Transgender Encounter

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First time with a t-girl.
1.4k words
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ludocio
ludocio
15 Followers

I was at the Mall in Torrance, CA looking for a new pair of pants. There was this lovely young woman named Sherry working there, who was very solicitous, helping me find my size and select a pair of pants that weren't too out of style. I hate to shop, you see, so I usually wear a pair of jeans or shorts. These sort of clothes don't require trying on and are really never out of style. But this time, I wanted to take my time and get a nice pair of pants that fit well.

She was a redhead, about five and a half feet tall, with a very attractive, thin build. I prefer women with small boobs as opposed to large tits that will eventually succumb to gravity and make knee-knockers. Such is that fate of my wife: droopy boobs and a very flat ass. Yet, I love her and can never leave her and the kids.

Sherry, the gorgeous redhead I've described, brought me several pairs of pants to try on and led me to the dressing room in the back of the shop.

"How do they fit?" Sherry asked. I hadn't realized she was standing right outside of the door. I was a bit startled, but replied, "These beige ones seem a little loose, but the length is good. I suppose I could just use a belt."

The door to the booth opened and Sherry came in, closing the door behind her. "Let's see." she said and looked at the pants I had just put on. "No, look you can pull them right off." She reached over and pulled the pants down to my knees.

"What the...?" I gasped, taken by surprise and not really knowing what to do. I didn't even have time to be embarrassed. My underwear had been pulled down as well and just barely coved my goodies. I stood there like a dope who had been pantsed in the hallway at school.

"Oh don't be silly!" was her response to my inarticulate remark. "Here, try these on." she told me, handing me another pair that, frankly looked just like the first.

I was really nonplussed but was trying not to appear like an uptight middle-aged man. I'm under no delusion that I'm younger than middle age, but I do keep in good shape and I still get a second look occasionally. Besides, she was absolutely beautiful and I was undoubtedly attracted to her. I wasn't sure if she was attracted to me or just messing with me out of boredom.

I took off the pants I was wearing around me knees and pulled up my underwear before trying to put on the ones she had in her hand. "Oh..., you are dense." She scolded. "Take those things off. You're about to get lucky."

She stepped closer and pressed herself against me. I looked in those spellbinding green eyes and let my jaw drop in amazement. Fortunately, this must have looked as if I was opening my mouth for a wet kiss. She kissed me hotly and breathed into my mouth "We have to be quick". Sherry reached into my shorts and grabbed hold of my member. I hadn't even realized I was hard. She squeezed me tightly and began to pump her hand up and down.

I hadn't been with a woman other than my wife since I since two years before we got married. Truth be told, I hadn't even been with my wife for years. These thoughts were barely on the fringe of my consciousness as Sherry brought my arousal to a peak. I was completely enthralled with this woman. Not only was she gorgeous, she was my idea of physical feminine perfection. Also, she was squeezing the head with which men decide matters of sex. I was helplessly in lust and completely in her thrall.

"Shhh," she whispered and crouched down to take me into her mouth. God, her hot mouth felt so good, I was sure I'd lose the load right there. She stroked and sucked vigorously and my pelvis rocked of its own accord. She stood up, still stroking me and whispered in my ear breathily, "Do you want is baby? Do you want to come inside me?" I may have managed "Ghaaaa." Good God almighty, did I want her? I'd do just about anything at this point to get inside that perfect body of hers.

She pressed hard against me and asked me to suck her nipples. They were in my mouth as if by magic; hard and delicious and slick from my tongue – pink, like bubblegum. She turned around and pulled her skirt up. I pulled her lacy panties down. I had to brush my lips against her silky smooth bottom. I could feel the invisible hairs on her milky white flesh. I knew her pussy would be just as pink as her nipples. I spread her cheeks a little to get a look at the, until this moment, forbidden treasure. Pink and puckery with the lightest circle of blond hair, it was the prettiest bum I had ever seen in my life.

She turned around and grabbed hold of my dick again. She licked my lips and stroked me fast and hard whispering in my ear, "I don't have any lube baby. We'll need to do oral. Maybe tonight we can go all the way. "She kneeled down immediately and started to suck me off. My God did this woman know what how to suck dick!

I thought about her wet, pink pussy and how tight it must be – and how delicious. Why would she need lube? I prefer to be the last one cumming, so I stopped her from finishing me and pulled her mouth up to mine. Also, maybe when she realizes that my mouth will make her pussy wet enough to not require lube, I can get what every man that's ever seen her has wanted. Her tight, thin little body is the very think I had fantasized of all of my life.

Without saying another word, I pushed her gently against the wall and knelt down for a little treat. She was pink and soft and smooth down there, with light red pubic hair neatly trimmed. But it wasn't a pussy. It was a little pink, smooth cock! Again, I said the same inarticulate thing. "What the...?" and my jaw dropped in amazement, just as before. And, just has she had inserted her tongue into my mouth, she this time inserted her tiny dick.

"Oh, God, yes, baby!" she moaned quietly as she placed her hands gently on each side of my head and began to rock her pelvis.

Her excitement and the fact that I was as turned on as any time in my life – plus maybe the fact that no one would ever know – allowed me to make a rapid decision. I sucked her as she had sucked me. For the first time in my life, I had a penis in my mouth.

She began to thrust her sweet little cock into my greedy mouth. Her excitement became my own. I now wanted nothing more than to give her exquisite pleasure. I had always been a very considerate lover and now, with the shock of the situation over, I made every attempt to give her a glorious orgasm.

Sherry was trembling all over. She fucked her delicious cock into my mouth and I sucked as hard and fast as I could. When I needed a breath, I stroked her as fast as I could, watching her little pink pecker disappear into my fist and then poke out again with the swollen, red head glistening. Her whole body began to spasm and as her cockhead swelled I felt the first release of her cum. She then shot a huge load into my mouth. Stream after sweet sticky stream she ejaculated into my mouth. It was delicious.

After I was certain she had completed her orgasm, I stood up and looked into her eyes. She looked drunk with consummated lust. She kissed me passionately but gently, her tongue tasting her own flavors. She sucked my lips and smiled as she sighed. "That was wonderful! Now, it's time for you."

I was now a little worried about being caught. Besides, I somehow felt satisfied by giving her such satisfaction. "Let's finish later at your place." I suggested. She wrote her number on the back of her business card and left after we shared one last kiss.

Now tonight, I have made arrangements to be away from home for the evening. Sherry lives in the next town over. I can't seem to lose the erection I get every time I think of her.

ludocio
ludocio
15 Followers
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6 Comments
AnonymousAnonymousover 3 years ago
Respectfully Well Written!

Thank you for being one of the only authors on here who doesn't misgender or disrespect trans women. We really appreciate it and it makes the writing much more enjoyable.

AnonymousAnonymousalmost 5 years ago

Very good. I would suck that cock. Wish it had her fucking him though. Respond if you would let her fuck you

AnonymousAnonymousover 5 years ago

Very good story

Transgender can mean both with or without SRS.

AnonymousAnonymousalmost 8 years ago
This...

This is not transgender this is shemale. Transgender is where she is completely a woman after being born male e.g gender reassignment surgery.

AnonymousAnonymousover 15 years ago
horny

That was so horny and got me hard. Hope you tell us what happened when you met up later

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