A Story Of A Sissy Ch 02

I received her email during the Christmas holidays. Like I said, it was pretty tame, but it was the first time a woman had ever written me a story. Usually, I was the one writing the stories. I'd been on Literotica for years, had a few stories, and mostly I liked reading stories. The few I'd written were all based on real experiences and then embellished...extremely embellished. What I didn't realize at the time of her email was that she'd found me on Literotica already.

When we started the shared Doc I moved the story pretty quickly toward my likes, but without being too overt or over-the-top. It was pretty fuckin' sexy. The story was based on two characters, Luke and Lacy. The weirdest thing about it was that we pretended to be "only writing fiction" but in my mind I was Luke and Joan was Lacy.

In the comments, I'd refer to the Lacy character in the "you" pronoun, and she'd correct me saying something like, "oh, Lacy isn't me, she's just a made-up character." But then she'd make comments about Luke and ask me if I liked the direction she was writing him in, and did I like those things, or what do I like, and so it seemed to me, in her mind, she had made the Luke character me.

It was pretty hot. Some nights we'd be on the document at the same time. I hadn't told her that I was a crossdresser, but in hindsight, she knew I was, or at least that I had fantasized about it, because she'd read all my Literotica stories. Not knowing this, I maintained the facade of a normal man. But whenever I got online and wrote on the Shared Doc, I would put a pair of panties and a nice chemise on, have a drink, put music on and create this romantic atmosphere for myself. When I'd see her hop on the Doc it was like being with her in the room with me...exposed.

We'd collaborate on the story-line, throw each other ideas, once in a while either she or I would write a little tangential short story that was independent of the main story, and all the while I'd be dressed like a sissy with my sissy clit completely aroused the entire time. It was the ultimate form of foreplay. I'd never experienced such arousal, ever.

Keep in mind, I had no idea she'd read my Literotica stories. I wrote the Luke character more and more submissive but without any hints of crossdressing or homosexuality. I would have maintained that demeanor until the end of time because I have never risked exposing my sissy tendencies to anyone unless I knew I could trust them and I knew they enjoyed it too.

So, it was to my pleasant surprise when I got on the Shared Doc one day and found that the Lacy character had slipped her panties into Luke's pocket and told him to go put them on in the bathroom of the restaurant where they were having dinner. I'll never forget how arousing that was. It was the opening I'd been hoping for. I took that little deviation and ran with it. I started including more and more panties, more and more submission, more and more sissy aspects.

This went on for months. I would get off work on Friday and spend the whole weekend dressed up like a sissy. It became this strange relationship between me, my sissy, and Joan. One day Joan sent me a list of questions she wanted me to answer. They were under the guise that the questions were to help her write better, more realistic stories. The questions were like, "have you ever worn panties?" Or, "have you been with another man?" Or, "do you like using a vibrator during sex? Have you ever used a vibrator on yourself?" There were a dozen of these questions and when I read them I considered lying to make it look like I was reticent, if not resistant. But, sitting at my desk, dressed up in my sissy, buzzed from whiskey and marijuana, I settled down and replied to each question in full and vivid detail, and with total honesty.

Here's what I wrote:

Joan, I have to tell you, this, whatever it is we are doing, this "relationship", this digital affair is the sexiest thing I have ever done. I have had great experiences with wonderful people over the years, but writing these stories with you has been unequivocally, the most arousing experience I've ever had. So, for these reasons, I am going to be totally honest with you, and I hope you will not take offense and I hope you will not be scared off, and if you feel awkward in anyway, please let me know and I'll stop.

Right now, I'm wearing a pink pair of Vanity Fair, full-bottom panties, a spaghetti strap pink satin chemise, a white lace garterbelt and a pair of white, Wolford thigh-high stockings. My whole body, from my neck down is shaved clean and smooth, not just shaved, but I use depilatory cream to do the heavy lifting and finish the fine parts with a razor and shave cream. I have my nails and toes painted glossy pink and I'm wearing pink gloss lipstick.

I know it must be a shock to you, so I'm including some pics for you. Again, please let me know if you don't like this. I'll stop. I can tell you all about how I got here, to this closet crossdressing some other time, for now I just want to answer your questions as honestly and with detail. This is so very arousing, so thank you and again, sorry if you don't like it.

Yes, I have worn panties...LOL (obviously). That started when I was just a boy and I found my mom's panty drawer. I have worn panties with two women, Jacqueline and Maria, and they both liked it initially, but then I think it got too weird for them. I've been dressed up completely with both of them and at all sorts of various stages. Most of the time it was under the guise of making me seem more like a woman so they could engage in homosexual fantasies. Both Maria and Jacqueline are bi-sexual.

Yes, I shave. Only since moving to Europe have I begun shaving my legs. I started shaving my crotch when I was with Jacqueline, but that was only occasionally. It was Maria who got me to shave my crotch, ass, and under my arms as a matter of routine. She wanted me clean shaven and looking as close to a woman as possible. I've been alone, at least not in a serious relationship, since Maria, and that was 10 years ago, I have gradually increased my crossdressing skills and attire. I can't do makeup, I have no idea how women learn how to do this. I love smooth legs. The crotch kind of sucks if I'm honest, the stubble after a day or two is actually painful (but I suppose you know that) and the only reason I maintain this status, and it's a big reason, of keeping my ass and crotch smooth is because it makes me feel so very feminine.

Yes, I love vibrators. I have a really nice one right now. It's smooth and "normal" sized, water-tight, with a rotating vibration control wheel that allows for a wide range of vibrations. I use it on myself, but not so very frequently. It takes work. I like to be really clean so I have some rituals I follow, of which I'll spare you the details, to ensure a clean and uninterrupted session. When I do fuck myself, I absolutely adore it.

I have used toys with every woman I've been with since Jacqueline first introduced me to them a very long time ago. She loved her vibes. I loved using them on her. More than anything though, I loved watching her use it on herself. Watching a woman please herself is one of the most arousing things I can imagine, especially if I'm masturbating while watching her. I have found that women, open-minded and sexually self-aware women, like their toys.

Yes, Maria used a strap-on with me. She was uncomfortable I think and it was cool, I liked sucking her cock, but when it came to her fucking me she was timid and unsure, so I never pressed her after the one time we tried.

Yes, I've sucked cock. I've sucked seven cocks, not at one time, lol (although that would be fun), but over the last ten years. The first one was when I was still working with you at the school, lol, no one ever knew :-) It's not that I'm ashamed of it, although I was in the beginning, but once I sucked my first cock, that shame went away pretty fast. I don't see sex as binary, or even trinary, it's a spectrum and I like just about all of it :-)

No, I've never been fucked by a man. I would like it, but I've never felt quite right or comfortable enough to try or ask a man to try it with me. I feel like it would be too messy and awkward. I like using a vibrator on myself without feeling self-conscious. I know that must sound weird, especially as forthcoming as I am right now, it's one of those quirks.

No, I've never dressed in public. I am a bit of an exhibitionist though. I've done lots of "exposure" play, both alone and with women. It's funny, just about every woman I've ever been with (since Jacqueline that is) we've had sex in public, done nudity, or partial nudity, panty games, or dress-up games in public, to one degree or another, and every time, the woman seems to absolutely dig it. Women love driving on the highway nude. Jacqueline, Maria, Grace, Debbie, Melanie, Anna, and Toyoko have all been nude in the passenger seat of my car while driving down the highway in broad daylight. I know the names mean nothing to you, but I guess now you know the "serious" relationships I've had in my life. Not so many, but the interesting part is that all of them genuinely got turned on by exhibitionist play.

So, I think this covers all your questions. I hope you are not running for the hills. Talk soon.

I sat still in my big office chair and sipped my whiskey and read my response several times. I remember how aroused it made me and I knew that if I masturbated before hitting send, I probably wouldn't have sent it. So I quickly attached several more pics of myself, tastefully crossdressed of course, and hit send. Then I went and masturbated.

I wasn't too nervous about the things I wrote, it was the pics that had me worried. I remembered thinking that because she'd initiated this digital affair, me sending pics is just one level up. I worried she would be freaked out by my candor and seeing me looking this way, but I felt I could trust her not to expose me.

Remember, I had no idea she had read all of my Literotica stories. As far as I knew, she only knew I was a kinky kind of normal man.

She responded the next day and she was so very encouraging and accepting. She told me she adored the pics. She thanked me for being so honest with her. I remember the relief. I remember masturbating just thinking about her reading my responses. I remember how much fun it was imagining her as she opened her email and saw me dressed up like a sissy crossdresser. So much of my arousal, I realize now in hindsight, is imagining her reactions. Because she approved, my mind went wild speculating. I didn't need porn with her. I would read some of our stories and the parts I wrote, I imagined her reacting, thinking about what she would write next. I pictured her thinking in ways to meet me half-way. I imagined her looking at me dressed up in my sissy and what she must be thinking.

It's only now, after years have passed and I've had time to figure out what is so arousing about this that I finally know why I like it so much. I imagine her looking at me in my panties and stylish Wolford thigh-highs and garter belt. My smoothly shaved legs. My painted toes and nails and lipsticked mouth. I imagine her shock. I imagine the wheels turning in her head about what she thinks about it. I imagine her seeing a man that looks, from the torso down, like a woman. I imagine her walking up to me and caressing me like a woman. I imagine her imaging herself doing that to me. I imagine the conflict she goes through accepting what she's seeing and then thinking of the man I am and the man she thought she knew. I imagine her secretly laughing at me and saying "ha, I have you now you little sissy cocksucking slut." I imagine her mind starting to devise ways of reeling me in and getting me hooked. I imagine her devising ways of driving me deeper and deeper and closer and closer to actualizing my dreams of complete sissy submission.