tagTranssexuals & CrossdressersTrying It On For Size Ch. 01

Trying It On For Size Ch. 01


I was twenty minutes early for my one o'clock appointment so I found a shady spot in the parking lot of the upscale chain motel, kept the engine running to power the air-conditioner on the warm Sunday afternoon, took a few deep breaths and tried to relax. My mind wondered back over the series of events that brought me here. The "here" I speak of was at the very cusp of a new sexual adventure; my first ever experience with a transsexual. For a middle aged straight guy with absolutely no gay experiences, experimental or otherwise, this was strange territory indeed for me.

I say that I am middle aged, but to be accurate, unless I am wildly optimistic about what my final age will be, I am fairly certain that I'm well past the mid-point of my allotted time here. I am well educated with two post-graduate degrees. And I'm generally considered attractive - standing six feet tall and a lean, compact one hundred and seventy five pounds. I still have a full head of light brown hair with just a few flecks of gray. In most things I am cautious and usually pretty rational and consistent in my behavior. I say "usually" pretty rational and consistent because every four to six months or so, I go through an intense period of heightened sexual tension that borders on obsession. I think of these periods as my own personal "Amok Time," a period in which my rationality is almost completely subordinated to an overwhelming need for a particular sort of sexual satisfaction.

It doesn't happen all at once. It builds up over time until it finally reaches a critical stage. At first, I begin to spend more and more time thinking and fantasizing about sex. During the work day, I spend increasing amounts of time lost in sexual thoughts and ideas. At night, I can't sleep without some chemical assistance - usually an Ambien and glass of wine does the trick. I begin to spend more and more time on the internet, looking at my favorite tried and true erotic sites and searching for new ones. I know that I've reached the critical stage when I find myself masturbating two or three times a day and still not sating the fires.

During most of my life, I am a confident, assertive, heterosexual male. In the bedroom, I almost always take the lead and drive the action. The sex itself is usually of the purely "vanilla" variety. In my fantasy life, I am a sexual submissive, completely subordinate to a dominant but highly sensual female. My preferences in that part of my life run to moderate bondage, including CB bondage, intimate body worship and strap-on training.

In the last five years, I have satisfied and exhausted those fantasy desires by visiting a local Domme during those critical times for a one to two hour session. The sessions with her have been wonderful. She is sensual to the max, highly skilled in the use of a strap-on and loves to have me orally service her. Moreover, she is very flexible and has no agenda of her own. Most sessions were scheduled by me with an e-mail describing generally what I wanted to do and what toys I would enjoy playing with. She had no problem with my bringing many of the toys and devices from my own extensive collection. She was very health conscious which is of utmost importance to me. I certainly did not want to acquire any sort of disease, of the sexually transmitted kind or otherwise. And she believes in the code of "safe, sane and consensual" in all BDSM activities. We always use a safeword - "yellow" for slow down or ease up and "red" for stop whatever is being done.

So, with this great Domme, what brought me down this road to a transsexual experience? I guess it began a couple of years ago when I came across an old photo set on the internet. The set featured one of the earliest transsexual porn stars, a gal that went by the name of "Carnal Candy." Her claim to fame was she was among the first of the "Dominant Shemales," not only topping her male partners but dominating them. Dressed in black, Domme regalia, she often used a leash or necktie to dominate and control her male sub. The power exchange was as important as the sex, in fact each built on and enhanced the effect of the other.

I was surprised at the powerful, erotic effect that old photo set had on me. Although sexually submissive (at least in fantasy and fantasy act outs), I had always thought of myself as one hundred percent hetero. In fact, the few times I had seen "gay" porn I had not been sexually aroused, in fact it actually repulsed me. Watching two hairy muscular guys go at it did nothing for me. After seeing Carnal Candy's photo set and acknowledging its effect on me, I began looking at some transsexual porn - photos, videos and stories. I was curious about why I was so aroused by the Candy set.

I found that I was not aroused by transsexual porn unless the t-girl was topping the male. The more dominant the t-girl, the more arousing it was for me. Throw in some bondage and a sensually aggressive t-girl and the effect on me was over the top - as strong or stronger than any other type of porn - including Femdom strap-on play. I began to understand just why strap-on play held such an appeal for me. It was actually an approximation of dominant t-girl action. As much as I enjoyed strap-on play, I always felt there was something missing. Perhaps that something was penetration by living, feeling flesh - feeling the effect I was having on it; actually having it grow, stiffen and swell and eventually cum in response to me. Regardless of how skilled the strap-on wielding Domme, silicon members just can't do that.

As I looked at transsexual porn, I found that I was attracted to and aroused by certain types of t-girls. First, she had to be feminine looking with a full bust and rounded hips. Heavily made-up, cross-dressed transvestites did nothing for me. She had to be female looking in all but genitalia. Second, the dick itself had to be - how shall I put this - large. The well-endowed t-girl had a far more powerful erotic effect on me than even the most otherwise luscious looking but poorly endowed shemale. Perhaps it had to do with my need for a power exchange in the fantasy and the large dick represented power and dominance to me. I don't know. But there it was - I had to recognize and acknowledge just what it was that was capable of turning me on so.

And there it sat for a couple of years. I recognized my attraction to certain types of transsexual porn and certain types of t-girls, aroused myself by viewing shemale porn from time to time but did nothing to advance to the next step - having an actual t-girl experience, other than occasionally look at some local t-girl escort sites.

This all changed last week when I happened to be browsing one of those escort sites and stumbled across an ad for a visiting t-girl named Tanya. The small photo of her in the sidebar window index attracted me immediately. She was very feminine looking. Clicking on it to bring up the full ad, my heart nearly skipped a beat when I saw the series of photos and the headline under her name which read:

"Best Top in Town, 10 inches long, 6 inches around."

The text of the ad goes on to describe her as a t-girl top who is six foot one inch, one hundred and forty pounds with a 36C-24-36 figure. From the photo I saw she had reddish, medium length straight hair, dark eyes and a pale white complexion. The ad went on to urge the reader to check out her reviews on "The Erotic Review" web site.

Now a lot of t-girl ads say there are eight inches or more and "very thick" or "6 inches around." Finding photos on their personal web sites, I found few that appeared to measure up to their claims. Whether they were starting the measurement from their prostates or they were confusing inches with centimeters, or perhaps just fibbing a little (in advertizing fibbing is called "puffery" but there was nothing "puffed" that I could see), I don't know. Almost all were decidedly modest in size.

So I took up Tanya's ad invitation to check out her reviews and did. What I found was consistently excellent reviews and consistent confirmation that her size was real - at least in the eight to nine inch range if not ten and certainly as thick as she claimed. I was intrigued, so I googled the name and found her on several escort sites in her native Los Angeles. One of the ads contained a photo of her member and it appeared to be as substantial as her ad and the reviews claimed.

Since at the time I was already deeply in the throes of one of my sexual "critical stages," this find just added to the preoccupation and sexual tension. It didn't take me long to decide what to do. I felt ready to try a t-girl experience if this Tanya was available. Nervously, I called her the next morning expecting to get a recording and a call back but was surprised and a bit shaken when she answered it. Her voice was very feminine, sexy and soothing and she quickly put me at ease. She sounded pleased that I was looking for a "top" experience, telling me that was her specialty. She also sounded pleased when I told her that I read her reviews and that, together with her ravishing appearance in the photos, prompted me to call her. We discussed the general topics of where and when and found her availability matched mine. We set a date and time - the coming Sunday at 1 o'clock at her motel, the location of which she said she would reveal along with directions when I called at noon on that day to confirm I was on my way. She agreed to my request to e-mail her a written description of what I wanted to do since I was sort of shy and had difficulty talking about it.

I had a particular scenario in mind - one that I had replayed many times in my mind after seeing the Carnal Candy photo sets and fantasizing being with someone like that. I described it in considerable detail in the e-mail I sent to Tanya and offered to bring all of the necessary toys and gear referred to in the description. I also asked to use "safe words" like those I had used in play with my Domme and asked that all contact be disease safe - i.e. all members covered for oral and anal contact and no exchange of fluids. She e-mailed me back the next day:

"Kelly, Loved your fantasy scene - got very aroused just reading it. I'm really looking forward to playing with you this Sunday. I promise to show you a great time. Topping is what I do. You will get all that you want . . . and then some. Bring whatever toys you want. Safe words - yes. Protection and safety - definitely, yes. Call me at noon when you are on your way over. Tanya"

I went to bed early Saturday evening, knowing I would need the rest and that I would have to get up early. Even with the Ambien, I had trouble sleeping; my mind an almost frenzied kaleidoscope of sexual and BDSM thoughts that were half-awake fantasy images and dreams merged to form its own odd reality. My sleep was made even more difficult by my prior decision to refrain from masturbation for four days. From past experience with my Domme, I knew doing this would create a state of nerve twitching sexual tension within me that not only would heighten the pleasure of the experience but also would make me very obedient and compliant.

Sunday morning finally arrived, the alarm going off at 5:30 A.M. I awoke immediately, alert, nervous but incredibly excited. I gulped down an energy drink - a combination of caffeine, sugar, ginseng and various other herbs. The effect was almost immediate on an empty stomach, especially since I had refrained from eating solid food the previous day. I felt a warm glow, a kind of buzz envelope my entire body, revving up every system.

It took me four hours to complete my cleansing procedure; one I had developed through trial and error before my many previous Domme visits. I found that a series of small, salt water enemas worked best for me. I began with half a dozen 3 - 4 cup infusions in various positions to reach every corner of my lower tract. Then waited an hour and a half, walking around, taking care of various chores, assembling and packing the toys and gear I wanted to bring, preparing the gift envelope and laying out my clothes.

After an hour and a half of this activity, I felt the "second wave" of bowel contents drain and build. This is the enema fluid and lower colon contents that get trapped in the initial enema series and simply take time and movement to fully drain. Once that is emptied out, I then use a series of small infusions, 1-2 cups of warm salt water to fully rinse the rectum and lower bowel until it is completely clean.

With my insides all clean, I then go to work on my outside, taking a shower, and then a long, hot, soapy bath, using a wash cloth to scrub and clean every surface. Once that is done, I carefully trim and shave my pubic region which I shave on a regular basis anyway. On special occasions like this, I also carefully shave my anal area and perineum, the small patch of sensitive skin between the scrotum and anus. It takes a flashlight, a mirror and some interesting contortions but I've gotten pretty good at shaving myself clean there.

Finally, I carefully shave my face, neck and upper back, then clip and file finger and toe nails. I was done by 11:00 A.M. which was just as I had planned. I always like to have an hour or so of extra time in case there is some last minute drainage that needs to be taken care of. I used the hour to walk around a little, check e-mail, re-read the scenario I wrote and sent to Tanya and down another energy drink.

Feeling certain there will be no further drainage, I got dressed, slipping on a pair of new, white briefs, khaki trousers and socks, black loafers and a loose fitting, black linen shirt worn outside the pants. I checked the contents of my "toy" bag once more, getting little flashes of memory of when the items had been used previously. I felt myself stiffen as I remembered the Domme using each of the items on me.

At exactly noon, I called her, hoping that she was there, ready and available. I tried to mentally prepare myself for the disappointment if this elaborate preparation turned into a gigantic waste of time because she had forgotten about me. She answered the call on the second ring and knew it was me. Tanya gave me the name and address of the motel and told me to call again to get the room number when I arrived. Off I went, on an adventure unlike any I'd had before. As I closed the door behind me, I had the feeling that I was closing the door on my life up to that point and entering a new part of my life - something that would be entirely new.

Sitting in the shady spot in the motel parking lot, I glanced down at my watch and saw that I had been lost in recollection for almost fifteen minutes. I took a few more deep breaths and assured myself that I was ready for this. Then I called her to let her know I was at the motel. She answered on the fourth ring, letting me sweat through the first three.

"I'm in room 217 at the end of the hall. You will find the door ajar - let yourself in. Put your toy bag on the table on your right when you enter, place any gift you might have for me on the night stand and then go stand by the side of the bed facing it."

The tone of voice was different. It was still feminine and sexy but the easy friendliness and familiarity was gone, replaced by directness and command. She was issuing instructions to me; instructions, from her tone, I was expected to obey to the letter. Tanya had slipped into the dominant, top role I had asked for and it sent a shiver of excitement through me.

The motel was a sprawling two story building. It took me a few minutes to find the correct wing. Then I climbed the stairs quickly and headed down the narrow, outside corridor, a little surprised to be as out of breath as I was from just one flight of stairs. Following the room numbers, I found #217 at the end of the hall. The door was open slightly, held open by a folded magazine. With one hand on the door knob, I bent down and retrieved the magazine and then went in.

Coming from the bright, afternoon sunlight, the inside was dark, very dark. As the spring-loaded door closed automatically behind me, I was thrust into almost total darkness. I could see only the dim light of a low wattage, "energy-saver" bulb from the desk lamp across the room. The light didn't seem to penetrate the rest of the room. The blackout shade and drapes covering the window allowed no light from the outside to enter. I could not see anything that was immediately around me. Then Tanya's voice from the right:

"Your eyes will adjust in a few moments. The table is to your right. The bed and night stand are ahead of you."

I stood frozen in the doorway, taking in the light scent of perfume that seemed to surround me. It seemed like a long time but probably was only a minute or so, but glancing over in the direction of the voice, I finally started to make out the outlines of furnishings - two chairs and a table. Then movement, Tanya rising from one of the chairs. I still could not make out any details, the form, more of a silhouette, rose slowly. My eyes adjusted a little more until the table became clearer and I could see well enough to be sure there was nothing between it and me that I would trip over. I took a couple of steps over and dropped my bag on the table, tossing the magazine I had picked up from the door frame alongside it.

I heard the rustle and swish of clothes and saw movement again from the dark form coming into further detail as my eyes adjusted. It was Tanya and she was facing me, looking at me, looking down at me - in her heels she seemed incredibly tall. As my eyes adjusted further, I could make out the reddish color of her hair and the blood red color of her lipstick. She smiled and her very white teeth seemed to glow in the dark. She was wearing a slinky black mini-skirt and stockings that showed off her long legs and a halter top that accentuated her substantial cleavage.

I continued to follow the instructions she had given me, stepping over towards the bed to drop off the gift envelope on the night stand and then finding the edge of the bed and taking a position standing about mid way along the side facing nearest me. Looking down, I saw the bed only covered by a sheet and two pillows stacked near the center of what looked like a queen-sized mattress. I heard Tanya approach from behind me and then stop by the night stand. The slight rattling sound told me she was checking the envelope contents; then I felt her right behind me.

Her hand came to rest lightly on my shoulder; I was struck by the contrast between the gentleness of the touch and the large size of the hand. I felt her lean closer, her warm breath on my ear as she whispered:

"Welcome Kelly. You are in for an incredible experience provided you do exactly what I tell you to do. Put yourself completely in my hands. Just relax and leave it all to me. You have no decisions to make. While you are in this room, you will call me Mistress or Mistress Tanya. Do you understand everything I've said?

"Ye . . yes Mistress Tanya," I said, a little amazed at how quickly and completely she had slipped into her role and the powerful effect it had on me.

I felt her hands drop down and reach around my chest. inding my shirt buttons she started to undo them. She pressed herself closer to me as she did so, the evidence of her own excitement pressed hard against my butt. It sent a shudder of excitement through me as I felt her hardness pressed into me. She thrust her hips forward a little, a symbolic preview of what was to come.

Tanya finished unbuttoning my shirt and then her hands roam around inside, stroking my torso, running her long, red finger nails across my chest and down my torso, then kneading and massaging my flesh with her strong hands. I felt her lips on my ear and then her tongue as she tasted the edges of my ear lobe before flicking the tip of her tongue in the opening.

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bykelmag© 5 comments/ 180372 views/ 135 favorites

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