I was laying in bed on a Shared Doc that my friend and I were working on. It was an erotic story that followed the sexual escapades of Luke and Lacy that we started writing years ago, just after I'd moved to Europe. We started writing it when my friend, Allee had shared it with me just asking for feedback. I was stunned because we were "just friends," and I never expected in a million years that she indulged in this kind of extracurricular.
I guess space and distance gave her the courage to share this side of herself with me. I loved it of course and before I knew what was happening we were writing the story together. She maintained that the writing wasn't sexual, but I readily admitted that the whole thing was extremely arousing to me. I even admitted to her that my masturbation sessions had become totally reliant upon the story we were working on. I practically stopped watching porn because of our collaboration. She giggled and laughed me off, and it seemed to me that she genuinely viewed our story independently of her own sexuality, as if she'd tucked it into some secret compartment that was separate from her.
Allee had no idea that while I wrote on the Doc, during which, oftentimes, we would both be on the Doc simultaneously, I was dressed up like a horny little sissy slut.
I am a crossdresser. Actually, I'm really a sissy. I shave my body, paint my nails and toes, wear slutty lingerie, panties, put makeup on, and sometimes even wear a wig. Oh, and I love stilettos. I've sucked several cocks over the past 10 years and I've never told anyone I know personally about any of it. I never told Allee.
I was not shy about telling Allee anything else. In our story, everything was on the table. The story was kind of like having sex in real life. When you first start having sex with a new partner, you have this back and forth where you try and figure out what your partner likes and you give that to them and they try and figure out what you like and they give that to you and you keep doing that until you both know what the other likes. Our story was like this, but neither she nor I restrained ourselves. She would surprise me with some wild scenario for Luke and Lacy, either together or individually to engage in, and that would allow me to reveal some kinky scenario for them to play out.
For me, they were actual fantasies. Submissive male, crossdressing, feminization, humiliation, exhibitionism, or whatever came to mind, I never hesitated. For her, she claimed they were not "her" fantasies, just "experiments." This allowed me to play it off likewise and I could easily make like I was just "experimenting," and that these weren't actual fantasies for me either.
But really, I was laying back in bed, with my laptop on my smoothly shaven legs encased in Wolford stockings, wearing pink satin panties and chemise.
Over the years, her kids had grown up and were getting ready for university, I'd had a kid, gotten married, and eventually divorced, and time went by. The time we spent writing was few and far between but we would occasionally add to the story. It was up to around 300 pages, mind you, that was over a 12 year span. I rarely had time alone with my kids, but once or twice a year they would go on holiday with the ex and I'd have a whole week to myself. It was in these moments of independence that I wrote in our story.
I treated it like a date, lol. I would go into Prague and purchase a new outfit, depilatory cream, some lipstick, and nail polish. I'd long gotten rid of my wig and heels, but everything else was on the table. Then I'd get home, light candles, put on some Coltrane, pour a drink, smoke a joint and perform my ablutions. This was foreplay.
I'd work on the story all day and night. I would be in a constant state of arousal and inebriation. I would never touch my clit. Oh, I would rub it through my satin panties, insert my vibrating plug in my pussy, and between the crossdressing, alcohol and weed, and writing for Allee, I was practically hallucinating in my frenzy.
It was during one of these long weekends that a message came up on the Doc.
Allee [I know what you are Oberon]
Me [Allee?]
Allee [Are your panties wet?]
I was stunned, but also I couldn't believe it. I wanted to tell Allee everything. Did she know? How?
Me [What?? I'm just writing, what are you doing?]
Allee [Taste your precum O (that was her nickname for me)]
Me [Allee!?! I told you those things are just wild imaginings!]
Allee [If you want to live out your wildest fantasies, go to the Gallerie at Masarykovo at noon tomorrow. Go to the spa on the basement level and ask for Eva.]
Me [I don't really want to do the things I write about Allee, you know that!]
Nothing....
She seemed to have signed out of the doc. My panties were wet and I took them off and sucked on the precum that saturated the front panel.
After orgasming in my panties and then using my mouth to clean them I got a message on WhatsApp.
Unknown [Here's your gift card sissy. Enjoy!]
I tried to reply but no one ever responded back.
I sent Allee an email, tried her on FB but she didn't reply. I lay in bed thinking about whether or not I should go. Should I wear panties? Yes, panties, and my Wolford sheer-to-waist nudes. I resolved to go.
I was certain Allee had somehow found me out. It wasn't a completely blind date. I had done the anonymous Craigslist thing with strange men and that was nerve-racking. This was a "sponsored" event, and Allee wouldn't do anything to hurt me.
I slept like a baby, got up, showered, cleaned up any stray hairs, put on my panties and stockings, and caught the train to Prague. I smoked a joint on my way from the station to the Gallerie at Masarykovo and walked around the mall for a while gathering up my courage.
I was hungry and went to the top floor for a light lunch. After lunch I was heading to the escalator and was checking out one of those pop-up promotional displays for VR and one of the sales girls holding a pair of VR goggles was smiling at me. She was sexy in a strange way, I suspected her of being a very feminine man dressed very convincingly. This disarmed me immediately and I played along.
She led me to a recliner, put headphones and goggles on, and told me to relax.
I never fall for these things. I never even let the ladies in department stores try to sell me perfume or jewelry. I always avoid them, but I was sure this woman was a gay man and she was friendly, warm, and funny, so I settled back in the recliner and waited for the screen to come on.
Before any visuals, the recliner started to hum and seemed to warm up. Over the speakers in my headphones, I heard a woman's voice, "Hello O, we know what you really are."
I threw off the headphones and goggles and the woman was standing over me. "Put them back on Oberon," she said. "Unless you want me to put up your show onto the big screen over there," and she pointed to the corner where a giant screen was showing a commercial for VR.
It flashed for less than a second and I recognized a photo that only I had ever seen. One that I'd taken, one of probably thousands of photos that I'd saved over the years of my crossdressing exploits. Then it returned to the commercial for VR. I scanned around and no one seemed to have noticed and then I stared at the woman above me.
"Everything's ok O," she said. I felt her hand reach between my legs and she rubbed my thigh, sliding discretely back and forth between it and my crotch. "You know you want this O, don't fight it."
She placed the headphones and goggles back on me.
In full VR was a slide show of my photos. Photos I'd never shared with anyone. Then I heard the woman's voice, "Relax and lay back Oberon. Watch yourself, look at yourself, and let yourself go. Let yourself become a woman."
I slipped off my goggles and scanned around the room, made sure that I wasn't being broadcast to the entire top floor of the Gallerie and then looked up into the woman's eyes who was standing over me smiling warmly.
She put her hand into my pants and cupped my shaven clit and pussy in her fingers and rubbed and squeezed me. Each VR recliner was in its own little pod and unless someone was directly in front of the pod, everything was shielded from view.
"Don't worry O," she said. "As long as you play nice, you have nothing to fear. We won't broadcast anything you're watching. Just enjoy this. Let go. Any actual control you think you may have right now is an illusion."
She was so sweet-looking. She was clearly a he from this proximity. She was a sissy.
"Do you want to take your pants down?" she asked. "No one will know it's you, not with the headphones and goggles shrouding your appearance. We won't broadcast you, you can let your real you out for the few people who might come close enough, but they won't know."
She was very convincing, but I hesitated.
"Don't worry O," she said. "In time, and if you're a good girl, I might even let you put my soft and limp clit in your mouth, wouldn't that be nice?"
Before I could think, let alone speak, she told me to put my goggles back on.
I watched the slideshow of all the photos I'd ever taken of myself. Some, I'd not seen or had long since deleted and hardly recognized them except that I knew the outfits were mine and my face.