In bed in a Wolford dress and Neon 40 tights

Read Part 1 here…

A couple of hours into the four hour trip on the train to Madrid, my excitement settled down a bit and I fell asleep for maybe a half hour or so. When I woke up, a thought crossed my mind. Shouldn’t I be “dressed” for the occasion as in be fully dolled up by the time I rang the buzzer to Kristi’s apartment? I mean I did pack very well prepared to transform into miss me with the only male clothes being what I happened to be wearing there on the train.

Unfortunately, I didn’t just go anywhere en femme in public even though I could have gotten away with it in Madrid (maybe). So I devised a plan to change into my dress and tights at the Atocha train station when I arrived, wear my leisure sweat pants and coat over them and then when I arrived at Kristi’s, do a quick transform out of them and into my heels. Hopefully somewhere along the way I could make my face up really quick. A couple hours later I arrived in Madrid and set the plan into action…

So far, so good as I made my way out of the train station and onto the metro (e.g. subway), dress and tights safely hidden underneath my clothes and I even put on my medium length red haired wig tucked under a baseball cap. I got off the metro after three stops and checked Google Maps for her street, just a few blocks away. As I arrived to her building, luck would have it that there was kind of an alley just before it with no people walking around in it, something kind of rare for Madrid. I ran up into it, pulled out my makeup bag from my suitcase and did a rush makeup job on my face using the mirror in my finishing powder to help me apply it on. Ok, this looks passable, I thought.

Then I switched my running shoes for some tall heels just as an older lady walking her dog happened to stroll past with a curious stare. I just smiled as I repacked my suitcase and made my way out of that alley and on to Kristi’s building where I arrived a minute later. I rang her buzzer and that familiar sweet voice answered which almost made me faint. “OMG we’re finally going to meet!” I said to myself kind of giggling.

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The author before her date

Hey, we all need some lovin’ don’t we? It’s not breaking news that I’ve dipped my toes in the pool of lovely and equally horny crossdressers. Or maybe that a particular crossdresser was probably the best lover I’ve ever had. You know I do get all hot and steamy dolled up and slipping into my usual pantyhose and lingerie and, after all, what am I to do when the fantasies rage?

So, it also shouldn’t be a surprise that I am on the chats and dating applications somewhat frequently. While I do have a number of friends online, there are maybe only a handful that I’ve actually met in person. Then maybe out of those, I still keep up with a couple of lovely girls who live nearby and then another darling in another country about once a year around Christmas. Well, let’s add another lovely girl to that very short list now. We’ll call her Kristi to protect the “unabashedly guilty.”

Even in the age of social media, socializing online, including with video chat, sucks. Like big time. I definitely take it with a grain of salt since I like to talk face to face. Then again, how many crossdressers are hanging out in the little bar right down my street (none)? So, I have a continuous conundrum and just deal with the digital experience. Kristi was different and happened to stand out from the usual chit-chat chat day in and day out. We shared things in common such as our love for Rock n’ Roll… and legwear. She preferred stockings but I let that one slide though I like my stockings every now and then.

The professionally femme photos in her profile certainly didn’t hurt either. I fantasized over them.

But then things took a turn when we went from typing away in chats to video Skype. It started out with me shaving my face and then carefully applying makeup and a long wig for the first few face to face chats where she appeared to do the same. I even talked to her in a slightly more feminine voice (or at least tried) trying to leave an impression. She had seemed to have a more natural womanly voice which I found seductive and sexy. We chatted twice face to face before agreeing to “show more of ourselves” on our next call.

That meant dressing head to toe and having our cameras showing our full selves and what we were wearing. The thought excited me and the fantasies continued even so much that it probably took a couple hours for me to actually dress and get my makeup on. Here is what I wore to our first “body to body” call:

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The author, Sheery, right after shopping

For about the last, oh, couple of decades, we’ve had the convenience of shopping online which means 1) Waking up in the morning (or drinking wine before bed) 2) Thought comes to your head to buy something (sexy) and 3) Browse around and eventually click the Purchase button, but then 4) Wait that day or two for that “special” package to come.

Particularly for the closet crossdresser, this is fairly standard procedure… easy, you get what you feel like you want and no one else needs to know or doesn’t care on the other end. I mean would you rather have to pick out your silky treasures in person and then get that side-eye from that real female taking your payment? There use to be that day when having to shop in person use to exist you know.

Wait, hold on, you can still shop in person?!! Lingerie, pantyhose… makeup too?

OK, I’m sure there are many crossdressers out there who do actually buy their femme gear in person which nowadays isn’t anything out of the ordinary. So I happened to be near a large department store last weekend and, knowing they have my favorite Wolford Neon 40 tights, decided to go in and “have a look around.” Now, truthfully, I usually have bought pantyhose in person every now and then (even lingerie when I was 16) because it always gave me a bit of an adrenaline rush. There was even one time when I was purchasing the aforementioned Wolford Neon 40 tights when the sweet cashier lady commented to me “Wow, you just went right to those quickly!”

Um, yeah, caught. I’m pretty sure I blushed as I handed her my credit card.

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Similar heels that I injured myself in

Well, it finally happened. Probably the greatest peril of being a crossdresser other than getting beat up by other men with other secret fetishes. Not to mention, it took a little hit on my femmy ego. I actually injured myself…

First of all, I just have to say I love tall heels. If they are not at least four inches tall, they do not even get to touch my lovely pantyhosed feet. Oh, and that one inch platform in the front, yes, I’ll have that too! I love how they make my legs look super long, or at least fool me into thinking so. Then there are those tall stiletto heels that look like they balance on needles… my favorite.

Well, I happened to be wearing said stiletto heels not too long ago to go along with my favorite black Wolford Neon 40 tights and a sexy bodysuit. As usual, I like to prance around on the carpet, check out how my ass swings and, if nothing else, get a little practice in walking around in my most treasured footwear. Then I got a new lesson on what really needs to be practiced for the wannabe woman in stilettos taller than her ego…

Standing.

You heard me right. Hell, it is the first thing you learn once you slip into heels for the first time. It is quite a daunting feeling and experience at first but you eventually get use to it. Same with walking around. Heel, toe, heel toe. Admittedly it can be a bit scary at first but it easy to maneuver around with maybe 15 minutes of practice. Even with those tall  four-inchers!

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Sheery relaxing in pantyhose

I finally did what many a crossdresser has done before me. Admittedly it was difficult but very much necessary. Not just for me but, my god, this should have been done more than a decade ago at least. Yes, I’m talking about the “purge” but not for the usual reasons a crossdresser would do this. No, it was a far different reason…

I had too much shit.

Now keep in mind, this isn’t to cast a shadow over the typical crossdresser purge. That is throwing away anything feminine linked to one’s crossdressing due to shame, anxiety or pressure from social norms to be “normal.” This can be a serious distress and a challenge to get over mentally. While I have never actually purged my collection before, the social pressures have taken a toll in the past and I can sympathize with that.

There were times, however, I have actually wanted to purge my pantyhose, etc. in the past but I was either afraid someone would catch me doing that or I realized that I had to get new femme gear if/when the urge came around again. Basically, I knew it wasn’t practical. Oh, and the shame after wanking one out of the park while in my skimpies was definitely a frequent occurrence in my early girly days.

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Sheery in pink bodysuit and Wolford pink tights

A while back I told of my absolute joys of being a crossdresser, so why not get all dolled up and let out all my frustrations today? Don’t get me wrong though. If you came here looking for reasons to really hate crossdressing and give it up, you would be out of luck. I LOVE my crossdressing life and the way my new bra hugs the natural curves of my chest. Like anything in life, however, it does have its pet peeves and annoyances from time to time.

Sometimes those pesky problems can get the best of me. Most times I brush them off. Well, now it gives me a little writing material.

So, as I sit here in my black Wolford bodysuit, Neon 40 tights (black) and a black miniskirt (plus my favorite heels), time to begin the tales of things I really HATE about crossdressing…

The Guilt

This use to be an issue in the past but not so much over the last decade or so. Nonetheless, it’s worth a mention… getting that urge to slip into some pantyhose, throw on some lingerie and get a quick wank out of the way. Then the post-climax being the need to stop doing this from now on.

I can safely say this was due to me not being comfortable in my own skin. Hey, once I realized this crossdressing thing won’t go away at all then there was no choice but to embrace it, pervertedness and all.

Shaving

Smooth legs are awesome. Smoothness everywhere else is nice. Shaving sucks. So do those little nicks and cuts from shaving. Why do I have to make an appointment in my calendar every week or ten days to do it? My god, shaving sucks.

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Sheery in Wolford Iris bodysuit and Neon 40 tights

I’ve noticed over the years that the more involved I am in my crossdressing, that is getting all the little woman-like details sorted out, the more I’ve come to appreciate it even more. There use to be a point in my life where I thought it was a curse (well, many points actually) but when I came upon the realization it will never go away, I guess I thought, What the hell, I might as well enjoy it while I’m alive.

The truth is I actually feel like it’s WAY more fun immersing myself in my own feminine world. Trying that new lipstick color, searching for those perfect heels (still), finding out my perfect wig color is dirty blonde or just enjoying that feeling of being all dolled up. I haven’t even gotten into the sexual kink out of it all either which, I might add, is also pretty awesome at this stage of the game.

Anyway, here is my list of things that enjoy most about crossdressing (in no particular order)…

Sensuality

It’s difficult to describe that feeling when I’m completely transformed into miss me. It is kind of a warmth all over sexiness knowing this could be dangerous. Maybe it is the combination of noticing the tightness of that miniskirt or that sweet smell of Chanel that also heightens and arouses the senses to an unbelievable degree. In any case, I like this and don’t want it to stop.

Escape

I hear and read about it all the time how crossdressing is used an escape from your real self and I can say that it is true. Life is hard and we all have our ups and downs, especially me, but getting into our alter-selves does really separate myself from the real world, even if just for a moment. It is honestly the only thing to make me forget about those Zoom meetings at work coming up in the next couple of hours. Um, yeah sorry, it looks like I’m having trouble with my camera here…

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Sheery in Wolford Tights and Sonia Body

If you’ve been here long enough then you may already know pantyhose is definitely a passion but not the so-called fetish it always use to be. Don’t get me wrong, I love and wear them as always (like right now even) and they never lost their erotic appeal, not for a second. Way back, however, there was a time where they were the only focus… slip some on, have a quick wank and go on with my day. Or I’d just wear them under my jeans and take notice of that swishy noise and silky feel as I’m walking in public. Alright, I still do that from time to time.

What I’m getting at is that the days of the panty(hose)-boy with the “fetish” are long over in favor of doing this whole look like a girl thing. It’s funny, too, that I never understood how this possible evolution could even happen. I even quite stupidly thought that eventually I would grow out of that kink. Maybe I would just have to take a few minutes to get away from the family, sneak out in the woods, slip on my Wolford tights and come on a pine tree every now and then.

Let’s just say it didn’t quite work out that way.

Not that I’m unhappy being a (way) more girly me. I just never thought it would come to this, no pun intended. Over the years, I’ve read many crossdressing blogs and also have met others online that started with the typical pantyhose fetish which eventually led to full on transformation and, in some cases, changing gender completely (aka Caitlyn and, yes, she did have a pantyhose fetish in her past). What was really strange to me, however, was that it seemed like in many cases the whole thrill we seek by wearing pantyhose in the first place seems to have disappeared in the process.

I mean once you are hooked, how could you want to leave your love of pantyhose?

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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.

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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.

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