Transformed Into A Shemale

bygirlboybootsie©

Our cocks press and rub against each other through the leather and denim of our clothes and tom grips my firm buns through my tight shorts and my hands find and then fondle his through the sexy leather of his pants. I can feel the power of Tom's hard muscular body as he presses it against mine and it is such an incredibly sexy feeling! I feel that I am totally in Tom's control and it is somehow exciting to realize that Tom could force me to do anything, even if I tried to resist....

I am panting in lust as Tom breaks our kiss and leads me quickly into his bedroom. I feel a thrill as I look at his bed and see the red satin sheets and poles with leather cuffs at every corner!

Leading me to the bed, Tom has me sit down on the sexy smooth sheets. "I'm going to tie you up Jessie. Don't worry, I'm not going to hurt you.," he says, and not waiting for my permission, he gently but firmly pushes me onto my back and taking one of my hands he swiftly attaches my wrist to the buckle. I feel a thrill of fear, but I am paralyzed by indecision. Do I want to allow him to do this? Before I have a chance to even ask him to slow down, I find my arms securely bound by the soft leather cuffs and testing them, I find that I am completely unable to pull my arms free.

Tom then swiftly attaches my legs in the same way and I find myself lying spread eagled on the bed, completely in Tom's control. He looks me over, smiling wickedly and says, "Again, you don't have to worry about being hurt. You're going to love everything that happens hear today, but there may be some things that you might not have wanted to try at first, and now you won't have any choice!

He then kneels beside me on the bed and taking a pair of scissors, he begins to cut my shirt off of me! "Hey wait a minute!" I cry. "What the hell are you doing!"

"Don't worry Jessie! I'll provide something for you to wear when you leave." He replies calmly, but with a forceful tone that leaves no room for disagreement. "Don't struggle" he says. By this time he has begun cutting my shorts off, so I lie very still. I don't wear any underwear usually (at least in those days), so as he pulled away my shorts, my bare cock was revealed to him. It had softened somewhat during my struggle, but that changed quickly when Tom leaned over and without hesitation slipped its head between his lips! Within seconds I was once more rock hard at the incredible sensation of having his warm mouth engulfing me. I began squirming and pushing myself upward as he expertly slipped the entire length of my cock into his moth and began sliding it in and out for a few ecstasy filled moments before pulling his head away. After a few incredibly sweet bobs of his head, Tom pulled his head away. I groaned in disappointment, and he responded by saying, I don't want you to get too used to that Jessie. While you're with me, your main purpose will be to satisfy me, to take this cock (he begins to fondle his cock through the tight leather of his pants) into your mouth, and up that sweet young ass of yours. If you obey me in all things, I may let you cum in my mouth. Do you understand?"

I nod my head mutely while I squirm in frustrated lust. I am beginning to find the sense of being powerless and in the control of this sexy dominant man to be really exciting! My hard buns slide against the sexy soft satin sheets and my cock is raised like a stiff pole.

Tom gets up off the bed and looks down at me and I can almost feel his eyes caressing me, as he looks me over. "I have something to show you," he says. Going to his dresser, he removes something and turning to me, I see that he is holding up a pink satin corset, with white lace trim and dangling garter straps. "Do you like this Jessie?," he asks.

I am puzzled by his question. It is a really sexy and pretty piece of lingerie, but why is he showing it to me? "Yes, it's very pretty" I reply.

Walking over to the bed, he lays it gently over my chest. "How would you like to wear it?," he asks.

I am almost too stunned to speak. How dare he! Just because I have sucked his cock and am yearning to have him fuck me, doesn't mean that I want to be his girl! Although it is an ultra sexy corset and I would love to see a sexy girl in it, the thought of wearing it myself threatens my sense of masculinity, which at my age at the time, was important to me.

"I won't wear that Tom!" I reply angrily. "Don't even think about it!"

"Oh yes you will Jessie. Even if I have to force you into it! But let's not make up our minds too quickly. Let me tell you what we're going to do, once I have you dressed up like a sexy young girl..." He says, kneeling next to me and unzipping his sexy leather pants. Unleashing his gorgeous cock from its constraints, he straddles my chest with the tip of his hard cock resting across my chin and lips. Looking down into my eyes he says, "If you want this cock again between your lips, and I know you do, you will have to do as I say. Only when you are dressed as a sexy she-girl in this sexy corset with its matching panties and sexy stockings attached, will I let you suck me again."

Raising himself, he caresses my chest through the soft satiny fabric of the corset. "We're going to turn you into my feminine young girlfriend, and you're going to love every minute of it!" he exclaims and lowering himself, he rests his hard body on top of mine and I feel the tip of his cock tantalizingly pressing against my virgin anus. I find myself pressing my buns against his cock in eagerness, but as soon as he feels this he raises himself and says, "I know you want it hard up your ass, just like a girl. Just admit it to me. Tell me you want to dress up like a sexy girl, and I'll fuck you hard and deep until I cum deep within this sweet young ass!"

I am in the grip once more of my lust for this sexy leather clad hunk who is dominating me so completely. Although the thought of dressing up like a girl seems strange to me, the promise (and threat) that he will let me have his delicious cock once more and will fuck my virgin and eager ass makes me decide to go ahead with it. "Ok Tom, I'll do it for you. But remember your promise, as soon as put on what you tell me, you have to let me have your sweet cock again," I say in surrender.

"I knew you would see it my way, Jessie. Don't worry, I'm dying to fuck you once I transform you into a girl!" he says and begins to unfasten my restraints. Once I am free once more and standing, he leads me to the bathroom and tells me that my legs need to be shaved and smooth, before we can put stockings on. Although I hadn't planned on it, I am now fully under his power and I go along submissively, and after a shower, he has me raise my wet legs one at a time while he lathers them with shaving cream and slowly shaves all of the hair off of them. Although I hate to admit it, the feeling of the razor along my legs and being naked in front of my male lover this way keeps my cock rock hard the entire time. After shaving both legs and also my arm pits. Tom dries me with a soft towel and leads me back into the bedroom where he lays out my sexy corset, along with a matching pair of panties and sheer white, backseamed stockings.

Standing me in front of a mirror, Tom then hands me the pair of frilly pink silk panties and commands me to put them on. I obey hesitantly, slipping my legs through them and then pulling them on and smoothing them over my tight buns and throbbing cock. Although I won't tell Tom this, the sensation of my hard cock straining against the tight smooth silk of the panties is exciting!

I then accept the corset and with more eagerness I slip it on and Tom helps me to tighten it from behind. Sitting on the bed facing the mirror, Tom then helps me to slip the sheer white stockings on my long legs and attach them to the garters. He then takes two silicone "boobs" and slips them into the cups of my corset and then raises me to my feet.

I feel an electric thrill at the sensation of the sheer stockings on my smooth legs and the pull of the garters. Facing the mirror, I find myself posing and running my hands over the sheer satin of my corset and my new "breasts."

Tom looks on with a lustful look and a smile. "I told you you'd love it. You feel and look ultra sexy and feminine, don't you?."

"I guess I do...," I stammer in embarrassment, all the while with my eyes glued to my transformed feminine self in the mirror.

"I promise you that before the day is out, you will never feel sexier, than when you are dressed up and acting like a girl. I have one more item for you to wear before we put on your makeup. Going to the closet, he returns with the most sexy boots I have ever seen! They are thigh high, high heeled pink leather boots and I can't wait to slip them on!

As I slip my smooth stocking clad legs into these sexy leather boots, I can feel the pre-cum from my cock soaking through my sexy panties! Oooh, what a turn on to rub my hands along the length of the smooth leather! Standing, I carefully strut back and forth in front of the mirror, swaying my ass like a girl would. Tom is forgotten for a moment as I exult in the sexy feminine feelings washing over me. Although I don't have any makeup on yet, my young face and long blond hair combined with the incredibly sexy outfit and my new boobs jutting forth from my sexy corset, makes me look like a sexy and foxy girl!

"Come with me Jessie, so we can finish turning you into the sexy girl you want to be, then you can look at yourself all you want in the mirror!" He says taking me by the hand and leading me to the bathroom. Sitting me down in a chair, he pulls out a full make-up kit and begins by applying sexy pink lip gloss, to my full lips. He then adds blush, mascara and eyeliner. He works so quickly and obviously professionally, that I suspect that maybe he works in a beauty salon. While he is working, I let my hands caress all of the sexy outfit covering my body so tightly, from the leather boots, to my panty clad cock, to the satin sides of my tight feminine corset. I love the taste of the lip gloss and running my tongue along my glossy lips.

After finishing with my face, Tom spends a few minutes brushing my hair and then inserts a pair of pretty berets. Then, leading me back into the bedroom, we stop once more before the full length mirror and I am astonished by the sight! Instead of a 16 year old boy, I now see a really beautiful and sexy young girl. If it weren't for the well defined muscles in my shoulders and arms and my clearly outlined cock pressing against the tight confines of my panties, I don't think anyone would be able to tell that I am really a boy!

"You are now a gorgeous girl Jessie. How does it feel?," Tom asks, while pressing his hard body against me from behind until I can feel his leather covered cock pressing between my panty clad buns.

Reaching behind me, I cup Tom's tight leather clad buns and rub my own panty covered buns against him as I reply, "Ooh, Tom, you were right lover. I can't believe how sexy I look and feel. I can't wait until you bend me over and slip your gorgeous cock up my ass because I think only then will I really be able to relate to what a girl really feels like.

"Be patient. Before the day is through, I'm going to lower those sexy panties of yours and fuck that sweet virgin ass of yours! But first, I want you to learn to act and feel like a real girl. I have a couple of more items I want you to wear, and then we're going out for awhile."

The thought of going out dressed up as I am sends a thrill of fear through me, but at the same time, I am excited at the thought of trying to pass as a girl out on the streets.

Tom returns from the closet holding up the sexiest sweet pink leather minidress! "Ooh Tom, that dress is so sexy! It matches my boots," I gush, already feeling very possessive about my outfit.

Unzipping the dress, Tom helps me wriggle into it and then zips it up from behind. It is so snug, my breasts jut against the smooth sexy leather and it hugs my panty clad buns so tightly, and you can still see the bulge of my throbbing cock in the front! I strut some more in front of the mirror, running my hands over the smooth sexy leather. The dress is so short, I can see the garter straps attached to the top of my stockings and when I lean over, you can see my pink panty covered buns!

Tom slips his hand under the hem of my dress and cupping my buns, he pulls me against him until my boobs are pressing against his chest and I can feel our cocks, both hard and throbbing and covered with sexy leather pressing against each other. "You are such a hot girl now. I'm going to call you Jessica from now on. Come on, take your purse and lets go," he says, handing me a pretty pink leather purse and leading me to the door.

As we emerge into the bright light, I feel very self-conscious, so I lean against Tom as we walk and he slips his arm around me possessively. Almost without conscious thought, I find myself walking with a feminine sway. I love the feel of my garter straps pulling on my stockings, the leather of my dress rubbing against the smooth sexy satin and silk of the lingerie I'm wearing underneath and the sound of my sexy high heels clicking on the pavement!

Suddenly, Tom veers to the right and leads me to the front porch of one of the units, where a hot looking young guy, blond haired, tan with a gorgeous lean and athletic body is sitting reading a newspaper. He's wearing nothing but a tank top and shorts. As Tom approaches, he stands and shakes hands with him as Tom says, "Dale, I'd like you to meet Jessica, my new girlfriend."

Tom reacts by taking my hand and kissing the back of it! "Jessica, it's a pleasure to meet you."

I find my face flushing with embarrassment and my hands nervously smooth the hem of my dress as I reply in the most girlish sounding voice I can manage, "It's nice to meet you too, Dale."

Tom seems to be devouring the sight of me as he says, "What a lucky guy Tom is, you are absolutely beautiful!"

I feel like I will die with embarrassment, but at the same time I find myself reacting at some level to his flirting tone as I thank him and as Tom makes motions to leave, I say that I hope I'll see him again. As we walk away, I can feel his gaze on my tight leather covered buns and I swish them provocatively and reaching behind, I let my hand caress them with an inviting motion and I can hear him sigh in frustration.

As we get into the truck, Tom turns to me and says, "I can see you've already learned to flirt. You had poor Dale panting in lust by the time we left. I've always wanted to get him into bed, but he's too straight. How would you like to take him to bed? I could tell that he was dying to get into your panties, although I think he would be surprised at what he would find there!"

"He is gorgeous," I reply. "It was such a turn on to stand there flirting with him, knowing that he was thinking of me as a girl and didn't know that I am really a boy. "I would love to go to bed with him, but I would be afraid of what his reaction would be once he discovered that I'm not a real girl."

"I have an idea Jessica. Let's spend the day letting you get used to behaving like a girl, and then we will come back and invite Dale over for a drink and get him stoned as well. You can seduce him and invite him to share you with me in bed. I'm, sure he'll want you so badly that he won't hesitate. Then when you've got him totally turned on, you can pull out his cock and start sucking it. I'll lift the hem of your dress from behind and start fucking you, and then before he cums in your mouth, we can switch positions, being careful to guide his cock straight into your ass and while he is fucking you, I'll guide his hand to your cock. He'll realize that you're a boy only after he is in the midst of fucking you and will be unable to stop."

Tom has gotten totally excited by the idea and as he is explaining his plan, his hand is fondling my panty clad cock through the leather of my dress. "What do you think of my plan"? he asks.

"I love the idea of having both opf you guys in bed at the same time, and the thought of sucking a cock and being fucked at the same time is a total turn on, but I'm still worried about what Dale will do once he discovers I'm a boy!"

"Let me worry about that Jessica. I'm bigger than he is and I wouldn't let him hurt you. Just concentrate on what it's going to feel like to have two men at the same time."

"OK," I answer nervously. Tom pulls into the parking lot of a big mall then and taking my hand as we leave the car leads me in. It is a totally new experience to walk through the hallways of a mall I have often gone to, while transformed into a foxy girl dressed in ultra sexy clothes. I wonder what my reaction will be if I run into someone I know. The tap of my heels reverberates on the marble, and when Tom makes mention of it, I hastily carry my purse in such a way that it covers the visible bulge of my cock against the front of my dress.

As we walk through the hallways, I become conscious of people, mainly men, glancing my way and following me with my gaze. I realize with a thrill that it's not just the site of a pretty girl that's attracting their attention, it is the sight of a pretty girl dressed in a hot pink leather minidress and thigh high boots that is holding their attention. The men are glancing at me with thinly concealed desire, while the women are staring and making what I imagine must be snide comments about my outfit.

Tom leads me into a beauty parlor to have my nails done. I worry briefly about getting the nail polish off later, but I am too caught up in this whole adventure to refuse. The woman who works on my nails is a gorgeous young Asian-American girl who talks the whole time she is working. She comments on my pretty outfit and I thank her for the compliment. Once I have started, my soft feminine girls voice is easy to maintain and feels like a natural part of me. I do my best to mimic feminine gestures like tossing my hair, etc. The strange thing is that I find myself really attracted to this girl. At one point I realize that I have started to flirt with her and I quickly back off a bit. She paints my nails a pretty shade of pink, which matches my dress and my lip gloss.

When I'm all done, Tom whispers to me that there is money in the purse and opening it, I am shocked to find several hundred dollar bills. After paying the girl, Tom leads me off to Frederick's of Hollywood to buy lingerie.

As I walk into the store, I am overwhelmed by all of the sexy and pretty lingerie. When we come to a display of corsets, I hold one up that is identical to the one I am wearing under my dress against me and say to Tom, "Now I know where you do your shopping."

"You can buy anything you want Jessica. In fact, I don't want you to leave this store without at least a dozen complete ensembles. I want you to buy bra's, garter belts, stockings, more corsets and nightgowns," he says with a smile. "I also want you to buy a few more pairs of boots."

What a dream come true! A few hours ago, I wouldn't have given a thought to these sexy feminine clothes, other than to wish to see a girl in them. But now, I am holding up sexy bra's, corsets, etc. and imagining what they will feel like on my body! At Tom's urging, I take my selections to the back and with the salesgirls permission Tom enters the changing room with me while I model one sexy item after another for him!

It is such a sexy turn on to slip into feminine negligees, bras and other lingerie in front of my lover. He tells me how sexy I look in each outfit. After choosing a lovely collection of lingerie, I try on some ultra sexy boots and choose 3 pairs in different colors. The bill for it all is enormous, but Tom doesn't seem to mind paying it and I have the exciting sense that he expects me to be a part of his life for awhile...

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bygirlboybootsie© 9 comments/ 281161 views/ 26 favorites

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