Fiction: The Ultimate Sexual Experience, Part 3

[Part 1] [Part 2]


That's pretty well how I spent the next week or so.  I wore lingerie all day and all night.  They treated me like a girl.  They did their best to make me feel like a girl.  And at the end of every day, we all cuddled together, wearing sexy lingerie.  The first few days, I was tentative about choosing which outfit to wear.  Presented with a matching bra and panty set, a teddy, or a nightgown, I had to pick one.  "What do you want to wear today?"  they would ask.  How could I say that I wanted to wear any of it?  Why would I want to wear women's underwear at all?  How could I go about choosing, anyway?  Still, I felt that I did have a preference: I feel turned on looking at one or another of them.  I suppose that there's something sexy about women's underwear in and of itself.  They kept pestering me.  "See?  He likes the matching bra and panties."  "Wouldn't you rather wear the teddy?"  "Leave him alone!  He obviously wants the bra and panties!"  I couldn't stand it.  But somehow they could tell which one turned me on the most.  And they gave it to me.  And they made me wear it.


My hands would shake as they got hold of them.  Normally, I would be unhooking these, or slipping them off of female hips.  I always did love the feel of silk and satin, and the feminine look of lace.  I always did love the look of feminine underwear.  I was getting a very close look at it, and it was bringing back all sorts of memories of sexual encounters when I would be looking at sexy girls wearing things just like this.  The panty and bra set was femininity itself.  Something about its shape, about the lacy trim, about the delicate elastic, all of it made me quite horny.  I held in my hands a most potent symbol of female sexuality: the style and design of the outfit is made to highlight feminine sexual traits.  It's made to make girls look even sexier than they are.  And I had to put it on my masculine body, a body that has been in contact with countless hordes of females wearing just this kind of sexy outfit.

They always had to push me into putting it on.  I mean, there I stood with a powerful female sexualizing tool in my hands, and I just couldn't make the connection to my own body.  They just couldn't connect in my mind.  They would snap the whip at me to get me going.  I was so confused.  I didn't really know how to go about putting it on, except for what I had seen the girls do here, and everything else I'd seen over the years.  I just stepped into the panties like I would my own underwear.  Except I hesitated.  In part, I didn't want to stop looking at the girlish garment I was sliding up my legs, particularly the crotch.  But I had to go up, all the way to my own crotch.  It looked just awful contoured on my male body.  But it was still feminine.  It hugged around my hips and butt just like it would on any woman.

Next, and most difficult, was the bra.  I didn't even know how to begin.  Danielle had to show me the first time, because she didn't want me fooling around for too long.  I guess she thought that I was procrastinating.  She took me through it step by step.  I couldn't help but stare at her incredible body as she showed me how to put on a bra.  She started off by holding it up straight, and right side up, so that the top was on top, and the outside facing away from her.  I did the same.  Then she grabbed each end and wrapped it around her waist, with the two ends at the front.  I did the same with mine.  She clasped the two little hooks.  I clasped my two little hooks.  It felt tight and smooth around my waist.  Then we turned them around together, in unison, and pulled our bras up by the shoulder straps, putting our arms through them as they came up.  I was so embarrassed when I realized that we both snapped the shoulder straps when we got them on.  I did it completely by accident.

Then, when I had it on, they told me to feel my underwear against my skin, until they had me dirty dancing like a girl in front of them.  I felt so incredibly horny with all this girlishness around me.  I couldn't get over having something so feminine on the source of my masculinity.  I wanted to feel every bit of that femininity all over me.  The outfit seemed to feed on my every move, seemed to become more and more feminine with every undulation of my hips.  Every touch reminded me of what I was wearing, and how girlish it made me.  Femininity was rubbing off on me.  I was moving more and more like a girl, and it felt better and better.  I think they could tell that I wasn't hamming it up anymore.  I could feel the panties and bra making me more girlish by the second, and I couldn't resist.  Worse, I was relishing it.  It just felt so good, I wanted more and more.  I knew what was happening to me, and with every second, I wanted it more.  While I wore that bra and those panties, I wanted to besmirch my manhood.  I wanted that outfit to effeminate me.  I wanted to feel like a girl.  


Those girls were smart.  They knew what was going on.  I didn't, yet.  They didn't let me come until the end of the day.  As I came, I experienced the most intense sexual experience of my life, and I knew it.  After I came, I was so incredibly degraded.  I wasn't a girl.  It was all an illusion.  I had worn women's underwear all day, looking like a freak, and wanting desperately to be feminine.  They had devastated my manhood; or rather, they had made me do it all by myself.  I never said to them how I felt all day, but there's no mistaking my actions.  I willfully pranced around like a girl.  I looked forward to wearing more lingerie as I did it.  I had abandoned manhood that day.  They knew that I had.  They also knew that there was no turning back.  I hoped beyond hope that there was a way out.

I lay there in a pool of my come when I realized this.  I was still male, still wearing women's underwear.  They kept me from taking it off.  I resolved then and there that I would never let them take me for a ride like that again.  I would not play their game the next morning.  If they insisted, I would leave.

The next day, as you no doubt know, didn't go quite as I had planned it.  I was forced to choose another outfit for that day.  I was still wearing the bra and panties from the day before.  Oh, how weak I was!  I didn't have the guts to tell them off.  They were still so beautiful.  They brought out the undies again, and I was captivated again.  It was far worse than the day before.  I had a definite desire to wear a pretty, lacy teddy.  I tried to deny myself.  I really did.  But they could tell that I wanted it.  I needed no help putting it on.

The next day, I had resolved the same thing as before.  I practically wept when I slipped into another gorgeous panty and bra set.  I didn't want to stop.  I was feeling so good when I wore their underwear.  I so desperately wanted to never take it off.  Until I came.  Then I never wanted to see women's clothes again.  Then the next morning, I wouldn't be able to resist another shred of silky panty.  Pretty soon, I wasn't just pointing at just anything to get the ordeal over with; I was begging to wear specific items of women's clothing.  At first, they would each bring something out, and I would take a long time to waffle it over before they finally figured it out.  Within a week, I was whispering coyly that I wanted the black silk teddy, or the red lace panty and bra.  "Ummm, could I please have the, uh," I would start, stuttering, mumbling.  


"You'll have to speak up, Pamela would say.  


"I'd like the, uh, the black silk teddy."  


"You'd what?"  


"I want the black silk teddy," I would say louder, blushing.  


"Why, what for?" they would ask.  


"I want to wear it," I would whisper.  


"Why?"  


"Because it feels nice."  


"What do you mean it feels nice?"  


"It feels sexy."  


"Hmm.  You're right.  It sure does feel sexy, doesn't it?  But it's made for girls to wear.  You're not a girl, so you're not allowed to wear it."  


"Please let me wear it."  


"But you're not a girl.  You have to be a girl to wear it.  Do you want to be a girl?"  


I would hesitate for a few seconds.  Then I would blush and say, almost inaudibly, "yes."  They had me.  


"Well, in that case, we'll let you wear it."  


And I slipped into it and reveled.


After that it got easier and easier.  I had nothing to be shy about anymore.  They offered me lingerie to wear, and I chose it.  It was all I wore, and all I wanted to wear.  Except when I came.  When I came, I wanted to crawl into a hole.  But I even got used to that; or rather, I came to terms with it.  Somehow.

But my new-found hobby ended abruptly one morning.  The girls came in as they had for the past two weeks, but didn't offer me anything to wear.  

There was something dangerous about the situation.  I had no direct access to women's underwear anymore.  As far as the girls were concerned, I didn't have to wear lingerie anymore.  They just wanted to have sex now.  

It was very difficult the first day.  I was clumsy.  I couldn't just fuck the shit out of them anymore.  I wanted them to stay in their underwear, so that I could play with the elastics.  It was such a let-down from the days previous, when I, too, pranced around in silky panties and bras.  I still wanted to dress up.  I mean, it was just so fun.  But it never came into the program.  I was embarrassed to ask.  But I was desperate.

"When do I get to wear your undies again?" I asked.

"Oh," answered Pamela, "That's over now.  We want to move on to something else."

It didn't sound like I'd ever wear women's clothes again.

I couldn't sleep anymore.  A part of me was extremely relieved that this problem I had had been taken out of my hands.  I wouldn't be pressured into wearing women's clothes again, so I would never do it again.  I would never damage my manhood again, because I had no access to women's clothes.  Yes, at one point I was very thankful of that.

It didn't last very long.  The girls weren't even mentioning it anymore.  I felt ashamed.  I couldn't ask them, because I would be completely embarrassed.  Yes, even though I was there for the ultimate sexual experience, and even though they were whores, I was afraid, deathly afraid to ask.  They would think less of me, I thought.

I had to take matters in my own hands.  Every night, I needed it more and more.  I sweated in my bed thinking about it, dreaming of wearing something girlish.  I felt like I was missing something.  I dreamed of wearing bikinis and one-piece swimsuits.  They had never let me wear any before.  I wanted to, desperately.  I felt that I could never be completely effeminated if I never wore it.  I fantasized that wearing a woman's bathing suit would push me that much further over the edge, and make me that much more effeminate.


The plan was so simple.  Three gorgeous sluts lived here in the same house with me.  All I had to do was sneak into their bedrooms, and steal whatever I wanted.  I planned it for days.  They just wanted to have sex, but I was staking out the room.

I waited until nightfall.  I needed that bathing suit.  I was sweating again.  I had left Danielle on the couch, where she fell asleep.  I carefully snuck into her room.

Once inside, I gave myself little time to act.  I hurried to her dresser, and rifled through her drawers.  I found a very nice silky smooth swimsuit, very sexy and high cut.  I stuffed it down my boxers and shuffled back into my room.

It took me a few minutes to put it on.  First, I wanted to make sure that no one was coming.  Then I examined it, to relish in all of its wonderful girlishness.  I put it on in the dark, under my covers.  It was incredible.  I felt so effeminate.  It was everything I had wanted it to be.  I could feel my masculinity choke in the tight spandex.  I rubbed my crotch against the covers as I felt my body all over.  The whole time I thought to myself that this was going too far, that I could never recover my manhood now.  I mean, I had worn all sorts of lingerie before, and I had been masturbated in it and came in it, but it was always at the insistence of others.  If I'm forced to do it, I can't be totally responsible for my actions, no matter how much I like it.  But this time, no one forced me.  I wanted it, and I went out and got it.  Nobody even knows about it.  And this very thought that I am damaging my masculinity beyond repair makes me feel even more effeminate, gives me even more pleasure, makes me want to obliterate my gender.  I don't ever want this feeling to stop; it feels so much better than sex.  Maybe this is how a girl feels when she's fucking...

Suddenly, I'm stopped dead in my tracks when someone opens my door.  Claudia is sneaking in here for some reason.  She thinks I'm asleep.  I lay still as a log.  She looks around a little, turns around, and walks out, closing the door behind her.  My heart pounds like a jackhammer.  But I slowly resume, and work my way back to a fever pitch, thankful that I hadn't been caught.  How wonderful it must be, I imagine, to be a woman!  And I affirm to myself my desire to become a girl, and come all over myself and the swimsuit.

Now I'm in trouble.  I can't bring this back to Danielle's dresser in such a condition.  It's filthy, and she'll know immediately what happened to it.  But I can't avoid replacing it, or else she'll miss it.  And Lord knows, I don't want anyone to know about this now.  I don't want to be a girl anymore.  I just can't understand how I got myself into this situation.

Clearly, I must take the chance that she won't miss it.  I can't put a dirty bathing suit back into her drawers.  I have to either destroy it or hide it.  Again, I can't destroy it without risking getting caught.  I stuffed it under my mattress.

As much shame as I felt after that experience, the very next night I wanted more.  All day I worried that Danielle would notice her missing bathing suit, or that someone would find it under my mattress.  I couldn't stop thinking about how much pleasure I had derived from my little crime.  And no one seemed to have noticed.  Sure, I was embarrassed after, but so what?  I had to expect that, considering what I had done.  And what had I done?  I had worn women's clothes and liked it.  Immensely.  The more I thought about it, the more I wanted to relive the experience.  I wanted to be a girl again.  So that night, I dug it out from under my mattress and masturbated again.

Again, the same result.  I was always ashamed.  It was like being brought down from a daydream, except that there was that shame, that gruesome shame, that made me regret my pleasure.  I knew that it was unnatural at the time, and I treasured it for that reason.  It made me so much hornier to think that I wanted to dress like a girl, and that it's socially unacceptable for me to do so.  Imagine what it would do to my image as a macho stud!

Unfortunately, I started getting sick of the bathing suit.  I needed more!  I dreamed of wearing lingerie again, and wearing a garter belt and stockings for the first time.  Soon, I had a basic collection under my mattress.  And no one seemed to be the wiser.  All day, I fantasized about wearing what the girls were wearing.  Sex didn't interest me so much anymore, except that my girls wore such sexy underwear.  It was only a matter of time until I got busted.

I had never felt so much shame in my life.  Pamela caught me one night while wearing her lingerie that I had stolen.  She noticed that it had gone missing, and all three of the girls staked me out.  I was fully into it when they knocked on my door.

"Yes," I answered, because they knocked loudly and persistently.  I could never have slept through that.

"R__!  Quick!  Come out!  There's a fire!"

I was shitting bricks.  I couldn't come out now, dressed like a girl.  "Hold on!" I answered.  "I have to get dressed.  There was probably a hint of a moan in my voice.  I was trying to pull off my panties, unable to get past the garter belt, when they all burst in and tore the covers off my bed.  My secret was exposed, for all to see.  And they all giggled at me.

They made me get out of bed.  I stood in front of them, even more self-consciously than ever before, wearing a black satin bra and panty set, garter belt, and stockings.  They had never made me wear a garter belt or stockings.  I stood there wearing both, and everyone in the room knew that I had put on the whole outfit of my own initiative.  And everyone in the room knew that I had worn it for my own private pleasure, and not to entertain anyone but myself.  They stood across the room, staring at me, decked out all effeminately.  They tsked, pointed, commented to each other.  I wanted to hide.  They had me cornered.  I wanted to take everything off, but I knew it was no use.  They already knew.  There was nothing I could do.  Finally, they spoke to me: "Oh, R__!  We thought you were so macho and sexy and masculine!  And now, now, you're dressing up like a girl!"

That comment made me blush.  I was so ashamed.  I curled up in the corner, mortally embarrassed.  The girls all came to comfort me there on the floor.

"Why did you do it?"

I couldn't answer.  They kept cajoling me, trying to get an answer out of me.  They seemed sincerely concerned and sorry.

"Is it because you're gay?"  


"Is it because you have some kind of fetish?"  


"Were you doing this all along?"  


They didn't even understand me.  They had introduced me to it, but they had no idea that this had happened because of them.  I started to cry.

"There, there, R__.  There there."

Danielle took me in her arms, and I wept on her shoulder.  "It's okay, R__.  It's okay.  We don't mind.  We just wish you had asked us, that's all.  We don't like you stealing from us."

"That's right," cooed Claudia.  "It's okay.  Don't worry, R__, we're not mad at you."

I sobbed some more.  I was a freak, and they knew it.  I still hadn't taken anything off.

"Maybe you should talk about it," urged Pamela.

I looked Danielle in the eye, still crying, and could see how honestly she cared about me.  She really did feel sorry for me.  She really did forgive me.  So did Pamela and Claudia.  And that's when it all came out.

"I just wanted to be sexy!" I cried.  "You girls get to strut around in all this sexy stuff, and I wanted to feel sexy too!"  I buried my head into Danielle's shoulder again.

"There, there!"  She giggled.  "It's okay.  I'm glad you think we're sexy.  But why did you want to wear our undies?  How does that make you feel sexy?"

"I dunno," I sobbed.  "It just does."

"You know, R__," Claudia whispered in my ear, "you do look kinda cute in that outfit."  

I giggled.  I was tickled.  "Really?"

"Oh, R__!  You're adorable!"

"You really mean it?"

"We sure do!"

"So you don't mind?"

"Well, we'd rather you wore your own lingerie."

"My own lingerie?"

"What, don't you want to wear sexy underwear all the time?"

"Yes."

"Then you'll need your own wardrobe, won't you?"

"I guess."

"Cool!  That means we get to go shopping!"  The girls all whooped and giggled together.

"You'll buy me some lingerie?" I asked, incredulously.

"No, silly, you'll buy your own.  We wouldn't want to pick it for you.  You know what you like."

"But I can't go into a lingerie store and buy undies for myself.  They'll think I'm a weirdo!"

"Why would they?"

"Because I'm a man, and I'm buying all sorts of stuff!"

"What makes you think they'll think you're a man?"

"What do you mean?"

"You do want to be a girl, don't you?"

I hesitated.

"Well?"

"I guess."

"Then we'll have to make you into a girl."

With that, they all picked me up off my feet, and walked me to the bathroom.  For the first time, I saw myself in the mirror.  I was a pretty gruesome sight, with my body hair sticking out all over the place, and my misshapen body distorting the femininity of the lingerie I wore.  In contrast to the girls, I looked just repulsive. 
"Let's get you naked," said Pamela, as she snapped the catch on my bra.  Before I knew it, I was stripped naked.  "We've got lots of shaving to do," said Claudia, coming towards me with a razor and some shaving cream.

When they were done, and I stepped into my stolen lingerie, I couldn't recognize myself.  Suddenly, I had very pretty, effeminate legs.  My belly was beautiful, even though my waist was too large in proportion to my hips.  My body looked almost female.  "Wow!  We're almost there!" giggled Danielle.

Then I slipped into a tight mini-dress and the girls made up my face.  I stuffed my bra with foam and toilet paper, and my tits looked really pretty.  Not only did I feel sexier than ever, I even looked like a beautiful girl.  I couldn't stop posing.  Then they gave me a pair of pills.

"What are these?" I asked.

"Those are female hormones.  You take enough of those, you'll have real tits and a nice waist."

My heart pounded as I tossed them into my mouth and swallowed.  This time, there really was no turning back.  It wasn't just fantasy: it wouldn't end when I come.  I was about to buy myself a wardrobe of women's clothes, and I had popped pills that would transform me into a girl.  I was very excited.  I knew that I could never be a man again, and that very thought made me hornier and hornier, and made me want to never look back.  

So there I was, standing a good foot taller than Danielle, Pamela, and Claudia, my muscular build almost bursting out of a mini-dress.  I was dressed like a girl, from inside out, down to the very underwear.  I had shaven off all my body hair.  I wore makeup and styled my hair.  I, who once prided myself on being a great macho stud, now pranced in public as a woman, to go shopping for feminine wardrobe, yet.  I, who had striven my entire life to be the most masculine man alive, had just willingly taken pills that would infuse me with female hormones that would metamorphose my proud manly body into a sleek, slender, girlish body.  

And how did I feel about it?

Fantastic!

It was then that I knew how right this was.  I stepped out in public as a girl, and I felt sexier than I ever had as a man.  For all those years, I had wanted to be the master of the female body.  I wanted to show womankind what pleasure was all about.  But I really knew nothing.  These women had shown me.  I, who had done everything imaginable with so many different women.  They showed me the ultimate sexual experience, and I was hooked.  Only now could I truly begin to know how to please a woman, because I would be a woman.