tagTranssexuals & CrossdressersAn Unexpected Surprise

An Unexpected Surprise


When I walked into the bar, I didn't notice her at first; I sat in a booth in a dark corner and ordered a drink from the waitress.

The waitress returned with my drink, and when I went to pay her for it, she said it had already been taken care of by the blonde at the end of the bar. I looked, and there was a beautiful vision, sitting on a stool at the end of the bar, in her beautiful hand was a freshly lit, long white VS-120 cigarette. God, she was gorgeous!

At this point, I guess I should relate my attraction to beautiful smoking women, for me there is nothing hotter than a beautiful woman smoking, I love watching as they take deep drags, and that long pursed lip exhale, just thinking about it make my loins quiver.

The goddess was wearing a white blouse, short black skirt, and black fishnet stockings, she sat with her legs crossed, and I could see far up her skirt. She was, without a doubt, the sexiest woman in the bar and one of the hottest women I have seen in a while.

I smiled and waved at her to thank her for the drink, which she returned with a demure smile and not followed by a long drag on her cigarette. I asked the waitress to see if she would like to join me to which she smiled, stood, gather her drink and smokes, and sexily walked over to my table, cigarette in hand. I couldn't help but notice her nipples, erect against the soft white silk of her low cut blouse, and the slow swaying of her breasts. She stood in front of me and asked if I was sure I didn't mind her company. "Absolutely not" I assured her and she slid into the booth with me.

After she was situated she asked if I minded her cigarette, which I assured her was not a problem. She then introduced herself as Nikki and told me she was a receptionist in the hotel and that she had just gotten off work a little while ago and had a halacious day and just didn't want to head home yet. I told her my name was Bruce and that I was happy to meet her.

She said I looked like the kind of man she'd like to spend some time with, at first I got worried that she might be a Pro and was just looking for a john, but she quickly anticipated my thought and assured me she was not a hooker and just wanted some company and good conversation.

As we sat and chatted and really found that we had a lot in common, cooking, the outdoors, and many other similar interests. By now she was about to light her next cigarette, to which I said, please allow me and I picked up her lighter from the table and flicked the flame at the end of her cigarette.

After an especially long drag followed by a slow sensual exhale I unconsciously let out a deep sigh. This attracted a quizzical look from her the followed are you sure you don't mind me smoking? I once again assured her that her smoking didn't bother me one bit however I could barely focus on anything but her inadvertent sensual smoking show.

She again smiled, but then pointedly asked then why the fixation on my smoking? I was now panic stricken... I had been caught by this beauty and felt like I was about to blow it, with her believing I was some kind of pervert. I was learning quickly that Nikki was very observant and somehow sensed my panic, to which she placed her manicured hand on my thigh and said it's OK, and that she was just curious.

I have no idea what calculations went on in my brain, but for some reason I felt confident that she could accept my unusual fetish. With that I said; "Well I have a secret that I have never admitted before... I have a fetish for women who smoke?"

"What" she said... "A fetish as in you are sexually attracted to women who smoke?"

"Yes" I replied...

"Interesting," she said..."I love smoking," she added, "I love the way it makes me feel and look. I guess I just never thought about it as a fetish." She pondered it for a minute, and then added, "but I can see that."

"So is my smoking getting you excited right now," she asked? "You have no idea," I replied.

She then started to trace patterns on the inside of my thigh with her long nails while she took a long deep drag and exhaled in front of me. As she stroked my leg, she slowly started to move her hand further up my thigh until it brushed the tip of my hardening cock which was growing down my pants leg. "My... I am getting to you," she said. Nikki's firm, warm breast pressed against my arm as she looked me in the eyes.

As she took her next drag, she asked if I enjoyed my partner smoking during sex, to which I replied, "I would, but have never had the courage to confide my fetish with any lover before."

We continued to talk over another round of drinks, mostly our conversation related to everyday things, but every so often she would pose a question about my fetish, which I gladly answered. All the while she smoked so beautifully that my cock was now fully erect as she continually raked her long red painted fingernails across my straining member.

I told Nikki, that I was relieved my fetish hadn't scared her away, to which she replied "we all have secrets, and that she was now getting turned on from her own smoking and knowing what affect it was having on me. I chuckled slightly say right, what secrets could a beautiful woman such as yourself have? "You'll find out, all in good time," she responded.

"Is that a promise or a threat, I quipped?" A promise I hope, she shot back.

As we were finishing our drinks, Nikki now on her seventh or eighth cigarette since joining me said, I have never said this to anyone before, and I hope that you do not think I am being too forward, but I am very attracted to you and I would love to spend the night with you.

I sat there for a second, stunned that this beautiful creature wanted to be with me. "I am very attracted to you as well and that I didn't find her advance too forward. I told her that I had a room in the hotel and that maybe we should go up for a night cap. And if you change your mind and wish to leave, I of course would understand. Her reply was that she didn't think she would avail herself of that option, although she hoped I wouldn't change my mind once we made it upstairs. Her comment stuck in my brain for a minute, but it faded as she lit another cigarette.

I said I couldn't imagine that happening. With that she stood, took me by the hand, and led me out of the bar to the elevator. Arm in arm, the warmth of her body and the scent of her perfume and of course her cigarette poised between those long slender manicured fingers was really getting to me! My cock was straining against the front of my pants, my balls tight and full.

After we got into the elevator, our arms went around each other, and we kissed a long, wet, deep kiss. Sandy's tongue probed gently into my mouth and dueled with mine. Her mouth tasted of the menthol and the strawberry daiquiri she had been drinking that night.

We lingered over the kiss, and Nikki was nibbling and pulling on my lower lip and thrusting her hips against my hard tool when we arrived at her floor and the door opened. If that door hadn't opened just then, we probably would have begun undressing each other right there in the elevator, but a hotel room service waiter entered the elevator, so we got out.

We walked down the hall to my room, and I opened the door and motioned for the beautiful lady to precede me. As I followed her into the room she took a seat on the sofa in the luxurious suite. I asked if she would like a drink, her only response was do you think we will need them?

Being a gentleman and proper host I made us two screwdrivers from the room's mini bar and said well maybe we will need some refreshment later. As I handed her the drink I slowly bent towards that beautiful painted poutty lips and kissed her slowly and deeply rekindling the desire started in the elevator. As our lips parted she asked if I would mind if she had a cigarette while we got more comfortable... as if you have to ask I said.

Nikki took her pack of cigarettes and lighter out of her purse, she took the long white cigarette from the pack and placed it between those lips that I just kissed, her dark pretty eyes staring directly at me, I was lost for a second but then realized she waiting for me to give her smoke. As the flame ignited the end of her cigarette and she took a long deep drag, my cock started its rise. As I set the lighter on the table I again leaned towards her kissing her while her exhale went into my mouth. I was now stricken with a lust I had never felt before. As I stared deeply into her eyes I nervously reached up towards her beautiful face to stroke the cheek of my goddess. As my fingers trailed from her face my hands slipped towards her firm breast tracing circular outlines for the outside towards Nikki's growing nipples. Through the thin silk of the blouse I could feel the lace of her flimsy bra.

Her breasts were clearly visible through the lace of the bra, and overflowed the top. About half of the aureole of her breasts was exposed. I cupped her breasts, and could feel there warmth and weight. She shivered when my thumbs began caressing her taught nipples, and her hand went to my crotch. Sandy firmly massaged my aching cock, and opened my zipper. She reached inside, and freed my aching penis.

She placed the cigarette between her lips in a sexy dangle and leaned back and began to unbuttoned the blouse, arched her shoulders, and slid it off. As the blouse came off her shoulders she took a deep inhale from her dangling cigarette exhaling directly at me as she withdrew her smoke with her hand and it trailed down to her breast moving her bra aside exposing here long erect nipple, and giving a gentle squeeze with her cigarette filled hand.

Nikki's other hand was now back massage my raging hard cock through my pants; I was in sheer ecstasy... my wildest fantasies were now becoming vividly true, with a real life goddess. Nikki asked me to lie back on the couch and I did. She took off her bra and leaned over me, brushing my eyes with her soft tits, and then unbuckled my pants and slid them and my underwear down over my legs. After she got my pants off, took her cigarette from the ashtray and took a long deep drag as she took my cock in her hands and blew her smoke towards my agape mouth.

She leaned forward and took my cock into her mouth, her lips gently sliding up and down the shaft, while her cigarette filled hand rubbed up and down my chest. I was in heaven, and trying desperately to focus so as not to cum too fast. Between her strokes on my cock Nikki would take another drag from her cigarette and then plunge back down on my head and shaft exhaling as she went down on me. I had never had such an amazing blowjob and with her smoking it made it 1000 times better. Just as I thought I was about to explode Nikki took her last deep inhale and squeezed the base of my cock preventing me from blowing my load. As she did, she exhaled directly into my face and said not yet baby... we have a long night ahead of us.

Again she extinguished her smoke Nikki straddled my legs pinning my erect cock between us still clad in the black skirt and stockings and grinding her hips into mine. I slowly reached behind her and with a snap of my fingers her bra let her firm breast free from their entrapment. As she ground her hips into me I massaged her breast and kissed her deeply. I could taste the fresh smoke on her breath and my pre-cum in her saliva... the mix was intoxicating.

As we broke our kiss, she stepped back away from me asking if I was ready for her secret. My only response was a hungry nod of my head; the amazingly beautiful woman had me completely mesmerized. I would have done anything she asked. With that she asked me to close my eyes, as I did so I heard her take a step back and she then said, if you can't handle my secret I will understand and just leave. I began to assure her that I wouldn't want that, but she hushed me and said wait before you answer. I was now more intrigued more than ever, I waited with the anticipation of a small child waiting for an ice cream cone.

I heard Nikki take a step towards me as she began unzipping her skirt letting it fall to the floor. I then heard the familiar snap of the elastic expanding and being pulled down her legs. Nikki took another step towards me and I could smell her light exotic perfume and her musky sensual aroma.

See then ordered me to open my eyes and she took a step back away from me... in the dim light my now refocusing eyes were trying to figure out what I was seeing in front of me just out of my reach. As I began to focus on her eyes, she waited in anticipation for my response, I looked down her body, over those beautiful breasts that I had just fondled and then down to her crotch... and there it was, swinging slowly back and forth, a big COCK!

At first I shook my head, thinking it must be an illusion of the light and shadows, but as I refocused I knew that it was truly a cock... At first I was a bit shocked, to say the least! It was semi-erect which told me this was not a strap-on, it was an honest to god penis staring me right in the face. It looked like it would be about seven inches and thick... I had seen pictures and heard stories of the "she-males," and I must admit that I was more than curious, but had never dreamed I would meet one, and that she would be such a beautiful Woman!

To say the least I was stunned, and she began to get worried that I was turned off, and she began stepping farther away from me. As she did she said, "I am so sorry, I should have told you, but I just didn't know how to." As she began to bend over and pick up her skirt, I said no, I understand why you wouldn't have please don't dress, I just need a few minutes to process this.

I was so overcome with passion, before this I believed her to be the perfect lover, she was beautiful, exotic, was willing to indulge my strange fetish for smoking, and had turned me on like no one ever has. And the actions of her mouth and tongue on my cock had left me wanting to be fulfilled, and then in an instant, just as I had earlier in the evening I said I am ok with this, I am infatuated with this goddess and I have to at least see if I could make love with her. While I had never had sex with a man I decided to just let it happen.

I motioned for her to step forward, I looked into her eyes, trying to reassure her I wasn't angry and was not going to hurt her, as she tentatively stepped forward I reached up and touched a cock other than my own for the first time. As her now flaccid cock slipped over my palm I realized it felt much like mine, but maybe warmer but smooth and soft. However that didn't last long, as I stroked her she began regaining the hardness that I had seen when I first saw her cock. Just as her body was her cock, and balls were completely hairless save for a thin landing strip of pubic hair that rose about two inches from its base towards her pelvis. She was uncircumcised, and the head of her cock was swelling up out of the foreskin, purple and moist. I brushed it back and forth in my hand almost but not quite examining it like a doctor. As it grew I began lowering my lips towards the now bulging head of her fuck stick. Nikki placed her hand on my cheek and asked are you sure you're of with this? I grinned and said well I guess we all have our secrets, even if we didn't know about them. We both laughed and she took a step closer to me and I felt the tip of her cock slowly cross my lips... I told myself well there is no going back now... As she slid deeper onto my tongue, I could taste the slightly salty taste of the drop of pre-cum hanging from the hole. It was delicious, and I found myself wanting more, so I slipped it into my mouth.

As I began to suckle her I slowly tried to figure how to orally service this strange cock, just as Nikki had done to me minutes before. I tentatively cupped her testicles in my had, and gently massage them.... and ran my tongue over heard purple head and in her piss slit as she had done for me. Nikki's hard cock as now at its full length and thickness and I had now idea how I was going to get more than a few inches in my mouth, but with a little coaching from Nikki, I was doing quite well taking a good amount of her hot cock in my mouth. I wasn't able to deep throat her as she had done me before but then again this was my first cock.

As I sucked her, Nikki was in ecstasy, moaning lowly and calling my name... yes Bruce, I love your mouth on my pussy stick... oh baby, that's it... mmm... Daddy, that feels so good... Just as I was getting the hang of sucking her cock, Nikki reached over to the end table and withdrew a long white cigarette from her pack. Since my hands were otherwise occupied, Nikki lit her own smoke... the flick of the lighter rekindled my own passion and my now semi-erect cock began to inflate once again...

Nikki smiled at me and exhaled directly into my face now servicing her hard cock... as she did she opened her legs and said play with my ass baby... now this is something I had done before, although with a genetic woman. So now I took one of my hands from around the base of her cock and used the saliva that had been built up from my up and down motions on her cock and began rubbing it gently around her hot little rosebud.

Taking a breathe I suggested we switch places so that I could fully please her... As I stood Nikki stepped into me kissing me deeply with her cigarette hand resting on my cheek. As we kissed, I felt another sensation, that of Nikki's hard cock sliding up against mine... again I sighed... as I thought about how beautiful this woman was and how much I wanted to please her... I knew she could please me... she had proven that by bringing me to the brink earlier.

As our tongues thrashed in some superiority dance our cocks slid back and forth with each other driving us both into a complete sexual frenzy. As Nikki stepped backwards into the luxurious sofa, I again took her in my hand and hungrily moved my mouth towards her hard cock... As I did, Nikki took another drag on her smoke exhaling into a cloud above her head with a deep moan. I then began my learning on pleasing another cock, I took her deep in my mouth and sucked harder and softer, while running my tongue over her head.

I also once again began playing with her ass... now that she was sitting I had full access to her wanting hole... I also began kissing and licking down her thick shaft and on to her bells while I continued to pump her with my other hand.

After taking each one of her balls into my mouth and rolling them around with my hungry tongue, I moved my mouth to that area where her pussy should have been... when I ran my tongue up and down her non-existent slit she cooed and moaned deeper. I know went for her bud... again I have tongue the ass of a lover before... but this one I wanted more than any lover before.

My finger spread her man pussy open and my tongue lightly danced across and around it, with little darts into her in recesses her hips began to wriggle... after minutes of this Nikki, gasping and pleading begged me to fuck her... "I want to have your cock up my hot boy-pussy", she murmured as she pulled me towards her opening lips... by now Nikki had forgot about the cigarette in her had which had burned almost down to the filter... As I approached her lips she took one last drag and exhaled directly into my mouth, as we broke our kiss smoke drifted from both of out moths and she put out her smoke. With her hands now free she reached around her spread legs and grasped my raging member and drew it towards her open hole... between my ministrations on her hole and the slick pre-cum leaking from my own cock there was more than enough lube.

Nikki looked deeply into my eyes and said now push into me slowly please... it has been a while sense I have had something this size in me. As Nikki guided my hard cock towards her hole I pushed gently while she bore down and opened he man-pussy for me. As she let go my cock was drawn into her like a conveyor was pulling me in... Each time I withdrew she repeated the process until I was deep in her to the hilt... In my entire life I have never felt anything as tight or lovely as this woman's ass... it rested to allow her to get used to the wanted invader, gently fondling her tits and kissing her. As we kissed Nikki said OK baby, give me what I want, fuck me baby... fuck me.

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bythe_jackal1962© 9 comments/ 85410 views/ 38 favorites

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