Posted on May 19, 2016 by Sheery — No Comments

Flexees Bustier

Similar to many other crossdressers, I try to make my somewhat flat male-shaped chest transform into an alluring, curvy shape that could be taken (or, really, mistaken) for the female form. Sure, I’ve tried the myriad of push-up bras, the ever popular Wonderbra, gel inserts for bras and the like.

I’ve never found anything, however, I could just slip into and get instant boobs without having to resort to pricey breast forms or other things specifically made for the crossdresser. Sure, those would work well in giving me the ladylike shape I desire but I don’t find them the least bit sexy when I want something silky draped on my body if you know what I mean.

So imagine my surprise when I tried out a shaping bustier for the first time and pulled that tight fitting stretch satin over my ass and waist and let the bra-like cups rest snug and comfortably on my chest.

Vavoom! OMG! I could not take my eyes off those beauties right before my eyes. I even threw a t-shirt on to check out my new silhouette… yep, that’s a woman right there in the mirror.

This gorgeous piece of lingerie is a Flexees Firm Control Bustier which, unfortunately, has been out of production for a short while now but can be found in the good old standby, eBay. I actually came across it by accident looking for butt plugs (that’s a story for another day) but turns out to be my now favorite thing to wear while daintily prancing around the house.

Since it’s a shaper, it is a tight and very snug feeling much like your overweight uncle who you haven’t seen in a decade giving you a hug. However it really does smooth out those bulges, not to mention, let’s you breathe in the process while being comfortable (for the most part) at the same time.

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Posted on April 19, 2016 by Sheery — 5 Comments

Oroblu Bustier and Thong

It’s not often that I go on a date with another crossdresser but I too often question myself as to why not just have a little “fun” when I can. So I did and what a rush it was! So here is my little kiss-and-tell of that one very unforgettable date. Note that the name of my “significant other” has been changed to preserve her identity.

Read Part 1

Sharon giggled for a second and made a humored attempt at an access hole through my pantyhose by poking her rock-hard cock into it several times while I’m on my back with my legs pulled as far as they go. As I anticipated her “entrance,” feeling her cock in and out and just barely teasing my ass was, in fact, a turn on. The tease made me so wild with anticipation, I start to tremble from the excitement.

Yet, realizing that the nylon and spandex was tough to break, Sharon ripped a small hole with her fingernails just below the crotch area and gently widened it exposing my asshole-turned-vagina. I even noted to myself, it would have been wet as possible if it weren’t for those damn gender differences. Oh well.

I grabbed a condom and lube, conveniently laid ready in place on the bed, and unrolled the condom onto her cock in a smooth, single stroke. Next, I squirted a little lube into my hand and softly stroked it over the condom-covered-cock while she let out a slow “Ooooh.”

Sharon was very gentle at first, easing her slicked love rod through my sphincter which penetrated with a little resistance but gave me a shock of excitement throughout my body. I remembered thinking “Oh my god, there is a dick inside me!” Even a wave of panic came across me.

“Am I really being fucked in the ass?” I thought for a moment. “Should I be doing this?”

It wasn’t my first time, though, so in that exact same moment, I consciously decided to calm the hell down and enjoy the experience. Otherwise, things can go south rather quick which I did not want to let happen.

“Yes, I should little bitch,” became my next thought. No going back then.

Sharon entered deeper, then deeper with her first few slow thrusts until finally making full penetration. There, she held her love rod in place while grabbing each of my straightened legs and pushing them back, using them for support. She flattered me by mentioning I have sexy, flexible legs which then gave her the green light to do whatever she wanted. I mean anything.

The real fun started, though, as she fucked with just more force than before which sent me through another wave of excitement, an exhilarating body high. I had always practiced anal penetration with a dildo a similar size to Sharon’s cock, however, the real thing was WAY different. There was no match of the sensation of hot flesh pounding me from the ass masturbation of a hard rubber dildo I was used to. This was definitely something I could easily get used to. Oh, and any guilt and second thoughts I had… turned into shame as to why I haven’t been doing this sooner.

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Posted on April 5, 2016 by Sheery — 4 Comments

Sheery in lingerie, tights and heels

It’s not news that I’m willing to stray from my traditional vanilla hetero side and indulge in an escapade with another sexy crossdresser. It was my first time and it was a little awkward, sure, but not any different from that first time with a GG girlfriend many years back. The seed had been planted, though, and the next time would be a far better experience for certain, much like where the vanilla hetero experience took me.

Bisexuality is still something relatively new I’ve dabbled into after straying in and out of the bicurious phase more recently. To be quite honest, it excites me now more than ever before and will go out of my way to explore it when I have the chance. Then, of course, I have to spill it all here, not to brag about the conquest, but rather share the experience. So keep in mind the name here is changed to preserve the identity of that dear crosslover.

I have to admit that crossing that line I’ve always been taught was taboo or “wrong” isn’t easy. Also the experience doesn’t always go as planned (read  the link above) but it can turn out an exciting fling which leaves you wanting more. So, whether or not you’re a relative newcomer, this could either make the bicurious in you think about that next step or possibly relive your tales of chicks with dicks.

So here goes my adventure (again)…

Me and Sharon had met online several months ago. After the usual hellos, flirty exchanges (a pic or two included) and chat room sessions, it was time for the meetup. In a hotel. So it wasn’t as if we were in the dark about what we were going to end up partaking in. Yet the anticipation of slipping into my silky lingerie and pantyhose in front of another crossdresser doing the same was enough to make me cum just at the faintest thought of it. Finally, came that magical day.

And there I met Sharon at the bar in our hotel who was a little bit older and a little taller than I was and fully dressed in a black sleeveless dress and long brown hair that wasn’t a wig. She was strikingly beautiful which intimidated me for a second since I was in public-male-mode (I still didn’t dress in public). Yet she fully understood this and we casually had a drink and chatted. We hit it off right away with the usual bullshit “What do you do?” which eventually led to conversations about our crossdressing lives to which we could hardly find an end to. As well, it was always a relief to share that side which is hardly discussed among others.

There is, also, nothing like casual crossdresser talk to get in the mood and we eventually made our way up the hotel elevator to room 505, a little tipsy and very horny by then. Feeling a mutual attraction, we even grabbed and gently held hands on the way from the elevator to the room. I felt very comfortable and  immediately attracted to Sharon after revealing that femme side of me dying to get out. Of course Sharon wore it on her sleeve which I admired and made her even more desirable.

We enter the room and my first course of action was to open my suitcase and pull out…

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Posted on March 20, 2016 by Sheery — 3 Comments

Wolford pantyhose and string teddy

I quite simply love pantyhose. It’s hard, though, to love something so much and not have it change your life in some way, if maybe a little perverted. Yet perversion is lovely, fun and sexy thing to dwell in so here are my reasons why my life will never be the same with pantyhose. Well, besides the obvious really…

10. Three words: hand wash, ugh.

9. The razor for my legs is more expensive than the one for my face.

8. I say things now such as, “bare legs… ewww!”

7. I spend more on a pair of pantyhose than on a date.

6. Suntan has a whole new happier meaning now.

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Posted on March 6, 2016 by Sheery — 2 Comments

Black teddy with nude pantyhose

I have no idea why it’s taken so long to discover but perfume has suddenly become a weapon of choice when I transform to my womanly self. Maybe it is because I always believed that if it can’t be seen then it can’t be sexy. WRONG!

So there I was one day browsing the usual close-out sales in February and came across one of those Christmas gift packages for sale. You know, the kind that comes with perfume, maybe some moisturizer and then some kind of special box or case to stuff them in. Well, my choice of the moment happened to be some Desire Me by Escada with body moisturizer and a cute little satin “vanity” case… at half off.

What the hell, right? I finally bought my first perfume ever, sight unsmelled.

Honestly, I did it more out of a necessity than a curiosity. I mean I have a ton a sexy lingerie, pantyhose, a couple skirts and dresses, makeup, wigs, etc. Yet I have never even given a single thought to masking up my manly scent with something other than deodorant. Really, what gives there?

Side note, I do use Secret deodorant which is strong enough for a man, woman or the everyday crossdresser alike.

So the day comes when it arrives in the mail. I open the box containing the black satin vanity case and admire it. OK, it’s cute, kind of like a purse without the strap. Next, I open it and pull out the moisturizer first then dab a little on my hands and apply some to my chest. I quite like it actually even though it is just everyday lotion with a great smell attached. I think I’ll save this, though, for those times with the sweaty balls just after some exercise where it will come in handy the most.

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Posted on February 21, 2016 by Sheery — 7 Comments

Nude in Oroblu Pantyhose and Clogs

There’s one thing I’ve come to realize is becoming a common theme as I write here. It was somewhat explained in my last post to the women readers (maybe all two of you). Yet, I’ve noticed a trend going way back to even the early days of filling up this website with page after page of endless dribble.

I’m almost always horny when I write and, if not, I try to get there somehow.

It’s funny how it has even grown through phases of turning the light on, if you will, before typing away on the keyboard. At first, it was just slipping into a pair of any old pantyhose and waiting for that erection to begin to kick in (see image above). Nowadays, it’s more complex. I slip into one of my few favorite pantyhose, a chosen piece of lingerie or even a camisole and mini and a select pair of heels. Then I finish it off with a wig and some makeup.

A little more time consuming now, yes, but I’m actually more into my female persona and, while I could just peek into a crossdresser chat room and get some filthy talk and camera exchanges going, I prefer to express my current “on” state in words that may get archived somewhere in digital land so the future crossdresser can look back and go “Huh?”

What’s different now, however, is that the more I do to become my woman self, not to mention the extra hour involved, the more I take pleasure in actually being that woman. Do I still get my seemingly required erection? Definitely, but I also get a deep body buzz of excitement from just looking in the mirror and knowing I’ve transformed to a woman. It is a sexual thrill still yet, equally, it is a sensual power trip that is completely intoxicating.

In fact, it is so overpowering, I nearly orgasm without having to polish up the bishop. Yes, really. I never imagined it would come to this but there’s just no going back to those days of getting my jollies from just a rag pair of pantyhose. No way.

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Posted on February 14, 2016 by Sheery — No Comments

Pantyhose and Polka Dot Heels

I typically like to write when I get in the mood. That meaning it’s usually morning time and I just crawled out of bed, still in my slightly wrinkled satiny camisole and pantyhose, and put on a silky robe and then some coffee on the burner. The jolt of coffee then kicks in what I would call my crossdressing buzz. In other words, I feel a little horny so I might as well write.

That said, my perspective then becomes not one of deep insight and philosophical analysis of why we are who we are but rather a reflection what I personally feel at the moment, crossdressed. So there you have it, a man draped in satin, lace and nylon writing in sexual overtones which, when you realy think about it, boils down to a man writing about sex. It may be geared for the average crossdresser or male pantyhose enthusiast but women may find it as just guy chat down at the bar, albeit, a bit kinkier. “Um, no thanks,” I can hear as you click away to Zappos. I understand.

Not that I’m looking to pander to women or, all of a sudden, cater to the audience of women or even a date for that matter. That’s not the point. Then again, I don’t want women to leave here thinking us crossdressers (really, this one in particular) are a bunch of pervy weirdos either. OK, so we might be (this one in particular), however, there is a side of me, and maybe others, that has a lot more in common with our mimicked counterparts than what is likely perceived.

I’ll try to explain it further. Call it a sort of enlightenment from a man happily in pantyhose and drinking coffee (and a bit turned on). Please note one thing and that is that crossdressers are very fluid in their beliefs, interests, sexual preference or even choice of garments. So I don’t speak for all, per say, just your truly.

The Feminine Side

I firmly believe that all males have a feminine side to them. Some acknowledge it naturally without knowing, while others may not even try at all. I particularly know it is a major part of who I am and act it out, if you will, accordingly. In my case, that female side of me is primarily sexual, so I want to feel like a woman, be desired like a woman and express my femininity as a woman which, in turn, fills a need to validate the female side of myself.

Now, I neither claim to be a woman or even being similar to one, nor do I wish to become a woman now or in the future (but who knows what the future brings). I prefer instead to enjoy the sensations of femininity whether it be by slipping into sexy lingerie or simply just shaving my legs. I have that need to step into a role as a sexually attractive woman, then validate it by being desired by other men, women or other crossdressers.

The cherry on top for me, and ultimate validation, is to be ravaged and cummed on as a woman. Yes, I know the gender parts don’t equate by I do have a “hole” too.

The Taboo

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Posted on February 7, 2016 by Sheery — 5 Comments

Guess Geary Sandals

It’s no secret that succession of crossdressing phases goes something like this: slip into your mom’s pantyhose as a wee-tot, then try on a bra and heels and maybe her makeup a few years later. Then at point when you can pay for all this shit yourself, you buy them all for your very own. So shoes and in particular, high heels, would typically be a part of that equation. I’d say for most crossdressers in my opinion.

Well, somehow after all these years from the wee-tot stage, I still seem to have an aversion to high heels. I think they look sexy and I want to love wearing them since they are clearly the perfect accessory for gorgeous pantyhose over freshly shaven legs. I even splurged on some gorgeous leather clogs thinking that would spur my lust of the heels world. Sadly, those very lovely clogs have gotten few uses to grace my pantyhosed feet ever since.

“What gives?” I’ve been thinking to myself. I can’t go out with just pantyhose and regular shoes. My high heels just aren’t “doing it” either for me if you know what I mean. Then I finally realize the issue while browsing for heels one day: I never chose the right heels… duh.

Here’s a quick rundown of my collection of high heeled shoes…

  • Six inch clear plastic heels and, yes the stripper kind. Cheap, uncomfortable and painfully obvious what they are for. Seemed like a logical purchase at the time.
  • Six inch over-the-knee glittery boots. No, they are not made from leather or even faux leather but fish-scale shiny fabric. Bought with the heels above. Ditto on the logic.
  • Wedge sandals. Found in a steal of a deal on eBay. Had to glue a strap back in place not too long ago. They still haven’t made me feel quite like a supermodel.
  • Leather clogs. Definitely the most upscale high heels I’ve ever had but they are just not quite me and are, therefore, rarely used. I must not like heels then?

Yeah, I can see other crossdressers shaking their heads at me. Enough said.

First, let me start out by saying that one telltale sign of a true woman is her ability to look through and pick out a pair for herself. I found this to be quite a journey through hell at first. There aren’t just a few high heels to chose from but THOUSANDS. I’m talking just high heeled sandals, too, not boots, flats, casual and whatever else to which there are millions more to browse through. OK, so this is what it is like for a woman when shopping for shoes… I almost call it a day. Almost.

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Posted on January 24, 2016 by Sheery — 2 Comments

Edith Body teddy over Filodoro pantyhose

I’ve been devoting quite some space here to pantyhose lately, almost seeming to forget their other silky (and just as sexy) counterparts… lingerie. The real reason for it’s omission is I haven’t really found anything in a while that I like and I rely on slipping into an older piece usually bought from a lucky whim. It’s primarily due to my issues with the typical lingerie found these days, not just from the point of view from a crossdresser, but I’ll go out on a limb and say for women too (OK, maybe some):

  • It is cheaply made from only nylon and/or fishnet and in the same black, red and white colors. Not to mention pricey for the tacky styles and low quality.
  • Or you find something you can just picture draped elegantly over you. Then the price tag let’s that dream die hard.

So, it usually means an undies purchase for the femme me is in the form of pantyhose, pantyhose and more pantyhose. Well, that is until I randomly came across a sexy teddy that caught my eye, overpriced of course. However, after a little digging in Google, I reached the ultimate candy store for crossdressers, SeksownaForYou.pl, from Poland.

This site appears to be the umbrella shop of Polish brands of lingerie, Avanua, Casmir and Passion which, to tell the truth, I had never heard of until I found the website. Yet, the selection of silky threads was amazing and now I’m extremely elated after tearing into that unmarked package that I received this past week.

First of all, while browsing the website, I was quite content to find lingerie styles that looked like fashion made actually made for this season. In other words, none of that run-of-the-mill fishnet bullshit you would see at your local sex shop. No, I could see there was the possibility of some quality in that stretch satin visible in many of their pieces. At least enough so where I absolutely had to try them out.

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Posted on January 10, 2016 by Sheery — 3 Comments

Teddy and Pantyhose

It’s probably a given that if you are reading this right now, you might have tried at some point to stop crossdressing, only to come back as if falling off the wagon of masculinity… again. No worries, your inner woman always welcomes you back and asks you, “Who the hell are you kidding?” If you need more reinforcement, here are ten reasons to listen to her.

10. It’s either those pristine, always hand-washed pair of silky thong panties or those old tighty-whities with the skid mark still showing.

9. You never have to leave the house to hook up with a woman.

8. You don’t have a fucking clue what else to do with your heels collection.

7. Bruce Jenner has been your hero from the beginning.

6. The hormones have already kicked in.

5. You’re still the starting catcher on your team.

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