tagTranssexuals & CrossdressersMike and Chris Together

Mike and Chris Together


NOTE: This is my entry in the 2012 Literotica Valentine's Day Contest, and it is about a man having sex with a male to female transsexual. They basically take turns fucking each other in the ass. If this kind of activity bothers you, you should probably stop reading this story now.


Mike's sex life had taken a definite series of turns for the worse. When he called one of his favorite partners, Stella, she apologized for not returning his earlier calls, and told him she had been very busy lately.

"I'm really sorry, Mike. I've had some great times with you, and I will always appreciate the way you made me feel like a desirable woman again. I paid too much attention to my bitch of a niece, Monica, and she convinced me I was too old and fat to ever attract a man. You proved she was wrong. So did the other guys I started dating and making love with, but you were my first guy in a long time, and the man who showed me I was still attractive to men who like real women. I'm engaged now, to another great guy who loves me for myself, so I've had to stop seeing the other men in my life. I hope you don't mind."

"Not at all, Stella, and I wish you the best. You can tell your fiancé, from me, he's getting a great woman, and I hope you'll be very happy together."

"Thanks, Mike. I'll tell him that, but I hope you don't mind if I tell him you're just a teacher at my niece's school and a good friend of mine."

He had also tried to line up another session with Jenna. He had never had his cock in either her mouth or pussy, although she did always masturbate him during their times together. What Mike liked about her was her strapon dildo and how she used it to fuck him and, presumably, other men in the ass. It was an erotically kinky thrill, and he was used to calling on her every week, until she cut him off.

"I'm sorry Mike, because I've really enjoyed our times together, and I know you have too. Monica is making me stop seeing you. I don't know what she has on you, but if she rats me out I could go to jail for a long time, so I have to do what she tells me. You know, you can buy a dildo, and it'll do the same thing as my strapon does."

Mike was aware of what a dildo could do, but he was actually repulsed by the thought of using one on himself. He is not gay, although he loved the feel of Jenna reaming out his ass with her plastic toy. She is, after all, a woman, even if she is skinny and homely, and sex of any kind with her would always be heterosexual. He is aware of a certain contradiction in his attitude and opinion, but he had no interest in changing it. What he did have was a desire to find another woman who liked pegging men with a strapon or similar toy the same way as Jenna does, but he didn't know how or where to do that.

He still had Chris, and the thought of her loveliness and sweetness always made him feel warm inside. The auburn-haired beauty was the third woman, besides herself, whom Monica had blackmailed him into seeing for sex. She, herself, was the first one, and a student in his American History class at the high school where he taught. Her ploy was to threaten to accuse him of trying to rape her. There was no credibility to her threatened claim, but an incident in his background, which he wanted to keep out of the public notice, led him to go along with her demands. They had both had a great time in his bed, and his mouth and cock brought the extortionist to two orgasms every time they got together, but she seemed to take offense that he would enjoy their sessions too.

Their second time together had, supposedly, been a threesome with Jenna and, while he was fucking Monica, she used her arms and legs to hold him in place on top of herself long enough for her friend to slide her dildo into his ass. It was a new experience for Mike, and a very enjoyable one. Much to the discomfiture of the extortionist, he arranged future dates with Jenna and her strapon, until the young woman was forced to halt their fun times. The third try was a date with Monica's aunt, who was twice as old as Mike and somewhat overweight.

This attempt resulted in Monica being pissed off even more than she had been after the debacle with Jenna. The man she had begun thinking of as her enemy was not taken aback by Stella's age, and he regarded her as pleasantly plump, and not in a euphemistic way. Some of his favorite memories were sex with larger, older women, and Monica's aunt and he had a great time together, that night and several times after that. Even worse in the mind of the vindictive girl was the fact her aunt no longer asked her opinion on matters sexual, preferring to use her own good sense and the experience gained throughout her life.

The attempts involving Jenna and Stella were nasty, but Monica's third effort was almost vicious. She was still able to blackmail Mike, and she ordered him to pay a call on Chris, whom she described as a beautiful young woman. The description of her was accurate, and she was horny as well. Their making out session was hot and heavy, until Chris raised her mouth from around Mike's cock and suggested they get more comfortable on her bed.

Once there, and while in the process of undressing each other, Mike learned to his chagrin the woman in bed with him had a cock that was almost as big as his own. She was a transsexual, or T-girl, and Monica had neglected to tell him that. She had also not told Chris about his ignorance in the matter, thereby distressing two people at the same time. Mike would have taken his departure, maybe even stormed away in anger at being deceived, but he had become quite fond of the very sweet and beautiful young woman, and was dismayed when she seemed to be on the verge of crying at his apparent rejection.

He decided to give her what amounted to a sympathy fuck in her ass that night and never see her again. That was his intention but, once he started doing it, they were having such a terrific time together he even stroked her cock until she reached her orgasm and shot her semen onto a towel she had placed on the bed. Seconds later, he enjoyed a great climax of his own. Still later, while on her couch again, she expertly sucked him off and he filled her mouth with his cum. The sex with Chris had been fantastic, probably the best he had ever had, and they agreed to meet every Tuesday night in the future. She worked as a cocktail waitress in a bar catering to GLBT people, and Tuesday was her only night off.

Mike thought so much of the sexy T-girl he did some research online and, the next time they got together, he referred to her ass and cock as her pussy and clit. The sex that second Tuesday night was even better than their first time together, and a deeper feeling than lust started growing between them. After that, their relationship became much more than just fuck buddies, and he took her out to dinner and to shows and dancing. They joked, but on the square, that either of them could always tell when the other was horny and eager for sex, and the telltale sign was the same for Mike as it was for Chris.

The fact that his ass had not recently been fucked by Jenna's strapon did not bother Mike the next time he called on Chris. The weekly reaming was fun, and had been an enjoyable part of his sex life, but it had nothing to do with his deepening relationship with the lovely T-girl. That Tuesday happened to be Valentine's Day, and he came bearing flowers for her. As they always did, they greeted each other with a warm embrace and passionate kiss, and it wasn't until their lips had been pressed together for several seconds that their tongues also renewed their very cordial acquaintance.

"Hi, Mike. I'm sure glad to see you again, as if you couldn't tell," she quipped, after breaking off the kiss while remaining nestled in his arms. To Chris, that was the best place in the world to be, in the embrace of the sweet man who always makes her feel like the desirable woman she truly is.

"I'm glad to see you too. Is there any special place you want to go or anything you want to do?"

There was something she wanted to do, and it was the same thing they did at the end of all their dates, but he already knew that, so she didn't mention it. "There's this new Italian place near the mall. I've heard their pasta is really great and they have a good dance band."

"Okay. Let's give it a try."

Chris went to get her coat, and Mike helped her put it on. The assistance was not needed, but they both like little things like that during their time together. The mall with the new restaurant was a short drive away, and their wait to be seated was less than they expected. The food lived up to its reputation, and the glasses of Chianti were perfect. Mike didn't drink much, because he would have to drive them to Chris's house, and she didn't overdo it either. They very much enjoyed holding each other tightly, as was their usual preference, while moving around on the small dance floor.

Many of the other men in the café felt twinges of envy for Mike, because he was with such a beautiful woman, with auburn hair, a lovely face with fine features, a creamy complexion and a sexy figure in her blouse and loose-fitting skirt. She always wore such garments when she was out with Mike so nobody could see her erection, if one developed, and know her status as a T-girl. Many of the women in the restaurant were envious too, of Chris, because of her beauty and because she was escorted by the tall, handsome young wavy-haired man who seemed to be so devoted to her. If the striking couple knew about the envy they aroused, it didn't bother them. As they held each other closely on the dance floor, Mike felt Chris's clit start to stiffen and press against his crotch, and he knew his cock was doing the same in response.

"Ready to leave?" he asked her, because he knew she was.

"Yes. And I can tell you are too." She grinned lewdly, because they both knew what they would be doing as soon as they returned to her home.

Neither of the horny people wanted to delay what they both considered the best part of the date, so Mike paid the check while Chris was making herself even more beautiful in the ladies' room. When she returned, he was waiting for her, and they hastened out to his car in the parking lot. Although in a hurry, he drove under the speed limit, because he didn't want to risk the annoyance and the lost time a speeding ticket would have entailed. When they reached her small house, she unlocked the door, locked it again and kicked off her pumps after they were inside. He removed his shoes also.

She turned to face him then, and they shared the close embrace and the long, loving kiss they had both been wanting for the last couple of hours. As their tongues and lips continued their mutual gymnastics, they sidled toward the sofa where they had gotten into the habit of beginning their serious romancing. As soon as they separated their lips, they sat down and moved into another tight hug. The sofa was the place they sat their first evening together before retiring to Chris's bedroom and since then, it had always seemed fitting things should continue to start there.

Chris's hand slyly reached out to do one of those things. Finding the zipper on Mike's pants, she pulled it down and, after he spread his legs to facilitate her entry, slipped her hand inside to gently hold his burgeoning cock. It had been almost fully erect on the dance floor, but had softened somewhat during the drive to her house. With a few strokes of her hand, it was rigid, and she quickly knelt in front of Mike to remove his socks and take his cock into her mouth. This was a preliminary; she would suck him off later, but Chris liked the feel of his erection in her mouth before taking it into her pussy, which was what they both called her ass.

After a minute of sucking his cock, relishing the way it spread her lips open and filled her mouth, Chris leaned back on her heels and smiled up on her beau. "Ready to go to the bedroom?" she asked, although she already knew the answer.

He smiled, stood up and offered his hand. "Let's go," he responded.

With their arms around each other, they entered the bedroom, leaving the door open. She turned on the light; they would leave it on, because that was the preference of them both. They stopped beside the bed, which she had prepared earlier, and shared a long kiss before beginning to remove each other's attire. In a matter of seconds, there were two bare naked people in the room, standing beside their cast off clothing. They are both aware beds are for lying on, not standing beside, and they were horizontal in a few seconds, still wrapped tightly in each other's arms.

Chris rolled over onto her back while Mike knelt beside her and started licking one of her adorable nipples, which had already stiffened. He always loved the feel of the pink nubbins under his tongue, especially when they were as erect as they were then, so hard he could feel the individual ridges as well as the pebbly texture of her areolas. His mouth alternated between them while Chris's body began squirming under him and she started cooing in joy. Mike would have been making the same kind of happy sound, except his mouth was full, for he had drawn one of the precious orbs into his mouth and was sucking on it while his tongue continued caressing the nipple and areola.

Again, his mouth switched back and forth while Chris's arousal increased and her joyful noises started evolving into moans of bliss. Her body was moving under him and, when he glanced down at her crotch, he saw her clit, fully erect, waving from side to side. The lovely T-girl was as aroused as she would get, and it was time for him to continue to escalate their sexual pleasure.

When Mike straightened up, Chris knew what he wanted to do next, and it was what she wanted more than anything else just then. Before his arrival, while making the bed with just a bottom sheet in anticipation of what they would be doing, she had placed condoms and Aqualube on the dresser, She pointed them out to Mike, and he got up to get them, also bringing back a damp hand towel from the bathroom. By the time he returned, Chris was on her hands and knees in the center of the bed. There was a pillow under her face, which she would hug while fucking back to meet his strokes and a towel in front of her, which would catch her semen as she climaxed and ejaculated onto it.

When he knelt behind her, she reached back to spread her cheeks to start the preparation. As he always did, Mike marveled at the beauty awaiting him, the lovely round cheeks, smooth and creamy white with her adorable rosebud in the center. Before starting, he kissed the perfect hemispheres, thinking of how he usually liked to eat a woman's pussy. So far, he had not done that with the beautiful T-girl, but some evening they would shower together, and he would take particular care back there so he could apply his tongue to her pussy in advance of his cock. He truly enjoys their time together, and likes to think of ways their superb sex lives can be improved.

But eating her pussy would still be at least a week in the future. That evening, after he had rolled his condom into place, his left hand reached between the creamy mounds and the fingers and thumb pried open her precious pink rosebud, while his other hand held the squeeze bottle of Aqualube. He wiggled the tip into the tiny hole being created and squeezed in a big dollop of the lubricant. Smiling as Chris quivered with anticipation, he inserted the middle finger of his left hand all the way to the knuckle and spread the oily liquid evenly all around as far in as he could reach. When she was ready, he covered his cock with the Aqualube and moved in closer, until he felt the tip making contact with the pink hole he was about to start fucking. Chris kept holding her cheeks apart, while squirming with the exquisite pleasure she was about to experience.

Before thrusting forward, Mike moved his cock up and down, spreading the lubricant better and starting to make a slight penetration. When he was sure all was in readiness, he gave a short, firm push, and sighed happily as his cock drove through the tight ring of muscles. For a few seconds, he stayed in that position, before thrusting forward again and plunging more of his shaft into where it was wanted so much.

Chris derived extreme delight from the initial penetration that forced open her tiny rosebud and sent waves of joy sweeping through her body. The second stroke was even better, as Mike's hard, thick cock also expanded the adjacent channel, but the third one started massaging her prostate gland, which she thought of as her rear clit. Billows of pleasure inundated her body, and she moaned in bliss and prepared to fuck back to meet the next thrust.

Enough of his cock was buried in the T-girl's pussy that Mike no longer needed to steer it, so he used his fingers to check around it to make sure there was no loose skin or other potential problem. Finding none, he wiped the excess lube from his fingers, placed his hands on Chris's soft, white hips and drove forward again. When she felt his cock surging into her, she fucked back to meet him, and most of his shaft burrowed into where it was wanted and needed. She let out a blissful moan as the hard cylinder raked over her rear clit, and he sighed happily at the sensation of her internal muscles squeezing and releasing his cock.

The next stroke felt even better to both horny people, as did the succeeding ones. A few minutes later, his shaft was buried in her pussy so deeply she could feel his pubic hair as it tickled the insides of her cheeks. She could also feel her front clit as it grew erect from the excruciating pleasure Mike was giving her. Later, when it had become fully erect, she wanted and expected him to stroke her there until she had her orgasm and shot her sperm out onto the towel under her body, but she knew that would be a while yet.

Mike was having so much fun fucking the lovely T-girl, he hoped it would be a long time before he climaxed and brought her to one with his hand. Moving slowly to make it last as long as possible, he drove his cock in and out, every stroke plunging all the way into her pussy, until his balls brushed against hers. The Aqualube had fully liquefied and was working perfectly, so there was no friction at all, just the delightful squeezing and releasing of his cock by the muscles inside Chris's love channel.

"God, I love that," she murmured, in between her moans of bliss.

"Me too. And I love you too."

Mike was surprised at hearing himself say that, until he realized it was true. He really did love the sweet, beautiful T-girl who was kneeling in front of him and fucking back to meet his thrusts into her pussy. He didn't know how or when that had come to happen, but a great feeling of peace and wellbeing came over him following his admission, and he repeated himself.

"I really do, Chris. I really do love you."

"I love you too, Mike. Really."

The fucking continued after this exchange, but it seemed somehow different, with a new and higher level of closeness between them. With his cock buried to the hilt, Mike leaned forward to embrace the woman he loved and to fondle her breasts. As he leaned back again, his hand contacted her fully erect clit, and he wrapped his fingers around the erection and started stroking in the same tempo as his thrusts into her. That was when he realized something else. He had been thinking of the organ in his hand as her clit, because Chris is a woman, and women don't have cocks but, anatomically, that's what it was. Except for being smaller, what he was gently massaging in his hand was just like his own cock, even to the point of both of them having been circumcised.

And that meant it was almost like Jenna's dildo, and could do the same things for his ass as Jenna would no longer be doing. Maybe even more. That skinny bitch was just interested in her own fun, and got off on what she described as "pegging" him. Chris was sweet and loving, and they could very well have a new kind of pleasure they could share. He released her clit, returned his right hand to her hip, and drew back and thrust his cock forward again.

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byBoxlicker101© 7 comments/ 51261 views/ 28 favorites

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