The Meeting

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Divorce leads to a Crossdresser' Dream.
6.8k words
4.65
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Part 1 of the 3 part series

Updated 10/11/2022
Created 04/20/2006
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Special thanks to Angle_Love; without her hard work and encouraging words this story would have never been posted. Thank you Angle.

He could not believe that he was finally going to see her after all these years. Since his divorce, she had been all he could think of. He fantasized every day how it would be to see her again, make love to her again, and now the day had finally arrived. He could barely sit still.

He had decided that he would greet her at the door, dressed in his new leather micro mini skirt and his new leather corset. She knew that he liked to dress as a woman, but he did not know if she would still accept him the way she did in the past.

The fact that he was a transvestite had finally destroyed his marriage. He had been able to hide the fact from his wife for nearly 15 years, but, his urge to dress up had finally become too great for him to hide any longer. He told his wife.

He was nervous. His hands were shaking as he lit yet another cigarette.

When he did, you would have though that he had told her that he had been cheating on her; she went crazy. Six months later they were sitting across from each other in her lawyer's office signing the divorce papers. Nearly 15 years down the tubes because she refused to listen or try to understand him.

She would be here any minute.

His friends, most of them, had stood by him during the divorce; some even knowing the reason his wife had left him. It was one of his friends that had told him that they had seen her in the local grocery store, putting the first thought in his mind of getting back together with her. As he searched for information about her and how to get in contact with her, he discovered that she to had recently divorced and was now living in the same town.

His heart jumped as he watched her pull into the driveway.

He had been able to get her number from a person he knew at the phone company, her number was unlisted, and had worked up the courage to call her a few weeks after his divorce had been finalized. By that time he was dressing as a woman nearly every day after work and all day on the weekends. In a short amount of time he had purchased an extensive collection of clothes for himself, along with make-up, perfume and his new pride, a long light brown curly wig, made of real human hair. The wig had cost him nearly a month's pay, but when he first put it on, the way he looked and the way it made him feel about himself, made the cost seem trivial.

As she stepped out of her car, his heart was in his throat, and he was finding it hard to swallow.

In the two weeks since he had first contacted her by phone, it had taken this long to get together because of their work schedules. She had just started a new job, and he was in the middle of his work's busiest time, so it made it very difficult for them to find a time they were both free to meet. Between now and the time of his first phone call to her, he had been very busy.

He practiced every day on applying his make up so that he looked as much like a woman as possible. He had been shopping countless times, buying outfit after outfit, not being able to make up his mind how he wanted to dress for their first meeting in years. He had also finally done something he had been thinking of doing since his wife had first moved out; he had laser hair removal done, leaving his body hairless and smooth. The only hair he had left was on the top of his head and his eye brows. Everything else he had removed, including his facial hair, freeing him from the task of daily shaving.

As he watched her walk to the door, he was finding it very difficult to breathe. What would she do when she saw him? Would she at least come in and talk to him, or would she turn and leave?

The day of the meeting had finally arrived and he had spent the night before tossing and turning, unable to sleep, wondering if he was making the right decision to meet her dressed as a woman. Unable to sleep he had gotten up and paced the house, agonizing over what to do. Finally, as the nighttime sky was lightening toward morning, he made up his mind that he was doing the right thing by letting her know from the start how he was. Once he had made up his mind, he was able to relax a bit before he had to start getting ready for their meeting. While he had been pacing, he had also decided what he was going to wear for their meeting. He had bought every type of outfit imaginable, from the most conservative to the sluttiest he could find. And since he really wanted nothing more than to make love to her again, he decided he was going to go for broke and dress like a slut. He was taking a chance by dressing for their first meeting, he might as well make it a really big chance.

As she knocked on the front door, he was unable to move, his legs felt like Jell-O and his feet would not move.

It had taken him nearly three hours to get himself ready. He had applied and then washed and then reapplied then washed his make up on and off so many times, his face felt raw, but when he had finally gotten it to were he liked it, he had to say it looked perfect. Once he placed his wig on and pulled on his outfit, his newly purchased black leather micro mini skirt and black leather corset, a pair of the deepest black stockings, his favorite pair of high heeled black mid-calf boots, and a black leather thong, that was specially designed to hide his male body parts, he felt beautiful.

By the time she knocked the second time, he had worked up the courage to open the door. As he pulled the door open and got his first good look at her in nearly 10 years, his penis began to harden and push painfully against the leather of his thong. She was still as gorgeous as ever. Her long dark curly hair cascading down to her shoulders, her deep dark brown eyes, and her sleek slim body, all was too much for him, he found as he stared at her, he could not speak.

When she laid eyes on him, she knew it was him underneath the make up and clothing, and she found herself as sexually excited by it now as she had when he had first dressed up for her. As she stood staring at him, her juices dampening her lace panties, waiting for him to invite her in, she began to envision them making love, wildly. Realizing that he was not either going to ask her in or could not, she made the first move. Stepping forward, right into his leather-covered body, she pushed him back, as she stood on her tippy toes and kissed him full on the lips, smearing their lipstick together as her tongue explored his mouth.

As she pressed her body against his, he could not help but to step back, letting her into the house. As she pressed her lips against his, he let the door close behind her, moving his arm to embrace her. As she pushed her tongue passed his slick red lips, gently parting them, he placed his other arm around her body, pulling her as tight as possible against his body; savoring the feel of her against him.

"Hi," she said as she broke their kiss, stepping back out of his embrace.

His heart still pounding hard in his chest, his whole body tingling from her kiss, he still could not find the ability to speak but one chocked word. " Hi."

"You look wonderful. I had a feeling that just maybe you would be dressed for our meeting." As she spoke, she walked across the room, taking a seat on the large overstuffed couch along the far wall. " As a matter of fact, I was hoping you would be dressed up."

"I, um . . . It's the reason..." He still could not get control over his body to communicate, as he sat down next to her on the couch.

As he sat down, he realized that he had wanted to offer her a drink before sitting, "Can I get you something to drink?" He rose quickly, moving toward the dinning room and the bar as he spoke.

"Yes, please. A single malt scotch if you have it." She watched him as he crossed the room, the way his body moved. He still moved mostly like a man, but something about the way he moved and the short skirt he was wearing, turned her on even more.

As he crossed into the other room, he found that her simple request for his favorite drink, and the fact he could feel her eyes following him as he walked, began to relax him; she seamed to fully accept him the way he was dressed.

"I have to admit that I was a little scared to greet you dressed the way I am, but I needed to get everything out in the open with you from the start." He poured them both a drink and walked back into the other room. "I mean, the fact that I am a transvestite caused me my marriage, I certainly wasn't going to hide it from you, start something with you, and then lose you." He handed her drink to her and sat down next to her.

As he lifted his glass to his red shiny lips, he could smell her, a musky scent that he remembered so very well, making his already hardened member swell larger, forcing him to squirm as he sat trying to ease the pain he was feeling.

"I am not going to pull any punches Bobby, I am hoping this meeting will be the beginning of our relationship that we left so long ago." She never once took her eyes from his face as she spoke. "I have to admit I had heard rumors about your divorce, and the reasons behind it and was more then ready to see you dress as a woman again." She took a sip of her drink. "Though I must admit to you that now compared to the first time you dressed for me, you look much better, more like a woman." Lifting her glass once again, she drained it.

As she, rose to refill her own glass, he noticed for the first time since she had arrived what she was wearing. Her ever shapely legs were covered by the same shade of black nylon he was wearing, and she too had a pair of black calf boots on, but her heels were much lower than his. A black spandex mini skirt that traveled up her body tightly covered her still perfect ass; its waistband ending half way up her stomach. Her ample breasts were covered by a short sleeve white spandex half shirt that was so tight he could tell she was not wearing a bra underneath. Her hard erect nipples were pushing against the tight fabric.

"Beth I cannot tell you how happy I am to hear you say that." He drained his drink and crossed the room to join her.

As he neared her, she set her drink down on the small service bar, pulled up her skirt, revealing her white lace panties and black garter belt underneath, and stepped in front of him. "Take me now Bobby. Make love to me the way we use to." She pushed her body hard against his, grinding herself against him.

He could feel the heat from her body through the leather of his corset as he reached his hands behind her taking hold of her firm round ass. Pulling her tighter against him, he lifted her. Then as carefully as he could, he knelt down, laying her on the floor as he came to rest on top of her hot firm body. As he laid himself across her, he kissed her deeply, smearing his lipstick with hers as their tongues danced together.

As he kissed her, massaging her ample firm breasts through the glossy smooth fabric of her top, she reached her hands down his back, grabbing the hem of his skirt, lifting it to his waist, so she could massage his ass.

"Take me now." She pushed him off her, and turned herself until she was on her hands and knees in front of him. "Take me now. Take me from behind."

The sweet musky smell of her, her ass just inches from his face, were all too much for him to exercise any further thought of control. As quickly as he could, he stripped his leather thong from his body, freeing his hard long hot member. Taking himself in one hand, he placed his other on the small of her back, preparing to enter her hot steaming hole, the memory of which was still fresh in his mind after all the years.

As she sensed him nearing her with his throbbing manhood, she allowed her head to drop to the floor, raising her sweet wet flower closer to him and the same time freeing her hands to reach down between her legs and rip her panties from around her waist, exposing to him her cleanly shaved swollen pussy. Throwing her now shredded panties aside, she trusted herself backwards into him. Feeling the large bulbous head of his thick hot member touch her wet moist lips for the first time in years, she drove herself back even harder, until she had forced the thick round head of him into her.

With the tip of his dick buried in her steaming hot pussy, he held himself there, once again enjoying the feeling of her. Then without warning, he drove himself deep into her with one long strong stroke, nearly pushing her flat onto the floor.

"Yes!" she screamed at the top of her lungs as he began to push himself in and out of her now dripping hot pussy. The faster and harder he drove into her, the harder she pushed herself backwards against him, driving his long thick member into herself as far as he could go.

"Faster. Faster!!" she screamed as he felt the slick smooth walls of her pussy tighten and contract, as she began to orgasm.

No longer able to control her body, she began to buck wildly, driving his dick deeper and deeper into her, as she came. He had always been able to make her cum, and the years they had been apart had not changed a thing. She was now screaming uncontrollably as she came again. It was in the midst of her second orgasm, she felt his body tense behind her, as he grabbed her hips hard and began to fill her with his hot thick liquid. As the first spray of his heavy boiling fluid touched her deep within, she began to cum for a third time, driving his pulsing dick deep into her throbbing burning pussy.

As both of their orgasms began to subside, and they were able to catch their breaths, they knelt where they were, still locked together on the floor.

"I want to do something for you my dear," she purred, turning to look at him over her shoulder. "I want to do something I have never done for anyone before." She moved forward as she spoke, forcing his now shrinking member to slip out of her still hot pussy, causing him to let a sigh escape from his lips. "I need you to lie down on your back where you are, my sexy little girl." She was still looking at him over her shoulder.

As he moved to do as she asked, he could not think of what she had in mind as he laid himself down on the floor. The whole time he was moving, all he could think of was how good it felt to make love to her again and how much he liked having her talk to him like he was a woman. Once he was flat on his back, she began to move herself backwards until her hot sweet pussy was over his face and her face was over his limb cock. Without saying a word, she bent her head down, gently sucking him deep into her mouth as she twirled her tongue over his sensitive head. She was driving him crazy. No one he had ever had sex with was ever willing to suck him after he had made love to her, and the experience was fantastic.

As she continued to suck and lick his now growing member, he thought it would be only fair for him to do the same to her. Looking up at her hairless pussy, just inches above his head, he could see his own thick fluid beginning to drip out of her, covering her swollen moist lips. Trying not to think about what he was about to do, he lifted himself up slightly and licked her red-hot lips, tasting himself for the first time. As the taste of her sweet juices mixed with his, own hot cum, touched his tongue, he found that it was not a bad taste; instead, he found it to be a taste he could enjoy. Now that he had discovered he liked the taste of their combined cum, he began to lick and clean her pussy in earnest.

As she felt his tongue touch her still swollen lips, she felt her body quiver, both from his hot tongue and the thought of him eating his own cum out of her. She had tasted the combination of them first, as she had sucked his limp member into her mouth, and knew how good it tasted to her. As he discovered this and drove his face deeper into her, searching for more, she sucked on him harder. The farther he drove his hot tongue into her, the harder she sucked on him, as he now began to grow in her mouth. His tongue buried deep into her, his chin pushing against her swelling clitoris, she could no longer hold herself up on her hands and knees.

Wanting him to continue to eat her, wanting his dancing tongue as deep into her as she could get it, she pushed herself backward until she was resting her pulsing pussy on his face, grinding her hard little clitoris against his chin. It was not long, with his tongue dancing deep in her steaming pussy; she was cumming again, covering his face with her own hot juices. Not wanting him to stop, but wanting to please him as he was pleasing her, she lifted herself off his face, turning herself until her dripping wet pussy was poised over his hard stiff cock. Taking his thick member in hand, she guided it slowly into her, releasing him as she drove him deep into her hot moist hole.

"Don't move baby, I'm going to do you like you've never been done before," she told him as she began to slowly rotate her hips in a circular motion. As she continued to rotate her hips on his stiff long shaft, she began to also lift herself up and down, pulling him in and out of her hot moist pussy. She could tell by the look on his face. He was enjoying what she was doing to him.

As she moved herself faster and faster on his stiff hard member, she drew them both closer to the edge of ecstasy. As he was about to cum his breathing hard and deep with the look of pure pleasure on his face, she lifted her body off his, turned and took his cock deep into her mouth. It was not long until he was filling her mouth with his sweet hot liquid, splashing against the back of her throat.

"That was great my little slut," Beth said as she released his shrinking cock for her mouth, turning to lay her head and body against his hot leather-covered body. "I didn't know I could still cum like that."

"I'm glad to know that I can still make you cum like that," he told her as he caressed her hair. "I was so afraid, at first, that you would not want me the way I am, and then I was afraid that I wouldn't be able to please you..."

"Shhh..." She held her finger against his lips to stop him from going on. "Bobby I think you and I have just started something very unique. Having you dressed as a woman, does something to me deep down inside. I'm not sure what yet, but I do know that it made me so very horny that when we were making love, I was cuming as soon as you pushed the head of your thick hard cock passed my hot wet lips."

As she spoke, she could feel herself getting wet again, just thinking of him making love to her again. "I need you again. I want you again." Her one hand was between his legs, gently stroking his soft limb cock, as her other was between her legs, spreading her hot juices over her swollen lips as she played with herself. "I want my girlfriend to make love to me again."

As she breathed the last into his ear, he could feel himself growing in her hand. The combination of how she was treating him, calling him her girlfriend, and her gentle massaging of his cock, along with the fact she was playing with herself, was arousing him once again. His cock now swollen once again to its full length and thickness in her hand, he was ready to take her again. Pushing her hand aside, he began to rise, gently moving her off his leather clad body, pushing her to the floor.

"Now wait," she stopped him, sitting herself up next to him. Removing her own hand from between her legs, she placed her nectar-covered fingers against his lips as she continued to speak. "I have an idea, no a fantasy, I would like to know if you want to help me live out." As she spoke, she pushed her fingers deep into his mouth, letting him hungrily clean them of her sweet cum.

"Yes Beth, whatever you want, I want to give it to you," he told her as she removed her fingers from his hungry mouth. "Whatever fantasy you may have, I will do the best I can to make it come true."

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