Fine by Me

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First Date with a Transwoman.
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Rimbaud17
Rimbaud17
575 Followers

*The following is based, fairly closely, on a true story. I'm not saying that it happened to me. But I'm not not saying that, either.*

***

The motel parking lot was still half empty when I pulled into a space a couple of doors down from her room. I had been surprised she had asked me to book a room at this somewhat downscale chain motel; I would have gladly popped for about anything she had asked for. But she said she didn't like going through lobbies and past registration desks. Fine by me.

I turned off the car and turned to look at her. She had been pretty quiet during the fifteen minute drive from the restaurant. Of course, she had been fairly quiet at dinner, too. Part of it, I hoped, was just the fact that English was not her first language. I mean, she spoke English plenty well enough to be finishing graduate school in engineering at an American university; it's not like we could barely communicate. But there's a difference between the structure of the classroom and the casual idiomatic language of dating and seduction.

And Lord knows I don't speak Croatian.

At the moment, I was wondering whether she had gotten cold feet, or, worse, was just feeling half-hearted about proceeding. I almost asked her, "May I come in?" but felt like that was too black-and-white. So I said, "Shall we go inside?"

She nodded, and opened her door to get out. I turned around to retrieve the little picnic basket with the wine and fruit which I had packed, and then followed her.

Walking toward her room, she appeared taller, more confident, more purposeful than she had all evening. I noted the way her heels clicked on the sidewalk, the distinctive, pronounced... practiced... heel-toe, heel-toe of her gait.

Once we were inside the room she turned to face me, barely giving me room to get inside the door without invading her space. So I invaded. In her heels she was almost as tall as I was. She had appeared much smaller in the restaurant, and especially in her pictures. I put my hands on her waist and she draped her wrists over my shoulders, and I kissed her. I was surprised and pleased at how quickly the kiss developed into something more sexual than romantic; how willingly she parted her soft lips, slightly tacky with recently-reapplied lipstick; how aggressively she penetrated *my* mouth with her rigid tongue.

I ran my hands up her sides, under her stylish waist-length jacket, feeling her body through her silk blouse and, apparently, a chemise or camisole beneath that, stopping short of her breasts. Through the fabric I could feel her warmth; and the softness of her skin over a body that felt lean and lithe.

This was more like it, I thought. It occurred to me that maybe the dinner date had been solely for *my* benefit. She had agreed to this evening together solely for the physical intimacy, the masculine attention.

Fine by me.

I realized that we had slowly turned in a half-circle during our kiss, and suddenly the edge of the bed was pressing against the backs of my knees. Mila moved her hands to my chest and pushed me back with a smirk, and I dropped into a sitting position. "Well, then," I murmured.

She gave me a bit of a Mona Lisa smile, and shrugged her shoulders out of the jacket she had worn throughout dinner. She stepped forward, straddling my knees with her stocking-clad legs, her satiny black skirt brushing across the tops of my thighs as she drew closer to me. But just before I planted my face into her chest, she pushed me back again, so I was l on my back on the bed; and then she lay down on top of me and her lips sought out mine again.

I felt her weight on me and realized that I was already hard as a rock.

And so was she.

I ran my hands down her sides and cupped her firm, narrow buttocks, pulling her upwards and thrusting my own hips up to meet her, feeling our cocks grinding against each other through several layers of fabric.

It was the first time that I had ever been with a transwoman. Or a t-girl, a term which I avoided until Mila used it herself. She had started the hormone treatments six months ago. To her friends and professors on campus, and to her family back home, she was Petar, a quiet and studious young man from the suburbs of Makarska. Only in private, and on the internet, and in out-of-town liaisons like this did she allow herself to be Mila.

How did I get so lucky?

Most people look better on the internet than in person, posting only the most flattering pictures of themselves. It was true for Mila as well, I had to admit; although I had found myself appreciating the reality of her more than I had the mere fantasy. She had voiced concerns about being "passable" enough. She was certainly passable from across a room, where her shoulder-length blonde curls, smoky mascara, and long legs were the first things I had noticed. From across a table, one might notice a slight prominence of her brow, her larger-than-average nose, the bit of an Adam's apple. But then, the fact that she was a young person who had grown up as a boy and was now choosing to be a woman, was in fact what was intriguing to me. Fascinating, really.

I wondered how it felt to want *anything* enough to do something as drastic as transitioning from male to female. I fancied being desired by someone who could act so dramatically on desire.

I rolled her over, felt her thighs come up around my waist, held my weight on my elbows and looked down at her. I put my right hand on her cheek, touched her lower lip with my thumb, and stretched my fingers up into her blonde hair.

"Be careful," she said. "It is a wig."

I nodded my understanding, my acceptance, suddenly touched by her fragility, and eager to let her know that no "illusion" had been spoiled. I kissed her again, this time more gently than our earlier kisses. She let herself give a little moan into my mouth.

Then her hands were pushing up against my chest again, and I gave her room to scramble out from underneath me. She stood up, and raised her chin, and from my vantage point she looked quite tall indeed. She arched her eyebrows, and informed me in her slight Slavic accent, "I want... to undress for you."

"Fine by me," I said out loud. I sat up on the bed and gave her my enthusiastic attention. She took up a stance halfway between me and the dresser mirror, where she could watch both me and herself.

She had dressed for our date in several layers of black and gray. Her leather jacket had already come off. Her blouse was a shimmering dark silvery fabric, almost gun-metal. She slowly undid the buttons down the front, locking eyes with me as she did. Underneath she wore a black chemise, and I could see the straps of yet another item under that.

She turned away from me to watch herself in the mirror as she gingerly lifted the chemise over her golden locks, revealing a matching lace bra. Then she reached to her side and loosened a hidden button on the waistband of her skirt, then slid the zipper down until the entire garment fell off her narrow hips and dropped into a pile at her feet. I watched in the mirror, too. She was wearing stay-up thigh-high hose, and a pair of high-cut black panties that hit her above her hipbones and then plunged down to an intriguing pouch between her thighs.

She turned back toward me and reached up behind herself to unhook her bra. The shallow cups fell forward, and she let it fall to the floor.

She had the smallest breasts I had ever seen in person. The pink areolas were puffy, but the hard little nipples in their centers were smaller than pencil erasers.

She cupped them in each hand and presented them to me. "Do you like them?" she asked.

"Yes," I replied, automatically, although in truth I found them disconcerting. They reminded me of the breasts of a pubescent girl.

"I am so proud of them," she informed me. She gave them a jiggle to which they barely responded. Huh, I thought to myself; and took another moment to take in the entire nearly-naked body of the woman in front of me. Of course she was proud. These were the breasts of a young adult with the courage of her convictions. I felt the blood rushing back into my penis again, and liked it.

I got up off the bed, waiting for her subtle nod to give me permission to approach. I took a seat on the corner of the other queen-sized bed in the room, and she moved between my open knees, still proffering her breasts to me. I leaned forward and inhaled deeply. She smelled of moisturizer and perfume. I flicked at her left nipple with my tongue, then made a seal around that breast with my lips. I felt her hand move to the back of my head.

"It is okay," she whispered. "You can be harder."

I placed my hands around her waist, aware of the firmness of her muscle under the soft half-inch of flesh, of the relatively straight line between her hip and her rib cage, the figure that she didn't have yet but that I knew she aspired to. I relished the way she was.

With her nipple still between my lips, I looked down to where her penis was beginning to peak out of the top of her panties. I moved my fingers down to the waistband, and then looked up at her. She nodded yes.

I hooked my fingers into the elastic and pulled down and toward me, allowing her slim erection to pop free and bounce up against her flat stomach. And there it was. Pale and smooth and lovely, uncut, but with the tip of her pink glans peaking through her foreskin opening. A tuft of sandy, neatly-trimmed hair above its root. Two delicate testicles in a soft-looking, hairless pouch.

I wrapped my hand around the shaft, almost enveloping it; warm and soft to the touch, but enticingly hard just underneath when I gave it the slightest squeeze. I gently pulled her foreskin back, just barely, just enough to see if I could without hurting her. The moan she emitted was not one of pain.

Nevertheless, she reached down and grabbed my shirt at the shoulders, breaking my trance. "We need to get you out of these clothes," she insisted. I agreed, and stood up, and started to unbutton my dress shirt, but she brushed my hands away and did it herself. I realized she was still almost as tall as me. She was still wearing her heels -- ankle boots, actually -- and her black thigh-highs, but nothing else. And I was getting ready to join her.

She pulled off my shirt and tossed it behind her, then let me pull my own t-shirt off. She dropped to her knees in front of me, and placed a hand on the back of one of my calves. I understood the gesture and she waited while I kicked off my loafers. Then she looked up at me and gave me a grin as she moved her long fingers to my belt.

I put my hands on my hips and watched her work the buckle, the button, the zipper. By the time she pulled down my slacks and my boxers in one smooth move, I was fully erect, too.

She stood back up. With her heels on, our penises were at the same level. She loosely wrapped one hand around both of them, palm up, so I -- we -- could enjoy the view. She gave an audible sigh of pleasure. I know I'm simply average, size-wise; but I liked seeing that my member dwarfed hers. I especially liked the impression that she liked that, too.

Then she pushed me back again, onto the other bed this time, and climbed back on top of me. This time, we were both virtually naked. I could feel my heart pounding in my chest. There was nothing between our dancing penises, nothing between MY urgent cock and the inviting, forbidden crevice behind her testicles.

She licked my upper lip with her tongue, one teasing kiss, and then jumped back up again.

"Open the wine," she said, and quickly headed toward the bathroom. "I will be right back."

I complied. She wasn't right back, though. It occurred to me to perversely wonder whether she was peeing sitting down or standing up, but I banished that thought from my mind. I opened the bottle and filled two plastic glasses, and took them both to the nightstand between the two beds. I settled back against the headboard, self-conscious in my nakedness.

A minute later the bathroom door opened. She stepped out, fully dressed again. This time, in a shimmering silver mini-dress and thigh-high white boots. She struck a pose.

"Do you like?" she asked.

"I do," I answered, honestly. It dawned on me that for her, dressing was half the fun.

Fine by me.

She twirled for me. I noticed how her boyish hips were not yet wide enough to show off the dress to its full effect; but that when she turned sideways, the curve of her backbone to her bottom was rather spectacular. And she seemed to have lost her erection. That was fine, too, although I hoped I would get the chance to bring it back.

She walked over, picked up her glass, and took a sip, then gestured for me to scoot over so she could sit beside me.

"I feel kind of under-dressed," I joked.

She gave a shy shrug, and reached down with her free hand to poke at my knob with one finger. "It is all right," she said. I noted once again, for the tenth time since dinner, how she almost never used contractions. I was finding it increasingly exotic and adorable.

Then she was bouncing up again. Again! This was getting frustrating.

"Will you take some pictures of me?" she asked, taking my affirmative reply for granted as she walked over to her suitcase to retrieve a digital camera.

And so for the next several minutes, that's what we did. With her standing, looking back over one shoulder, sitting, reclining. I snapped away as she moved from pose to pose, sometimes laughing, sometimes pouting. I scarcely noticed that my erection had flagged to half-mast. She didn't seem to mind.

"What is that song?" she suddenly asked. I hadn't realized I had been humming out loud. I laughed.

"These Boots Are Made for Walking," I answered, although I instantly thought that in fact, *these* boots were made for fucking. I didn't say that out loud.

Mila gave me a blank look. She didn't know who Nancy Sinatra was. Oh well. She had turned away from me and lifted her curls away from the zipper on the back of her dress, inviting me to take it off of her. I happily unzipped her. For someone who had been so quiet at dinner, she was certainly getting comfortable calling the shots here.

I helped her step out of her dress, and this time I took a moment to fold it neatly and lay it down on the dresser. She had started to turn back toward me, but I placed my hands on her shoulders and turned her away from me again. I unhooked her bra -- this one was white -- and then I kissed my way down her spine to the waistband of her new white bikini panties. And then lowered those, too, giving a little nip to one cheek, which made her giggle.

Then I let her turn around to face me as I stood again. She was naked again except for her spectacular boots, and hard again as well. As was I.

I embraced her, pressing myself into her nakedness, and she welcomed my kiss.

Then she asked me, knowingly, "You want that I should leave the boots on, no?"

Oh, yes.

Again, she pressed her fingertips against my chest and wordlessly instructed me to fall onto my back, knees at the edge of the bed, feet still on the floor. Again, she straddled me. Her knees beside my waist. Faux-leather boots feeling cool against my hips. She leaned forward and we kissed some more, slow, rewardingly sensual. Her hands in my hair, my hands on her firm bottom. Her slim erection hot against my own cock.

Then she put her hands on my chest again and pushed herself into a sitting position.

I could feel the pulse in her perineum against the tender underside of my cock. I could feel her pressing her weight down onto me, onto my shaft. She had her head back, eyes closed. I looked down to where her penis was bobbing, where the little twin globes of her balls were gently rolling in the smooth, soft pouch of her scrotum, massaging me just below my frenulum. My glans was engorged and purplish. And maybe three inches away from the little opening behind her testicles.

"Mila," I whispered. We had agreed on no penetration.

"Shhh," she replied. "I just want to grind on you a bit. Is that okay?"

Okay, I nodded. Fine by me. I realized that my hands were on her waist. I moved them up, over her ribs, cupped her little breasts, pinched her tiny nipples, then moved down again.

We really were dry-humping, I realized; with no lubrication except perhaps a slight amount of sweat, it was, for each of us, our own skin moving back and forth over the spongy erectile tissue beneath that we were feeling. Probably a good thing; I imagined that if lube was involved, I might be spurting onto my stomach by now.

Eventually she scooted back a few inches, so she was no longer sitting on my cock, and she reached down and wrapped her right hand around our penises. Her nails were painted a shade of burgundy, but I couldn't help noticing that they were neither delicate nor small, and I felt another shiver of eroticism... as if the warm slender penis that she was pressing up against mine wasn't evidence enough that she was no typical young woman.

She murmured something I didn't understand, and I wondered what the Croatian word for "frotting" was, but I was mute with fascination. She was squeezing and releasing our cocks, the fleshy undersides compressing each other, and moving her hand up and down, just enough to draw her own foreskin back and forth over her pink knob, which was beginning to glisten. She had me at a disadvantage. I had no such foreskin.

As if realizing that, she licked her left hand, and then replaced the other hand around our shafts. It wasn't much lubrication, but it was enough to feel very, very good. I wondered if she was hoping to bring me to orgasm this way, or herself, or both of us. I wasn't ready yet.

And then she was up again, standing between my knees, deliciously naked above her knee-high boots, smiling at me. I got up on my elbows, but she shook her head, dropped to her knees, and wrapped a hand around my cock again, pointing it toward the ceiling, before lowering her mouth to it.

The sight was electrifying, at least equal to the sensation as she kissed and then licked the tip of my glans, then began to drag her pointed tongue down the underside on one side, and back up the other. She made eye contact with me, and grinned at what must have been my goofy expression of bliss and gratitude. Then she engulfed my knob in her warm, wet mouth.

You know the old joke about how only a person with a penis knows how to really please a penis?

Well, apparently it's not true.

I mean, I wasn't going to complain, but after a couple of minutes I began to get the distinct impression that this blowjob was perfunctory; that it was something she felt obligated to do, not something that excited her. And I was surprisingly okay with that. I wasn't ready to cum yet anyway.

It dawned on me that most of the sex scenes I had read, and participated in for that matter, had been pretty linear. From undressing to fellatio to cunnilingus to female orgasm to penetration to male orgasm. I was already aware that our encounter was becoming circular, or maybe rather random. And it was just beginning.

I pulled her up and she mounted me again. I rolled her over, felt her thighs come up around me, felt her boots grazing my hips. I realized that in this position, I could for the first time see us in the mirror. The sight was spectacular.

I kissed her again, and again. Our tongues dueled; her arms crossed behind my neck, drawing me to her. Her hand snaked down between our bellies, grasped our penises together again. But then she brought her knees all the way up to her chest, and my cock slipped from her grasp. I lifted my left arm and then my right, allowing her to hook her legs over my shoulders, her boots against my ears, the toes pointed to the ceiling.

I realized that my cock was stroking up and down the length of hers now, up and then down, down past those delightful little balls, until at the bottom of each stroke I was nudging at her tender taint, an inch away from her puckered little asshole.

Rimbaud17
Rimbaud17
575 Followers
12