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."
