Hypnotized by Stephanie Silver
Part Two
I could end the story there, I guess. But I have a feeling it would leave a lot of unanswered questions. Because, actually, what I've written so far is just the beginning. A lot has happened since that first, magical time.
I can just imagine the questions. So when did you start wearing skirts? When did you try on your first bra? Did Dirk ever see you in panties? Did you ever give him more than a hand job? Did he ever get to fuck you? And how come you ended up marrying a woman instead of Dirk?
Uh, well, let's see. I started wearing skirts in 1996. I tried on my first bra when I was eleven. No, it didn't fit. No, I didn't really care. Yes, Dirk did see me in panties. A lot. More often than he saw me in boy underpants, actually. I mean, it's not like he saw me in boy underpants that often, so, you know, once we got started doing that, it just started to seem more natural for him to see me that way.
Let's see. The answers to the other questions: Yes to more than a hand job. Yes to Dirk fucking me. And, uh, the last question, why did I marry a woman instead of Dirk? I don't know. It's hard to say. Maybe the easiest answer is because, at the time, marrying a woman just seemed like the logical thing to do, while marrying someone of the same gender wasn't legal.
Except that avoids the real issue, which is that neither of us wanted to come out as gay. And so we had our secret love affair that is still a secret to this day. Even from our wives.
Okay, so how did I start wearing skirts and stuff with Dirk? I guess, the easy answer is that it's not that big a jump from wearing jewelry to wearing other girl things. Jewelry was the ice breaker, I guess. After that, about all he had to do was bring something he wanted me to wear to the tree house, hypnotize me, and then tell me to put it on. And I would. Or did. With no questions or argument.
It helped that I'd worn panties and bras before, of course. That took away any inhibitions I may have had on the matter. The only difference was letting Dirk see me wear them. And to that I'd have to say that once we kissed, it was hard to have any real inhibitions with him after that.
But, okay, the first time he saw me in bra and panties. That's probably what everyone wants to know about. Actually, that happened not too long after that very first hand job. Dirk just brought some that he'd lifted from his sister, and had me put them on. It's that simple.
The bra was white with scalloped trim around all the edges, dainty little straps and underwire cups. I've since learned that I'm not a big fan of underwire cups - they always seem to look like a couple of deflated balloons unless I stuff the cups. And I kind of prefer the natural look as much as possible.
I say dainty straps as opposed to what I call industrial-strength straps. Typical teenage girl bra straps, I guess. Nothing wider than an inch. When a woman gets bigger on top, she starts needing bigger straps to properly distribute the load. But teenage girls, bless their hearts, are small enough and perky enough that their straps can be small and sexy. And that's what I like to wear. And that's the kind of bra Dirk first brought for me to wear.
Now, it was kind of weird, I guess, when he handed it to me and said I should put it on. And I guess at this point, I ought to comment on what happened to the hypnosis thing. Only I'm not really sure. Somewhere along the way we just sort of stopped doing it. At first, the jewelry was there, and Dirk would light the candle to give me something on which to focus, and then the instruction he gave me was that once he put the snowflake necklace around my neck, I would automatically be hypnotized again and think of myself as Snowflake the former cat who was now a human girl. It was a standing post-hypnotic suggestion.
At some point, I guess we both realized that I was faking the whole thing of being hypnotized, and it seemed to quit being a necessary action for us to do what we really wanted to do anyway, which was have me dress in girl clothes and be his girlfriend.
So Dirk handed me that bra and panties, and told me to put them on. Suggested, not told. It's hard to come up with just the right word for how that works, but if you think about me being hypnotized, you'll know what I mean.
The panties he brought out that very first time were white cotton ones, with the words "100% Grade-A Princess" printed across the front. The front, not the back. Sometimes it was hard after that, when I saw his sister, to think about the possibility she might be wearing something I'd once worn.
Anyway, they didn't fit. They were made for girl hips, not for boys, and so we had to tie a couple of knots in the sides to keep them from falling off. Dirk has since gotten much better at picking out panties for me. Of course, his best solution is to just tell me to pick them out myself. That way he doesn't have to deal with it.
So there I was, in the tree house with Dirk, holding his sister's bra and her princess panties, and Dirk telling me I should put them on. So.... uh, well, okay, how do I do that?
I undressed, of course.
I told Dirk to turn around while I did it. And if you think it was scary that first time giving him a hand job, wondering if there would be someone sneak in on us while Dirk had his pants down, you can imagine how nervous I was when it was me, completely naked, followed by putting on panties and a bra.
I tucked my clitty back between my legs because I didn't want the front panel to have a boyish bulge. Oh, and... the back of the panty was a thong, in case you're wondering. So, yeah, Dirk got to stare at my ass a little as I turned slowly, modeling for him.
Bras have always been hard for me to put on the way girls do it in the movies. I can't reach behind me to do the snaps. So I always just put them on backward, with the snaps in front, and then turn them around and slip my arms through the straps. Bob's your uncle.
It felt just a little weird that first time, I guess, when I told Dirk he could turn around and look at me. I mean, I guess wearing jewelry is one thing, but wearing girl underthings means you're really committed. At that point, I realized, there was essentially no going back, and no denying that I wanted to do it.
Sometimes I feel like wearing girl clothes makes me a traitor to my gender or something. Like I've given up on ever being able to be a real man, and have decided to switch to the other team. That's a whole 'nother issue, though, that I don't really want to get into right now. Let's just say letting Dirk see me in bra and panties pretty much told him I was committed to the idea of being his girlfriend, and doing for him everything girlfriends do for the boys they love.
'Cause, yes, I was in love with him. Head over heels in love. No doubt about it. I still am.
As I knelt with my back to him, Dirk said something that literally gave me shivers. He said, "I want to fuck you, Snowflake."
And I guess that's when I first knew for sure that he was as committed to our alternative relationship as I was.
But before he could fuck me, we had to make out a few times. Which we did with me wearing just a bra and panties. There's something about making out with a guy when dressed that way that just makes me feel like a real girl. I've always liked doing it with Dirk, and dressing like a girl to do it just seems to make it feel right.
And there's something about having a guy's tongue in your mouth. That happened the first time we made out. I was in the white bra and princess panties, when I snuggled up next to Dirk the way I was used to doing, and suddenly he was pulling me onto his lap and kissing me. Hard. It was great.
Our lips interlocked, with his upper lip between mine and my lower lip between his, which I guess is the international sign for I-want-to-French-kiss, and almost immediately his tongue was in my mouth. Which must have been okay with me, because my mouth was open. And then my tongue was in his mouth, too. And I remember thinking how weird it was to have my tongue in someone else's mouth, and to be able to feel his teeth with my tongue. And to feel his tongue swishing back and forth and around and around inside my mouth. It was a sexy feeling, no doubt about it.
After making out a few times, and finishing off with me giving him hand jobs, Dirk finally suggested I try getting him off with my mouth. I wouldn't say I was hesitant to do it. From the time I saw him naked that first time, I had this feeling he belonged in my mouth. I just wasn't sure how to bring it up. So when he finally did, I was secretly glad. Finally, I thought, I get to find out what it feels like to have a guy's dick in my mouth.
But not just any guy's dick. Dirk's dick. And to me that made it extra special.
When I was giving him that very first blow job that day, I was already starting to think about what it would be like to have it inside my backdoor pussy. 'Cause I knew that was going to be the next step.
The day it happened I was wearing a little dark-blue polyester skirt that he'd borrowed from his sister. His sister and I were about the same size, other than her hips were bigger, and she wasn't as tall. But when you're wearing her bra and underpants, nobody knows how tall she is, so that didn't matter. In skirts, it just meant that I started wearing mini-skirts right from the start.
I was wearing some of her panties, too, and a black cotton bra. There's something about wearing a bra that you know has been used to hold up real tits on a real girl that's incredibly exciting and arousing.
At the same time, Dirk was laying there with his pants and underwear down around his ankles, waiting for me to start sucking his dick. It was so sexy. Really. It was sexy in that way guys can be sexy when they're not trying to be sexy. He was just all nude and naked, and hairy and aroused. I think it's that aroused thing that gets to me the most. It's like this naked guy, laying there, with this totally obscene indication of his arousal sticking straight up in the air, demanding your attention.
Since it was my very first time sucking a dick, I decided to take my time. I wanted to remember every detail.
His cock was sticking straight up. I remember that. Except it wasn't exactly straight up. It was more like straight up and back a little, so it was kind of pointing at his tummy. So I kissed his tummy a little, completely avoiding his one-eyed monster at first until I saw it starting to pulse and throb for me. I love that look. I love seeing it bounce up and down with every heartbeat. I absolutely love it.
And that's when I knew I really, truly wanted to suck it. I wanted it in my mouth. I wanted to wrap my lips around it. I was totally hungry for it.
I wasn't sure how I could go much slower, once I got my lips around it, so I was careful at first to just kiss it, staying away from the tip, which I knew, once I got there, would go straight into my mouth.
And it did.
Did I mention how sexy and gorgeous Dirk's cock is? Nice size - I love having my hand wrapped around it. Or between my legs where it feels like I can feel every inch of it. But that's getting ahead of the story again. So at first I just kissed it all over. From the base of his shaft to just below the tip. Until Dirk groaned and started pleading, "Just suck it, Snowflake. Please."
It was so sexy hearing him plead like that. What could I do? I started licking the shaft. God, that huge vein on the underside that makes it get so big so fast; how sexy is that? Too sexy. In moments my lips were on the tip, and then the tip was in my mouth. Followed by the entire shaft. Or at least as much of it as I could fit at the time. I've since learned how to deep throat, but, again, that's a different story.
At the time I was able to get most of it, save an inch or two at the base, and... I guess it's a little like French-kissing, only in reverse. I could feel his sexy hardness swirling around in my mouth, touching my teeth, and pressing against the roof of my mouth. So sexy! The essence of a man right there in my mouth. I found if I pressed my tongue up against the shaft, I could feel it pulsing inside me.
I wish... I'd like to lie, and say he came in my mouth. No, I wouldn't like to lie. Liars go to hell. I know adulterers and fornicators go to hell, too, but... I just figure the less sinning I can do the better. You know? So no lying; he didn't cum in my mouth. It would make a great story if he had, but, unfortunately, that's not the way it happened.
After I sucked him for what seemed like forever and a few minutes, he pulled out and jerked himself off, and then came all over my ass and my panties. His sister's panties, I mean. I'm not sure what she ever thought about that, if she ever knew. I made sure to lift his sister's skirt up to my waist so he wouldn't get any cum on that, though.
And God, talk about feeling like a dirty, sexy, slutty whore. There's nothing like hiking up your skirt while a guy jerks off on your ass.
Unless it's hiking up your skirt while he cums inside your ass. But I'm getting ahead of myself again.
So I guess I should just get on with it and tell you all about our very first fuck, then.
A girl's first fuck is always a special moment, something she wants to remember for as long as she lives. She wants it to be special. Meaningful. You're only a virgin once. So you want it to be with someone you love.
Fortunately, I had that with Dirk. There was no question I wanted it to be him. Sometimes when I was sucking him off, or holding him in my hand, I'd think about how truly huge he was, and wonder how in the hell it was ever going to fit inside me. I read a few on-line tips on anal sex, trying to get ready. There seemed to be a lot of disagreement on how to do it with the least amount of pain and stress. In the end, my guess was it was going to be easiest for me if I could be on top - in the girl-superior position. That would allow me to control just how fast and how deep it went in.
The best laid plans of mice, men and tgurls, as they say. In other words, nothing ever works out the way you think.
We planned it for the night of Dirk's high school graduation, since no one expected him, or me, to be home at a decent hour that night. It was summer, and I was just finishing my sophomore year of high school. I was sixteen. Dirk was a few weeks away from his eighteenth birthday. And sexier than he'd been when we first started having sex.
I was wearing my favorite blue satin panties - a special gift from Dirk; they belonged only to me; I didn't have to share them with his sister. They were made even more special by the fact that Dirk picked them out himself without my help. They were bikini style - I told him I liked that style and found it more comfortable than a thong, and it was just as easy when we were making out for him to get his hand inside my bikini panties to fondle my ass as it was to fondle my ass when I was wearing a thong.
I was also wearing one of those denim skirts, which at the time were starting to go out of style, so you could get them cheap at the thrift store, but it was hard to find them in my size. My bra was teal, with the soft cups I like, and was another gift from Dirk. It would have been too much to ask for it to match the panty, but I knew he did the best he could.
We also had plenty of lube. I insisted on that. And, while I'm on the subject, I guess, no condoms. Sorry. No, I don't exactly recommend that kind of behavior, but I trusted Dirk a lot, and the idea of a rubber inside me that very first time just made me want to cry. We'd had oral sex once with a rubber, one day when we started thinking it might be a good idea to be sexually responsible teenagers, and I absolutely hated it. Yuck! I told him after that that if I couldn't trust him without one, then I didn't want to do it at all. I wanted my first time being fucked to be special, and to me there was nothing special at all about having a rubber-clad penis shoved up my backside, so we didn't use one. "I might as well be getting a rectal exam from the doctor," I told him.
So no rubbers. Just Dirk's lovely, gorgeous dick and a whole lot of slippery lube going inside me.
We started off by kissing and making out, getting him nice and hard and horny. I told him I wouldn't let him do it to me until he said the magic words, "I want to fuck you, Snowflake."
Once he said that, I climbed on top of him and started lowering myself onto his appendage, intending to let it penetrate me.
Ouch!
Okay, I tried again. Still too painful I tried again, but it just wasn't working. I was getting so frustrated. And I worried that the longer it took, the greater the possibility of Dirk getting soft and losing the mood.
Okay, so that last worry was pretty much groundless. I don't think I've ever seen Dirk unable to rise to the occasion. But at the time I didn't know that, and I worried he might lose interest if it took too long.
"Turn over," he ordered.
I slipped off him and onto my hands and knees. Dirk got behind me, doggy style, and pulled my denim skirt up. Oh god! I was about to get fucked like a total-slut girl, I realized. I was so excited.
He kept my panties on, but pulled them aside to put his cock inside my opening.
"Go slow," I ordered. We'd already discussed the rules of penetrating me that first time. He was to go no faster than I would allow, about one inch at a time, letting me get used to it before going deeper, until he had every last inch of it inside me. At no time, I insisted, no matter how much I begged, was he to go back out. "I don't want to get it halfway in and then have to start all over again," I said. "And, once we decide to do it," I told him, "I want us to finish it. I don't want to get halfway done and then have to wait and try it again some other day."
So this was the day.
And to this day I can't imagine how he did it. He had the patience of Job, I swear. One inch at a time. A half-inch even. Which meant a dozen or so grueling steps. And I didn't give him permission to start thrusting until he was all the way in and I told him I was ready.
I swore. A lot. Every bad word I could think of. But I was determined. I pushed back, wanting him inside me. All of him. Every last inch.
And after a while, he told me it was all the way in. I mean, I could certainly believe it was. I swear I could feel every inch of it pushing in and re-arranging my internal organs. I think my liver complained the most about the sexy intruder.
The thing that surprised me the most, though, was the feel of his balls. His nuts. Dirk has probably the biggest balls of any guy I've ever known. They're huge. Not quite the size of golf balls, but getting there. And, once he had his cock all the way inside me, I could feel his nut sack hanging down, tickling my crotch.
There was something about that feeling that got me really turned on and aroused. It was like I suddenly knew for sure that I was being fucked by a man - a real man - which meant, of course, that I must be a woman. I mean, what else was there? I'm sure my own balls were back there somewhere too, but at the time, they seemed insignificant compared to what Dirk had.
And then it's like, maybe feeling his balls there somehow completed me. Not that my balls were worthless and pathetic, but maybe... Maybe they were. Maybe part of being a sissy crossdresser is not being a full and complete man, and not having the "cajones" that a real man does. And so you go the other way in some perverted attempt to compensate, and it's only when you finally feel a "real man's" balls there between your legs that you finally feel complete.
I don't know. All I know is it felt incredibly sexy.
So with all of Dirk's dick inside me, and his huge balls hanging down against my crotch, I took a moment to compose myself. It didn't hurt too bad. It had hurt like hell at first, but the hurt was slowly going away, being replaced by sensations of pleasure. In fact, it was already starting to feel incredible. I was getting fucked just like a girl. Life was damn near perfect. "Okay," I said, "Start fucking."
And he did. In. Out. In-out. Faster. Deeper. Harder. It felt so good. I could feel those big balls slapping against my crotch each time he thrust into me. The initial pain had disappeared, and all that was left was the pleasure of fucking. The pleasure of finally being taken as a woman by the man I loved.
Dirk came, finally. Deep inside me. That's where I wanted it. I dared him to try making me pregnant, if he could. He certainly tried, bless his heart.
That was our first time. It certainly wasn't our last. Not even in the tree house. We screwed a lot that summer. Always with me in the female role, and him taking the male role. We both liked it that way; there was no point in changing.
In the fall, Dirk went to college and I went back to high school. The game we enjoyed so much eventually seemed like nothing more than youthful curiosity. Eventually Dirk got married - to a woman - and I did the same.
Different women, of course.
As much as I enjoyed having sex with Dirk, I never really wanted to come out as gay, or transgendered, It seemed like a sure way to screw up a perfectly good life, in my opinion. And so eventually the hypnotism game and everything else we did in that tree house disappeared into distant memory, and the two of us became responsible adults.
After college, Dirk got a job out of state, and moved away, which is where he met his wife. I stayed behind, which is where I met my wife. Years went by, and one day I got laid off and had to start looking for a job again. Imagine my pleasure when I found one in the same city where Dirk was. Of course I took the job, and before long, we were close, close friends again.
Which meant sex again. With me in the female role, and Dirk taking the male role. Just like it had always been.
Only now he doesn't have to hypnotize me.