2 comments/ 163046 views/ 12 favorites First Experience With A Man Ch. 1 By: girlboybootsie I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking guy. I'm tall with blond hair, blue eyes, and an athletic build. I had a big collection of pornography, and pictures of beautiful girls dressed in sexy lingerie, and leather especially turned me on. It was probably for this reason, that I accepted the job at Frederick's of Hollywood, in the local mall. My old girlfriend, Jessica, had worked there, and there was nothing that had turned me on more, than the sight of her dressed up in those ultra sexy outfits. I needed a part time job at the time while I was at school, and when she told me of the position; I felt a strange thrill at the thought of working with all that sexy lingerie and helping women choose outfits. I fantasized what it would be like to help really foxy girls choose wicked outfits, and I guess I imagined I might manage t go to bed with some of them.... It was my first day after my training, and I was left alone in the store for the first time. It had been a quiet morning, and I was bored stiff at the counter, when this young guy, about my age walks into the store. I had been told to expect the occasional transvestite in the store, but I was not prepared for the sight of this young guy, who was dressed in the most masculine way I could imagine, all in tight black leather. Leather pants, boots, and jacket. As I told you, women dressed in sexy leather have always turned me on, but this was the first time I had ever really noticed a man all dressed up in tight leather. He was a really good-looking guy, with stunning blue eyes, dark hair, and a powerful athletic build. And his outfit was really tight! His pants were stretched so tightly across his tight ass, it looked as if they were molded. And in front, I was afraid he would notice my glance at the bulge, contained only barely by his pants. He didn't look like what I imagined a cross dresser might look like, but I was curious, and found myself following him with my eyes as he walked around the store, holding up sexy garter belts, corsets and other feminine lingerie and examining them. I approached him and asked if he needed help. He smiled back at me and said with a smooth deep (masculine) voice, "no thanks. I'm just looking". I felt strangely disappointed at his answer. I wanted to talk with him, and to know why he was in here showing so much interest in women's lingerie. After a short time, while I watched him covertly, as he walked around the store, he brought up a sexy pink satin corset, with white ruffled lace trim, and matching panties. I asked him if he needed matching stockings, and he said yes, in size large. At that point the thought crossed my mind that maybe I was serving my first cross dresser, so I commented on his selection, "You've made a nice choice. I'm sure your girlfriend (he wasn't wearing a ring, and he seemed to young to be married!) will love it". He laughed at that, and fixing me with his beautiful eyes and a smile, he responded, "yes, I'm sure he will look great in it". I was dumbstruck by his response, and he smiled all the more as he noticed me blushing. I had never knowingly spoken with a gay guy before, and he didn't fit my image of a gay man. As I said, he seemed masculine, and just like other guys, other than the tight leather outfit he was wearing. As I prepared to ring him up, he told me that he worked upstairs at Wilson's leather, and that he deserved the 10% discount for mall employees. I took his credit card, and with a teasing smile and tone of voice, he said, "well, you can see how my workplace effects how I dress. That's one of the reasons I work there. How about you? I've never seen a guy working in a lingerie department. Are you like my boyfriend, and enjoy dressing up as a girl?" I stammered a denial at his outrageous comment, and I felt myself blushing furiously. "Too bad", he responds, his eyes and smile holding me transfixed. "I'm sure you get a good discount, and you'd look really hot in something like this corset! My boyfriend says that the feminine feel of lingerie makes him feel sexy and turned on. He would go crazy in here! I tried it once, but I prefer leather, as you can see. Maybe you should try it sometime". To humor him, and because I couldn't think of anything else to say, I respond, "maybe I will". He gives me a wicked looking smile at that, and then holds out his hand in introduction, "I'm Jake". Taking my hand, he gives me a strong handshake, as I stammer, "I'm James. It's nice to meet you, Jake". As I hand him his lingerie in the bag, he invites me to come by his store. "If you see anything you like, just tell me, and I'll get it for you at my 50% discount. We have some great clothes, and if you get into it, we also have some really sexy leather girl's outfits". I blush again as I thank him, and I also let him know that in future, he can also have my discount. As Jake walks away, my mind is racing after this unusual encounter. Watching him as he strides away, I can't help noticing how lean and powerful his leather clad body is, and I wonder that he prefers men to women, when he could no doubt have any woman he wanted. After Jake left, as I was putting out a new display of sexy black satin garter belts, I kept going over our meeting in my mind. I wondered what it would feel like to wear a tight leather outfit like his, and with a thrill I realized that I could go and buy one at half price at his store! But the thought of seeing him again, made my heart race. Although I had never spoken with a gay man, I had the distinct feeling that he had been flirting with me. The thought, although new to me, was somehow thrilling, that this self possessed, handsome guy, dressed all in black leather wanted me! And even more shocking, he seemed to like the idea that I might dress up in some of this sexy lingerie, like a girl! That night, as I lay in bed, I resolved to go into his store the next day and take him up on his offer of a discount. The thought of sliding into tight leather pants like his made my cock hard, and as I lay there stroking my hard, throbbing cock, I had to keep banishing the thought of Jake from my mind, as I focused instead on the image of my girlfriend fondling me through the tight leather of my outfit. Although I had managed to banish the conscious images of Jake, that night I dreamed of being with him. In my dream, Jake was helping me slip on my new leather jacket. My pants were already on, and my cock was straining with excitement against the tight leather. As Jake helped me button the front of my jacket, he suddenly took me in his strong arms, placing his hands against my leather clad buns and fondling them and pulling me against his strong chest, as he pressed his lips against mine, sliding his hot tongue deeply into my mouth! The erotic thrill I feel is incredible, and I eagerly kiss him passionately, as our hard leather encased cocks rub against each other! Breaking our kiss, Jake tells me that he wants me to suck his cock. Although even in my dream state, I realize that I have never done this before, I sink right away to my knees and unzip the tight leather of his pants to reveal his huge, bare cock, which is throbbing with excitement. Tentatively, I begin to lick his enormous cockhead. Then, with real eagerness and excitement, I let it slip into my mouth, as Jake cries out, "Oooohhhh, yes, suck me deeply! That's it lover!"..... And then, as is the way with such dreams, I woke to my alarm clock, with a huge hard-on and a powerful desire to be with that sexy hunk. I immediately begin to stroke my hard cock, this time trying to keep the sensation of sucking Jake's cock in my mind. Even then, as I soon reach an incredible climax, my cum jetting into the air, I realize that my life, and my sexual orientation have changed forever. Somehow, I'm going to try to experience that dream for real! My only concern is that although I am quite sure that Jake was flirting with me, he may be loyal to his boyfriend. When I head to work, later that morning, I resolve to visit him as soon as his store opens. I arrange to have another salesgirl cover the store, and with nervous anticipation, I stroll into Wilson's just after it opens. Luckily (and terrifyingly!), Jake is the only one in the store, and he smiles in recognition when he sees me. He's again dressed from head to toe in sexy tight leather, and I feel a thrill as he takes my hand and tells me that he's happy to see me again. I feel myself blushing under his warm, penetrating gaze, but manage to smile back and let him know that I'm also happy to see him. I tell him that I'd like to take him up on his offer, and choose a couple of things from his store. Jake asks me what I would like, and I respond, "Well, I kind of like the outfit that you have on...". He gives me an even warmer, possibly knowing smile, as he leads me to a rack of shiny black leather pants. "This is really soft leather, and feels really great on. Do you want to wear them tight, like me"?, he asks with a smile. Although I am blushing furiously at his direct, flirtatious manner, there is no reason for me to not tell him the truth. After all, what I really want is to get into his pants. "Sure", I respond, still blushing. Jake then takes out a tape measure, and stepping behind me, he wraps it around my waist. At his touch, my cock begins to harden, and I resist the urge to melt backwards, into his arms. Jake picks out a pair, that is two sizes smaller than I normally wear. He assures me that they will stretch, and become more comfortable. He then helps me pick out a black leather shirt, similar to his. Again, at my request, he chooses one, smaller than my normal size shirts. "Go on into the dressing room and try them on. I want to see how they fit", he says, leading me to the dressing room with his hand on my back. As I enter the dressing room, my mind is swirling with the intoxicating feel of being close to Jake. It seems amazing to me that when I started the day yesterday, I had no idea that a man could be so attractive. Slipping out of my clothes, my cock is freed from restraint and springs forward, rigid with excitement. I waste no time, but slip the tight leather pants on, over my bare cock. Jake has judged the size just right. I have to suck in my breath a little to zip them up and button them, but like on Jake, they seem to be molded to very contour of my tight buns, and to my rock hard cock, which is clearly outlined against the front of them! Oohhhh, the smooth leather feels so sexy against my bare skin, and I revel in the sensation. I stroll back and forth within the dressing room, feeling the way they stretch back and forth as I move, loving the erotic feel of them, and the way they so clearly reveal my 8" hard cock, which is jutting forth against the tight leather. I then slip on and tuck in the smooth leather shirt, which hugs my broad chest and shoulders. I feel so sexy! Suddenly, I hear Jake call out, "Hey, how's it going? Come on out, I want to see how you look"! What am I going to do? I can't go out there like this, with my cock standing at attention, and totally visible! And yet, I am so excited by a combination of Jake's forceful physical presence, and the feeling of these sexy clothes, that there is no way that my hard on is going to go away. So, I quickly untuck the shirt, and pull my hips back a little, so that my hard cock is not so visible. Stepping out of the booth, I come face to face with Jake, who whistles when he sees me. "Hey, you look great! But you need to tuck in that shirt.", and with that he approaches me and begins tucking in the hem of my shirt! As the huge outline of my hard cock is revealed, Jake looks into my eyes and smiles. "Are the pants too tight? I think maybe I misjudged your size!". I feel like I'm going to die with embarrassment, but I manage to stammer that the size is fine, and that I'm sure they will stretch. Looking directly down at my cock, and then into my blushing face, and says, "At this rate, I'm sure they'll stretch, too!" Although I have never been so turned on in any girl's presence, this is so new to me, and my conflicting feelings of arousal and embarrassment are so strong, I excuse myself as soon as possible, and scurry back into the changing room. When I come out, Jake takes the outfit from me, and tells me that he will have to pay for it, in order to get the discount, and suggests in a casual manner, that I come by his house, after work to pay him and pick up the outfit. I quickly agree, and take down his address, which is within walking distance. He also asks me for my shoe size, because he says that I need some boots to wear with my new outfit. He tells me that he has a friend that owns a boot store, and that he will bring over a couple of pair for me to try on, with no obligation. Inside, my mind is reeling with the realization that he can't be going to all this trouble, unless he wants something from me and I hope it is more than a reciprocal discount at Fredericks! Jake then asks me to come over to the other side of the store, to see some other outfits I might like. Leading me into the women's section, he selects and holds up against my body, an ultra sexy, hot pink leather minidress. "You would look great in this, and I think it's your size. Would you like to try it on? I know that you said you had never worn women's clothes before, but with your long hair, and gorgeous face, you would look really hot!" Oh shit! What can I respond to this outrageous comment! He is holding the dress against my body, and I can't help myself from feeling the soft leather, while at the same time my face is again blushing furiously, and I respond that maybe I can try it on another time. "I'll remember that", Jake says with a smile. "Listen, why don't you come over to my place tonight, to pick up your outfit. I need to code it in a special way, and I don't have time right now. Besides, we can have a couple of drinks together." Before I can stop myself, I blurt out, "will I meet your boyfriend"? I am shocked and embarrassed by my boldness, but Jake takes it in stride, as he says in parting, "No, he's away for a couple of weeks. It'll be just us." I don't know how to respond, so I just stand there dumb, as Jake gives me directions. He leans over the counter as he writes out the directions, and I can smell his masculine scent, mixed with the sexy leather smell of his outfit. He is so incredibly good looking, and I am so turned on by him! I agree to meet him at 7pm that night, and as I walk away, I find that my cock is again rock hard, and my mind is swirling with expectations and excitement. The main question is, is it all my imagination, or does he want to go to bed with me? If he does, although I am still awkward and shy with the newness of being wanted by a man, I intend to let him have me. The power of the attraction I have for him is unlike any I have known. As I walk through the mall, I look around and check out other guys. I spot several, that I think are good looking, but although I examine my reaction carefully, I can't say that I feel anymore attracted to them than before. There is something about Jake's powerful personality and sense of self assurance that combines with his beautiful face, body and sexy outfit that makes me want to please him. My workday at the store seems to last longer than usual, I am so fired up with impatience. My mind continually returns to images of Jake, and the dream I have ahd of slipping his hard cock into my mouth. I wonder if having the real thing could be as wonderful as my dream and fantasies. I had heard that gay men usually took either the male or female role in sex, and I wonder why it is that I seem to be fantasizing only about taking the submissive position of falling to my knees and sucking his cock. Certainly the idea of having him suck my cock is exciting, and also the idea of peeling off his tight leather pants and fucking his sweet ass. But somehow I am more excited about the idea of satisfying him, sucking his cock until he comes in my mouth. What will it taste like, I wonder? What if he wants to fuck me? That thought is a little scary. I once tried to fuck a girlfriend up the ass, but she made me stop because it hurt her. I wonder if he would want that, and if so whether I should let him. Suddenly my daydreaming is interrupted by a really foxy girl comes in and asks for my help in choosing some really ultra sexy and wicked outfits, and amazingly, I don't pursue her as I normally would have. In fact, as she tells me that she wants something really sexy to please her boyfriend, and as I select an ultra sexy satin corset for her to try, the wild thought goes briefly through my head, would I also be willing to please Jake by wearing something wicked and feminine like this? Eventually, the day ends, and I rush home to take a shower, eat and get ready for my visit to Jakes. After eating a light meal, I do some push ups and curl some dumbbells, so that my muscles will be pumped up and defined. I shower, shave, and afterwards, apply some nice cologne. I brush my long blond hair out, and admire myself in the mirror. My naked body is tanned, lean and after almost a year of weight lifting, my muscles are well defined and sculpted. My cock becomes hard with the realization that I am trying to imagine what Jake would think of my body, and soon, all 9" of my hard cock is jutting forward. Since I don't have any leather to wear, I choose a super tight pair of jeans, which reveals the bulge of my cock and balls clearly, and then a tight black t-shirt, which hugs my muscular chest and my biceps tightly. I hope that he will find me attractive, even though I'm not dressed up like a girl! Finally, it is time to go. I am so excited and nervous about what this evening may hold! It doesn't take me long to find Jake's place, which is located in an expensive condominium building. I quickly find a parking place, take the elevator to his floor, and then find his door. Taking a comb, I quickly run it through my long hair, tuck my t-shirt in and try to compose myself. I then ring the bell, and within moments, beautiful Jake, his hair obviously still damp from a shower opens the door and is with me. I can smell a fresh masculine cologne emanating from him, and this scent is mixed with the erotic smell of new leather. He is dressed in what must be a brand new pair of tight black leather pants, a tight black leather vest, which reveals his tanned, broad and muscular shoulders and arms. Around his neck, he's wearing a sexy black leather choker. I feel overwhelmed, and again, instantly aroused by his powerful presence. As he shakes my hand warmly and dazzles me with his smile, my cock, against my will, hardens until it is etched against the front of my tight jeans. I try to hold his eyes, hoping he won't notice, but he does give me an appreciative glance over, and his smile widens as he says, his eyes directly on my aching hard-on, "nice outfit". "Come on, come into the living room and I'll get you a beer". Jake leads me into his expensively furnished living room, and has me sit on his leather couch. As he turns to go get our beers, my eyes move to his exquisite leather clad buns and his long legs, which are beautifully defined by the tight leather of his pants. With women, I have always been an "ass" man. Gazing at Jake's tight ass, so much more tight and hard than a woman's ass, I find myself lusting for the first time after a man's ass and fantasizing about how wonderful it would be to run my hands over those sweet buns and fondle them. First Experience With A Man Ch. 1 Jake is back in a moment with a couple of cold bottles of Heineken. Drawing up a chair, he sits so close in front of me that are legs are almost touching. Jake is so friendly, he (and the beer) soon puts me at ease and soon we are chatting away like old friends. My first beer goes down quickly, and Jake immediately fetches me another. "Well, you know that I have a boyfriend who dresses up like a girl. How about you, do you have a girlfriend? I would imagine that you are very popular among the girls, you're so good looking.", Jake says with a smile, which becomes more mischievous as he notices me blushing. "I'm seeing a couple of different girls right now. I'm not in the midst of a steady relationship", I respond, still blushing. "What's it like to work in a lingerie store? Do you like helping pretty girls choose wicked and sexy lingerie?" "Yeah, sometimes it's a real turn on". "Do you get many guys like me, buying corsets and stockings for their boyfriends, or themselves"? "No. I mean, there are occasionally some older guys who come in, and I would guess they are buying for themselves, but you were the first"., I stammer in response. "Were you surprised when I told you that I was buying the corset for my boyfriend"? "Yes, very! At first I thought you might be shopping for yourself, but you don't seem the type. I mean, you seem very masculine, and the clothes you wear are". "Let me show you a picture of Jessie. Jessie is his male name, but I call him Jessica, as she is always dressed up as a girl when she is with me. In fact, I think of Jessica as a girl, and as I've told my friends, I feel more straight, than bisexual with Jessica" Jake gets up and returns a moment later with a picture of the two of them. What a picture! They seem to be posing at some kind of erotic dance club. Jessica is wearing a black vinyl corset with gartered black stockings and thigh high vinyl boots. I have to admit, she looks absolutely gorgeous and sexy! In fact, if it weren't for her athletic build, I don't think I could tell that he was really a man. She has long blond hair (kind of like mine), and her make-up is perfect, making her face look feminine and beautiful. What must be fake "boobs" are jutting forth against the front of the vinyl corset. In the picture, Jessica is posing with Jake, who is dressed in skintight black leather shorts, black leather boots, and some kind of studded black leather body chains! Jake's strong arms encircle Jessica, and feasting my eyes on his largely bare hunky body, I am totally turned on and envious of Jessica! I wish it were me, with his beautiful body pressing against me, and his strong arms holding me! "Jessica is really foxy! It's hard to tell that she is really a guy. So, she dresses like a girl always? Has she had a sex change operation?" "No! I think of her as a girl, and as I said, I don't really think of myself as gay, because I find real women attractive, but I am most attracted to good looking guys dressed up in girls clothes. I wouldn't want to be with a transsexual. Underneath those sexy clothes Jessica's body is totally hard and masculine, but she loves to dress and behave like a girl, and I find that a total turn on". Jake's words shock me. Is this why he keeps suggesting I should try dressing like a girl? If I want him, do I have to dress up like a girl to have him? Am I willing to do it? The thought of dressing up and acting like a girl is so foreign to me. I think I would probably look ridiculous, not like his beautiful she-male girlfriend. "Well, looking at Jessica, I can see why you are attracted to her. She looks like such a fox, and that is such a sexy outfit. By the way, where did you take the picture"? I respond, still holding the picture. "Oh, that's the "O" club, not far from here. I go there often. It's a great place for people into the BDSM scene, and fetish clothes. I was thinking of going there tonight, would you like to come with me"? "Yeah, that sounds like fun. But I don't think I have the right clothes for it. Can I go just dressed in my new clothes"? Jake laughed. "No, I'm going to change into something a bit more wild. I'd loan you some of my clothes, but I don't think they'd fit. Hey, why don't you wear something of Jessica's? I think her clothes would fit you nicely, and you'll love this club, it's really fun". Seeing the look of doubt, and confusion on my face, he adds, "Oh come on! It'll be really fun, and I promise you that no one will recognize you. I even promise not to hit on you"! I don't know if he realizes that my whole purpose in agreeing to his idea, will be to get him into bed, but I agree with a shy "ok, I'll try it". By this point I have a pleasant buzz going from the beer, and Jake's presence is overpowering any last resistance I have to this wild idea. "Great! Wait right here, we'll start by putting on your make-up, so that no one recognizes you. I often do it for Jessica, and I'm really good at it." Every time Jake gets up, I admire his tight leather clad buns. After disappearing from the room, he doesn't give me much time for second thoughts though, but re-appears a moment later with a make-up kit. "I'm going to do your hair first. Just come over here and sit in this chair, so that I can get behind you". I do as he bids, and he then runs a brush quickly through my long blond hair. He then gathers it up on the sides and makes two long pigtails. I am speechless, and I know that my face is red from blushing. What is he trying to do, make me look like a schoolgirl? After finishing my hair, Jake kneels down in front of me and leaning close, so that I can feel the warmth of his breath on my face, he begins applying eye make-up, and then a little powder and blush to my cheeks. "You don't need much, because your skin is so beautiful, and I want you to look like a young girl". As Jake works, I hold as still as possible, but Jake's nearness, and the masculine scent of his body and the leather of his clothes has made my cock rock hard within the tight confines of my pants. It doesn't take Jake more than 10-15 minutes, before he hands me a stick of glossy pink lip gloss and a mirror and says, "you better put this on yourself". Taking the mirror and the lip-gloss, I am astounded at the change in my appearance! With a little make-up, and a change in hairstyle, I find a stranger looking back at me in the mirror. I apply the wet pink lip-gloss carefully over my full lips, all the while marveling at my transformation. Not only does my face now look feminine, but I would go so far as to say that I look like a beautiful girl! "Wow, I can't even recognize myself", I say to Jake. He is wearing a big, satisfied smile and replies, "No, instead of a good looking guys face, you now have a really beautiful girl's face. I knew you would look gorgeous. Now, we need to transform the rest of you". To be continued... First Experience With A Man Ch. 2 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...