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Mike and Chris Find Each Other

12

For more background on this story see "Pet Teacher", "Mike Meets Jenna's Strapon" and "Monica's Aunt Gets Some".

One Tuesday afternoon, Mike Harris sat in his office correcting the pop quiz he had given to his American History class that day, but his thoughts were mostly on Stella. He had a date with her on Friday and they were both cheerfully aware it was strictly for sex, just as his introduction to her had been just for sex.

Monica, one of his students, was blackmailing him into sexual activities she thought would be unpleasant experiences for him but her attempts had backfired so far. The latest had been her Aunt Stella, whom she thought of as fat and old Mike had found her to be sexy and voluptuous, just what he liked, and her sexual knowledge and skill far outweighed her age.

Before that there had been Jenna who had used her strapon on the teacher's ass. That had felt so good to him that he had seen her twice since then, and their next meeting was scheduled for Saturday afternoon. He was looking forward to the end of the school year so he would have more time available to enjoy sex with these two women.

Although he had very much enjoyed the dates that Monica had set up, and the sex with her had been good also, Mike was aware that her enjoyment, sexual and otherwise, had been her goal, not his. Therefore, he was not at all happy when, unannounced and uninvited, she walked into his office, shut the door behind herself and sat down.

"Hi, Mike. I hope you're not too busy. I got another hot date lined up for you."

"Hello, Monica. Yes, I am busy. I have to correct these test papers from today. I've already finished yours and you did so badly I was tempted to flunk you."

"You better not, if you know what's good for you. You better not stand up Chris, either, if you know what's good for you."

Who's Chris? Don't worry; I gave you an "A". I didn't realize it was your paper until I saw how almost everything was wrong, and after I saw your name, I didn't bother to read any further."

"Okay, then. Chris is a friend of mine and a really good-looking woman. She works as a cocktail waitress but she's off on Tuesday night. This is her address and I told her you would be there at eight o'clock so you better do it."

"Okay." Mike accepted the scrap of paper containing an address, thinking how glad he would be when Monica graduated so he would no longer have to do her bidding, for fear she would tell the school board about their sexual activities together. He didn't know anything about Chris but he definitely put no faith in Monica's description of her as a "really good-looking woman".

Therefore, he was extremely surprised when, after ringing Chris's doorbell, it was answered by a tall, beautiful woman with auburn hair cascading over her shoulders, green eyes and fine, regular features. She was wearing a short skirt, showing long, smooth and shapely legs and a silk blouse with creamy breasts burgeoning over the low-cut neckline.

"Chris?" he asked, unable to believe his eyes.

"Yes. You must be Mike," was her answer in a low, seductive voice. "Come in. You're just as handsome as Monica said you were."

He accepted her invitation, walking through the door and into her warm, eager embrace. As Chris hugged Mike, she reached behind him to push the door closed, and when that was accomplished, she gave him her full attention. With their mouths plastered together, her tongue sought entry to his mouth, and was not denied. Even as Mike kissed the lovely woman, in his arms, and felt her soft breasts against his chest, he wondered what Monica was up to. He also wondered why such a beautiful and sexy woman as Chris would have any need to be fixed up at all.

"Come into the living room, Mike, and let's get better acquainted." She turned the knob on the door to activate the dead bolt, obviously wanting no interruptions.

As Chris led the way, Mike couldn't help noticing her ass. He is a man who appreciates female beauty in all its many forms but he is especially attracted to shapely asses, and the one he was following was one of the sexiest he had ever seen. He still couldn't help wondering what kind of shenanigans Monica was trying to pull this time, and he knew for certain that she was up to no good, but he decided to continuing going along with what so far seemed to be incredibly good luck.

Sitting on the small love seat, with just enough room for the two of them, their session quickly evolved from kissing to petting. When Mike put his hand on one of Chris's breasts, she stopped him, smiled and asked, "Why don't you take off my blouse and bra first? You'll like my boobies a lot more when they're naked, and they'll like you a lot more too."

Her suggestion was eminently sensible to Mike. A few fumble-fingered seconds later, she was nude above the waist and his fingers and tongue were caressing her breasts. Chris's nipples were pink and small, but fully erect, and their tiny, hard ridges felt good as he licked them with broad strokes of his tongue. Her breasts were smaller than they had seemed; she must have been wearing some kind of pushup bra, but they provided two very nice handfuls.

Two very nice mouthfuls too. Mike drew one into his mouth and gently sucked on it. He could hear hard breathing and sighing while his lips formed a seal on her soft flesh and his tongue caressed her nipple and areola. Chris's upper body was squirming on the sofa, presenting her other breast to him so he accepted her offer. This one was treated the same as the first had been but all the while Mike was immensely enjoying himself, he was still wondering what kind of a mean, nasty trick Monica was trying to pull and what would be the catch in what had seemed so far to be a perfect date with a beautiful and extremely amorous woman.

As much as he tried to put the notion out of his head, he couldn't completely do so. His mouth alternated between the two shapely breasts for several minutes until Chris, obviously in a high state of sexual arousal, whispered "My turn now," and pulled away.

She stood up and quickly got to her knees between Mike's legs to begin unfastening his pants. It was obvious what Chris had in mind and he decided to help the scenario along by removing his shirt. By the time he had tossed it aside, she had pulled his pants and underwear down to his ankles and was untying his shoelaces. When he was completely naked, even including his shoes and socks, Chris smiled up at him as she fondled his cock, which had been erect ever since they had started kissing.

"You've got a really nice dick," she told him. Chris further expressed her appreciation by licking the head and around the ridge of that nice dick. "Good and hard too. Monica said you were really hung and she sure had that right."

Before Mike could inquire about her relationship with his nemesis, Chris's eager lips had enveloped his cock and the tremendous pleasure he was immediately getting from her drove all other thoughts from his mind. Slowly, her mouth made love to his cock, letting the hard shaft slide between her lips until, with every stroke, the tip was pressing against the back of her throat. The caressing of her tongue on the entire length and her lips providing perfect pressure on his cock gave him incredible pleasure, making him squirm in his seat. The way she was sucking was a visual delight also. While Chris knelt in front of him, her auburn covered head bobbing up and down while his shaft slid in and out of her pretty mouth was one of the most erotic things he had ever seen.

Although they were both having a wonderful time, she had better things in mind. "Mike, your big dick is just wonderful and so are you but I really need to get this dude in my pussy. I hope I can suck you off too, but I'll do that later. What I really need first is a good fucking. I haven't had one for a long time." He nodded his head in full agreement. There was no objection whatsoever to this lovely woman directing their fun.

She got to her feet and helped Mike to rise, not as easy as it might sound with his cock so big and stiff. "Let's go to the bedroom," she invited him. Without waiting for an answer, she headed for the dimly lit doorway across the room. Mike eagerly followed.

The bed was turned down, as Chris had been expecting him and had been hoping he would join her there. She handed him a condom from the nightstand and when Mike opened it, he was surprised to see it was one of the pre-lubricated kind. He had no objection to using a condom, and strongly believed in safe sex, but he thought Chris's pussy would have been wet enough to not need additional lubrication.

Standing with her back to Mike, she unzipped her skirt and dropped it to the floor. Her silky panties quickly followed and Mike gazed on her ass in all its splendid nakedness. It was truly a thing of beauty, flaring out on the sides and tapering into her thighs. Her succulent cheeks were creamy white, especially inside her inviting cleft, and they curved sensuously out from the small of her back and around and back under to meet her legs. Their loveliness made his hands long to fondle and caress and even kiss them.

There was no reason to deny that desire and Chris's ass felt as marvelous as it looked, with skin that was soft and silky and absolutely smooth. "Chris, you are an amazingly beautiful woman, and your ass is gorgeous."

"I'm glad you like it Mike because it's all yours." Chris turned her face back to share another long kiss and climbed onto the bed but, instead of lying on her back and inviting him to join her, she knelt with her legs apart and reached her hands back to spread the lovely ass cheeks that had been so pleasing his eyes and hands.

Mike was confused. Obviously, even though she had spoken of her pussy, she wanted him to fuck her ass, which explained the lubricated condom. Although he would have preferred to eat and fuck her pussy, which he was sure was as beautiful as the rest of her body, he had nothing against anal sex, especially with an ass as perfect as the one waiting for him. After putting on the condom, he got on the bed behind her.

The room was dimly lit but his eyes had adjusted to the light by then and, when he looked more closely between Chris's legs, she appeared to have balls hanging there. Puzzled, he moved around to the side of the bed and saw she also had a small, erect cock jutting out.

"Chris!" he blurted out. "You've got a cock." Immediately after saying that, Mike felt like the most stupid oaf in the world for telling her something she obviously was already completely aware of.

"Of course. I'm a TS. A transsexual. Didn't Monica tell you?"

"Er, no. Ah, I guess she forgot." Mentally, Mike was cursing Monica. It was a dirty trick to play on him, but he could handle it. However, it was a truly vicious thing to do to a sweet, vulnerable woman like Chris. As his thoughts railed against Monica, he realized that, even though she had balls and a cock, he was still thinking, quite affectionately and protectively, of her as a woman, and a very beautiful woman at that.

While Mike was hesitating and wondering about his next move, she got off her knees to sit on the side of the bed and started crying. "I didn't mean to lead you on, Mike. I thought you knew. I take hormones and they gave me these nice boobies and a woman's ass but they can't do anything about my dick."

Mike remembered reading about a young TS named Gwen. Although biologically a male and given a masculine name at birth, she realized quite young that she was a woman stuck in a man's body. Gwen had lived her life as a woman until four thugs took offense and tortured her for hours before murdering her. Mike had thought of those men as being unusually despicable to do such a senseless and brutal thing, but he suddenly realized he had been thinking of doing something of the sort himself. Until then, he had considered turning his back on Chris and walking out. Although he would never do anything to hurt her physically, such a rejection would have been highly traumatic, especially coming from somebody she had trusted and had been reaching out to.

Mike sat next to Chris and put his arm gently around her shoulders, noticing how soft and feminine they were. She stopped crying and, when he pulled her to his chest, she snuggled her head against him, still sniffing. Impulsively, Mike put his hand on her chin, turned her beautiful face to his and kissed the tears off her cheeks and from her eyes and continued kissing her face until his lips were on her mouth again. To him, Chris was not only gorgeous, but a very desirable woman too. A few minutes earlier, he had been thinking of her as one of the most beautiful women he had ever met, and nothing about her had changed since then. That was when he fully realized that gender is much more than what a person's primary sex organs happen to be. Chris was a woman, and more of a woman than many of the females he had known.

"I was just surprised, but it doesn't matter. As far as I'm concerned, you are a sweet and beautiful and very sexy woman, whether you stand or sit to pee, and I really want to make love to you tonight."

"Are you just saying that?"

"Does this feel like I'm just saying it?" He gently lifted her hand and placed it on his cock, which had hardly softened following his discovery. It actually became even stiffer when enfolded in her soft, very feminine fingers. Chris stroked it briefly, again admiring the size and hardness.

"You know, we came in here to do something," he continued. "Something that we'll both really enjoy a lot. I hope you're not going to change your mind, just because I'm such a doofus."

"You're really sweet, and you're not a doofus." Chris got on her knees in the middle of the bed again and reached back to spread her ass cheeks. "There's a tube of Aquaglide on the nightstand. You're so big; I think we'll need it." Mike smiled and picked up the lubricant and a clean towel that had been left next to it, before kneeling on the bed behind her spread legs.

He admired Chris's ass again as he put the tip of the tube just inside and squeezed in a big dollop. "Ooooo," she thrilled as she felt its coolness spreading inside her. "That feels good already. I'm really horny, especially for you."

Mike was horny too, with such a beautiful ass waiting for him but he took his time preparing her. "With most women, their pussies produce enough lubrication, but yours doesn't so we have to add some and spread it around." As he was speaking, he gently pushed his finger inside her ass, or her pussy, whatever they were going to call it, and rotated it to spread the Aquaglide. With the inside ready, he added a thick coat outside, all around the rim, and covered his cock as well. They were both ready for what they hoped and believed would be some great fucking.

While Chris was on her knees, she arched her back, presenting her ass to the man she would be doing the great fucking with. Her face was pressed into one pillow and there were three more under her body because sometimes she liked to hug them while in the throes of passion. Both hands were reaching back, spreading her ass cheeks to help him make the initial penetration, always the most difficult. Mike knew that too so he reached into her pink rosebud to gently pry open the sides and create a small hole. With the fingers of one hand maintaining the opening, his other hand guided his cock until its head was pressed against the adorable target, and moved it around until the tip was actually inside.

"That's the place, Mike," Chris urged him. "Stick your big dick in my pussy."

That was his intention and he gave a strong push forward. The head of his cock wedged into the well-lubricated hole where she had been asking for it.

"Oooo! Yeah, like that! Now give it to me! Give it to me good."

Chris's ass was tight but Mike knew that, once he had gotten his cock started into her, he would be able to get its entire length inside, making it the most pleasurable for both of them. It would take a while, until the lubricant had completely liquefied and spread all along the channel he would be fucking, but he was in no hurry and he didn't believe she was either. Before going any further, he ran the tips of his fingers around his cock to be sure there were no loose flaps of skin or anything else that might cause a problem. There were none so he thrust forward, driving an inch of his shaft into her ass. Once again, she voiced her pleasure and encouraged him to continue.

Before doing as she wanted, he removed his fingers from where they had been holding her open because they were no longer needed. He wiped off the excessive lubricant with the towel that had been on the nightstand. Placing his hands on Chris's hips for leverage, he once again admired the creamy white cleft of her ass, noting how she was squirming from her desire for more of his cock. Not wanting her to wait any longer than necessary, and truly enjoying himself also, he drove more of what she wanted into her ass.

"Oh, God, Mike! Keep going! You're on my clit and it's great." For a moment he hesitated, wondering about that, until he realized that the prostate gland is sometimes described as being the male equivalent of a clit, so she meant that his cock was starting to massage that very sensitive spot, intensifying her pleasure. Once more he thrust forward, driving his cock in deeper. Chris's responses were louder moans of pleasure and more frenetic movements of her ass. Her hips were already swiveling, driving her knees like pistons into the mattress, making everything even better for both of them.

Moving slowly, he drew his cock back until just was the head was still inside her, paused and drove it back in, even farther than it had been. "Yes! Yes!" she urged him, her whole body writhing in front of him. "Really give it to me! Put your big dick all the way in my hot pussy!"

Mike did really give it to her, driving his cock in and out until it was going all the way inside what he was by then thinking of as her pussy. With every thrust into Chris, he felt his thighs pressing against her lovely white buttocks and against the fingers that were still holding them spread.

Chris was ecstatic. Mike's big cock in her pussy was just what she had been yearning for. There was no longer any need to hold herself open and she let go so she could support her upper body on her forearms. From this position, she was able to push back to meet the thrusts of this sweet and wonderful man who was giving her what she so badly needed. The next time she felt his cock surging into her pussy, indescribable delights radiating throughout her body from its path, she pushed back to meet him. Although it would have been hard for her to believe, her bliss actually increased when she reacted like that, instead of passively being fucked.

The incredible pleasure Mike was getting was hard for him to believe also. Chris's love tunnel was one of the best places his cock had ever been, better than most of the young and inexperienced pussies it had known. Although she was tight, the Aquaglide had fully liquefied and was doing a perfect job of lubricating; there was no friction at all. As his shaft glided through the tight opening, he could feel her caressing him there. While his cock plunged deeper into her, the walls it was massaging alternated squeezing and releasing him, sending waves of bliss reverberating through his body.

He could feel himself building toward the ultimate ecstasy, but it got even better. Until then, he had been simply plowing his cock into her but Mike decided to let his sexy partner take most of the initiative. Instead of thrusting forward, he remained stationary, letting Chris fuck back against him, impaling herself on his cock. His only movement was, just before she stopped, he drove forward, until her cheeks were squashed against his thighs and his balls brushed against hers. Their combined movements allowed the absolute maximum penetration eliciting ecstatic moans from both of them.

12
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