clitty fail

i tried the experiment i mentioned below - tucked and taped myself and vibrated myself. No stroking, no fingers,  just the vibrator. It was very very intense. I kept at it for over an hour. I had two or three of what might have been orgasms but no ejaculation. I'm not sure whether or not I liked it. I'm sure I'm going to try it again.

can it become a clitty?

I'm returning after a week-plus hiatus to take care of some other business. There are two things on the near horizon that I want to try.

The first is shaving. I'm really interested in doing a full-body shave. Both to see what it feels like (the other CDs I'm finding on lushstories tell me it's amazing) and so I'll look better in the pics.

The other thing I'm considering is this: tucking and taping myself then see if I can cum using a vibrator on my head like it was a clit. I've never tried this and in fact, can't really cum unless I'm laying on my back. So masturbating in the shower is pretty much a "no started", as are many other positions.

I'm not committed to any of these yet, still thinking over the implications and the possibilities.

cross dressing and submission

i've been spending a fair amount of time on lushstories.com. i posted my first story and some pics there. there are a lot of awfully pretty cross dressers on the site. that's both exciting and discouraging. it makes me want to get in the gym 7 days a week instead of 3. maybe that's good motivation.

chatting with some of the fellows made me think a lot about why i'm here and why i'm doing this.

what got me started was a submissive fantasy. i've done a lot of chats online (more on that later) and had a lot of fun but that world of submission is still something i think of as a writer, as theatre, as an indulgence, not something i crave as part of my lifestyle.

cross-dressing may be different. it just feels good. i've always like the kinds of tight, shiny clothes i get to wear when i'm doing this. i never gave much thought to the makeup, hair, and clothes part of it, just the underthings. now, seeing some of the more accomplished guys on the site, it's got me walking through the department store thinking "if i dropped about 20 pounds, i would sure look good in that."

this is an interesting phase i'm in!

hard to find partners unless you're a woman

Saturday night, my Goddess Tiffany told me that She would be out and unavailable. Her Instructions to me were to go into a number of chat rooms on the Internet and make myself available for cybersex. When finished, i was to send the chat logs to Her.

At a little after 1 a.m., i launched IRC chat and set my nick to one that reflected a bisexual submissive. i got no hits in the first fifteen minutes or so. i wasn't surprised, if i'd learned anything from the last few sessions, it was that there is not a huge audience for experimental bisexual submissives.

i spent the next half hour or so trying on different outfits and taking pictures of myself in different poses. None of them were satisfactory at all, so I deleted them. i am far from "in shape" and the outfits i chose showed more flaw than feature.

i went back to my computer and checked if anyone had PM'ed me. No nibbles. As i had the other night, i checked /whois for the two men who had used me the first night. Neither of them were online either.

i decided i would do a gender switch.

i thought hard about that before doing it. Not because i had any hesitation, but because the nature of what i was trying was this: can i roleplay a cross-dressing submissive? The first sessions seemed to show i could. i decided that, like so much in the cybersex world, this was another case of supply and demand. If nobody wanted what i was offering, i needed to offer something else.

Would i learn the same things about myself, though? i thought about that a little while longer then decided that, tonight, i really didn't care.

i wanted to get off.

so, i thought about it and invented a new persona. i can't reveal it because then i can't use it again, but part of it said "use me hard". Within minutes, i had three, then two more, then two more.

This was not a surprise, but was revealing. Was it the woman's name or the 'use me' attitude that brought the names? As i started chatting with each of them, i realized that only some of them had any interest in BDSM or D/s at all. i whittled the pool down to two so i could maintain at least some consistency.

The first fellow (NM----) chatted politely. His questions were good and i had to improvise a biography on the fly. "My husband is vanilla and asleep. He knows I do this and is OK with it and loves to read the logs the next morning. But he reads them alone. He won't masturbate in front of me." etc.

We were online for about 15 minutes but it didn't lead to much for either of us. He experimented with a few humiliating scenarions, each of which turned me on, but he never followed through. i wonder now if maybe inventing them was enough for him? i wonder if maybe he didn't think of cyber the same way i do. i'm not sure, but we parted friends.

The second chat was a girl in her 30s and her boyfriend. She told me he was there with her. He wanted to do her while she was having cybersex with a woman. i did my best to describe my touching her, kissing, licking, servicing her as best i could. She responded once in a while. i pictured the two of them going at it and shifted gears to being a toy in their evening's play. It felt good to the submissive side of me, but wasn't very arousing.

Toward the end of that chat, several more came up, plus i called back some of the first crowd.

By 2:30 a.m., i had four new ones on the line.

The first one was from Australia, a man and woman who wanted me to phone them to verify i was a woman. They were looking forward to a 3-4 hour session. At that time of night, i wasn't up for that so we parted.

The second one started out strong but by then, i was really craving some harshness. i tried something new. i stood up and put my clothes back on. He said, weakly, no. i turned and walked to the door, waiting for him to get touch. He ordered me back but again, i just said no. He gave up and i left.

That was also a good learning experience. What did i want? i realized i was goading him into being rough, but was that really the kind of message i wanted to send out to men? When S---- slapped me the other night, i liked it, but when he slapped me again afterwards for no apparent reason, it bothered me not to stand up to him. i'd decided i would not make that error again. But here i was goading a man to throw me down to the bed.

i've had conversations with women over the years about 'rough sex'. They like it, but i don't understand it. i understand humiliation, BDSM, and the like, but 'rough sex' is a category i don't get. And here i was asking for it. He didn't take the bait, so the problem went away.

The third fellow started off strong, in fact he sent me a pic of his junk. About ten minutes in, he keyed 'gtg' and vanished. By now, i am not even wondering about what happened or what is happening, i am getting horny and frustrated.

The fourth fellow didn't last much longer. He said 'I want to use you hard!". i typed: "tell me what you mean by hard? tell me your deepest darkest fantasies, the things you would never ask a woman to do." He never replied.

It's now about 3:30 a.m. and i'm hot and bothered and frustrated.

i decide to try one more thing. There's a channel called 'jackinchat' i'd been lurking in. The chat in there is particular interesting to me, guys asking guys if they want to jerk off. i assumed it was a gay channel, but the more i read it, it was guys like me who wanted to just share stories and get off.

i hooked up quickly with a guy who wanted to tell fantasy stories about wives and girlfriends. it was intense and i was finished - sated and satisfied - in less than 10 minutes.

i may have found a new online home.

transgender and cross-dressing

i spent a few days last week imagining what it would be like to be fully committed to this identity rather than playing with it as an experiment. i surfed the web looking at various transgender and cross-dressing sites. i abandoned myself to the project, even to the point of creating a new "look" for myself in my mind. i'll go into that in a separate post.

In at least one of the sites, someone quoted an "old joke" that goes something like this: "what's the difference between a cross-dresser and a transsexual? About 2 years!" On another site, someone posted that "drag queens are typically straight guys playing a role. At the end of the evening, they take off the makeup and go home to their wives or girlfriends."

So, there appears to be a wide range of opinions about this. Which is a great thing, in my mind. Human sexuality is so complex that simple answers just don't seem possible.

i can say that i can remember enjoying the feel of women's clothing as far back as early adolescence. There is something magical about the way they feel, both from the outside and from the inside. From the outside, the smooth, shimmering look and feel of a pair of nylon panties or stockings is the most amazing thing i can imagine. And, from the inside, the tightness is so satisfying -- the constant reminder all day long that those panties or that leotard is there.

i can get a similar thrill from men's sports compression-type underwear, so maybe this isn't cross-dressing at all?

i considered that, but i also realized it goes a little bit deeper. There's something i find enticing about posing, about hiking up a skirt and revealing a leg. i don't go in much for makeup and wigs, though i could imagine it.

The point of this is that i think it puts the lie to the "about 2 years" joke. i've been flirting around with this world (oh! Freudian slip!) for over 30 years and still have no feeling of gender confusion, of being born into the wrong body, or of wanting to go out in public to see if i could 'pass'.

i just like the way these things feel.

(or, as some of you might be thinking: so far...)

Why This Blog?

Some weeks ago, I was having an online chat when something fascinating happened. A chance remark led me into an ongoing exploration of a side of me I didn't really know was there.

Some background: I write and post a good deal of adult BDSM and D/s fiction. My main theme is humiliation, though the use of restraint and pain has been getting more and more prevalent. I correspond regularly with readers who post comments. I appreciate the feedback. I'm also very interested in human sexuality in its myriad forms, so I like to engage in discussion with those who find my stories appealing.

Over the years, I've engaged in email and chat exchanges with women readers who wrote me telling me how much they enjoyed my stories. I often use those encounters to spark further stories, so it's a 'win' for everyone.

This time was different.

A made an offhand comment to me about housework. It sparked a flash of an image in my mind. I was standing at the kitchen sink, naked except for a small white apron that left my bottom (and most of the rest of me) exposed. Our chat very quickly turned into a session in which she dominated me. In the weeks that followed, we took this roleplay further.

I'm finding it so compelling I felt I would start my own blog to document my exploration from the inside. I've been posting to the "submissive to the circle" blog but those have all been in-character posts. Since this is a very conscious RPG, I wanted a 2nd blog to explore it from both 'inside' and 'outside' the character 'jake' / Jake Lacy.

So here it is. I hope you find it interesting and that you will post comments back to me.