Warning: this is a work of complete fiction, containing a transgender (post-op TS) theme. It is generally the result of a long-standing fantasy, and specifically a dream I had recently. As with most dreams, it was a series of fragments - visuals, half-sentences (one in particular) and visceral feelings. I woke up aroused by it and decided to fill in the blanks and see where it goes. I hope you enjoy it.

I originally wrote and posted this story on a lipstick fetish forum site. I finally got the nerve to share it with a wider audience.


The concept is brilliant in its simplicity, so much so that I am surprised no one thought of it before: the virtual "meet-market", a place to meet like-minded people who are looking for casual sex. Take a recently vacant office building with tons of small private offices, zoned for a restaurant on the ground floor. Place computers in each office with large screens and HD webcams. Change an exorbitant (worth every penny!) membership fee and establish a rigorous screening process (health, criminal records, social media, ...). Consenting adults - 50 men, 50 women each night - make a reservation and are escorted to their office. Browse the live feeds, chat, end conversations or block other guests as you see fit. If both parties click the "Let's meet" button, they are escorted from their office to a table, booth or barstools in the restaurant below, and nature takes its course - one meeting and you are done for the night, regardless of the outcome.

After a series of bad break-ups and a long dry spell, desire overcame economic restraint and, long story short, I found myself in front of a computer screen and webcam browsing a set of live video feeds. Other members who were engaged in conversations had the words "Currently Flirting" superimposed over their live feed. Even after only a few minutes, there were a handful of vid feeds with "Gone for the Evening" displayed in their now dark window. I completed a few rounds through the remaining vid feeds, took a deep breath and clicked the window of a pretty redhead named Molly. Two minutes and some awkward conversation later, I heard "it was nice talking to you ..." and we ended our chat, off to "flirt" with someone else. After similar exchanges with Mary (Scandinavian blonde), Lenore (African-American) and Petra (another blonde who was pissed that I hadn't noticed the "Lesbian" indicator in the status window below her video feed), I took a moment to regroup and ask myself exactly what the hell I was doing.

I had noticed a very attractive woman on each lap of the video feeds, Layla. She had short sculpted brown-black hair and was wearing a slightly plunging light pink v-neck top which showed a modest amount of cleavage. Her makeup was artfully applied, more than day-wear but certainly appropriate for a night of picking up strangers. She had light blue eyes, dramatically shadowed with long luxurious eyelashes. I also got a glimpse of long, pink manicured nails when she would occasionally rest her head in her hands. But it was her lips that made my heart race. She had full wide lips which framed a bright but mischievous smile. She was wearing a bubblegum pink lipstick with liner a couple of shades darker to accentuate the luscious shape. Rich, creamy, only slightly wet as if she had applied many coats of matte pink until the matte surrendered into a thick, moist consistency. Her lips were spell-binding and, by the way she chose to highlight them, she must know it. My kind of woman.

I noticed that she was never "Currently Flirting" each time I browsed by her, which I found odd until I noticed the "Transgender" indicator in her status window. Bummer. She was absolutely gorgeous and, given her obvious mastery of the fine art of feminine allure, she would likely be a perfect match for me, at least as a sexual partner. But I am straight, not even remotely attracted to men, no desire to play with anyone's penis but my own. So, I enjoyed one last lingering look at the lovely Layla and continued my increasingly fruitless cycling through the chat windows.

15 minutes passed with no nibbles for me and no one jumping out that I'd want to chat with. I was unconsciously comparing each face with that of Layla and found each one paling in comparison. The end of the chatting period was going to end in another 10 minutes so I decided to review my choices: give up, try to entice one of the remaining women to meet downstairs to avoid the evening being a total bust, or (much to my surprise that I was even considering it) open a flirting session with Layla for the sole reason of getting to look at her, talk to her, watch as her amazing lips formed words (must try to get her to use "o" words as much as possible!), and enjoy her smile. If I didn't enjoy chatting, I could cut if off quickly and rationalize that this was someone I shouldn't be talking to in the first place.

I clicked Layla's "Flirt" button. Her video window zoomed larger and I saw her twitch slightly as if she wasn't expecting the chat request. But that confident megawatt smile never faltered. Seeing her face in a larger window did not disappoint. I could discern the texture of her lovely pink lips and my mouth started involuntarily watering.

"Hi," she said.

"Hello Layla," I replied, "I'm Ben."

"I know, your name is on the chat window." Great, I'm a moron. "Nice to meet you Ben. Are you enjoying the evening?"

"Not really. I haven't really connected with anyone. I'm not sure I'll repeat this."

"I know what you mean. You're only my second visitor. It's been a slow, dull night for me"

Without thinking where it would take the conversation, I quickly replied, "That is so odd - you are gorgeous, with a very inviting smile."

"That's very sweet of you, Ben. So why did you wait until now to flirt with me?"

Uh, oh. I had stepped on a land mine. I was hoping to have a totally non-committal chat and within 10 sentences I ran headlong into the issue of incompatible sexual orientation. So, I deftly replied "Uh ... oh, well, I, ... I was ..."

At which point Layla mercifully rescued me with a sweet laugh, "That's OK Ben, I know. I am listed as transgender and you don't swing that way. I completely understand, not to worry. I am curious, however, why you chose to chat with me anyway."

Phew, I was off the hook regarding sexual compatibility, but Layla posed an equally valid but prickly question. With time running out on the evening's festivities, and feeling like I had nothing to lose, I told her the truth: "Well, Layla, I have a serious weakness for sexy makeup and especially lipstick, so I thought I'd take the opportunity to appreciate yours for a while. I hope you don't mind."

Layla smiled more broadly, sincerely flattered. "Thanks, Ben. I take great pride in my appearance so it is gratifying to hear that a man appreciates it."

"Absolutely. You look amazing. Captivating."

"Tell me, I'm curious. What exactly caught your eye?"

Without hesitation, I replied, "Your lips. They are simply amazing."

Layla flashed me her mischievous grin. "Ahhh, yes. I call them my man-traps."

"Interesting. Why?"

"Because once a guy comes inside, he is trapped ... pun intended, by the way."

I blushed rather suddenly at her bold and provocative statement but found myself instantly aroused at the visual. Layla was giggling now, knowing she had flustered me. She continued, "I hope that didn't shock you but let's admit why we are at this event in the first place. Why be coy? Plus, I love my lips and love what I can do with them."

Layla produced a small tube of light pink gloss and swiped a generous coat across her lower lip, pausing to reload the wand, and slowly and precisely applying the gloss to the peaks of her upper lip, all the while never breaking eye contact with the vid cam. I knew I was staring but had neither the ability nor the desire to stop. This was clearly a well-practiced move - she knew how seductive her lips were and that a casual application of gloss in front of the right audience would have a profound effect. And she knew I was the right audience.

"Wow," I eloquently pronounced.

At that moment, the two minute warning sounded, which shocked me out of my bubblegum pink reverie.

"What now, Ben?" Layla purred. "I have to agree with you that I probably won't attend this event again." She batted her lashes coquettishly at me.

So there it was. She as much as said, without having to be specific at all, that I would likely never see her again. Unless I did something right now. On the one hand, I had no intention of getting sexually involved with a t-girl, no matter how sweet and seductive. On the other hand, in a matter of minutes Layla had effortlessly turned me on more than I had been in, well, as long as I could remember. But, I don't want to lead her on either.

"I DO, however, have a surprise I could share with you, though," she said, which she punctuated with 8another swipe of gloss, followed by her tongue, across her top lip.

Before I knew it, I had clicked the "let's meet" button. After an agonizing few seconds, where I was sure I had just thoroughly embarrassed myself and would have to move to Guam to avoid the chance of meeting Layla on the street someday, she clicked hers as well.

"How does a booth sound, or would you prefer a table?" she sweetly asked.

"A booth sounds great," I breathlessly replied.

Part 2:

A few moments after the vid chat window closed, there was a knock on the door from one of the event escorts. These humorless fellows, in black blazers over black turtlenecks, guide the participants from their office to the restaurant/bar/meeting area on the ground floor. My escort politely indicated the way to an elevator bank, stepped in next to me, pushed "G", and down we went. Mr. Serious showed me the way to a comfortable and remarkably private booth adjacent to the bar area. "Smooth jazz" (whatever that is) was piped into the room, loud enough to muffle the background noise but soft enough to allow easy conversation even in hushed tones. The booth was angled facing out so that the occupants -- clearly designed for two people -- would sit half facing each other, half facing into the room. I settled in to one side of the booth, ordered a glass of red wine from the very efficient waiter, and nervously awaited Layla and parts (literally) unknown.

My gaze was trained on the elevator bank from which I had emerged so I was taken completely by surprise when I heard the unmistakable click of a pair of heels approaching from the other direction. Apparently each individual was escorted into the meeting room from a different elevator than their partner -- don't want anyone accidentally running into another potential partner. In what could only be described as a lightning-quick instance of sensory overload, I heard the heels click to a stop, just as a perfumed breeze washed over me and I looked up into the eyes of a tall, gorgeous brunette with the sexiest lips I had ever seen -- Layla.

"Hello again," she said, placing her small clutch purse on the table as she walked around to slide into the booth next to me. By the time I snapped out of my fog, thinking I should stand up to greet her, she was already seated. She smoothed her long pencil skirt with her hands (oh, those nails!), sat up straight, turned to me, locking my eyes onto hers, and said, "now what?"

Having thought of nothing more profound to say, I waved my hand (probably a bit too frantically) and the waiter glided over and asked Layla if she would like something to drink. "Diet Coke," she replied, and added just as the waiter was turning away, "with a straw, please." She turned back to me and with a twinkle in her eyes said, "You were saying?"

"I was saying how delightful it is to meet you face-to-face, uh, I mean in person. Video chat does not do you justice." And it didn't. As good as she looked on camera, she was near dazzling in real life. Not in an intimidating way, but somewhat mesmerizing. "You are lovely to look at, thus far you are charming, and you have a refreshing self-awareness and candor that is delightful. You were not the slightest bit put off by my clumsy introduction on camera and you seemed to really enjoy getting me worked up with your delicious lip gloss tease. But I have no good answer to your question, 'Now what?'."

She smiled, which under normal circumstances would have started me breathing heavily, but my confident (at least for me) reply to her snapped me back to the frustrating reality that this woman, no matter how appealing she seemed, was not what she appeared to be and that my behavior should reflect that. The waiter returned with Layla's Diet Coke and she began to idly swirl the straw with her fingertips (have I mentioned her long luscious nails?) as she thought about her reply.

"Don't worry, Ben, I am not going to try to talk you into something you don't want, or do anything overly aggressive. I enjoyed chatting with you on camera. You took the time to say Hi when no one else did, you were honest, and you appreciated the effort I put in to look good. Plus, I really got off on seeing your reaction to me teasing you -- what a turn-on for me." I was conflicted by her comment: I was flattered by her compliment but nervous that I was getting her excited. "I don't know if this will help ease your anxiety or make it worse but let's just chat a bit about a common interest and let the conversation flow naturally. Tell me, Ben, why does lipstick get you so turned on?" At which point, without ever breaking eye contact, she slowly wrapped her glorious pink lips around her soda straw and drained a healthy gulp of Diet Coke from the glass.

The instant reflexive erection was almost painful, and it was certainly distracting. I guess I should not have been surprised by it, but an insistent (but increasingly soft) voice in my head kept reminding me that this woman is a transsexual. I took a deep breath, sipped my wine, and formed my reply. "I think there are a couple of aspects. First, lipstick looks sexy. Shiny, wet, bright -- your attention is drawn to it and it makes your lips look like an enticing treat. Second, it feels sexy. I've had girlfriend's tell me that they enjoy the sensation of applying lipstick and I know I love kissing lipsticked lips." I took another sip of wine, and continued, "Plus there is nothing like the feel of creamy rich lipstick on a pair of lips as they sensuously engulf your cock." Ha! If she was going to make sexually provocative statements, I can play that game too. Of course, I was not mentally prepared for her reply.

"Oh, I know exactly what you mean."

She effortlessly parried my attempt at risqué conversation and turned it right back around on me. And she was not the slightest bit offended or put off by it. "So, look, feel -- what else?"

I gathered my scrambled wits and continued, "It's also the intent. A woman applying lipstick, especially very dramatic or provocative lipstick," looking straight into her eyes as I said it, "indicates a specific intention, a desire to call attention to her lips. She wants the world to notice her mouth, notice that she has painted it, made it feel slick and luxurious." I took another sip of wine and continued, "And when she does it in the privacy of the bedroom, she is saying that she is doing it for her partner, that she wants him aroused by the sight, the scent, the sensation of her lips. Could there be anything sexier than a woman doing that for me, uh, her partner?"

I noticed a small glaze of sexual excitement creeping across Layla's eyes as I was speaking. She paused for another (dizzyingly distracting) sip of her drink and replied "So if, for example, your lover came to bed in a sexy nightgown, smelling sweet, with bare lips but carrying a lip liner, lipstick and gloss with her, this would excite you because you know she is doing it for you?"

"Yes," I managed.

"But what about her?" I gazed somewhat blankly back at her, so she continued, "What do you think she is thinking while she is preparing to put on a generous coat of lipstick for her man, and treat him to an evening of sticky sweet pleasure?" I remained silent, eagerly awaiting her answer to that question. "She is feeling sexy and desirable and powerful and generous and a hundred other wonderful things that every woman wants to feel when she is in the bedroom. Knowing that she can elicit that kind of response from you, uh sorry, her partner," mocking my earlier slip, "is a huge turn on. And knowing that the simple act of putting on lipstick can drive him wild is a rush." She paused for a moment and leaned ever so slightly closer. "And knowing that she has the skill and desire to turn her arousal and his into a blissful, mind-numbing orgasm is beyond compare."

I will admit that I was breathing very heavily by now. I had always looked at lipstick -- and heels, and nails, and mini-skirts -- from my perspective. But knowing that all these feminine accoutrements can be as satisfying to her struck me speechless. Which amused Layla greatly. So she continued, "I told you I call my lips my man-traps. I was not exaggerating. Every guy I've ever given head to has been spoiled for everyone else. And they love it. And so do I. For some of my guy friends, I'll blow them if it looks like they're stressed out or had a bad day. And not because I am some kind of sex-crazed cumslut. It's because, like I said on our vid chat, I love my mouth and I love what I can do with it, and I love the rush of power and satisfaction I get when I use it."

She paused for a moment to let this sink in. She reached into her purse and retrieved her light pink gloss and began to churn the wand up and down to cover it with gloss before applying. She then turned to me and said, "And if I love my mouth that much, imagine how much I love making it look this tempting, this satisfying, and how much I love seeing the effect my mouth has on you."

I was paralyzed. This woman, this transsexual woman, understood my sexuality and desires better than I did myself, and appeared to enjoy her own sexuality more than anyone I had ever known. I watched, transfixed, as she touched up her pink glossy lips. She finished her application, ran her tongue across her top lip again, and then leaned in close again. "You remember how I said I had a surprise for you to entice you to come down here and meet me? Well, here it is. Yes, I am a transsexual. But I am a post-op transsexual." And then she kissed me. And I let her.

Part 3:

Wait a minute! What are you doing?!? You're kissing a guy! No you're not, you're kissing the most desirable woman you've ever met. Yeah, who's a guy! Not a guy, a transsexual. Right, who used to be a GUY! But who isn't a guy. How can that be? Well, what distinguishes a guy from a girl? Well, there's the Y chromosome, the higher concentration of testosterone, causing proliferation of body hair and heavier muscle tone, and there's .... STOP BEING A DICK! What for all practical purposes, and your immovably heterosexual identity, distinguishes a girl from a guy? Girl = vagina, guy = penis/balls. OK, so were pretty sure he doesn't have the penis/balls combo, but ...

Yeah, I was confused and conflicted, which admittedly detracted from the overall pleasure of the kiss. But not much. So silky. So wet. So sticky. Such soft but firm lips. Full and round, lots of ridges and contours to explore with my tongue. And her tongue. Long and strong. Licking outlines of my lips, fencing, winding around my tongue. Which is tracing her lips now, which means our lips have separated. How did THAT happen? Have to fix that. Lips crash back together, tongues probing through parted lips. Oh her lips. My lips slide back and forth across hers. Moans and sighs. Heavy breathing. Puckered lips engulf each other. Sweet taste of flavored gloss. Am I messing her perfectly applied lipstick? DO I care? Does she care? More kissing, oh god please more kissing ...

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byMagicif© 6 comments/ 18299 views/ 17 favorites

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