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.”
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.
“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.
“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.”
As I spoke I unbuttoned her shirt. She took the cue and untied my tie. I pulled the tails of her shirt from her skirt. She shrugged it off her shoulders and let it fall to the floor. Kathleen undid the buttons of my shirt. I unbuttoned the cuffs, thankful that I hadn’t worn cufflinks, and let her slide my shirt off to join hers in a rapidly growing pile of clothing at our feet. I pushed her, gently, toward the bed. The curtains were open letting in just enough light from nearby buildings and street lights so that we could see each other. We kissed as we moved. When the backs of her legs reached the bed she let herself go. I supported her, lowering her gently to her back. I kissed her jawline, her chin, down her neck and across her collar bones. She trembled slightly as my feathery kisses raised goosebumps.
I unfastened her bra with my fingers and pulled the straps off of her shoulders with my lips and teeth. I kissed my way back up to her mouth and as our lips locked I gently and slowly worked my hands under her bra cups and covered her tits with my hands. They weren’t big tits. They weren’t fake tits either. She’d grown these herself. They were soft and pliable. The nipples were long and hard. She arched against me as I stroked and fondled them. She moaned with pleasure. She reached for the waistband of my slacks. I pushed her hands away and pinned them against the bed over her head. I pulled her bra away from her chest and wrapped it around her wrists. It was a symbolic gesture but she got the message.
Now I lip nibbled my way down her neck and onto her chest. Her breath caught in her throat as I began to kiss the upper slopes of first one breast and then the other. I kissed and licked every inch of her tit flesh except her nipples. She whined -- frustrated by my deliberate teasing. She’d have her turn and I hoped she’d tease me as much as I’d teased her before the night was over. When I’d thoroughly covered her breasts with my kisses and licks I placed my mouth right above her left nipple and gently blew on it.
“FUCK!” Kathleen gasped. “FUCK!” She repeated as the tip of my tongue stroked the turgid tissue. “OH!” She cried out as I engulfed the nipple and its surrounding flesh with my lips and sucked gently. Oh I enjoyed sucking and licking her nipples. Kathleen abandoned the bondage pretense and wrapped her arms around my head, pulling me tighter against her breasts.
I don’t know how long this went on. A while. I enjoyed her responses. Eventually, I decided to move on. I kissed my way down her abdomen. My hands went to her waist. I found her skirt zipper and pulled it down. She raised her hips as I was tonguing her navel and I pushed her skirt down. I moved a bit so that I could get both hands on the waistband while still kissing her abdomen. Her skirt quickly joined the clothing pile. A garter belt, stockings, and panties were all that remained. A wet spot adorned the apex of the tent in her panties.
My lips were at her waist. I didn’t move to pull her panties down right away. I kissed and lip nibbled her through the thin silk, once again avoiding the most obvious target. When I had covered all but her bulge, I continued to move southward, kissing her thighs and inhaling her scent. I lifted her left leg and kissed it all the way to her stocking covered toes. I sucked each toe through the silk barrier. She squealed when I kissed and teased the sole with my tongue. Then I kissed my way up the back of her left leg, once again bypassing the obvious target and repeated the process with her right leg.
By the time I kissed my way back up her right leg to the top of her inner thigh, she was squirming on the bed and pulling on her nipples so hard I thought she’d tear them off.
“You are SUCH a fucking tease!” Kathleen gasped.
“You’ll have your turn, darling. I enjoy being teased,” I replied between kisses to her silk covered hips.
Patient man that I am, I have limits, and I wanted to see what was under that scrap of silk. So II gripped the waistband of her panties in my fingers and began to slowly peel them off. She lifted her ass and put her legs together. She wanted those panties off as much, or even more, than I did. Taking care not to snag her cock I slowly slid the filmy garment down her legs and off. I pressed them to my face and inhaled deeply before tossing them aside.
And there it was. Even in the dim light I could make out the last external vestige of what she’d been born with, sexually. It was substantial -- about six inches long and fairly thick -- and it was hard. The tip glistened with moisture. I went back to kissing the tops of her thighs, working my mouth into their junction intending to start with her balls. But when I got to where they should be, there was nothing. At the point where her penis protruded from her body there was only smooth skin. As my lips traced it I could feel the tumescent tissue under the skin reaching back into her body. No balls. She’d had them removed. As my tongue traced the flesh I found telltale scars indicating the place from which a scrotum once hung. Kathleen had gone the whole nine yards with her orchiectomy, not just having her testicles removed but also the scrotum. Kathleen must have decided not to have a full GRS. As I understood it the surgeons needed the scrotum flesh to form the labia minora as part of the GRS process. These random thoughts went through my brain far faster than I could write them or you can read them.
Kathleen trembled with need now and I stopped all pretense of teasing. I kissed my way up the shaft and took her cockinto my mouth. I licked it. I sucked it. I stroked it. I’d sucked bigger dicks than this but hers was special. She’d kept it for a reason. I loved how it felt all hard and throbbing in my mouth. A steady stream of seminal fluid leaked from its tip so I knew whatever surgery she’d gone through hadn’t had anything to do with her prostate. I decided to treat it like a clitoris.
“Oh ... fuck ... that’s good,” Kathleen moaned. “Keep doing that ... Oh Jesus ... fuck baby that mouth is magic,” she babbled. There was lots more where that came from. She was very verbal about her pleasure and I enjoyed that.
Having thoroughly coated her cock with my saliva I used my hand to stroke it while my lips and tongue sought unexplored real estate lower down. She got the hint and pulled her legs back and apart. I spent some time on the sweet spot between the base of her cock and her ass before putting my tongue right in the center of her crinkled opening and licking it.
I gently stroked her cock with my fist. My tongue worked on her rectal rose coating it with my saliva, teasing and probing it as I would a pussy. I worked my mouth back up to the tip of her cock and engulfed the shaft again. My spit ran down her cock and I gathered some of it on my fingers and pressed first one and then two of them into her bottom.
“Yesssss,” she hissed with pleasure.
She may have had her balls and scrotum removed but her prostate was still very much intact. This was familiar territory for me. I was experienced in prostate massage and I put that knowledge to good use now. I pressed my fingertips firmly yet gently against her happy spot and worked it in rhythm with my lips and tongue on her cock. I varied the speed of my strokes to keep her on edge as long as I could. It’s something I enjoy when someone does it to me. She moaned. She squirmed. She thrust her hips off the bed in what felt like an attempt to drive her dick through the back of my skull.
“Oh, God, Jim ... FUCK ... You bastard! Make me cum dammit!”
I smiled around her dick and decided to have mercy. Picking up the pace I drove her hard toward the finish line. It seemed like it would be a very short race.
“That’s it! GOD! OH FUCK! Don’t stop ... Don’t you dare stop! ... Gonna cum...”
I felt her ass clamp down on my fingers just as her cock swelled and stiffened further in my mouth. I tasted semen on my tongue as she pulsed and squeezed and pulsed some more. I enjoyed the salty taste of her ejaculate -- there was more than I expected -- and the way she stiffened and arched her body in the grip of her release. I savored her essence and swallowed it. I gripped her cock with my lips and kept pressing her prostate with my fingertips. She kept cumming. Her hands gripped her tits as waves of pleasure washed over her.
My cock was an iron bar in my pants. What I wanted to do at this point was pull them off and fuck this beautiful woman until I blew a huge load in her guts. But I didn’t do that. When Kathleen finally found my ministrations intolerable she pushed my head away and I pulled my fingers, gently, from her ass.
I maneuvered Kathleen further onto the bed. She looked up at me with hunger mixed with something else -- were those tears on her cheeks? -- while I quickly added my pants, socks, and briefs to the clothing pile. Naked, my cock a bow spirit aimed directly at her, I joined Kathleen on the bed covered her with my body, claiming her mouth for more kisses. She tasted her juices on my tongue and groaned into my mouth as we shared the flavor.
I kissed her cheeks and tasted the salt of tears confirming my earlier suspicions.
“Is something wrong?” I asked.
“No. Nothing’s wrong. Everything’s perfect,” Kathleen whispered, her voice trembling.
“Oh my god Jim. You have no idea. You felt my scars. You know what surgery I’ve had. I almost never get hard anymore. I get pleasure from being sucked and stroked. I cum, but not like that. That was fucking intense. Damn. There goes the eye makeup.”
“It’s dark. I won’t notice. And I promise not to tell anyone that I made you cry. (She laughed) I enjoyed giving you pleasure.”
“And now it’s your turn. Fuck me, Jim. Lube’s on the night stand.”