Confession of a Total Sissy

Somehow this was the most difficult thing I'd had to do since becoming my wife's full-time sissy. Across from me sat my best friend Jack and he was waiting for an explanation. Well, what kind of explanation could I possibly give him? Here I was, his co-worker, his buddy since college, the guy he shot pool, played cards, watched the Knicks with at the Garden, and I was wearing a short, silk sarong-type skirt, a sleeveless mini-t, and beaded thong sandals that showed off my painted toenails. What's more, my hair, which had grown considerably in the months since he'd seen me last, was pulled up…not in a ponytail…but two flowing pigtails each tied with a red ribbon.

Where was I supposed to start? I guess its lucky for me that Lara gave him a bit of a heads-up. "We don't want the poor guy having a heart attack," she'd said, grinning wickedly, when she told me of her plan. "Or worse, getting a spontaneous hardon for you. Or do we?" I blushed even deeper than I had already been blushing when she said that. I was more afraid, of course, that Jack would be totally disgusted when he saw me like this. After all, I had always been a guy's kind of guy. Oh, god…not that kind of guy's guy. You know what I mean. A regular guy, like you.

Sort of.

That's how I decided to start off explaining what happened to me. By explaining that I was a regular guy that just happened to get into this…ahm, predicament. I guess I should have known that Jack would be understanding, or, at least, open to what I had to say. I had known him long enough to trust his reactions, but you never know how another guy is going to react to something like this. Anyway, I knew I'd be okay when he didn't run screaming from the room or make fun of me. He seemed a little uncomfortable…well, who wouldn't be? But I could tell he was trying to figure this all out. I guess we both were!

We had talked about sex-stuff sometimes in the past, like most guys do, but nothing really specific. I didn't tell him what Lara and I did in the bedroom, for instance. I mean, it just seemed like one of those sex-things that guys don't really need to know about each other. So when this little thing started between Lara and me, well, it simply would never have occurred to me to mention it. Besides it wasn't any big deal—at first. And it began innocently enough. It started one night when, seemingly out of the blue, Lara had asked if I would try on a pair of her panties.

It wasn't a big deal, I swear. I figured it was just some playful little thing she wanted me to do. Our sex life hadn't been so great lately and I was willing to do whatever if it would spark her interest. I can't say I never thought of wearing panties before. I mean, what guy hasn't at some point, right? So I stepped into the panties Lara handed me: a tiny pair of blue lace bikinis. I guess it was probably pretty obvious by the reaction of my traitorous little penis how much I got off on wearing her underwear. "Hmmm," she said, running her fingernails lightly over my lace-encased erection and licking her lips, "that was refreshingly easy."

From that night on, she had me slip on a pair of her panties in order to "get me hard quick" so that she could bring me off without going through a lot of fuss. I felt sort of grateful that she cared enough about my sexual gratification, especially since she didn't seem to want sex for herself. So I eagerly put on her panties and laid back on the bed while she jerked me off. Sometimes she'd let me touch or kiss her breasts, but mostly she just wanted me to lie there and enjoy the sensations of her hand on my pantied crotch. My orgasms were cataclysmic. Who wouldn't agree to doing as she asked?

I swear that's all it was…at first. Eventually, though, she claimed that I needed my own panties. I suppose it was inevitable that she'd come to this conclusion. It made perfect sense then…and still does…and besides, I didn't want to lose those wonderful orgasms. I didn't even protest when she had me wear the panties under my clothes to work. What was the big deal? Besides, she said it made her hot to think of me all day wearing panties and when I came home she'd prove it by stripping me down to my pretty underwear the moment I set foot in the door.

It's like I was addicted. Maybe I was—maybe I am. I went right along with her when she had me shave my legs and paint my toes, saying that smooth legs and polished toenails looked sexier with panties, and I guess they must have: it was oral sex she was giving me by then! Am I just dumb—or what? It never seemed to occur to me that I was a closet trannie: I really just assumed that I was getting into Lara's newfound enthusiasm for pleasuring me. Hey, stop laughing…

Okay, I guess I am dumb! Duh-uh!

Anyway, there I am at night in a teddy or sexy tap pants and camisoles, shaving my legs, painting my toenails…Oh, I'm sorry. Lara said I needed to start wearing girly night things to go with my panties. She claimed that pretty panties just didn't mix well with sweatpants or my usual striped pjs. It seemed logical. I mean, I had to agree from a purely…fashion, point of view. Oh gosh! Do you see how she led me to this?! I'm having the best sex of my life, but look at what it cost me! And that's not all, as you can imagine.

I wasn't sure if Jack or anyone else at the office noticed how I started dressing for the office. No one ever said anything if they did. Even now I'm blushing all over to think of it. I was wearing girl flats and what I hoped everyone would figure were just ultra thin socks: in reality they were stockings, the real French kind, with seams! I was so embarrassed. I always tried to keep my feet under my desk or the conference table if we had a meeting, but it was hard to keep my ankles from showing, especially since Lara insisted I wear slacks an inch too short in length. And then there was the ankle bracelet…thin…but it was so darn glittery! I was afraid to even show my fingernails: clear polish. And I tried to make it look like I was being hip with the earrings, except three in each ear? Oh god, come on!

And when I told Jack I couldn't see him for basketball or tennis on the weekends: I felt awful, but how could I tell him that I spent from Friday evenings to Monday mornings completely feminized? I'd be talking to him on the phone making some phony excuse that I was changing the oil in the car or painting the living room, and the whole time I'd be sitting there filing my nails and wearing a pair of red hot pants and a cut-off t-shirt, waiting while the depilatory cream worked on my legs.

I'm not sure why I kept going. Like I said, maybe I was addicted. Fact is, the sex wasn't even there anymore: no more oral, no more handjobs. But in a weird way, Lara had me thinking that if I kept doing what she wanted, maybe it would come back again. It didn't; she hardly touched me anymore and still I was hard all the time. Lara would scold me for touching myself, get mad, stopped talking to me. But I couldn't help it. That's when it hit me like a ton of bricks. It wasn't the sex that had me turned on all the time. It was this…being like this…I actually…groan…liked it!

Was I gay? Was I transsexual? Did those strange terms really apply to me? I had no idea but it was too late to turn back. I'm not even sure if I wanted to even if I could. By this time, Lara had come to a decision about me touching myself: it was either hormones that would render me more or less impotent or a kind of chastity belt. I chose the latter, although, in some ways, its kind of worse. I get so…okay I'm blushing again…you know what I mean. I really want it, but, I can't. I just can't, unless, of course, she lets me, and that's pretty rare.

I guess I have to tell this part, too. She told me to, and I really don't want to make her mad or anything, if she checks up on me by asking. Its funny how we never really talked about sex and stuff, and now I'm telling everything now. Well, every few weeks or so she lets me out of this thing I wear, this chastity device, and I get up on the bed in a corset and garters, or a teddy, or slip and there is this dildo-thing, you know, and I put it inside me, and…it was hard for me to do this at first, it really was, especially with her watching…but pretty soon it seemed, well, natural.

And now, I really like it, I really do. I don't even need to touch myself when I use the dildo. I just push it in and out and it doesn't take much time at all before I'm coming so long and so hard that I feel like I will do anything, anything at all. I like being dressed in pretty things and feeling full inside and its such a long time between sessions for me that I'm just so turned on. This is hard to say but Lara puts a rubber on me and when I've filled it she takes it off again and puts one end into my mouth and squeezes the cum out and I swallow it and I don't mind it at all.

Whew…let me catch my breath.

It was right around then that I took that leave of absence. I knew it was career suicide, but what could I do? Lara was making so many little changes to me by this point that it was getting to be totally impossible to live a life like a normal man. I knew that Jack would get that promotion to director, and that made me feel a little better, knowing, I mean, that if I couldn't get the promotion he would. I really meant what I said in that congratulatory email, although I couldn't help but wonder what he thought of that feminine pink typeface, the cyber bouquet, and the fact that I signed my name Traci, with an "i." I don't know. I guess I hoped he'd think it was a typo, or a joke, or something. But, in some ways, I sort of hoped he wouldn't think that. Do you know what I mean?

I stopped talking. I figured I'd said enough already. I was a nervous wreck, fiddling with the end of one of my pig-tails, and mortified at how it made my charm bracelet jingle. I was sitting the way Lara had taught me, my legs crossed at the knee, and the result was that my already short skirt had crept high up my smooth bare thighs. On top of that, I was jiggling my foot, the beaded flip-flop dangling from my painted toes, as if I were trying to call attention to them, which I wasn't, I swear it. I wanted away from there, and I didn't, and I wanted to cry and apologize and claim it was all a great big mistake.

Jack seemed to be be taking in my story and then he simply asked me if I were happy. "I am," I had to admit, shaking my head, pig-tails unabashedly dancing. I was smiling a little, I think, and dabbing my eyes at the same time. "That's good," Jack said. "That's what's important." Then he did something that was amazing, just totally amazing. He reached out and he touched my leg, just above the knee, his big warm hand resting there, reassuringly, on my bare thigh. It wasn't sexual; well, it was and it wasn't. It was…I don't know, possessive, sort of, like he was telling me, not to worry, that he would take care of me.

And I felt something I never expected to feel, that I didn't even know it was possible to feel. I think Jack recognized what I felt, maybe he felt it, too, or whatever the male counterpart to that feeling is. Wow…did I actually say that?! I suddenly wanted that hand to travel further up my thigh, beneath my short skirt, under my panties…over the chastity device that kept me imprisoned. He told me not to worry about a thing, that I could return to work as his administrative secretary, that with overtime I could probably earn almost as much…

I was so excited and relieved I crossed the short distance between us and threw my arms around his shoulders and kissed him. I'd lost my flip-flops somewhere on the way and found myself sitting on his lap, giggling and licking my finger as I wiped my lipstick off his lips. He didn't seem to mind at all. He had worked one arm around my waist and stroked my knee with his free hand. But Lara—what would Lara think? "I wouldn't trouble your pretty little head about that," Jack answered smiling from ear to ear and that's when I realized that this whole thing had probably been in the works for some time. "I have a feeling she'll be okay with the new arrangement."

Sometimes I wonder if I should have been mad: my wife and my best friend plotting to turn me into a sissy, and all. I mean, I spend all my time as a girl now, working 9 to 5 during the week in skirts and heels and on the weekends it's capri pants, jumpers, and, in the summer, skimpy little halters, short-shorts, and sundresses. Jack and Lara are openly lovers, although Lara has also taken on several female partners, and everyone at work just figures I never came back. I often suck Jack's cock, although never in the office. If he gets horny during the day, he rents a room for us in a local motel. Every two weeks or so, he'll take off my chastity device, kiss me all over, and then fuck me anally. I come like crazy, and then he locks me up again. Lara laughs at me, but she says she's proud of me; she treats me a little like a pet, something she's fond of in a distracted way but, then, she always did. Yes, I admit I wonder sometimes if I should be mad, but I guess I really am happier this way. Wouldn't you be?

--the end--