Doug was planning a little trip with a few bits and pieces his wife knew nothing about. You see, she was heading to the East Coast for a combination of business meetings and visiting some of her family that lived there. While she was gone Doug was planning a trip to Chicago to see a football game. This wasn’t the first time they planned separate trips like this, although most were over the summer and he would go to various baseball parks. But this time he was planning something different. Oh, he would go to the football game and see his Packers play the Bears. Every word he told his wife was the absolute truth.

He already made a hotel reservation near the stadium for two nights. He planned his route for his nine-hour drive into Chicago. What he forgot to mention was that he was leaving very early so he could have extra time in Chicago. The game was an early one, so he could leave immediately after and unless the weather held him up, he would be home several days before her without needing another night in a hotel. Leaving early gave him Friday night, all day Saturday, and even Saturday night to try something very, very different. It was something he had been curious about for several years but never dared to act on it. As a birthday gift to himself, he decided it was time.

He made all the arrangements, got pre-screened, and even spent several hours in contact and everything seemed on the up-and-up. He was meeting an escort for Friday night, not just any escort, but a beautiful one named Jasmine. He was very nervous, but she seemed well acquainted with first-timers, what she had called ‘virgins’. He tried to do his homework, researched very carefully, read multiple reviews, and even contacted a couple of agencies specializing in his interest. It all boiled down to a lovely escort who came highly recommended. When he finally made direct contact, she was very open and honest and coaxed more information out of him than he probably realized, but it also reassured him he was dealing with a professional. So he pressed ahead with his plans, set aside the funds, and finally put his wife on a plane heading east. Very early the next morning, well before the sun came up, he was on the road to Chicago.

The hotel was a nice one and once checked in, he called Jasmine and confirmed their meeting in the hotel bar for five that evening. He prepped himself very carefully, as she had instructed him, and waited less-than-patiently for the appointed time. He was early to the hotel bar and was sipping one weak scotch as a fortifier when he spotted Jasmine making her entrance. Heads turned as she came in, she was, in a word, stunning. Her profile said she was twenty-five, five-foot seven-inches tall, and 140 lbs, with long dark hair. The pictures on her website did not do her justice.

She was in an off-white dress, snug, but not form-fitting. It was sleeveless and open under her arms. As she turned to go past a table, he saw a jasmine flower tattoo on her side, under one arm. It was her only ink and it suited her perfectly. As she moved toward him, she had a small smile telling him she knew exactly the impact she was having on everyone who saw her. Halfway across the room, she spotted him and her face lit up, making her even more beautiful.

She came across the room smoothly right toward him. He had sent her several pictures once he was satisfied and the two were communicating fairly regularly. She was so much more than he expected. He got up as she approached. One of her requirements was to be a gentleman. She held her hand out and rather than introducing herself to him, she leaned in and kissed his cheek and said: “Hello, darling!”

He blushed more than he realized. She was the consummate actress while he was a rank tyro. He arranged for something called the ‘GFE’ or Girl Friend Experience, and it was started now. The two had a pleasant, but light dinner, making casual conversation and Jasmine could see the tension slowly leave Doug as the evening went on. By seven some of his nervousness returned as they entered the elevator to go to his room. He held her around the waist and she leaned against him giving the picture of a loving couple.

Anyone looking at them would see exactly what Doug was paying for, they looked like a perfect couple. Doug was slim and only a little taller than Jasmine, even in her low heels. He was a little older than she was, in good shape, a long-distance runner more than a gym rat. They made a striking couple and could see themselves in the inside reflective surface of the elevator doors.

She turned a face up to him and pulled his face down for a kiss. She knew the elevators had security, the kiss was the finishing touch showing anyone who might be watching at any time that they were nothing more than a couple. Doug returned the kiss with almost surprisingly, at least to himself. Jasmine was the first woman he kissed with more than a touch of the lips since he got married. Something perfectly right about her as she leaned against him caught him off-guard, but he knew he liked everything that had happened so far. The rest of the night would be a night with a lot of firsts, but he was looking forward to it.

Once in the hotel room, Jasmine paused. “I know this sort of ruins the mood, but we have some business to settle first. Once we get that out of the way, we can enjoy ourselves.”

Doug reached into his overnight bag and retrieved an envelope. He handed it to her and she took a quick look and put it in her purse. “One last thing?”

Accepting the money was close to being grounds for an arrest in Chicago, but to make sure he wasn’t a cop, there was one more step to confirm. She was sure he wasn’t, everything she did for pre-screening checked out and she rarely made a mistake. Doug stripped off all his clothes. While it felt like an urban police legend, a cop would never strip down. He wasn’t wired, he had no weapon, well maybe except for the one slowly growing between his legs. It was starting to excite him to be naked in front of her.

In return, she dropped her dress and stood before him in lingerie, just a bra, panties, and stockings. She was so beautiful it took his breath away.

Jasmine smiled and stepped against him, kissing him with more passion than she had in the elevator. His arms came up and felt her warm skin. She led him to the bed and sat on the edge. She opened her legs wide and bade him kneel. She smiled at him, which reduced the sudden tension she knew he was feeling. She waited patiently, knowing he needed to make this move himself.

He paused, but not for long, he had not just planned this but anticipated it, He bent down slightly and kissed the inside of her knee, working slowly along her thigh. Her thigh was warm and lightly scented. His kisses and licks left a slight wet trail. On the other thigh, he slid his hand along it, marveling at the smooth texture of her stocking. At the top of her thigh, he paused one last time, then tasted her skin directly and looked at her panties, nervous and excited by what lay within. He rubbed his hand across it and felt her contours. To prolong it more out of enjoyment than concern, he pressed his face to it and felt her start to respond.

She didn’t make any moves yet, she understood exactly what was going through Doug’s mind and knew this was more a voyage of discovery than anything else. She would fulfill all his wishes before the night was over and quite possibly he could fulfill many of hers tomorrow. She smiled, not a predatory smile many in her profession would exhibit, but one of feeling and a desire to ensure not only a well-satisfied customer but one satisfied in ways he may have not anticipated. Some clients made her hate her chosen profession. The majority were just pretty much non-entities. But once in a while, a client came along that made her love her job, Doug had the potential to be one!

He reached the point of no return as he pulled the leg of her panties to one side and her cock fell out. It was just starting to harden under his ministrations and he looked closely at the first penis he had ever seen from this angle or this close. It didn’t look large, well not yet. He knew her statistics were posted on her website, but those cold numbers meant little when face to — face. He touched it, felt the softness, and then cupped her testicles. He knew from his research that many transsexuals had them removed, but the private part of her website, access only granted to screened customers, said she decided to keep them so she could still generate heavier cum loads and more than the typical clear fluid. Again, he knew all that logically, but the feeling of it wasn’t something you could research or understand without the rush of holding it in his hand.

She slowly got harder, he wrapped one hand around it squeezed gently. As it got firmer, he started stroking it. The head expanded and the rubbery feel tightened up as well. His whole world revolved around her cock as his other hand cupped and rubbed her balls.

Jasmine smiled at the look of wonder on Doug’s face. She had so many different clients, but few were as genuine as Doug. Some were rougher, some just plain horny and looking for something different. She did her best to screen out the dangerous ones and usually succeeded. She looked down at Doug knowing this sort of client didn’t come along very often. The whole idea of the GFE was to make everything seem like a date, but once in a while it actually felt like a date.

“Spit on it.”

Doug looked up, it was like he was seeing Jasmine for the first time. “Are you sure?”

She grinned. “Yes, it’ll make it slick so stroking it is easier.”

He tried, but his mouth was too dry. She leaned her head over and spit, it dripped down onto her cock. Doug didn’t hesitate but rubbed it into the head and shaft. It glistened and his hand slid faster up and down her shaft as she got harder.

She reached down and slowed his hand. Without a word she tilted it right at his face, she knew what she wanted Doug to do and it was one of the things he was very firm about wanting. There was a slight pause, not a nervous pause, just a brief instant as he thought something. But he leaned in and took her in his mouth.

Doug was surprised at how descriptions he had read online were so different than actually doing it. He had Jasmine’s cock head in his mouth. It was so warm and felt so smooth and soft. He knew it was hard, but it didn’t feel like a steel bar in his mouth. He sucked the tip, it felt like a soft rubber ball. All that was secondary because he heard Jasmine inhale sharply. The sound was so encouraging that he sucked her cock in as far as he could. He kept sucking her, and when he started bobbing his head up and down, she stopped him gently.

“I don’t want to cum yet and if you keep that up, I will.” She said with a gentle smile. She then pulled him up on the bed alongside her. He lay on top of her and she rolled them over until she was on top. Their cocks against each other as she kissed him. His hands stroked her body as she arched her back up and she very lightly let their cocks rub together. She put her hands on his chest and simply kept up the stimulation, but not enough for either of them to orgasm. It wasn’t time yet.

She slid down and took his cock in her mouth, holding it more than sucking it. She knew how close he was and wanted to prolong it. She didn’t just want an orgasm, she wanted an explosion. She licked his balls for a minute and then pushed him enough for him to roll over. She felt the tension return to his body as she placed a kiss on the small of his back. She knew this well and felt her own cock respond to the idea of taking another virgin ass. She reached for her clutch and retrieved a small bottle of lube. She tucked it between her legs to warm it up as she worked her way down his ass, licking and spitting a bit, getting him used to her being there. When she felt him grind against the bed, she lightened up and then took a pillow and pushed it under him. It was large enough his cock hung with just the tip against the bed. She knew he might cum, but hoped she could just hold him on the edge until he was desperate for an orgasm.

She poured a little of the lube at the top of his ass and he could feel it flow down. She rubbed his rosebud, not penetrating, just making it very well lubricated. She also rubbed the lube on his ball sack, feeling him react to everything in a positive way. He was so close and she knew it. Without him noticing, she retrieved one more thing from her clutch and put the condom on. A little lube on it as well and when she felt him pushing back toward her, she knew it was time for another part of his fantasy.

As her cock touched his ass, she felt him tighten up, as expected. She rubbed her cock along his ass, letting the lube keep things slick and not pressing hard.

“It’s okay baby, but you have to relax a bit. You know my cock isn’t big enough to hurt you, but you still need to relax or it can be uncomfortable.”

She kept up quiet words and slowly felt him loosen up. She knew what he was thinking, but she was an expert at this. She almost giggled at her own thoughts and almost quoted a favorite movie and said: “Don’t worry, I’m a professional!” But she knew it wasn’t time for humor. She would remember to mention it later when they were cuddling.

She ran a hand down his butt and rubbed across his bud again, this time he tensed up for just a second and she felt him force himself to relax. She pushed a fingertip in and then out several times until she knew he was calm and even anticipating things in a good way. A little deeper and she opened him up with a second finger. She kept one hand on the small of his back as a reminder for him to stay in that position and also for her leverage. She pulled her two fingers out and saw the clear lube and knew he had prepped himself well. She was really starting to like Doug more and more.

After slowly fucking his ass with her fingers for a while, it was time. She pulled her fingers out and quickly put her cock to his entrance. He didn’t even have time to think that things had changed when she slowly pushed into his ass. He might not have even realized it wasn’t her fingers until she laid her body on his and he felt her hands on his hips.

“That’s right lover, I am all the way inside you. You wanted this and now you have my whole cock in you. You are so tight. Squeeze me.”

She felt him tighten his muscles and when she felt it, she pulled out and sank back in. She heard him make a noise, maybe a grunt, so she did it again.

“How does that feel, baby?”

“Jasmine, it’s incredible.” She could hear the amazement in his voice.

She stroked his ass again and felt him squeezing as she pushed in and relaxing as she pulled out. They kept going for several minutes until she felt him really starting to push back towards her, a sure sign of an upcoming orgasm.

She pulled all the way out. “Turn over, baby. I want to see your face when you cum from my cock.”

He turned over and kept the pillow under his hips. She looked him right in the eye as she fed her cock back into his ass. As she did he closed his eyes briefly. She paused until he opened them again. Then she started fucking him, pausing anytime he held his eyes closed. She loved the look on his face, both the wonder at the feelings and the tightness as she felt his orgasm approaching.

She moved faster, and he responded. He was grunting in time with her thrusts and she felt his orgasm start. He had been very turned on for over half an hour. His cock never wavered in all that time and when he came it was with a loud cry and she saw his cum shoot past his face and land near the top of the bed. His body stiffened, his back arched, his eyes squeezed shut as his cock shot several more times. Some landed on the pillow above his head and some on his chest. She didn’t know if it was the normal amount for him, but it was time to add to it. When his body relaxed, she pulled out and stripped off the condom. She straddled his legs and jerked her cock. It didn’t take her very long and she was glad to see awareness return to his eyes as he saw her cum on his chest and belly.

She grunted some herself as her cum mixed with his. When she was done, she saw him touch his chest, feeling their cum. She wasn’t totally sure what he was thinking, but he wasn’t reacting negatively, as a few of her clients had. It was more a sense of wonder than anything else. She rose and got a small towel and started cleaning his chest off. He stopped her hand for a moment.

“Can I taste it?”

“If you want.” Normally she would have said no, but she knew she was clean and healthy. She got tested often to make damn sure. She was very confident he was as well. She would have been surprised if he had sex with anyone other than his wife since he got married.

She watched him scoop some with a finger and lick it tentatively. He cleaned off the finger but didn’t go back for more as she cleaned him up.

She smiled at him, “How was it?”

“Not what I expected, sweeter bit a little astringent,” he said thoughtfully.

“Well, if you do this again, you’ll find everyone tastes different.”

“I don’t think I’ll be doing this again.”

She looked at him seriously. “Don’t say that. I know you’ll be going home and resuming your life. But you did something here that most people either never think about or only dream of. You never know what the future may bring. Don’t close yourself off to the possibilities.”

He thought about it as she took the towel back to the bathroom. She debated something and then simply returned to the bed and pulled the top sheet down and covered him before slipping next to him.

“May I spend the night with you?”

He didn’t say anything and wrapped his arms around her. She knew this was more than a little dangerous for her, but she was really starting to like Doug and seriously considered what she was going to ask him to do tomorrow. She was not sure he would be up for it but thought he just might be. The anticipation of that made her heart race faster and she felt him turn off the light and they fit well together before drifting to sleep.

Doug slept surprisingly well. He wasn’t sure he would, but once Jasmine snuggled up against him, it felt like the most natural thing in the world. During the night Jasmine had turned away and Doug rolled with her and woke pressed against her back. He felt his ‘morning wood’ pressed against her ass but didn’t want to move, even though his bladder was what woke him up. He also didn’t realize Jasmine was awake and simply liked the feel of his hard cock against her.

When she realized Doug was awake, she pushed against him in a stretch, grinding her ass against him. She felt his hand on her hip pulling her even tighter. She thought for a minute about what she had planned and decided to put off the asking for a little morning fun. It had been a while since she woke up with a handsome man who she actually liked.

With one hand she reached to the nightstand where she kept her clutch, retrieving a small foil pack and turning to face Doug. She reached down and held his cock, enjoying the hardness. She didn’t say anything but showed him the condom. He looked hesitant and glanced toward the hotel room’s bathroom. She smiled and nodded, getting up with him.

He was surprised when she went into the bathroom with him, his cock leading the way. When they got in there, she held him and aimed him at the toilet. He was hard, so it actually took a while. It was another new experience. Once done, she cleaned his tip with a square of tissue and stood in his place. She liked that he was quick on the uptake as he held her while she took care of business. He also cleaned her.

They both went to the single vanity and sink to brush their teeth and the two of them started jostling for position in front of the mirror. It was playful and they kept sliding their bodies against each other. By the time they were finished, they were both hard and very turned on. Without a word, they went back to bed.

She laid him on his back and unwrapped the condom and spoke for the first time. “Normally I would do this with my mouth, but this is a lubricated condom, and to be honest, I hate the taste. The first time I tried that, it was really awful.” She made a face that had Doug laughing. She unrolled the condom on him, the reservoir tip flopped over, which always made her smile. She stroked his cock a few times, then straddled him.

He watched with very little expression as she took his cock, pointed it straight up, and settled down on him. When she felt him touch her, she aligned it carefully, and, moving very slowly, she felt his cock pop into her, right past her sphincter. She paused there and looked down at Doug. His hands were on her thighs as his gaze was between them with his head angled so he could see her cock.

Slowly she pushed herself down until he was completely inside her. She squeezed her muscles a bit and let him adjust to the feeling. She saw his face slowly change.

“Holy fuck!”

Jasmine smiled at both the expression and the look on his face. She felt that Doug wasn’t normally one to curse, but she also knew that unless he was in the habit of fucking virgins, he had never been in anything as tight as her ass. She lifted up and sank back down. She saw his eyes close and felt him push up toward her.

She moved very slowly, relishing both the feel of him and the honest look on his face. There was no guile, no secret agenda of the many guys who secretly wanted a transsexual, but his face was almost boyish in its lack of complexity. He was simply enjoying it and after several strokes, he looked up into Jasmine’s eyes. She was smiling down at him as she slowly rode him. She pushed down and stayed there, using her muscles on him as she took her own cock in her hand and started stroking herself to hardness.

Doug didn’t say anything else, he wasn’t sure what to say or do. His cock felt like it was encased in a velvet glove, he could feel her in ways he had never felt a vagina, not even his wife the first time they had sex. He paused in thought, it was the first time in hours he had thought of his wife and then he got distracted as she rose up and down again to get his attention when she felt he was wavering mentally.

Doug caught her eye again, she was upright and looked so incredibly beautiful that her cock actually seemed incongruous. It didn’t fit the image in some ways and yet in others, it fit absolutely perfectly. He thought about last night when he tasted it and when he felt it inside of him and recalling all that combined with this morning made him close his eyes briefly as he arched his back and pushed up deeper into her.

Jasmine saw his eyes close and then open again. His look had changed, she could tell he was feeling everything and was really enjoying it. She was as well. Yes, she worked part-time as an escort and had sex with most of her clients, but she rarely enjoyed it like this. Doug was the first one she ever slept with, and by that, she meant actual sleep. She had a few clients pay for the entire night, but she never slept, never let her guard down. Doug was something new for her and she decided to enjoy it for both of them.

Her cock was hard, so she leaned down and took his hands from her thighs, and put them on her breasts. She knew they weren’t overly large and she never wanted surgery, but her breasts were sensitive and when she felt his fingers tighten on her nipples, she hissed in appreciation. Doug was starting to get into it, even the newness of this wasn’t stopping him from doing what came naturally for a man with a woman.

He wrapped his arms around her and pulled her down against him. His cock stayed inside her, just barely. Then he kissed her! They had kissed last night, and while the kisses were good, there was a nervousness that made them feel slightly awkward, even in the elevator after dinner. Any sign of that was gone. Doug was kissing her as a lover. His tongue slid into her mouth and she started sucking on it like it was a cock. She felt him slip out and reached down to put him back in. Then she sat up and took her own cock in her hand, stroking it firmly.