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sometimes strangenessi s where the heart is
It was mid October, the air was cold, and Halloween was just around the corner, which happens to be one of my favorite times of the year. I decided to go to one of the local bars, one that was known to be a bit on the alternative side to meet up with some friends and have a few drinks. I carried with me my sketch book, since I was not much of one to talk to people I didn’t know, a little bit introverted, and I used any chance I could to get in a sketch or two. As I waited for my friends to show I had a drink while I sat at one of the tables. In truth it was more like a tall backed horse shoe booth, one of many that we would occupy during our visits, and since I was the first one there I figured I would secure one for everyone to pile into later on.

It must have been a couple of hours, and no one had shown up yet. This left me feeling like I had been stood up, which really didn’t bother me all that much. So, I took out the sketch book and started a new drawing, just something comic bookish, maybe a bit fantasy, but it was getting difficult to see what I was drawing. So, I took my things and drink and moved to the bar itself where there was more light. After finding a nice comfy stool to settle down on I flipped back to the page and continued drawing, only looking up long enough to ask the bar tender for a fresh drink.

What I had not noticed was the empty stool next to mine becoming occupied, but with my down cast eyes I only caught the glimps of black stockings, and a very feminine thigh. I smiled a touch at this always enjoy the sight of a lovely woman, but I surely was not going to be so rude as to try and make idle small talk. Besides she had more than likely been hit on more times in the past hour then I had in my whole life, adding one more would simply be another nail in the night time coffin as it were.

When I had finished my third drink I was feeling rather relaxed, and was completely lost to my own little world of lines and details. What I had no noticed was that the woman that had taken the stool next to mine had been secretly watching me, more so watching each little fine stroke of the pencil, every little fine point of detail that I poured onto the paper, but that changed quickly when she spoke, “Wow, you really are talented.”, she said leaning closer to me so I could hear her over the loud thundering music, and of course snatching me out of the tunnel vision that I was quite happy to remain in.

“Thank you.”... I said back to her looking at her face for the first time. God she was a beauty, she had long straight hair of black so black that even in the dim light the shine held a hue of blue to it, and equally dark eyes. I could only assume that she must have stood around 5' 7", and I could help myself from giving her a quick once over with my eyes. She must have been a good c- cup, and had curves in all the right places. She wore a short black dress, and shining black high heeled pumps. This woman was a goddess, and the envy of lustful wishing of others, which left me feeling rather out of sort, and a tad uncomfortable.

“My name is Sylvia, and you are?”, She asked me extending a hand to me, to which I took lightly and shook replying. “I’m Eric, a pleasure to meet you.”. And it truely was a pleasure to meet her, if for nothing else then to simply sit in silence and enjoy her company.

“So how long have you been drawing?”. She asked me looking down at the sketch that I had been working on leaning closer to me to get a better view of it. “Most my life.” I answered her turning the book so she could get a better view of the fantasy theme drawing.

“I really do like people with artistic talent. Me hell I couldn’t draw a straight line if my life counted on it.”, and then she laughed a touch at her own admission. “Oh come on now, everyone has some talent somewhere, it’s all a matter of discovering it.” I said back finding it rather easy to talk with this absolute vision of the female sex.

“Why that is very optimistic, and kind of you the say.” She said grinning a touch looking at me then back down to the drawing. “Would you mind if I looked though your book ?” She asked, and that made me feel once more uneasy, since some of the drawings I had in the book were well, lets say very adult content, and even some that pushed the taboo limits that many would not understand, more so would find to be repulsive. “I..well..I don’t know, I would want you to see something you might find offensive.” I said trying to be both polite and discreet at the same time.

“Oh please, I am not easily offended, and that comment alone makes me want to see the rest of you sketches even more, so come on please?” it was that please and the puppy dog eyes she gave me that had me cave in, and I found myself handing over my darkest images put to paper over to her.

The first few pages were tame, random poses, the occasional landscape, a mythical creature here and there. Each one she smiled at studied, and complimented. But, I knew what was coming, and finally she came to one of my more personal mental images of a female elf, spread out in a provocative nude pose, save a wide collar about her neck. The image alone wasn’t that bad, but this lady elf came further equipped with a sizable hard cock. I looked down at the bar top when I saw that Sylvia had come to a dead stop on that drawing. I could feel my cheek reddening with embarrassment.

“Oh wow.”, she said her eyes glued to the image for what seemed like forever, and then flipping the page to see the images I had drawn getting far more graphic in content, but the subject matter still the same Shemale subjects in bondage, or being fucked to maddening hights. I dared a quick glance to her face, and I could see in her pale cheeks she was flushed. I felt terrible, but that was soon to be replaced with a different sensation. “I really like these.” She said still looking at my almost pornographic art.

“You do?” I said trying to hide the disbelief in my voice as I looked at her arching a brow. “Oh yeah. I like this one the best so far.” She said as she turned the book and leaned closer showing me the one I had drew of a shemale bound on all fours a cock ring around her fat swollen dick, and a male behind it plowing away at it’s stretched out ass hole.

I could not help but smile at that. “I like that one too, but this one is my personal favorite.” I said taking the book from her hands and flipping a few more pages till I came to one of a shemale that was not only getting her ass fucked but her mouth as well, and of course placed in some form of bondage. She looked at it and her hand went to her cheek as she turned redder, but it wasn’t out of embarrassment, and I could have sworn that even over the loud music I could hear her moan with pleasure.

Later we decided to move to an outside table, where we could talk, and not be bombarded by people or music. As she lead the way I watched her perfect heart shaped ass move under the tight fitting black dress she wore, and it took all I have to control myself from becoming overly excited, and perhaps making for an embarrassing moment for myself yet again. I pulled a chair out for her and she smiled, seems that being a gentleman has been a long lost art form for quite sometime, so this was impressive to her. Then I took my own seat across the table and smiled at her. We talked for hours, she had a few more drinks, and I could tell she was getting a bit more intoxicated. I had already sobered up sipping on a coke.

When last call came at around 2am I could see she was still in no shape to drive herself home, so I offered to take her back to my place where she could get some rest, and take it easy. She just grinned at me and winked her eye. “Oh so you can take advantage of me while I’m drunk?” She asked me giggling a little bit. “No, but I can’t lie the thought did cross my mind.” I answered jokingly, and feeling a bit more bold.

Finally she agreed, and I lead her to my car. As I opened the door for her I could feel her up against my back, her breasts fully pressed against me, and her nipples were hard as little rocks, but something else brushed against me, and at the time I didn’t think to much about it as she slid onto the passenger seat, and I made my way around the car hopping in.

The drive to my place wasn’t long, and we talked continually. I was learning quite a lot about Sylvia, and she about me. No matter what I said she seemed to take pleasure in it, and I her. To me it seemed we had been long companions and this meeting was nothing more then the two of us catching up on old times. By the time we got to my place she was leaning over against me a smile on her face and a few soft kisses had been shared between us. I could feel her hand on the top of my thigh slowly massaging the skin and flesh, and it was really making it impossible for me to keep from springing a hard on.

As I pulled into the drive way, and shut off the car she looked at me, then to my house. “Wow, you have a really nice place.” She said looking back at me. I smiled at her nodding my head. “Yeah it’s home.” I simply said as I got out of the car, and made my way around to the other side to open the car door for her. I watched as she slide out of the car, pulled the hem of her dress back down in a slightly awkward motion. This caught my attention for a moment as I lead the way to the front door, unlocking it, then inside flipping on a light switch.

I looked at her for a long moment as she looked down to the floor, then back up at me. Now I am not one to take advantage of another person while they have had one too many, but this woman was seriously tempting me to rethink that position. I lead her to the living room and she took a seat on the over stuffed couch kicking off her heels to get more comfortable. I stood there looking at her as she laid back into the soft cushions. “Would you like some coffee?” I asked her already making my way to the kitchen to put on a pot. “Yeah that would be great!” she called back to me.

As I stood there waiting for the coffee pot I heard her moving about, looking over my shoulder when she came into the kitchen. “Listen, I was wondering if you might have something for me to sleep in, or am I going to have to wear nothing at all.” she said grinning playfully at me. It was then that I was beginning to wonder who was tempting whom. “I can get you one of my t-shirts, that should work well for something to sleep in, unless you want to sleep in the buff.”... I replied back grinning at her as I poured two cups of coffee.

She giggled a little on that, but told me the shirt would be fine. So I left her in the kitchen telling her that I would be right back and headed up the stairs to be bed room. I looked in my closet for something she could wear, and just as I found a shirt that would be suitable for her I heard the bed room door slowly being pushed open. I looked back to see her standing there she was so very lovely and I could feel that pang of excitement rushing through my crotch. “I found you something to wear.” I said grinning at her holding out the over sized shirt.

“Thanks, but I was wondering if I could use your shower first? I’d like to wash off the bar smell if you don’t mind.” She asked tilting her head and smiling at me. “Sure the master bath is right through that door.” I said handing her the shirt. How could I refuse such a beautiful woman?.

She took the shirt and moved in the direction of the bath and I followed her. I pointed out where there were fresh towels for her to dry off with, then asked if she needed anything else. Her reply sort of stunned me as she said..”Well I could use some company. Since I’m in here we could” but I had the odd feeling talking was the last thing on her mind, but what the hell I was quite willing to play along. So I watched as she started the shower, and get the water to the right amount of heat for her. As she stripped, she kept her back to me at all times, which I didn’t mind she had an ass that many men would kill to get at. I put the toilet seat down and took a seat as she climbed in I could make out her shape in the fogged mirror and that is when it hit me. Slowly she turned around and from the blurred view of her I could see that this woman was no ordinary woman. She had a cock, a full hard and thick cock. For a moment I had to wonder if I was dreaming, and after a few shakes of the head I came to see I wasn’t dreaming, and this taboo princess was really in my home. It was at that point that her voice had finally filtered into my dumbfounded, but very excited mind. “Hello you still out there?” she repeated.

“Oh yeah, I’m still here, sorry must have zoned off there a moment.” I said back recovering what little composure I had left “Did you need something?”

“Yeah, I asked if you would like to join me?” she repeated not sounding so sure of herself. “Now that you mention it I would like to join you.” I said more then happy to fulfill a long time desire.

Slowly I stood, and began to take off my clothes, when I had stripped down to nothing but my skin I looked down to see my prick pulsating and harder then I could ever remember it being. Slowly I slid open the shower door and stepped in getting blasted by the hot water from the shower. I could see her looking back over her shoulder at me, and her eyes seemed to glaze over as she looked down at my rock hard eight inches of fuck meat. “My is that for me?” she asked grinning and licking her lips. I grinned back at her and feeling bolder then ever I walked right up behind her slowly grinding the full length of my hard on between the cheeks of her smooth soft ass. “Why yes it is.” I said reaching around to cup her full heavy tits in my hands, to which she let out a soft sight as I brushed my finger tips over her already rock hard nipples.

I began to move one hand slowly down her tummy, and then she grabbed my hand to stop me. I knew she didn’t want me to find her cock just yet, but I had already seen it, and for some reason I simply wanted to grip it and stroke it tease it as I ground my cock against her ass. I could feel her pressing back against my cock and slowly I leaned closer to her ear “It’s alright, I already know.” I whispered into her ear before kissing licking and nibbling along her neck. I could feel her hand letting go of mine, and once again my fingers were on the move.

It was a strange sensation to feel another cock in my hand. She must have been six, maybe six and a half inches long, but slowly I began to glide my fist up and down the length of her. I could feel her still pressing back against my cock with her ass as I slowly worked her swollen prick with my hand. “Ohhhh goooddd. You keep that up and...and I will cum.” she gasped out into the steaming shower. I just grinned stopping only for a moment to take the soap and get a good slick lather on my hands moving them back down to her engorged dick and began to stroke her cock and fondle her balls once again. “Ohhh shiiit!” she exclaimed as I began to work her with more lust, and want. I wanted to make her cum, I wanted to feel her cock pulsate in my hand as I jerked her off, and with a loud groan I felt her balls draw tight, and soon she was bucking wildly against my tight soapy fist. I watched over her shoulder with glee and fascination as the first thick glob of cum came shooting out of her meat, but I continued to jack her off till she had no more left to spill.

Slowly she turned and rinsed off and I watched her as she got close to my face, her now semi- hard cock ground against my still full erection. “I think I need to return the favor.” she whispered to me, and slowly she dropped down to her knees taking my cock in her hands and began to stroke me. I began to slowly rock my hips in time to her hand, watching as she leaned closer tonging the piss hole. God it was a sweet sensation sending chills down my spine, but that was nothing compared to when she opened her mouth wide and swallowed my cock. I could feel the head down the back of her tight throat and I could only grip her wet black hair and ride her mouth.

It must have been that way for several minutes, but as the water began to run cold we both found ourselves agreeing to continue this in the bed room. So we got out of the shower, shared a very long passionate kiss, and she took me by the hand leading me to the bed. I watched her as she lie down and grinned thinking to myself how I could have found myself in this situation. Slowly I crawled up on the bed and lay next to her. We kissed deeply once again our tongues flipping and rolling over each other. I felt her hand back at my cock stroking it, and so in kind I gripped her feeling that it had become hard again. Curiosity was now getting the better of me so without saying anything I rolled onto my back and moved her so she was straddled my face. She smiled at her and nodded as I slowly took her meat into my mouth, sucking slowly at first, flicking my tongue over the sensitive head and piss hole, then slowly she turned around and I knew why as I felt her lean forward and we had now got into a nice cock sucking sixty-nine. I took her cock back into my mouth as she took mine in her’s and for what seemed like a good solid hour we fucked each others mouths. I could hear her gasping and moaning against my cock, and me to groan deeply against her’s I knew I would soon blow my first load, and she was on the verge of her second release. Now I have never tasted cum before, but when she began to explode in my mouth I found the flavor very nice, and that sent me to grabbing her tight and thrusting my cock down her throat as I began to feel the most intense orgasm ever.

Slowly I began to come down from my sexually driven euphoria, and she was once again laying next to me. I could still taste her cum in my mouth, and leaned over kissing her very deeply. She looked at me for a moment and tilted her head after we decided to take a breath from all the kissing, and asked “How did you know?” her face was a little puzzled. “I saw your reflection in the bathroom mirror.” I answered smiling at her. “And still you wanted me?” she asked looking down our naked bodies. “Of course I did, you are a beautiful woman and then some.” I said giving her a smile a wink and soft caress on her soft limp cock.

I must have said something right because she leaned in and once again we were kissing caressing, and I could feel my cock starting to swell once again. Sylvia must have noticed this cause slowly she got up on all fours looking at me and raised her ass high in the air. I didn’t need any words to tell me what she wanted, and as I moved from the bed I could see she too had become as hard as a rock herself. I took out some lube that I had, and coated my cock nicely with it, then applied some to the crack of her ass slowly working my slick fingers into her puckered ass hole. I listened to her as she almost squealed with delight, and pushed back on my fingers. Once I was sure she was well lubed I got behind her taking the head of my cock and began to push into her tight hot ass. God I wasn’t sure if I was going to fit, but slowly I felt the head pass behind that tight clenching ring and slowly impaled her on my cock. I stopped once I felt there was no more of me left to fill her ass, and she began to grind and gyrate her ass against my hardness. God I felt like I would cum again right on the spot, but luckily I didn’t as I pulled back leaving nothing but the head. “Oh God it’s so big, fuck me please!” I heard her say, and I didn’t need any further asking as I slammed my cock deep into her ass hearing the thuds of my pelvis against her fleshy ass cheeks.

With each thrust I made into her I added in both speed and force. It was only a matter of time till I was plowing into her now loose stretched ass hole like a villain. I listened to her screaming with delight over and over as I hammered into her hole again and again. I reached up and gripped her by her hair, pulling her hard back on to my meat as I thrusted forward into her ass. I could tell I was soon going to explode into her bowels, but what I had not expected was to hear her exclaim she was once again on the edge. This only fueled me to give her all I had in me as I made to fuck the ever loving shit out of her. “Ohhhhh Fuck Eric...I’mmm I’m.... Cummmmmiiiiinnnngggg!” and I could feel her cock begin to twitch and convulse from the inside of her ass, I couldn’t hold back any longer as I felt my ball shrink and I all but growled as I felt my cock pulsating wildy in her ass sending load after thick milky load of cum into her ass.

We both collapsed onto the bed, out of breath, sweaty, and satisfied. I don’t remember moving, nor do I remember getting under the covers. But, sometime after I woke up looked around and there she was wrapped in my arms. Slowly I drifted off to sleep, and slept the sleep a babe would.


2015-07-10 21:40:33
I loved your story and the graphic details, but from a Bottom's point of view! I am a Transvestite and wish that I had had the means to go on hormones at a young enough age to be a truly feminine Shemale. I do have a Boyfriend and know the sheer ecstasy you described of cumming while being fucked and then filled with my Lovers cream!


Anonymous readerReport

2010-07-03 23:32:05
Very good.
Please write more

Anonymous readerReport

2009-10-18 19:30:08
god I wish that was me

Anonymous readerReport

2009-10-12 23:50:16
excellent story


2009-03-02 16:45:57
Thank you all for your comments. I have more on the way, possibly even a continuation of this story

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