tagTranssexuals & CrossdressersFeminine Fantasy Come True

Feminine Fantasy Come True

bygirlboybootsie©

One Saturday morning I wake up and decide to go shopping for some really sexy and feminine girls clothes. I'm what I guess you could call, a "closet cross dresser." Although I have always been too shy to try and pass as a girl in public, I have been dressing up as one in secret ever since my sister first dressed me up as a "joke," when I was a boy. I realize that not all cross dressers are bi, or homosexual, but in my case, somehow I associate the incredibly sexy and feminine feelings that always come over me when I'm dressed as a girl, with the desire to be with a hunky guy, and to please him by playing the role of a sexy girl. Strangely, it is usually only when I'm dressed up that I have these cravings for men, and I don't think any of my friends, or my girlfriend, would guess that I have this secret other life.

On this particular morning, after first taking a shower and drying and combing my long blond hair, I lubricate and then slip a large butt plug up my ass. It's always a little painful at first for me, probably because I've never fulfilled my dream of being fucked by a man, but I absolutely love the sensation of walking around with my ass stretched by this huge plug, imagining that it's really a big cock. I then slip on a pair of sexy tight pink silk bikini panties. I smooth them over my tight hard buns and the base of the butt plug and my throbbing cock (which always gets hard when I slip on a pair of sexy panties). I then choose a lovely pink satin garter belt with white lace trim and a matching bra. After slipping them on, I roll a pair of sheer white back seamed stockings over my long and muscular legs and attach them to the garters. I admire myself in the mirror, and I feel so turned on and sexy that I almost give in to the temptation to go all the way, apply makeup, and insert my "boobs" and slip into a sexy leather minidress and boots. But today I want to go out shopping, so I content myself with slipping these things into a bag, just in case I decide to dress up fully afterwards.

I cover my feminine lingerie clad body with a pair of sexy black tight leather pants and a nice white silk shirt. I wear my black loafers. Although wearing a skirt makes me feel sexier, the tight leather pants hugging my panty clad buns and the feel (and sound) of them sliding over my stocking clad legs is quite a turn on. I wear a snug black leather jacket over my shirt, because without it, you can see the outlines of my bra.

I always love going to the mall and shopping for sexy girl's clothes. Walking around and observing the sexy girls and what they're wearing in the mall is also a turn on. I love to imagine myself as one of them, checking out and flirting with the young hunky guys and imagining them taking me home to their beds.

After arriving at the mall, I decide to go first to my favorite leather store. I recently saw an ad for their new Spring fashions and they looked really sexy. As I enter the store, a gorgeous young blond hunk welcomes me. He must be new to the store, because otherwise I certainly would have remembered him! He's wearing a tight white t-shirt that hugs his sexy broad shoulders and chest, and a pair of tight black leather pants like mine, which hug his tight buns and even reveal a bulge in the front. With a captivating smile, he asks if he can help me, but as usual I'm too nervous to admit I'm shopping for myself, so I tell him I'm just looking.

Walking over to the women's section, I begin admiring and checking the sizes of some sexy leather miniskirts, when I notice a rack of ultra sexy pink leather minidresses. They are so sexy! Picking one in my size up to admire, I somehow forget that I'm not alone in the store as I hold it up against me and run my hands along the smooth sexy leather. My cock has become rock hard within the confines of my panties and the tight leather of my pants.

Suddenly a voice interrupts me. "Would you like to try it on?", the hunky salesman asks with a dazzling smile. I can feel myself flushing deep red, but before I can stammer some type of excuse, this hunky dream man says, "let's take that jacket off so I can measure you before you go to the trouble of trying it on."

I continue to be too flustered to speak as he reaches out to help me out of the jacket and comes around behind me and helps me to raise my arms as he spreads the tape measure across my broad chest. All of a sudden I realize with horror that as he runs the tape measure around my chest, he can not only see the outline of my sexy pink bra through the sheer white silk of my shirt, but he can also feel it! I start to stammer something to cover up my embarrassment, but he cuts me off by asking me to "please stand still" and suddenly an electric thrill runs through me as my hard leather clad buns brush up (either by accident or design) against the leather of his pants as he takes my measure!

Although I am almost trembling with nervousness and I can feel that my face is still flushed, the confident and somewhat domineering manner with which this hunky salesman is handling me is exciting and my cock is rock hard within the tight confines of my panties and tight leather pants. After he finishes measuring me, I somewhat awkwardly take my jacket and hold it in front of me to hide the clear outline of my hard cock in the front of my pants.

After jotting down my measurements, this hunk of a salesman asks me if my cup size is a "D," and when I stammer out that it is, he tells me that I have chosen the right dress, but that I should try it on to be sure it is a good fit. Still blushing furiously, I am just able to stammer my thanks as I go into the dressing room.

My heart is pounding as I close the door, but my cock remains rock hard with excitement and I feel so incredibly horny at the thought that this hunk knows that I am slipping into this ultra sexy dress! Is it possible that he is gay, or bi and is attracted to me? The thought is too exciting to imagine as I slip out of my tight leather pants and my shirt. My panties are wet from pre-cum from my throbbing cock as I stand there dressed only in my sexy panties, bra, garter belt and sheer stockings. Since I do have my bag with me, I decide to quickly slip in my silicone "boobs" which fill out my sexy silk bra and make me feel even more feminine!

Almost panting with excitement, I then step into the cool sexy confines of the leather minidress and slide it up my lingerie-clad body and over my now jutting boobs. Then, slipping my arms through the short sleeves, I reach behind me to try to find the zipper, but find I am unable to reach it. As I am fumbling to try to reach the zipper, I suddenly hear my hunky salesman say through the door, "you're going to need help with that zipper," and to my complete shock he opens the door!

I stand frozen there as my face again flushes deep red. He wears a knowing smile as his eyes take in the site of my boobs jutting against the tight leather of the sexy dress and slide down to the clear outline of my throbbing cock, which is pressing against the tight leather of the dress like a tent, and thereby raising the hem of the front of the dress to reveal the garter tabs attached to my sexy sheer stockings! "Well, it looks as if you're going to be able to fill out all the curves of this dress" he says softly with a smile. "Let me zip you up!"

I turn away from him as he approaches and my blushing face is hidden for a welcome moment of relief. He approaches from behind and as he slowly zips up my dress, I feel the pressure of his hard muscular leather clad...what is it?... pressing against my own tightly leather clad buns! In response I reflexively squirm my buns and press back against him for just a moment, but he doesn't pull away, and I imagine that it is the bulge of a hard cock that I feel! He seems to take an extra long time slowly zipping up the dress.

"Let's see how it fits you," he says, turning me around, his strong hands on my shoulders. He then steps back to look at me. My face is blushing furiously as I stand before him. The ultra sexy dress fits me as if molded to my body. My jutting boobs with their hard press tightly against the smooth leather. The problem is, my cock is if possible, even harder than before, and this hunky salesman's gaze seems fixed on it jutting forth and clearly outlined against the tight front of my dress!

I stammer with nervousness, as I explain to him that I am going to a Halloween costume party and that's why I'm dressed as I am.

He nods as if he believes me, but I can tell from the sly smile on his face that he doesn't. I find myself squirming again under his gaze, which seems to keep returning to my throbbing cock, which continues to jut against the front of this ultra sexy leather dress.

"Well, you will probably be the sexiest girl at the party if you wear that dress. Now all you need is a matching pair of pink thigh high boots. If you go to the Booterie, they have some that would match that outfit perfectly."

I thank him and tell him I'll take his suggestion. He then offers to help me unzip the dress again and I turn around again, facing the mirror, hiding my blushing face with relief. But I panic again as I wonder what he is going to think of me when he sees what I am wearing under my dress! I see him step up behind me, and a shiver runs through me at his closeness. For a moment it sounds as if he is adjusting clothing, but he hasn't touched mine. Suddenly, his strong hands grip my leather-clad hips, and he smoothly slides my dress upwards, revealing my shiny tight panty covered buns! I reach out and lean against the mirror for support, but am otherwise paralyzed with shock. A second later, I squirm in excitement as I feel him pressing against my buns from behind, and then I let out a load moan of pleasure, "Oooohhhhh!," as I realize that it is an enormous bare cock which is sliding between the panty covered cleft of my buns and between my thighs! I am overwhelmed by the sensation, that all I can do at first is arch backwards against him and squirm, gripping his throbbing warm cock between my bare thighs as I continually gasp and moan in excitement! What a turn on! In all my fantasies of being with a man, I never could have imagined having a sexy hunk like this slide his bared cock unannounced between my legs!

"I guess these sounds you're making mean you like it," this stranger, whose cock I now have gripped between my thighs whispers into my ear, before taking my ear lobe into his warm mouth, and then swirling his tongue into my sensitive ear, causing me goose bumps and shivers of pleasure.

"Aaaaahhhhh, yes, I love it," I gasp. Looking down, I see that the huge head of his cock is now jutting forth from between my own legs. Reaching down, I grip my hand tightly around it, and begin fondling the shiny wet cockhead, which is oozing pre-cum. It's so huge, and hard! I love the feel of it in my hand.

We're both moaning in pleasure now, when all of a sudden, he pulls back away from me, his cock slides from my hand and slips slowly and wetly from between my thighs, and he removes his hot tongue from my ear.

I'm terribly dazed with lust, as he grips me by the shoulders and steps back facing me. His cock, which must be all of 9" is jutting forth and he strokes it slowly as he stares at me, his eyes moving up and down from my flushed face, along my body to the big bulge in the front of my dress He has a smile on his handsome face. "Dressing up like a sexy girl obviously turns you on. What other ways do you like acting like a girl?," he asks me.

I am so turned on and horny, I barely feel able to respond. I just want to get back into his arms, and this time I want his sweet tongue in my mouth, and then that beautiful cock... I'm saved though from having to answer, as someone suddenly knocks on the door, and a voice calls in, "John, I need your help at the register. Are you almost done?"

"John" as I now know his name to be, responds that he is just finishing my fitting, and that he'll be out in a moment. He steps forward and again gripping me at the waist, this time from the front, he leans forward and presses his beautiful full lips against mine, giving me just a taste of his warm tongue, before pulling his face back, and whispering, "I'm sorry. I have to go. I'll be off work at 6pm. Will you meet me, and will you come dressed like this?"

I tell him that I will. He introduces himself as John, and he asks me what name I'd like him to call me. It's funny, the way that he phrases it. I respond that he can call me "Jennifer". I'm so incredibly aroused, knowing that this beautiful hunk wants me. I don't know how I'll be able to wait until this evening. I lust for more of this gorgeous man, but he is already slipping his cock into what looks like a black leather thong, and zipping up his pants. He then quickly steps behind me, unzips my dress and helps me to step from it. I stand before him now just in my shiny pink silk panties, bra, garter belt and stockings. The front of my panties are wet with pre-cum and my cock is still straining against them. John tells me that he would like nothing more than to stay with me, but he has to go. He tells me that he'll ring me up at the register, and that he can't wait for tonight, but then slips from the dressing room.

To be continued...

Report Story

bygirlboybootsie© 11 comments/ 154510 views/ 13 favorites

Share the love

Similar stories

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartrandomalias, stehlen1 and 11 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by randomalias01/25/14

MORE!

Please continue this story! This is such an awesome fantasy! :D

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 11 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel