Transformed Into A Shemale

After dropping our purchases off at the car, we go to Wilson's House of Leather. As I am admiring a sexy black leather ultra mini-skirt while Tom shopped elsewhere in the store, a salesman approaches me and asks if he can help me. I feel an electric thrill of recognition at the voice and looking up I find my best friend John facing me! I had forgotten that he told me that he had taken a summer job at Wilson's!

He looks so fine, as always. He is wearing tight Wilson's leather pants (and now I remember the leather he was wearing when he fucked Nancy) which nicely outline his tight hard buns and crotch and a tight white polo shirt that hugs his tanned and muscular chest and arms. It is somehow amazing after all of my years of friendship with this boy that I should begin to lust after him in this way. As I stand before him and his eyes wander shamelessly over my sexy outfit, I realize that he doesn't recognize me!

John asks me if he can be of help, with a smile on his face. I reply with an especial effort to remove all traces of my male voice. "Do you think I would look good in this," I ask in a teasing voice, holding up an incredibly sexy and short red leather dress against my body.

John's face blushes red in that cute way that I know so well. His reply is more direct than I would have expected and I feel a flush of excitement as he replies, "I think you would look beautiful in that dress. I would love to see you in it, would you like to try it on?"

I agree, and John gestures to the dressing room and then follows behind me. I can imagine his eyes feasting on my leather-clad buns, as he has often told me that he is an "ass man." On purpose, I drop the dress that I am carrying and bend low to pick it up, so that John is treated to a glimpse of the top of my thighs and my sexy pink panties and garter straps.

"I'll be right back. Will you wait here? I'd like to know what you think. I'm so bad at choosing clothes for myself," I say to John, and he assures me eagerly that he won't move until I come back. As I enter the dressing room, I catch a glimpse of Tom, who is watching this whole scene from another part of the store with a smile of amusement on his face. He flashed me a "thumbs up" signal and I give him a smile of thanks.

I stand close to the door, so that John will be able to see me sliding my dress down over my boots and stepping into the new one. Although I don't really need his help, I want to flirt with him, so I slide open the door and ask him to help me zip up my dress from behind.

As he helps me pull the zipper up with trembling hands, I thank him and say, "you have warm hands." John blushes again and is speechless.

"How do I look John (he has a name tag on)?," I ask flirtatiously as I smooth the dress with my hands and pirouette in front of him

"You look really beautiful. That dress fits you like it was made for you. I'm sure your boyfriend will love it," he says.

"I don't have a boyfriend at the moment, so I want to buy clothes that will help me to find one." Do you think boys will notice me in this outfit?, I reply mischievously with a wink and a wicked smile. "By the way, my name is Jessica. I know yours from your name tag."

"It's a pleasure to meet you Jessica," he says taking my hand. "Any guy that doesn't notice you in that outfit must have something wrong with him." As John is saying this he lets his eyes roam over me appreciatively and I am rewarded with the sight of his growing hard on within his tight leather pants.

"Well, I guess I'll take this one. Can you show me what else you have?," I ask.

John proceeds to show me several different outfits, each of which I try on and model for him. His hard on remains constant and obvious against the tight leather of his pants as I flirt more and more openly with him. At one point I notice that they have a leather lingerie section and leading John over to it, I hold up a wicked black leather corset against me and ask him if he thinks I would look good in it. By this time we have become so comfortable flirting with each other that John replies that he wishes that he were the guy lucky enough to see me dressed in it. "I'll be happy to give you that chance right now! Come on, I want to try it on and see what you think."

I have John wait (obviously eagerly) outside the booth as I slip the corset on and attach the garter straps to my stockings and insert my silicone breasts into the cups of the corset. They look completely realistic jutting against the tight leather. I have a moment of anxiety as I note how openly my cock is straining against my panties, but then I decide to conceal it by slipping on one of the sexy leather mini skirts I've chosen. I look and feel so sexy and hot that I feel confident that it is time for me to let John know how much I want him. So, after applying a fresh coat of lip gloss and smoothing my skirt I open the door and motion him to come inside, "I don't think I should step out there dressed like this," I say seductively.

John's eyes are fixed with lust on me and his straining cock is more visible than ever as he comes in and I close the door behind him. "Now, if you were my boyfriend, what would you think if I came to you dressed as I am now?," I ask him softly as I run my hands enticingly along the tight smooth leather of the corset.

"If I were your boyfriend, I would think that you wanted me to fuck you and I wouldn't hesitate...," John replies with a voice choked with lust.

It is the answer I expected from the way he has been flirting with me, so filled with lust for him as well, I step forward and lean forward until my boobs are pressing against his hard chest and whisper in his ear, "let's pretend that you are my boyfriend then." Boldly, I reach down and lay my hand on his clearly outlined leather clad cock and begin fondling it.

John moans with desire and putting his hand behind my head, he pulls my face against his until his firm and lovely lips press against my glossy ones and his tongue slips eagerly into my mouth. His arms encircle me and fondle my panty and leather clad buns as we kiss passionately. Suddenly John breaks off for a moment and whispers that he hears the store manager "I've only been working here a week. If he finds me in here, he'll probably fire me. I want you so much Jessica! I have a half hour break coming up in a little while. Can you wait for me? Maybe we can have a coffee?"

Still fondling his lovely hard cock, I whisper, "I'd rather pull this lovely cock out and get to know you better. Why don't we go to my truck, out in the parking lot?" John seems a little shocked by my suggestion, but readily agrees. He then slips out of the booth and after I slip back into my own outfit, I gather up the corset and my sexy collection of leather and approach Tom at the back of the store, who has been watching me flirt with John with interest.

"He is delicious! I saw him go into the dressing room with you, have you behaved yourself?," Tom asks with a smirk.

"You won't believe it, but he is my best friend! His name is John and I have been lusting after him for weeks and thanks to you, I just had his tongue in my mouth and his cock in my hand! I don't have time to talk, but could I borrow the keys to your truck for a half hour? He has a 20 minute break and I want to slip his lovely cock in my mouth!" Tom readily agrees after I promise him that if the chance arises, I will try to get John to go to bed with all three of us together.

As I pile my selections on the counter, the manager, a middle aged distinguished looking man drops what he is doing and begins to help me, caressing me all the while with his eyes. "It looks like you have bought out the store! Did you find everything you wanted?" He asks.

"Oh yes, John was very helpful" I reply, giving him a wink as I say this. "We are good friends."

"Oh, well I should thank John for bringing in such a good customer."

"You might thank him by letting him have a break for a short time. I'd like to catch up on old times." I say with a wicked smile directed at John. He smiles and flushes under the gaze of his boss, who sends him off for a twenty-minute break with me.

As soon as we turn the corner, I reach behind John and fondle John's tight leather buns and press him against the wall and with my boobs against his chest I ask, "are you ready for the best blowjob you've ever had?"

John replies in the affirmative and I can feel his cock jerking to attention beneath the tight leather of his pants. I then take him by the hand and lead him quickly through the mall and out to Tom's truck. As soon as we have locked the doors I am in his arms, my boobs pressing tightly against his chest through the tight leather of my dress and my glossy lips locked against his sweet firm ones with our tongues swirling against one another. With one hand I fondle his rock hard cock which is straining against his leather pants. John moans in excitement and begins to fondle my tight virgin panty and leather clad buns (I am careful not to give him an opportunity to slip his hand underneath the hem of my dress in the front and discover "my secret").

After a few deliriously sweet moments of making out with John, I pull away and while continuing to fondle his cock I whisper in his ear, "I know you only have about 15 more minutes. I want to see your cock lover. It feels like it must be huge!" As I unbutton and begin to unzip his sexy tight leather pants I think about how much I have been wanting this since the night just three weeks ago that changed my life when I saw his cock erect for the first time. At the time I wanted so much to be Nancy and to wrap my lips around this enormous and gorgeous cock, and now I will have the chance!

I have a sudden shock of surprise as I spread his opened pants and reveal his lovely bulging cock encased in a pair of sexy pink silk panties! "What do we have hear," I ask with a wicked smile, while fondling his rock hard panty clad cock. "These don't look like any boy's undershorts I've ever seen." John's face has flushed red in embarrassment as he replies, "I, uh, have another girl I'm seeing who asked me to wear her panties while I'm at work."

"Oh! I guess she probably never imagined that another girl would get inside your panties. Are you wearing her bra also," I ask as I run my hands up under his shirt to find out?

"No, of course not" he replies. "I don't know why I agreed to wear her panties, but she insisted."

"How do they make you feel lover? Do they make you feel feminine and sexy?"

"They do feel kind of sexy," he replies shyly.

"Well, I love them on you. They look a lot like the pair I'm wearing right now. I think it's a good thing for boy's to wear lingerie. It helps to make them more sensitive.," I say as I continue to fondle his lovely cock through the frilly panties.

I pull down John's leather pants to his knees and then I lower his sexy panties revealing the lovely cock I have been lusting for... It stands to attention rigidly and it must be 10" in length and its round lovely head is oozing pre-cum. "Oooh, John, you have a lovely cock! I don't think I'm going to be able to take all of this in, but I can't wait to try!" I say and immediately I lower my head and lick and suck on the enormous cock head. It tastes so sweet and salty and John's moans excite me as I begin to bob my head up and down letting his sweet cock slide wetly between my glossy lips and taking more and more of his shaft with every downward movement. With one hand I pinch John's erect nipples and with the other I caress his prostate and anus and then I begin to slide a finger into his anus and am rewarded by a cry of excitement from John.

"Oh yes Jessica, your mouth feels so good! I've never had such a great blowjob! Your finger fees so good up my ass! Suck me lover!" he cries thrusting his hips forward and forcing my head lower. John obviously doesn't know it, but one of the reason's I am able to give him the best blowjob he's ever had is because being a boy myself, I know what feel's especially good.

I eagerly suck my best friends cock, pausing very few moments lick and suckle on his cockhead and balls to both tease him and give my jaw a rest. His cock is so huge! I thrust my finger in and out of his tight ass and John squirms in his seat in response.

I can feel my own cock becoming wet with pre-cum within the tight confines of my panties. Ooh, this is such an incredible turn on! I just wish that I could climb up and straddle him and feel this lovely cock slide between my buns! I can imagine the sense of fulfillment a girl must feel that I would experience with this lovely enormous cock filling me.

When I begin to feel John's cock begin to spasm, I am ready as he cries out, "I'm cumming Jessie! Suck me lover! Keep sucking meeee!" In moments hot spurts of John's sweet cum are flooding down my throat and I eagerly swallow them. His rectum squeezes almost painfully hard on my finger as he climaxes. After I feel him slump in release, I continue to suckle the last drops of cum from his softening cock before withdrawing my finger from his ass and looking up as I lick my glossy lips in satisfaction.

"You have a delicious cock, Lover. I wish I had more time to explore your luscious body!" I say as I slide his panties up and smooth them for him. As I do this I can feel his sweet cock stirring again and as I fondle it through the silk of his panties it soon grows hard again. "I wish you had more time John. I'd love to suck this lovely cock again! Will you have any time tomorrow night? I'm staying at a friend's place, maybe you could come over and we could get to know one another better. I want to dress you in a few more sexy feminine things and see how you like it."

John responds immediately that he will have trouble waiting until tomorrow, but we agree to meet at closing time at Wilson's tomorrow and with a last closing passionate, tongue swirling kiss, John hurries back to his job.

As I sit there smoothing my outfit in the truck, I marvel that all these wonderful exciting things are happening to me. I feel so alive as a sexy girl and having been with my best friend John was more wonderful than I had imagined. I am still shocked at having found John dressed in panties and at his willingness to dress up with me tomorrow night. But of course if a sexy girl had dragged me out to a parking lot and sucked my cock, I suppose I would do almost anything for more also...

I am lost in thought fantasizing about John spread out on the bed dressed in panties, garter belt, bra and stockings while I gently run my hands along his strong stocking clad legs as his cock slides wetly in and out of my mouth... Suddenly, my daydreaming is interrupted by Tom's face and tap on the window.

"You look like you've had a good time. How did your best friends cock taste? I know he was having a good time because I watched him through the window. What a hunk! Any chance I can get inside his pants?," Tom asks as he slides in next to me and gives me a brief kiss before starting the truck and heading back home.

"It was wonderful Tom, and you are so great to let me use your truck, not to mention letting me buy all of these sexy clothes! I can't wait to try them all on for you. You won't believe it, but when I finally got John's pants unfastened, I found that he was wearing a pair of sexy pink panties just like mine! I've known him all my life and would never have guessed he would be into that. He told me that his girlfriend had asked him to wear them, but he certainly seemed to enjoy it and I've made him promise to dress up in some of my clothes for me. My thought is that I will get him dressed completely dressed up at your place tomorrow night while telling him that you are away, and then you can drop by as a surprise, and we can see what develops from there...

"That sounds wonderful. I'm getting hard just thinking about being with you two sexy she-boys!

After stopping at a liquor store, Tom drops me off at his apartment and tells me to relax while he goes and gets Dale. I'm a little nervous but Tom reassures me, "By the time Dale has a couple of beers in him and we've smoked a joint or two, he'll be dying to get into your panties. Just choose the moment that seems right to you. Remember, the idea is to first start by giving him a blowjob while I begin fucking you in the ass, and then switch places. We'll tell him it's your "time of the month" and that's why you want us to fuck you in the ass.."

While Tom is gone, I go into the bathroom and freshen my makeup. I remain nervous, but also excited at the thought of being with two sexy hunks at the same time, and especially at the thought of finally being fucked.

By the time Dale comes in, I'm sitting on the sofa drinking a beer. He looks gorgeous! His hair is still wet from a shower and he is wearing nothing but a pair of tight black leather shorts (maybe because he know's I like leather?) a tight white t-shirt stretched over his muscular broad chest and shoulders and a pair of sandals. I feel a little flustered as I stand to greet him, smoothing my leather dress as I do so. I catch the scent of his cologne as he leans over and gives me a light kiss on the cheek.

I offer to get them beers and as I head to the kitchen I can feel Dale's eyes on me from behind. When I return I notice that Tom has had Dale sit at one end of his small leather sofa while he sits at the opposite end leaving me either the separate chair, or a small space between them to sit. I hand them their beers and then choose to squeeze between them and am rewarded by the thrill of the feel of Dale's bare leg and Tom's leather clad leg pressing against mine. I can feel Dale's tension through his strong leg and within moments he lifts his leg to cross it to hide his growing hard on. Tom lights a joint and we pass it around. As we feel the effects of the beer and joint we all begin to laugh and make jokes and Dale flirts with me more and more openly. I begin to get really horny playing the role of a sexy girl and I feel so feminine and turned on between these hunky men.

I can't wait for the opportunity to get these two guys into bed and I come up with a great idea. "Tom took me shopping today and I bought some really gorgeous outfits. Would you guys like me to model them for you." They both enthusiastically agree and I go into the bedroom to change into my first outfit.

I lay all of my beautiful outfits out on the bed. All of my leather and vinyl minidresses and miniskirts, my thigh high boots and my sexy lingerie. My cock is aching within the tight confines of my panties at the thought of slipping all of these beautiful outfits on. As I slip out of my sexy pink minidress and boots, my thoughts run away at the thought of having Tom and Dale run their hands over me, lift the hem of my dress, lower my panties, and slip their cocks into me!

The first one I choose is a red vinyl minidress and matching thigh high boots. First I slip into my matching red vinyl corset, panties and red backseamed stockings. I feel so sexy and feminine as I slip my legs into the sexy boots and zip them up as I imagine Dale's reaction when he sees me. As I admire myself in the mirror, I realize that this is a real "fuck me dress" and I hope that Dale will get the message. I look and feel like a real slut dressed like this. I apply shiny red lipgloss to match my outfit.

I go back into the room and am pleased with Dale's look of utter lust when he sees me. Tom starts to whistle and Dale soon joins him. I note that they are on their 3rd beer, which explains Dale's lack of inhibition and enthusiasm. I decide to give them a little erotic show, smoothing the tight vinyl of my minidress, running my hands slowly over my breasts and ass and twirling around. I can see both of them beginning to squirm in their seats and I let my gaze linger openly on Dale's cock, which is obviously rock hard and is outlined against his tight shorts. Although I think I could go right over now and slip into Dale's arms, I am waiting for some signal from Tom that hasn't come yet, so I slip back into the bedroom, after promising to be back very soon in an even sexier outfit.