Sheery in bed touching herself

Sure I like to write, in a way to let out all my weird, perverted or just plain everyday thoughts into something I will more than likely look back on. So yeah, a public diary of sorts that I leave open to all who care… or not. I also do happen to keep a little notebook that I write in strictly on the topic of my crossdressing. I don’t know whether it’s the pen and paper or it’s as if I like to keep pretty damning evidence around but I kind of enjoy it.

So I happened to read through it the other day and an entry from a while back caught my attention (and jogged a memory). I won’t lie, I do get off on my crossdressing. I’ve even touched on masturbation methods here or there but this was actually a particular session that I remembered pretty well… I wrote in my journal while in the act of some self-intimacy which happened to be something I always had wanted to do when I write. Call it inspiration or whatever, maybe you can relate…

5/5 – As I write this, I am dressed in my new teddy and Neon 40 tights, red wig and some lipstick grinding away with my Fleshlight. I feel like a princess with a dick and feel no shame for it. No way!

I slip on a condom (to make things less messy so to speak) and grind harder, faster. Ooooh! I obviously love this feeling plus I love how I look in my beloved lingerie and pantyhose (+ wig and lipstick). I turn myself on with ease!

Now I’m shaking, ready to come but I delay it. This is quite possibly the best feeling… hot, en-femme and horny as shit about to come. That stretch on my pantyhose, taste on my lipstick and strain on my legs from my tall heels all magnify that orgasm yet to arrive… then it DOES leaving me shaking and trembling. OMG!

Needless to say, I remember not leaving a mess afterward!

Oh, I guess I could part now on this gem of an entry…

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Sheery dressed for a date

Part 1: Getting to know Kristi

Part 2: The HOT date

OMG I’m thinking. The irony that cocks don’t really turn me on (or men for that matter). However, when I’m all dolled up and feeling oh-so-feminine, there is nothing I crave more, especially if it is from another beautiful pantyhose-wearing crossdresser like myself. I could go all Freudian and analyze my gender-bending tendencies, which I did happen to be thinking about for a split second, or I could just enjoy the moment right in front of me here and now. I chose the latter (duh).

Kristi heard my demand to get that lovely stiff girly cock of hers right inside me at that moment and stood up from the sofa. I stood up as well then planted my tongue down her throat (again) as I gently stroked her cock with my hand, making sure it remained nice and hard. Meanwhile, she grabbed a condom packet and a tiny bottle of lube from a rather ornate box nearby on a nearby table. I snatched the condom from her and ripped it open. I had always wanted to do that condom-in-mouth-and-blowjob-it-on thing so why not since the opportunity presented itself. It did involve a light pushing with my teeth but Kristi seemed to love letting out a soft “oooh” and, not to mention, her girly cock seemed just a little bit harder than before.

As she went around behind me, I bent over with my hands resting on the armrest of her sofa and stuck my ass out, maybe a bit too excited to get into position. Then I pulled up my dress and gently rubbed my own pantyhosed ass on her gorgeous pantyhosed cock, enjoying the hell out of this silky, sexy sensation. She caressed her hands on my ass then gave one cheek a light slap while letting out a giggle. I let out an “ooooh” in my now much-improved girly voice.

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Sheery caught in Wolford bodysuit and tights

Well, for starters, I’ll let it be known that I’m still in the closet with my crossdressing. I’ll still have a quick public outing here or there but I’m still not quite known as THE local crossdresser just yet.

To be honest, I don’t see that changing any time in the future and I’ve been fine with that for a while now. My en femme crossdressing world colliding with my “real” world with my friends and family is not a reality I wish to happen. Believe me, I’ve mulled it over and even sought advice about it and came to the conclusion that maybe they are best apart. And that is OK.

So that said, last night I happened to be doing my little dress-up thing and, while I don’t always go full makeup, I almost always put lipstick on. I usually like some kind of bright pink or burgundy shade and I happened to swipe on a fuscia color that I love. Well, of course at some point I had to get back into to boy-mode, then run down to the “mini mart” store nearby my apartment building and get a few items for dinner.

Off went the femmy clothes, on went the pants and sweatshirt and off out the door I went.

As I am about to arrive at the store, I walked past a guy staring at me like he recognized me. Odd, I thought since I didn’t recognize him but as I opened the door to the store, it triggered a sudden sheer terror in me that I forgot to remove my lipstick. The clerk (who know me) saw me enter then quickly look down and leave as I did an awkward run-walk back home where I then removed that bright beautiful fuscia shade right off.

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Sheery, undressing

There is no doubt that we as crossdressers, transvestites, t-girls… whatever you want to call us, retreat into our feminine skin, slip into something we love and momentarily basque ourselves into that girly little world of ours. The reasons may vary but it is pretty safe to say that it makes us feel good. I mean don’t we spend our lives chasing feelings and finding pleasure where we can? Then what happens when we find pleasure?

We repeat it of course.

But what really is that pleasure we seek in our femme skin? It most often is sexual (duh) yet it doesn’t just stop there really, am I right? Well, that may very well be where things can get a little complex. So back to that feeling we’re chasing, things can get arousing (duh) or maybe it calms us down after a long day of digging ditches in the prison yard. Maybe we just like that tactile tight silky feeling of that underwear that gives us that momentary chill up down down our spine.

Well, last week, I planned to try on a new piece of lingerie I had just purchased and did my usual routine of shaving all around, showering, then body lotion, then on to the makeup, etcetera. As I slipped into that new lavender teddy, I felt this incredible rush that I really only experienced a handful of times as a crossdresser. It wasn’t the usual “Oooh this is nice” while in my silkies but a more intense full-on high all over my body.

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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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Wolford Neon 40 tights in Electric Pink shade

Not news that I love Wolford Neon 40 tights. OK let’s move on… I’ve always been obsessed with those fuscia Neon 40 tights ever since I saw them, hold on, ten years ago. Of course I gave up my search for them probably nine years and 11 months ago but I swore back then that if I ever come across a pair in whatever state it was in, I’m buying it, whatever the price.

While randomly browsing around, I happened to find Wolford tights for sale on Amazon, but the German site. Amazon does carry Wolford tights and other items (which is no surprise), however, the German version happened to have shades of Neon 40 that were not available anywhere as far as I knew. Yet further browsing around, I noticed there was an “Electric Pink” color available to buy which quickly got my attention.

Electric Pink = Fuscia? It kind of sounded like it to me but I had to find out. Could these be the fuscia tights of my dream?

Well, I happened to remember writing about those lovely fuscia tights some time ago (link above) so I dug back into the archives in this website to find that article for an image of that fuscia shade. Then I noticed that the article happened to be from ten years ago almost to the day. There was some weird time warp prophecy going on here.

With my love of anything fuscia colored then rekindled, it was time to dig deeper…

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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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It’s that time of year, ho ho ho. Ok, whatever, another year of getting socks, candy and a couple of t-shirts. Woo hoo! Well, your crossdressing friend (wink wink) always has a few things on her wishlist when returning home for the holidays. I understand it is not always easy to shop for that little girly man but, take it from me, these suggestions can help…

10. A stocking for the other leg.

9. A free pass to go ahead and dress away in front of the whole family. No one can say a word or they get shot.

8. Your conservative, law-abiding, church-going and happily divorced uncle decided he won’t be making it this year.

7. A good time to repurpose that perfume gift set from last year that you didn’t like.

6. An official pardon form your sister for stealing all her shit from her closet.

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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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Sheery in her favorite Victorias Secret teddy

My first love has always been pantyhose since I was a kid. Yet as I grew up through my weird pubescent years I grew a fondness for lingerie way back when there were paper catalogs that had lingerie sections which I collected, my comic books of sorts I guess. I would fantasize and obsess while gawking through those pages, not at the typical ladies in bras and panties, but the more sultry garments. You know, anything with garters or all lace or “push-up” but what really caught my eye were the teddies. I fell in love with how they were basically a bathing suit but far sexier.

Then there was that time when I was still in high school, I had just got my drivers license and started working in a shitty fast food job earning minimum wage but my own fun money basically. So what did I do with that first paycheck? I drove right down to the mall, gave into my urge to try lingerie that wasn’t stolen, and bought a sexy camisole set. Wearing it later that night, with pantyhose of course, was at the time probably the most erotic and sensual experience I ever had.

Of course, being able to shop and afford things myself, my lingerie purchases didn’t stop there. With my fascination with teddies, I remember ordering a hot pink lace teddy with underwiring and a very high leg cut from a Sears catalog. Then I excitedly picked it up a few days later, rushed home and slipped it on, again, over my pantyhose. It was another sexy, sensual moment in the books but this teddy was something that truly felt amazing having on. I wouldn’t say it was a very feminine feeling but more like a sexual excitement and of course shortly after came the gratification (pun intended).

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