tagTranssexuals & CrossdressersThe Happiest of Endings

The Happiest of Endings

bybb1212©

Author's note: Due to the fact that all my other stories on this site are heterosexual I want to stress that this story is in the transsexuals and cross dressers category because it contains explicit sex between male and transsexual characters. If this content is likely to offend or upset you please stop reading now. I am happy to receive criticism on writing style, storyline etc but not because you do not personally agree with the sexuality of the characters. That said if you are still with me I hope you enjoy the story.

*

It had been a long hard day at work and the tension caused by the fast approaching project deadline was mounting. David knew he needed to relax somehow but Allie, his significant other, was also stressed from her work and neither of them had the patience to calm the other down. David sank himself in a bubble bath for almost an hour with a book but it was no good, he just couldn't calm his mind.

Eventually David discarded the book in disgust, and drained the water while wondering what to do next. While drying himself he thought of the new massage center that he had noticed located in a shop front in the next suburb. A massage would be perfect, he thought and checked his watch that he had left next to the basin. Just after 8.30, hopefully they would still be open long enough for him to get an hour massage.

David did get regular massages but the girl he went to did not work after 7.00, and so occasionally he tried other places, usually resulting in disappointment.

Massages in David's experience come in three types. There are those like his usual where it is all business and you get a very good massage but definitely nothing else, then there is the sometimes reasonable massage with the nude or semi nude masseuse and the famous "happy ending" oily hand job and the last one is the front for the illegal brothel where you get a few strokes of the contact they call a massage before you get asked if you want "extras". At the last type of place the massage is useless and usually the lady concerned is well past her prime, can barely speak English and is not at all interesting.

David went through the lounge and told Allie he was going out. She was watching one of the "CSI" shows (Allie had once asked him who did the theme song, he said "Yes" and totally confused her) and she was so absorbed that she didn't even acknowledge him.

As he started the car and reversed out onto the road David thought about the place he was going to. It was new and he didn't know a lot about it, but the massage sign was big and obvious enough to assume it was legitimate. David hoped they did a good proper massage because that was exactly what he needed.

When he had parked the car David walked up the row of closed shops to the only light still on, went through the white painted door and into a little reception area. He heard a chime out the back that announced his presence. There was a small reception counter and a curtained off doorway behind it heading to the back of the shop. The pale blue walls were three quarter height and there was light shining over the partition that was just a bit brighter than the dim bulb above his head. In the corner there were a couple of old chairs for people who wanted to wait.

David looked at the counter and on it were a cardholder with business cards showing details of the place and also a small bell. The wall had an anatomical chart with the human bodies muscles highlighted and a there was also a price list that was reassuringly short.

Full body relaxation massage half hour: $45.

Full body relaxation massage one hour: $75.

Gift certificates available.

Hours: 11.00am to 9.00pm.

David looked at his watch and it was 8.50. Just made it.

Things were looking up. From David's observation the signs here were that this was a real business and not just a whorehouse, and what he needed badly now was a relaxing massage, not a hurried and unappetizing blowjob or fuck.

David was just reaching across to ring the bell when a girl came through the curtain. She saw him and jumped.

"Sorry," she said, obviously startled, "I didn't hear the bell and I was just coming through to close up".

She was quite tall, maybe five foot eight and had legs that just went forever. The white, pointy-toed high heeled shoes that had straps that wound up past her calves over white stockings were very sexy. David had not seen that sort of shoe on a masseuse before, mostly they went for practical flat shoes. Fine, he thought, as long as she doesn't walk on my back. Mousy blonde hair fell to her shoulders in a "I've been working hard today" look that in no way made her look any less pretty, just more natural. Dressed in a short white uniform she had a little green nametag pinned to her modestly sized chest that said "Jade". David thought to himself, I like tall, willowy blondes, they are often very sensual and confident but are also sometimes not very strong when it comes to massaging, and I am a pretty big man who likes a good firm massage.

"Damn," he replied, "I could really use a massage tonight Jade."

She frowned, and then looked down at her nametag, realizing how he knew her name.

"Hang on." She said and then poked her head back out through the curtain. David was suddenly looking at a very fine round behind with a tight white skirt riding just high enough to show stocking tops.

"Julie," Jade called, "there's a guy here who wants a massage, do you mind staying behind while I do it?"

"OK sweetie." Answered a melodic, low and sexy voice.

Wow, David thought, that one could do telephone sex, just those words got me interested.

Jade turned around and caught him staring at her ass and legs. She blushed and pulled futilely at the hem of her uniform as he turned away embarrassed.

"How long do you want?" Jade asked brusquely.

"An hour if it's not a problem." David mumbled, hoping he hadn't upset her too much.

"Fine." Jade replied. "I'll just close up."

She squeezed past him leaving a waft of subtle perfume. Jade locked the door and flicked off two light switches, the first turned off the sign and the second turned off the light above David. In the semi darkness Jade grabbed his hand.

"This way." She said and led him through the curtain to a dimly lit hallway. There were three doors in the partition style walls off to the left, obviously the massage rooms, and one door straight ahead in a full wall at the end of the hall. Jade took him into the first massage room. It was reasonably dim with a low power light fitting in the roof directly above a massage table that had the hole at the top to put your head through. There were towels arranged around the head hole and on the table itself. A chair in the far corner looked like it matched the ones in the reception area and there was a shelf unit against a wall with oils, towels and a candle burning on the top shelf. A small CD player was in the other far corner playing soft relaxation music. There were poster prints on the walls of waterfalls and forests. The floor was carpeted and room was cozy and just slightly warm, just perfect for a relaxing massage.

"What's your name?" Jade asked, turning to him.

"David." he replied. He had never seen the point in making up names when he got a massage, so he always gave his real one.

"OK David that will be $75." Jade said, deep blue eyes shining and suddenly smiling again. David thought she was very pretty when she smiled.

He reached for his wallet and pulled out the notes. $75 was expensive for a real massage but the way he was he didn't care and it was too late to go anywhere else.

"Just put your clothes on the chair and lie face down on the table." Jade said, taking the money. Then she went out, closing the door behind her.

David undressed and lay down as instructed. He could hear a low murmur of voices toward the back of the shop but could not make out anything they were saying. He let the music wash over him and slowly relaxed.

The door opened and closed again and then Jade was next to him.

"You haven't been here before." She said, more a statement than a question.

"No." He said to the floor through the head hole.

"Do you want a towel for modesty while I do your back?" She asked.

"No thanks." He answered quietly.

"Do you like a hard or soft massage?" Jade asked.

"Very hard." He replied.

"Be sure to let me know if it is too hard or too soft." Jade said.

David heard the oil bottle open and then she rubbed her hands together to warm the oil. Jade started on his left calf muscle and David soon knew that she was good at this, very good indeed. She started softly, warming up the muscles before rubbing harder and harder. A couple of times she asked if it was hard enough and he just said perfect. For about half an hour she worked on his legs, back and ass and the only noises were the relaxation music, the oil bottle squirting, her hands on his skin and his quiet moans of pleasure. David liked to relax during a massage and did not like the distraction of small talk and Jade seemed to understand this, working in silence. She worked up his left leg to the buttock, where he gave a little shiver as her hand accidentally brushed the hair on his balls before she worked back down to the foot. After a good session on the foot she swapped sides to the right calf showing her professionalism by not losing contact with him during the change. She once again worked her way up and again he felt a very brief light touch to the balls, this time causing a tingling feeling in his dick. Was this accidental he wondered?

Then she was heading back down again to the right foot and this was treated to a long session too. Some people hate having their feet massaged but David loved it, and Jade was very skilled. She finished the foot and he felt her hands tracing the muscles in both of his powerful legs up to his buttocks again and this time she trailed her thumbs up the bum crack gently brushing his asshole as they passed. He jumped a bit with the guilty pleasure she caused. David enjoyed having his asshole rubbed, it is a very sensitive place, and occasionally during sex Allie would slip a finger in, something that was sure to make him cum harder than usual.

But Jade just kept heading up and started working on his back. First she worked her way up the spine to his shoulders and then back down to the base of the spine before doing the whole width of his back on her way back up again. David was in heaven as her strong, skilled hands sought out the areas of tension and worked the muscles firmly until they were gone.

He was pretty close to asleep when she worked back down to the buttocks and went to work there. As the biggest muscle in the body this one holds the most stress and Jade went to town in way that rode the fine line between ecstasy and agony. Her thumbs gouged deeply into David's buttocks as she again coaxed weeks of tension out of his muscles.

Fantastic, he thought, I haven't had a massage this good for years.

Then Jade made her first mistake. When she was pouring some more oil into the hand that was resting on David's ass a small amounted squirted past her hand right into the crack of his bum. He jumped a bit, but was still half asleep.

"Sorry," Jade said, "I will wipe that off."

"Just rub it in." He replied, only half thinking what he was saying.

Jade giggled nervously and then complied.

The side of her hand slid down his crack rubbing oil from the top down to the base of David's balls. He groaned.

Jade's hand circled at the base of his balls, rubbing the oil in, and then slowly came back up again, rubbing in small circular motions. When she rubbed his tight, puckered asshole and he groaned louder. Jade paused for a second and the rubbed the tender place again, this time a bit harder. David felt an erection starting as he groaned again.

"Do you like that?" Jade asked as she ran a finger around the rim of his ass.

"Oh yeah." David moaned as the exquisite sensation grew.

"Would you like me to keep rubbing here for a while?" She asked, teasing his now oily asshole with one hand and then he felt the other gently grabbing his balls.

"Darling," David moaned as he squirmed with pleasure, "you can do whatever you want, just don't stop."

Again he heard the little girlish giggle and Jade kept rubbing around his sensitive ring. Then he felt her finger against his opening and he lifted his ass off the massage table, causing the investigating finger to gently pop through the muscle and slip a small way into his ass. David thought the feeling was fantastic and Jade's other hand slipped down past his balls to encircle his cock, which was now almost fully erect. He didn't remember it getting that way, but right then it certainly was.

"Oooh that's nice." Jade said as she started masturbating him with one hand and slowly teasing his asshole with a finger from the other.

There David was, his ass lifted off the table, pushing himself against Jade's exploring finger, absently wondering what would happen next, when he heard the door close to the next room.

"Sweetie," came the $4.95 per minute voice across the top of the partition, "I'm bored, can I lie down in here?"

"OK Julie," Jade answered, "just don't forget I have a customer in here."

A customer in a very interesting position David thought as Jade's hand on his cock slowly squeezed from tip to base and back again while her finger in his ass swirled around, exciting the tender nerve endings in a most pleasurable way.

He was moaning softly, trying not to make enough noise to be heard next door and he felt the pressure in his balls building up. This will not take long, David thought, realizing it had been a couple of days since he had last had sex, and there was a fair bit of pressure built up.

Jade was slowly increasing speed of her hand, not enough to be trying to hasten his orgasm, David thought, but more as a deliberate preparation for a great release in a slightly longer time. His moans were louder as her finger entered his ass, circled a bit then pulled right out and ran around the rim before sliding back in. Eventually she started slipping further in until one time she brushed his prostate. David gasped with the sensation and felt his balls tense, suddenly ready to shoot as a result of this new sensation.

In the back of his mind he heard a rhythmic squeak from the next cubicle and then Julie's voice from next door cut the moment.

"What are you doing to him sweetie? He sounds really turned on."

David tensed a bit wondering what Jade was going to say, embarrassed by being unable to control himself enough to keep his excitement a secret.

"Never you mind Julie." Jade replied in a businesslike voice. "I am just doing a massage." A prostate massage, David thought to himself as her finger rubbed against his most tender spot. "But what are you doing to make that squeaking noise?" Jade asked.

"Oh Sweetie," Julie's husky voice replied, "It sounds so hot in there and this place is just perfect for sex. I just have to look after myself sometimes if I can't get a fuck."

David was suffering from overload at this point. His ass was tingling with previously unknown sensations, His cock was as hard as it had ever been and he knew he was only minutes away from an incredible orgasm, but he suddenly realized there was a girl masturbating in the next room due the lack of a sex partner.

"Maybe I should help her out." He said softly to Jade, half joking, and quietly so Julie wouldn't hear him.

"Oh yes please." Came the voice from next door. Super sexy voice and super hearing David thought ruefully, thinking he may have just pushed this too far.

Jade did not seem happy.

"Quiet Julie." Jade said firmly. She looked at David and said "You would be letting yourself in for something you are not prepared for." Her tone was dead serious and he began to wonder what she meant.

"Huh?" Jade had a finger up his ass and a firm hand around his cock, you couldn't expect him to be at his most eloquent.

"Julie has," Jade said hesitantly, "something extra."

"Huh?" Same excuse.

"She has a cock." Jade finally said, "She used to be a he."

"No way." David said automatically, "That voice is too..."

"Way." Jade said firmly. "Julie darling," she called out over the partition, "do you have a lovely throbbing cock?"

"That's what I'm playing with now." Julie replied in a sensuous voice.

David just shook his head, not believing it. Jade removed her finger and let go of his cock, making him moan in disappointment.

"Do you want to see?" she asked, she looked like she had made a very difficult decision. "It doesn't have to lead to anything else and we can just finish here as we were if you want."

David thought about that one seriously. I'm straight, he thought, and have never had any interest in looking at other guy's cocks, but I am not scared of them either. I once shared a girl I picked up at a pub with Bod, my roommate, and we tried double penetration but he got all worried that he was turning gay when our balls touched as we fucked her and he finished off in her mouth while I fucked her ass. I didn't care, he did, just different attitudes.

So did he want to see Julie and her or his cock?

David slowly nodded, it had gone too far to back out now and to be honest he was very curious.

"Yes?" Jade asked. David heard a squeal of delight from next door as he slowly nodded again.

"Julie love," Jade called out, "you come in here and show this lovely man your cock, but be nice about it."

David heard the table squeak again next door and then feet softly hitting the floor. A slight pause and the door to the other room opened, and then closed. Another slight pause and the door to his room slowly opened. He wasn't in the best position to see, face down on the massage table, flat out lying uncomfortably on his still hard cock, his head twisted around to look past his feet.

The girl who walked in was gorgeous. She was Asian, light skinned, about five foot tall and was also wearing a short white uniform, but hers could not have been bigger than a size six. Her little green nametag confirmed that Julie was her name. She wore black stockings over bare feet. The uniform was straining at the top to hold in a substantial pair of tits that were so distracting that it took a while for David's attention to move up. Julie had the perfect round face framed by long black straight hair. She was petite and delicate, a grown up living doll.

David stared for some time as she looked at him smiling in a slightly longing way. Then David finally realized that they were joking, this vision of beauty could not possibly be hiding a cock under that little short skirt, He had been caught out, and it surely must have been April One.

He smiled.

"You really had me believing she had a cock." David said to Jade.

Jade said nothing as Julie walked past her and stood level with David's head. Slowly Julie lifted her dress exposing stocking tops and garters. He squirmed on the table as the blood flow to his cock increased with anticipation. He was going to see this gorgeous girl's pussy and this could only mean he was going to get very lucky tonight.

Julie's skirt slowly rose and a pair of sheer black panties appeared. There was an unexpected bulge in them. Fascinated David watched as she pulled her panties down and out sprung an erect cock, maybe five inches long and quite thin, but it was definitely a real cock. She had no pubic hair at all. David's jaw dropped as the reality sunk in. Julie was really a man and looking at his rigid cock his masculinity had not disappeared when he embraced femininity.

No, David decided, this is a woman not a man. Sure she has a cock but apart from that she looks female, she sounds female and she acts female.

Report Story

bybb1212© 58 comments/ 413372 views/ 324 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel