Day Dreaming

"David, this has been the most...wonderful day of my life," Aaron, the "bride" said, leaning backwards into the groom's embrace, sharing a quiet moment in the garden, "I wish it did not have to end, I feel a little like Cinderella."

"I'm so glad you could help me out," David said, hugging Aaron with gratitude. "I promised my grandmother that I'd get married before she officially passed title to the company over to me. I know it was stupid to have to lie to her, but what choice did I have, her dementia is getting worse and worse and someone had to step in."

"You could have just, you know, actually found a woman to marry," Aaron laughed, feeling a little dizzy in David's strong, embrace.

"I have not found the right girl, Aaron, and I don't want to be a divorced guy when I do, this was the best think I could think of that would make my grandmother happy, save the company, and save me from a bad marriage."

Aaron thought back to the night with David three months ago, sitting in David's loft apartment overlooking a fashionable downtown neighborhood.

********************

"What the fuck am I supposed to do, Aaron," David asked, sipping his scotch. "It isn't like I'm trying to take the company out from under her, but she hardly knows what is going on anymore, she's losing her mind, slowly, it's killing things."

"So, you're not allowed to take over till you get married," Aaron asked, twirling his glass of Pinot Gris in his hand.

"Nope."

"And you don't want to just find some girl to marry, even to fake it?"

"Hell no. And have her somehow claim that half the fucking company is hers?" David poured a second glass of scotch, sighed.

"I don't know then, buddy."

"Wait, wait, maybe that's it," David said. "I could fake it."

"But you're right, David, what woman would go along with that."

"Fake it, Aaron, that's the point. I wouldn't need a woman to go along with it if my bride wasn't a woman."

"I'm not following you," Aaron took a sip of his wine.

"I need someone I can trust. If I knew a girl like you, maybe I'd risk it, but that isn't happening, not in the time frame I need."

"So?"

"That's it, Aaron, I don't want a real marriage, that's too risky, financially, so I need to fake it."

"Okay..."

"What better way to fake it...what if the bride wasn't a woman?"

"Wait, wait," Aaron said, "you lost me."

"What if the bride wasn't a woman, but instead was a man. Same sex marriage isn't legal in this state, Aaron, if my 'bride' was not a real woman, we could get married, my grandmother would be satisfied, but there would be no legal risk to company ownership."

Aaron thought for a moment, tried to poke a logical hole in David's crazy plan, but could find but two. "Where are you going to find a guy that you could pass off as a woman and wouldn't you still have to trust that guy?"

David did not answer, instead poured Aaron another glass from the bottle, sat back, looked at his friend. "Where am I going to find a guy I can trust that also isn't the most masculine guy in the world?"

"Right," Aaron said, crossing his legs at the knee, reaching for the stem of the wine glass.

Aaron happened to look up at that instant, saw himself, his thin frame, David, more muscular, in the full mirror between the wall to ceiling windows behind the chair David was sitting in. He stared, suddenly feeling uncomfortable.

In reaching for his glass, the way his legs were crossed, his dangling foot was pointed downward, toes almost to the floor. He had just touched the stem of the glass, his fingers gently pinching, his manicured nails the closest thing to David.

It struck him, really, for the first time, the contrast between the two college roommates. David, the athlete, strong, masculine, louder, somewhat brash, but not overly so, to Aaron, the dancer and actor in college, happiest on stage, soft, subtle, and almost...feminine.

"David," Aaron gasped, looking at his friend again, seeing the look in his eyes.

"You're the only one I can trust, Aaron," David looked down at his glass of scotch.

"But I," he started to object, on principle, but he had trouble formulating the right words, his mind instead reverting to the more easily explained practical. "There is no way I could pass as a woman."

"Do you know how much money I have, Aaron?"

"What's that got to do with it?"

"Money buys clothes. Money buys stylists. Money buys make up artists. Money buys all of that. What money doesn't buy is trust, loyalty, friendship. My money can make anyone look pretty, it can't make me trust anyone. I trust you."

It turned out David was right.

Aaron's feelings about the scheme came and went, but his undying loyalty to his friend was unshakable.

*******************

"You're really enjoying yourself, Aaron," David asked, making no effort to relax the hug he had on his 'bride.'

"Yes. Whoever says it, is right, a bride feels so special on her wedding day, she never does want it to end."

"It doesn't have to end, Cinderella," he said, his voice confident, leaning forward, towards Aaron's bare shoulder, until his nose was touching her skin, his lips gently resting on her shoulder, parting, then kissing.

"David," Aaron shuddered, meaning to scold him, but her rebuke sounding more like a gentle moan when she turned her face towards him.

"We have the honeymoon suite at the Ritz, Aaron."

She felt him squeeze her just the slightest bit more, just enough that his waist, heretofore several inches away from her, now pressed against her back, one of his strong thighs resting against the back of her leg, right where the garter strap from her corset attached to her white silk stocking.

He kissed her shoulder again, at the same time, his right hand moved from hers to the front of her gown. He touched the satin at her waist, let his fingers gently trail downward, over her hip, her thigh.

"David," she sighed, wanting to pull away, instead, letting her body fall backwards, closer to him, the tingling sensation of his lips on her skin too much to break. "David, I'm not a woman," she tried to reason.

"I know exactly what you are, Erin," he told her gently in her ear, somehow using is voice to make her name sound feminine, no longer masculine.

Erin saw a couple of guests pause at the edge of the garden, watch from a respectful distance, letting the bride and groom share their moment.

"But David..."

"Do you know why I've never found the right woman, Erin? Because I was blind to the fact that she was right there before me."

"David," Erin melted slightly, just slightly, scared at her own desires.

"I love you, Erin," David kissed her neck.

Erin almost collapsed, but he felt it, held her, helped her turn. "I love you, too," she said, turning, letting her lips press forward, finding his, kissing him, surrendering, giving up.

Girl Talk

Surrender

"Is this your first time, with a man" he asked.

"Yes," she answered staring at the ground.

"You're nervous," he asked, gently lifting her chin so she had to look him in the eye.

"I...I'm sorry," she whispered, wishing she had more confidence at this very moment.

"Sorry? For being nervous?"

"Yes," she admitted. "I know that must upset you."

"Upset me? Darling, that makes you all that more desirable to me."

"I don't know what to do," she said.

"No, pet, you know exactly what to do. Don't pretend you have not dreamed about, fantasized about this moment for years."

"I..." She felt her face flush, his words touching her, honest, knowing. "Maybe."

He lifted her chin again, gazed at her. "You've been imagining this moment from the first time you realized you were different."

"Yes," she admitted, thinking quickly now, compressed, thoughts she had for years.

"Sissy?"

"Yes," she swallowed, that one word cutting like a knife, through all her defenses, all her fears, all her hesitations.

"You know exactly what to do." He was unbuttoning his pants, carefully, not letting them fall, but loosening them so he was free.

She stared at it, the thing she fantasized about for years, as he said. Hard. Powerful. Masculine. Involuntarily, she reached for it, let her manicured fingers touch it, grip it, wrap around it. She held it, felt it throbbing, gently, but thickening, the strength. It was all that a man was, everything, there, before her eyes.

Looking at it, she never felt more feminine in her entire life. Never felt her own maleness feel so small, such a little part of her. Looking at it, she realized that though born a boy, she was nothing like him, nothing like a man, never thought that way, never identified herself as so.

He waited, patiently. He knew the thoughts running through her head. It took only a matter of seconds, but he knew that the beautiful creature before him, whatever her genetics, was in that instant, a woman. He knew that she knew.

He watched as she opened her mouth at the same time her eyes fluttered, closed.

He watched as she leaned forward, drawn to it, accepted, wanted, desired.

He gasped as her soft lips touched him, shuddered, his own masculinity as powerful and overwhelming to him as her femininity was to her.

Both born males, he knew as he felt her wet lips touching him, now, forever, he was a man, she was a woman.

Man.

Sissy.

He knew.

She knew, too.

Accepted.

Desired.

Wanted.

Needed.

She surrendered to her lifeblood, her calling, to herself.

He made her what she was. What she wanted.

"There, there," he pet her hair, holding back, knowing enough to let her pace, trying not to let himself pull her mouth over him.

She surrendered. Worshipped. Woman. Man.

Image from Sharply Dressed Man

I don't do too much hard stuff but...

...oh, hell is this fucking hot.

Which girl do you want to be?

As for me, I'm the one moaning into the bedsheets as Emily eases into me.

From: twiterverted and Penthouse, obviously.

P.S., this is minor, but the tub in the bedroom? Really? Really?

Gender Bender

Yes, I like male to female gender bending.

But, hey, I like female to male gender bending, too.

A beautiful woman is beautiful naked.

A beautiful woman is beautiful in lingerie.

A beautiful woman is beautiful in a suit and tie.

It's funny, when she's more masculine than me, yet more feminine, too.

"Don't worry, baby, if you can't be the man, I'll be happy to."

From: twiterverted

Girlfriends

I did not get a chance to blog about Saturday. Emily dragged me shopping Saturday afternoon, a precursor to the teasing the other morning in a way.

"I want to get a new duvet cover for my bed and I saw some things at Nordstrom's that I'd like you eye for."

Well, there is no question I have an eye for design. Sure, not every woman's boyfriend is going to be helpful in picking put a new duvet cover, but that's one of the benefits of a boyfriend that's part girlfriend, too.

After an hours of looking at bedding, we found a lovely duvet set with some adorable pillows:

We bought it, took it out to the car, but were not done.

"I want to run back in and look at something else I want your eye for," she said, batting hers in that way that makes me melt and do anything she wants.

"Okay." I guess I assumed something else in bedding, so was somewhat surprised when we wound up in the dress department.

"What do you need a dress for," I asked, my brain about half a second behind my mouth.

"For Memorial Day Weekend, silly," she said, touching my arm. "Evan said there is some fancy thing at his country club on Saturday night."

"Oh," I said, the jealously part dominating anything else. Of course. Evan. Her weekend. With him. I was pouting, I don't know why, it wasn't as if I was an innocent in all this, as if I did not play along, even encourage her, as if I didn't enjoy it, toeing the line, as much as she. As if I didn't fantasize about her with him, whether I wanted it to happen or not.

Given her own hesitancy, her own enjoyment in playing around that forbidden line, looking at it, approaching it, testing it, she wanted lightheartedness, I sensed, by the look in her eyes.

To this day, I do not know if she has slept with him.

Wait, no that isn't right. I'm certain she slept with him.

I just don't know if she slept with him since we've been together.

She has gone to visit him twice now, once in late 2007, last Memorial Day Weekend. He has been at her house once.

I don't think she has had sex with him since we have been together. But I'm not entirely certain.

Does she want to?

Don't know.

She teases me about it.

She fantasizes about it.

But is the teasing all?

"Sara," she looked at me using my feminine name in public, her soft voice melting away all of my masculinity, melting away the "boy" clothes I was wearing, mentally uncovering the lingerie I had on underneath, mentally transforming me from boy to girl.

"You don't have to dress shop with me, I just thought it would be more fun doing this with my favorite girlfriend. I can ask Jill or Erin if they would rather..."

I swallowed. Feminine. Girlfriend. Dress shopping for a weekend away. A date, even.

"I..."

She smiled, widened her eyes, asking.

"Okay," I said, slipping so easily into girlfriend, only in the back of my mind knowing that I was helping the love of my life shop for a dress to wear on what was basically a date with Evan.

I'm on Nordstrom's web site, trying to find pictures of things we looked at:

"Really cute," she said, "but a bit too prom like. I don't want to feel like I'm someone's college age daughter."

"This," I asked.

"Better, if I'm going strapless, a bit more age appropriate. Pretty."

We both love the lavender, but they did not have her size to even try on.

She loved how this one could be tied behind the neck, halter style, or lower, like in the picture.

A little black dress she loved. "I could wear stockings with this one."

Yes, she said stockings. Not pantyhose. Yes I noticed.

"Too much of a 'I'm going to get fucked later tonight' don't you think," I asked.

"Maybe that's the message I want to send," she chuckled, putting it back on the rack.

The runner up, which we both decided was a tad too short, though lovely.

Above, is the winner. The length was more age appropriate, yet still above the knee. She loved the bodice. I agreed. It showed off her breasts, without having them spill all over. The empire waist gave her the illusion of curve that she does not have the most of.

Simply, on her, it was beautiful.

Walking back towards the entrance we came in through, we walked by the lingerie shop. Yes, of course.

"You...you want to look, don't you," I asked, my own eyes drawn to the racks of nighties and pajamas lining the aisle.

"I really don't want to sleep naked," she said shyly.

I picked up a set of the nearest rack, half joking, but in a way, not entirely. "Something like this?"

She frowned. "For summer? No."

"This, then?"

"Kind of plain."

"This is cute."

"Yea, I suppose. I don't know, I guess I prefer something like this, or this."

We looked around for awhile, she bought both.

So, this was the prelude to her masturbating the other morning, teasing me about her upcoming weekend. She shopped with me as her girlfriend, she teased me as her sissy.

The Interview

“Well, Ms. Upham, everything seems to be in order on your resume,” he said, focusing as closely as he could on the paper between him and the interviewee, almost using it as a shield to keep himself from staring at her nylon covered legs. “Degree from Fordham, an internship with Continental, and then three years with the Canton Group in Sales Analysis. You seem to be exactly what we’re looking for.”

“Thank you, Mr. Harris, that’s such a relief to hear; since the market turmoil and Canton’s problems, it has been so hard to get an interview, let alone a job.” Nikki was nervous, desperate for a job. In the last years Nikki had not a single second interview, let alone an offer. Of course, that was spent as Nick, looking for a job as a boy, as she had been born. Maybe it was true, sex appeal did help, it sure seemed to be here, if she could only stay calm, try to forget that she was a boy dressed as a girl, a sexy one at that.

“Yes, well…” His voice trailed off, he glanced quickly at the woman in front of him, eyes quickly darting from her breasts to her legs, then back to the resume. No, no, it could not be, he thought to himself, it made no sense.

“Yes, Mr. Harris,” Nikki asked nervously.

“I, maybe it’s nothing Ms. Upham, but Scooter Porter and I play handball together at the same club, I remember him mentioning that he had a sharp young associate from Fordham working for him.” He knew it could not be, but something was not right.

“Yes?”

“Well, it’s just, I remember, I think, pretty clearly.” He could not believe he was about to voice his thoughts. “Scooter telling me his new wiz kid was named Nick. Nick Upham, as I recall.”

“I…” Oh fuck, Nikki thought, fuck, fuck, fuck.

“I could be wrong, but…I know he told me it was Nick, not Nikki. It just doesn’t make sense to me.”

“Are you sure, Mr. Harris, maybe you didn’t hear him correctly.” Stay calm, stay cool, this would be okay.

“No, no, Ms. Upham, he was pretty explicit. His new associate was named Nick. I remember him telling me we should see if Nick plays handball and he could join us at the club. See, the thing is, we belong a male only club, so it had to be a guy.” There was no way. Right. He was being foolish, there was no way that this beautiful woman, with those breasts, those legs, there was no way.

“Um, did you see on my resume, Mr. Harris, I put together an analysis program for regression in emerging markets.” Distract him. That’s what she had to do, distract him. Forget sex appeal for the moment. Fuck, why did I wear such a short skirt. Fuck, why did I wear a skirt at all. What the hell am I doing trying to be a woman. This is crazy. Nikki didn’t care how much she actually liked dressing as a woman, how strangely erotic it was.

“Yes, yes, Ms. Upham, as I said, you’re exactly what I’m looking for,” he responded, wondering how the hell he said that. Just what he was looking for? What the hell. “Anway, Ms. Upham, well, I can’t help but thinking you’re hiding something from me.” He had to ask, there was no way he could let this go, no way.

“Well, I…I’m not really sure how to say this, Mr. Harris, it’s rather embarrassing.”

“Ms. Upham, if there are core values here that we put above everything else, they are honesty and intergrity.”

“Well, Mr. Harris, I…I guess…you see, I…I’m not exactly a, what’s the best term to use, a genetic girl,” Nikki burst out, hardly believing that she could have such bad luck. Nikki knew she passed as a woman, but he had to know Scooter? Fuck!

“What…what the hell does that mean? Not a genetic girl? I…I’ve never heard that term before, Mr. Upham,” Mr. Harris said as it slowly dawned on him what was going on, no matter how badly his brain did not want to actually admit that this beautiful woman might not be a woman at all.

“Er, Mr. Porter was right, the…his new associate was named Nick,” Nikki said, her face reddening.

“That’s what I thought! So you didn’t work for Scooter. What, did you make all this up, is this all a lie?” It had to be something else, it had to be. There was no way this woman wasn’t a woman, there was no way he was actually attracted to wasn’t actually…no way.

“No, Mr. Harris, I did work for Mr. Porter,” Nikki said softly, trying to figure out what to do, how to get out of this.

“I don’t understand. His associate was a guy named Nick. Yet you’re telling me that you worked for him and that…no…no…that doesn’t make any sense. You’re…” No way, there was no way!

“Yes, Sir, I was born a boy. I guess I still am, in some way, anyway, a genetic boy, though I…I don’t go by Nick anymore. I go by Nikki, now.” There, she admitted it, both to Mr. Harris and to herself. This wasn’t just a ploy to get a job, this was more, this was Nick somehow admitting more, admitting, however strangely, admitting to himself or herself, that he just might be something more than to him or her, something feminine, something…a woman, a woman inside himself.

“You’re not a woman? No…no…that isn’t possible. You’re…I’m not sure how to phrase this with sexual harassment laws and all, but…you’re beautiful. How can you be a boy,” he asked, unable to use the word ‘man’ to describe her, not with those breasts, those legs, not when he found her so fucking attractive.

“I am, Mr. Harris,” Nikki, face flush again, unable to explain that while she might be a genetic boy, for the first time in her life, right there, in that office, she wasn’t anymore, she wasn’t a boy, she was a girl.

“You…you have…boy parts,” he said, half statement, half asking.

“Yes, Sir.” Suddenly Nikki was as ashamed about her small penis as she had ever been in her life.

“I can’t believe I’m about to say this, Ms. Upham, but, fuck it, I don’t believe you.”

“I…I can show you, Mr. Harris,” Nikki heard herself say as if it was someone else saying it.

“Oh, fuck, you…you…you have a…a…” What? What word was he searching for? Cock? That wasn’t right. That would be his natural word. Cock. But how could that be right? Fuck, look at her.

“A penis, Mr. Harris,” Nikki said softly, the word sounding strange on her lips. “Yes, Mr. Harris, I suppose I do.”

“But you have,” he looked at her chest.

“Breasts, Mr. Harris.”

“Breasts. But…you look…you’re…you’re beautiful.”

“You’re going to make me blush, Mr. Harris,” Nikki whispered. Beautiful? Did he really find her beautiful. My goodness, how feminine this made her feel, how pretty, how womanly, how wonderful.

“Turn around, Ms. Upham,” he heard someone say, he heard his own voice say, staring at her legs, at her breasts, needing to see for himself, not sure why.

“Mr. Harris, I…” Was he really asking? Did he want to see what she thought he wanted.

“Fuck, look at that ass. I’m sorry, I don’t mean to be so crude, but, fuck, you’ve got better legs, a better ass, than any woman here.” The words flowed again, he knew he had to see more, no matter what happened, he had to see, he just had to.

“I do?”

“I guess you do have a penis, Ms. Upham,” he said touching her gently, rubbing, stunned at the swelling going on in his own pants, feeling his cock while touching her soft penis. “But fuck if you don’t have the smoothest, most fucking feminine…”

“Mr. Harris, please, you shouldn’t,” Nikki said softly, as soft as her feminine penis, as soft as her legs, as soft as her breasts. She said it with no conviction, no feeling. She might just as easily told him to do more, to touch her more, to rub, to feel, to…

“Do you want me to stop, Nikki,” he asked hoping, mentally begging, she said no.

“Oh, fuck, Mr. Harris, oh fuck, oh fuck, that…that feels…”

“Do you want me to stop, Nikki?”

“No,” she said so quietly he could not have heard her.

“What?”

“No, please, no, no, no, please, don’t stop, don’t,” Nikki moaned as his hand rubbed her crotch, as his had touched her, teased her, excited her.

“Do you want to take off your skirt, Ms. Upham? Or would you prefer I stop and we can get back to discussing the job opening,” he toyed with her, thinking of one opening he never imagined thinking about.

“No, no, please…please don’t stop, Mr. Harris.” God, why was he torturing her like this, teasing her. Why couldn’t he just be a man, why couldn’t he just take her, like a man would, should.

“Are you sure, Ms. Upham? I don’t want this taken the wrong way, but I love a woman in nylons,” he said, running his hand over her legs, the nylon touching him as it always did. Her legs were as sexy, hot, smooth, beautiful. God he wanted her.

“That feels so good,” Nikki moaned, shuddering at the feel of a man’s touch.

“I just love running my hands over a woman’s legs, over her pantyhose, teasing her, toying with her.”

“Mr. Harris. I…I’m not sure about this,” Nikki belatedly said, suddenly on edge, realizing she was about to hit the point of no return.

“You’ve never had a man touch you, have you, Ms. Upham?”

“No…no, Sir,” she admitted softly, wondering why she had ever waited for this.

“You’ve fantasized about it though.”

“Yes,” she said quickly, never dreaming she would ever tell someone something like that.

“Turn around, Ms. Upham. I can’t say that I’ve ever been attracted to a man, but let me tell you, you’re no man.”

“No, Sir.”

“Look. Look Ms. Upham. Look at those breasts. Look at those legs. Look at that smoothness, the soft, the feminine, the beautiful lines of your pantyhose.”

“Oh god, oh god.”

“You’re swelling, Ms. Upham,” he laughed, stroking her, using his fingertips, just like he would to a woman, any woman.

“I’m sorry, Mr. Harris, I can’t help it.”

“No, Ms. Upham, no woman can help it when she gets excited, when her clit starts tingling.” She was a woman to him.

“Mr. Harris, I don’t know if we should.”

“Why don’t you have a seat, Ms. Upham,” he said, commanded, pulling her, spinning her onto his lap, onto his erect cock.

“Mr. Harris,” Nikki yelped, feeling his erection, his throbbing, suddenly losing herself.

“Yes, Ms. Upham?”

“You’re…you’ve got an…you’re…” She could not speak the word, so confused was she by her reaction to feeling him press against her, by her grinding, her deep, sudden need.

“Yes, Ms. Upham, I am.”

“I…I never…”

“Do you want to stand up, Ms. Upahm?”

“I…no…no…I want to…ohhhh god, that feels so good on my…my…”

“Pussy?”

“Yes,” she groaned, “yes, yes.”

“Ms. Upham,” he said, “stand up, take off your dress, I want to see your breasts,” he said, pushing on them as she sat on the edge of the desk.

Nikki stood, shaking, both from desire for him, for his cock, the throbbing she was feeling a second ago, now not, and from nervousness.

“Turn around,” Ms. Upham,” he ordered her.

“What…what are you doing,” she asked, almost shaking at the sounds, at his belt unbuckling, at his pants dropping, at his shirt coming off.

“I’m getting naked, Ms. Upham,” he chuckled, pushing her forward slightly, pushing her so her hands went to the desk in front of her, involuntarily, as she bent over.

“Mr. Harris,” she squealed. She felt his hands on her ass, grabbing her pantyhose, ripping, just enough. Just enough to expose her pussy ass, but not enough to allow her own small penis free from the nylon trapping it against her.

“Hold still,” he growled, spitting.

“Mr. Harris,” she protested, loudly, “you can’t…OHHHHHHHHHHHHH,” Nikki felt his fingers on her, touch her, probing, pushing, something no one, man or woman had ever done to her before.

“Mr. Harris, please,” she gasped, groaned. “I…I don’t know…I don’t know…I don’t know…” She kept chanting, never finishing, not saying no, just chanting.

“Nikki,” he laughed softly.

“What, what, what?”

He moved his soaking wet fingers around her rim, teasing, toying, tormenting. “Your pussy is soaking wet and I’m going to fuck it.” He pushed one, then two wet fingers into her pussy ass, trying with all his might not to shove his whole fist inside this gorgeous boy-girl.

“Oh fuck,” Nikki yelped as his fingers, one, then two pushed into her. “Oh fuck, fuck, fuck.”

Then they were gone, replaced quickly by something larger, thicker, harder. Nikki knew what it was, of course, knew that his cock was now poised against her, waiting, knew that a man’s cock was on the verge, was touching her.

“Mr. Harris, please, please,” she begged, unsure if she was begging him to stop or begging him to finish.

And then, in the blink of an eye, in an instant, he made the decision for her and she closed her eyes and surrendered as she felt it quickly, confidently, fill her.

“OHHHHHHHHHHHHHHHHH,” she moaned as his cock filled her and she first thought, then said what he wanted to hear more than anything in the world. “Fuck me, Mr. Harris, FUCK ME!”

He did, and excited as he was to feel the inside of a special girl, it did not take him long until he was thrusting hard and deep and panting and fucking and with a grunt, a growl, a yell, he pushed into her with a final, violent, needy thrust and had the most powerful orgasm in his life.

“Oh fuck,” he said pushing his pelvis hard against her, holding, his cum deep in her, “oh fuck, oh fuck, oh fuck.”

That’s all it took for Nikki, for she knew exactly what he was doing, holding in her, knew, somehow, despite never having felt it before, the instant he shot inside her, the instant his cum began to fill her.

Feeling him, feeling a man, feeling Mr. Harris explode inside her sent her over the edge for she too felt an orgasm, a powerful, rumbling orgasm of her own start deep inside her, felt it the instant he came, felt it despite her own penis, her own clit, never being touched.

She felt it, the orgasm, the femininity; she felt it, no longer boy, now only woman.

She felt it as the orgasm washed over her, longer, all over, everything, dizzy, felt it a minute, two, as he held his cock inside her, felt herself become a woman, never, ever, to be a boy again.

*********

Images are from Pantyhose Addict. Obviously Izzy (who owns/runs/poses the site) is NOT transgendered. She's an amazingly beautiful woman who has run an amazing site for a number of years. I only wish I was half as pretty as she is. I HIGHLY suggest joining and seeing all the thousands of pictures she has posted over the years (she has a great blog, too.)

Questions

How long have you thought about it? Days? Months? Years? Decades, even?

When was the first time the forbidden image entered your mind, the first moment you imagined a man inside you?

How did you react, to the realization that fantasizing about a man entering you was thrilling, seductive, sexy, fascinating, titillating?

Have you been confused, all these years, wondering why, when you find women so attractive, when the thought, the reality, of fucking a woman is such a turn on, the vision of a man taking you is something you've masturbated to time and time again.

"But I'm not gay."

Of course you're not. Neither am I.

But still, you think about it, don't you?

Don't lie. Don't lie to me. More importantly, don't lie to yourself.

You still think about dressing up for a man, doing your best to be as feminine as possible, as feminine as he is masculine.

You fall asleep dreaming about it.

You wake up thinking about it.

I know.

Because, as much as I love her, as much as I want to be with her, I dream of the same thing.

I fantasize about the lingerie I'm going to wear.

I dream about the disparity of power, he, so masculine, me, so feminine.

I think about it because I know, I understand, that this is the only way I can be as feminine as I can be.

What will it be like, that first time, beneath him, feeling his taut skin, his muscles, his strength, his body, his power.

What will it feel like, physically, emotionally, when he presses against you, pushes into you, opening you, filling you, for the first time, making you feel and be, a woman.

Role Playing

Friday.

It was a long day. I had to go to a meeting two hours away, first thing in the morning, spent all day at the client's office, drove home, just wanted to have a glass of wine, relax.

It was dark when I got to my house, outside and in, so, as I watched the garage door open, I was surprised to see her car there, I did not expect her to be here. Obviously she was welcome, anytime, given that we both had keys to each others' places, but usually we knew when the other would be there.

I parked the my car in the garage next to hers, walked in.

"Emily," I called out into the semi darkness. No response. I guess she wasn’t here, went out, someone else drove. Maybe she would be back later.

Wine. Then I’d text her.

I walked into the main living area, the open kitchen, dining area, living room, headed for the kitchen first, tossed my keys into the basket on the counter.

Wine. I needed wine.

I opened the wine fridge, took out a bottle, any bottle, did not look, did not care. I opened it, poured a glass, downed it.

"It's about time you got here, I've been waiting for you."

I jumped, her voice, in the darkness, startled me.

“Emily?”

A small light flickered on, I saw a strange woman, sitting in a chair, a smug, impatient look on her face. No, it wasn't a strange woman. It was Emily, but she...her hair was different, curled, dark, rather than her normal straight, blonde hair.

A wig?

"Emily," I asked, still startled.

"You kept me waiting, she said you'd be here an hour ago. I don't like to be kept waiting."

"I..." I looked at her closely now. She was wearing a black halter top evening gown, slit up her left thigh. Her upper legs were pushed together, but her lower legs were apart. Sitting as such, the slit up her left leg exposed her upper thigh, a flash of skin at the top of the nude stockings she was wearing. She held an unlit cigarette in her right hand.

"I...Emily..."

"Emily said you'd be home an hour ago. I don't like to be kept waiting my any man, let alone a little sissy." She put the cigarette to her mouth, inhaled.

"I'm sorry," I apologized, still not quite comprehending what she was doing, where this was going.

"I'm sorry Ma'am or I'm sorry Ms. Irena," she said, tilting her head. "I'd understood from Emily you were better trained, sissy."

"I...I'm sorry Ms. Irena," I managed to mumble, still stunned at the transformation Emily had undertaken, the simple act of donning a wig, a different makeup style, and she was a different person. "I didn't know that, that anyone would be here. I did not expect Emily here tonight."

"No, of course not," she answered, a grin forming on her face. "Not when she's craving a man."

I let out a small gasp, as I always did when the topic arose, when she teased me, when she inferred her need for a man, in a way that left no doubts that she understood my fantasies.

She stood, leaned against the doorway, let the slit in her dress fall around her thigh.

"What? Don't act surprised, sissy, you know a woman needs a man now and then, no matter how much she loves a pretty creature like you. You know Emily needs to dress up, to wear something elegant, like this, and catch a man's eye. You're not that naive, are you?"

"I...no...no, Ma'am."

"Of course not. I know she loves you...Sara...but sometimes a woman needs to feel, well, that she can spend the night flirting with her date, acting innocent, yet knowing the sexual tension that's building, knowing that she's looking across the dinner table at a strong, masculine man, knowing her innocent look is all it takes to seduce him."

I swallowed, put a hand on the counter to balance myself as she mimicked a seductive look.

"You're so funny, Evan," she cooed seductively, using the one name that was sure to fly through me like a bolt of electricity.

"Em...er..."

"You like that, don't you? She's told me all about him, Sara. She's told me things about him even you don't know."

My blush, my humiliation, my inability to even speak did nothing to stop her. Rather, just the opposite, they encouraged her, confirmation that she was pushing the exact right buttons.

"That makes you so jealous, doesn't it, hearing how much he turns her on, in ways you never can?"

"Yes, Ma'am," I admitted.

"You're a sissy?"

"Yes."

"I'll bet she gets nervous, Sara, standing there before Evan, nervous at that very second she's going to start undressing for him. Wondering if he'll find her attractive, wondering if she's pretty enough. I know what goes through her mind, she's told me. I know. I know. I know as she reaches behind her neck to undo the top of her dress, that she thinks about you for one quick second, pauses, but can't stop, not with Evan there watching her."

"She can't stop because as much as she loves you, she wants him, she wants a man, she wants Evan. She wants to feel him, touching her, caressing her. I know how badly she wants him, Sara."

"Did she...has she..."

She laughed, obvious to my internal struggle, the hope it wasn't true, the fantasy that it was. The reality that I wanted it yet hated it so badly that I could not stop thinking about it, hoping it never happened, yet wanting it just the same.

"He just watched her, sissy, watched her lower her top over her breasts, gazing at her thin frame, her hard nipples. He could tell she was nervous and that turned him on like no woman ever had. Wanting her for so long, so close to having her."

Emily/Irena had lowered the top of her dress over her breasts. I was erect now, of course, sticking straight forward, obvious to her.

"A woman gets so nervous the first time she's with a man, but I know Emily, I know how badly she wanted it tonight, how badly she needed it, how she could not stand dreaming about him anymore. Do you want it as badly, Sara?"

I bit my lip, looked down for the first time. "Yes," I whispered.

"I didn't hear you."

"Yes," I responded slightly louder.

"You dream of it, Sara."

"Yes, all the time."

"But do you really want it? Deep inside? Do you?"

"I...I don't know," I admitted. "I think I do, then...I don't know."

She laughed.

"What?"

"The irony?"

"I don't understand."

"Of course not, because she doesn't always confide in you, Sara. It's ironic, that you're so conflicted, like it was up to you, like it was your decision."

"We have not..."

"You honestly think you have not given her permission already? How can you honestly think you can tell her how much you fantasize about her being with a man that she wants in the worst way and that she does anything but infer that she has your permission to fuck him?"

"She hasn't said..."

"You practically begged her to fuck him, Sara! You'll be surprised if she took you up on that? Honestly?"

"I...I don't know."

"Obviously. But I do, Sara, I do. I was with her earlier and we talked all about it."

I had to ask, I had to. "Has she?"

She turned her back to me, started to remove her dress.

"Has she what, sweetie?"

"Has she...has she been with him?"

"Has she been with him?"

"Yes," I said, some urgency in my voice.

She turned to face me again, struck a shy pose, looking as pretty as she ever looked, standing before me in heels, a garter belt, stockings, panties, her dark, curled hair. "I'm sorry, I'm kind of nervous, Evan," she said half seductively, have shyly.

I was shaking.

"You can't stop thinking about it, can you?"

"No Ma'am."

"Do you know how hot that is? A little sissy thinking about his pretty girlfriend fucking a man. Do you know how hot I get when I stand in front of a man, peel off my panties, wanting his cock inside me. Do you think Emily thinks of you when she's standing in Evan's bedroom, seductively pulling down her panties? Of is all that she can think about is how good his cock is going to feel inside her?"

I had both hands on the counter now, the only way I could remain upright. I wanted to drop to the floor, to crawl to her, to worship her.

"Do you think she's doing that right now? Is that why I'm here? To babysit while your precious Emily is with him?"

She laughed. It took me a second to understand why. Hands on the counter to steady myself, I was also pressed against it, my torso touching the edge of the counter, rocking slightly, humping even. I immediately stopped, horrified at what I was doing.

"Oh, don't stop, sissy, I LOVE the irony. You're imagining your dear Emily getting undressed for Evan, you're desperate to know if she fucked him, and your response is to hump the counter!"

"Look at me Sara...look...have you ever gone into her laundry hamper and found a pair of her soiled panties? Picked them up, gently, nervously. Looked at them. Touched them. Smelled them, wondering if there is more there than just her? Hoping, fantasizing."

I was still rocking, slowly, but moving, nevertheless, the pressure of the counter on the front of my trousers, my panties, incredible.

"I asked you a question, sissy."

"Yes," I said.

"Hoping they were filled with cum?"

"Yes, fuck, all the time," I blurted out.

"Licked them?"

"Yes."

"Tasted her?"

"Yes, Ma'am, yes, I...I can't help it."

"Hoping her panties were filled with Evan's cum."

"Yessssss." I started convulsing, shaking, felt it, could not stop it, the wetness spreading in my panties, through my pants. I groaned, shut my eye, fought, gave up, let it happen, did not care, even welcomed her laugh, her throaty, sinister, ironic laugh.

I finally stopped shaking, disgusted, my libido gone, washed away in with the shameful orgasm. I opened my eyes, she was sitting on the chair, her legs curled up, grinning triumphantly at me.

"That's the most disgusting thing I've ever seen," she said, with just enough scorn to feel like a slap, a rebuke.

I took one step back, from the counter, a step towards the bedroom, away from her, away from the shame, the guilt, the horror now flowing through me.

"Where are you going," she asked softly, with the obvious tone that I was to go nowhere.

"Please Em...Ma'am, I...I want to...to clean up."

"You can clean up, Sara. You can get over here on your hands and knees and clean me up...and whatever else you may find inside me."