tagTranssexuals & CrossdressersShelley's Not a She

Shelley's Not a She


Her name was Shelley, she was a waitress at the local steakhouse Buck's, and she was the reason that Matt came back to the place every Friday night for dinner. Sure, the sirloin was pretty good and the chef made it a point to offer some interesting sides, but it was watching the swish of Shelley's skirt as she whirled away from a table that was the real draw. She offered a smile as she approached his table, more genuine than the usual waitress smile for the man that over time had become more of a friend.

"Hey Matt, your usual Yuengling Light to start you off?"

Matt returned the smile and nodded his head; some nights were more like this night with the restaurant doing steady business. At the nod of his head Shelley spun around and hurried off towards the bar, pausing only a moment to check that a delivered dinner was to a customer's expectations. He leaned back into the booth, lightly closing his eyes as he listened to the live band play. This week's band seemed to have a slight Southern Rock thing going for it; he supposed that led to the choice of red beans and rice as the side dish. He slowly tapped his foot along with the beat, at least the singer wasn't too shabby.

After a minute or two he heard a bottle placed down upon a coaster and her sit down on the booth bench next to him. He cracked an eye open and offered her a smile. Matt knew Shelley well enough to tell that this had been one of those stressful nights, and that while she outwardly projected the typical happy waitress, inside something had bothered her. However, it wouldn't do to ask her about it while she was working and so he didn't push. She sidled up to him and he leaned in close enough that he caught a whiff of her perfume, the music was loud was his excuse to himself.

"Busy night tonight, huh?"

"Yeah, well a destroyer squadron just pulled back in from a long deployment. Guess they're seeking some real food for a change. As usual though, most can't hold their liquor so it's going to be one of those nights you know? Oh well, they're tipping well so I guess I can't complain too much." She offered a faint smile.

He just nodded his head, one of the downsides of living in a Navy town was dealing with the kids when they came back from overseas. Not that he really blamed them for acting the way that they did when returning, heck he was sure that he'd act the same way in those circumstances. It did mean she was in for a long, long weekend though as plenty of the sailors would be out looking to just get drunk and get a piece of ass and she did have a rather nice one. In fact as far as he was concerned her only flaw was that her chest was pretty flat maybe a B cup if she was lucky but her ass made up for it. He nudged her lightly on the shoulder and grinned to her.

"Oh not like you wouldn't like some young playtoy who has had nothing to do on ship for nine months but workout to warm up your bed this weekend."

She gasped, gave him a playful smack on the shoulder, then laughed shaking her head, "Oh that's just what I need, some kid whose alcohol tolerance went away but still thinks he can down a fifth of Jack." A kiss to the cheek followed, "Ok I better run before the boss begins to wonder where I'm at. I'll put the usual in for you." With that she stood up and hurried off to input the order and makeup for taking that short break.

Matt watched her run off and smiled to himself, he could feel the stress of the week slowly bleeding off. He took a sip of the beer and settled back into the bench to watch the rest of the patrons and listen to the music, lightly bobbing his head to the beat. Occasionally he'd glimpse the top of Shelley's head as she ran around the restaurant trying to keep up with the workload. A secretary had recommended this place three years ago when he moved to the area, the décor was fairly down home and the atmosphere was very laid back just what he needed at the end of the week. Shelley had started working there about oh six months later and they'd struck up a fast friendship though she always held him just far enough away to keep the friendship from evolving into a relationship. Ah well, she was always there for him Friday nights and more than once had spent the evening listening to his struggles, to loves won and lost, to cases fought, and to life lived.

He took his time tonight, just soaking up the atmosphere and a few beers while he was at it. Not so many that he joined the younger folk in getting drunk, just a little toasted but enough that management wouldn't get so annoyed at him taking up the booth all night. Shelley popped in here and there, grabbing little snippets of conversation as she bounced from table to table like a hummingbird in a flower field. He ordered a soda so that she could have something to grab a quick drink from while she was on the floor. Eyes rolled every now and then as he watched her deftly avoid drunken hands trying to wander to her body. Consequences of the job she had called it once, he still didn't like it even though he had learned to keep his mouth shut. Sex sold and the girls knew it, so short skirts and partially unbuttoned shirts were the norm. Not that he minded the view, Matt could just do without all of the attempts at gropes or maybe he was just getting old. Old, at 38, when did that happen? A smirk and a swig of beer, well he worked out regularly and generally watched what he ate so he wasn't in bad shape and didn't feel his age so the thought was banished away as quickly as it came.

"LAST CAAAALLLLLLLL," came the bellow from the bartender. There was a furious scurrying of feet as patrons scrambled to place last orders and the serving staff moved to fill them. Then, as the last of the orders was finished it was as if a collective sigh was placed in the area and the mood visibly lightened among the staff. They watched wearily as tabs and bills were paid and drunken patrons started their shuffle out of the establishment and into the night. Shelley flopped down in the booth alongside of him and took a long drink from his beer. Her hair was ruffled and face had a sheen of sweat upon it but the night was almost over, all that was left was to count out tips so the earnings could be reported and make her way on out. It was, well a good night as far as the pay went but nights when sailors and soldiers returned home always were.

As she prepared to leave Matt offered her his arm and she graciously took it. It had kind of become a routine between the two of them; he often walked her to her car when she'd had a busy night. Not that it was a one way deal, on the occasional night he worked late Shelley had swung by on her way to work to drop him off something to eat. They chatted on as they walked, just the random things people talk about until they got to her car. He got ready to make the way over to his before he felt thin fingers wrap around his right wrist.

"Wait, please."

He turned to see her staring up at his face, teeth bit down into her lower lip. She looked down for a minute and twisted her foot around on the ground before speaking.

"Ummm, maybe...well would...would you like to come by for a cup of coffee?"

Hazel eyes darted upwards, looking at his almost pleadingly. Matt blinked and took a moment before responding, "Sure coffee would be nice." A little understated perhaps but he was caught off-guard, why now? Eh, not something he was going to dwell on.

She grinned at the response with a little hop. "Okies, just follow me. I promise I'll drive slowly." That grin never left her face as she got into her car, waited for Matt to get into his and headed off towards her home, an apartment on the edge of town. It was your run of the mill typical suburban apartment complex. Nothing overly special, but they kept the apartments in decent shape, the rent was almost reasonable, and well it wasn't a place you'd be afraid to take a date back home to.

Shelley skipped up the stairs to the third floor, for once not minding them, leaned over the railing at the top and grinned down to Matt, "C'mon slowpoke!" Once inside, she ran about to do a quick straightening up of her place and went over to the coffeepot to get a pot brewing.

Matt took his time coming up the stairs, he had no idea where she'd gotten the energy to run up them like that. Maybe that's why her butt was so nice, he smiled a little to himself at the thought and took a moment to catch his breath at the top of the stairs, ran his fingers through his hair, and entered her apartment. He paused after closing the door, taking a moment to look around the place. Even though they'd known each other for a couple of years now he'd never actually seen the inside of her apartment. It was cozy, fairly typical single person's apartment, one bedroom from what he could tell. He followed the sounds coming from the kitchen and sat down on a stool in front of a breakfast nook just watching her get together the mugs of coffee. She placed mugs, a sugar bowl, and creamer on the nook, "Help yourself when it's down brewing. I'm going to get changed out of these work clothes." Off to the bedroom she headed, closing the door behind her.

When the door was closed, Shelley leaned against it for a moment, just breathing and giggling to herself that Matt really was in her apartment. She stripped out of her work clothes and tossed them into the hamper, then went to the mirror to give herself the one over. Due to the hormone's she'd been taking over the last few years she had finally started to grow breasts and just recently celebrated when they hit the small B mark. So they didn't get much attention, but they were all natural and all hers! Tummy was flat enough, maybe a pound or two heavy she thought. Eyes finally drifted lower and she looked over her currently raging hard cock. It wasn't huge by any means, about four or five inches long but it had a large head and a slight curve to it. She couldn't resist and gave it a little stroke, while some had surgery to get rid of theirs Shelley had more or less accepted it was a part of her and decided it wasn't worth getting it removed. Of course she had to keep it hidden and that could be a pain, thank god for Spanx. In her mind they were the greatest invention ever as they helped to keep her little extra parts tucked away. They were the first thing she donned and were followed by a pair of jean shorts. She debated the need for a bra, a recent shopping excursion had led her to a really cute one that she'd been dying to show off but on the other hand nipples poking through her shirt just sounded like fun to tease with. Foot tapped against the floor for a few moments as she debated, then decided to wear the bra another day and threw on a pink VS t-shirt with the word "PINK" emblazoned across the chest. A quick check of her makeup in the mirror, couple runs of the brush through her straight, long, dark brown hair and she reapplied her lipstick before deciding she was as good as it was going to get and slipped out of the bedroom.

Matt gave her a smile as she came back into the room and she noted the desired effect, his eyes dropped to take note of hardened nipples poking hard against her shirt. She gave a little waggle of hips and went to fill a mug, topping it off with some Baileys and gestured the bottle towards his mug. At the nod she topped off his drink and sauntered off towards the couch. Shelley flopped down on one side of the couch and waited for him to join. They chatted for a while, going through several cups of coffee and each time one came back from refilling their mug the distance between them on the couch seemed to decrease until she was pressed up hip against hip with him.

Shelley's eyes closed for a moment as she savored the feeling of being pressed up against this. She breathed in his scent and slowly let it out. A tiny pout was forming as she felt him shift a little then eyes opened wide as his lips pressed against hers and she felt his the tip of his tongue enter her mouth. Her eyes slowly closed as she pressed up against him, opening her lips more to welcome his tongue into her mouth, greeting it with her own. She could feel the slight scratch of his stubbly chin upon her jawline and just moaned into the kiss. Her hand caressed along his side and around him till it rested on his back and she used it to hold him close. Tingles went down her back as years of pent up sexual desire were released. As they released the kiss and pulled back Matt took note of a change in her eyes, how they were filled with lust and an almost predator appearance. She took his free hand and guided it to her shirt, sliding it up and towards a breast while her other hand slipped down towards his pants. She caressed him through the material, massaging his shaft as her hand rubbed up and down.

Shelley sunk down to her knees and wiggled her way between his legs, looking up to Matt with a devious grin upon her face. Deftly she undid his belt and the button of his pants then leaned forwards to grasp the fly of his zipper between her teeth and unzip his pants. She grabbed the waistband of the pants and his boxers, pulling both down till they were around his ankles. Containing herself for a moment, she looked him over and licked her lips at the sight of his long, veiny, and thick member standing proudly erect before her. She pulled the t-shirt over her head and threw it aside before leaning forwards and rubbing her chest upon his thighs. Shelley looked up, lips just millimeters from the tip of his cock and whispered, "I have wanted to suck you off forever. When you're ready to cum make sure you let me drink every drop and feel free to fuck my slutty mouth as you wish." With that, fire red painted lips parted and she took the head of his cock into her mouth. Her lips stretched as she lowered her head, taking inch after inch into her mouth, pausing for a moment as she felt him hit the back of her throat and then pushing him in. Only toys had ever gone so far but damn she wanted it, she craved every inch to be within her and so even though her jaw ached a bit from stretching out, she pushed her head down till her nose nestled against the trimmed pubic hair. When she realized he was all the way in she released a low moan and held him for as long as possible. The feeling of finally having him in her mouth, of knowing she was getting to pleasure this man that she had fallen for was incredible. It was only when her body screamed in a need for oxygen that she backed off, sliding up till the head rested upon her tongue.

Shelley held the head in her mouth for a minute or two, eyes closed as she just enjoyed it, the feeling was intoxicating to her. Here she was, in her apartment, on her knees, and holding in her mouth the cock of the man she had craved and masturbated repeatedly to images of. She felt his hand slip through her hair and rest upon the back of her head, the light bit of pressure placed upon her skull to continue with what she had started and was more than happy to continue with. One hand wrapped fingers around the base of his cock, gripping him firmly, while her head lowered to meet lips to fingers. Slowly at first, she began to bob her head upon his cock, fingers following along with her lips. Shelley made sure to coat his cock well with spit to keep him lubed as her pace steadily increased . Once she found a comfortable rhythm she put everything she had into working that beautiful cock. Any tricks that Shelley had learned over the years were put into place, she craved and needed to make the most of this. The fear that this might be the only time she would ever get to feel him within her drove the need to make this the best blowjob he had ever received. Her tongue rubbed up against the underside of his cock, the tip flicking just below the head each time she bobbed upwards. Her free hand snaked upwards, feeling and cupping his balls. They felt swollen to her and she briefly wondered if she would be able to contain it all when he finally came. Shelley rolled them around in her hand, massaging them, loving them. Everything about Matt was just as or even better than she could have hoped for and the moment made each one of her fantasies fail in comparison. His breathing was getting shallower by the second and she could feel his body begin to tense. With a delightful glee, lips were slid up till only the head was still within her mouth and her hand began to stroke rapidly upon his shaft. Shelley craved it, needed him to cum in her and it showed in how rapidly she stroked that cock of his. Her grip was firm enough that she could feel the cum as it traveled up his member, giving her a split second to brace herself before her mouth was flooded with the salty goodness. Shelley swallowed as quickly as she could but was no match for the sheer volume of cum spurting forth, some of it leaked out of the corners of her lips and down his cock. She held her head still as he emptied into her, and as the flow ceased she began to bathe his cock with her tongue licking up every drop then enveloped half of his member back into her mouth and raised her head, lips caressing his member to be sure he was clean. As she finished her task, Shelley smiled up to him and whispered, "Thank you."

Matt sat back, trying to catch his breath as he watched her clean and bathe him. That was easily one of the best blowjobs he'd ever received and she was thanking him? He just smiled, unable to speak for a few moments, watching as she got up went to the kitchen and got herself a glass of water. When she returned with a glass for him he reached over, wanting to return the favor but she stopped him short of his goal. "Not tonight hun, it's late and I'd like to get to bed and not ruin my sleep schedule," was her response. Little did she know she couldn't have cared less about sleep but was purely afraid of ruining the night they'd had. Shelley retrieved him a blanket and one of her pillows, helping him to makeup a bed on the couch. Matt did wonder a bit about why she would be willing to have sex but not sleep together but decided that not pursuing the issue was in his better interests. He gave her a tender kiss goodnight and managed to steal a soft grope of her rear, swearing he could feel her push against his hand. He heard the door shut and the click of the door knob then laid down on the couch, pulling the blanket around him. The pillow smelled of her and he nuzzled down into it, yawning as the alcohol and the orgasm did their job and sent him off to slumber.

Shelley quickly stripped out of the rest of her clothes and threw them aside just before clambering into bed. She needed relief and she needed it NOW, so her hand fell to one nightstand seeking her trusty and favorite toy and a tube of lube. The toy was a realistic dildo, not quite as big as Matt but it always did the trick. She smeared the length and head with lube, then a little extra lube upon her puckered hole and slid the dildo deep within her arse. Shelley spared no mercy on her poor rear, slamming that dildo in and out as hard as she had wanted Matt to fuck that tight hole. She grabbed her dick, stroking it hard and pushing herself quickly towards orgasm. As her body shook a small amount of cum squirted from her dick and coated her hand. She brought the hand to her lips and licked up the cum then gently slid the dildo from her stretched out hole. The toy and lube went away and she used the door joining the bedroom to the bathroom, never sure before why it had a door between the two rooms when the hallway door was two feet away but now glad it existed, and used a washcloth to clean herself up. Upon returning to the bedroom Shelley curled up into the bed and buried her face into the pillow. Sure that he couldn't hear she finally allowed her emotions to get the better of her and began to quietly sob into the pillow. Here the man she desired most finally in her apartment, her with a bellyful of his cum, and she feared that it would all be lost away in the near future. She would cry herself to sleep, curled up in the fetal position holding her pillow tight.

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byJagFarlane© 8 comments/ 87653 views/ 71 favorites

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