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...