I guess I should have known something was wrong, because when something sounds too good to be true, it probably is. But I had so much fun with this girl that seemed to have a genuine interest in me. We were both the third wheel in our groups of friends that we arrived with. And as her friends seemed to like my friends, the two of us started talking, and somehow we clicked.
I'll be honest here. I'm not much of a Casanova. As a matter of fact, I get so shy when girls talk to me, that they call me a nerd, and find someone else to talk to. But not Millennia. A strange name, but it rolled off my tongue so deliciously, she had to laugh each time I said her name.
She was into basketball, like me. Played a serious game of Smash Bros, or so she claimed. And she liked fashion. As a guy, you typically don't acknowledge that, but again, it was like I could tell her anything and she didn't judge. As a matter of fact, we had a great time discussing how some people were dressed.
Of course it didn't take her long to uncover my leather fetish. The simple fact that she was wearing a red leather skirt had kept me going early on. And by now she wanted my hand on her as often as I could. It was just the two of us at the end of the bar, with our backs to the wall, so nobody could see us frolicking.
She wanted to know why I wasn't wearing any myself, if I loved it so much, until I finally confessed that it was skirts and dresses that gave me the hots. If only she knew I was wearing leather underwear. But I couldn't tell her, because technically it wasn't male underwear, as that didn't have my attraction.
Of course she found out. It wasn't a one way street, with only me touching her skirt. I guess she wanted to know the effect it had on me, and suddenly her hand disappeared in my pants, straight on my leather pantied dick.
That should have been the end of it, I figured. Instead, it was the beginning of something new. She wanted to know what exactly I was wearing, and I confessed, unable to lie to her. And not only did she appreciate it, she liked it. Very much!
She compared me to herself, which I thought was ridiculous, as she was beautiful, and I was a nerd. But she used to be a nerd, she said, that's why she was still the third wheel with her friends.
Eventually she coaxed me to feel under her skirt, and where I had hoped to find that she was also wearing leather panties, my fingers touched a smooth plastic tube between her legs. And she confessed that was the last piece left of her manhood.
I guess I started my story saying something like “if it sounds too good to be true, it probably is”. This girl, that I really fancied by now, was a guy like me. Or was she? Or, as she suggested, perhaps I was more like her. Wasn't I wearing girl's panties?
She hadn't judged me. So why was I judging her? I guess it was a shock, but I had to agree how much fun we had together. So I told her it didn't matter to me, as a matter of fact, that was probably the reason why I wasn't so shy with her. And my dick was still hard…
She became serious suddenly. She had thought of me as a new friend. Maybe to go to a game. Or play some video games with. But, if I didn't mind her little secret, could there be more between us? And, she said, she didn't mind my little secret either. And would I want to explore more? She may have a skirt that would fit me.
It was a shock that I felt. She had already uncovered my deeper, darker desire. And she was proof herself that it could work. She would not laugh at me, she would help me. And I told her I hoped there could be more between us.
She wanted proof. Her hand was back in my pants, and she told me to imagine what it was if the two of us were together. As she rubbed my dick through my leather panties, she told me I would have to wear leather skirts for her, perhaps a dress even. I would have to wear a leather bra, and fill it up. I would walk in heels and wear a wig and makeup. And she would call me Jolene.
As the picture of the new me formed in my head, her fingers kept on rubbing my hard-on and I couldn't stop myself. The thought went even further than my deepest fantasy ever had, and without warning I came. Hard! My junk squirted into my leather panties, but thank God, nothing squeezed out.
She seemed extremely happy by now. She grabbed her purse and took something out. Something pink. She pushed it in my hand and told me to go to the bathroom and clean myself up. Then I had to put the pink thing on myself. If I came back, wearing it, she'd take me to her place and make all my dreams come true.
Thank God there was a free stall in the bathroom, as I awkwardly walked in, feeling my own junk starting to drip along my legs. I was just in time cleaning it, before it would stain my regular pants so that everybody could see. I wiped everything off, and dried the inside of my panties as best as possible. Then I took the plastic tube from my pocket.
It wasn't very big and the inside of the tube was soft thanks to a silicone lining. The disturbing part was that my own dick had shrunken so much that it could easily fit in the tube. I pushed it in, pulled it out, and there wasn't much to it. I just didn't understand the extra attachment that seemed like a broken ring.
As I messed around with it I realized it could go around my scrotum and as I pulled the broken pieces of the ring toward each other, they suddenly clicked together. And now, if I pulled the tube as far over my dick as I could, the extra tip that was attached to the ring clicked into the tube.
I tried to figure out how to undo it again but no matter what I tried, the pieces wouldn't come apart again. My guess was that there was a small hole somewhere in which you could push a little pin that would unlatch it again. I'm sure Millennia would know, and since she wanted me to wear it as proof, I pulled my panties over the contraption, and I was surprised that I had less of a bulge now than before.
When I finally got back to the bar, I apologized that it had taken so long for me to figure the tube thing out. But it was attached now and I couldn't get it unlatched again. Millennia told me indeed not to worry, she had the key to unlock it at her home. And that's where we would be going.
We walked hand in hand to her place, which was a wonderful feeling by itself. In her heels she was slightly taller than me and I liked the way they clicked on the pavement. At some point she let go of my hand and put her arm around my hip, and I followed suit, my hand now on her leather.
I couldn't believe it, since I had cum less than half an hour before, but I felt my hard-on coming up again. Which was quickly replaced by a stinging pain in my dick, and I cried out. She didn't have to ask what was going on, my expression with tears in my eyes was clear.
She did apologize for putting the “cage” on me, as she called the tube, but if anything was to happen between us, then we both had to wear it. For her that was the only way. But, she confessed, she had butterflies in her tummy about me, and she had to use all her willpower to not grow hard in her own cage.
And suddenly I understood. If she had a rock hard dick for me, how would I feel about that? I wasn't gay, right? I wouldn't be going to her place, for sure. She was having the same worry about me, and my cage put us at even footing. Well, not quite, because clearly I didn't have her willpower.
When I asked if she could teach me, she laughed. I would find out quickly enough, after a few more mishaps. And she pulled my hand back on her leather butt, as she led me to her apartment in the next block.
So, where I had initially hoped to get lucky with her, now I started wondering what kind of sex could two people have, who were both caged, or locked up, whatever.
But, I needed not to worry. The moment she closed the apartment door behind me, she pulled me into her, and she kissed me. And all sensible thoughts left my mind.
I have kissed a few girls in my life. Okay, just one. My second cousin as a matter of fact, as we both tried to figure out what the big deal was, and we couldn't explain it at the time. But now I suddenly knew.
Her agile tongue was deep in my mouth, the tip probing the smoothness of my teeth. Never did I taste something so special in my mouth, as finally my own tongue made it into hers. And when a soft moan escaped from her mouth into mine, I realized both my hands were on her leather, and both of hers around my neck, keeping me tightly locked in her embrace.
I had trouble breathing, but I didn't care. If I would die right there in her arms, I would be buried with the biggest smile on my face. But again, I had nothing to worry, as she gave us both a tiny bit of room to breathe, before she plunged her tongue back in.
The game of tongues was wonderful but she was better at it, simply because hers was longer than mine. She could tickle my throat with it, and after my initial gag reflex I started enjoying the pressure she put there. And as I tried to suck her tongue in deeper, I felt a shiver go through my system, and she pulled away laughing, saying I had my first throat orgasm.
It broke the ice and she asked if I was ready for sex. I confessed I had never had sex before, and that I had no clue what to expect. At which she asked me to trust her, to follow her lead, and enjoy the toys she would bring in the game. But first, she wanted us to get naked.
It wasn't that I was scared suddenly, but I really wanted my first time to be with her wearing her leather skirt. She smiled at that, completely understanding, then asked from me the same.
And as I stood completely naked in front of her, in only my pink cage, she found a skirt in her wardrobe and told me to step in. It was a black leather pencil skirt, something I had been dreaming about. It reached to my knees and it was so tight that my upper legs couldn't move. I could shuffle around a bit, thanks to a little split that allowed me to move my lower legs a bit. The only problem? The zipper wouldn't close.
I didn't mind too much, the way the skirt was not going anywhere. But she wanted it to be perfect, and she came back with a sort of corset. Sort of, I say, because the black faux leather would cover my breasts, had I had them.
As she tightened the laces a bit in the back, she shoved something in the cups that looked very much like real breasts. And as she quickly tightened the back more, I could feel the weight on my chest. These were not a pair of socks.
As it got tighter and tighter around my waist, she told me to take short breaths until I got used to it. And in doing so, she managed to lace it even tighter. When she was satisfied, the zipper of my skirt closed without issues, and when I looked in her full-size mirror, I knew she was right.
I had curves, the skirt over my hips, then a much narrower waist below my perky breasts, all covered in what seemed like a one-piece leather dress. She appeared next to me in the mirror, as she wrapped her arm around my waist, and she whispered in my ear if I wanted to finish my looks. I could only nod.
She put a wig on me, curly red-brown hair, and then I had to sit down in front of her make-up table, but facing her. She had to get rid of a few stray hairs on my chin, but then she started applying a slew of cremes, powders and paints. When she was finally done I was allowed to look in her mirror again, and she said that Jolene was born.
Where before I had seen my face on top of a leather covered curvy body, was now an attractive brunette, or was it red? My curls framed a pretty face that I would have easily fallen in love with, had it not been me. There was nothing shy about my looks, cute and confident crossed my mind.
And as I couldn't stop looking, she had me lift up my leg, as she put my foot into some black shoe, and then my other foot. It changed my posture completely, as I suddenly stood two inches higher, my breasts suddenly more pronounced as my legs stretched under the skirt. I was Jolene.
She made a series of pictures of me, then of us, standing in front of the mirror. She had pulled a tiny red top across her breasts, leaving her midriff bare, and I think that was the moment I fell in love.
In a pair of red sandals with a tiny heel we were now the same size, which made it perfect when she started kissing me. For a moment I saw in the mirror two women kissing each other, but before I could think that was probably wrong, my mind went once more to mush.
I had a throat orgasm again, before she had me lay down on the bed, with shoes and all, as we started making love. Or she, I should say, as I could only whimper from the sensations, as she kissed my bare neck, while her hands were all over my body. I could tell she kissed my breasts through the leather cups, and I wished they were real so I could feel it.
But I could feel it when her tongue traced between my breasts, as her hands disappeared under my skirt, that she had pushed up onto my hips, so that I could spread my legs. Then her kisses were all in my crotch area, until she started licking there with her long tongue.
My body had gone lax, overwhelmed by the pleasant sensations. I realized my caged member was in her mouth now, as she licked my scrotum, which was a sensation that started me to go hard. I felt the pressure building inside the cage, and my mind tried to stop it before the pain would come.
I am Jolene, I thought to myself, and my lover is sucking my clit. And as I kept repeating that, the pressure got a different meaning. My clit was swollen from her onslaught, and I started pushing my hips up so my clit would go full in her mouth. And when I felt a finger enter me behind that hotspot, it could only mean that she was now stimulating my pussy.
I moaned, and another finger was added. And I begged for more. Deeper. Harder. Fuck me!
For a moment the fingers disappeared, but before I could cry out, something else was pushed in. Something smooth, and much thicker. It hurt slightly, but my pussy started sucking it in, muscle by muscle accepting her gift. And deeper it went, much more than what her fingers had done, and I did cry out finally. More!
As it seemed to have reached its full length, it moved back and forth, while twisting and tickling. And my whole body moved with the sensation. A totally new feeling started developing and I knew a new sort of orgasm was coming. That's when the vibration started.
Any words that I try to describe that feeling will not do it right. I went from slowly approaching an orgasm well past the point of no return. I remember my body pushing itself up, into that feeling, when I exploded.
I heard someone scream as I was on fire. Every bit of my skin was burning, nothing was untouched. The sensation was heaven and hell at the same time, as it was simply too much. I wanted it to stop and relax in this feeling, but it pushed on. My whole body was vibrating now, in sync with that center of my world. And then every muscle in my body gave up.
I fell back down on the bed, as did my arms, my fingers, my toes, even my tongue. My cry stuck silently in my throat, as the vibration finally stopped, and I could draw some air into my lungs again. I could feel sweat streaming from my skin, literally everywhere, and the first muscle that started working again was a smile on my lips.
I was vaguely aware that the godly intruder was pulled from my pussy, the empty feeling a cold contrast with the heat still inside me. But it allowed my mind to finally come down from the enormous high it had been on.
The first word I said was “Wow!” and I heard Millennia laugh, saying something like “Unbelievable”. And when I opened my eyes, not remembering when I closed them, I saw her face, in total awe. And I knew I was really in love.
Baby, she said, you were amazing! I think I said thanks, as I started wondering when we could do this again. Then the guilt came.
My mother had instilled it in me, and I had promised her that I wouldn't forget. But then again, I never had sex since that promise, until now. It was simple really. Sex is a two-way experience. You give and take. Mom had said that sex was an unbelievable experience, and that has to be returned to your partner. And this woman had made me cum twice now, with some added throat flutters, and I had given nothing in return.
My turn, I told her, and she nodded, then crawled over me, lifting up her skirt, as both her legs were now alongside me. And then she lowered herself, her pink tube, which was much bigger than mine, I realized in the second I saw it before it pushed between my lips. And my mouth made love to what was left of her manhood.
It was weird, as the thick head of her dick stuck out of her tube, and as I licked and sucked it, I could taste the pre-cum leaking from it. The soft tip tickled my throat now, and I realized that giving back didn't mean that I couldn't take more.
My hand suddenly found a rubbery pole on the sheets and I knew that was what had been inside me, only a moment before. And in one move, without letting go of her manhood, I lined its soft round tip up with where her own hole had to be. And it slid in without too much resistance, her loud moan encouraging the speed.
Somehow I was fighting on two frontlines now. My mouth was attacking her manhood, my hand holding a missile ravaging her womanhood. And both attacks led to her surrender. It was like a balloon about to burst, while you keep pumping air in it. But when my missile bottomed out, I could feel the little switch at the end of it. And suddenly she started vibrating.
I could feel the sensation in my throat, in my face, in her legs that clamped around my face, and in her buttocks between which I had shoved my missile. And then the bubble burst.
I heard her cry, as my mouth filled up with slimy goo, much thicker than the pre-cum. Much more went straight down my throat as I felt that added bonus of another orgasm, from her dick rubbing my insides. At the same time her rear spasmed as her double orgasm rocked her body, while I held on to both of her hoods.
I could sense her muscles giving in, and as she collapsed on top of me, I just managed to flip the switch back, and I could feel her relief relax her body. I barely could draw some air in through my nose, as her dick was still buried inside me, my mouth full of her gunk, that tasted unexpectedly pleasant. I had to wait for her own high to subside, as I was feeling proud for giving back, and being rewarded even more in return.
It felt like hours, but it was probably just minutes or seconds even, but I could feel how the tip of her dick slid back into its tube, giving me a chance to slowly swallow her nectar. My hand managed to pull the vibrator from her rear, and after an initial resistance it almost popped out, as I felt her breath escape somewhere above me.
And finally she started to move, her manhood pulling from my mouth, her legs unclamping my face, and as she crawled down again she pulled her skirt back, and before she laid next to me, she pulled my skirt down as well. Then she told me she loved me, and as her arms wrapped around me we both fell asleep.
The night was one of many firsts. The sex, of course, was a first for me. And so were blow jobs, throat orgasms, anal orgasms, dildo's and unbelievable vibrations. Add to that being dressed in a skirt, a corset, with fake breasts, on heels, with a wig and makeup. Which made my sleep pattern quite different, as I normally spread out on my belly, my legs in all directions. Well, not so much of that in a pencil skirt that kept my legs tight together, or with breasts that kept me on my back, maybe slightly on my side. And then there was Millennia, whose body fitted tightly against mine, her hand protectively around me, the first woman I ever slept with.
I think I was in love, another first, as was she, according to her last words before we passed out. But can that stuff even be true? Or was it in the heat of the moment? I've always thought that you meet someone, you date, maybe go on a trip together, so you get to know each other. And in that process love will slowly develop, laying a solid foundation for a life together. We knew each other for less than twelve hours.
Those were my thoughts as I woke up, with my hands touching my leather skin, brushing my breasts, and feeling her touch on me as well. I was the girl in this bed, another first. Yet I liked it. I liked being her girl. I liked how I came as a girl. I liked how I gave her a double orgasm. I liked how I wasn't shy around her, how I looked. And I liked the thought that perhaps we were made for each other.
I could feel her stir and I sort of turned so I could face her. She was beautiful, her eyelids fluttering now, as she was about to wake up. I liked how she was also still dressed in her red leather skirt, and what I could only call her breast cover, as there just wasn't enough leather to cover anything else.
I touched her nipple through the soft material and it went instantly hard. I dragged myself a bit to the bottom of the bed, until my lips lined up with her breasts. And as I opened my mouth around her breast, my tongue teasing the hard nipple, a moan escaped from her. I freed the breast now, and started sucking, which resulted in a gasp. And as I looked at her face again, her eyes were open now.
Jolene, she whispered, there's something I want to try. And she explained how she had been wearing her cage for more than a year. The goal was for her manhood to shrink so that she eventually could wear the cage that so easily fit onto me. But it never happened. Sure, it prevented hard-ons and her full length to come out, as a matter of fact, last night was the first time that she'd seen her cock-head poke out.
But now she wondered if it was ever meant to be. We both took our skirts off, and the difference was suddenly clear. Her tube was probably four times as long as mine, that's why she could have reached the back of my throat. Other than that it was very much the same, although mine would even prevent the head from coming out.
She gave me a tiny key and she told me it was up to me, but seeing how much I had liked the dildo up my ass, my pussy, she wondered if maybe I wanted to feel the real thing. For as long as we were together, she promised, I would have control over freeing her now and then, as she would have the key for my cage.
I saw the symbolism of the key owner thing. And looking at her manhood, my control over her would be much greater than what she had over me. Even in my greatest euphoria last night I had not gone hard at all, as Jolene only had a clit there. Yet I had come harder than ever in my life from masturbating.
I saw the need in her eyes, and I knew I would have been appalled only one day ago, but last night changed my total view of life, of genders. And as she explained where the keyhole would be, I realized it was more than just a pin. I had to push it in and twist it, and suddenly the pieces came apart, as the key came out again. I carefully pulled the tube away from her dick, and removed the ring from her scrotum. And already she was growing. I don't know why, but it looked beautiful on her, totally hairless, and I gave it a quick kiss.
She then squirted some gel on the tip and she spread it all out across her member, which was by now thicker than the rubber dildo we used last night. And she asked if I was ready. Ready for what? For that!
And she pushed me back on the bed, and as she positioned herself between my legs, I automatically spread them wider and I realized that as Jolene I was sending out an invitation. And Millennia took it as such.
Oh, she was gentle, thank God. Her cock head was much bigger than last night's toy. But, thanks to the slippery gel it pushed slowly in my waiting pussy. She went in and out, allowing my muscles to get used to the sensation, but each time she went a bit deeper. And once more, my body reacted on its own.
I started moving with her, anticipating when she pulled back, then moving into her as she pushed back in, welcoming the intruder much deeper inside me. And after a minute or so her balls slapped against my own flesh.
As it got more urgent for the both of us, I could still feel her even deeper inside me, as her length was still growing. And I guessed she was probably at the entrance of my womb by now. That thought made me pull her body down, and as our breasts squeezed together, my mouth found hers.
And as she ravaged both my mouth and my pussy, only one thought remained. I wanted her. Needed her! I was Jolene, her Jolene, and I was her fuck toy.
My throat orgasm came first, and as I used all my strength to pull her deeper into me, with my hands on her buttocks, my body started shaking. It was like an orgasm in slow-motion. We both cried out as my vibrating muscles took her over the edge as well, and then as I heard her grunts, I could feel her spray my insides.
If I had thought last night that it couldn't get any better, I was proven wrong right now. The power of her spray took my high even higher, and I screamed in ecstasy now. And when she finally had emptied her balls, we both came slowly down again, which was the most incredible relief I ever experienced.
I was kissing her now, as she'd gone numb. I could literally feel her shrink inside me, and I could no longer hold on to her. Eventually she popped out of me, both tongue and dick, as she rolled to the side.
Nothing was said, as my mind reeled. I was fucked! How could I ever be a man again? Why would I want that even, as I just had the best sex of my life?
I wasn't the only one confused. That became more evident as I heard her crying. Soft sobs at first, but she stopped holding back, and I put my arm around her, trying to comfort her. Eventually she started talking, explaining.
Her mind had been female most of her life, and it was easy, even felt right, to make her body follow suit. And it did, she was more female than most naturally born women. Except for her manhood. Despite hormone treatments and sessions with a psychiatrist, even some sort of brainwashing, her dick would not shrink. The idea of chastity seemed to work, but she never managed to switch to a smaller cage. And now, the first time unlocked after more than a year, it seemed like her manhood came back, even stronger than before.
I tried to help her, but I was confused myself. I told her she was a beautiful woman, no matter what, or I would not have fallen in love with her. And maybe her manhood was always meant to show me the way, my way, my future. Somehow she made me her woman. My own dick wasn't even involved in any of the sex we had. But my body needed hers. Clearly.
Maybe it was fate that we met. Maybe it was compatibility. But the only reason I had become Jolene, her Jolene, overnight, the only thing I could think of, was because we were meant to be together. I became what she needed, and she is everything I needed. And that includes her manhood. And I did not need hers to be caged.
Her crying had stopped, but she thought it was unfair. To me. She had put me in chastity, so that we were on even ground. So, either she should be locked again, or I should be freed. I disagreed.
The way I saw it, we were two pieces of a puzzle. A confusing puzzle in my case, as I could never understand why I was so shy, why girls didn't want me, why I had a need to wear girly underwear. But now, finding her, that other piece of the puzzle, with its own funny shape in a way, her own questions that were never answered. Our two pieces fit perfectly together, forming a perfect picture. And when something is perfect, you don't mess with it.
Like I said before. If it sounds too good to be true, it probably is. But, if it feels so good that you never want anything else again, then accept what you are, who you are, and who makes you feel that good. With Millenia on my side, I would be Jolene forever. Soon with real breasts and a real pussy, I would always be her girl. The puzzle solved!