Sexual Sissy Awakening

Summary: Man turns into a sissy with help from online author.

Note 1: Dedicated to Brittany, who suggested this sissy exploration tale.

Note 2: Thanks to Tex Beethoven and Robert for editing this story.

Sexual Sissy Awakening

I thank silkstockingslover. 100%. Okay, well not a hundred percent, that would be ridiculous. But her influence was huge.

Many of her stories seemed to be about everything I was feeling. Not the lesbian or group sex ones of course, but the ones about men rediscovering themselves, absolutely!

It was like she'd been inside my head when she wrote them.

She'd helped me come to grips with many of my insecurities.

If her stories were true... or even partly true... then I wasn't alone in my desire to dress up in feminine clothing. I wasn't alone in being curious about sucking a cock. I wasn't alone in having a mid-life crisis at 52.

If her stories were true, not only did many men have sexual awakenings in their late 30s to early 50s, but many men my age were curious about becoming feminized, about sucking cock, and perhaps even about bottoming.

But I can't thank only her. I can also thank those hypno sissy videos, since they became completely inspirational for me. But those too I could thank her for, since I never knew they existed until I read her HypnoSissy series, and well, a whole new world was suddenly staring back at me.

No, I really can't thank only her. I mean it was my own desperate idea to email her in the first place. But then it was her gracious decision to respond.

Am I being confusing? Okay then, here's the story of my exploration of my feminine side.

Which really shifted from just jerking off, to hypno sissy and shemale porn, to my becoming a complete slut for cock... something Emma, my wife of twenty-nine years still didn't know when I first emailed silkstockingslover.

When I did it, I wasn't expecting a reply. And I certainly wasn't expecting to receive her advice. It was just a safe way of getting some things off my chest.

Dear silkstockingslover

I have been reading your stories, and I just have to finally write and thank you. I have always voted five stars for the stories I enjoyed, which was almost all of them, and even left the odd comment as Anonymous, and yet finally after reading a couple stories that really hit home, I have to finally open up and write.

You have changed my life, or at least you have changed the trajectory of my sex life.

Although I'd love for you to respond, I understand you likely get a lot of fan mail, but I just have to finally tell you how great you are, and to repeat that you have completely changed me as a man, and helped me begin to come to grips with many feelings I have kept inside for years, but that had grown stronger and tougher to ignore as I hit my forties.

Thanks. Bradshaw

I pressed Send, and felt relieved. I hadn't actually said much, only vaguely hinted at my sissy curiosity... something I'd never told anyone before. I mean who would you tell?

Not your friends.

Definitely not your wife.

Literally, no one.

I didn't expect a response, so I was quite surprised when a day later there was an email in my inbox from her.

I was at work. I'm an executive VP of a small computer firm. Yes, I'm a little geeky, although I was otherwise the epitome of average.

Yet I had to read her response.

Hi Bradshaw,

Thanks for the email.

Which stories in particular do you like the most? What exactly do you mean by I have changed the trajectory of your sex life? I'm flattered, but curious what that means.

I have a new story out every week or so, and I hope you vote five stars for the ones you like and leave the odd comment. Authors love to get emails like yours, and comments about our stories.

Why don't you tell me a bit about yourself?

Jasmine

See what I mean? She didn't have to start asking me questions, unless she intended to assist me with my journey. So of course even though I should have been prepping for a meeting, I couldn't help but respond immediately.

Jasmine (if I may call you that -- I mean by your first name instead of more formally),

I'm flattered you took the time to respond.

I'm 52. Married. Work in computers. Six feet tall, 185 pounds, in pretty good shape, and the beginning of grey hair hinting that I really am now in my fifties. But I am still decent looking and sometimes get looks from the ladies. Maybe that is more information than you were requesting.

I enjoy almost all your stories. I have loved nylons for as long as I can remember. When I was in high school in the eighties, the lady teachers, cheerleaders and many of my peers wore them all the time. My mom was a nurse back in the time when white pantyhose were still part of their uniform.

I binge read all your incest stories first... I've always liked the taboo aspect of it. I also read all your lesbian and illustrated ones. Eventually I have read your entire catalogue, even the gay ones, and those are the ones that began my new trajectory.

The one that really started it for me was the first story in the Kinky Tales series. The idea of a woman wearing a strap-on and fucking her husband was strangely hot. I mean, I had never even remotely thought about that, nor was I at all interested in getting ass fucked, yet over the next few weeks I kept going back to that series over and over.

That led to my researching pegging, discovering it wasn't as rare as I had assumed, and I began watching a lot of pegging porn. Although I had a problem with it, because most it went straight to the sucking and fucking, without much of a plot, if any. And for me at least, I needed a plot. How did the outrageously masculine quarterback end up getting bent over and fucked by a cheerleader? Or how did the stepson end up begging to get ass fucked by his stepmom while his girlfriend watched? Or how did the tattooed stud end up bent over a pool table while being sodomized (a word you often use, which I find so hot) by a chubby waitress?

Anyway, this led to more, but I've probably already gone on longer than you would want to read.

However if you do want to hear more, I'd love to share more.

Writing this down feels surprisingly therapeutic.

Bradshaw

I clicked Send and went back to work with a major hard-on, hoping she would respond. If her stories were more than just fiction, and all the psychological aspects did appear to be well researched, then I wasn't alone in my curiosity, and maybe she would not only understand, but help me to explore my growing obsession with becoming feminized.

She hadn't responded two days later, so I assumed I had turned her off.

It was Friday afternoon, near the end of the day, as I was winding down from an intense day at work, and believe it or not, there can be some intense crises at my job, especially when a major client is hacked.

So I was thrilled to see an email from Jasmine had arrived an hour ago.

I sat back in my chair and clicked it open.

Bradshaw

Of course you may call me Jasmine. But you may also call me Mistress, since it is pretty obvious you are looking for guidance.

Just so you know, you are not alone. Many men your age begin to question their sexuality. Whether it is pegging that attracts them, which is becoming more and more commonplace each year; or sucking cock, which a shocking amount of men your age fantasize about doing (or actually do); or becoming a bottom for cock, often big black cock; there is nothing about any of those practices to be ashamed of.

And I know almost for sure you have felt guilt, confusion, and likely a plethora of other feelings.

These are all perfectly natural.

So if you have more questions, or need to share or vent, feel free to drop me another line whenever you like.

Have you been pegged yet?

Jasmine

Her words were magical!

They were exactly what I needed.

Someone who understood.

Someone who wouldn't judge.

Someone with whom I could share my inner truths without condemnation or risk.

Yes I had felt all those feelings she listed, and she had called them natural!

I responded.

Mistress Jasmine (I love the look of those two words together),

Thank you for your response and your understanding. Everything you said is true. The past two years have been so confusing, as I questioned my manhood and my masculinity. I mean can I be the man of the house and still want to be pegged? Or maybe want to suck a cock? I haven't known.

No, I have never been pegged. I love my wife Emma, but our sex life has diminished substantially over the years, which, I suppose, happens to most couples. I don't think she would understand any of my feelings. About being pegged. Sucking cock. Wearing women's clothes. Getting fucked.

Just writing them down is both liberating and humiliating.

I should note that after reading your pegging stories, I then read all your shemale stories, as the idea of sucking a cock attached to a woman made it seem less gay. Same with the idea of getting fucked. If I got fucked by a curvy woman who happened to have a real cock, that seemed less shameful.

But then I read your HypnoSissy series, and that fucked me over completely!

I had no idea men like that existed, but once I read the series, I had to find some examples, and well, by now I have watched every one on Pornhub, and other sites I could find.

Having women calling me names and telling me what to do, was somehow the ultimate turn on.

This, of course, has led me to my becoming obsessed with being feminized, sucking cock and getting fucked.

But of course fantasy and reality are two very, very different things. I haven't actually done any of those things.

Thanks for letting me vent. It has felt very liberating to get two years of guilt and confusion off my chest.

Brittany

I clicked Send, I made sure my office door was locked, sat down on my desk and jerked off... I didn't last three minutes.

Unfortunately, she didn't respond right away, so I headed home.

I checked my email every few minutes all night until I finally fell asleep, and alas, nothing.

As soon as I woke up, I saw there was one from her.

Brittany (by the way, an interesting name choice, and from experience and years of teaching, most Brittanys are hot and slutty),

If I may be blunt, I have chatted with many men like yourself. You have three paths to choose between.

1. Ignore these growing feelings, although they will likely continue to consume you and make you unhappy, and potentially you might even start feeling bitter towards your oblivious wife.

2. Tell Emma what you're feeling. Of course this could go a number of ways, and you know her better than I do. But I can honestly tell you that women are more open minded than most men assume, and many of us have our own kinky secrets and fantasies we're hiding (such as an author with a hidden identity, who in real life secretly wants to eat student pussy, to get fucked by a BBC, and to share an incestuous threesome with her sisters, for example).

3. Explore these feelings secretly.

But I need to stress that Option 1 is futile, which I know from my experience in corresponding with other men just like you (and there are so many of you)! Once the idea has been triggered, there is no pushing it away. Pandora's Box has been opened, the Genie is out of the bottle, or whatever metaphor you care to use.

I know it's scary.

I know you're confused.

But from your own words... you are becoming more and more consumed by these feelings, and thus they will continue to control your mind, body and soul, until you have satisfied this curiosity.

Jasmine

I read her response a dozen times.

Yes, it was scary.

Yes, I was confused.

Yet I was also beginning, through her words, to accept my growing curiosity and desire. It was indeed consuming me, and I assumed she was right... that until I dealt with it one way or another, it would continue to burn inside me.

While Emma was in the shower, I responded,

Jasmine

Thank you so much!

I know I can't choose option 1.

I also know I can't choose option 2. I mean I could, but I'm scared of the worst-case scenario, which I think is the only likely one.

And as for option 3... where would I even begin?

I hate to ask for even more of your guidance, as I'm sure you have better things to do than help some man explore whether he is a sissy or not, but could you give me some advice?

I literally am ready to go ahead with number three... but where do I start?

Pet Brittany

I clicked Send, just as my wife walked out of the shower.

"I see you're hard already," she said, as my dick bulged in my boxers.

"Yeah, I'm thinking we should do something about that," I agreed, tossing the phone onto the bed and walking over to her.

"I just showered," she objected.

"I prefer you getting a little dirty," I smiled, as I leaned in to kiss her.

"Not now," she refused, backing away.

I sighed.

"Don't sigh at me," she said. "You want sex after I shower while I have to get ready for work."

I replied, like I always seemed to do, "Sorry."

"We can definitely have sex," she said. "But we need to plan it."

"Yeah, nothing is sexier than fucking on a schedule," I joked, the raw passion where we'd fucked like bunnies long gone, or when we'd fucked anywhere. Shit, the first time I fucked her was in a girl's bathroom at her sister's wedding.

"Sorry, you know I prefer to plan things," she said as she escaped over to her dresser.

"We didn't plan the time you sucked me under the table at Walter's, or when I fucked you in your boss's office at the Christmas party," I tried to remind her of her younger, wilder, more spontaneous days.

"I was twenty then, not forty-five with kids."

"I know," I said, thinking if I was ever going to tell her what I'd been feeling, this would be the time. Yet I didn't. "It's just we...." I paused.

"It's just we what?" she asked, in a tone that warned whatever I said next might blow up in my face.

"Nothing."

"No, tell me," she said, as she put her panties on. Panties that weren't remotely sexy.

"It's just, we don't really connect like we used to," I said cautiously.

"Connect?" she asked. "You mean fuck?"

"Not just fuck, but experience moments when we simply have to have each other."

This seemed to soften her. "Yeah, I suppose that's true."

"It's no one's fault. Life got busy." I said.

"Well," she said, as she grabbed a pair of pantyhose, she used to wear thigh highs, or garter-belts and stockings, but now it was always pantyhose. "Let's plan a night."

"Okay," I said, as she sat on the bed.

She said, seeing me watching her. "Maybe I'll even go buy some thigh highs."

"Please do."

"You and your nylon fetish."

"That's why I married a woman who works in politics," I joked.

"And because I used to suck your dick every day," she said, now sounding like my wife in her younger days.

"And swallowed," I added.

"And gave you foot jobs," she added.

"And sat on my face," I continued.

"Fuck, you're getting me horny now," she sighed, as she finished putting her pantyhose on.

"Well, you could go in late," I said.

"I have a meeting with the mayor at nine," she said. "I can't be late."

"Fine," I said.

"But if you can shoot your load quickly, I can give you a quick BJ," she said, as she knelt before me.

"You know I never last long in your mouth," I said, as she pulled down my boxers.

"Well, just come down my throat, she said. "I haven't taken the time for breakfast yet anyway."

As she began sucking my dick for the first time in months, I joked, "Well, that is the most important meal of the day."

Three minutes later, she was standing up after having swallowed my load. "I do love cum."

"Well, I'll always have a fresh load ready for you," I smiled.

"I'll keep that in mind," as she kissed me and went into the walk-in closet to finish getting dressed.

I hopped into the shower, suddenly feeling so guilty for emailing Jasmine, and for even considering exploring my sissy curiosity.

I loved Emma. So either I'd tell her, or I'd do nothing.

That was my new resolve.

Which, of course, lasted only for about four hours.

When I couldn't help but check whether Jasmine had responded.

She had.

Then I couldn't help but read it... because even after that special moment with my wife, my curiosity was still there, and my desire to be feminized was still strong.

Pet Brittany,

What's next is simple.

You start by doing small tasks.

For example, here is task 1. Go out right now, buy a pair of pantyhose, and put them on underneath your work clothes.

Simple.

Baby steps.

Mistress Jasmine

She'd used the term Mistress.

She'd given me an order.

It was almost lunchtime.

What the fuck!

Why not?

I had always wondered what wearing pantyhose would be like, and had always thought it was unfair that for some reason they were considered a women only clothing accessory.

I headed out for lunch, grabbed a sandwich, and bought a pair of black nylons from a department store. It was kind of awkward to purchase pantyhose, although the saleswoman didn't seem too fazed.

I got back to work, locked my office door and pulled on the pantyhose... which I discovered was a lot more work than I had imagined. Watching a woman put them on had always been sexy, I had watched many scenes on YouTube, but actually doing it, was a bit of work and awkward.

Once on, I put my socks back on, pulled up my pants and walked around. It felt slightly weird, yet super exciting.

I sat down at my desk and checked my Inbox to see if there was another email from Jasmine... and one had arrived just three minutes ago.

Of course I clicked on it.

Pet Brittany,

If I am right, and I usually am, you went out almost immediately, bought some nylons, and you're now wearing them.

If that's true, which I'm confident it is, I want you to slide your pants down, and just rub your hands over your nylon legs.

How does it feel? Does it make your cock hard?

But don't touch that dick of yours.

When you're in nylons... you must allow your feminine side to take charge.

You are sexy.

You are sensual.

You are BRITTANY.

You don't have a dick... you have a pussy.

Mistress Jasmine

Wow!

Her words were as magical here as they were in her stories... even more so, since they were directed at me personally.