tagTranssexuals & CrossdressersHot Sex in a Blizzard

Hot Sex in a Blizzard


All flights had been canceled indefinitely because of the blizzard, so I checked in to a hotel close to the airport until the weather cleared. I showered, called my wife, and put on my standard traveling clothes: jeans and a sport coat. The restaurant in the hotel was supposed to be pretty good and as I went to it across the lobby, I noticed the bar/lounge and decided to have a drink or two first.

Three people were in the bar, a couple at one end of the bar and a single, older woman, at the other end. Nobody was at the tables. When the bartender served my drink, the couple got up and left.

I glanced at the older woman and saw she was staring at me. I stared back, looking her over. She was dressed as a businesswoman--an earth-toned skirt and jacket with a white blouse--and from what I could see of her she was slight, but built pretty well and her face was lovely, in a hard-edged kind of way. An executive secretary type--maybe even an executive herself. She had dark hair that hung straight down to almost touching her shoulders. The only jewelry I could see was some kind of pin on her lapel.

She smiled and said, "Do you know what it means when two people are staring at each other?"

I smiled back and shook my head," No."

She picked up her purse and her drink and walked over to me, a finishing school walk, poised, very classy. She was a little taller than she appeared while sitting and had a not-quite-hourglass figure. "I didn't want to say this out loud across the room,"she said in an erotically throaty voice, "but when two people stare at each other it means they are gonna fuck or they are gonna fight."

Was she coming on to me? I hoped so. She was nearly the ideal "older" woman of my jack-off fantasies.

I was shocked at the language but I chuckled and said I would remember that one.

She placed her small purse and drink on the bar, hoisted herself on to an adjoining barstool, and flashed enough thigh that I had a glimpse of the dark band at the top her stocking, and signaled the bartender to bring us a round. She held out her hand and gave me a dazzling smile, saying, "I'm Janine."

I took her hand, it was soft and warm, and I said, "Jim."

We talked about the blizzard and the canceled flights and wondered why the hotel seemed so empty. She said, "Maybe everyone's in the restaurant. I was on my way there and decided I needed a drink, first."

"Me too," I said. "And I'm starved. Why don't we find a table?"

The restaurant was almost as deserted as the bar, so there were plenty of tables available and we were seated at one of our choice, a booth, rather than a table in the center of the room. The waiter handed me the wine list with the menus; I glanced at it and handed the wine list to Janine saying, "All I know about wine was that it is either red or white and comes in two flavors: sweet and sour."

Janine laughed in her throat and swatted my shoulder, saying, "You are a funny man." She studied the wine list and I watched her expression change from "no" to "maybe" to "no" again and finally a "yes" as she went down the list. Dinner was a very nice roast beef and we washed it down with a red wine that was partly sweet and partly sour. "Not bad," I announced after taking a first sip.

She ate with gusto, table manners be dammed. I remembered hearing that women who ate like that, were the same way in satisfying their sexual appetites: with gusto. We made small talk as we ate. Janine learned that I was twenty-six years old, married three years, and had my own little software company with nine employees. I learned that she was indeed an executive secretary to the top man of a Fortune 500 company. She was fifty-one years old and had never married.

"Are you happily married, Jim?"

"Yes," I answered honestly and added, "We have an open marriage which suits us both." I saw her eyes light up.

"I have heard that term, "open marriage" all my life and I'm not quite sure what it means," she said, looking into my eyes. It was a question.

The wine had loosened our tongues

I took a moment to frame my reply. "Well, Krissi and I, from the beginning, realized we both had a need for intimate relations outside our marriage. We're both bi-sexual and obviously I couldn't supply the "woman's touch" that she sometimes wanted and she couldn't give me what I sometimes want from a man--or another woman--for that matter."

Janine leaned close to me over the table--her eyes, locked on mine, had mischief in them-- and she said, "I'm bisexual myself, Jim."

It was hard to imagine her with another woman, but very easy to imagine myself in bed with her. I had been imagining myself between her legs off and on since we met.

"I can see the wheels spinning, Jim," she said, meeting my eyes. "Look, you're a nice, attractive guy and I don't want to lead you on..." She was searching for the "right" way to say what was on her mind. "What would be your reaction if I told you that I'm really a man."

It was hard to believe. She was feminine in every way. I'm a fan of tranny porn and had often fantasized about having sex with a cross-dresser. If she really was a CD, that doubled my desire for her.

"My immediate reaction," I told her, "is that I have just had a sudden hard-on." I shifted in my seat to let my cock snake down into my pant leg. I saw a wave of relief pass over her face. "I've always wanted to have sex with a cross-dresser, and having it with you will be a dream come true."

"Really, Jim?"

"Two dreams, as a matter of fact. Sex with a beautiful older woman and sex with a beautiful cross-dresser."

"Thank you, Jim, I don't often have sex, and when I do, it has always been with someone around my age. But I have always wished I would meet a young guy--like you. I have a hard-on myself, all of a sudden. I can't believe my luck meeting you."

"The only question now is," I said, "Your place or mine?"

"I have a bottle of twenty-four-year-old scotch in my room."

We settled the bill and took the elevator to Janine's room, which turned out to be a suite. It was larger than an ordinary room with the bed at the far end and a sofa, coffee table and two wingback chairs facing the sofa.

As soon as we entered her suite and the door was locked, Janine put her arms around my neck and kissed me deeply. One of her hands dropped to my crotch and felt the hard bulge there. She broke off the kiss and took a couple steps back, and we looked at each other. We each had a bulge at our crotches. The exciting thing for me was seeing the bulge in her skirt, and I'm sure the excitement for her was having a man twenty-five years younger than she.

Janine waved me to take a seat on the sofa, and she looked into a suitcase and came out with the bottle of scotch, which was in a leather box with padding inside, which fit the bottle. She got glasses and ice and made us drinks. We sat on opposite ends of the sofa and started talking about what we would like to do with each other.

"I really haven't had any sex, for...ooo, over year I guess", said Janine. "What I like is oral sex, sucking a cock until it fills my mouth with cum, and then a long leisurely fuck with a stiff cock in my ass."

"I'm the same," Jan. I also like getting sucked off. Do you swallow?"

"Of course." she replied, "Unless the guy wants to taste his own. Then it's 'snowball' time."

I put my drink on the coffee table and moved over to her. Jan saw that and put her drink on the table, too.

I put my arm around her, pulled her close, and kissed her. Her tongue slipped into my mouth. My other hand went to her knee and worked upward under her skirt. The feel of a nylon-clad leg always adds excitement for me. Janine parted her legs to give me better access to the flesh that was hidden under her skirt. I stroked my hand from her knee to the top of her stocking. I was holding back from going any higher for the time being. The change in the texture of her stocking from the sheer lower thigh to the lacy upper band was pure pleasure for me, especially when I touched the clip of her garter belt.

Jan was having her way with me, too. She was kissing all over my face and neck, making little murmuring sounds while she unbuttoned my shirt. She put her hand under my shirt and felt all over my chest and then played with my nipples as she went back to tongue kissing. Then her hand went to my crotch where she played around with my bulge for a moment. She undid my belt, pulled down my zipper, fished around, and finally brought my cock into view. She didn't look at my throbbing manhood but kept kissing and tonguing my mouth with growing passion. Her fingers lightly touched my cock from my piss slit to where it emerged from its nest of pubic hair

Also with growing passion, I felt the warm flesh of her upper thigh between the dark band of her stocking and the bottom of her panties. I felt through the fabric her balls and her cock, which was straining for release from her panties.

I stood up with my hard cock pointing at Janine, put both hands under her skirt up to the waistband of her panties. Janine lifted her ass up and I pulled her panties down and off, sniffing the male aroma in them, and then tossing them aside.

I held Janine's legs up high by the ankles and gazed at the erotic view before me. Her skirt was now hiked up to her waist. Her cock and balls were nested in curls of dark pubic hair framed by her garter belt and the nylons on her shapely legs. She still had her high heels on. Her cock was short and thick with an inch or so of foreskin extending beyond the tip of her fully erect cock. I was like a kid in a candy store; I couldn't decide what to do next.

I let her legs down until her high-heeled shoes rested on the carpet. I dropped my jeans and briefs to the floor and stepped out of them. Then I sat beside her and took her fat cock in my hand. She wrapped her fingers around my cock, tugged it up and down a few times, and then caressed my balls.

"Oh, God Jim, I'm so fucking hot it won't take much for me to cum."

"I'm close myself, baby, I said. "I really don't want to cum too soon. Let's make this last."

"My sentiments exactly," she purred.

We picked up our drinks from the table and sipped at them. I couldn't keep my eyes off her cock. Where the long foreskin gathered itself together, ahead of the head of her cock, I saw a glimmer of wetness, which grew to become a drop of clear liquid.

Janine suddenly got off the couch. "I don't want to get my clothes mussed," she said as she began removing her clothes and hung them carefully in the closet. She stood before me wearing only a padded bra, a garter belt, flesh-toned nylons, and high-heeled pumps.

"I can't wait, Jim. Let's get in bed." She pulled away the bedspread and turned down the blanket. She lay flat on her back in the center of the bed, legs spread, her high-heeled shoes adding an erotic highlight. I got in bed at the foot and went to her on all fours, going up between her gorgeous, legs, crawled on top of her. When I lowered my head to her, she wrapped her arms around me and pulled us together. Our tongues moved around like a sword fight. Lower down, our hard cocks were grinding against each other.

A mental picture of Janine's thick cock and heavy balls was in my mind and I couldn't wait another second to taste her private parts.

I slid down her body until my mouth was hovering over her fat, uncut cock. I nuzzled around in her pubic hair, inhaled the musky scent it held, licked up the length of her shaft, and took her cock in my hand. I pulled downward and watched the pink cock-head emerge from the foreskin. It was wet and shiny when I covered it with my lips. Janine moaned in pleasure, and so did I.

I opened my mouth wider to accommodate the thick shaft as I lowered my head, taking her dick as deep into my mouth as I could. I realized that I was humping the bed as I was enjoying the taste and feel of her cock and I was close to shooting a load into the sheets. Wanting to conserve my ammunition, I raised my butt to break contact with the bed and kept sucking Janine's cock.

"Ooh, yeah, Jim. Oh yeah" whispered Janine. Then, "Suck my balls, Jim."

Sitting on my haunches, I put my hands behind her knees, and raised her legs, pushing them back until her knees were close to her shoulders and her ankles rested on my shoulders. I felt one of her patent leather pumps brush the hair on the back of my head. The view before me was intoxicating, perfectly formed and tapered legs covered in sheer nylon hose, the tops clipped to a garter belt. At the juncture of her legs was a thick, hard cock surrounded by a dense bush of dark pubic hair. Two walnut-size balls lay puddled in her hairy sack, one on either side of the saliva-wet cock, and below them a hairless ass hole, the entrance of which was a smooth, pink ring.

As I lowered my head to her crotch, I felt the nylon on her legs slide over my shoulders and come to rest when her knees were hooked over my shoulders. The stiletto heels of her shoes jabbed me slightly, just enough to make me aware of them.

I moved my head lower and tongued one of her hairy balls and sucked it into my mouth. Janine moaned and whispered, "Oh yes, Jim, that feels good. Very nice. I let that nut slip from my mouth and slurped up the other one, rolling it around in my mouth while inhaling the heady scent between her cock and balls.

After a few minutes of sucking her balls, she asked me to lick her ass. I straightened up to get the kink out of my neck and noticed that the foreskin slipped back in place, covering the head of her cock. Pre-cum glistened at the tip of Janine's foreskin. I had an idea.

Using thumb and finger of both hands, I gripped her foreskin and pulled upward. It was amazing how up far it stretched, and I pulled it open. It was like looking down a chimney with the eye of her cock at the bottom. I stuck my tongue deep into the "chimney" and swirled it around the inside of the foreskin, savoring the mild but intimate taste. Having cleaned the "chimney," I moved lower and licked her pink ass hole with the flat of my tongue. Then I stiffened my tongue and probed at the tight center of the pink ring. I licked the area between her asshole and balls. All along Janine moaned softly.

"Finger-fuck me, Jim, and suck my cock."

I had to get up off the bed and followed Janine's instructions on where to find the lube in her suitcase. After putting a little lube on her asshole and some lube on my middle finger, I watched my finger disappear into her anal orifice and worked it back and forth.

Then I opened my mouth and lowered it over her tasty member and resumed sucking. My mouth was wide open as my head moved slowly up and down the smooth shaft. My finger moved in and out of her asshole as Janine moaned her pleasure.

My jaw was getting tired and I considered stopping for a while to give it a rest.

Suddenly, Janine grunted and arched her hips upward. Her ass hole gripped my finger tighter and tighter as I felt a jet of her semen slide powerfully over my tongue. It splashed against the back of my throat and I almost gagged. I moved my mouth, leaving just the wide cock-head in my mouth. I counted five powerful streaks of cum slide over my tongue as her ass hole squeezed my middle finger. Janine grunted and gasped as her rigid body trembled and her semen filled my mouth.

Her cum was very thick in texture and had a very strong flavor, which I enjoyed. I waited until Janine finished ejaculating and her body went limp and then I swallowed her whole load. I held her still hard cock in my hand while I let my finger slip out of her ass hole.

A final white drop appeared at her piss slit and I licked it off. Then her cock deflated and dropped forward, coming to rest between her hairy balls.

I knee-walked on the bed and lay beside beautiful Janine. Her face was slack and she was snoring lightly. I chuckled. I myself often dropped off to sleep after orgasm.

I rolled out of bed with a sore jaw and a crick in my neck. I glanced at my watch and saw that I had been giving oral service to Janine for nearly forty-five minutes. I went into the sitting room of her suite--my hard cock leading the way--took the bottle of twenty-four year old scotch and took a healthy swig from the neck of the bottle.

There was no telling how long Janine would sleep. She might wake up any minute or sleep until the sun came up. I took another pull at the bottle just as the first swig was starting to spread its warmth.

I was in a high state of sexual arousal; my cock was painfully hard and I could feel the onset of "lover's nuts." No doubt about, I had to get off a load, so I began stroking my cock.

I got back in bed with Janine and furiously jerked my cock. It wasn't going to take long for me to get off. As I was on the edge of cumming, I got on my knees and pointed my cock at the dark top of Janine's stockings. My cock began to squirt and I watched it shoot ropes of cum on her stocking tops forming a long, white, wet puddle. I was breathing hard when I finished. Janine's upper thigh and the lacy top of her stocking were streaked with my white semen; some was soaking into the stocking and some was rolling off to drip on the bed sheet. I wished I had a camera.

I felt better after cumming on her leg, but I knew I wouldn't be totally satisfied until Janine sucked a load out of my cock and I shot another load deep into her pink asshole. I debated whether to get dressed and go to my room, or wait and hope for Janine to wake up in a little while.

Back in the sitting room, I mixed some of her scotch with a splash of water, sat on the couch, and turned on the TV with the remote. I got the weather station and watched a guy with a microphone and wearing a heavy parka tell me that the blizzard had become worse and would last longer than first expected. There was no possibility of any flights in a four state area for at least another day.

I grinned at the thought of Janine sucking my cock and balls and then me fucking her pretty pink ass hole. With the liquor and the recent orgasm, I drifted off to sleep while sitting on the center cushion of the couch.

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