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.

Read more »

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:

Read more »

Selfie in Bustier and Pantyhose

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

Read Part 2

Sharon was excitedly busy giving me the blowjob of her life when I suddenly had a moment of realization. There I was lying on the bed in my bustier and pantyhose and with a hole in the back that I could still feel wet from the lube Sharon had used to wet her cock that pounded me a good thousand times or so. The sexy crossdresser making me her toy and actually getting my silkies dirty had always been a fantasy of mine.

Yet this had turned into everything I imagined it would which struck me as odd. Does anything, especially a fantasy, ever end up being like you dreamed it would? “Maybe it would come close,” I thought as I watched Sharon’s head bob up and down and drowning in her sucking prowess. Nonetheless, I enjoyed the moment and the absolute “naughtiness” of our sexual encounter. I was at the peak of feeling feminine and sexy and never wanted that to end.

Sharon stopped her her vigorous blowjob all a sudden and climbed over me and into the cowgirl position with her ass just above my still-hard cock. She pulled down her black Oroblu pantyhose just enough so her bare ass was exposed then leaned over and gave me a soft kiss along with her sultry smile. As she reached for the lube nearby, I caressed the smooth, shiny nylon covering her legs and indulged in the feeling as they even rubbed against my own pantyhosed legs with every movement she made.

In an excited rush, I grabbed a condom from the nightstand, ripped open the package and slipped it on as Sharon dabbed some lube on her hand then gave my rod a quick stroke to glisten it up. She then raised her ass, positioned my cock ready for the back door entry into her and began to let it slide in slowly.

I noticed the tightness of her sphincter which gave me a jolting rush from the incredible sensation on my cock. We both let out a loud moan in unison (girly voices of course) as she continued to ride my love rod with a very precise gyration of her ass. I actually admired for a second how Sharon could move her ass like that while the rest of her body remained stationary.

Read more »

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.

Read more »

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…

Read more »