Bikeman's Bisexual Fantasies #1 "TS Helen" M/TS
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This is a work of fiction.
This is part of a series of stories that I call, "Bikeman's Bisexual Fantasies." The reason I do is that I'm bisexual, and these are my fantasies. Get it? Cool. The reason that I say that is that some of the stories aren't bisexual in and of themselves, that is, they do not contain any characters who, during the course of the story, engage in sex with at least one member of the opposite sex and at least one member of the same sex in some combination. This story, for example, has two main characters. One of them is male and the other is a preoperative transsexual, technically and biologically male, I guess, but I refer to her throughout the story with female pronouns. Sigh.
"TS Helen"
Generally I don't much go for picking up women in bars, but I was there unwinding from the long flight to a strange city and she was there as well.
There was a certain electricity when our eyes met, so I sat down next to her at the bar and we began talking about the weather, the local basketball team, and other pleasantries.
All the while, I was quietly drinking up her tall, thin frame and delicate features. She was dressed conservatively in a white turtle neck shirt, floral skirt and matching vest.
She was a tall woman, about 5'9", slim. I'd say, "just the way I like them," except that after two Johnny Walker Reds and a seven hour flight anyone with a nice smile and warm eyes was just my type. For the night at least.
"So," she asked, "what are your plans for the evening?"
"I thought maybe I'd find the hotel pool, relax, unwind, hit the hay." I said.
"I might be able to help you relax a bit, before you hit the pool, if you'd like."
"I'd like," I said, smiling.
We stood and walked to the elevators, once again slipping into meaningless small talk. The elevator doors opened and we walked in. She was saying something about some sensational play the point guard had made as we were walking past the TV when the doors finally shut and I could stand it no longer. I wrapped my arms round her waist, pulled her toward me and pushed my lips rather desperately against hers. She responded with passion, parting my lips with her tongue. Our tongues wrestled for the brief seconds until the elevator stopped and we released each other and walked down the hall, once again talking of basketball.
No sooner had the door to my hotel room shut than we were embracing again, holding each others bodies tightly. We pulled apart again and walked to the center of the room next to the bed. I placed a hand tenderly on her cheek and kissed her lightly on the lips, then playfully licked at them. She smiled, placed her hand behind my head and firmly pulled my face towards her lips. This time we opened our mouths and caressed each others tongues. I had been holding her around the small of her back, but now I let my hands roam around her back, feeling her shoulder blades, her butt, caressing the back of her thighs. I felt like a kid in a candy store. My dick was straining at the front of my slacks already.
In the meantime, she pulled her arms in front of herself and felt my chest, lazily undoing buttons so that she could tweak my nipples and roam around my chest with her hands. She lazily licked my ear lobes and bit at them playfully. I caressed her butt underneath her skirt, then started moving up her back, under her sweater. I moved my hands up under her armpits and caressed her breasts with my thumbs. They were small and hard,like a young woman's. I hadn't felt breasts like that since I was a teenager. They were still encased in a delicate lacy bra. I moved my hands around behind her and unclasped her bra.
Our lips were still exploring each others face and neck with animal passion. I pressed my mouth into her slender neck and moved my hands forward so that I could caress her breasts. Her nipples were small and very hard. I started kissing down the front of her sweater so that I could get to those wonderful little breasts, but she arched her back away from me and pushed my head back so that I sat down rather abruptly on the edge of the bed.
She kneeled in front of me and began undoing my belt. I leaned back and propped myself up on my hands. This was all too good to be true. I lifted my butt so she could pull down my slacks and boxer shorts, but she didn't have to pull them far before my hard cock jumped out like a girl from a stag party cake. She grabbed it with both hands and began circling the head with her tongue. Then she slid down on it. she stuck her tongue out to cover her bottom teeth and rolled her top lip over her top teeth and plunged her head down until the tip of her tongue was touching my balls. She curled her tongue to get the maximum amount of tongue-to-cock contact, then began bobbing her head up and down on my cock. This woman had sucked a cock or two before.
All that I could do was lean my head back and clench my teeth. I don't know if it was minutes later, or only seconds, I felt the familiar tug in the testicles that told me the ride was soon to be over. "Wait a minute," I said, "hold on a second, not just yet, stop, please..." I said, although it took me several seconds to choke out each word as my breathing had become somewhat erratic.
"Mm-mm," came her muffled replay. My jism left me in rough, pulsing motions and my arms collapsed behind me. As I laid back on the bed I heard her say, "Are you relaxed now?"
"Mmmmmm," was my dreamy reply.
"Then I'm done here," she said.
I opened my eyes to find her straightening out her rumpled skirt and slipping back into her discarded shoes. I jumped up and caught her around the waist and pulled her on top of me on the bed. I rolled her underneath me while saying, " You might be finished, but I think I owe you one."
"No, please, don't!" she said, but by this time I had already pushed her skirt up and hooked my fingers in the top of her cotton panties. I looked down to seewhat she was protesting about and saw the distinct bulge of an erect cock in her panties.
"What is this!?" I said.
She sat up on her elbows, tears forming in her eyes and said, "I am so sorry. Please don't hurt me."
"I wouldn't dream of hurting you," I said, and I moved up the bed and kissed her once again, this time very lightly on the cheek.
I gently wiped the tear from her left eye with my right thumb and said, "This is a bit of a surprise, but I think I still owe you something for that wonderful blowjob.
She started sobbing then, so I quickly moved to sit beside her. I held her close to me and she buried her face in my shoulder.
"I'm so sorry for this, but this is a hard time for me, and I get so lonely. None of my old boyfriends will speak to me. Hell, none of my old girlfriends will speak to me. All I want is to be a woman, to be treated and loved as a woman. Now I'm so close and I just don't want to wait any more. I just needed someone to react to me sexually, to be with me sexually. I'm sorry."
I kissed her on the forehead. Despite having just received the best blow job of my adult life, my cock was twitching again. This woman with the surprise in her pants was getting to me. "Well, I believe that I owe you one, what would you like me to do?"
"What do you mean?" she whispered.
I wrapped my arms around her and kissed her hard on the lips, pushing my tongue into her mouth and holding her tightly. I didn't want her to misunderstand.
"Oh," was all she said.
I pulled the sweater up and she responded by raising her arms. I left her lips for a second as the cloth passed between us, then pushed her back onto the bed and buried my face in her neck. She hadn't had a chance to replace her bra in her hurry to leave, so her small breasts were inviting and teasing me. I immediately attacked them with kisses and licks. I sucked and licked her left nipple until it was erect, then went to work on her right.
She closed her eyes and went to work on her skirt. When it was around her ankles she shimmied out of the panties, then kicked the whole mess to the floor. I moved back up to her neck with my shower of kisses, and let my body gently down on top of hers. She was shorter than I, so her cock pressed into my stomach. This was a strange feeling. I was making love with this beautiful, slim woman with small, hard, well defined breasts, a gorgeous little butt, and a small, but apparently still fully functional cock.
I rolled onto my side to get a look at her. "You are a very beautiful woman."
She laughed. "Thanks," she said, "Hold on a sec."
She stood and walked over to her purse. She bent down deliberately, seductively, keeping her legs straight and close together to show off her cute little butt. She found what she was looking for, then opened her legs and looked back through them at me. "What are you looking at?" she said with a smile, and joined me again on the bed.
I pulled her down to me and rolled over on top of her once again. She tucked her heels up close to her butt so that her legs made little wings with her knees in the air and this time as I explored down her neck to her breasts, I didn't stop, but slowly descended her abdomen with kisses and caresses. She was fooling with what she had retrieved from her purse, which was a small tube of K-Y. As I explored the bottom of her rib cage with my tongue, she began working her fingers into her ass, first one, then another.
I stopped momentarily at her belly button and playfully fucked it with my tongue as she continued to stretch and play with her ass. I realized that I was stalling just a bit. I was hesitant to have that first contact with her little dick. When I realized this I felt a bit sheepish. This woman had unselfishly given me a wonderful blowjob and I was hesitating to return the favor.
I delicately licked at her cock, like a child unsure of whether he likes this flavor of ice-cream, and kissed it rather gingerly. She laughed. "I don't want to rush you or anything, but it won't bite."
"I know," I said, and I started to say something else, but she interrupted me with, "Take your time, and enjoy."
I smiled. I stuck out my tongue and started way down at the base of her scrotum and licked all the way up to the top of the head with a firm lick. "Mmmmm..." she said, "Now you're getting somewhere."
I started licking her cock head with fast, firm flicks of the tongue, then I opened my mouth and took as much of the shaft as I thought I could into my mouth, but I was touching it with only my lips. "Put some tongue into it." she purred.
I wrapped my lip over my top teeth and plunged my head down onto her cock as she had earlier for me, but when the blunt tip of her cock hit the back of my throat I felt an unwelcome gag reflex trying to force it back out. "Mmmm," she said, "don't try to do to much your first time.
She now had both hands exploring her butt, and was stretching her asshole with two fingers on either hand. I pulled my head up until the only thing I had in my mouth was the head and I grasped the rest of the shaft with my hand and began bobbing my head up and down so that my tongue caressed the delicate underside of the cock head. "Mmmm," she said, "Yes. You sure you've never done this before?"
I closed my eyes and went to work earnestly on her cock. Soon I felt her pushing my head away. "I want you to fuck me now," she said, rather abruptly. She pulled my face up to hers and kissed me on the lips. In the same motion, she lifted her hips from the bed and slipped a pillow under her ass.
"I want you to fuck me face to face."
I moved up to get myself in position and put my cock against her asshole. "Hold on a second," she said, and I felt her rubbing K-Y onto my cock. It was cold, but her hand felt good. I pushed my cock forward into her ass. There was a little resistance at first, then it slid in.
It was warm and tight and wonderful. I closed my eyes and a little involuntary shudder went through me.
"Kiss me, please."
I kissed her gently on the lips and began slowly pulling out, then slowly pushing in. She was underneath me with her eyes closed, her breath slow and raspy. I began to increase the tempo. Little gurgles and sighs and moans met my various thrusts and withdrawals. I lowered myself to my elbows and kissed her on the lips. My kiss was met by a brief kiss and a lick, then she turned her head and moaned softly. I continued to kiss her neck and cheeks as she tossed her head from side to side.
At times I would lift up from her so that I could lick her breasts, at others, I would deliberately lower myself to caress her cock with my stomach. I was getting close to orgasm and I gave it away with some deep breaths and guttural growling type sounds. Her hand went down to her cock and began rubbing it vigorously.
She wasn't stroking it as if it were a cock, but rubbing it with an open hand as if it were a clitoris.
I started fucking her ass harder and faster. I felt that I was getting really close to spewing and I wasn't ready yet so I slowed down and bent down and kissed her lips. she reached up with her free hand and grabbed the back of my head and pulled me close. "Kiss me while I'm coming." she said breathlessly.
I pressed my tongue into her mouth and her tongue began wrestling firmly with mine. I put a hand on each side of her waist and started stroking more quickly and deeply again. She was making noises in the back of her throat and then her tall body went tense and she pushed her small hard cock against my stomach and pushed it back and forth like a wind shield wiper across my stomach. I felt her jerk a little, she gasped, and shot a small load, some of it spattering my stomach, most of it landing in hers.
I closed my eyes, arched my back, and came as deeply inside her as I could. I shuddered as each spurt of come jumped out. When the spasms in my cock subsided. I pulled out and collapsed beside her, nuzzling my nose into her neck.
After a few minutes just lying there, she asked, "Do you still need to go for a swim?"
"I think I'm as relaxed as I'm going to get," I said. I kissed her deeply on the mouth. "You are one hell of a woman."
She smiled and looked into my eyes. There was sort of a scared look in her eyes. "Can I stay with you tonight."
I smiled. I'd like that. I rolled over and grabbed the phone. I made a quick call to room service and ammended my breakfast order. "Shall I change your bill to double occupancy as well?"
"Yeah, I guess you better."
When I awoke in the morning we two were still spooned together. I nuzzled into her neck and remembered our evening. Thinking about it made me stiffen. As my cock got hard it pushed against her legs. I pulled my butt back and my cock sprang up and as I moved back into place my cock nestled in between her firm ass cheeks. I slid it back and forth a couple of times between her ass cheeks. She stirred. "Mmm," she said, "good morning to you too."
She kicked the covers off and flipped around started licking at the head of my cock. Her small cock was hanging limply in front of my face. I took her soft cock into my mouth and swirled it around my mouth. "mmmm," she said, "If it doesn't get hard, it doesn't mean I'm not enjoying you. It's the hormones. Sometimes it gets hard now and sometimes not. I can have an orgasm without it ever getting hard."
I just continued to play with the head of it in my mouth and lick her soft shaft and testicles.
She went to work on my cock, grasping the base with her hand and bobbing up and down very quickly. She wrapped her lips over her teeth so there were no sharp edges and pistoned up and down on my cock.
I couldn't return the attention in kind because, though her cack was a little thicker and stiffer than it had been when I started, it was still not going to work for that. Instead, I pressed the head of it firmly against the top of my mouth and lapped at with my tongue and rolled it around my mouth.
She was apparently intent on getting me off quickly as she continued with the same intensity even when I started moaning and tensing. I opened my mouth and let her cock fall out as I came. "Oh my, oh, oooooooooh." I said as I shot a hot load down her throat. She continued to suck on my cock until the post-cum tenderness made it too much and I had to pull away.
She sat up on the edge of the bed, then layed back so that her ass was hanging off the edge. "Finish me with your fingers in my ass. I like the feeling of being filled."
I grabbed the K-Y from the nightstand and lubed my fingers, then got on my knees on the floor. I inserted my index finger into her ass, then quickly worked up to two, then three fingers. She started rubbing her cock vigorously as she had the night before, but with my free hand I reached up and stopped her. I took her small, limp dick into my mouth pressed it up against the top of my mouth and vigorously worked the underside with my tongue. She reached down and grabbed my head and pushed me hard against her crotch. A few seconds later, she arched ner back and pushed on my head even harder. I felt a couple of small squirts against the top of my mouth and tasted her sweet, salty cum. I pulled my sticky fingers out of her tight little ass.
I moved up to the bed and kissed her neck and breasts.
There was a knock at the door and the bellhop yelled, "room service." I quickly donned my shorts and grabbed my wallet. I was still a little stiff so my cock pushed out against my shorts and several drops of cum seeped through from the inside.
The bellhop acted as if there was nothing even remotely strange about a half naked man with a partial stiffy answering the door. He described my breakfast order, asked which paper I wanted, and stood looking me in the eyes as I fumbled for his tip. I tossed in an extra buck over my usual for his professionalism, and closed the door.
I realized that I didn't even know her name. I sat down on the edge of the bed and asked her. "Helen," she said, "my name is Helen."
"Well Helen, breakfast is served."
We ate breakfast more or less in silence. Every now and again I'd look at her and she'd be looking at me, smiling. She'd smile and look away. I felt like a high school kid flirting with the prom queen in the the cafeteria.
After breakfast she went in to the bathroom and turned on the shower. I went in behind her and looked at her long vouptuous legs and her ass, so petite and perfectly formed. I realized my cock was twitching again. Christ, I hadn't cum three times in 12 hours since I was teen ager, but staring at this tall, beautiful woman from behind as she adjusted the shower, there was no denying that I was getting hard again.
She stepped in to the bath tub and started running her fingers through and wetting her long dark hair. I stepped in behind her, wrapped my arms around from behind and began fondling her small, hard breasts. She leaned back and I pushed my face into the soft crook of her neck. I kissed her and drank the warm water that was cascading over her dark skin.
She was slightly shorter than I but had longer legs so my cock nestled into her ass crack. "There's just no satisfying you, is there."
"I'm very satisfied, thanks, but you're just so sexy I can't help it."
"OK, well, I should be still lubed enough from this morning. Knock yourself out."
With that she leaned forward and rested against the wall of the shower stall with her hands. I grabbed her waist and guided myself into her ass, then leaned forward and grasped her breasts and started slowly pushing in to her. The water cascaded over the both of us as I kissed the back of her neck, cheeks, ears, lips. I was slowly drawing in and out, in and out.
I had been dreamily massaging her breasts, kissing her head and neck, and slowly grinding away at her ass for an unknown amount of time when she suddenly stood up a little straighter and said, "Fuck me hard."
She didn't have to ask twice. I grasped her thin waist and started plunging in and out for all I was worth. I started to feel the tenseness and the aching soreness in my balls that told me that the last load for a good long while was coming her way. I pulled almost all the way out, then slammed back in hard, then repeated the process. On the fourth or fifth slam my balls tightened. There is a certain pain associated with the third or fourth time I cum in a short period. It is a wonderful sort of pain that I'd always likened to how difficult it was to get the last few bits of toothpaste out of the tube, like my balls were really being squeezed by some unseen hand.
A couple of measly little squirts and I was spent, my breath coming in ragged jerks. I just lay down on her back and massaged those small, firm breasts.
After a few luxurious moments like that I stood up and withdrew. During the shower we playfully soaped each other and flirted shame- lessly.
We both dressed and as she was heading towards the door I caught her by the waist and wrapped her up in my arms. "I won't pretend that I've never picked up a stranger in a bar before," I said, "but I have never felt this... sad when someone I barely knew was leaving. This whole thing was very wonderful."
"You made me feel very special."
"Would you like to go to dinner with me tonight? Just dinner, I don't know if I have anything else left."
She smiled. "That'd be nice." She scribbled a number on a hotel pad the desk and left. It would be a long day waiting...