Tag: crossdresser dating

Part 1: Getting to know Kristi
Part 2: The HOT date
Part 3: Kristi leaves a souvenir
Part 4: All good things come to an end

I have to admit, I felt quite overwhelmed in that moment as we were standing there making out like teenagers. I was basking in the proverbial afterglow of the most wonderful sex I’ve had in ages and, at the same time, I’m still in my Wolford Neon 40 tights with that nicely welcomed wet spot of Kristi’s love honey right over the crotch area. Being rammed in my pantyhose has been a longtime fantasy of mine and that feeling I had right then and there was exactly why.

Fortunately we weren’t done just yet…

Kristi gave me another passionate kiss, but this time with her hand caressing my hardening girly rod over my wet pantyhose making me let out a light “oooh” in pleasure. She suddenly quit stroking me, pulled away from our kiss and got down on her knees. Then using both hands she started slowly pulling down my pantyhose and gaff all at once (yet again) exposing my little girly rod, now pointing straight her. She smiled as she began to tease it lightly with the tip of her tongue.

Then into her mouth it went, all the way in and with a suction I had never felt before, not even from a biological woman. I could feel her beautiful  lips slowly sucking and slurping back and forth. I moaned louder as I reached a point where I was about to explode in her mouth. However, as I was just about to warn her of the impending flood of my own love juice, Kristi stopped her magnificent sucking and slurping and reached for a condom and the bottle of lube within arm reach on the table nearby. She politely did the honors slipping on the condom and swiping a generous bit of lube over it.

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Part 1: Getting to know Kristi
Part 2: The HOT date
Part 3: Kristi leaves a souvenir
Part 4: All good things come to an end

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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Part 1: Getting to know Kristi
Part 2: The HOT date
Part 3: Kristi leaves a souvenir
Part 4: All good things come to an end

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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Part 1: Getting to know Kristi
Part 2: The HOT date
Part 3: Kristi leaves a souvenir
Part 4: All good things come to an end

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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