First Experience with a Man

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.