A Delightful Encounter

by Thomas Antonson

Caution: This Erotica Sex Story contains strong sexual content, including Consensual, Shemale, TransGender, Fiction, Anal Sex, Analingus, Cream Pie, Fisting, Oral Sex, .

Desc: Erotica Sex Story: Two lonely people make a connection in a hotel bar. Much sex ensues. They both learn something.

I’m a reasonably good looking middle aged man who travels a lot. I’m also widely read, a good conversationalist, a good listener, a storyteller, and, shall we say, sexually flexible.

That last bit cost me my marriage. My (now ex) wife didn’t approve of bisexuality. It was a blow, but I got over it. My children, thank goodness, took a more tolerant view. At any rate, I vowed never to enter into any further long term relationships beyond FWB or casual.

I’m careful about the people with whom I share a bed. I don’t “cruise” and I practice (mostly) safe sex. I have myself tested regularly, although I realize that a test is only good for that moment. It reassures my partners at any rate.

I’m not promiscuous but middle aged men still have needs. While Rosy Palm is always available for quick relief she’s not a long term solution. I’ve never paid for sex, unless you consider the cost of the divorce. I don’t rent sex partners. Thanks to the internet if I’m really on a losing streak I can always find a casual hookup. Those don’t always go well but at least I get off.

Life on the road can be lonely. That is, apparently, the raison d’etre for hotel bars. And that’s where I found myself one evening while on a business trip. The hotel was nice and so was the bar. The bartender was cute, competent, and friendly. I didn’t tax her skills by asking for exotic drinks. She made a great G&T and that was enough for me.

There were quite a few of us road warriors there that evening watching college basketball on multiple screens. The seat next to me was the only seat at the bar without a butt on it.

A woman put her hand on the back of that empty seat, and as I turned to look she asked “Is this seat taken?”

“No, it’s not,” I replied. “Be my guest.”

“Thank you.”

I watched as she sat down. She was young and good looking. She was dressed for business, by which I mean to say she wore a blue suit with a chalk stripe paired with a soft cream oxford cloth open collared buttondown shirt. Her hemline was just above the knee and her stockings were what pantyhose packages would call “nude.” Her shoes were good quality but not flashy. She wore enough makeup but not too much. Her fragrance was tasteful, light, and vaguely floral. Her hair was fashionably cut and strawberry blonde, leaning more toward strawberry. She had a trim, athletic, figure. All of this I took in during the two or three seconds that passed between the time she asked if the seat next to me was taken and when she sat down.

“What’s good here?” She asked.

“I’m having G&T and the locally distilled gin isn’t bad.”

“I’ll give it a go,” she said, raising a well manicured hand to signal the barmaid.

“What’ll it be?” The barmaid asked.

“I’ll have what he’s having. Extra lime please.”

“Good choice. I’ll have it right up.”


It was her turn to look at me. I felt like I was being appraised for auction. It was almost uncomfortable. I wasn’t used to being looked at this aggressively by a woman. It made me wonder how many times I’d done that to a woman and how she must have felt.

“I’m Kathleen,” she said, sticking out her hand.

“Jim,” I replied, taking the proffered hand and giving it a squeeze.

“Nice to meet you. Business or pleasure?”

“So far, only the former,” I said. “But I’m always open to pleasure.”

Kathleen chuckled. “I like that. I feel the same way myself. Business trips can be so boring if there’s no chance for any fun, don’t you think?”


“This is my first time in this hotel. Is the restaurant here any good?”

“So-so, but at least it’s expensive so we can lie about how good it was later,” I said. “And it has the added virtue of being close.”

“Ah, irony. I recognize it when I hear it. Have you eaten yet?”

“No, I haven’t. The thought had crossed my mind though.”

“Good. I’m more hungry than thirsty. Care to join me in the hotel restaurant for a bite?”

I laughed. “You certainly work fast. I’d be a fool not to accept your invitation, if only to find out where a straightforward person like you has been all my life,” I said.

Kathleen laughed too. It was a low, melodious, chuckle. I liked it. I wanted to listen to her talk.

I got off my barstool and held out my arm. Kathleen smiled, slid off her stool and took it.

Fast forward through a halfway decent meal flavored with delightful conversation. Kathleen was funny, colorful, and earthy without being crude. She laughed at my stupid puns. I laughed at her wisecracks. The checks (yes, plural -- we each paid for our own meal) came and we paid. Paperwork was signed and stowed away for eventual submission to the bean counters. A moment of awkward silence came. I sensed that neither of us wanted the evening to end just yet. I suggested after dinner drinks in the hotel bar.

Kathleen had other ideas.

“Most after dinner drinks make me sick. How about we adjourn to my room and find out what two people at loose ends can do for each other?”

I hesitated for just a moment and Kathleen’s face fell.

“Too forward?”

“Not at all. Refreshing, in fact. That’s the second time you’ve completely surprised me this evening. I’m not used to that. By all means, let’s explore. Lay on MacDuff.”

Kathleen smiled. She stood and held out her hand. I stood and took it. Suddenly Kathleen’s expression became serious.

“Something wrong?”

“There’s information you don’t have. I need to tell you something about myself before we go any further.”

“You’re a transwoman,” I said. Her look of surprise and shock was all the confirmation I needed.


“Bi-sexual intuition,” I said, smiling.

“Now I’m the one surprised,” Kathleen said. “That’s not usually how this goes. We were having such a great time that I almost forgot that we hadn’t known each other for more than an hour or two. And then I realized I hadn’t told you and worried you’d be like so many others who reject my kind.”

“We are who we are. I may have my own prejudices -- we all do -- but that’s not one of them. You and I have chemistry. We both feel it. I think it’s worth exploring. Human interactions are full of surprises. Let’s go find some, okay?”

“Well, that wasn’t as awkward as it should have been,” she said. “You’re an interesting man Jim. I think this will be fun.” Her smile was back. I laughed. She laughed.

She took my hand and drew us toward the bank of elevators across from the restaurant.

We were alone in the elevator. I took her in my arms and kissed her, pulling our bodies together. She couldn’t possibly miss the bulge in the front of my slacks. She moaned into my mouth. I responded by tightening our embrace.

“Eleventh floor,” announced a recorded female voice.

We disengaged and hurried down the hall. She pulled her room key from a pocket in her suit jacket. We raced each other to her door, both anxious to get inside. As the door clicked shut behind us we recommenced kissing with a side order of groping.

I’m just a shade over six feet and Kathleen is about five foot nine plus heels. We fit together like a glove. I put my hands on her ass and pulled her against me as our tongues dueled. She upped the ante putting her hands down my pants from behind and cupping my ass skin to skin. I slid my hands up and slipped her jacket off her shoulders. She had to let go of my ass to shrug it off. My jacket joined hers on the floor. We picked up where we left off only this time my hands answered her groping with a little of my own as I sought her naked ass beneath its layers of expensive wool and lingerie. I was pleased to note she wasn’t wearing panty hose. I enjoyed molding the firm flesh of her bottom with my fingers.

We had both started to breathe heavily ... Things were getting a little out of hand. I was afraid we’d start ripping each others clothes off in about ten more seconds. I broke the kiss.

“Nooooo! Keep kissing me. I love how you kiss,” Kathleen complained.

“I love kissing you. And I want to go on doing it. But I would like us to take our time instead of acting like a couple of teenagers on their third date. I like to unwrap packages slowly and savor the reveal. And, this is one of my favorite shirts. I’d hate to have it ripped.”

Kathleen took in a breath as if to prepare a protest. Then she threw back her head and laughed.

“You’re different. Most guys would already be fucking me by now.”

“I’ve been around a while. I’ve learned to appreciate each moment. When you’re young time means nothing. When you reach my age you start thinking about how much you have left. I like to make the most of every second. I don’t like to rush. Especially when it comes to sex.”

.... There is more of this story ...

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