Halloween Transformation Ch. 1

Last Halloween marked a major change in my life and identity. It is amazing how much changed for me on that one day. And it was all a complete surprise!

I had been seeing this really foxy girl named Barbie for a few weeks, and I was looking forward to going to the Erotic Ball with her, dressed up as slut and a dominant S/M stud with our gender roles reversed. I had never been to this ball, but it sounded like a real turn on. Although I wasn't especially turned on by the thought of being dressed up like a slut, the thought of my girlfriend dressed all in black leather as a guy turned me on for some reason, although I didn't tell her that. I found myself fantasizing about having her order me around at the ball and having her act the dominant one in our relationship.

The morning of Halloween we went out to do our shopping. My cock was rock hard from the moment she stepped out of the dressing room at Wilson's dressed in a pair of tight leather pants and a leather vest with her hair hidden by a leather baseball cap. Then she chose a sexy short pink leather minidress for me... I was so shy at first when she held it up to me in the store and began talking about how sexy I would look dressed in it, but when I slipped it on in the dressing room, I was surprised at how my cock became so hard when it came in contact with the smooth leather, that it was clearly outlined against the tight leather of the dress and I couldn't go out to show it to her. I thought it was just the feel of the leather that was getting me so excited, but when my girlfriend entered the booth and saw me, she teased me "you obviously like wearing a dress, maybe we should do this more often." Mortified, I assured her that it was only the feeling of the leather, etc. She gave me a disbelieving look as she fondled my achingly hard cock through the smooth leather. "Just wait until we dress you up in the rest of your outfit. We'll see then..."

My girlfriend continued to torment me by telling the saleswoman as she rang us up, that the dress was for me, and that I had really enjoyed trying it on! My face was blushing furiously as we left.

We then went to Frederick's of Hollywood, where Jennifer picked out a sexy pink satin corset with white frilly lace and matching pink silk panties. She also chose some lovely matching white French back seamed stockings, and some silicone "boobs" to insert into the corset. In response to my pointing out that I didn't need to wear these under my dress, she replied that we were going to go "all the way" in transforming me for the evening into a sexy girl. "Who knows, she said, maybe you'll like it so much you'll want to continue dressing up"!

When she sent me into the dressing room, I found myself, inexplicably, eager to slip into the sexy lingerie. She slipped in a moment later to help me cinch it tightly in the back, and again she found me with my cock rock hard, this time within the sexy tight confines of my silk panties. I couldn't believe the incredible excitement I was feeling at being cinched into this sexy and feminine corset and admiring the sight in the mirror. With the boobs inserted, athletic and masculine figure, which I had always been so proud of, was transformed into a voluptuous feminine one. "Watch out, she whispered, you're starting to get your panties wet and it might be a little embarrassing when we check them out...." Sure enough, there was a little spot of pre-cum on the tip of my panties where my cock was straining for release. I quickly (but reluctantly) slipped out of them. At the check out counter, my girlfriend again told the saleswoman (a real sexy fox) that the lingerie was for me. The saleswoman looked me over and remarked that she was sure I would look really sexy dressed up as a girl. "I'd love to see you when you're all dressed up, why don't you come by and show me sometime"?, she asked with a smile. I was too embarrassed to answer, although I did feel a thrill at the thought of flirting with this sexy woman while dressed as a girl! My girlfriend then surprises me by asking if its ok for me to put on the lingerie in the dressing room, as we are about to go shopping for boots "and he'll need to have stockings on for that." The foxy saleswoman, who introduces herself as Jessica, answers that it would be no problem. She then offers to help cinching my corset, "so I can show you the proper technique," she says with a smile, and a wink at me.

I am speechless at this point and my mind is full of conflicting emotions. I'm excited at the thought of slipping into the sexy corset again, and being close to sexy Jessica, but at the same time I am mortified and embarrassed that I am even having these thoughts! Before today my self image would never have allowed me to imagine myself dressing up in girls clothes, but I find myself incredibly turned on now at the sensuous and feminine feeling of the silk, satin and leather!

As we slip into the booth, Barbie turns to me with a wicked smile, and whispers in my ear, Jessica seems to be turned on at the thought of you dressed up as girl! I can't believe she is saying this without even a trace of jealousy! She then orders me to strip, and sure enough, my cock springs forth, totally hard at the sight of my sexy outfit laid out for me! It is such an incredible feeling having Barbie slide my tight silk panties up my legs and smooth them over my tight buns. She then helps me slip again into the ultra sexy pink satin corset, and at that point, Barbie calls for Jessica to join us. I try to get her to stop, because my cock is totally jutting forth against the confines of my panties, but it's too late, and I turn my back to the door as sexy Jessica comes in.

"You've made a great choice. This is the sexiest corset we have, and it really laces up beautifully to create a very feminine figure. Placing her knee into the small of my back, she tells me to inhale and pull my waist in as much as possible, she then pulls the laces of the corset with great force making my waist smaller and smaller before tying it off. She then tells Barbie to slip the inserts in. The corset is now so tight, I can barely breathe. I stand there, still turned away from Jessica, because I don't want her to see my hard cock, which I can feel has now oozed pre-cum through the front of my shiny silk panties again. But Barbie forces the issue by saying, "turn around Jamie, we want to see how you look." I would have refused her, but she takes my shoulders and turns me around to face Jessica, who immediately focuses on my erection.

"Oh my, you feel sexy dressed in a corset, don't you?"

She holds my eyes waiting for a response, so I stammer, "yes, I guess I do feel kind of sexy. I've never been dressed like this before. Barbie and I are going to a Halloween parts... At this point Barbie cuts me off, "Jessica, I think Jamie is responding so well to being dressed as a girl, that I may dress him up very day, not just on Halloween. Don't you think he'll look hot with some makeup and this dress on," she asks, holding up the sexy leather minidress we just bought.

"Oh, yeah, I think he'll make a really pretty girl." I've got a full makeup kit right here, why don't we get started right now?"

Barbie overrules my protests and has me sit on a chair as she and Jessica roll my new stockings on and attach them to the garters. Ooohhh, the feeling of the smooth silky stockings being rolled up my long and muscular legs is exquisite, as is the gentle tugging I feel as the garter straps are attached. I find myself squirming in my seat with excitement and my cock is bobbing and jerking within my sexy panties.

Jessica then goes out and returns with a large mirror and a full makeup kit. They set the mirror in front of me so that I can watch my transformation, which begins with a light shave to remove any facial hair. The two girls, who are now chatting and giggling like best friends, and totally amused at my discomfort and domination, then comb my long blond hair and pull it back with pink berets. They then apply glossy pink lip gloss to my lips, and mascara and eyeliner, as well as a little blush and foundation. I watch in amazement and as they put the finishing touches on and looking in the mirror, I no longer recognize myself. Instead, I see a beautiful blond girl, and as far as I can tell, I am no longer recognizable as a boy! Even my body is transformed, and it is only the bulge of my hard cock straining against my panties and perhaps the muscles of my arms and shoulders that reveals that I am really a guy.

"Oh my god, I can't believe what you two have done," I say. "I can't even recognize myself."

"You look gorgeous. Like a really hot girl. When you go out in this dress, all of the guys are going to hit on you. You're going to have to practice speaking like a girl and moving and acting like one too. We're also going to have to change your name. What would you like us to call you," Barbie asks as she presses her sweet body against me from behind, her hands caressing my smooth corset cinched waist.

My mind is spinning, but at this point I feel like resistance is futile, and besides, I've never felt so sexy and alive before! Only Jessica's presence (also a turn on!) keeps me from turning around and telling Barbie I want her, right here, right now!

"How about Jennifer," I say in what I hope sounds like a girls voice.

"Perfect! And your voice is perfect too! OK, Jennifer it is!" Barbie exclaims with excitement.

Jessica and Barbie then help me slide on my sweet leather minidress, which hugs my new curves as if it had been molded for me! As I stand in front of the mirror in this ultra sexy pink leather minidress with my legs encased in these sexy long stockings, I find myself posing and running my hands over my leather clad sides, even over my "boobs" which look so real jutting against the tight confines of my corset and dress!

"Hey, would you two mind if I came along to the party?." It sounds like fun, and I would love to see how everyone reacts to Jennifer." Jessica asks, smiling at me with a flirtatious look on her face.

Barbie responds, "I'd love it if you'd come. I'm going to be dressing as a guy though, so watch out!" she says teasingly. Jessica responds by meeting Barbie's eyes directly and saying, "that's ok, I like being with girls, which is one of the reasons its been so much fun dressing up Jennifer. You should know though, that my boyfriend will have to come with us. We already had plans for Halloween and I can't ditch him at this point. But don't worry, he's a lot of fun and is very open-minded about my interests."

I follow their conversation with amazement. I sense now that Barbie must have bisexual interests, but the thought of being with them both is a total turn on, especially acting as a girl. The only thing I'm worried about is Jessica's boyfriend and what he may think of me and how he might get in the way of my fantasy of being with Jessica and Barbie in bed at the same time, with Barbie dominating me!

We leave Jessica with plans to meet at Barbie's house in the early evening. As we emerge into the mall, with me dressed up in this super sexy and feminine "fuck me" outfit, I am very self conscious and take Barbie's arm for comfort. I am acutely aware of the attention I'm attracting, and I do my best to stifle my embarrassment and walk like a girl, with a sway to my hips. I keep reminding myself that no one can tell that I'm really a guy and I begin to realize that guys in particular are staring at me as we pass, their eyes roaming my body with interest. A thrill of excitement passes through me at the thought that they find me attractive, and then I find myself shocked that the thought is exciting. Am I gay, or bisexual, I wonder? My whole world orientation seems to be changing today! Against my will, I find my cock beginning to lengthen and to my embarrassment, a glance down shows that it is clearly outlined and beginning to jut against the front of my dress!

I pull Barbie aside and whisper that my hard on is showing and ask what I should do. Barbie just laughs and stepping away, she pulls me by the hand and says, "You shouldn't be ashamed. If it weren't for that, no one would know that you're not a beautiful girl. In fact, what turns me on is the fact that your cock is showing that you're turned on by acting like a sexy girl! It adds to your sexiness for me, and I'm sure for many women, and even many men!"

Our little scene has attracted even more attention, so I try to pull myself together, and walk as naturally as possible, with my face blushing furiously, because I am afraid that everyone is looking at my cock, which remains rock hard and clearly outlined against the front of my dress!

Barbie leads me to a women's shoe store, where they have a big selection of sexy boots. She picks out a pair of pink leather, thigh high boots with high heels which perfectly match my dress! "Aren't these perfect? They complete your outfit perfectly! You're going to look like a total sexpot once you have these boots on!" she whispers in my ear.

As Barbie is showing me the boots, a young salesman comes up and asks if he can help fit me. Barbie responds for me, as I am tongue tied with embarrassment. The salesman asks me what size I am, as he kneels down to take off my shoes. I answer with my male size without thinking. He looks up in astonishment, but as he is almost directly at my waist level, my cock, which is still aching with excitement, especially at the prospect of slipping into these ultra sexy boots, is almost directly in his face! He gives me what seems like a knowing smile, and then says that we had better measure.

He slips off my shoes, and then, with his hand on my stocking encased calf, he guides my foot onto a measure. The feeling of his warm strong hand on my leg sends a thrill of excitement through me, so that an involuntary moan escapes me for a moment, and my cock begins to throb with excitement! I feel like dying with embarrassment, as I am sure that John will notice the movment of my cock through the tight leather of my dress. What will he think. And why am I getting turned on at the touch of a mans hand?

Looking down at John, I am struck suddenly by how attractive he is. He's blond, blue eyed and tan with an athletic body. He's wearing tight black leather pants, and a tight t-shirt, which hugs his muscular chest and arms. I am caught up in looking at him, as he looks up and meets my gaze, that knowing smile still on his face. His stand still clasps my calf, as he tells me that I'm a size 11 and asks if I'm ready to try on a pair. Without thinking, I smile at him and respond that I would, and that he I appreciate his help. As he heads off to get them for me, my eyes linger on his tight leather clad buns.

Suddenly Barbie, whom I had forgotten, takes my arm and smiling, whispers in my ear, "Well, it's obvious that this hunky salesman has the hots for you! And it looks to me as if you're loving it, aren't you!"

Barbie doesn't seem to be mad, or jealous. In fact, she seems to be excited at the thought that I am enjoying the attention of the handsome salesman. So I respond, "I've never thought of being with a guy before, but I have to admit that being dressed up like this, I really feel feminine and sexy, and I think it is making me respond like a woman. He is handsome, isn't he?"

"Oh yeah, he's a hunk. And Jennifer, just so you know, I don't mind if you flirt with guys, or girls." She tells me that she's going to wander elsewhere in the store, so that she doesn't cramp my style.

Barbie's calling me Jennifer, stuns me almost as much as her telling me its ok to flirt with a man! My head is so filled with conflicting emotions and desires, that I hardly know what to think, but as I see John returning with the sexy boots, I find myself instinctively smoothing the sides of my dress, and then my hair.

John motions me to sit, and as I do so, I am shocked to find that the hem of my dress barely covers my panties! Mortified, I quickly try again, smoothing my dress as low as possible, but my bare thigh and the straps of my garter belt are still clearly visible! Also, I am embarrassed as I note that my leg hair, which hasn't been shaved, is visible on both my upper leg, and a little through my stockings.

As John unwraps the boots, he seems to be flirting with me as he points out that these boots will match my beautiful dress perfectly, and that I have such great long legs, that the boots should look great on me. He asks me my name, and it feels strange, but exciting to tell him my name is "Jennifer." His beautiful blue eyes seem to caress, and undress me as he speaks with me, and I have to fight the urge to squirm in excitement. Its clear now that he's flirting with me, and I respond, letting my own eyes, obviously, appreciate his gorgeous maleness.

As John kneels between my legs, my cock has now formed what looks like a tentpole in the front of my dress. As John unzips the first boot, he again grabs my stocking clad calf, and this time he gives it a squeeze, as he slides it into the sweet smooth leather of the boot. He does the same with the other boot, and then, looking directly at my jutting cock, he says, "I guess they feel pretty sexy." Why don't you try walking in them?"

As I stand on high heels for the first time, I find myself momentarily unbalanced and I would have fallen forward, if John had not stepped forward to catch me. I only get to enjoy the feeling for a moment, but for that moment, I have my hands gripping his strong shoulders, and my boobs, pressing against his hard chest, and I feel for just a moment, my hard leather encased cock, pressing against his leather pants. I can smell his masculine scent and I long to remain in his arms, and in fact, I do linger for a moment longer than necessary.

Flustered, I reluctantly straighten and John releases me. "I guess you need to do some practicing. Here, you can lean on me." With that, he puts his arm around my waist, which is now so slim from the corset. I walk carefully, and lean against him a bit, because I love the feel of his strong body. I catch sight of Barbie, who gives me a wink and a smile, which I return.

"Oh John, you are so sweet. If you hadn't caught me, I would have fallen.," I gush.

"It was my pleasure. It's not everyday that a beautiful girl like you falls into my arms. Hey, do you already have plans tonight?" he asks.

Oh my god! This handsome hunk is asking me out! And he knows that I'm really a guy! That means he definitely wants me! I am attracted to him. I love the feel of his strong arm around me, Barbie has said she doesn't mind if I flirt with him, does that mean she doesn't mind if I go to bed with him?... All of these thoughts swirl through my head as I gaze back at his beautiful face.

Taking a deep breath, I say, "actually I do have plans with Barbie, the girl I walked in with, and another girl, to go to a masquerade party, but you're welcome to join us. In fact, I'd really love it if you'd come," I respond with a smile and a fondle of his hard shoulder.

"That sounds great. What should I wear?" he asks.

"I love leather. Anything in leather would look great on you. You choose.," I respond letting my eyes lower to his crotch, which to my excitement now reveals his hard on, clearly outlined against the tight leather of his pants! I wish I could reach out and fondle it!

I give John directions to Barbie's house that evening, and then I introduce him to Barbie, who seconds his welcome. We leave the store with me still wearing the boots, as I need to learn to be comfortable in them. Walking through the mall, my high heels tapping on the marble, I soon become comfortable in them, and I love the feel of them encasing my long stocking clad legs, and the way they force me to walk with a really feminine sway to my buns.