My first shemale

Posted in: TvTs

“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual.

For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator).

The community I live in has lots of shemale beauts; maybe that started my interest. One such ravishing creature has a gallery close to my office, and I fantasize every time I see her in the coffee shop. She also has an eye popping diamond on her ring finger.

Once in a while I’d visit shemale sites. Of the pictures the ones that turned me on the most were shemales with nice, smaller-than-normal cocks and lovely shaved balls.

I’m 26 and work as an engineer consultant. I’m five ten, have a full head of brown hair, a decent enough physique with no belly. In the looks department I’m neither a head turner nor forgettable. I’ve had my share of women and I’ll leave it at that.

One day stuck at the Philadelphia airport I was sitting at a bar, nursing a drink, killing time. A leggy thing in her mid 20s, weighing no more than 115 pounds (if that). with an expensive page boy cut came in with a large handbag and pulled a piece of roller luggage. By the way she held herself you could tell this mantrap knew she was a looker. She wasn’t the only one: I think every male and a few females followed her movements.

My eyes traveled to her above- the-knees skirt of her suit and down to her sculpted, sleek legs, calves and runway model ankles. I wondered if the skirt hid a pair of those slim thighs– the kind I like and my sister always wants–the size two kinds.

I don’t know why but something about her reminded me of the art gallery shemale. Difference was this one (if she was a shemale) had a tantalizing figure, not a boyish one–even better than some dates I’ve had. Still I began to get aroused staring at her and thought it wouldn’t be a good thing walking around the airport with a noticable woody. I finished my drink and left to find my gate.

By now the seats were beginning to fill. Twenty minutes or so later I heard the unmistakable click, click sound of stiletto heels on marble floor. I looked up from my book to see this dish stop and search about for a seat. A quick gIance and I guessed she was almost as tall as me without heels. She took a seat next to me, crossed her tempting legs and fussed in her handbag for something or other. I had my first whiff of an intoxicating perfume. The little head between my legs began to stir again even as I did my best to concentrate on my book. A waste of time. All I could do was think about who who sat beside me.

Just as I debated whether to remove myself from this temptation the PA system announced our flight was delayed for twenty minutes. A good conversational opener. The auburn beauty turned to me and said, “Of course–when you want to get home.” Her voice was feminine but had a lower pitch than most females. “Yeah,” I replied. “Isn’t that the way?” Nothing else to say I returned to my book and she to her handbag.

Half an hour later someone came back on the PA and announced “we’re sorry for the inconvenience” but that the flight was delayed another two hours. A noticable groan rose from the passengers. Two hours! I couldn’t possibly sit this close to her without wanting to touch her. Best I go back for another drink. I rose and made my exit.

As I nibbled on the peanuts and nursed my second Captain Morgan who should but the object of my lust and curiosity. She scanned the room and her eyes settled on me. To my joy she approached. “Hi,” she said and drew back pouty lips to give me an engaging smile that would excite any toothpaste company. “Do you want to be alone or would you like some company?”

“Happy to have the company,” I said. (If she only knew) and gestured to the empty stol across from me. As I did I told myself to . smile back at her. She put her suitcase next to the high backed chair and clambered up in the most provocative way that quickly raised my blood pressure. Introductions were made after the waiter took her order. Jamie told me about herself, that she was a saleswoman for a national jeweler. “Is the work good?” I asked.

“Not bad,” she said as she took her first sip of the martini and I again inhaled her perfume. “It’s the money. You can make a lot but have to travel a lot to do it–more than I’d like to.”

We fell into easy conversation and discovered we both lived in Key West. “No kidding?” she said, interested in what part I lived in. I told her and found out she lived a ten minute drive from me. We wondered if we’d ever passed each other.

Two more drinks and our tongues were loosened, and to my surprise my cock behaved itself. As for Jamie, she wasn’t dumb; she caught me taking in her breasts, manicured nails, makeup, false eyelashes, everything. I’m sure she knew she had me on the line and maybe all she needed to do was reel me in.

I was still trying to puzzle out whether she was the real deal, a female. In spite of the absence of facial hair and no sign of an Adam’s apple everything said she wasn’t female. She broke into my thoughts. “You’re looking at me like a horse at an auction.”

Caught! I tried to recover but only managed to look embarrassed. I blame it on the drink but before I knew it I said, “Can I ask you a question?” She arched an eyebrow and moved over the table to peer into my face. “And that is. . .?”

“I hope you won’t feel offended,” I said and dropped my voice, “but are you, you know, what do they call it–transgendered?” She took the question in stride, giggled, put her small fingers over my hand and said, “How diplomatic of you to say it like that. Why: do you have something against ‘transgendered'”?

“No, not at all,” I replied, maybe too fast. “Besides, as they say, ‘different strokes.'” She licked her red lips and seductively said, “Would you like to be stroked?”

I had no time to answer because the PA system came on again and announced that our flight was cancelled. We were told we’d be on a flight in the morning. Everyone was given a room for the night at a nearby hotel. I had no further time to engage Jamie as the next half hour was taken up with getting our restaurant vouchers and new boarding passes for the following morning. As a result I was on a different bus when we arrived at the hotel.

That afternoon I made a few phone calls, masturbated thinking about Jamie, showered and about 6:30 headed down to the restaurant to eat. I hoped I might see her but was disappointed. Halfway through my meal she walked through the glass dooors and searched for a table. My heart raced as I waved. and hoped she’d join me. Her eyes caught mine and she gave a small wave of recognition as she headed my way.

I won’t bore you with the details of dinner, but I made sure to steer the conversation back to where it left off; before an hour passed I knew she was transgendered. Better yet, her dainty foot rubbed my ankle. Soon afterward she headed to her room, three doors down from mine and told me to knock in twenty minutes.

I returned to my room, took off my suit jacket and tie, brushed my teeth and splashed on cologne. My cock was already semi-erect when I knocked on her door. I was almost trembling with excitement as I imagined my first naked encounter with a transexual.

The door opened a crack and Jamie peeked out. When she saw me she opened it further to let me in while she moved behind it. I stepped in to inhale this newly applied perfume as she hurriedly shut the door behind me.

My mouth almost dropped when I turned and took in this goddess in a fuschia baby doll with red trim, matching thong and frilly red fuck me garter belt and nylons. On her small feet she wore pink lingerie slippers with pom-poms. I’m something of a foot man. Ohmigod, I thought as I looked at them: she carries those with her? Heaven! She’d also fixed her makeup, made her eyes more heavily lined and added a ruby red lip gloss to her lips.

“Well, what do you think?” she asked as she shifted her weight to her left hip, stuck it out and placed one hand on it like a model. What did I think? I was dizzy with uncontrollable lust. I blubbered something unintelligible. She moved closer and pressed her adorable small bosom into me and looked up. “Ooh, you’re trembling,” she said. Relax. “We’ll have a good time. Shall we start with a kiss?”

Without waiting she parted her luscious lips and offered them up. I took them and for the first time kissed a man. Didn’t matter; I was in rapture. It was amazing how nice the kiss was. The tip of her tongue made its first foray into my mouth. That was all it took: If I wasn’t hooked before, I was now as my tongue darted out to meet and deal with the intruder.

Jamie was the first to break from the kiss. She took my hand and led me to the edge of the bed. We both sat down and she crossed her legs seductively. Her hazel eyes stared into mine. “You smell good,” she purred.

“Not nearly as good as you,” I answered. My breathing was fast and shallow as one of my hands ran moved under her babydoll and cupped on of her round breasts with over her body with its puffy and erect and upturned nipple. She was soft, like a woman. I lifted the material, puckered my lips and pulled that saucy rosebud into my mouth as Jamie’s palm rubbed against my trapped cock.

At last she pulled away, peered into my face and asked, “You sure you want to do this?” I freed my attention from her breast but continued to knead it as I said, “Little late to ask. I want to suck your cock.” She giggled. “My ‘cock': you mean my pussy?”

“Whatever,” I said, feeling completely aroused. “I just want to blow you.” I had never been this forward or uncouth before, but I wanted to now, and it felt right. She didn’t take offense, just rose and stood in front of me. “My sir, what dirty words and ideas you have.” She didn’t issue another word, just moved slowly and temptingly to the far side of the bed and let me admire her high, firm and toned backside. As if I wasn’t aroused enough. I headed to the other side of the bed, threw off my clothes, my cock pointing over the bed, pulled back the blankets and slid under, eager to join this goddess.

“Got a nice package there,” she whispered into my ear as she stroked me.

“Glad you like,” I replied and let my hand follow the contour of her sexy hip. We kissed and dueled lovingly with our tongues as her hand expertly massaged the head of my wet, engorged cock. Again, I busied myself with her Lolita breasts and rubbed her already damp thong. My lips around one darling nipple I fluttered it back and forth and heard her moan with satisfaction.

In no time the room grew warm so we kicked back the blankets. I asked her to lie on the pillow while I moved down to her toes. There I nibbled and bussed them through the nylons and began my northern journey to her thighs, (every bit as shapely as I’d fantasized) and beyond. When I finally reached the end of the nylons I kissed the naked inner thighs and arrived at her thong. The muskiness of her pre-cum was strong and extremely exciting as I inhaled it through the flimsy material and had my first close look at her cock. Gold! I thought: I struck gold. My first tranny and she was every bit as exciting as I imagined.

Jamie lifted her adorable bottom and I pulled the thong past her garters and down to her feet where she kicked it off. The air almost left me as I stared at her offering in all its naked glory–an attractive, small and uncircumsized cock with the tiniest trimmed hair at the top. Her smooth and tight chestnuts looked equally good, so good I wanted to eat them. In fact I did soon enough. As far as I was concerned, given her personality and looks Jamie couldn’t have asked for a more delectable cock and balls if she went shopping for them. Everything between her legs was flawless, even though she said, “Are you sorry I’m not big down there?”

“Sorry: Are you kidding?” I said as I tucked my engorged cock against my stomach and lay down. “Size matters to everyday Joes but on you I’m not sure it’s an asset.” She lifted her head from the pillow and looked down at me. “Really? That’s not what I’ve been told.”

“Then you’ve been told wrong,” I assured her. “You look red hot, and besides, I don’t want size; I want you. You have no idea how horny I am for you.” That delighted her and she ran her fingertips along my cheek. “So you like?” I looked up at her. “Insanely.” She let her head fall back into the pillow. “You’re sweet.” she murmured. ” I’m glad you’re happy with what you see.”

Enough talk. My conquest of her body body was underway. I pressed my mouth into the soft cleft between her testicles, nuzzled and sucked. I didn’t know what they were supposed to smell like, but these were nothing like I might have imagined. I was sure I caught the hint of vanilla. She must have used some kind of lotion I thought.

First the left, then the right one disappeared into my mouth; then I bounced each of these little dainties on the tip of my tongue. I devoted myself to them. When I glanced up at her head she had her eyes closed; one hand kneaded a breast under her her baby doll, the other over her head. I’ve been around but I’ve never seen such sexiness in anyone I’ve slept with. Ever.

From her little darlings I tongued my way up the shaft of her cute little cock, pointing proudly to the ceiling. Licking, nibbling, kissing, I arrived at her bulbous and purple helmet. I pulled back her foreskin, stuck out the tip of my tongue and tasted the first bit of pre cum. Wet of course, and the hint of salt, but not the way I expected, the way I read about.

As I’d seen in pron movies I let my tongue swird around her delight. I must have been doing it right for she whimpered as her cockhead grew more purple in color. At last I brought my lips closer, opened them and slid the head into my mouth. “Ouch, ouch, ouch,” she squealed and opened her eyes. “Suck with your mouth, love, not your teeth.”

“Oops, sorry,” I whispered and kissed the offended member. I made sure my lips were extended over my teeth as my head began to bob up and down on her sex. I tried to remember what women did when they sucked me and did my best to duplicate that. Change it up I told myself; so every so often I moved from her cock down to her balls and gave them a good cleaning before I returned to her purple beast. That did the trick. “You beautiful man,” she whispered. “Oh, you beautiful, beautiful man.”

Her whole region was wet with my adoration but I was far from done. I decided to take all of her down my throat the way they did it in porn movies. After a few tries I got it right; her cock was tiny so it wasn’t hard to do.

A short breather as I pulled her cock out of my mouth, looked up at this goddess of love, the provocative babydoll punched up around her waist, her eyes closed said, “I am now officially a cocksucker–your cocksucker.” She opened her eyes, raised her head and looked at me. In a breathy voice replied, “The most beautiful cocksucker. You’ll always be welcomed between my legs.” With that she closed eyes again and pinched her nipples.

I wasn’t finished with her cock but wanted to taste everything related to her derriere, so pushed her legs up to her chest. That done I licked and nibbled the neglected part of her sack and the bit of neutral skin on my way to her anus. Jamie not only had legs and figue women would kill for, but a world class behind. I bussed and nibbled the outer smooth cheeks and pried the twin beauties apart to lick my way to her sanctum santorum. There I met the splendid, puckered opening to a different pleasure. Her purplish pink button looked so inviting as my nose inhaled its earthy aroma–by itself probably unpleasant, but in the context of great, aroused sex, wonderful. As now.

I draped Jamie’s legs over my shoulders and rimmed her lovely anus while she squirmed about. Her bottom wet from my tongue lashing I at last left it, moved north again as my lips and mouth attended to her sack. From there I worked my way back to her shaft and again found myself at her shiny cockhead. I engulfed it in my lips, opened them and swirled my tongue around as I pumped and watched it grow a deeper color. Any second I thought; any second she’ll erupt. I sucked and pumped her cock with more energy and used my other hand to travel down to her pink love button. My forefinger slid into her anus. A few more pulls and pumps on that delicious cock and seconds later Jamie whimpered, “Oh, oh . . . lov—er!” and pushed my head down into her groin.

A tiny cock but with so much cum. I didn’t think that would be possible, but she proved otherwise. Four waves of cream–she let loose: four waves. I accepted them all gladly, wanted them all but had to swallow fast to keep up with the outpour. The fact that I was sucking a cock, her beautiful shemale cock, made me even hornier.
At last she begged me to stop and come and join her. Panting we caught our breath before we kissed. “Did you like it,” I asked: “what I did to you?” She answered by plunging her tongue deep into my mouth. When she pulled away she said, “You’re amazing!”

We lay for a few more minutes before she hurried off the bed and returned with a small plastic bottle of clear liquid. She moved down the bed, got on all fours and said, “Do you want to take me?” Immediatly I knew what she meant: I didn’t need to be asked a second time. “Got a condom?” I asked.

“None, no, but I wasn’t expecting to make love to anytime soon. Haven’t taken anybody to bed since last Christmas. How about you: do you have something?”

I didn’t, nor wanted to leave and run around looking for condoms. Eight months for her. That was a long time. Good chance she was probably clean. As if she read my thoughts she said, “Have you had, done much–recently?”

“No; it’s the better part of a year for me.” She considered that for a few seconds and then said. “Ok, neither of us have been active for a while. Should be safe.” She pointed to the bottle. “We can make do with this as a lubricant.”

“Fine by me.”

Nothing else was said. Jamie put her head down on the mattress, pulled the baby doll down, wiggled her backside and let me know she was ready. I scooted behind her and kissed each cheek, nuzzled and parted the fleshy orbs, worked my way down the naturally fat insides, again reveling in the same forbidden smell as I moved closer to her anus. I easily found the pink button. Jamie purred, jiggled and pushed her backside into my face. Once more I speared her most private part from that new position, removed my tongue and stuck an exploratory finger into where I would soon head. All that produced was an increase in her moans and a new erection.

Ready: I was red hot ready, so pulled out my finger and again gave into delightful lewdness. l stuck my face back between her cheeks and sucked as if I could get her button past my lips. As I did, my right hand reached under and took hold of her cock and pumped it. “Oh, you’re golden.” she moaned; “you’re golden, but I can’t take it anymore. “Fuck me!” The command given I found the liquid, smeared her love hole with it, tossed the bottle aside and aimed my cock into backside.

I’m no stranger to anal sex so was careful and slow in guiding myself into her. Soon enough my cock was implanted up to my groin. The sensation was indescribable. I took hold of her hips and began to grind my cock in and out of her behind as she pressed her face further into the mattress. Her lovely figure, the sexiness of the baby dool, the garters that encased her behind, it was all too much. I was close to coming and she unintentionally did her part to hurry that along. She squeezed her sphincter muscles over my boner. It intensified my pleasure tenfold but I lost control and gushed my offering into her. To this day I have never come so fast and furiously as that night in the hotel with Jamie.

After I pulled out, I bent down and kissed Jamie’s round backside once more before I moved to the bathroom to clean myself. Done I joined her back in the bed. We tongued for a few moments as she brought my cock back to life. “Why do I have a feeling you’re not done with me yet,” I said and smiled.

“Would you like me to?” she said as she continued to stroke me.

“No. Not at all. What’ve you got in mind?” The answer came as she reversed herself and positioned me on my back. Next she straddled me and put her beautiful lips around my cock. I loved the feel of her silky nylons pressing the sides of my head as I attended to her balls and pulled them into my mouth. That beautiful cock though; I couldn’r resist its allure. I kissed her balls a final time and pulled her cock back where it belonged–my mouth.

We made the rudest, wonderul wet slurping noises as we sucked each other with ferociousness. Jamie came first and put another rich amount of cream into me. I took it all and wanted more. There was no more to be had so I sucked on her asshole and found some cum discharge. I tongued and cleaned that as Jamie sat up and buried my face in her behind.

I’ve had women sit on my face, but nothing as erotic as this, even though it was hard to breathe. Jamie wiggled about and pressed her cheeks down toward my mouth. I didn’t resist until I absolutely had to have air in my lungs. I slapped her right buttock and she moved forward again. She returned to my cock, licked the tip and made the head disappear. Soon enough I let loose once more; she took everything with such abandon that I thought my toes would curl.

I spent the night in her room and we did all sorts of imaginable and unimaginable things before dawn. When she thought our lovemaking was over, she moved to the bathroom. The door open I sat on the edge of the bed and watched as she readied herself to shower. I was still as randy as a satyr. As she bent over the sink to do something or other, I moved behind her, dropped to my knees and pried her cheeks apart. Without another word I stuck my face back between them and as far as I could.

I caught her by surprise so at first she flinched but soon enough she stayed bent over and held her cheeks apart as I licked everything between those wonderful globes. I had her bend over further and lavished my tongue and mouth on her anus, balls and cock. After I gave everything a good washing I turned her around and pulled her cock into my mouth as I fondled her chestnuts. A minute or so later she shuddered as I drained her of more of her love offering. When she finally caught her breath she said, “You still want more? Well, buster, you’re going to have more.”

By the time I was back in my room and showered my cock was wonderfully sore; my balls ached delighfully, as did my ass, but it was all so worth it.

Jamie and I met for a quick breakfast. On the plane we managed to get seats together near the back of the plane. As there was no one else near us we misbehaved and ran our hands all over each other.

It took some doing and she resisted several times, but I managed to talk her into going to the toilet with me. Inside I dropped to my knees, pulled down her purple thong, stuck my head under her skirt and hurriedly brought her cock into my mouth as I fondled her balls. “I never thought I’d join the Mile High Club,” I heard her giggle as one hand clung onto the back of my head and she hurriedly pumped her darling cock into my willing mouth. She made little satisfying noises and I knew she was ready before she let a more than respectable load into me.

When at last she stopped convulsing, I licked her clean and she pulled up her thong. We panted as noisily as old fashioned locomotives. When we finally caught our breath she gave me a quick kiss, winked and whispered, “You’re now my sex slave, you little bitch.”

An impatient knock on the door reminded us where we were. As we slunk out the door, a middle-aged woman she gave us a disapproving look. I didn’t care; niether did Jamie. Back at our seat she rewarded me by sticking her tongue deep into my throat, tasting herself and rubbing my erection. She stuck her tongue in my ear and whispered, “I wish I could blow you too.” In answer I looked back at the washroom She slapped my hand and said, “No!”

In Miami we exchanged phone numbers. I was ready to see her the next day.

I still go out with women but sex is best with Jamie. I introduced her to a date and we actually ended up in a threesome. Annie swears Jamie is the best sex she’s ever had. Who could argue? To this day the two are good friends. It’s hot to see the two of them in the cafe, both flaunting their fantastic legs.

To this day I cannot believe my good luck that Jamie had the right attributes and temperment for my first time. I couldn’t have asked for better–not even from the shemale at the gallery. Jamie still excites me. We still get together when we can, but we have separate lives. I’ll always thank the airline for one faulty plane.

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My first shemale, 9.9 out of 10 based on 15 ratings

One Response to “My first shemale”

  1. masterhank

    Excellent story, wish I could join the two of you for a hot time.

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