A few Halloweens ago I decided to dress up as a woman and it turned out to be one of the greatest things I ever did. I came up with the idea a few weeks before the holiday and decided (as usual) to make sure and be as convincing as possible. With my girlfriends help I ordered a corset, high heels, a garter belt with thigh high stockings, a little black mini dress and a nice curly brown wig (I was going for a slightly loose/whorish look). When they arrived a few days later I felt a little apprehensive about actually going out in public wearing women's clothing. My girlfriend helped me do a dry run and then with a little encouragement from her mouth managed to get rid of any doubts about it ;)
Finally the day arrived and she shoved me into the shower with a bottle of Nair with orders to cover my skin from chest to toes. Once it was rubbed in a bit it started to tingle and a quick 15 minutes later I watched all my body hair rinse away. Stepping out of the shower she gave me a careful check for stray hairs. Once out of the shower she had me shave my face twice (luckily it wasn't too necessary since I have fairly light amounts of facial hair). Once that was done she patted me down with the towel and then applied some of her Victoria's Secret body powder.
Once dry she helped me into a pair of panties and the garter belt. Next she had me slip the corset on. The corset which in addition to being quite expensive (like I said I like to commit fully to a costume) also was a dark purple satin color with a full bodice covering. Once it was tight I found myself admiring the women who wear these all the time, I could barely breath right in it. Stepping into the closet for a moment my girlfriend came out with a little gift for me. She was holding a pair of DD breast forms. She said she wanted to make sure I had the total package look. Loosening the top laces she applied a sticky patch to the forms and then slipped them into the cups that were built into the corset. Amazingly once the corset was re-laced it looked like my new breasts were natural. They felt warm and almost unnoticeable to me within minutes.
Next she had me slip on the mini dress and then put a towel over my shoulders to do my makeup. As I was bending down to pull the dress up I was amazed at how the breast forms moved and jiggled a little bit. It was like having real breasts and the sight of the jiggling through the corset cups made me a little bit hard. For the second time in women's clothes my wonderful girlfriend helped get rid of the apprehension and also the erection building in my French cut panties. Once she'd taken care of that she told me to behave like a lady (while smiling a "wait till after that party" smile). Sitting down at the makeup table she had me close my eyes as she went to work. I felt her prodding and brushing at my face for what seemed like an hour before she had me open my eyes and then she added some touches to my eyes and my eyelashes. She turned me back towards the mirror and I gasped a little at what she had done. My normal slightly nerdy face looked completely transformed, where before had been the face of a average looking man had turned into a sultry, sexy vamp. She'd given me more feminine cheeks and managed to hide my eyebrows and draw in nicely curved brows. My eyes had a nice smoky shading highlighting my eyes and drawing out brightness I'd never noticed I had. She'd managed to put an element of fullness to my lips that made them as she put it "cocksucking lips" (if only she knew I'd find that out later). Frankly I was surprised at how well I looked. I wouldn't say I was hot but I thought I looked fairly cute..even pretty.
Removing the towel she pulled my hair back and pinned it down with some bobby pins. Grabbing the wig from the closet she quickly pinned it into place and then styled it with a little bit of hair gel. Within a few minutes I looked even more feminine and even more like a sexy woman on the prowl. She then told me to go and put on my stockings and showed me how to fasten the garter belt. Giving me a final adjustment (tucking my cock down between my thighs) and then straightening up my skirt she had me stand in front of the mirror to see how I looked. I had to wave at myself a few times because I just didn't feel completely sure I was looking at my own reflection. The corset gave me a nice hourglass shape (with the help of the breast forms) that was probably helped a bit also by my fairly girly thighs. The high heels and stockings made my ankles and calves seem longer and sleeker as well. I was feeling a bit shaky with how short my skirt was (3 or 4 inches above my knee) since it just barely covered the tops of my stockings. In fact when I bent down to adjust the strap on my heels the back of the stockings kept getting exposed. The soft curls of my wig curling down to midway on my back tickled a bit as I posed in front of the mirror looking at how everything fit me. I felt thrilled with how good this costume was going to look. Hopefully it went over as well as the previous year's Chewbacca costume. It was definitely much less warm of a costume.
My girlfriend then handed me a purse with a tube of lipstick, my cell phone and my wallet in it (although my license probably wouldn't be too much use with my current look). I slowly walked down the stairs trying to get used to wearing high heels. My girlfriend kept laughing as I asked her how to make my ass stop swaying so much. Once I made it downstairs I sat on the couch to wait for her to get ready. Once she was ready (her costume was a simple playboy bunny costume) she came downstairs and we made ready to leave. Getting outside and into the car was a very shocking experience since it seemed like every neighbor with children was walking in front of our house. Happily though they know how serious I am about Halloween. Finally we were in the car and on our way to the party. The party this year was at a local bar famous for it's hospitality during a party (of which it hosted many). About 5 minutes away from the bar my girlfriend's cell phone started ringing. Her work needed her to come in (she's a veterinarian and had a few borderline patients who were fading fast). I offered to have her just take me home but she insisted on dropping me off with the idea of joining back up with me shortly after she checked the two animals out.
Well we finally arrived at the front of the bar to see a short line leading into a very busy place. Getting out took a lot of strength and courage I didn't know I had. Showing the doorman my invitation I gave my girlfriend a quick hug and kiss. With a last "be back soon and good luck at the contest" my girlfriend headed back to the car. I was alone and entering the dim smoky bar my heartbeat was at least 90 million beats per minute. I sashayed my way (I still hadn't figured out a way to walk normally in heels) up to the contest registration and signed in.
Once registered, I headed to the bar and ordered a screwdriver. I lit a cigarette and slowly sipped the drink while checking out the other contestants. Quite a few good candidates other than me I thought as I finished the drink. Noticing how much less nervous I felt after that drink I ordered another. I giggled a bit when I thought this making me feel like I was trying to drink myself into a slightly easy and ditzy state. Right as I finished thinking this I felt a touch on my arm and turned to find a man dressed in surgical scrubs (with just the right touch of fake blood on the front) standing next to me. He complimented me on my costume and let me know that he had to get up fairly close to tell I wasn't a real woman. I felt myself blush at that and took a rather large swallow of my drink before answering thank you. Noticing that my 2nd drink was fairly empty he offered to buy another one since he was so impressed with how good I looked. I halfheartedly declined stating that it wasn't that unique of a costume and that he was just trying to get me drunk enough to take advantage of. We both laughed at the joke and then I said "who am I to turn down free drinks"!
He introduced himself as Mike and offered me a seat at his table. Looking around at how packed the place was and really feeling a bit unstable on those heels I said sure. I introduced myself as Gabby at which point Mike asked if it was short for Gabrielle or just meant that I talked a lot. I laughed and replied Gabrielle. Mike made a big show out of pulling out the chair for me. As I hung my purse on the back of the chair it fell. As I bent down to pick it up I felt my skirt slide up and then lost my balance. Luckily Mike was there and he managed to get an arm around my waist before I fell all the way down. As I stood up I felt his hand slide back and across my ass softly. I wasn't sure why but I felt myself blush slightly and smile a little flirtatiously as I said thank you and adjusted my skirt again. Finally I managed to sit down and cross my legs (as my girlfriend had reminded me at the makeup table earlier). Lighting another cigarette I asked Mike if he entered the contest. He told me "no I just like to see how well executed the costumes other people are". I told him how serious I was about costume contests and how I had won last year's competition. He apparently had been there since he recalled the Chewbacca costume as well. We talked for awhile about some of last year's contestants and who we thought had a chance that year. Noticing that my drink was empty I stood up to go to the bar and get another one. Standing quickly Mike offered to go and grab it for me since a lady shouldn't be expected to do things when a gentleman is present. I smiled and blushed a little more. Frankly I felt a bit odd being treated so well and also a little bit nervous about enjoying it so much.
He came back shortly with a drink for each of us and proposed a toast to Halloween and dedication to good costuming. I took a nice healthy drink and noticed that I was a bit lightheaded. I figured it was the vodka and the tightness of the corset doing the trick and stood up to get a bit of air. Standing with me Mike took my arm and guided me out to the balcony. You ok he asked? I told him I was lightheaded and he helped steady me as we stood looking out at all the people waiting to get in. After a few minutes and a bit more small talk I finished my drink and then went inside again. Mike followed and again pulled out my chair. I while flattered was a little bit unnerved by all of his attention. I asked if he thought I was a transvestite and looking for a boyfriend. He laughed and said "nope, just being a gentleman for the lady of the evening" and then explained he was just trying to help my character for the evening have more depth. This seemed to make sense to my slightly drunk self and so I smiled and said well then, why don't you ask me to dance. He laughed at that and then went to grab another drink for us both. When he came back I tried to hand him money for the drinks but he declined saying a lady should never have to buy a drink. I felt myself blush more and smiled sexily and asked if he was trying to flatter me since I obviously wasn't a lady. He winked and said I figured you were being a lady now and would show me the other side later. I snorted a bit when he said that but worryingly felt a slight stirring in my panties at the thought of "showing the other side".
After a few more minutes of talking Mike stood up and asked me to dance. I laughed at him and told him he was crazy. Grabbing my hand he pulled me up and led me to the dance floor. I felt quite a bit more dizzy and shaky then I did earlier and so stumbled a bit as we got to the dance floor. We started dancing (well I just kind of swayed back and forth in the heels) and eventually the song ended and a slow song started. Mike put his arms around my waist and asked if that made me uncomfortable. I told him it was fine and helped make my costume/look more authentic. I stepped in close to him and put my hands around his waist as well. We kept dancing like that for a few until I felt his hands slide down until he was cupping my ass and squeezing it slightly. I looked up with a look of shock on my face and he winked at me then leaned down and spoke into my ear "don't worry it's just for effect, all 3 judges are looking this way right now". I nodded and smiled then and tried to stay in character so I slid a little closer to him. We kept dancing that way until the song ended and a faster swing tune started. Stepping back from him I started trying to sway my hips and move a bit on the high heels. He spun me around and started swaying with me. I was starting to forget that I was dancing with a man I was having so much fun. He spun me around a few more times and then I finally lost my balance (damn heels) and slipped back against him. I felt my ass bump into him and then I felt what could only be his cock fairly hard (and a bit bigger than mine by the feel of it) shoving into my skirt. I regained my footing and turned around with a pissed off look on my face. He turned beet red and apologized to me explaining that he was having trouble remembering that I wasn't a real woman. I said fine but we're done dancing for now. The instant I said the "for now" I felt a bit of confusion about what was going on in my head and what was going on between us.
Sitting down at the table and taking a drink I suddenly recalled that it had been quite awhile since my girlfriend had left. I opened the purse and saw I had missed a call from her. I called her back and asked if she was ok. She told me that she had an emergency surgery to do and probably wouldn't be out of surgery until early tomorrow morning. She asked if I minded taking a cab home? I told her that would be fine, wished her luck with the surgery and then told her I loved her and would see her in the morning then hung up. Mike asked what was up and I filled him in on the details. He told me he'd happily give me a ride. I decided to tease him about his little bulge earlier so I put my hand on his knee and asked him "if he really thought I was that easy". He blushed and then winked. I finished my drink and realized I had to pee. I stood up to go to the bathroom and told him where I was going. He said that sounded like a great idea and we both left to go to the bathroom. The one downside to this bar is that there is a single bathroom with a urinal and a toilet with no divider since it's too small to fit a divider in. As I stood at the urinal Mike told me how odd it looked to see a beautiful woman standing to pee. I laughed and also thought to myself how good it felt to be seen as a beautiful woman. We both stumbled out to the table in a fairly tipsy fashion. As we left the bathroom a few of the people waiting smirked at what looked like a pair of bathroom lovers leaving and interlude behind.
Once back at the table we each smoked a cigarette and I then refreshed my lipstick the way my girlfriend showed me how. Mike asked if I was sure I never dressed as a woman before since I looked so natural doing that. Again I felt flattered to be doing things so right. I really felt I was a sure bet to win this year again. Just then one of my all time favorite songs came on and I stood up to go dance. I grabbed Mike's hand and dragged him out to the dance floor. I really got into the song and was shaking and swirling for all I was worth. Again I forgot I was dancing with a man. When the next song came on it was a slow song and so we continued dancing. I felt Mike's hands on my ass almost instantly and this time (to my surprise) I even enjoyed it. When his hands squeezed down again I smiled at him and groaned a little, which made him give me an odd yet not unhappy look. I guess having skipped dinner in order to get all of the preparation done wasn't such a good idea since I'd had so many drinks. He slowly turned me around and I wrapped my arms around his neck as I felt his hands on my hips. We swayed and turned and eventually I felt his crotch right up against my ass again. This time I didn't pull away but slowly slid my skirt back and forth against it wanting to see if I could be "woman enough to turn him on" (like I said a lot to drink but nothing to eat can be trouble). Sure enough within a few minutes I felt a large bulge pressing into my ass. When I didn't pull away Mike slid a hand under my skirt and gently rubbed my hip where the stocking stopped. Turning around I gave him a quick look of what are we doing here? Both of us were a little shocked I think at our behavior.
Taking his hand I led him back to the table before anything else happened. As we sat there silently drinking we both kept trying to talk but couldn't think of what to say. I finally told him that I'm not gay but I did get turned on out there and actually forgot for a few minutes that I wasn't a woman. Mike told me he wasn't gay either and had also forgotten I wasn't a woman. He told me that for being a man I was one of the hottest women he'd ever danced with. When he said that he put his hand on my knee and it made me shiver a little. I realized all that dancing and drinking had made me have to pee again so I excused myself. Mike again stood to go with me and so off we went to the bathroom. We both got in there together again (no line at the moment) and I freshened up my lipstick again after peeing. As I turned to go out the door Mike grabbed me and wrapping his arms around me gave me a deep kiss. I jumped back a little but then returned the kiss and wrapped my arms around him as he pulled me hard against him. His hands squeezed my ass and I loved it. I had about 20 conflicting thoughts ranging from: am I gay? To why did he wait so long to do this? To why am I enjoying this? As we kissed I reached down and squeezed his fully erect cock and noticed that I had a bulge in my panties as well. We finally pushed away from each other and then both tried to apologize simultaneously which made us both laugh. I looked in the mirror and saw how badly my lipstick was smeared and did my best fixing it. He wiped off his face and then asked if I was ok with him having done that. I told him it was fine. Although it felt weird to do it also felt good.
We headed back out to the bar and sat down at the table to finish our drinks and then it would shortly be time for the contest to start. As we sat there I thought about how good it felt touching him as he squeezed my ass. Deciding that this was something I wanted more of I put my hand under the table and grabbed his thigh while leaning forward to ask if he wanted to go back to the bathroom. He smiled a little bit and said it would be great but that if he drank anymore he wouldn't be able to drive me home. I said well then why don't we just leave now. He asked if I was going to just give up on the contest and I said forget the contest.
He stood up pulled out my chair and once I grabbed my purse we were out the door. I stopped to let the people at the contest know I was withdrawing and met Mike outside at his car. He leaned me up against the side of the car and gave me another deep kiss. Unlocking the door he opened it and I got in. While he was moving around to his side I was trying to adjust the bulge in my panties. As he started the car he asked my place or yours? I didn't know for sure what time my girlfriend would get home and didn't want to explain why Mike was there so I said his place. As Mike drove I kept reaching over to stroke his hard cock through his pants. While I had never thought I'd want to touch someone else's cock I found that I couldn't stop now.
About 10 minutes later we were on our way up his front steps and by the time he had the door open and we were inside his hands had lifted my skirt up and he had his hands down the back of my panties as his tongue explored my mouth. I lifted his shirt and felt fairly toned abs and taut back muscles. I shuddered as I felt his fingertip slide between my ass cheeks. He then picked me up and carried me to the couch. We sat down and continued touching and kissing. I ran my hand down his stomach and then untied his scrubs and pulled his pants down until I could reach his underwear. Sliding my hand under the elastic I felt another man's cock for the first time and also felt a very large amount of precum. I slid down to the floor on my knees and slowly kissed my way down his chest licking and nibbling on his nipples and then had him lift his ass so I could pull his pants and underwear down. Right as I was at eyelevel with his crotch I got my first look at his cock. It was about 7.5 inches long and fairly thick.
Taking a deep breath to steel myself for the next moment I looked up at him and gave a little kiss to the head and then licked the whole shaft from top to bottom. He moaned and pushed his crotch towards me a little. Smiling at that I slowly took the whole head into my mouth and then the whole shaft. As his pubic hair touched my nose I gagged a little and sat up for a moment until I recalled a trick my girlfriend used when she went down on me. I wrapped my hand around the shaft to shorten the amount I'd have to suck. Slowly I sucked, my head bobbing up and down on his cock. He thrusted his hips forward and back in synch with me until, with a shove and a shudder I got my first taste of cum. I swallowed every drop like a good woman would and then while continuing to stroke his still slightly erect cock I got back on the couch and began kissing him again. He pulled me up on to his lap and started kneading my ass while kissing me and then lifted my arms up over my head to pull my mini dress off.
Seeing my gorgeous purple lingerie and full breasts made his cock perk up again quite nicely and so helping me to my feet he led me by the hand into the bedroom. I sat down and took his cock into my mouth again before he gently pushed me back and then went to his dresser and pulled out some lube and a condom. He explained his ex-girlfriend liked anal sex and so he had the lube from when they dated. I told him I was just glad he had it on hand. Sliding a condom onto his now fully hard cock he pushed me back and slid my panties down off and onto the floor. Lifting my legs he smeared a bit of the lube onto my ass and then slathered it onto his cock. He asked me if this was something I really wanted to do. I didn't want to think about it since I hadn't done anything but try and enjoy what was happening so far. To answer I just leaned back and spread my ass cheeks. Fuck me Mike I begged.
Slowly he rubbed his cock against my tight hole until finally he slid in and I groaned with the pain and pleasure of it. Slowly he filled my ass until he was finally buried to the hilt. A few seconds of agony later I sighed as the feeling turned to a wonderful full feeling. With great gentleness he began sliding his hot thick cock in and out of me. Within a few minutes he was frenetically pounding away at my ass as I stroked my hard cock and thrust back against his cock. With a few more strokes I finally felt a dam burst behind my eyes and then felt myself start to cum. Oh god yes I screamed as Mike continued to pound his cock into my hungry ass. Finally with a yell he started to orgasm and I felt hot jets pulsing into the condom. He slowed down and then leaned down to kiss me. Thank you so much Gabrielle. That was wonderful.
We both lay there for a while until I realized how late it was and stood to go get dressed. He stood with me and gave me a kiss as I pulled my panties up. He followed be back to living room as I put my wrinkled mini dress on and then gave him another kiss before getting ready to call a cab. He told me it was no problem getting a ride which made us both laugh. I waited while he slipped on some pants and a t-shirt and then we got ready to leave. As we drove to my house he asked if he'd ever get to spend time with Gabrielle again. I told him at least once a month Gabrielle would love to spend some time dancing and drinking. When we pulled up in front of the house my car was the only one there and I asked Mike to walk me to the door. We got to the door and shared another kiss when my phone rang. I answered and my girlfriend said hello. She was making sure I made it home ok. I told her I was just getting in the door now. She asked if I won, I told her nope didn't win the contest but I did have a fun night, as I said this I gave Mike's cock a nice squeeze. She told me she'd be stuck at the clinic until at least 10 am at the earliest. I told her I was sorry and that I'd see her when she got home.
Feeling Mike's cock made me want to feel it deep inside me again so I led him inside and then turned and got on my knees and unzipped his pants. Pulling his still slightly sticky cock out I slid it into my mouth and start frantically sucking it wanting to taste his sweet salty cum again. He pulled me and then started stroking my cock through my panties while kissing me. He knelt down and licked my panties and then pulled them aside and slid his mouth onto my cock. Pushing me against the back of the couch he sucked me until I was rock hard. I knew I needed to feel that cock of his in me and quickly grabbed some of my own condoms I slipped one on him and then bent over the couch. Not passing up an opportunity he grabbed my hips and slid his way in. He fucked me until I almost passed out from the pleasure and pain of it. I felt another orgasm ready to burst and then felt myself start coming as I screamed out in perfect ecstasy. With a mighty thrust he pushed his way deep into me and then filled that condom with cum.
Pulling out he pulled his pants up and then helped me stand. Giving me one last kiss he told me to call him. I promised I would and then walked him to the door. I did eventually call him and now Gabrielle and Mike play together as often as possible. I eventually told my girlfriend everything and now she helps me plan outfits to wear and helps me make sure to look as hot and slutty as possible whenever I go play with Mike. Last week Mike wanted to try dressing up and he looked pretty good too, so tonight it's Gabrielle's first time with Michelle. I get to be on top tonight too :) I'll be sure and try and get some pictures of the two of together, either at the drag bar we go dancing at or else me riding that tasty thick cock of his.
Author's Note: This is a work of fiction (my first actually).