Well Look Who Had the Hot Date There

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:

  • My favorite black bra
  • A cropped sweater that opens in the front to go over the bra
  • A black miniskirt
  • A gaff to hold back the manhood
  • Black Wolford Neon 40 tights
  • My favorite YSL heels

We obviously had a rapport before that call but I could say the attraction and nervousness was mounting, for myself at least. I looked stunning, or at least I hoped I did. Then that fateful annoying Skype ring came as I lied on my bed hopefully giving Kristi a good view when I answered. “Hi!” she greeted as I saw her with a view of her black sweater and patterned miniskirt standing in her kitchen. Oh and not to mention I gazed at her supposed black stockings she had on underneath. I uttered out a “Hi” maybe a couple octaves above my intended feminine voice.

“How are you?!” Kristi excitedly greeted back at me. “Oh don’t you look gorgeous dear” she continued with a noticeable flirt. I thought lying in my bed might have been a bit silly but there I stayed as we talked and talked. Then talked some more. Eventually the conversation moved on to the inevitable… some prolonged flirting and then on to the whole “what I would do to you if only you were here.” Then we played a game of rock paper scissors to see who would first perform a strip tease on camera. I lost.

I finally got off of my bed, positioned the camera on a table top and did a little pre-pose before trying to recall how to do a strip tease. Fuck it, I’ll just wing it and began by turning around with my back to the camera, legs wide apart, and bent over showing off my ass while trying to look back at the camera. I then danced and pranced removing my cropped sweater and then slowly lowering my miniskirt until kicking it away with one of my heels. It actually turned me on so much that my throbbing cock began to hurt with my gaff cinching ever more so tight.

Kristi didn’t say a word, but appeared with a frozen stare on her screen, which I took as a sign she was into it like I was.

And then it happened. My instincts came out as well as my now-hard cock which I pulled out of that gaff and up and over my tights. I stroked it and softly asked Kristi “Is this what you were looking for?” This felt kind of weird to me since I’m typically paranoid about masturbating on camera. After all, you never know who may be recording on the other end. I didn’t care though, but only after maybe 30 seconds of stroking myself, I carefully tucked my girly cock back under the gaff and pulled my Wolford tights back over it.

“Your turn” I tell her jokingly.

To my surprise Kristi actually did her little number stripping down to her cute bustier/bra, lace panties and those black stockings I knew she had on. I was stunned by her beauty as she then whipped out her own girlhood, fully erect, and seductively stroked herself looking straight into her camera. “This is all for you” she said. I just had to pull out my cock again and join her in our Skype video masturbation session.

While I stopped just before I came, she didn’t and came right in her hand. Then brought it up to her face and slowly licked a little bit off. “You want a taste?” she asked. Yes, I really did, and asked her when we could see each other. “Anytime” she replied. We ended our video chat with a kiss on the screen and a date in person for two days later.

I managed to get it down to the very next day. After a very anxious 24 hours, on to the next train to Madrid I went.

To be continued…

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