dale was cumming in my hand at the same time. Our passions spent, we broke our kisses as she slid onto the bed beside me. We fell into a light sleep.I awoke about an hour later, the bed shaking as Dale got up. "Sorry" she said. "I have another appointment this evening, and need to go get cleaned up.""I'm pretty messy myself, what say we go take a shower together?"Dale smiled yet again. "Lead the way!"We marched into my small bathroom. The shower stall though was decent sized, and accomodated both of us easily. We washed and scrubbed, bumping into each other. Overcome with desire, I pulled her into my arms and kissed her. I worked my way down, sucking each of her big tits. Dropping to my knees, I kissed down her flat belly to her stiff penis.I kissed the tip, then licked it all over, sliding my tongue up and down her smooth shaft. I gently sucked each small ball, then slid back up sliding her dick around my face. I pulled the small cock past my lips and into my throat. While my hands fondled her soft ass, my head bobbed up and down on her cock giving it the best blowjob I could. It had been decades since I'd done something like this, and I intended to enjoy it to the fullest. I continued for about five minutes before Dale grabbed my hair. I could feel her begin to shake, then felt my mouth fill up with her cum.I held it there, trying not to swallow as she filled me up. When she finally stopped I let her cock slide out of my mouth, then quickly stood and kissed her. As our tongues intertwined I let her cum roll into Dale's mouth. "Mmmm" I heard her say.Without another word she began kissing her way down my body. She sucked each of my nipples, then was quickly on her knees before me. Apparently she had sucked a lot more guys than I had, because she easily deep throated me over and over. Dale caressed my ass while sucking each of my big balls, then returned to lick and suck my cock some more. In what seemed like no time and an eternity all at once, I grunted then began filling her mouth with my own semen. She held her head still as my cock spasmed and throbbed. As she stood I could see my spunk rolling down her chin onto her tits. She kissed me savagely, thrusting her tongue into me and flooding my mouth with my own cum. To even out our height I spread my legs and leaned back against the wall, pulling her close. Our limp penises slid against each other as we kissed some more. Finally she broke the moment. "I have to be going." she said softly. "But I had a really fantastic time. I hope we can do it again?"I nodded. "Better believe it!"