tagTranssexuals & CrossdressersShelley's Not a She Ch. 02

Shelley's Not a She Ch. 02


Writers Note: This is the second chapter in a series of stories. Please read the first chapter in order to understand how this all got started. Thank you and I hope you enjoy this one as much as you did the first chapter!


Shelley stood at the kitchen counter, dressed only in one of Matt's 49er's jerseys. Oh how she loved to steal his jerseys since they were so roomy and of course smelled like him. Matt was still asleep in his bed, Shelley had come to enjoy having a mug of coffee alone in the morning especially since Matt was usually grouchy between waking up and getting some caffeine back into his system. Not that she minded, it gave her time to think.

She carried the mug in both hands over to the couch and settled herself down, folding legs and curling into the side of the couch. A sip of the coffee was taken and a smile crossed over her face, still almost amazed at how quickly things had progressed since that one night. Only a couple of months ago they had just been friends, not even close friends, and now she was sitting on his couch in his shirt. They had taken to spending weekends with each other, alternating homes each weekend. Granted she still had to work Saturday nights so it wasn't perfect but she wasn't about to complain.

She and Matt had gotten close very quickly, falling into roles of boyfriend and girlfriend fairly easily and she loved the attention he lavished upon her. Out in public he treated her like any normal woman would be expected to be treated, introduced her to friends and co-workers, the only thing that bothered her was well, he seemed very reluctant to pay attention to her having a dick when they were in bed. A sigh and a sip of coffee, issues like this used to be easier before decided to make the change, she'd just go to a favorite gay bar and commiserate with some of the regulars. Now, well, she just didn't feel like she belonged there. No one said life was simple that was for sure.

Matt lay in bed having woken a few minutes prior from the sounds of Shelley in the kitchen. He was a pretty lucky guy by most definitions of the word, Shelley was a catch. They seemed to agree on quite a number of things, similar tastes in food, décor, even television shows. Yet, there was the elephant in the room and it existed in her panties. Yes Matt chided himself for not tending to her needs he was just having a lot of internal conflicts over it. Society just still wasn't very accepting of anything that could be deemed homosexual by legal definition. Like it or not it had put a road block in his mind and as curious as he was he just couldn't orally please her much less let her penetrate him. Hand jobs, well he could play it off in his mind as if he were stroking himself.

He sighed, the mental block was driving him a little nuts, one day he would just have to do it. For now though, the smell of coffee had permeated the condo. Matt threw on a dark blue plushy robe and walked out to the kitchen, offering Shelley a little smile before ducking in to pour himself a cup. Damn, she was in one of the jerseys which didn't bother him it was just they did a great job of showing off her nipples and leaving little to the imagination. He felt a twitch under his robe, seemed the old boy was almost always up for action.

Shelley watched him walk into the room and settle into the recliner, then waited till he'd gotten a little coffee into his system. "Morning hunny," a smile offered his way and returned, she got up from the couch and went to the kitchen for a refill. "Did you sleep ok?"

Matt had watched her get up and been rewarded with a peek under the jersey, granted all he had to do was ask and she would remove it but there was something about feeling like one had gotten away with a peek that he just loved. His eyes had been rewarded with the view of the tip of her cock, she wasn't overly endowed, just below average but the head was quite large. He had been thinking about it when she asked the question, "Oh yeah...just fine," and slipped back into his thoughts.

Noting that he seemed a little distracted, she walked over to his chair and cradled the cup in one hand and ran her fingers through his hair. She felt his hand come to the back of her thigh and slowly make its way up till he cupped her rear. The rough, callused skin from work around the property gently scratched and yet felt good upon the smooth skin of her rear. A sigh of contentment slipped her lips and eyes closed as she wiggled her rear against his hand. Shelley savored the quiet moment right up until she felt something warm and wet engulf her cock. Eyes flew open and looked down to see Matt had taken her in his mouth, the shock so surprising had it not been for his hand on her rear she might have fallen down.

He had been content to just hold her rear, so tight and yet soft that he often slept curled against her with a hand upon her ass. As he held her though he could see the tip of her cock under the jersey, it was just so tempting and provoked him to go for broke and just try it. Being that she wasn't very large and still soft her entire member ended up in his mouth and his tongue instinctively began to caress the object now against it. The taste wasn't so bad and honestly between that and the texture reminded him a bit of well a finger. He could feel her grow hard in his mouth, that was interesting and he did enjoy the obvious hints of stimulation.

As her cock stiffened he found that his tongue could feel the pulse of her heart and it was beating rather quickly. Slowly Matt began to bob his head, tongue rubbing the bottom of the shaft. He kept a slow speed though, as the one time he sped up there was a squeak and a nervous whisper of "Teeeeth..." well, obviously he needed more practice. Overall it was interesting to him, in a way he felt a sense of power having control over her pleasure and yet he felt dominated from her fucking his mouth. Fucking his mouth, that was a term he'd have to get used to and found it not exactly an unpleasant thought.

Aside from the mistake with the teeth, she was finding him fairly decent at giving head. The biggest turn on though was being able to look down and see Matt's head bobbing on her shaft, every time she saw that it sent shivers up her spine. His style was rudimentary but that was to be expected, it was the effort he put it into it, well that he was actually sucking her off! That alone was something that could make her cum but his tongue pressing on the underside of her cock was helping things along nicely.

Shelley felt his thumb playing around her tight asshole, pressing against it then slipping into her. Gently he rocked it in and out of her ass while suckling her cock. Her moans steadily increased, thighs rocking between fucking his mouth and getting her rear finger fucked. Her hand came down to the chair to steady herself as she felt her knees begin to go weak at the pleasure. She was lost in the bliss of what was happening, lost enough that she forgot that he was new at this and came without warning, flooding his mouth and eliciting a little choking.

At the choking she came out of her daze and looked down at him just as her cock fell free from his lips. The flood of cum that came afterwards was a hint to what had happened. Her cheeks colored quickly with red, "Oooops ummm sorry!" She went off to the kitchen and quickly came back with a hand towel for him to clean off his face, "I kind of got a little caught up and forgot this was your first time." A sheepish grin, hopeful that he wasn't too angry or worse, turned off from giving her another blowjob in the future.

Once Matt finished choking he cleared his throat and took a few moments to just enjoy breathing. She'd really caught him off guard as he'd just finally gotten comfortable with the sensation and he wasn't expecting such force. He smacked his lips at the odd taste, a little on the salty side and a bit runnier than he'd expected, cum had always looked much thicker to him. An offered glass of water was greedily drunk down to clear his palette, "Well it's not like I haven't probably done the same to someone else so I suppose I deserved to have it happen at least once."

Shelley sighed with relief at the comment and got up to straighten herself out, "Well I'm going to grab a shower, join me if you'd like." She wiggled her rear and then skipped off to get the water running for the shower. The jersey was thrown into the wastebasket and she climbed in, turning around to get wet and then just standing in the spray to enjoy the water sliding down her body. The shower door opened behind her and she felt his presence in the stall behind her. Instinctively she bent forwards, offering her rear to him.

Matt smiled at her taking that pose, he'd had a feeling this is what she wanted. The head of his cock pressed to her tight hole and gently he pushed a little ways in, paused to put his hands on her waist, and then slid the rest of the way into her rear. Both moaned softly as thighs pressed to rear and he was buried within her. He took it slow, savoring each stroke in and out and how her rear gripped down on his shaft. Hands caressed the front of her body, squeezing and gently pinching her breasts and nipples then sliding down taut tummy to massage her cock and scrotum. He was ginger with them; she often had a tender head after orgasm. His other hand squirted a little soap on her and he rubbed it over her member and slowly along her front, all while continuing to slowly rock in and out of her rear.

She rolled her head back and pressed against the wall of the shower stall, eyes closed so she could just focus on the sensations going on about her. The biggest of course was his cock up her rear, but there was also feeling the water caressing down her skin, his soapy hands along her torso, and the heat of the steam rising up. This was bliss and it was what she hoped life always had in store for her, if it would just remain this way she'd be happy. She felt him press in hard, then stop rocking and a few moments later her rear was suddenly much warmer and she smiled gratefully accepting his cum. Shortly afterwards he withdrew and the trickle of cum leaked out her rear and began to work its way down the inside of her thigh.

Matt stood in the stream of water and let it rinse him off, watching as Shelley reached for the bottle of soap and squirted some on a scrub. She turned to him with a smile, knelt down and began to gently wash him clean. Shelley seemed to love doing that and he was more than happy to oblige her in her desire to cleanse him. The scrub was handled gently, Shelley liked to take her time and be thorough, and occasionally she'd tease him though with a lick of her tongue on the head or a brush of a fingertip along his own asshole. She had only pushed in to the first knuckle a few times, it seemed she was taking it as slowly as possible with him, perhaps from previous experience.

She let her fingertip caress over that puckered hole, but didn't insert it today as she figured perhaps he'd had enough. Today had been a big day for him and the mental shock sometimes could be a bit much, especially with someone who had identified solely as heterosexual for so many years. A lover prior to the change had explained that to her, it was just best to be very slow and that was the advice she used now. One day she longed to penetrate him, to return the favor and have him feel her cock press against his prostate. As she finished cleaning him, Shelley rose up and leaned up to press a kiss to his lips, "I love you..."

Several days later Shelley strolled through the glass doors and nodded to the receptionist while holding up a bag from a restaurant. The receptionist smiled back at her and went back to her computer as Shelley walked past her. A couple of heads had turned upon her entrance some gazes remaining longer than others. Today she'd dressed up in a pair of slim designer jeans, a red spaghetti strap halter top with a band of gold embroidered circles around the waist, and a low heeled pair of sandals. Most of the folks at the office knew who she was by now but it still felt good to get noticed. The sunglasses were pushed up upon the top of her head and quick steps carried her towards Matt's office. Perhaps it was foolish, but she always made sure to straighten up a bit and wear what was most in fashion whenever she came to the office as she felt that as his girlfriend she was representing him. At least, that's how she felt and besides it seemed he appreciated it.

Caroline, Matt's secretary, laughed a little and gave Shelley a smile as she approached the desk, "Well that explains why he didn't leave for lunch today. His schedule is clear for a bit as you probably know but just so you know he's been in a bit of a mood this morning. Apparently the Miller case isn't going as well as he'd hoped it would." Technically that last bit wasn't supposed to be told to people outside of the office but in the case of significant others most of the secretaries usually gave them a vague idea as to what was going on. They knew that those women and men had to deal with it at home, may as well not keep it a secret.

In some ways Caroline was glad that Shelley had entered into Matt's life, he at least was easier to deal with on Monday mornings. She had been assigned to Matt when he came to their office and had worked with him ever since, learning the ins and outs of his life as people who worked so closely were prone to doing. Only about thirty, she'd contemplated taking the office flirting with Matt further before but thought perhaps she was a bit on the young side for his mid-thirties but this girl had to be no older than her mid-twenties. There was a bit of admitted jealousy there although she had also come to terms with the fact that she had been the one to not pursue Matt in the first place. Loves won and lost in the battleground of life, at least this girl wasn't the raving bitch a number of the men dated. Sure she dressed up like she had money but the way she carried herself and acted wasn't the typical snobby attitude the trophy wives the secretaries hated had. She watched Shelley enter the office then returned back to the paperwork before her.

Matt was on the phone when Shelley entered, talking rather tersely to a client who had gone out and violated orders from the office. This was the part of the job he'd come to loathe, clients who thought that having money and hiring an attorney entitled them to do whatever they pleased counting on their attorney to get them out of trouble. Today it was dealing with the fairly well off Josh Miller and the divorce from his latest trophy wife. The man just didn't seem to understand the concept of keeping it in his pants, this morning brought pictures of Josh hanging out at a strip club and getting a bit too friendly with one of the girls. He slammed the phone down on the receiver and put his face in his hands, some days it really didn't seem worth it.

Shelley sighed, it was one of those days and she was learning to deal with them. Long strides carried her over to his desk and behind his chair, hands came down to the base of his neck and she gently began to rub along the tops of his shoulders and the where his neck met his shoulders. She could feel the tension in them and let her fingers begin to work on them, trying to smooth even just a bit of that tension away. He signed and leaned back in the chair, back of his head pressing lightly to her chest. She slid her arms around and clasped them over his chest and gave him a soft kiss upon the top of his head.

For a moment they stayed like that then she slipped from him and went to the bag, pulling out drinks, a couple of sandwiches, and a bag of apple slices. He rolled his eyes at the apples, "Awww no chips this time?" She quirked a brow and just gave him a look before pulling out the napkins and sitting down. He sighed, "Spoil sport..." and cracked open his flavored water.

They chatted over the meal, normal things about work and things that needed to get done around their respective homes. Matt wiped his face clean with a napkin and threw away the wrappers before leaning forwards on his desk, "So, have you ever thought of going back to school?"

Well that caught Shelley unaware and she used the excuse of chewing her sandwich to give her a couple of more moments to compile a response. "Well, yes, but my schedule can be so erratic..." and she went on to give the usual list of excuses adults have when contemplating going back to school. Not that she didn't want to but the honest answer was like most people it was hard to get back into it, particularly as one picked up responsibilities and those dreadful things called bills. "I did kind of want to study culinary arts, feeding people just always felt right." Though truth be told she really didn't have a goal at the moment, caught like so many waitresses as the money could be fairly decent and just enough to make one not think about the future much.

"Well you can't really keep doing what you're doing, it's got to be taking a toll on your back at this point," he noted. "Of course it would be late to get into a university but maybe a community college would be easier anyways, I hear the classes can feel more like high school. At least they're supposed to be fairly small in size and you could just take a few basic courses to ease in. And I suppose it would be just best if you moved in with me, that way you don't have to worry about making the next month's rent instead of studying for tests."

Lips pursed, she swore he purposefully talked in the most backward ways possible in order to ensure that it took her at least a few minutes to comprehend what the heck he was saying. No wonder he'd become a lawyer. Granted though it wasn't a half bad idea and then it clicked, "Did you just ask me to move in with you?"

"Well, I'm not sure ask is quite the right word. Maybe suggested works better, I mean it makes sense to. Saves on bills, saves you stress, I have more and bigger closets than you do." He flashed her a grin at that one.

She had to admit, he had more room for her shoes. It was just a little sudden, but that did kind of describe how their relationship had been all this time anyways didn't it? Shelley chewed on her lower lip for a few moments mulling this over, they did seem to spend a lot of time together anyways and well it wasn't like he hadn't seen her without her makeup on before. Plus he'd been teaching her how to do finances so he know where she was at financially for the most part. "Ok well, I guess we can look at schools. I still have a couple of months left on my lease anyways, how about we just try me spending more nights at your place until it gets close to my lease ending and we'll see where we're at?"

It wasn't quite what Matt was hoping for, but she did have a decent counter proposal, "Deal, though maybe you should think of going into law." Another grin, couldn't hurt to suggest it.

"And go through all the crap I see you deal with? No way!" She stuck her tongue out at him, "I'd get wrinkles before my time and then you wouldn't be happy having to show off an older looking than she really is girl." With that she threw out her trash, took note of the time and that her shift would be starting soon, gave him a kiss goodbye and walked out the door. As she went to pass by Caroline's desk her head was already allowing the giddy feeling of the relationship going further to get it's time when she noticed Caroline waving her over.

Caroline gave her a little smile, then leaned over and whispered into Shelley's ear, "I know what you're hiding under those pants. We should talk about it sometime." Gave her a wink and went back to her work like as if she'd said nothing at all.

That sent chills up Shelley's spine, how did she know and what did she want were two questions that needed answers and it seemed that she was going to have to be patient in getting them resolved.

Report Story

byJagFarlane© 9 comments/ 26941 views/ 21 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartdresdoe, Cadian122 and 19 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (9 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (9)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

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: