Diary: My Velvety Undies; and, a Prison Fantasy

That fuzzy lingerie was quite enjoyable.  It's just my size.  It's a little too full, both for my taste and hers.  It covers too much up.  But it's quite fun to wear.  I couldn't stop thinking about it for a few days after I wore it.  Especially that first time.  I came once, and I just had to continue.  I had to get some more.  I came again.  Then later that night, I had to jerk myself again, but I didn't bother to put it on, although it was at the centre of my thoughts the whole time.  I regretted not wearing it.  But I had to be careful: it was collecting little bits of white fluff from my fuzzy bedsheets.  I rubbed as much off as I could, but I figured in the end that my task was hopeless, and that she probably wouldn't even notice.  Nevertheless, I forbade myself from wearing it again until she wore it first.  And she did.  And she didn't notice.  Although she did tell me that I'm not allowed to wear it.

That, of course, only makes me want to wear it more.  I wore it again last night, and thoroughly enjoyed myself.  It had been a while since I had done anything.  I had been dry since Sunday, I think.  So it was a welcome relief.  And I've been thinking of those panties all day.  I want to do it again tonight.  And as a matter of fact, I will.  I'll be wearing them a hell of a lot more than A__.  Isn't that just great?

I was quite impressed with the way those panties caress the crotch, in a way that men's underwear just doesn't.  I can feel a strange sort of erotic tugging at my balls and along the line up to my hips.  It makes me feel so sexy, so girlish.  So BAD.  And that's a good thing.  A very good thing indeed.

It's amazing how often I come back to this.  I find myself coming back here time after time, affirming for myself why I find so much pleasure in wearing undergarments designed for members of the opposite sex.  Is there really anything inherently sexy about the underwear itself?  Intuitively, no; it's what's supposed to go into it that's sexy.  But somehow, I can't help but break into a sweat when I look at women's underwear.  It's so incredibly sexy, so naughty.  I look at silky, lace-trimmed panties and I can't help but be turned on.  There doesn't even have to be anything inside them.  Just the panties are enough.  This raises an intriguing question, to which I will now attempt to find the answer: is it the panties themselves that turn me on, or their association with things feminine?

Let me see.  There is a clear connection with the femininity of panties.  I wouldn't care for them at all if there weren't.  But the question is whether the femininity comes from the fact that girls wear them, or is it inherent in them?  In that case, the panties are a source of femininity, because some panties are sexier than others.  I would much rather wear a skimpy pair of lacy, stringy panties than both the big massive ones that mom wears and even the undeniably sexy fuzzy red panties in my drawer.  So there is something to the panties themselves.  Women, however, don't draw their femininity from the panties, although they do accentuate feminine features.  A girl would be about as sexy with them as without them.  Although I must admit that I prefer seeing A__ in her underwear than naked.  She is smashing naked, but in underwear, she's somehow sexier.  I suppose that has as much to do with my underwear fetish as it does with their accentuation of her features.

So I suppose I must conclude that the panties themselves turn me on, because they are, strangely enough, inherently feminine.  But why are they inherently feminine?  I suppose it must be because they are shaped in a way that makes a woman look fantastic.  But that's mostly psychological.  Why associate lace or silk with women, and not men?  It seems rather arbitrary.  But in my mind, there is nothing arbitrary about it.  It's not just the silk, or the softness, or the lace, but the overall shape of the panties that counts.  You know when you look at it that it's designed for a girl's body.  It's not just the crotch, either.  Something about the trim usually means sexiness, too.  The fuzzy panties have no lace, no silk (except for something soft on the inside) but are still sexy enough.  The shape has everything to do with it.  A bikini panty is incredibly, exquisitely sexy, too, and it has no lace, no silk, just a high cutting shape.  I still have a craving for a bikini, but that's usually overridden these days by a powerful need for varieties of underwear.  I still want to wear A__'s regular panties, which are by no means spectacular.  They just look so fun.  It must be psychological.  The shape alone can't possibly account for it all.  But in a way, I guess it does.  Silkiness and lace are just an added bonus.

Another question is this: why, if I am turned on by the underwear, do I absolutely need to wear it?  It just wouldn't be pleasurable if I didn't slip into it.  Sometimes, the most intense moment of my pleasure comes when I imagine that when I am done, I can slip into my girlie underwear and go to sleep, as if that's my normal undergarment.  It's incredibly enticing, incredibly erotic.  The whole fetish for underwear is connected to an overpowering desire for femininity.  I want to discard my masculinity, which all men hold so dear, in favour of femininity and women's underwear.  I want to laugh in the face of all the men who would disown me if I ever showed the slightest trace of girlishness, as I wontonly shake off my manliness and gamboll freely with the girls, in their clothes.  I want to abdicate my heavy responsibilities as a man and take on the playful female spirit of sexual abandon.  I want to make myself pretty, and sleek, and lithe, and curvy, in revolt to masculine norms.  I just want to escape that fragile male facade and embrace the freedom of being female.  Girls don't have rules against wearing certain types of clothes.  Girls don't have rules against doing things that men do.  Girls can be as feminine as they please.  Men can't be feminine at all.  Mind you, girls can't really get away with being masculine, but they get away with it far more easily and far more often than men get away with being feminine.  It doesn't really have anything to do with it.  

I still have so much trouble putting my finger on it.  Femininity arouses me to the utmost degree, yet I have transferred that arousal somehow away from particular women to a symbol of their femininity in their underwear.  From an intense heterosexual urge, I have extracted an overpowering urge to be feminine.  Something about the perversity of it arouses me even more.  Something about the sheer taboo of it makes me want to do it that much more, makes me enjoy it that much more.  The fact that I should feel shame, and that I have felt shame, for doing it, makes it so arousing.  I should be ashamed of myself, because I wear women's clothes.  But so what?  What does that mean?  If anybody asked me, that's how I would defend myself.  So what if I wear women's underwear for pleasure?  What does that entail?  Am I somehow less masculine now?  Years of doing it hasn't changed me into a woman or a homosexual has it?  Was I any more sexy a year ago than I am now?  Your not knowing that I secretly wear women's underwear didn't make me seem girlish, did it?  Of course not.  I'm not girlish.  But secretly, I would think about how I wished each time that it did make me feminine, how I wished each time to throw away my manhood forever and never look back.  The idea of wearing women's underwear permanently has often enticed me.  Always enticed me.  I know that my arguments are hollow, because every argument I use to defend myself has an easy answer.  YES, you are less masculine.  YES, it has changed you into a sort of pervert.  Normal people don't do that.  Normal people wear their own underwear.  It's weird and it makes me uncomfortable to think that you dress like a girl in private.  What other perverted thoughts do you think?

But that's part of the dream, isn't it?  I dream of being forced into women's underwear, and finally succumbing to the pleasure of it, and finally becoming feminine, and ultimately female.  I have no choice but to accept how pleasurable it is, or I will go insane.  The way I see it, I know something that everybody, including women, knows: wearing sexy women's lingerie is incredibly arousing and gratifying.  Women know it, and they wear it, because it makes them feel sexy and attractive.  Men know it because they see women wearing it, and becoming sexy and attractive.  But what they don't know, or rather what they are afraid to admit, is that even men would feel sexy and attractive--exactly as women do-- when they wear it.  Men would feel sexy and feminine by wearing women's panties.  And that's what they fear.  They just know that they would love wearing their sweetheart's underwear.  And that's exactly why they don't do it.  It could become habit-forming.  They might start wearing it every day, and eventually become transsexuals.  That's what they're afraid of.  Women are afraid of it, too, because they don't want more girlfriends, they want men to be masculine; they fear that their men will want to become women.  Funny thing is that all of these fears are not only completely justified, but perfectly true.  Most men will probably never put on women's underwear, because they don't want to have to deal with suddenly wanting to repeat the experience compulsively.  They don't want it to make them girlish.  They think that wearing lingerie just once will make them turn into complete sissies, who'll keep coming back for more.  The beauty of it is that they're absolutely right.  Just look at me: I can't stop.  I always want more.  And this has been going on for almost twenty years now, since I was five years old.

The difference is that I'm not afraid anymore.  Now I'm only marginally afraid that anyone finds out.  The fear has withered away because I've become desensitized to wearing women's clothes now, and it's almost routine.  But I would never want anyone to find out.  That would be disastrous.  But I want to keep doing it forever.  

Again, a cheesy scenario:  I am captured by a bunch of girls.  They are playful and sexy and beautiful.  They think it's great to have a man with them.  They have no respect for me, though, because I am the enemy.  They strip me naked and make me wear their clothes and makeup.  They turn me into their mannequin.  And they laugh at me.  But I can't help but enjoy it.  And they take notice.  And they torture me, and force me to come all over myself as I wear their outfits, particularly their lingerie and bathing suits and sexy stuff.  Naturally, I only model their sexy stuff.  They keep tempting me and mocking me, for years, but I hope for a rescue.  Finally, I can't take it anymore, and I succumb.  Before, I never let myself come.  But now, I let myself go.  I accept the pleasure.  I don't prevent myself a release anymore, and I start coming all over the place, and really enjoying it.  No.

They capture me and start dressing me up.  I don't react.  I just feel humiliation.  I am shamed.  I, a big powerful man, am dressed in pretty little silks and flowery laces and bows.  I secretly, even to myself, feel the pleasure of a hard-on in my crotch, but I resist it at all costs.  It just feels so soft, and so tight.  It's the girls, I tell myself.  They're causing this.  But I know in my heart that it's the clothes I'm wearing, tight on my pecker, and soft and pretty, that make me horny.  They notice, and rub me down until I come inside the clothes.  I am completely ashamed, as they make fun of me in girly clothes, apparently enjoying myself.  they do this again and again to me, and I am always ashamed.  I desperately try to stop them from pleasuring me, but I can't help but feel pleasure.  By the second or  third time, they stop, and they don't do it anymore.  I long for the pleasure, but I can't ask them.  I am a prisoner, and I don't have rights.  But they have me in their playroom.  This is where they prance around in their underwear, modelling stuff for themselves, for each other, because girls like to do that type of thing.  Their clothes are everywhere.  Tempting me.  They leave me alone there every night with their lingerie all around me.  I am going insane, so I put some on, and masturbate in it, completely revelling in the pleasure.

Of course, they don't notice.  They have apparently lost interest in me.  They don't make me wear their clothes anymore.  They don't do much to me anymore, just keep me there to watch and drool.  Nobody knows where I am.  They think I'm dead, they tell me.  I'm not going anywhere.  About a week has passed, and I have only begun sneaking into their panties.  They forced me only on the first day.  They keep me naked, and shake their butts and tits in my face.  They love to bug me.  But they think they're torturing me.  I secretly have my fun when I come all over their lingerie at night.  

I am always careful that they don't notice.  I don't want them to know that I am having fun, or they will take that fun away from me.

One morning, not long after I have gotten into a nighttime routine of prancing around in their underclothes, they wheel in a TV, and they draw my attention to it.  They make me watch videos of myself.  At night.  Poking around their clothes.  Putting some on.  Strutting around the room like one of them.  Dropping to the ground in a mass of sexual pleasure, rubbing myself all over their clothes.  Coming.  I turn my head in embarrassment as they stare at me with sly grins.  They know about my pleasure.  I'm not so upset that they know that I was pleasuring myself, but that they know how I was pleasuring myself.  I want to vomit.  I must be purple with shame. 

One of the girls comes prancing over to me, and hands me a matching set of panty and bra.  It's white, skimpy, and very sexy.  It's brand new.  "This ought to look soooo good on you. . ." she bubbles.  The other girls giggle.  They coax me to put it on.  "We're not doing anything until you put that on," they tell me.  "We'll take all of our stuff out of here if you don't do as we say, and you'll be left with nothing."

I look at the underwear in my hands.  It's so sexy.  I am trembling in both dread and anticipation.  I look at the underwear, and at the girls, and back at the underwear.  I don't know what to do.  Should I forsake my masculinity right here and now, or hold out, and maintain it as powerfully as I can?  As if she could read my mind, the one who gave me the underwear says, "We know you love to wear girls's stuff.  You have very little masculinity to cling to anymore.  You are beyond salvation now.  You're one of us."

I burst into tears of rage, frustration, and shame, and wring the underwear in my hands.  It feels so soft, so silky.  It's so delicate, so. . . feminine.  I look at them again.  I am about to throw the lingerie across the room, but I can't.  I don't want to let go.  I know that I am caught.  I can't go back.  It would be murder for me to give up on my new found pleasure now.  But what if I can shake it?  What if I can save that last shred of maleness?  I look at the lingerie again.  Then I look at the girl who gave it to me.  Amy is her name.
"Will you at least look at it?" she implores.  She is standing right in front of me.  She's wearing nothing but a matching set of purple lace.  She's very sexy.  Very pretty.  Her long, slender legs are beautifully shaven.  Her titties look so happy in their tight little garment.  The other girls are all standing together in a huddle, playing together.  They casually touch each other's legs, arms, hair.  I  subconsciously stretch out the bra in front of me and look at it.  It's silk and lace.  A strong silk.  The panties are very high cut, I notice, as I stretch them out, too.  A frilly little elastic forms the waistband that holds together the silk pouch with the lace trim.  Impulsively, I slip into the panties, shaking all over, almost tripping as I step into the second leg hole.  The girls encourage me.  "Atta girl.  That's the way."  Amy helps me put my bra on.  She has a huge grin on her face, and I sheepishly smile back to her.  "You look beautiful," she says, as she takes me by the hand and flits with me in tow to the others.  

"Girls," she says, "we have a new girlfriend.  This is Bobbie.  She's new at this, so we have to show her how we do things here."  The other girls all introduced themselves, and sized me up as if I were one of them.  They were very friendly.  I was going nuts with anticipation.  I was so horny. 

"First, we have to let Bobbie get comfortable.  Shall we?"  The girls surrounded me, and started rubbing up against me.  They weren't sexual or erotic about it.  Just friendly.  I was in absolute heaven.  They avoided my cock, my absurd cock that stuck half out of the panties, but which felt so good in there.  The girls made me feel so feminine.  They stroked me like I would a girlfriend, with attention to my tits, butt, thighs, belly.  After several minutes of this, they stop.

"Now Bobbie," says Amy, "we're not all that convinced that you want to be one of us.  Show us how much you appreciate your new clothes, and we'll be happy.  Go on, just like you did at night."


I sheepishly dropped to my knees, and then to the ground, and rubbed myself silly, although quite self-consciously, and uncomfortably.  It was my first time in front of them, and I felt a little uncomfortable.  I was having doubts.

"I know you're having your doubts.  But trust me.  Just follow your heart."

I couldn't help myself but feel tremendously proud at that moment, and I abandoned the last vestiges of my maleness.  It felt so good, and I didn't want it to stop.  But I came, and I felt ashamed again.  

Here I was, wearing a matching panty and bra, with come all over me, in front of six beautiful girls in their underwear.  I felt ridiculous, and a shame to my gender.  I blushed, and I wept.  Hard.  The girls cheered as I masturbated.  I was so ashamed.  I rolled off my panties, and the girls were silent.  I was sobbing.  "I can't go on with this.  It isn't right," I bawled.

Amy frowned and took away my panties.  Well, then, I guess we'll have to take back our lingerie.  Let's go girls.  They packed up all their things, and left me there naked and crying.

Every night, I longed for the underwear.  But I chastised myself for being so weak.  I couldn't stop thinking about it.  I longed for them to play with me again, and I never ceased lamenting my sorry state.  They only visited me rarely now.

But one night, Amy snuck into my cell and awakened me.  She shushed me, and gave me the same underwear I had worn before.  "Take this.  I know you want another chance.  It's not too late."  And she left me there with the underwear.  I was shaking again.  I could hardly control myself.  I put them on, and shook my booty all night in it.  But I was still ashamed. . .

* * *


To make a long story short, I eventually realized that the pleasures of femininity were far greater than my noble upholding of my masculinity.  I stopped making myself feel guilty about wearing that exquisite underwear, knowing that I could never be the man that I was.  Uncomfortably, I accepted my plight as a transsexual, and began to enjoy myself.  The girls took me into their group again, and I was one of them.  They showed me how to become female.  I learned to shave my body, and to walk and talk like them.  I was no longer a prisoner.

Then one day, the girls let me see a visitors.  A group of men from where I came from had found me.  Apparently, they had known that I was captured, not killed, and that the enemy had me.  They were negotiating for my release.  My former enemy told them that I was here by choice, and that I wouldn't leave.  They insisted on seeing me.  

They were appalled.  They recognized me, despite the breast implants, and the effeminated body.  I still had a penis.  The men couldn't keep their eyes off me, even though the real girls were all also in their underwear as usual.  they giggled in the background.

I told them that I wanted to stay, that I was comfortable here.  They were trying to force me to return.  I apparently had no choice.  So I went.  It was a long voyage home.

In short, they made me discard my new clothes, and gave me yucky men's clothes.  But at night, I snuck into each man's cabin, and showed him the way.  I fucked them all.  And they loved it.  They thought I was a ship's maid or something.  I managed to get some panties back, and I fucked them all.  This way I convinced their leader to turn back, that all the sex they wanted would wait for them on shore.  All of those gallivanting beauties were theirs.  They turned back.  Now they're all prisoners.  And they're all learning my lesson: that girls rule.