Jeannie and the Bottle Pt. 01

I tip the beer glass over a little and let it revolve under my fingertips, the dregs of the serving sloshing around inside. I can see the rich red-brown hue of the bar top through the clear glass, distorted only when seen through the IPA. It shifts as the Christmas lights behind the bar move through their blinking sequence even now in middle of July.

It is another Friday night for me, sadly typical. Romero's is a locals bar and I am regular enough to know the Harold the owner, the bartenders (Mike, Annabelle, and Lydia), the wait staff, and the other regulars. I never drink that much but mostly like being... somewhere. I'm part of many conversations but like to feel them flow around me.

Drifting has always been my way. Due to the unexpected kindness of a now-passed Great Uncle, I'd been given a small trust fund that was thoughtfully designed to ensure that I could always have a place to live, food on the table, the basics of a comfortable if uninspiring life. Perhaps the security of that made it hard for me to become very passionate about working. I mean I almost always had a job but if I lost that job, I wasn't that upset. I definitely didn't have a career you could really name. My resume, if I made one, would look like an aspiring actor who never went to an audition.

Right now I work as a tech support analyst for a software company. I know I'm smart as the job is easy for me and a struggle for others. But I have no interest in their offers to become a manager or senior technician.

As I mentioned, drifting.

It isn't really any different in my love life. I'm not an ugly guy. I had one girl call me 'almost pretty', a comment that seared into my brain though I felt a little uncomfortable about it at the time. I'm 5'8" and trim... even slender?, fit but not really muscled.

Occasionally I'll meet a girl, go out a few times, may be sleep together a few times. But it always fades away. I know I'm not their typical boyfriend but I suspect my lack of ambition is a buzz kill for them. I am fascinated by them in many ways but not enough in the way they are looking for. I really feel that women are the most beautiful, sexual, and wonderful creations on the planet. I drink in everything feminine about them. Sometimes I forget to act like the guy they want to be with. I love having sex with them but I'm not some predator looking at them like prey.

My fantasies don't really help me in the dating arena. I have three sisters all close to my age so growing up I seemed awash in feminine things, their clothes, their delicates. My fascination with the feminine started early and led me to experiment with some things, especially when between girlfriends. I enjoy a little cross-dressing, a little lingerie fetish in the comfort of my own home. It allows me to embrace this delicious femininity without getting strange looks from my girlfriend or that inevitable feeling that I'm not focused on her when she doesn't understand why I ask to wear her underwear.

It's been weeks since Sara and I stopped going out but I haven't started digging out my 'girly box' yet. Drifting and now I've washed up at Romero's again.

It's only her laugh that breaks me out of my deep but pointless self-reflection. Glancing down the bar several stools, I see a girl... a woman having a great time in the middle of a huddle of men and a couple women. They are all laughing with her but she's more of the object of their attention than a friend. I'd certainly never seen her in Romero's before.

The bar itself is fairly well-lit so I can see her clearly. A shock of red hair cut short in back and spikey on top... almost pixie-ish facial features that almost define the word cute... a low-cut top making no secret of her large breasts especially noticeable for her smallish frame. As a lingerie afficiando, I easily notice the black lace edging and hint of red satin of her bra and inside I approve. And I'm a little envious.

She's drinking pretty steadily and her laughs and talking seem more like a performance than anything else. As pretty as she is, her cluster of an 'audience' begins to drift away from her, back to their own friends. She isn't responding to the advances of the die-hard lusters so they eventually give up as well.

She is someone who clearly expects to be the life of the party. I'm sorry for her. Lydia, the bartender, dutifully tops off the four shot glasses in front of this woman and I feel compelled to close the distance between us.

"Are you sure you want to drink all that?" I ask. My tone is not playful, not lewd, not suggestive. I feel a pool of caring inside me that I'm not used to and I guess it comes from there.

She looks at me, up and down, and then in my eyes. I see several cheap retorts, flirty come-ons, and other comments jostle inside her and nothing comes out. She touches one of the shot glasses and I put my hand on her wrist, gently, just the slightest touch. A question, not a command.

She takes her fingers away from the glass.

"Who are you?"

"Jeremy. Jeremy Supkin," I say easily, a little eager for her to know who I am. There is a charisma to her that is almost enchanting, far beyond her physical good looks.

"Why do you care, Jeremy Jeremy Supkin?" she asks quietly, emotionally raw but hiding behind the well-worn joke response.

"Why don't you?"

I'm fascinated by what I'm saying. If I'd had to script this before I got to Romero's I would never say these things, but they seem like the right things. From someone for whom caring has always been difficult, it now seems easy. I could get drunk on it... for her.

We sit on the stools, looking at each other for a good while. Life in the bar goes on around us. Lydia eventually sells the undrunk shots half-price to some other patrons and tucks away some of the cash in her bra (her DD "I'm not going to be a bartender and stripper forever" fund).

I'm not sure how I find myself walking with "Red" in the nearby park but I'm holding her hand and telling her everything about myself. I'm telling her things I've never told my family or my girlfriends. She uses just a few questions but prompts me enough to guide my flow of information. It feels like a drugged state in some way but I'm happy to tell her anything.

"How does it feel when you dress up girly?" she asks.

I hesitate. Why have I told this girl whose name I don't even know about that? She gives my hand a squeeze and I realize that I have nothing to worry about.

"Well, it's sexy as all get out. I always cum hard and often multiple times. I love how it makes me feel about myself, about who I am..."

"About who you could be?"

Again, I pause. As much as I love my girly games, I'd never really thought seriously about a sex change or anything. I didn't feel like a girl trapped in a boy's body or anything. I just felt like me... only sexy and...desireable... in the right place...free...

"and wonderful..." I trail off. It was getting hard to keep what I was thinking from being what I was saying.

She kisses me. With a good kiss, you lose all sense of the world around you. Only you and she exist in that moment and you want it to stretch on forever. She is that good a kisser.

I realize we're now in a late night coffee shop, dimly lit, in a booth where the waitress can pretty much ignore us. I'm drunk on her lips, the taste of her skin, the feel of her breath on me, my hands on her body. It doesn't matter that other people could see us, all that matters is her.

I'm fascinated by her breasts. She has no hesitation letting me touch and feel whatever I like so I cup them, caress them, enjoy their weight and softness through her clothes.

She pulls off her top which only momentarily shocks me in the coffee shop. She watches as I touch her breasts further, enjoying the taut satin cups of her bra and that entrancing cleavage it makes.

"Do you ever think about what it would be like to have breasts?" she asks.

I mean I've fantasized about it, sure. I like wearing bras and bustiers (always satin) and filling them so they look very feminine on me. I've toyed with the idea of buying false ones.

"...I'd love to know what it would be like to have them." Wait, was I thinking or talking? Why do I think it wouldn't matter with her, she would hear me.

"Jeremy, my name is Jeannie, and I have a serious offer for you."

Reluctantly, I pull my eyes and hands from her breasts, sit back a little and meet her gaze.

"I'm granting you three wishes. They will only work when you say 'I, Jeremy, truly wish...' There are only three, never more."

I am pretty stunned by this and in any normal situation, it would be a joke. Tonight, it seems a natural progression of all the strangeness.

"Why?"

"Jeremy, you are a rare human in this world. You love women but looked past my charms and did something caring for me. You got me out of that bar and out of that bottle. That hasn't happened in a long time." Her eyes are so penetrating but in a way that makes me feel accepted.

"I guess you could say I'm an expert at seeing the truth inside people and trying to help them."

I should have a thousand questions for her but I'm overwhelmed by this sense of trust and peace with her. Still, three wishes?

She reaches behind her back, unhooks her bra and reveals her naked breasts to me. She caresses and holds them, her nipples swelling and rising. I can't take my eyes away. She caresses her body, breathing deeply, her breasts rising and falling.

"I Jeremy truly wish I could have breasts like yours..." I blurt out. She kisses me and I guess I fall asleep.

In my book, the morning sun is pretty cruel. I never drink enough to have a hang-over but I'm not a morning person either. Unless I have to get up for work, I tend to resist rising as early as some other folks.

So I lay in bed, feeling the sheets and the light blanket on me, the whirr of the oscillating fan I run during the night. Something feels... different. I remember everything about last night except how I got home or when Jeannie left. Well, maybe I don't really remember that much...

Stretching, my eyes fly open. The way the sheet and blanket move on me feel so different! My body, a weight of my chest...

I throw the covers off and look down at myself. I have beautiful large breasts, perky but flattened just a little from gravity as I'm laying on my back. With shaking fingers, I reach up and touch them. They are definitely mine and not elaborate fakes as I feel every fingertip moving on my skin and they feel warm and real to my hands. I've never seen breasts from this angle really though obviously its the angle all women see their own breasts. I chuckle once at this realization but maybe it is mostly from shock.

I sit up, eyes glued to myself. I feel their weight on my chest but as a part of me not something separate. I feel them, hold their weight. Definitely not breasts made from saline implants. The reality of them being part of my body becomes more real with every moment. At some level I feel the enjoyment of having what I'd dreamed of so often.

Touching them, exploring them feels so good. My nipples are large and I feel them start to tighten, to extend and stroking them is erotically electric. My cock is rock hard in seconds in my boxers. I can't stop myself as I practically grope myself, enjoying touching breasts and the magic of being touched. Soon, I'm moaning, laying back, pulling on my nipples, feeling increasing pleasure and intensity in my groin.

Without warning, I feel my balls tighten and then my groin pumps, painting my boxers with cum as an orgasm rushes to fill my body, every bit inside and out. I'm crying out in pleasure which I never do unless I'm playing my girly games. I've never orgasmed like this and the intensity of the dopamine rush is stunning.

When I recover, I lie there holding my breasts, feeling my cum oozing around my cock and in the now-soaked fabric of my satin boxers.

"Oh my god..." I whisper to the room.

Eventually I get up out of bed. It takes a second to rebalance myself with this wonderful weight in front of me. Looking at myself in the mirror I see my slender but still male body just blessed with jaw-dropping breasts. I nearly start caressing myself to cum again but I assume there will be time enough for that later?

I rush into my closet to pull out my large though carefully hidden girly box. I dump it out on my bed... a large pile of panties, bras, bustiers, thigh high stockings, a couple pairs of high heels, some fetish dresses, and more.

When I'd been buying this stuff, I'd sort of not kept to a particular cup size but as I paw through the delicious satiny stash, I find what I think will be the perfect bra. Red satin, black lace edging, D-cup. It looks exactly like Jeannie's bra did. That can't be a coincidence but I dismiss the thought.

I step over to the full-length mirror and eagerly put the bra on. I adjust the bra so my breasts fill it just right. I'm quite practiced at this but the chance to put it on over my actual breasts and adjust it is... joyful to me. The bra brings them together a little so I have cleavage most women would kill for.

I turn around this way and that, delighting in the look of the band around my back, the shoulder straps, how everything looks how it should with a bra instead of the not-quite-right way it always looked on me before. My brain can't wrap around the impossibility of this situation so it doesn't try to find an explanation.

Wanting to see more, I start some serious dress up: matching red satin panties with black lace edging though my hard cock makes it difficult to get them to sit properly... black sheer thigh high stockings and a black satin garter belt... 4" stiletto heels with ankle straps... a pretty dress with a skirt short enough to flirt with showing my stocking tops...

"If I had a wig, some makeup, I could totally pass" I murmur to myself as I pose and prance in front of the mirror. I run my fingers through my hair and think of Jeannie. I grab some hair gel from my bathroom and spike up my hair until it looks like hers... gender fluid enough to look girly.

By now nothing will stop me. There is no plan just what I know I have to do. I find the small, soft-sided silver case in the girly box pile and go into the bathroom. I don't have an extensive makeup collection, bits and pieces bought at different times or 'borrowed' from girlfriends. After practicing this many times for my own amusement, I find my fingers are adept and soon I look quite feminine.

Returning to the full length mirror, I can't keep my mouth from hanging open. I don't really have the hips or ass that would make my figure a total knockout but the heels shape my legs, the dress clings just right to my slender frame and large breasts. My cleavage is visible though not so much that I look like a slut. It just totally... works.

My heart is racing. What I'd fantasized about for most of my life was partially real. Am I really going to do this? My stomach churns with arousing anxiety. I've never dressed up like this and gone out in public. I've only ever showed one person, a girlfriend who soon after was not my girlfriend any longer. I felt a sense of fear but that only enhanced the rush of it. My cock was swollen so hard and throbbing that it was making an unsightly bulge in my dress.

I paw through the pile on the bed until my fingers brush something hard. I pick it up and look at it, not recognizing it as something I remember buying: pink plastic lockable chastity cage for a cock. Part of me wants to stop and start asking the universe a lot of important questions but the rest of me tells that part to shut up lest I spoil whatever is happening here.

Lifting my dress and lowering my panties, I squeeze the base of my shaft hard and hold it. I wait as my cock slowly loses its engorgement and I look at how to put the cage on. When I am soft enough, I start to put it on, stopping only to stop the inevitable swelling again. It's a little tricky but eventually I'm standing there with my seven inch cock contained in a two inch pink cock cage. I put the key carefully on my dresser.

The feeling is... frustrating but not too painful. The pink looks good on me and when I pull up my panties, they fit much better. Still a slight bulge in front but nothing that would mar the lines of my dress which I pull back down.

I am very sexually charged and aroused but in a way being caged takes the immediate need to masturbate and cum away a little. I feel like I can stay in this delicious, aroused state as long as I like this way.

Checking myself again in the mirror, nothing gives me away. My adam's apple has always been slight so you don't really notice it. I can totally pass and that's what I'm going to do!

Driving in my Honda down into town, I'm struggling to decide where I want to go. It's Saturday and I want to be seen but I'm also terrified. I want people to desire me, to struggle to not look at my breasts, at me. I want to feel beautiful.

I end up walking around our town's large outdoor mall. For awhile I blush as men stare and gawk at me, enjoying their desire and attention like caresses on my body. It's a thrill to see that while many women glance at me with jealousy or indifference, there are more than I would have predicted who have as much desire as the men in their eyes. (To be fair, there are men walking around that could care less about me as well).

Walking in the dress is amazing, feeling the air on my legs and my panties. I love how the material hugs and pulls on my body, how my breasts push against it. I make an excuse to pick up something from the ground, squatting in a ladylike way but still my dress rides up to give a view of my thigh high stocking tops and garters. I'm putting on a show and I'm having the time of my life. The cock cage is... uncomfortable as my cock really wants to get fully erect but somehow that's part of the delicious experience.

Victoria's Secret looms ahead. I feel none of the apprehension of past visits but feel rather very much at home. I browse through the racks of bras and realize that I don't know my size really. Daring something I'd never done before, I ask the prettiest girl there for help. Trust me, my cock would love to get out of its cage with her but I'm riding this dreamy, heavy arousal sensation the whole time.

She is friendly and I get no sense that she sees me as anything but a woman. Her name tag says "Crystal".

"Hi Crystal, will you measure me? I'm not sure I'm wearing the right size?"

"Sure thing, most women are wearing the wrong size though you might be good with what you have on now. Will you follow me?"

She leads me behind their check-out desk to a hallway and to the fitting rooms. Without being asked, I take off my dress leaving me in my lingerie and heels.

Crystal does pause for a just a second and I think she sees the slight bulge of my caged cock in my panties. I mean it would be hard to miss if you looked there. Happily she recovers and she is very present now. I'm not sure what she is thinkng.

"Can you take off your bra?" she asks, genuinely unsure. After unhooking the bra and taking it off, I raise my arms as she puts the measuring tape around my full bust and under it.

"40... really more of a large D or even DD..." she muses as she adjusts the tape on my skin. Being touched by her even in this professional way has my nipples rapidly erect and my cock throbbing in its cage. My nipples do not go unnoticed. It is not cold in the fitting rooms so I have no excuse.

"Would you... like some help looking?" she asks, stumbling over her words a little as she blushes. Could I have lucked out and found a beautiful Victoria's Secret sales girl who is also a lesbian? Or am I exuding some sort of new confidence and charm?

"Yes, please," I say, more to the thought of making out with her in the fitting room but also to help shopping. I put my dress on without my bra and follow her around the store. Looking at myself in one of the mirrors I see that my breasts don't need lingerie to look perky and perfect.