tagTranssexuals & CrossdressersCrossing Over the Line

Crossing Over the Line


The telephone directions led me to a nice, gated condo complex in the upscale village of La Jolla, a beach community adjoining San Diego. Another phone call at the entrance yielded the gate entry code, her condo number and more directions. I drove into the complex, past the clubhouse and pool, along narrow, winding roads shaded by the abundant trees. It was a clear, brilliant day; the sun almost directly overhead at 1 P.M.. I slowed as I approached her building, one of many identical, vaguely Spanish style stucco and red-roofed structures in the complex.

It had started two weeks earlier when I came across her name while perusing a web site called "The Erotic Review," a site that provides information, including client reviews, of those who offer adult services in every major city of the country. Her name was Katherine and she had received consistently high marks and rave reviews. The link to her web page led me to several striking photographs of her. Tall and slim, she had the figure of a Victoria's Secret underwear model, full lips, dark brown eyes, blonde hair and a very nice smile.

Her web page described her as a Latina, in her mid 20's, five foot - eight and 120 lbs.; and emphasized how easy going and friendly she was. Katherine was about giving pleasure, her web page said, without attitude or agenda. She offered a true "GFE," or Girl Friend Experience in the lingo of the trade. Her reviews bore out the truth of her web ad. One after the other raved about her skills, passion and desire to please.

It took me a while to gather up the courage to write to her. I described myself accurately as a middle aged white guy, six feet tall, about one hundred and seventy pounds, with hazel eyes and sandy, light brown hair. I wrote truthfully that I had never had any experience with the type of services she provided, but I had often fantasized about it and the fantasies had become more frequent and urgent of late.

I explained that I was no novice when it came to obtaining services from a provider. As a sexual submissive I had visited professional dommes several times in the last few years. My favorite activities were strap-on play, light bondage - including CB bondage and intimate body worship. I had found a great domme in San Diego and saw her fairly regularly; whenever the urge became so insistent that it could no longer be ignored. I enjoyed those visits immensely, but of late there seemed to be something missing from the play; something that I had a powerful urge to experience, at least once. I thought Katherine was just the right person to provide me with that special experience.

I found a parking spot near her building entrance and then took a couple of deep breaths before shutting off the engine. I was a few minutes early so I closed my eyes, took several more deep breaths and tried to focus my mind on the decision I had made. Even as I sat there, I did not know whether I would, or could, fully go through with it. Having never had that kind of experience before, I did not know for sure how I would react when the moment of truth came. I reaffirmed though two promises I had made to myself before setting out for Katherine's place that afternoon. First, I would not do anything unsafe. And second, I would leave myself open to the experience and simply follow my feelings at the moment, without making arbitrary, moralizing judgments. It sounded right in my mind, but it did little to calm my extreme nervousness.

My hand shook as I exited the car, went to the trunk and transferred the bottle of chilled Champagne into the gym bag I had brought which already contained several items I thought would be useful for the session. I had told Katherine that I would be very nervous and would bring a bottle of wine - thinking a little conversation over a glass of wine at the outset would help settle me down a bit and get me to relax. I figured Champagne was appropriate since it was often used to mark special occasions - and this was certainly going to be a special occasion for me.

I found the door and knocked twice. I heard the sound of footsteps, a short pause as she eyed through the peep hole and then the click of the door lock being opened. The door opened just a crack and a pair of dark brown eyes peered out in the narrow space.

"Come in," she said in a whispered, little girl's voice, as the door swung open.

"Thanks," I said as I stepped into the condo apartment.

She closed the door quickly behind me and bolted the lock. She came back around in front of me, a vision of loveliness in a tight, figure hugging tank top, short skirt, black stockings and heels. She had changed her hair color - it was no longer blonde. It was now a dark brunette. Falling in soft waves below her shoulders, it looked more natural than the blonde color in her pictures.

She was tall and slim - in her high heels, perhaps just an inch or so shorter than my six foot height. Her arms were long and very thin; her hands quite delicate looking with long, well-manicured finger nails - colored a dark pink, matching the shade of her full lips, as best I could make out in the dim light. Katherine's legs although slim were very shapely, their length accentuated by the short skirt and high heels. The only feature of hers that was not slim was her bust which was large and almost perfectly rounded; her substantial cleavage clearly visible from her tight, low cut top.

She stepped up close and put her arms around me; then kissed me on the side of my neck as she murmured, "welcome Kelly."

"Tha . . . Thanks Katherine," I stammered, senses suddenly overwhelmed by the warmth of her body, the softness of her touch, her gentle voice and the scent of her perfume.

"Please come over here and sit down," she said softly, leading me by the hand to the couch in her living room, just inside of her entry foyer. The room was dimly lit by a single, small table lamp opposite the couch; the vertical blinds closed against the bright afternoon sun.

I put my gym bag down on the glass coffee table as she lead me around it to the corner seat of the couch. I sank down into the softness of the couch's seat and back as I sat, Katherine still holding my hand.

"Can I get you something to drink Kelly?"

"I . . . I brought some wine, . . . some Champagne actually. Please have a glass with me," I said as I leaned over the coffee table, retrieved my gym bag, opened it and took out the chilled bottle.

"I'd love to," she said, taking the bottle from me and then disappearing into the kitchen.

I heard the sound of cabinets being opened and the clink of glasses as I opened the side pocket of the bag and removed the white envelope I had brought her. I laid it on the end table next to the couch, in plain sight. The flap was closed but unsealed. I had put a little extra in it, wanting to make a good first impression.

I was just closing up the bag when I heard a loud "Pop." Startled, I flinched but quickly realized it was only the Champagne being opened. I sat back into the soft confines of the thickly pillowed couch. Feeling beads of sweat on my forehead, I pulled a handkerchief from my pocket and daubed it dry. I felt warm all over but especially my face. I could feel the heat of my flushed face, the skin seeming to pulse along with my rapid heartbeat. I was clammy all over, my face and palms unable to stay dry.

I knew I would be nervous and dressed accordingly in a loose "Island" type button down, short-sleeved shirt, khaki pants, socks and loafers. I took the precaution of putting on a heavy layer of antiperspirant under my arms. The beads of perspiration rolling down my sides obviously revealed the futility of that measure. Knowing I would be nervous was one thing, but doing something about it was quite another, I thought to myself as I noticed a tremor in my left hand.

Katherine returned carrying a small tray in front of her - the bottle of Champagne, two large wine glasses and a short stack of cocktail napkins just fitting on its round surface. When she reached the coffee table she bent at the waist and set the tray down on it, her long, dark hair falling in cascades down past her shoulders. Still bending over, she picked up the bottle and slowly poured the Champagne into one glass, several times waiting while the foam settled, then continuing to pour until the glass was nearly filled to the top. She then filled the other glass but only about half way.

As she poured out the sparkling, golden liquid, I enjoyed the vision in front of me - her large cleavage well below my eye level allowing a full view of her charms. With my attention elsewhere, I hadn't noticed when she finished pouring the second glass. She looked up and caught me staring, eliciting a small, knowing smile from her and an embarrassed glance down at the floor for me. When I looked back up at her, I just caught her glance over at the white envelope I had left on the side table. A larger smile crossed her face as she looked back over at me while she came around the coffee table and took a seat beside me.

Actually, she didn't really sit on the couch - she turned sideways towards me, slipped off her shoes, and then knelt on the seat with one leg folded up under her, the other leg extending out until it lodged itself comfortably between the calf of my leg and the couch. She rose up a bit to pick up the wine glasses, offered me the full one which I took, then settled back on her folded leg with her own glass, her short skirt hiking up to reveal her shapely, tanned thighs. I offered a toast:

"To new friends," I said, raising my glass towards her.

"To new friends," she echoed back, then reached over and gently clinked glasses with me.

I took a small sip to taste it and then a larger gulp when I found the taste pleasing. The sparkling wine was still very cold and felt so good coursing down my throat, cooling me, settling in my stomach nicely. She took a small sip, then another small sip.

"Mmmmm, this is really good Kelly. Champagne was a great idea."

"Thanks Katherine, I thought the occasion called for it. I was hoping you'd like it," I replied, the effect of the first large gulp hitting me quickly, making me a little light headed.

I had eaten lightly that morning as I had for several days previously and had skipped lunch altogether. With a nearly empty stomach there was nothing to slow the progress of the alcohol from belly to my blood stream and then straight to my brain.

She was sitting very close to me, the knee of her folded leg pressed against my thigh, the foot of her extended stockinged leg resting against the back of my ankle. She was looking directly at me, taking in the full picture. I glanced back over at her, our eyes meeting briefly before I averted mine. I nervously took another healthy gulp of wine.

"I liked your e-mails Kelly. It told me so much about you. You write very well."

"Thanks Katherine," I said looking back up at her as she spoke. "It comes very naturally to me which is a good thing, because I have great difficulty talking, especially about those kinds of things. Guess I'm kind of shy in that way."

She took another small sip before continuing:

"Don't worry about being shy Kelly. I love shy types," she said pressing herself closer, her free hand moving to my bare arm and gently squeezing it before sliding down to my upper thigh and giving it a firmer squeeze; her hand remained there.

I put my hand over hers and gently rubbed it, enjoying the feel of her soft skin. I took another sip of wine, my glass now half empty. As the cool liquid slid down the back of my throat, I felt some of the tension in my body release. I took a couple of deep breaths and enjoyed the light-headed sensation from the wine. I looked back up at her, at her eyes checking me out from top to bottom, her mouth curled just slightly in a knowing grin.

"I especially liked the story you wrote - the story of a fantasy session with me. It was so realistic, so much detail, it was like it had already really happened. It was also very hot," she said, her voice dropping into a sexy, husky tone. "I couldn't put it down. My panties were so wet - I came twice the first time I read it; and twice more the second time."

"I'm so glad you liked Katherine," I said in a half whisper, the effect of her words tightening my throat, making it hard to speak. "It unfolds like a movie in my mind. I just write what I see."

"You have a great gift," she said earnestly. "I just hope the reality can measure up to the fantasy - I hope I can measure up," she said, her voice trailing off as she rose up from her half kneeling position and swung her extended leg up and over my lap, climbing on top of me, "cowgirl" style, her knees pressed against my hips, her thighs against mine.

"I don't think that will be a problem Katherine. You're doing great so far," I said smiling as I looked up into her face.

Amazingly, she had accomplished that quick maneuver without either of us spilling our drinks. Not wanting to push my luck, I took one more big gulp, draining half the remaining contents before setting the glass down on the table beside the couch. Katherine mirrored me, but took a much small sip before setting her glass down next to mine. Then she gently cupped my face in her hands, the heels of her palms meeting just below my chin, bent down and pressed her lovely soft lips to mine.

My senses were overwhelmed, the Champagne taking me past light-headed to a little high; the scent of her perfume, the warmth and softness of her body and the gentle caress of her hands and lips put me completely under her spell. Her lips pressed into mine, her mouth opened slightly and I felt her wet tongue pressing against my mouth. My lips parted for her and her soft tongue immediately slid in, curling and swirling as it went. I met her tongue with mine, entwining with it, swirling and sliding together in an incredibly erotic dance.

As we kissed, my hands rose first to her sides and then slid up along the tight top until my thumbs reached the underside of her full breasts. They were firm but not hard as my thumbs crept up until they reached her nipples which were now very hard and fully erect. She moaned as I brushed over them, her tongue reaching further into my throat. I was completely hard now, as stiff as I could possible get. Her hand found me as she released my face with one hand, sliding it down my chest and belly until it found the hard, expanding mound of my crotch. I groaned in response.

Slowly, our lips parted as she leaned back, arching her back, pressing her breasts against my hands as I continued to stroke her nipples and gently squeeze the large mounds. She straightened back up and looked deeply into my eyes as she reached for the top button of my shirt to undo it. Her hands were steady; mine were shaking as they dropped down to her stockinged thighs and gently caressed them, moving up slowly under her short skirt which had ridden up almost to her waist.

She continued down the line of buttons until she reached the bottom. Then, she slid the shirt off my shoulders and arms and down my back as I leaned forward into her to help. When the shirt came free, she tossed it down on the other side of the couch before bending and curling her upper body until mouth reached my chest. I gasped in surprise and pleasure as her soft lips encircled my nipples and began sucking and licking them. She used one hand to grip my chest, squeezing and kneading it as she tongued the nipple while her other hand still pressed into my hardness, making small circles with the heel of her palm.

My hands were also busy, kneading and caressing her inner thighs, moving up towards her crotch. I arrived at her "V" with both thumbs and immediately felt a large, very hard mound. My hands jerked back quickly as though they had touched a hot burner. It should not have been a surprise to me, yet it still was.

Katherine was a pre-op transsexual; a professional one at that. I knew she was a TS, in fact I had sought her out for that very reason. The special experience I was looking for was to be "topped" by a TS, a fully functional TS. In coarser language, I was looking to get fucked by the real thing after several years of strap-on play with dommes. As a sexual submissive, I had developed the increasingly urgent need to take it to the next level. Despite the skill of the domme I saw regularly, she could not simulate the pleasure and passion that only a real cock could provide. I needed to be completely sexually used by someone who derived real, physical pleasure from that use.

I had selected Katherine for this because she not only had great reviews, was fully functional and enjoyed topping, but for the fact that she was very attractive as a woman. Despite my sexual need to be fucked, I felt no sexual attraction to men and never had. The little gay porn I had seen left me completely cold, in fact beyond cold it was repellant to me. I couldn't imagine engaging in sex with some hairy, beard stubbled, muscular man. But a woman - a woman with "something extra," that seemed within the realm of possibility, even desirability. I had seen some TS porn and found some of it very arousing. A man fucking a TS did little to arouse me (although, unlike regular gay porn, it did not repel me), but a TS fucking a man, particularly a dominant TS, a very passable TS, attractive as a woman, I found very arousing.

So here I was, with Katherine, the TS I had sought and desired, so sexually aroused by her as a woman, that my conscious mind who knew she was a TS had simply taken a hike, disappeared to the point that I was actually surprised when I felt her hard-on through her panties. The comedian, Woody Allen, once wryly observed that God had given man a magnificent brain and an equally magnificent sexual organ, the penis, but just to keep things fun and interesting, only enough blood supply to operate one at a time. It appeared I was another victim of this cosmic joke - made evident by my fully engorged member and nearly vacant mind.

I had reached that first moment of truth - could I go through with this. Could I have sex with someone who was biologically and still genitally a man, even if she was to all outward appearances, a very attractive woman. For a few moments, my mind split into two distinct personalities - Kelly A was still thoroughly aroused by Katherine despite the "discovery" of the extra part - and was, in fact, desperate to continue; Kelly B, the still rational me, although taken aback by the sizable bulge, recalled the two promises I had made to myself - don't do anything unsafe, and at the moment of truth, follow your feelings. The answer as to what I should do was then self-evident. Kelly B quickly extinguished himself, to reappear again only briefly during the remainder of the session.

All of these thoughts flooded through my mind in the few brief moments after I had recoiled. I looked up at Katherine and saw her looking back deeply into my eyes, trying to determine just where I was at and whether to continue. I smiled at her somewhat sheepishly, embarrassed by my reaction and returned my hands to her inner thighs. Katherine smiled back at me, nodded slightly and then slowly and gently took one of my hands and placed it lightly on the hard bulge of her panties. My hand stayed and even started to slide up and down a bit as I felt for the outline of her instrument of pleasure through the thin black gauze of her nylon panties.

She arched her back and moaned, then pulled off her tightly fitted tank top, freeing her magnificent breasts. She threw her head back and shook, running her hands through her dark hair, thrusting her breasts into my face. My mouth opened automatically and took one of her spiky hard nipples into my mouth and swirled my tongue over it before sucking it. As I did so, my hand resting on her bulge felt her immediate reaction, the hard mound pulsed, jerked and swelled. I discovered that there is something to be said for immediate feedback as it further aroused me to tangibly feel her immediately react to my touch.

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bykelmag© 15 comments/ 254954 views/ 138 favorites

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