tagFetishTransformed Into A Shemale

Transformed Into A Shemale

bygirlboybootsie©

I was 18 when I first had sex with a man. This is the story....

I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have been dressing up as a sexy girl ever since I was 18 years old and had my first experience with a man. The following is how it all started...

The summer of my 18th year was beautiful and warm. I remember the wild high school parties outside on warm summer nights. I wore my sun-bleached hair long at the time and I was just beginning to develop confidence in my looks. At the time, I was going out with a beautiful French girl and we were having a lot of fun getting high and having really great sex almost every day.

Before the fateful day when I first met Tom, I had never had a sexual encounter with a man, but I can't say that I hadn't sometimes wondered about it. My best friend at the time, John was a beautiful blond hunk who was going out with a sexy girl named Nancy. One day I spent the night after a party at his house. Getting up to take a leak, I heard the unmistakable sound of hot sex coming from his room. My cock became almost instantly hard and throbbing as I heard John crying out, "Ooh, suck me Nancy, you sexy bitch! Wrap those sexy lips around my cock and suck me!"

I stood there, fondling my cock and wishing that I could watch (or better yet join in), when I suddenly realized that John's window would be clearly visible from the roof. Quietly retracing my steps, I went back to my room and slipped out onto the roof and crawled to a spot outside where I could clearly see the action going on in John's room...

I sat transfixed by the site of my hunky friend John, standing half naked with his strong muscular chest with it's pointed sexy nipples clearly outlined and his giant cock (I had never seen it erect) bursting forth from a pair of ultra sexy and tight black leather pants that I had never seen him wear. Sexy blond Nancy was kneeling before him, her sexy and glossy lips encasing the head of his throbbing cock and his hands entwined in her long blond hair as he forced his throbbing cock deeper into her mouth.


My own cock is now dripping pre-cum and I am fondling its wet glistening head and breathing deeply at the site in front of me. Nancy, who I had always secretly wanted to fuck, was wearing a sexy black satin garter belt and sheer stockings, along with matching black silk panties and bra. I always loved to see pictures of girls in porno magazines dressed in sexy lingerie, but this was the first girl I knew, that I had seen dressed like this, and it was incredibly exciting!

John was treating Nancy pretty roughly, pulling her head forward until she was almost gagging, and then pushing it back in a rapid motion. "You love it, don't you? You sexy bitch! You love having my cock between those sweet lips! I'm not going to let you drink my cum now though. I'm going to fuck that tight ass of yours. Get up on the bed and I'm going to fuck you doggie style"! He cried.

I was almost to the point of cumming as I stroked my own cock, but I forced myself to stop as I watched Nancy, her smooth sexy body encased in that lovely lingerie, crawl up on the bed and raise her tight panty clad buns in the air. John then roughly pulled her panties down to reveal her sweet soft buns and gripping her ass cheeks, he spread them wide to reveal her tender anus which he began forcing open with the giant tip of his throbbing cock. I could hear Nancy moaning in pain and excitement as John slowly forced the entire length of his cock into her tight ass and then began sliding it in and out in rapid strokes as they both moaned in excitement.

Kneeling there on the roof, my own throbbing cock in my hand, I longed to be in there with John and Nancy. The sight of John's huge cock protruding from those sexy leather pants sliding out of Nancy's buns made me feel more turned on than ever before. All of a sudden I realized that although the site of sexy Nancy all dressed up in lingerie was really exciting, it wasn't so much the thought of fucking her that was turning me on, rather it was the idea of being in her place and having John's gorgeous cock up my ass, or between my lips that really was getting me hot!

After that night, I began to look at John, and some other guys in a new light. I found my gaze lingering on hard masculine bodies with their tight buns and hidden but powerful cocks. I began to dream about being fucked by guys and I was constantly fantasizing about what it would be like... At the same time, I realized that I was far too uncertain to ever initiate such an encounter. Most of my male friends told jokes about gays and the thought that I might be gay never fully entered my mind despite the fact that now every time I was in the gym shower with John, I had to constantly fight the erections I developed by being next to his beautiful naked body. I still enjoyed sex with my French girlfriend Nicole, but in the midst of sex with her, I often fantasized that it was John's mouth into which I was slipping my tongue...

One weekend, I went into NY to a gay theater. It was such a turn on! On the screen a beautiful blond hunk was fucked and dominated by a leather-clad hunk and all the time I wished that it was me with that beautiful cock up my ass and between my lips! As soon as I realised that almost all the guys in the theater were either jerking off, or sucking each others cocks, I released my own cock and stroked it openly as I was captivated by the action on the screen. I hoped (and feared) that some young hunk would approach me, but the best thing that happened was that a couple settled down in the row in front of me and started making out and eventually blowing each other. I wanted so much to join in! Anyway, by the time I left the theater I was sure that I wanted to be with a man, and soon!

Fortunately, I didn't need to exist long in this terrible sense of uncertainty. About 3 weeks after that night at John's, I decided to hitchhike down to the shore. It was late morning and I was standing on the side of the road with my thumb out, dressed in a tight pair of faded denim cutoff jeans, which revealed my long and muscular legs and hard virgin buns, a pair of sandals, and a white tee shirt. I had a knapsack over my shoulder and I was in the midst of another daydream about John, in which I was kneeling in front of him the way I had seen Nancy, and he was forcing his cock between my eager lips...when suddenly a pick up truck pulled up right in front of me. Throwing my pack into the back, I jumped in.

Looking the driver over, I was thrown into a sudden sensation of confusion, and I felt my face begin to flush. He was dressed just like some of the gay hunks in some of the leather magazines I had purchased. But unlike many of those studs, this guy could not have been more than 21. He was beautiful! Dark short hair framed a handsome tanned face with green eyes and full sensuous lips. His powerful lean body was encased all over in tight sexy black leather! From tight black leather pants and sexy leatherman boots, to a sexy black leather vest and a spiked leather choker!

"Hi, thanks for the ride," I say nervously, as my eyes feast on his lovely leather clad body. "My name is Jessie" (I always give fake names when I hitchhike, and I've always liked that name).

"Hi Jessie, my name is Tom. I'm happy to have the company and you look like you were getting hot out there," he says and I notice his eyes roaming down my body and with a shock, I notice that they linger on my cock (or is it my imagination?), outlined against my tight shorts that is still hard from my daydreams about John, and now my proximity to this handsome leather clad hunk. "Where are you going Jessie?"

"I'm going down to Long Beach Island. How far are you going?," I ask.

"I can take you part of the way there," he replies. "What are you going to do down at the shore"? He asks with a smile.

"I'm going to visit my girlfriend," I reply nervously, afraid that somehow this will typecast me as "straight," when I am already lusting after this gorgeous leather hunks body!

"I bet she's a beauty. A hot looking boy like you must have lot's of girls after you," he says with another quick glance at me as he drives. Somehow he seems once more to take not only my face, but also the rest of my body in his glance.

I can't seem to reply to the compliment, but I can feel myself blushing and my cock squirms within the tight confines of my shorts at the thought that he finds me attractive.

"What does she look like," Tom asks.

I find this line of questioning a little strange, so soon after we've met, but I feel there is a strong sexual undercurrent to the questions and coming from him, I don't mind! "She's French. Her name is Monique and she is my age, dark haired about 5'5" she is very beautiful," I reply.

"Oh, French girls are beautiful. You're lucky. I'll bet she loves to wear lingerie?"

"No, I wish," I reply.

"How about leather? Don't you love the sight of a girl dressed in a leather miniskirt, or boots? Does Monique like to dress in leather?," he asks.

Tom's free hand absently rubs the tight leather covering his thigh as he is talking about girl's dressed in leather and the sight causes my cock to throb even harder against the tight denim of my shorts and I catch myself squirming a little as I stammer my reply in a nervous voice, "I do love leather...Uh, I mean, I love the sight of girls in leather, but Monique doesn't ever wear any...

"Ah, that's too bad. How about you then, do you like to wear leather yourself?" This time I am almost sure as his glance lingers on me that he is staring directly at my cock which is clearly outlined through the tight denim. I squirm again as I reply, "I've never tried it, but it looks pretty comfortable." I dart a glance at him when I think he's not looking and am thrilled (and a little scared) to see the enormous bulge of his cock now pressing against the tight black leather of his pants!

"Well, you can tell that I love leather. You should really try it sometime. It doesn't just feel comfortable, it makes you feel really sexy.," Tom says and rests his hand casually over the bulge of his cock. "Hey," Tom exclaims, "Do you want to pull over here at the park and smoke a joint?"

He is already making the turnoff, as I reply, "Yeah, that sounds great."

I have to make a conscious effort to stop squirming in my seat at the thought that Tom is about to try to seduce me. The thought of running my hands over the sexy leather of Tom'' hard and sexy body is such an incredible turn on that I make up my mind to respond to any opening that Tom gives me.

Pulling into the park entrance, Tom heads for a trailhead opening and drives his truck for some distance deep into the woods. He obviously wants us to have some privacy! Finally, he pulls over in a beautiful open glade, deep in the park. He then takes a joint from his pocket and lighting it, he takes a deep toke and then passes it to me.

We pass the joint back and forth a couple of times and then Tom puts it out. "This is really good herb and I wouldn't want to get a boy like you too high," Tom says with a laugh.

I feel very relaxed and sexy now from the herb, and I lean against the door with my body turned toward Tom. He has done the same thing and my eyes feast openly on his gorgeous body, and zero in on his clearly outlined cock which looks like it is going to burst from the tight confines of his sexy leather pants.

Tom follows the direction of my stare and he smiles and very obviously casts his gaze slowly from my face down across my body until it rests on my own cock, which is also clearly outlined against my tight denim shorts. He then slowly lays his hand against his taut leather clad cock and begins to slowly fondle it right in front of me!

I feel my face blushing as I squirm in my seat, but I can't take my eyes away from Tom. He has closed his eyes, but the smile remains on his face as he continues to fondle what is clearly an enormous throbbing cock. I'm sure that he knows that I am watching him because he then says, "Getting high always makes me feel so horny. Especially when I've got my leather on." Opening his eyes slightly he looks again at my hard cock and adds, "It looks like getting high makes you horny too. Go ahead and do what feels good Jessie. I can see you want to..."

I need no further urging, so under his lustful gaze I move my hand down to my almost painfully throbbing cock and closing my eyes, I begin to fondle it. Knowing that Tom is probably watching me makes me squirm in my seat.

Suddenly, I hear the sound of a zipper slowly opening and my eyes fly open to the sight of Tom slowly, teasingly sliding his zipper down. I lick my lips in lustful anticipation and am suddenly shocked to note that Tom is staring right at me, obviously loving my reaction. I openly turn my gaze back down to the sight of Tom's cock covered by a tight red leather thong jutting forth from his now fully opened zipper.

"You like to watch me, don't you Jessie"? Tom asks, smiling wickedly.

I can only nod in reply as he wraps his hand around the leather-clad shaft of what must be the biggest cock I have ever seen! I guess that it must be at least 10" long, and very thick.

I find myself panting and fondling my own aching cock through my shorts as Tom teasingly slides his hand up and down the leather clad outline of his lovely cock.

Tom must already know that it is safe to do it, as he slides across the seat toward me and taking my hand from my own cock, he gently places it upon his throbbing leather clad cock. It is warm too the touch and I am thrilled by the throbbing feeling coming from his incredibly stiff cock. "I know you've been wanting to do this... "Go ahead Jessie, run your hot hand all over my cock."

I eagerly comply and wanting to be closer to it, I lean down until my face is inches above it and I can smell the sweet leather as I begin fondling it with both hands eagerly. "You've never been with a guy before, have you?," Tom asks with a smile. "Are you sure you want this"? he asks, reaching down and gripping my own cock which leaps at his touch.

"Ooh yes!" I gasp and since I can't wait any longer, I lean over and pressing my lips against the throbbing leather clad tip of his cock, I open them and begin to lick and suck it, savoring the sweet leather taste and smell.

"Oh, Jessie, yes! That feels so good you sexy boy! You love leather don't you?" Tom cries as his tight ass squirms against the seat and he pushes his crotch upward against my eager lips.

Raising my head for a moment I look him lustfully in the eyes and respond, "Ever since you picked me up and I saw you dressed in this sexy leather outfit, I have wanted to get my hands on you. It feels sooo good, Tom." Lowering my head I again let his leather covered cock head slip between my lips and I allow my hands now to roam over his hard and sexy leather covered legs and up to his muscular broad chest. Then, without waiting for permission, I slip my fingers behind the leather waist band of his thong and slip it down to reveal his beautiful throbbing cock. Its tip is oozing pre-cum and I notice that he has a sexy black leather studded cock ring circling the base of his cock.

Ever since that night when I watched Nancy suck John, I have been waiting for the chance to have a mans cock between my lips....so, I don't hesitate as I spread my lips to accept the enormous head of Tom's cock into my eager mouth. I love the salty slippery consistency/taste of his pre-cum. Tom moans in ecstasy as I swirl my tongue around the tip of his cock.

"Oooh yes, Jessie! That feels so good you sexy little boy! Suck me lover!" he cries. He grips the sides of my head firmly and tries to push my head down to engulf more of his monster cock, but after a few inches, I start to gag and have to pull away for a moment.

"I'm sorry," I gasp. "I can't take it all in. It's so big!"

"But I can tell you love it, don't you? You love having a mans cock between those sexy lips. Don't worry, just try to relax your throat and gradually take more in."

With that advice I eagerly slip his lovely cock once more between my lips and begin to suck, lick and nibble it with enthusiasm. I feel so turned on and sexy sucking this sexy mans cock! My own cock is rock hard against the tight denim of my shorts. My ass is squirming so much in excitement that it is continually rubbing against its confines. When Tom suddenly reaches down and begins fondling my tight buns, I almost begin to cum, it is so exciting.

Thinking back on it after many years of sucking cocks, I realize that I wasn't very good at first, but I think that Tom was so turned on by having this sexy young virgin boy sucking him that it wasn't long before he began to moan and cry out and then hot sweet gobs of cum began to spurt into my mouth, which I eagerly swallowed.

As Tom's sweet cock began to soften in my mouth, I lovingly licked and sucked the last drops from it and then slipped it back into the sexy leather thong and looking up as I caressed it through the soft leather I notice a satisfied smile on Tom's face. "You are some eager young cocksucker Jessie! That was wonderful! Come sit up next to me.," he says, patting the seat beside him.

As I settle myself next to him I look down at my still achingly hard cock and notice that there is a big wet spot where my pre-cum has soaked through the tight denim. Leaning toward me, Tom places one hand over my throbbing cock and begins to fondle it, and he places the other one behind my head and pulls my face to his... As our lips meet, I am overcome by the sensation of his sexy full lips against mine, the smell of his masculine cologne, the pressure of his powerful chest against mine, the feel of his strong hand against my cock.... His sweet tongue forces itself into my mouth and our kiss becomes passionate, our tongues swirling against each other... Tom then wraps both of his powerful arms around me and lifts me until I am sitting on his lap with my legs to either side. We continue passionately kissing with brief intervals as I suckle on his strong neck and ears. I begin to feel his cock growing again beneath me. It is pressing right between my buns and I eagerly squirm against the sexy leather bulge of it.

Tom pulls his head back for a moment while fondling my tight buns with both hands as his leather covered cock slides tantalizingly against them. "Hey, how would you like to go to my place, which is nearby? I'd love to get you into my bed, and I have a few things there that might interest you..."

Reaching down to fondle his cock I lick and suckle on his ear I whisper, "as long as this is one of the things you want to show me," I say with a gentle squeeze, I would love to"!

Sliding off of his lap, I return to my seat, but I continue to fondle his sweet cock through the leather thong and his opened zipper as we drive out of the park. My mind is swirling with the sensations I have experienced within the past hour and my imagination is running wild with anticipation of what awaits me at his house. I can't wait to run my hands over his bare chest and shoulders, and my anus is still tingling with the sensation of having his cock press against it. I hope that he will soon offer to slip it all the way in and fuck me the way that I watched John fucking Nancy!

It takes no more than a few minutes before we arrive at his apartment. I feel kind of shy when Tom takes my hand as we leave the truck. We pass a few people as we head up to his apartment and I can just imagine what they must be thinking at the sight of a leatherman like Tom leading a teenage boy like me by the hand to his apartment. My cock remains achingly hard through it all and I am unable to shield the view of it (and the wet stain in the front of my shorts!) from the people we pass. But all thoughts of embarrassment leave my mind as we enter his beautiful apartment and he takes me into his strong arms and presses me against the wall and our lips find each other in a deep kiss...

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bygirlboybootsie© 9 comments/ 274294 views/ 25 favorites

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