Posted on December 3, 2014 by Sheery — 12 Comments

Obsession Crotchless Teddy

In my usual stroll through online lingerie stores, I almost never see anything that really gets my my eye these days. More often than not, it’s the same strap teddy or babydoll with “peekaboo” holes for nipples to stick out. Yet, being so picky, I’m always on the lookout for that sexy something that won’t end up a wadded wrinkled ball sitting in a bag ten years later.

Indeed I found it, something I always overlooked and definitely unappreciated. So now I present… crotchless lingerie.

I purchased an Obsession Diamond Teddy in black on eBay and, true to its name, I’ve been obsessed with it ever since it landed in my horny little hands. Immediately, I slipped on some Oroblu Magie pantyhose then into this beauty which, not only fit perfectly, but looks incredible on me if I say so myself.

I love the ingenious way the teddy uses adjustable elastic leg loops to permit a wide open crotch area. I mean we’re talking front all the way up the ass crack. As my cock starts to bulge through the pantyhose (instead of hanging in open air), I wouldn’t find this typically feminine or appealing. Yet there is a cute little jeweled embellishment that hangs down gently over the bulge giving an appeal to the “present” underneath. I kind of like it actually and think I’ll call it the femme package.

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Posted on November 22, 2014 by Sheery — 3 Comments

Sheery in a camisole and pantyhose

Usually when I post here, I’m very much “in the mood.” That is, not just dressing the part but living up to it so to speak. It is usually morning time, I’ve had my cup of coffee and am in my cute satin robe that just barely covers my ass. Of course, I have on silky pantyhose, high heels and, to feel extra sassy, throw on some lipstick (now a regular thing).

While it is a major turn-on to see my silken self shine, I’ve embraced my feminine role enough now to go beyond the usual crossdresser frolicking and into a realm which hasn’t been penetrated to the full extent yet (excuse the pun).

Namely, I can’t stop thinking about that feminized penis that wants to violate me and make me believe I’m a true woman.

Maybe five or six years ago, the thought sex with another crossdresser would have never even crossed my mind. I was a happy-go-lucky crossdresser content with throwing on a pair of nice pantyhose with a cheap bra and panties, wank it then call it a day. You know, the typical practice during the some twenty years prior.  Then one day something dawned on me, or you can say the little girl in me was starting to bloom.

It feels quite sexy to look like a woman in her skimpies and admire it in a mirror but what would it be like to feel and take pleasure like one? Rolling around in nylon and lace isn’t quite the same so there I was one day, laying in bed (lingerie, hose and all) getting into various positions and pretending I was on the receiving end of a good pelvic clapping. The fact that it made me question my, at that time, heterosexual self (I’m not gay, am I?) actually made it even more alluring.

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Posted on November 8, 2014 by Sheery — 2 Comments
Pantyhose over face
Image: Wormed of Horrors

Sure, we as crossdressers like to have our fun and our whole motto could arguably be summed up as “we do whatever the fuck we want, dressed as women.” While we surely do not live by a behavior code (or any kind of code, really), there are some things, however, we might want to pay some mind to. As in please, for the sake of our beloved crossdressing community, cut this shit out.

So without further ado, I present ten things crossdressers need to stop doing right this second.

10. Using the terms “passable,” “lesbian,” “slut” or “whore” to describe ourselves unless, of course, a vagina was recently installed.

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Posted on October 18, 2014 by Sheery — 2 Comments

Sheery in Capezio Stirrup Tights

Out of the thousands and thousands of times of slipping into pantyhose, I’m talking since the pre-pubescent pantyhose fetish years, there is one thing I have never gotten tired of. Of course, there is the usual nylon hugging my bulging wannabe female parts giving me the jollies but I also can’t get enough of looking down and wiggling my toes pretending they are struggling in in their silken trap.

Despite the love of encased toes, I’ve never been very foot fetishy which is why I primarily like my pantyhose footed. That and because I’m so un-ladylike when it comes to caring for my feet. Toe cheese, nails that can rival an eagle’s talons and whatever that black shit is that had been stuck for a week could all use a bit of attention (and an army of pedicurists).

Well, obviously that had to change so, first, there was the self-pedicure that took at least a couple of hours. Next, trimming those little hairs on my big toe (weird) and, last but not least, a little fuscia polish to beauty them up. Was that so hard? I said to myself trying to convince myself I’m a REAL girl.

Then giddy with my pretty feet, it was time to rip into that new package of Capezio Ultra Shimmery stirrup tights in color Toast. I never thought I’d see the day where I’m wearing pantyhose (tights in this case) with my painted toes exposed and feeling even more feminine sexy than ever.

At this moment, I never wanted go back to footed pantyhose… and had to seriously masturbate looking at my new beautiful toes, free to breathe in the daylight.

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Posted on September 29, 2014 by Sheery — 8 Comments
Squirt From The Hose
Image: terwilliger911 (Flickr)

Some of you out there may have, at one time or another (or always), dreamed about meeting that perfect girl crossdresser. You know, she show up beautifully made up, slinky dress, expensive pantyhose and heels and smells like a flower blooming after a rainy day in Italy. Then maybe after a little wining and dining, she takes you into your bedroom and proceeds to spank and pound your ass flat and tender.

Mind that this is only after you first get a taste slurping her girl cock until she tells you when. If you’re lucky enough, maybe leaving a generous tip in your mouth and down your throat.

If you unfortunately find this absolutely disgusting or appalling, cover your eyes, find your mommy and I’ll give you the opportunity to leave now.

Great, still here?

Have you ever had an attraction to other crossdressers whether it be in admiration, willing to go the distance with a passionate foray or been there, done that? Well, for those “bi-curious” waiting for the experience no different than a teeny-bopper anxiously anticipating getting her cherry popped, I believe I came upon (quite literally) a foolproof way to determine if you’re ready or not.

Ready?

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Posted on September 10, 2014 by Sheery — 4 Comments
Conchita Wurst
Image: VIPevents

Unfortunately, I’m in one of those negative moods today. Enough so to make me hate everything… well almost. Slipping into some Wolford tights, however, just isn’t the same, seemingly lacking in joy of digging into my femme side to ease the bad vibes. I don’t think new heels could even cure my case of get the hell away from me today.

So, in honor of negative bullshit, I feel it is my duty to call out on the seven things I really hate as a crossdresser, not in any particular order. They all pretty much suck, er, I mean can go suck.

1. Hair, That Which is Not on Thy Head

Have you ever shaved all of your body hair? It is a fucking tedious process that takes a minimum of two hours. And don’t get me started if the Remington isn’t fully charged. Afterwards, though, is a bliss of silky smooth delight, sliding around on your sheets and your pantyhose not having to hold back the wild forage overgrowing your crotch.

Then a week later, back to hairy and hours trimming. Maybe this time, I’ll remember to charge the damn shaver.

We’re not even talking about the beard either. Not even Estee Lauder can hide that 5 o’ clock shadow when you doll yourself up. Oddly enough, some other Eurovision winning singers can pull it off with class. Just don’t let this become a trend though.

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Posted on August 31, 2014 by Sheery — 4 Comments

Crossdresser Sheery

Admit it. There have been days where you have looked back to see where your silky little fetishes began. “Stealing” your mother’s panties and/or pantyhose (shame on you) and getting high off of the shame that comes with inappropriately wearing garments of the opposite sex.

Yet, didn’t it all start innocently enough just happening to try on that bra or slip into those pantyhose just to see what it was like? Or even as a joke? Who are we kidding, you don’t just start a fetish. They develop as we experiment as little youngsters and notice our little cocks get off when we keep doing them. Oooh, dressing in my mom’s lingerie turns me on and I don’t know why the fuck that is, but I like it!

Surely, back then, you never even heard of the word fetish or knew that this would turn into a lifelong compulsion. For me, personally during my teenage years, I thought I could “turn off” my crossdressing since I could see it being an inconvenience when dating girls as I went off to college. I did, in fact, turn it off for about six weeks only to return to crossdressing with an extreme vigor. This happen to coincide with receiving a Victoria’s Secret catalog and my first credit card then buying exactly what Stephanie Seymour was modeling on page 20.

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Posted on August 18, 2014 by Sheery — No Comments
Femskin Catsuit
Image: Femskin

I’ll be honest. I have never really dived into the world of complete transformation beyond using the typical makeup, wig and a padded bra. OK, maybe I’ll go for a padded panty, too, but that’s about as far as it goes. I prefer to take the purist approach to crossdressing which is not doing what a vagina-possessing woman wouldn’t do herself.

(Wild acts of varying degrees and screams while crossdressed not included of course)

That’s not to say I haven’t looked around at online shops at all the wonderful transformation items available, besides your standard wig. Breast forms, masks, gaffs, all things that can turn the ugly man-shaped body into a sleeker, feminine fantasy version to die for. Alright, maybe not to die for… more like a half man, half-freaky woman. But getting there is half the fun, right?

Yet I came across something I’ve never seen or heard of before. Something that combines everything into one and can actually give you a shape, shall I dare say it, halfway passable. I had to look further into this thing they call the Femskin.

Upon the first image of it I saw, it seemed quite interesting with a very realistic shape to it, assuming it was modeled on a crossdressing man, of course. Aside from the subtle shine it gives off that gives away an artificial rubbery look, it is quite fascinating in that it stays true to every last detail of the female anatomy. You have to do a double-take and/or start groping around to realize it is a body form.

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Posted on July 5, 2014 by Sheery — 7 Comments

Setificato 40 Pantyhose

I have finally come to the realization that in my quest to try every available pantyhose that looks super sexy in an ad, or on a model in a pantyhose fetish site, I’m really just trying see if my beloved Wolford Neon 40 can be outdone. In the meantime, my collection has filled up a gigantic box and many have been rendered as stylish cleaning rags.

Yet this time, I came close in the Pierre Mantoux Setificato 40. Very close.

I had very high expectations when I placed my order for what looked like a perfect matching shade for Wolford’s “Gobi” color. In fact, much like the image above, the “Jasmine” option seemed like a dead ringer so, what the hell, I wanted one of those. Yet then, we get to the first problem…

The damn sizing chart is pretty fucked up to say the least. It seemingly put me at a large with huge hips and, since I no longer have a belly, I was wondering if I’ll need a belt to prance around in these. Not exactly inspiring confidence in my decision. OK, so these probably weren’t made for the everyday crossdresser, so I got one pair medium and another in large in that Jasmine color just to be safe.

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Posted on May 28, 2014 by Sheery — 9 Comments

Crossdresser in Teddy and Pantyhose

One thing I’ve always been curious about throughout my days of femme delight is whether crossdressing has the tendency to lead into homosexual relations, be it with a man or another crossdresser. Keep in mind, I neither care about putting a label on ourselves nor am I trying to prove true the ancient myth that crossdressers are gay.

It just so happens that, from personal experience, the crossdresser evolves into conforming more and more into, not only dressing the woman´s part, but acting out the part as well. It may be take form as going out in public in full dress or just meeting up with other CDs to have a meal.

Yet, since crossdressing is primarily a medium for sexual stimulation, this would also undergo an evolution over time to keep the stimulation at its peak. Much like the way, for example, a married couple might experiment with sex toys to keep their sex life new and interesting. Side note: this does work for crossdressers as well.

So, over time, the usual slipping on pantyhose, silky lingerie and maybe some heels and makeup would lose its appeal to repetitiveness and, ultimately, boredom. You could have a different silky outfit for every day of the year but wanking the poor little cock so many times, pretty much in the same fashion each time, might get you thinking, “Well, why don’t I wank someone else’s instead?” to make things a little more interesting.

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