'Hey girl, watcha doin?'
To this day, I don't know why I answered like I did.
'Pleased to meet you, Jess! I love that show too! You actually look like Jess from that show 'New Girl'!'
'You're kidding me, right dude? I don't look at all like Jess, and that is not even my costume! For your information, I don't look like that actress, and furthermore, I am a man dolled up like a woman for a Halloween party. My girlfriend had to use the can and we stopped at this bar on the way to a Halloween party at a friend of ours.'
You should have seen the look on the man's face. Complete and utter shock! My new friend at the bar was a huge man, probably six foot 6 and weighed around 300 pounds. But he was dressed nicely. An expensive blue pinstriped suit and $500 leather shoes. Even sitting beside me on the bar stool, he was much bigger than me! Eventually his look of shock wore off and he asked me to tell him why I was dressed like I was.
'Well sir, it's a long story and I don't have the time, really. My girlfriend should be back any second'
'My name's Brian. Please start your story! You know women and washrooms! She could be a while!'
'Oh for sure, Brian! Okay, I could start my tale anyway! Olivia, my girlfriend, is a beautician, and awfully fussy about looking just right, especially her makeup! So let's see, I will start! It was about a month ago.'
I had had a long day at work. My name's Tim by the way. I'm in insurance. Big Insurance company. I investigate false claims, people trying to rip off the company, that kind of thing. Anyway, I came home around 7 p.m. and Olivia had a nice chicken dinner ready for me.
'How was your day, sweetie?'
'Pretty good Olivia. I caught two men on film who were supposedly on disability. Idiots! The boss is real happy with me!'
'That's amazing Tim! I'm so proud of you, baby!'
'Why thanks, honey. I'm proud of me, too!'
'What's new with you Olivia? This chicken is out of this world, by the way!'
"Oh, I almost forgot! You know Halloween is a month away, eh Tim? Well, you know Joyce, the owner of the beauty salon I work at? She had a brilliant idea! She wants to host a Halloween party at her place, and you will never guess the theme!'
'All salon workers have to come as French maids?' I said.
'You wish, mister! What is it with men and French maids? Besides, you made me dress as one LAST Halloween, remember?
'I sure do, Olivia! You looked so sexy in that black satin uniform, with your long sexy legs tucked into 5 inch black pumps!'
'Not this year, buster! No, the theme is quite in keeping with a salon. All the spouses and significant others of salon employees have to be made over at the salon into 'women'! All the guys will be made over at the salon by their partner. And there is a quite substantial prize for the top 3! The winner will get $1500, 2nd place is $1000 and 3rd place is $500! Tim, I intend to win us the top prize money! So watch out. on Halloween, you're going to be the prettiest 'girl' at the Party!'
'No way I'm doing that shit! I'm too macho to be made over into a girl! That's impossible! I will be the ugliest woman ever! Please honey, do we have to go? I'd rather stay home anyway and watch you hand out candy to the kids in your sexy French maid uniform!'
'Yes way, Tim! All salon staff must makeover their partners! It is expected of us. It makes us look good to the owner if we are team players! And there are several promotions to come at work! I need the raise a promotion would bring. Do it for me honey! Please? Or I may just have to find a more sympathetic boyfriend!'
''Oh all right! Damn it, do your worst, Olivia! But there is still no way you can make me beautiful. No way whatsoever!"
'Ok tough guy, you're on! That is a challenge! You know I am one of the top cosmetologists at my salon? I'm going to make it my mission to make you into a stunning girl, and win 1st prize!!'
'Haha! Like that's going to happen, Olivia! I'll come in dead Last for sure! You're going to be wasting your time! But, whatever!'
'Hmm, you seem to like French maids. I was going to just make you over into a beautiful girl, and throw you into a minidress... BUT...why not make YOU a beautiful French maid?!! You'll win for sure!! No one could top having a partner transformed into a darling and dainty French maid! 'You're kidding me. Olivia!'
'No Tim, I'm not kidding! Come Halloween, you are putty in my hands at the salon! Oh, and I have JUST the outfit! The French maid uniform you bought for me last year! It may be a bit tight, but I'm sure a corset will let you slip into my uniform! That, and a little dieting for the next month! I'm afraid Tim that on Halloween, you will be a sweet serving 'girl', a French maid named 'Tiffany'!!'
What had I got myself into?
'Woah, that is quite the story, Tim! You're a sport for doing this for your girlfriend! I don't think I would have the guts to go out in drag! Especially in a French maid's uniform! Say, your girl is still not here! Could I buy you a drink? Just one!'
'Well, ok Brian! No harm in one! I'll take a rum and coke, please.'
A few minutes later, I was nursing a nice rum and coke, and beginning to loosen up a little around Brian. That was when my girlfriend ran out in a panic, and I asked her what was wrong?
'Oh Tim! I have an emergency at work! I'm so sorry, but I have to go back to the salon for a few hours! We got Some last minute clients for Halloween, and I'm one of The few stylists available! Joyce called me personally and told me that if I took care of the clients tonight, I would be sure to get a promotion! I'm so sorry, baby, But I will see you in a few hours, okay Tim? Then we will take you to the party and win that prize!!'
'Okay Olivia, I understand. This could be your big break! Go ahead, do your magic, and I'll be waiting here for you later. Besides, Brian here is good company and will keep me company!
'Oh, you're so sweet, Tim! No wonder I love you! I do have to marry such a sweet man like you, eventually! Okay, see you in a couple hours!'
And with a quick peck on my cheek, Olivia was gone, leaving Brian as my company.
'Woah, I see you finished your drink! Buy a girl a drink?'
I played up the femme fatale and thanked Brian for a second rum and coke. Which, as I continued my story, turned into a third drink!
'So 'Tiffany', tell me about today and your transformation into such a stunning girl, and French maid, to boot! I'm amazed. I would never have known you were a man at the bar when I saw you!"
'Okay Brian. Well, last night, the day before Halloween, Olivia shaved my entire body, so I could be hairless and smooth, as 'girls aren't hairy' she said. I was surprised at how my body felt hairless and smooth. Quite a different feeling, and not unpleasant. Olivia and I made passionate love that night, believe me! It was wonderful!'
'Hmm, I have to say 'Tiffany', that your smooth legs were what drew me to you when I saw you at the bar! So lovely! The prettiest gams I have ever seen, and you're a dude! Go figure! Haha!'
'Why thanks Brian! I guess! Never had someone tell me that before!'
'My pleasure, 'Tiffany'. Now please continue your story!'
Ok, well this morning we slept in then had a nice breakfast together. Eggs, toast, sausage, the usual. Filled up, we left for her salon around 3 this afternoon. I was in my khaki trousers and sperry boat shoes and a white golf shirt. Olivia looked hot as usual in a sexy black miniskirt and heels. There was no need to ask what was in her garment bag that she was carrying! I knew it was the maid uniform and all the rest of the clothes to make me into a maid!'
'Hard to believe this gorgeous creature beside me was Wearing khaki trousers just this afternoon!'
'Tell me about it Brian!! I can't believe the change myself!'
'So tell me about your transformation, 'Tiffany'.
Brian was enjoying talking to this sexy maid. And as 'Tiffany' loosened up, he got a strange idea in his mind. Perhaps a few more drinks? Yes, that would do it!
'Please continue 'Tiffany What happened at the salon?!'
'Okay Brian, well once we got there, I was put near the back, and into a chair. The first thing Olivia did was my hair, and instead of a wig, she added extentions to my hair, after washing my hair first. My hair is dark brunette, as you can see, but before the extentions, It didn't even reach my collar! As you can see, my hair now goes all the way to my waist! It took some getting used to, believe me! The weight was quite unfamiliar to me, that's for sure! Then she curled the ends of my hair to add some sexy curls and body to it, then trimmed my normally parted hair into bangs, you know, like the girl in new girl!'
'hmm yes, your gorgeous hair was the third thing I noticed about you, 'Tiffany'!'
'Third thing? What was the second thing, Brian?'
''Duh! Your tits, 'Tiffany', straining out of your black satin uniform! They are VERY impressive! What, a D cup?'
'Oh, er, those! Well, they are a DD cup actually! They were the next thing Olivia did to me! I pleaded with her for smaller breasts, But she wouldn't have it any other way. Maids should have big boobs, she told me firmly. And so, with her glue and makeup, I was soon the proud owner of a pair of double d's!'
'Quite fetching they are, Tiffany! They suit your costume most elegantly! So what came next? Makeup? Or more dressing?'
'More dressing, then makeup! Soon I was wearing my first bra, a black satin and lace number that supported my new 'girls'! Then she slipped a pair of panties on me. My, how unusual and sensual they felt! Not at all like my rough, cotton briefs! The panties were black satin, bikini cut, with white lace around the waist, legs and white lace ruffles on the back! It all felt so girly, and forbidden! But it only got worse!
'Yes, I can see by your figure, 'Tiffany', that you must be corsetted!'
'Yes sir! Man, that was torture, but I'm used to it now! Olivia brought out an old fashioned boned corset and wrapped it around me, doing up the buckles in front and severely lacing me tight in the back! The corset was black satin, of course, and soon I was the proud owner of a 26 inch waist! I was a 32 waist in my khaki's!! It was almost unbearable at first, but now I'm used to the tight lacing. It really hugs my body!'
'Very sexy body, 'Tiffany' One of the curviest 'girls' I've ever seen! Girls today just don't take care of their figures like they used to! So what came next, sweetie?'
By now, 'Tiffany' had knocked away 4 rum and cokes, and Brian noticed that 'Tiffany' was getting a little flirty and quite feminine. As if Tim was Disappearing, and his feminine side, 'Tiffany', was taking over. This could work out well, thought Brian. Yes, indeed!
'So, after I was corsetted, it was natural to be put in stockings next. Olivia brought out a pair of sheer, seamed black silk stockings that must have cost a fortune! Each stocking was drawn up my smooth, shaved legs and gartered in three spots on each leg to the corset. I tell you, that was a rush! The pull of garters holding up stockings is something I never experienced before, and it was intoxicating! Olivia smoothed my seams in the back and when I felt her hands on my silken legs, I almost creamed my panties! But I couldn't. Oh, I forgot to tell you that Olivia locked me in a plastic chastity tube after pushing my balls inside their natural pockets. I had quite the flat front! Olivia wanted an authentic looking 'female' domestic, not a cheap looking man in drag! With my flat front and my penis in chastity, I certainly didn't feel very manly!'
'Indeed 'Tiffany'! I see no sign of male bits under your skirt!'
'Oh you! I'm sure the white lace and taffeta petticoats help hide my front! I know you can only see one petticoat, but I am wearing 3! Olivia wanted my maid uniform to 'poof out' to hide what little remained of my pantied and chastised front! Sooo, after the three petticoats, came the dress! The same one she wore last year for Halloween! Black satin and trimmed with white lace at the collar and arms! I don't know how she did it, but I was soon dressed in it, and it fit! It must have been the tight corsetting! I was amazed it fit, and so was Olivia! I now had the same waist size as her!'
'Hmm, lovely! Real satin? Nice, 'Tiffany'!! Stand up! I want to see how short it is!'
'Uh, ok Brian! See, it comes down mid thigh, and shows off my petticoats, with just a hint of stockings!'
'Hmm, yes 'Tiffany'! I like! No, I LOVE! Very fetching maid! And I love the hint of stocking tops with the garters!'
'Gee, thanks Brian! Tee hee! Wee!'
It must have been the drinks, but soon I was twirling around for him, around and around, surely showing a peek of my panties to him and the bar crowd. I was so dizzy I had to sit down. I was embarrassed. What had I done! And WHY!?'
'What a gorgeous maid you are 'Tiffany'! Sublime! So sexy!'
'Why thanks, kind sir!'
'My pleasure, 'Tiffany'. How about another drink? Yes? Bartender, she'll have another rum and coke, please!'
'So, 'Tiffany', what came next?'
'Well, Olivia completed my maid attire with a cute white lace apron, and the lace choker I am wearing. Then she slipped me into a pair of 5 inch black pumps. Man! I could barely stand! But she had me practice for a while, and surprisingly I was able to mince quite well, maybe because of the tight corset?'
'You're a natural maid, 'Tiffany'. Very convincing and beautiful, like a real female French maid! So what happened next, my darling maid?!'
' Makeup! And lots of it! Liquid foundation, powder, blush, you name it! She even applied long false eyelashes on me and glued them on! Then copious coatings of a dark mascara, thickening my lashes to ultra feminine proportions! The weight alone is incredible! I can barely keep my lashes open! Loads of eye shadow in various subtle hues of blue. Then she lined my lips with a pencil, and filled my new shaped lips with a deep red lipstick, followed by a gloss! Talk about a strange feeling! I was used to kissing girls with lipstick, not wearing it! But it felt devine! And my lips looked unbelievably sexy and feminine! I wanted to kiss myself, for god's sakes!'
'Oh 'Tiffany', I have to say your makeup is impeccable! You look so lovely, you take my breath away! You don't look at all like a man in drag! Just the most beautiful French maid in the world! Wonderful!'
'You really think so, Brian? I mean, guys just don't turn into gorgeous girls, or maids, with makeup, do they? I thought i was so macho! This feels so weird! Like someone else is in my body1 I feel so feminine! I don't know what is happening! But I kinda love the clothes and makeup. That's so silly, eh?'
'Not at all, 'Tiffany'. Just think of yourself as a woman tonight. Ok? Not a man in drag, but a lovely female maid! And enjoy it. Go with it! It's only for a night, eh? Then you will be your old boring male self. So let your feminine side shine tonight, 'Tiffany'. Another drink? Good girl..... That's my 'Tiffany'!!'
Two and a half hours later, Olivia returned to the bar to fetch Tim. But there was no sign of him! Olivia asked the bartender what happened to the cute brunette French maid.
'Sorry miss, that sexy maid left a half hour ago! She left with her boyfriend. Cute couple they make!'
Olivia was in shock. What was going on? Why did Tim leave with a strange man?' This was absurd! Then the bartender gave her a note.....
'That huge guy that sexy maid was with. He told me to give you this.....'
End of Part One