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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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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Sheery in bed and in Wolford head to  toe

It goes without saying that we as crossdressers have wild thoughts going through our minds, especially when relaxing, sipping wine and getting in the mood. Yes, our fantasies take us to uncharted waters, hold no boundaries and give us moments of that little adrenaline rush for what could be in complete ecstasy. OK, maybe we may get a good wank out of it. No boundaries remember.

Now I won’t speak for all crossdressers but I will say a good part will have one or more of these fantasies. You don’t have to admit it!

10. Wish a push-up bra worked for the belly.

9. Wish someone would say with a straight face that I’m the prettiest thing they ever saw.

8. … Or at least let me know I have a run in my pantyhose.

7. Be a normal man again, but with only a couple of feminine tendencies.

6. Wish there were an easier way of dealing with the “bulge”… or to be in fashion for actual women to have one.

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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)…


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.


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 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.

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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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Pantyhose, heels and in position (Wikimedia)
Pantyhose, heels and in position (Image: Wikimedia)

This is Part 4 of 4 of the story when two male friends decide to have a little fun in lingerie, pantyhose, heels and makeup after a casual evening at the bar.

Part 3: Curious Crossdressing

Part 2: Let’s Play Dress Up

Part 1: Two Friends, Maybe More

* * *

Sticky Wet Pantyhose

So there we are, Eve and I lying on my bed making out like two crazed, horny teenagers. I can’t really tell what was going through my mind, probably due to the numerous beers consumed earlier, but all I can say is that it feels incredibly exciting and I was more than willing to “cross the line” where I haven’t been before.

To let out a little secret, I have had an attraction to other crossdressers for quite some time now. For me, there is something so sexy about a male who can transform himself into woman (the more passable, the better of course) but, oddly, I’m not in the least bit attracted to masculine, unfeminized males. Maybe you can say that I’ve grown a fondness for chicks with dicks.

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(Flickr: tomswift)
(Flickr: tomswift)

Part 3 of the story of two friends in the midst of playfully crossdressing together after a night of drinking.

Part 4: Sticky Wet Pantyhose

Part 2: Let’s Play Dress Up

Part 1: Two Friends, Maybe More

* * *

Curious Crossdressing

It was a subtle yet convincingly girlish “ooh” Adam (actually, now I’ll call him “Eve”) made. Just that one silky touch to her leg was enough to set me dizzy with excitement. Normally, being alone and caressing the pantyhose on my own legs has a similar effect. But to feel it on someone else, albeit another male, is almost too much to bear.

Eve reaches down and gently strokes my crossed leg while my excitement grows so much that I begin to tremble. She takes notice.

“Are you OK?” she asks with a smile, as if she knows exactly what she is trying to accomplish.

I smile back not saying a word, uncrossing my leg and, this time, gliding my nyloned leg against hers and letting out an “ooh” of my own in the best feminine voice I could muster. I could do this all day.

Eve then takes a seat on the bed next to me crossing her leg over and caressing my thigh with her silken toes. She then moves her head forward towards mine as if she were trying to kiss me but then pulls back. At first, it shocks me, but then I’m thinking, “Is it my beer breath?”

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Adam loves black pantyhose (credit: WendySuntan)
Adam loves black pantyhose (credit: WendySuntan)

We come to Part 2, continuing on with the story of two friends having an innocent drink at a bar, a crossdresser and a gay male (insert joke here).

Part 4: Sticky Wet Pantyhose

Part 3: Curious Crossdressing

Part 1: Two Friends, Maybe More

* * *

Let’s Play Dress Up

Both Adam and I make the short walk to my place, half a block away. We enter and Adam sprawls himself in comfort on the sofa while I immediately head to the refrigerator and grab a couple bottles of beer.

My nervousness has calmed down slightly but I still feel rather giddy. This takes me years back (a lot of years) to when I was on my very first date with a girl named Mandy. Completely nervous and trembling the whole time, I was so excited about being on an actual date that it was too hard to contain.

“But me and Adam?” I’m thinking. We’re two friends and, while he may understand my feminine fetish and even crossdress himself, I don’t believe he gets a kick out of it. Besides, I’m not into men so nothing could happen between us.

Yet the night is still long, or so they say.

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