Posted on January 15, 2023 by Sheery — 2 Comments

Sheery in the shadows

As a crossdresser, it is always nice to meet other crossdressers, especially given that other non-crossdressers you may end up hanging out with might not be fully into your thing if you know what I mean. Generally this would happen meeting someone online, establishing a little rapport about our tights and favorite girly items we like to wear and then may even end up exchanging numbers. Nothing really out of the ordinary unless you count that crossdressing thing.

Now, if things get a little flirty or (I dare say) romantic, then I can get into that too. However, I would also note that this is in the perspective of female me and not my usual male self. An important distinction because they are in fact quite different.

First of all, there is that whole establishing a “connection” thing. Sure we are crossdressers and obviously have that in common. Maybe we have fallen in love from that avatar picture in the profile and think the other is the hottest thing on earth since… actual women. OK, these are really men, dressed as women who no longer have that traditional male/female division to overcome in order to interact and maybe hook up if that is desired.

Well, it doesn’t quite work that way.

I’m not ashamed to admit that I did learn that the hard way with actual women a long time ago. Reversing that role though makes it all the more apparent. For miss me, it is downright scary some of the creepy crossdressers I have stumbled upon online. One in particular complained I never responded to her online, so I said sorry and gave her my number (side note… not a good idea). Then the messages started pouring in…

Read more »

Posted in Commentary
Tagged with ,

Posted on December 18, 2022 by Sheery — No Comments

Yves Saint Laurent with Wolford tights

Surely you know by now that I love slipping into a pair of Wolford tights, then maybe sipping a glass of wine while enjoying that silky softness on my legs. If you can’t tell, I’m doing just that as I type here. I also just got on my bed and propped my legs in the air to snap a quick photo (ahem, no dirty thoughts now). It’s actually what you see right above. That shade of Neon 40 is called Sodalite Blue and is quite gorgeous if I say so myself.

Normally my Wolfords are at the center of my attention, however, I just happened to receive a package in the mail the other day with some new footwear, ahem, also in the photo above. This is also one of the first times that I can remember where I am actually turned on wearing heels. Seriously, I had one of those OMG orgasmic moments trying these on, posing in the mirror, then prancing around on the carpet.

They are actually Yves Saint Laurent Tribute platforms that I got for a steal practically new on Vinted. Brand new, I wouldn’t even think about buying heels this pricey which I’ve checked online that are between 500€ – 1500€. By chance, I happened to see these in a listing that caught my eye for more like 200€ which I snapped up. I took from my budget for male clothes (zero) and splurged on something that the female in me would more likely enjoy.

Read more »

Posted in Girly Garments
Tagged with , ,

Posted on November 27, 2022 by Sheery — No Comments

Sheery in DKNY bodysuit and pantyhose

As usual, I like to write here when I’m in the mood. That is, fully crossdressed and feeling like miss me. Over the years though, (and it has been quite a lot of years writing here) I’ve gone from slipping on some pantyhose and maybe lingerie to full-on shaving, makeup, wig, perfume and paying attention to those little details to transform myself into a more feminine persona. Oh yeah, and a spray of Chanel No. 5 really does help with that.

I know I’ve dived into this before but the more I’m transformed into a woman and see more of a woman in the mirror, I can’t help but to convince myself I just might actually pass for one. It’s definitely a feeling of empowerment and, not to mention, quite a high that I get off of. I don’t know, I would say kind of like an adrenaline rush I’m having even though I’m not actually out in public strutting my stuff if you know what I mean.

Of course all of this makes me incredibly horny yet in a way that truly distinct from my usual male self. It is just something about smelling that perfume or noticing that flavor from my lipstick or even noticing that warm silky feel of the pantyhose draping my legs. Or is it the wine? It is as if it is an experience of being an actual woman who feels turned on which, in itself, I can say is truly a pleasure I crave.

Then it’s moments like these that I occasionally break out the Fleshlight (with that little thing so I can mount it on my refrigerador) and desire nothing more than to be rammed in my backdoor, ironically, while standing in my heels and fucking my little toy. I have natural female-like boobs, too, (weird genetics) so I also like to pull down my bra and push my breasts together wishing a cock would squeeze right between and come right in the middle of them. Oh, and then I like to give a soft rub on my nipples which gives me mini-orgasms.

You can say my masturbation has evolved over the years.

Read more »

Posted in Erotic Thoughts
Tagged with , , , ,

Posted on September 25, 2022 by Sheery — No Comments
Wolford Vegan Leather Body
Image: wolfordshop.com

Ever see something that on first glance you just have to have it? Yeah, like I really have to ask a crossdresser such a question with an obvious answer? Well, several months back, my eyes glanced on this vegan leather bodysuit from Wolford that made me nearly come in my tights. Aside from that, it is a collaboration with Amina Muaddi and (YIKES) has quite a hefty price tag, $665 in the US and £409 in the UK. OK, I would have waited until the end of season sale for this one I guess.

Yet this thing was so gorgeous I debated selling my car, plasma… my body just to be able to slip into this sexy, kind of fetichy garment. Alright, no I didn’t but you could see what I mean. I really did have to have it.

Then it turned out that miracle happened and I found this very same Wolford bodysuit on Vinted for $100 in perfect condition. It was in a size small which, normally with Wolford bodysuits, I can fit into snugly. So of course I would also like a (vegan) leather bodysuit to look like it were painted on. At a fraction of the price, I rushed to buy it and eagerly awaited that delivery truck like the ice cream man.

Read more »

Posted in Girly Garments
Tagged with ,

Posted on September 3, 2022 by Sheery — 2 Comments

There were many a day in the past where I’ve had that same conversation with myself, then repeatedly came to the same conclusion: So when am I going to quit my crossdressing once and for all? I remember that time when I moved out of my parent’s house to go to college when I knew for sure I’d ditch that, ahem, filthy (but fun) habit. That went well. Or maybe it was that time when I was in pantyhose looking at the mirror at the hair on my legs all squished up, again I thought why keep doing this? Since then I’ve shaved my legs periodically.

So maybe you’ll have better luck and to give you a little nudge, here are the top ten ways you can quit your dirty, filthy (but maybe fun?) habit of yours.

Read more »

Posted in Top Ten
Tagged with ,

Posted on July 23, 2022 by Sheery — 7 Comments

Me in a Wolford Bodysuit and Neon 40 pantyhose

Like countless times before, I find myself sitting down with a cup of coffee in hand and legs draped in my favorite black Wolford Neon 40 pantyhose. I notice a little wear on the heel but, no problem, I have more (yes, more than one) of the same colored Wolford in case of a quick need to replace them. Or maybe a special night out on the town. Yeah right, I’ll be staying in tonight.

Anyway, while I scroll through the news on my mobile, I wiggle my toes and admire that ever-present shine, something I’ve also done a million times. I figure I should be bored of this by now but I’m not. I feel great wearing my most prized garment. Actually not just great but really comforted over my lower half, like a cross between silky tactile pleasure and a nice warm hug from a good friend.

Of course I’m also wearing a bodysuit like in the image above (not the same one though) and a short silky robe to round out my household look. Yet I kind of look at them as adornments to how killer I think my legs look in Wolford pantyhose. I mention Wolford since they are my favorite pantyhose at the moment but these could very well be one my other Oroblu, Pierre Mantoux or even Danskin tights I’ll slip into every once in a while.

Now, to say I have a pantyhose fetish makes me laugh and cry out loud. Of course I use to download those JPEG images and watch any kind of videos where pantyhose was the star (yes porn too, OK?). Not to mention gaze at lovely women wearing those shiny tights from behind my sunglasses. I’ve jerked off plenty of times with nothing more than the closest pair of tights and a hand and, if I do a hard search, I’m pretty sure I can come up with a pair of cum-stained hose that I could try on again for a quick chuckle.

Read more »

Posted in CD Diary
Tagged with , ,

Posted on July 17, 2022 by Sheery — 4 Comments

Posing in Victorias Secret teddy and Wolford tights

I may give an impression that I’m quite the out-of-the-closet crossdresser that you may have seen down the street but the truth is I am still quite private in my life as a crossdresser. Although I have been out in public a few times, it is still kind of a rare thing for me. I guess you can say I still have a foot outside of that proverbial closet at the moment. I am definitely not ready to reveal my feminine self to friends and family. It may never even get to that point but who knows what the future holds?

Now that said, I know that there is that desire to tell my story to someone… anyone please! In particular, that person would not judge me but, at worst, may get a little surprise at my taste in women’s undies or possibly doing a double take looking at one of my female “poser” photos. Keep in mind I’m not talking about those semi-anonymous online friends who I may have had a dirty conversation with here or there.

I mean an actual live person that I could admit all my secrets to, a non-friend and non-family member and definitely someone that does not know any of my friends or family. Hey, sometimes I have to go all out CIA to make sure those rumors don’t get around to the wrong people if you know what I mean.

I would have thought this person would be another crossdresser but, in my case, I happened to be in a crowded bar having a casual conversation with another male who mentioned he was gay, naturally as though he were out of the closet (which he was). I can’t really remember the entire conversation but I do remember saying something to the effect that looks aren’t always what they seem, referring to myself.

“Oh really?” he asked (that I do remember). “Um Yeah, I’m a crossdresser,” I said a bit surprised that I actually did say it. Yet we still finished our conversation as if none of it really mattered. However the topic of my secret crossdressing life did come back to the forefront of the conversation and, meanwhile, I’m wondering why the hell I just told him that.

Read more »

Posted in CD Diary
Tagged with , ,

Posted on May 15, 2022 by Sheery — 2 Comments

Sheery in a Redhead Wig

At last count I had six wigs lying around the house. I think there is another one deeply buried in storage next to some old pantyhose from the year 2000 but we won’t count that one. They have all served their purpose at certain points as the icing on that delicious cake of me the crossdresser. Actually they have been more like the cherry on top, so to speak. Basically, a wig has been nothing more than a finishing touch when I am in the mood to dress.

Up until recently I actually haven’t given much though to that little cherry until I went out and paid for a decent one. I was always pretty much happy with the 30€ – 50€ ($33 – $55) bargain barn rugs that went on the top of my head but I had never given a second though to quality since it never really seemed to matter. If hair is fake, it is fake and, well, looks the part.

Then I figured why not try out a REAL wig as in a professionally made prosthetic piece instead of using the same old strands of plastic that I’ve been use to. I thought about it back and forth whether to shell out ten times the price I paid for the cheapos and, even more funny, thought about just getting another ten head rugs in different colors and styles. I eventually made the rational decision to go for the quality and maybe in a tint that I would not normally go for… the redhead.

So I forked over the several hundred euros from my credit card to a German company for the “Carlotta” bob wig in a “paprika” color. It is quite a lovely piece with curls and a length a little bit short of the shoulders. I decided I had to ready myself well for the trial so I showered and slipped into my girly attire and then spent a good hour doing my makeup. God I hate putting on makeup although I do really like the end result.

Then I carefully combed through the wig with my hands and gently placed it on. I nearly came when I looked at myself in the mirror.

Read more »

Posted in Girly Garments
Tagged with ,

Posted on April 3, 2022 by Sheery — 12 Comments

My leg in Wolford Neon 40 pantyhose

Just moments ago I happened to find myself slipping into a pair of Capezio shiny dance tights that I found in a box tucked away in the back of a cabinet a little bit earlier. Of course I didn’t stop there adding a bustier, some tight-ass daisy dukes, heels, wig and some fucsia lipstick to round it all out. I pranced and posed in front of the mirror admiring what I see, and getting very much in the mood if you know what I mean.

So I had to do what any pantyhosed freak in a similar mood would do in that moment. A little self-loving and some frosting for the cake. Oh yes, I did have a taste in case you were wondering.

In the past (like decades ago), after these typical pantyhose-donning episodes, I usually came out of them in a rush to take off my pantyhose, feeling like I committed a serious sin and swearing I will never do this again (albeit fun at that moment). I always knew I would get these urges to “wrongly” wear silky pantyhose and lingerie in the future but I wouldn’t be able to sustain this forever. Or would I? I figured I would quit my experimental phase of crossdressing eventually and maybe have a normal married life.

If you have read around this blog, you would obviously find this is not true. And I have nothing but pantyhose to blame for turning my life upside down. Oh, why did you have to come into my life way back when I was a kid and give me that little “kink” of pleasure that I couldn’t stop thereafter? I didn’t even like women’s underwear or even looking like a woman way back then. Why why why?

Maybe you are into your own little fix of pantyhose and a wank, probably with a pair of panties thrown in (I don’t judge). However, take my warning, because pantyhose may become the gateway to the following…

Read more »

Posted in CD Diary
Tagged with , , ,

Posted on March 13, 2022 by Sheery — 2 Comments

An old Pantyhose Please image

Just this past week, I had an old external hard drive that I found and was about to toss during my spring cleaning. I had originally planned to take a heavy hammer to it and smash it to bits but, for shits and giggles, cleaned it up a bit and connected it to my laptop just to see what was still on it. It pretty much had all the usual digital stuff you accumulate… work, resumes, random documents and, oh, what is that?

My, that looks like the old treasure trove of pantyhose images I had collected from WAY back when! I realize how “sick” I must be since I have already spent a good two hours looking through these as if they were long lost family photos. The hell with that though, it was nice to go through my old stash of soft-porny images and getting off again like the good old days.

And those days I remember very well. Hours on end surfing the net for free pantyhose images. And not just any images, the shiny pantyhose ones I preferred (and with a bit of lingerie if possible). I distinctly remember there even used to be a website called Winnie Cooper Pantyhose Links from back in the 90’s that would post daily links to galleries where I could get a ton of free photos (like the one you see above).

I guess you can say I was pretty much a pervert back in those days but I’m sure I wasn’t the only one. To my defense, if you had access to free smut, why not take all you can? Although it was a bit of work finding the “good” pics, it was worth it, as I could see with my 25GB collection. I remember decades ago when moving to another apartment running into old Playboy magazines stashed away. Of course I paused and looked through those too.

Besides the actual images, I was also curious about timestamps from the images. From those you can kind of judge when the images were actually created. I happened to find some that were from 2001 from a site called Dodgers UK. Sadly, they don’t look like they are around any longer but, looking through those, I noticed some featured my all time favorite Wolford Neon 40 and I don’t think I realized it. The telltale sign of that being the waistband and unique shiny opaqueness.

Dodgers UK - Wolford Neon 40 image

Read more »

Posted in Discoveries
Tagged with , ,