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A True Tale From My Travels

"The Christmas shopping season brings new experiences."

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The only light in the small motel room comes through the sheer curtain behind the partially open drapes. I watch as she approaches and places her cherry red lips against mine. A heartbeat later, my arms wrap around her and she reciprocates and we hold each other tightly.

My hands slowly slide down the back of her silky blouse as our tongues explore each other's mouths and eventually wind up on her butt cheeks. I marvel at how firm they are as I gently rub and squeeze them under her short skirt. She ends the kiss and I feel her pull away so I release her.

I am treated to a show of her slowly removing her blouse to reveal a shiny blue bra hidden underneath. I watch with unblinking eyes as she slowly rubs both hands over the silky cups of her bra and I note that her eyes are lit with desire. I move in to hug her again but she stops me by placing one and on my chest as the other hand moves behind her back. A  second later I hear the soft sound of a zipper being drawn down and with a wiggle of her hips the short pleated skirt slides down her shapely legs and puddles at her ankles

She is wearing a half-slip the color of her bra that is trimmed with delicate lace and I am unable to tear my eyes away, ladies wearing slips have always been a weakness of mine. My eyes are locked on hers as she carefully steps out of her skirt making sure that she doesn't snag the heel of her knee-high boot in the discarded garment. As she does this the hem of her slip raises and I get a glimpse of the ribbon holding up her nylons. I thought she was wearing pantyhose and my cock almost bursts through my jeans when I learn the truth.

###

I was seventeen and just starting my second holiday season on the road performing magic and puppetry at the enclosed shopping malls that were springing up everywhere across the country. There was no cable TV back then and the internet as we know it did not exist, so the local mall featuring a live puppet or magic show always brought the people out.

I had quit school the year before as I wasn't really learning anything and my social life was non-existent. A month later, I responded to an ad in the newspaper of a company that was seeking a performer. It was after a month of training, a whole new career began for me and I begin to reap the benefits of a childhood fascination with magic and puppetry.

That first year on the road was an education that I would have never gotten in school. The first thing I learned was that I wasn't such a fat and ugly loser with no personality as the girls in school had titled me. I was able to hold my own in the adult world where you were judged on your looks and personality.

The second thing was the sexual education aspect. Having gone through junior high and a small portion of senior high without a date, I believed that I was probably going to die alone and a virgin, and the hotties in school echoed my belief. How wrong they and I were.

I was now getting laid on a regular basis. Single, divorced, and sometimes married females from sixteen to fifty warmed my bed on those long nights away from home. They weren't skanks either, they were very attractive and in shape. I reasoned that I wasn't such a fat and ugly loser if I was able to attract their attention.

These sexy ladies taught me that there were more sexual positions other than the standard missionary and I learned my lessons well. I was also taught all about foreplay and I became quite good at it. Eventually, I became less shy and was able to actually have a conversation and flirt when one of these attractive ladies approached me and that's how today started.

It was the day after Thanksgiving and the Christmas shopping season is now in full swing and the mall was jammed with shoppers. This year was going to be different for me than the last one. That first year I did three or four shows that season staying a week at any given mall.

The merchants' association of this mall wanted me there from Black Friday until Christmas Eve and they were willing to compensate the company which took care of me for missing the holiday dinner with my family, as Thanksgiving Day would be the best day to do my set-up.

It was during the first show on the first day that I saw her through the peephole that was hidden in the scenic backdrop. The peephole was used to watch the kids' reactions to the show. It was also used to call on them when it came time for the live portion of the show. 

She was truly a sight to behold sitting there in her short pleated skirt and knee-high boots. Her black leather jacket was open just enough to allow a glimpse of the black and white striped blouse that was tight across her full chest under it.

I waited until most of the audience had gone before I emerged from my puppeteer's hole and lit a cigarette. I was depressed that the pretty female had also departed but my smile returned when she approached carrying two large cups of Coke and offered one to me. I gave my thanks and asked her to be seated in the area behind my stage that I had staked out as my own.

"That's a great show. How did you get permission to use the likeness and voices of the TV cartoon characters?" She asked.

"It wasn't easy and kept the lawyers busy for months," I responded as I continued to take in her beauty.

She introduced herself as Tonya and as we chatted, I learned that she was on a forced Christmas vacation due to her company shutting down until the new year.

"Well, that sucks," I responded.

"Not really. We got a small Christmas bonus plus two weeks severance pay. So between that and my unused vacation time, I'm in pretty good shape," she answered.

As we continued to chat, I stole glances at her nylon-covered legs and full chest whenever I could.

"I can see that puppetry is not the only thing you're interested in," she commented when she caught me staring at her legs.

I felt my cheeks redden and I stammered an apology. She only smiled as she crossed her legs giving me a better look at her silk-covered knees and thighs. She also unzipped her jacket a little more so I could see more of her full chest.

"So how do you occupy your time off? Hit all the local watering holes and lure the local girls back to your motel room?" She asked with a wicked smile.

"Not really. My age prevents me from visiting them," respond truthfully.

"How old are you?" She questioned.

"I'm only seventeen," I responded and I watched as her nipples become prominent under her blouse at my admittance.

"Really. You don't look or sound like a teenager," she responded.

"Well, I am. So my nights are spent in my room watching reruns," I informed her.

We shared stories about our lives for almost two hours and I was forced to end the conversation as it was time for another performance. This time when the show ended, Tonya is nowhere to be seen but I had no time to brood as I was approached by the president of the merchant's association.

He complimented me on the show and informed me of a school group that would be attending the show tomorrow and asked that I say a few words to them. He then added that they had arranged for me to appear on a local TV show to promote the mall and my show and handed me directions to the TV station and the time to be there.

Before I knew it, nine o'clock had arrived and that signaled the end of the shows for that day. I locked up the stage and headed to the Motel Six where I took a shower and got into my lounging clothes and set my alarm so I didn't miss the TV taping. It was around ten-thirty that I heard a knock on the door and discovered Tonya on the other side in the cold November weather. I opened the door and stepped back to allow her to enter.

As soon as she crossed the threshold, she dropped her purse on the table and draped her coat across the back of the chair, and then turned to stare at me.

"So, what brings you here?" I asked.

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"I thought that maybe you'd prefer to spend the evening with a pretty girl over watching reruns," she replied as we embraced.

"You thought right," I answered and we commenced to kiss and hold each other and now we are back to the beginning of this tale.

###

"My Lord, you're as stiff as steel," she comments as her hand strays to my crotch. " And I really didn't do anything yet.

"Pretty girls in sexy lingerie have always been a weakness and a total turn-on," I reply.

In response to my admission, she helps me remove my t-shirt and a second later, the silky cups of her bra are pressed against my naked chest and the sensations are beyond description. With our mouths still glued we make our way over to the bed where she offers to remove her bra. I ask her to keep it on as I am enjoying the touch of the cool silky garment under my fingers and against my chest.

She smiles and then helps me remove my sweat pants before we slide under the top sheet. Tonya has not removed her slip and my rock my hard cock is becoming even harder as it makes contact with it. When I try to slide my hand under her slip so I can run my hands along her nylon clad leg Tonya stops me.

She gently pushes me on my back and then takes hold of my rigid manhood and begins a slowly pump it. She kisses my ears, neck, and chest in between the long lingering kisses as she does this.

Between her hand on my cock, her silky bra pressed against my arm, and the feeling of her slip and nylon covered leg against my naked thigh I am in heaven. It is those actions along with her slowly running her booted leg up and down against mine that has me ready to shoot my load in no time.

When I tell her that I am going to cum she places the head of my cock against her hard flat stomach and tells me to shoot my load against her warm silky skin. She then increases the speed of her hand on my rod and a heartbeat later I grit my teeth and let loose on her belly and Tonya moans as the warm sticky fluid hits her skin.

I lie there enjoying the after-effects of my orgasm while Tonya cleans herself off with the kleenex from the box on the nightstand and then announces that she is thirsty, I tell her that the fridge is stocked with Cokes and I watch her slide out of bed and enjoy the movement of her backside under her slip.

She returns with two frosty cans and we enjoy our drinks in between sharing gentle kisses. Now Tonya has neglected to slide under the thin sheet and as we drink, I take in the sight of her lingerie-clad body laying next to me. That's when I notice a slight bulge under her slip that I somehow failed to notice before.

"What the fuck?" I ask as my hand quickly moves to her crotch before she can stop it.

There under the silk of her slip and panties, I can feel a small hard cock and I leap from the bed as though I am shot.

"What the fuck are you?" I demand in an outraged voice as I put my sweatpants back on.

For the first time since she arrived, she loses her smile and a look of sadness crossed her pretty face.

"I'm a transgendered person," she responds in a soft voice.

I have never heard that term before and up until that time, the only male I'd ever seen dressed and made up as a female was the late comedian Flip Wilson when he was doing Geraldine, so I ask her to explain. She crawls off the bed and joins me at the table and I still see no trace of a man in her face as she takes a seat opposite me. Over the course of the next hour, she goes into detail about her life, and I find myself feeling very sad for her.

"I'm a girl trapped in a man's body and am in the process of becoming the woman that I believed I was meant to be. I had hoped to come over and share some kisses and jack you off before I left. All I had to do was keep your hand from sliding under my slip," she admits.

"So why me?" I ask.

"Because I was attracted to you and I felt a connection. Can you get intimate with someone if you don't feel a connection with?" she asks.

"No," I respond truthfully.

"Neither can I," she answers. "That's why I spent so much time talking to you at the mall, I wanted to make sure what I felt was real. Tell me that you didn't feel an attraction too?"

"I was attracted to the girl I had just met," I say, choosing my words carefully.

"Then think of me as a girl with something extra," she responds as she stands up and heads to the bathroom leaving me alone with my thoughts.

'How could I not feel her cock pressing against me when I embraced her? Was I so lost in the sensations of her hand on my cock, her sweet long kisses, and the feeling of her silky lingerie against my body that it made me blind?'

When she reappears, I am stunned by her appearance. She has removed her slip and nylons and is standing there in her bra, panties, and boots. Her body is in perfect shape and tanned and I don't think that some of the real girls I slept with looked this good.

She approaches the table and stops less than a foot away from me where she removes her bra and I am treated to the sight of the most perfect breasts I have seen up to that point. She then reaches out and grabs my hands and gently pulls me into a standing position before she places them on her firm breasts. They are warm, full, and silky and I unconsciously run my thumb over the extended nipple the way I have been taught. She utters a soft moan as I do this.

"Yes, they are real," she responds to my mental question.

There is a struggle going on inside my head. My sensible side wants me to throw her out while my lustful side wants her to stay as this is a new experience. The absence of her slip allows me to see the outline of her cock under her silky panties and it seems to be growing with each passing second.

"Can I kiss you again?" I ask in my timid voice.

"As long and as often as you want," she responds.

The feeling of her full silky breasts with their hard nipples against my naked chest has me hard in no time and I feel no revulsion at the feeling of her hard cock pressing against mine. We eventually make our way to the side of the bed, where I notice that the outline of her cock is more obvious under her tiny silky underwear. I ask her to remove them.

"Are you sure?" she asks with hesitancy in her voice.

'Yes, I'm sure," I tell her as I stare into her eyes.

I watch as she shimmies her panties down and removes them before she places her hands behind her back to give me a better look at her. Like the rest of her body, her crotch is smooth and hairless and her small cock is as stiff as mine. Tonya then grabs the waistband of my sweats and draws them down my legs. After I step out of them, we embrace again and now I have the sensation of my hard cock rubbing against hers along with the feeling of her breasts against my chest.

We manage to separate long enough to crawl back onto the bed. Tonya has me lie on my back once again and this time she straddles me and her hard cock makes contact with my belly and mine is pressed against hers. She begins to slide herself up and down and the sensation is beyond description.

Tonya moans and whimpers as she continues her movement in between our kisses. Finally the familiar feeling of getting ready to shoot floods my brain.

"Tonya, I'm going to cum," I manage to tell her.

"Me too," she responds.

As she increases the speed of her grinding her body against mine my cock feels red hot as does hers and a heartbeat later, I let loose against her warm flesh. A second later she issues another long sexy moan and can feel her load shoot against my skin. We collapse on our backs, gasping for air.

Eventually, I pull her into me and I hold her and plant gentle kisses on her cheek and lips. At some point, I drop off to deep sleep because when I awake she has gone and I never heard her leave.

I head to the bathroom to shower and remove the dried semen from my skin.  When I snap on the light I see the words " See You Soon" written in red lipstick on the large mirror and below that is an imprint of lips.

 

End of Part 1.

 

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Written by ThePhantom
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