Showing posts with label masturbation. Show all posts
Showing posts with label masturbation. Show all posts

24 Hours En Femme: a Follow-Up

After I wrote about my day dressed as a woman, I took a long bath in the Jacuzzi tub. I played for a bit with my bathing suits, since I couldn't leave them out of the picture. I modeled each of them in the bathroom mirror, one after the other. It was such a tease, so different from my usual furtive sessions. I settled on the one-piece, which for whatever reason felt the most feminine to me. I tried to draw it out as long as possible, but I came pretty quickly, and very hard. While in the bath, planning my night's escapades, I had decided that I would taste my own jizz, as a way of succumbing to my desire for a feminine experience, so I slurped up some of it, even as the pink fog was lifting. It tasted gamy, not altogether bad, but overall quite gross. It's very hard to remain in the right frame of mind to enjoy it. Nonetheless, I was still excited about sleeping in panties and a nightie. I was fully committed to it.

I had washed some of my lingerie, and had it drying on my towel rack, and it was liberating having all my feminine stuff out in the open. I put on my nightie and panties, and got ready for bed. I had tossed my drab pajamas in the hamper already. As expected, I could hardly help myself from luxuriating in feelings of femininity and reckless abandon. I could take my time, enjoy the idea of remaining in my feminine attire all night, and probably repeat the experience, multiple times.

I eventually dozed off, sleeping uneasily with my tired arousal keeping me in a state of semi-sleep. At some point, the baby woke up crying. He had never seen me in such an outfit, and I had to think about whether to change or not. In the end, I thought it best to just remain in my nightie. I comforted him for a good 30 minutes, rocking him back to sleep while wearing panties and a satiny nightgown! I was a little bit uncomfortable about it. What if he somehow remembers someday? Did he even notice at all? Certainly he rested his head on my bare shoulder, which is usually covered in a t-shirt.

In the morning, I brought myself to climax yet again, and thoroughly exhausted my drive to dress like a woman all day. I had decided to return a couple of things to the store, because I have far too much girlie stuff now to easily conceal. So I ended up not keeping the sports leggings, which I had planned to wear that day. I put them on one last time, and loved how comfy and cozy and sexy they were, and questioned my decision. But in the end, I had to part with them before I ruined them.

I was done for the time being. I cleaned up after myself, the guilt and shame washing over me in anticipation of T__'s return. I was anxious about leaving some trace of my activities. In the end, everything was fine, and she remained oblivious. I was a bit disappointed in my lack of determination to see my plan through, but in the end I came only a couple of hours short. 

Thinking back on it now, I fondly remember pushing the stroller around the neighborhood with girl clothes just under the surface, partly visible, and wish I could do it again soon. I think I might even do it in women's leggings, in public, for all to see, because who even cares? I even put on the dress and tights and shoes last week again during a brief moment alone at home, and thoroughly loved it.

Contemplating a New Swimsuit

My zip-up scuba one-piece
I currently own at least five swimsuits. Four of them are bikinis, and the fifth is a one-piece that zips up in the front. I tend to gravitate to two of the bikinis when I'm in the mood for some femininity, but I've got a soft spot for one-pieces in general, going back to my earliest dalliances in women's clothing.

A lost favorite. (sigh)
Over the years, I've usually had a go-to one-piece swimsuit that I'd wear about as often as my favorite bikinis. For some reason, there's always room for one in my fantasies. Long ago, in my formative years, I had a mind-blowing epiphany upon wearing a one-piece swimsuit, and the memory of it has stuck with me. In early adulthood, when I finally embraced my fetish, I celebrated by wearing a one-piece swimsuit.

Sexy Grommets
Unfortunately, now that I've fooled around with bikinis and lingerie and sexy shoes, one-piece swimsuits often disappoint me. Often, I'll fantasize about one and put it on, but while I'm wearing it I'll inevitably imagine a bikini, and the fantasy will turn to that instead. The one I have now is just not doing it for me, and it never did the way I'd imagined it would when I bought it. Others I've had have not had this problem. I could go back to them over and over again, and rarely slip into a fantasy about something else. It's hard to pin down exactly what it is that makes some of them more fun than others, but I suppose that's true of just about any category of garment I like to play with.
Metallic and Pink...

Therefore, I'm pining for a new one-piece that can fill that hole in my closet.

Not actually a swimsuit
At this point in time, with my limited opportunities to enjoy womanhood first-hand, it strikes me as foolish to do this. At best, I'll only get to wear it once a week, and that's likely to be pre-empted by a bikini or lingerie a lot of the time. So I don't want to spend much money on it, especially if I don't end up liking it. My wife doesn't own one, and even if she did, it's nearly impossible to borrow such things without leaving tell-tale stains.

Loving the ruffles
Looks like fun
Still, part of the fun of this fetish is trawling swimsuit vendors' websites and fantasizing about wearing the ones that catch my eye. I'm partial to blue and pink, and metallic, and unusual cutouts. What I love about one-piece suits is that they're ostensibly not as overtly sexy as bikinis and underwear, but they're still quintessentially feminine. There's no mistaking it for anything a man could ever wear. I used to fantasize that the tight fabric would shape my body into a woman's hourglass figure. With the style these days being quite different, many attractive one-piece suits no longer even cover the waist, but that makes them in many ways even sexier.

Cute cut-outs
It's always hard shopping online for such things, because it's hard to find the right fit. I struggled with the fit of my yellow zip-up one-piece, and actually had to return it for one that fit better. Even in person, I've bought one-piece suits that were far too small. The tightness of a small swimsuit can be fun, but there's a limit where it's just impossible to even put it on. So I might even dare to buy it in person to be sure that it's something I'll enjoy. Or maybe I'll get more than one, and hopefully at least one of them will work out.

Even if it doesn't, I'm such a sissy, buying women's swimsuits for myself!


What Am I Wasting My Time On?

I typically have no more than one day per week to indulge in my fantasies. I can't read sissy blogs or look at pictures of transsexuals when I'm at the office, and when I come home I have to do family stuff. That leaves the one day I work from home: I close the door to my home office, and while my wife runs errands with our toddler, thinking I'm hard at work, I can't help but secretly feed my fetish.

Ideally, if I had ample free time alone as I did when I was single, or if my wife knew and approved of my predilections, I'd be more able to get some writing done. Instead, I have to rush through my favorite sites to find something to wank to, and get it over with quickly before she comes home. I spend the rest of the day going back and forth between actual work and these idle fantasies.

So what exactly do I wank to?

As with most crossdressers, I am keenly interested in beautiful women. I've read about sex addicts who need to see something extreme before they can even come close to climax. I'm the opposite: I can wank to just about any picture if it's of a pretty enough woman. It's what goes on in my head that makes me come.

For example, this is what I jerked to today:

I found this by accident while price-checking some beauty product my wife asked for for Xmas. I've been obsessing over her most of the week. What makes her so unbearably hot is the notion that I could buy that dress, and those boots, and I could become that feminine.

I don't spend as much time as I used to window-shopping lingerie and swimsuits online. I've made all kinds of goo contemplating and even actually purchasing and wearing such things. In the last couple of years, I've found myself drawn to pictures of convincing crossdressers and transsexuals, and of genetic girls given photoshop penises. This all used to repulse me, but now it fills me with admiration, envy, and hope: how incredibly lucky they are to have become feminine! How I wish that could be me!

Commitment

It's hard to find the freedom to fantasize about being a woman at this time of year. All the same, the only way this blog can work is if I commit to posting something regularly. So that's what I'm trying to start now. I'm aiming for at least one post per week. I'll keep mixing fantasy and reality, but everything is clearly labelled, so there should be no confusion.

Meanwhile, I have to use my precious little time wisely. I'm continuing to work on some fantasy stories, but I can't help but spend a lot of it on just looking at dirty pictures and masturbating.

Insatiable

While writing that last post, I mentioned knowing that if I had no boundaries, I would wank myself to death. I thought I had written about this before, but searched for it throughout my writings, to no avail. I wanted to link to the article I thought I had written, as a case in point. But there is no such article. Therefore, here's a little story about my insatiability when it comes to feminizing myself.

One evening, with my wife out of town for a bachelorette party or some such, I had decided to make full use of her absence to engage in as much girlish debauchery as I could handle. There was so much that I wanted to wear, and in only one night, that I hardly knew where to start. I have limited ability to recuperate at my age, so every wank must count.

Usually, when she's not far away, I have limited time to enjoy my femininity. I browse around the web for things that interest me for a while, which normally feeds some specific fantasy. I then fulfill it by wearing whichever girlie item fits the fantasy best. Sometimes, I'm already obsessed with some specific garment, and develop an elaborate fantasy around it. In any case, it's over after one wank, so I prefer my fantasy to match what I'm wearing, to maximize my pleasure. At times, this isn't enough to satisfy me, for various reasons. I actually keep a diary of every "incident", including what I wore, how much I enjoyed it on a scale of 1 to 10, and a brief description of the circumstances. Merely documenting this after the fact often launches me into another fantasy, so I find myself wanking again in another garment. This second orgasm is usually much harder to achieve. Interestingly, when making love to my wife, I can never muster the lust to come twice.

On this particular evening, I knew that I had all night. I was ravenous for femininity. I had a plan. Since I had no fear of interference, and total privacy for many, many hours, I decided that I would spend the evening wearing nothing but women's clothes, and sleep in my wife's little slip dress that she left behind under her pillow. I had fantasized many times about doing this, but inevitably my playtime would end after succumbing to the temptation of orgasm. This time, I was determined to at least see how long I could go, and try to avoid masturbating.

I whet my appetite browsing the web for the usual: pictures, stories, captions, videos, and so on. I probably wore swimwear while doing so (my records are sketchy, so I'm not sure). I tried to hold out, but probably lasted only an hour or so. In spite of my ambitions, I achieved my first climax quite quickly after all that preparation. In fact, it was too quick to be fully satisfactory. Thinking of my original plan, rather than giving up right then and there, I changed into a bikini. The thought of actually executing on my plan was so arousing that I couldn't resist coming again, soon after putting it on.

By now, I was already tired. My penis was sore from having climaxed twice. With resignation, I cleaned up the mess, and thought my valiant attempt had no hope of continuing. But there again was that thought: now that I've gotten it out of my system, I can surely wear women's clothes without having to masturbate. This would be somewhat less fun, but satisfying nonetheless, on an entirely different level. I slipped into my corset, stockings and high black boots, figuring that if I was going to do this, I might as well challenge myself.

I settled onto the sofa in my lingerie to watch a movie. I spoke to my wife on the phone. The whole time, I counted my blessings that I could wear such an outfit. I lounged happily in my feminine attire, fondling the lace of my panties and the smooth nylon of my stockings, snapping my garters, and adjusting my bodice. Before long, and much to my delight, I gave in to temptation yet again.

At this point, I would normally start feeling a little ill from all the strain, and more than a little over-satiated. And so it was then. But I had a seed in my head. I felt like I could go no further, but by now I was wondering if I even could cum if I tried. I struggled a bit to think of what I'd want to wear, but the very idea of being such a sissy that I could still climax after everything I had already done, spurred me on. I chose my favorite swimsuit, and carried on, knowing that I still had to somehow sleep wearing panties and a nightie.

It was less difficult than I had thought. It was somewhat painful, as with an overworked muscle, and it hurt to even have an erection, but the overload of femininity was too much to keep me from succeeding. I came again!

It was late by now, and I was exhausted. I felt like there was no amount of masturbation that would cure me of this fetish. All I had to do was allow myself to fantasize, and I could keep cumming over and over again. The idea that this dirty little fetish was impossible to satisfy made me want to come yet again! Somewhat unnerved, I slipped into the nightie and panties as planned, brushed my teeth, and went to bed, excited about sleeping en femme. I was drifting off to sleep, and just wanted to enjoy some sweet girlish dreams. I tried not to think about what I was doing.

It was no use. I woke up in the middle of the night with a massive erection, throbbing with the dull pain of muscular fatigue. I would not be able to sleep until I wanked it out, so I once again satisfied my urges.

By now there was no longer any doubt. I had discovered that there is no practical limit to my arousal when indulging my feminine fantasies. I could literally wank myself to death if I allowed myself to. It was also both arousing and disconcerting to confirm that my ample appetite for straight heterosexual intercourse was far smaller than that for feminization. This was not surprising. That the latter was limitless, was.

By morning, I was so worn out and so sore that I couldn't imagine how I would explain to my wife why I wasn't eager to fuck her when she returned. I schlepped around all day in a fog from my exertions of the night before. I had only now, after all these years, discovered the magnitude of my problem.

What Could Have Been


Often when I make myself feminine, I think back to some decisions I made years ago, and how different my life might have been had I done things differently.

I had been sharing the rent on a house with a co-worker some years ago, and secretly prancing around in all sorts of lingerie and swimwear. He had no idea. Still, I felt frustrated by my lack of freedom to express my feminine side all throughout the house. When he was out of town, I would take advantage of the opportunity without any fear of discovery. When the time came to move out, I decided that I would get a one-bedroom apartment and live alone, just to allow me the pleasure of living in girlwear whenever I wanted. I imagined ordering lingerie for delivery to my front door on a regular basis, with hardly any risk of discovery.

Pretty much as soon as I moved in, I met a girl, and she was coming over all the time, and we were having sex so often that I could hardly keep up. This naturally left me with very few opportunities to dress up. This same girl is now my wife, and the mother of my child.

The sissy thing to have done would have been to either get rid of her or involve her in my fetish for women's swimwear and lingerie, rather than keeping it secret. She might have stuck around if I had told her or shown her, but it doesn't matter: the point would have been to choose femininity over masculinity.

My garter slip
Today, while she was out, I risked wearing my garter slip, stockings, and shoes, for the first time since she almost caught me. While I luxuriated in the tight, soft fabric, I fantasized about how if not for her, I could have chosen a very different path. I imagine myself wearing lingerie every day in that old apartment, expanding my collection of panties and bras and bikinis and shoes and skirts and dresses. I would have masturbated ecstatically in a garter slip like this one, only instead of quickly cleaning up, hiding my girlish garments, and immediately getting back into my male clothes, I would have cleaned up and immediately put on some simple satiny everyday panties and gone on with my day. I know that if I had no boundaries, I could happily wank myself to death, never tiring of the femininity of it all. Eventually, I would have come out of the closet, so to speak, and become proudly transsexual.

These thoughts brought me to a quick but satisfying climax. And it's not the first time. Even now, as I retell it, I'm getting horny again.

Alas, it was not to be. And yet, I still think I made the right choice. I wouldn't give up my "normal" life, with my loving wife and beautiful baby, even for that. But I can still have fun now and then, pondering how it might have been.

Fantasy: Litérature Vérité

The fantasy had taken hold, and wouldn't let go.  It was the usual scenarios, all mixed together.  I was refining the back story over and over again, getting more and more excited as I circled around the denouement, coming closer and closer each time, from different angles. 

I was captured by a bunch of evil girls who were forcing me to wear a bikini... or a one-piece swimsuit... or they had captured me long ago, and forced me to wear all kinds of other things, trying to feminize me, but I was resisting... Yes... but by now, I knew that I was close to my breaking point... No, I was well past my breaking point, and they had me right where they wanted: begging them to wear a one-piece bathing suit... Yes, I beg them, but they refuse... I've worn so much other stuff by now, over the course of my captivity, that I've even begun to turn girlish, but they never let me wear a bathing suit... Yes, and I absolutely must wear it, I'm obsessed with it... They know that I'm not ready for it, that it will utterly destroy what's left of my manhood, and they want to drag this on forever... Or maybe they know that it will set back my feminization, while I want desperately, but secretly, to accelerate it... yes, it's a trick: they want me to prove just how badly I want to be a girl, so they contrive to have me steal it...

My fantasy settles on the one-piece swimsuit.  I shake loose of my reverie just enough to consciously reach my secret spot, between my bed and the wall, for my stash of girlie things.  I rummage around, and pause after touching each item, trying to guess in the dark what I'm fondling, each time considering for a moment whether or not I'd rather wear that instead, and alter my fantasy accordingly.

Hmmm, my black bustier... lingerie is always fun, but I really can't get that image of Heidi Klum in her swimsuit out of my mind.  I want to feel like that... How about my pink string bikini?  That's pretty fun.  But not as fun, oddly enough, as my silver bikini... oh, how I love the bra on that one... but no, the fantasy is about a one-piece.  Yeah, that's right... I don't like these little cotton panties... ah, here it is!

I pull it out as quietly as possible, and put it down under the sheets beside me.  I strip out of my shorts, thinking for a moment of keeping my shirt on.  There's always something sexy about having girlie stuff on under my boy clothes, like it's an admission that I might look like a man on the outside, but on the inside, I'm utterly feminine.  But even stronger is the idea of abandoning all connection to male attire, and succumbing completely to women's.  I pull off my shirt, and remain naked for no longer than it takes to figure out where the front of my bathing suit is.  I'm such a sissy that I can expertly get dressed in women's underthings in the dark.  The suit slides into place, and I slip my arms into the straps.  I adjust the suit so that it sits right on my body.  I tweak my nipple briefly, fantasizing about the cups of my swimsuit being properly filled.  I let the mist of my imagination thicken back around me, and delve headlong back into my fantasy.

I'm still reworking the back story, although now I'm at the climax.  I'm wearing a one-piece suit, and it's outrageously feminine, and I'm resisting letting it overtake me too fast.  I'm on my stomach now, gently humping my balled-up shorts, savouring every long stroke.  As I fondle my hips and my waist, I imagine myself standing up, in my fantasy scenario, wearing a swimsuit, looking every bit as feminine as Heidi Klum, fondling myself exactly as I am in my bed.  The soft, tight, feminine fabric rubs and stretches on my enormous cock.  In my mind, my cock shrinks away to nothingness, as I fully and wilfully succumb to irresistible womanhood.  My captors catch me red-handed, and I show them how proud I am of defying them.  No, wait... the fantasy shifts again... I am not caught, but I am secretly far more effeminated than they know.  I am in a store full of women's swimwear and lingerie, and I strut around in my new body, scouting out what I'm going to wear next.  What could I possibly wear that could top this in feminine sexiness?  My mind drifts to lingerie, and I imagine myself selecting a nice pair of lacy bikini panties and a matching bra, trying them on...

My cock rubs vigorously against my balled-up shorts.  It's ecstasy.  I'm wearing a women's one-piece swimsuit, very high-cut and tight, and I become conscious that I'm already looking forward to wearing something even sexier.  I'm such a fucking sissy!  I love it!  This realization amplifies my pleasure tenfold.  I'm longing for sexy lingerie that I don't even possess!  My massive erect penis, awash in extraordinary pleasure, is somehow blotted out in my mind, replaced by a soft, fleshy cunt.  Flashes of fucking cross my mind, and I am the girl!  I rub harder and harder, treading dangerously close to the point of no return.  I don't want to come!  I want this to go on forever!  I imagine myself a slutty little bitch, fucking and sucking cock, and loving every second of it!  Every time I come close to coming, I slow down, break the rhythm just enough, and continue.

At last, I can no longer resist the lure of such massive pleasure, and I pass the point of no return.  I do this consciously, and my fantasy dissolves a bit as I prepare for the imminent mess.  The pleasure is phenomenal.  It takes my breath away.  My hand darts into the suit through one of the leg holes, and I cup it next to my dick's head, and pump a huge quantity of semen into it, to the point of overflowing.  My legs shake with the intensity of it.  The remaining mist of fantasy quickly disperses, and I find myself short of breath on my stomach, wearing a smelly blue girlie swimsuit, with a huge mess of giz in my hand, afraid to move for fear of spilling it all over my bedsheets.  I have to be careful as I roll onto my back, and keep the swimsuit from touching the goo on my belly.

I reach for the nearby box of kleenex with my left hand.  This is very tricky.  Over time, it's inevitable: a growing yellowish stain grows on the belly of my swimsuit.  I used to come right into it, heedless of the mess I made.  But now I realize that I need to be more discreet, and more respectful of these wonderful items of clothing.  They are like magical relics, which I must be careful to avoid defiling with my disgusting manhood.  They are pristine vessels of femininity.  Meanwhile, I carefully slide out of my swimsuit, after wiping as much away as I could from my right hand and belly.  At some point I have no choice but to allow the swimsuit to touch a bit of semen.  I clean the rest of the mess, put my shorts back on, and tuck the object of my sin back into its hiding place, a little bit ashamed and disgusted with myself, yet luxuriating in afterglow, the fantasy fulfilled as best as I can.

If I really spent some time developing my fantasy, I sometimes find myself fantasizing about how girlish and sissy I've been, and find myself doing it all over again, usually with some other article of clothing, only with not nearly as much pleasure.  Then I fall asleep exhausted.

This is Becoming a Habit

 I'm on another business trip, and as is becoming usual, I bought myself some nail polish and makeup. I bought a cheap makeup box on Ama...