First Experience With A Man Ch. 2

Story Info
Jake prepares me for visit to BDSM club.
2.1k words
4.44
111.6k
13

Part 2 of the 2 part series

Updated 10/06/2022
Created 06/23/2002
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Leading me into his bedroom, I find the sexy pink corset, panties and stockings that he bought the other day at Frederick's all laid out, on his bed. There is also a pair of silicone "boobs." "I didn't even have time to give it to Jessica, so you can have it. I'll leave you alone while you change. You will need to slip the boobs into the cups of the corset. Do you know how to attach garter's?"

Flustered, I assure him that I do, and he then leaves me alone. Looking up, I note that there is a full-length wall mirror facing me, and mirror's on the ceiling as well (!). I look at myself in the mirror across the room, and it is the strangest experience, because from the neck up, I now have a pretty girl's face. This is the moment of truth, but I have come this far, so I quickly strip off my clothes, and pick up the frilly pink corset. I decide to turn away from the mirror while I dress, lest I lose my nerve. As I step into the sexy corset and pull it up, slipping my arms through the straps, I find that Jake is correct. It does fit me perfectly and tightly. I then slide the matching pink silk panties up and smooth them over my buns, and my cock. At this point, to my surprise, my cock begins to respond to the smooth silky feel of the panties and it becomes rock hard and juts against the tight front of my panties in seconds. I am amazed at the erotic feel of the panties, hugging my hard cock and buns, and the tight feel of the smooth corset, but figure it must be the thought of Jake, waiting for me outside the room, which is making me react this way.

I then pick up the stockings, which are sheer and white with French style back seams. I slip the first one over my foot and begin rolling it up my long legs to my thighs, where I fumble a bit before managing to clasp the garters to it. Running my hand along the sheer silkiness encasing my leg, I am struck by how pleasurable and sexy it feels to be wearing them. After attaching the second stocking and standing, feeling the tug of the garters, I realize that this feeling of pleasure is really erotic.

Lastly, I pick up each "boob' and slide it into the cups of my corset. Then, taking a deep breath, I turn to the mirror. Oh, what a shock! Now I am completely transformed! I can't even recognize myself. I walk toward the mirror, and am surprised to note how wonderfully sexy the slight tug of my gartered stockings, and the soft feel of the silk and satin lingerie feels.

Standing in front of the mirror, it is only the clear outline of my hard cock, which is jutting against the front of my tight silk panties, and my muscular shoulders and arms, which reveal me to be a man. Otherwise, with my hair in long pigtails, I look like a really sexy and well-developed (my boobs are practically bursting forth from the tight confines of my sexy corset) young girl!

I simply can't believe how different I look, and also what an incredibly sexy feeling it is to be dressed like this. I have been selling lingerie like this every day for months, and yet I have never had any interest in wearing it. Now I find myself running my hands over my jutting "boobs", where the nipples are etched against the satin. I then run my hands down the sides of the corset to my slim waist, and turn to see how my silk panties hug the curve of my tight buns. I am just about to begin fondling my hard panty clad cock, when looking up, I notice Jake in the mirror, leaning against the wall, watching me, with a wicked and knowing smile on his handsome face!

I turn to him, not bothering to hide my hard-on, as he's already seen it several times! Jake is standing there, with what looks like the same ultra sexy pink leather mini-dress he showed me in the store, and a bag in his other hand. "You know, you make one really sexy looking girl. I knew you would. I didn't mean to disturb you (with a glance at the bulging front of my panties!), but I brought home this dress from the store, in the hopes you might decide to dress up tonight. I also picked up a pair of matching boots in your size. "You'll need my help zipping up the dress."

Laying the bag with the boots on the bed, Jake unzips the back of the leather mini-dress, and stepping in front of me he holds it open for me to slip my stocking clad legs into it. He has to bend over a little bit, so that his face is facing and only a few inches from my hard panty clad cock, which throbs powerfully in response! I slip first one leg in, and then, I lose my balance, I am so nervous, and I have to steady myself on Jake's strong bare shoulder. He then slides the dress up, over my panties and bulging boobs, and helps me guide my arms through the straps, before slipping around me to zip me up in the back.

As Jake slowly zips up the dress, I feel it molding to my new curves like a glove. It fits perfectly, and tightly. You can even still see the clear outline of the erect nipples of my boobs, which jut against the tight leather! What will people think! Whenever I see a girl with erect nipples showing through her dress, I always find it arousing, and think that she must be turned on by something. Then I notice that my cock is now jutting forth against the tight leather of my dress, and very obvious!

"This dress fits you perfectly! You look so hot, you better be careful tonight. Every guy is going to want to get into your panties, whether they're gay, or straight. You may even be able to pick up a woman there. There are some really foxy girls who go to this club, and it looks as if you're going to have trouble hiding your manhood (this with another glance at my still hard cock pressing against the front of my dress!). I'll leave you now to try on the boots."

Jake's words thrill me. I yearn to turn and have him take me into his strong arms, and to tell him that he is the only man that I want to get into my panties, but I still can't tell if he realizes that he could have me at any point, or even if he is willing to have me. Maybe he is being faithful to Jessica, and is only having fun flirting with me and transforming me for a night into a she-male. I can't imagine that he hasn't noticed that I am attracted to him.

I can't wait to try on the boots and get back to Jake, so I quickly open the bag and box to reveal an incredibly sexy pair of pink leather thigh high boots! I waste no time, but quickly sit down on the bed to slide them on. The feel of my stocking clad leg sliding into the long, soft leather boot, and then the feel of the leather clasping my legs as I pull the zipper up, is very sexy and arousing. Standing, I feel very wobbly at first, so I practice walking back and forth in the room. I find that in order to balance well in these sexy boots, I naturally fall into a feminine movement with my hips and ass swaying from side to side and I love this sensuous feeling of the pull of my garters, and my transformed leather and lingerie-clad body!

Stepping out into the living room, I greet Jake, who gives me a warm and appraising look. I smile and show off by turning slowly around like a runway model. My nervousness is almost gone, and I am totally caught up in playing this new feminine role. "Well, what do you think? Will I pass?"

"You look really sexy and foxy, like a really beautiful woman, and in those "fuck me" clothes, I think you are irresistible", Jake replies with a smile and lustful look.

Screwing up my courage, I respond with a flirtatious smile and more blushing, "is that a promise?"

Jake looks surprised by my boldness, but to my disappointment, he responds only with, "we'll see."

I walk over and sit down next to him, smoothing my dress as I sit. But Jake gets up almost immediately, and says that he needs to get ready himself. He leaves me sitting there, and I take the time to walk over to a wall mirror, and again admire and marvel at my transformation. Then, noticing that my lip-gloss needs to be freshened, I get it from the kit and carefully apply a fresh coat. Oooh, the first time it felt a bit strange and uncomfortable, but this time, feeling very feminine in my ultra sexy outfit, it feels very sexy to apply the shiny gloss carefully to my lips, and I find my cock again straining against the front of my dress!

As I wait for Jake, I again practice walking like a woman in my high-heeled boots. At the same time, I can't help running my hands along my leather clad body, caressing my new jutting boobs, the smooth sides of my dress and my tight panty and leather clad buns. It takes an effort to resist fondling my aching cock, which continues to jut against the front of my dress, but the feel of it rubbing against the tight confines of my panties and my dress is an incredible turn-on!

It isn't long before Jake comes back, and I squirm with desire at the sight of him! He is wearing the same outfit as the one in the picture with Jessica. A black leather body harness with studded straps encases his delicious and muscular chest and shoulders, and he is wearing ultra short and tight black leather shorts, which hug his tight buns, and the bulge of his cock and balls. His muscular tanned legs are bare, except for a pair of masculine knee high black leather biker boots. He still has the sexy black leather choker on.

"How do you like my outfit", he asks?

"You look really hot", I respond breathlessly, devouring him with my eyes. He is such a hunk! What I would give to peel those sexy shorts off of him and take his sweet cock into my mouth!

"I'm glad you like it. Now, before we go, I've got something else for you to wear." He goes back into the bedroom for a moment, and then comes back with what look like straps of pink leather. When he holds them up for me to see, I realize that one of the straps is a slender leather choker like his, but with small feminine sparkling rhinestones, and a single silver "O" ring at the front, and the others are matching, but wider wrist cuffs, also with a single "O" ring.

"As I told you, this is a BDSM club. There is a lot of role-playing that goes on there. You don't have to participate if you don't want to, but everyone is at least expected to dress in either dominant or submissive attire. You can tell that I like to dress up and play the dominant role, and you will be dressed as a submissive", he explains as he helps me to fasten the sexy choker around my neck.

His exciting and provocative words have made me speechless again, as has his nearness to me as he helps me with the choker. I want so much to reach out and clasp his leather-clad buns and pull him against me, but I am still full of doubt as to whether he is willing to be unfaithful to Jessica. By this point I think it is clear that he's attracted to me, but not whether he is ready to act on that attraction. Certainly the enormous bulge of my hard on jutting against the front of my dress like a tent pole, must make it clear that I am attracted to him!

To be continued...

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8 Comments
AnonymousAnonymousover 3 years ago
more please

Great story, great leather, looking forward to more chapters

AnonymousAnonymousalmost 10 years ago
t's very good

t's very good please show a pic. of jake in all of his sexy costumes

PaddlesPaddlesabout 10 years ago

please write more of this story its awesome so far

AnonymousAnonymousover 11 years ago
please continue

I can't wait for the next chapter of this story -- and the chapter after that one -- and the one after that. Your stories are getting me hard thinking about how I would love to dress in women's clothes and get fucked by a hot hunk of a man like Jake. Please continue this story.

AnonymousAnonymousover 11 years ago
Hot leather

Really good story. Loved the leather outfits. Looking forward to more.

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