CAUGHT AND MAID TO ORDER
PART ONE
It had been a long, first day of a four day business conference; I could only thank myself lucky that we were all staying in-house, at the resort, for the entire time. After the final session my colleague, Ashley a somewhat reserved but cute account executive and myself had decided to meet up for dinner later somewhere downtown.
I needed a shower and a freshen-up so I took my leave and headed up to my room, with instructions for Ashley to call me on the house phone in an hour or two and we’d head out. I would be lying if I said that I wasn’t in the least bit interested in her…she had a look and style that is, in my books, “ruebenesque” – very curvy and voluptuous, not model material but not in the least bit overweight. A body that wore outfits of a “classic” nature so easily and fluidly. Ashley would be about 5′ 7″, a nice height for a woman in my books.
As is my want on these occasions of business travel, I make sure I pack a few items of my other self…a confirmed crossdresser; I take every opportunity to indulge my desires while I am away. Once back in my room, I showered and did some touch-up shaving to my legs and around under my balls.
Applying some body-lotion after showering set the all too familiar tingles starting through my body. I stepped up to my bed upon which I had laid out an outfit for the few hours I had to kill before meeting Ashley. As it was only a short moment, I wasn’t going to go to too much bother but I had decided on some very nice lingerie.
Slipping off my dark-plum, satin bathrobe, I chose a pair of very sheer, light-coffee coloured pantyhose. These ones had a very high sheen, and catch the light as you move, creating a nice shine on the leg. Pulling them up around my waist I could feel my ‘girlie-cock’ begin to harden under that electric sensation of nylon and Lycra against the skin…that tight constricting feeling surrounding the butt and legs! Next I took a simple, black lace-edged camisole and slipped it over my head.
I lightly pinched my nipples revelling in the way my girlie-cock twitched again. I sat down at the dresser and applied a nice coat of rich, “suck me off” lipstick, a light coat of eye shadow and a little facial powder was enough for the moment. Finally I slipped on my wig (I always carry it with me — finished off the look so very well), a nice shoulder length model much in the style of Loraine Bracco.
I had opened a bottle of iced champagne when I first got in and now with my lipstick on, marvel at the site of the marks on the edge of the fluted glass as I take a sip…
I had laid out a simple black dress in silk/wool, long-sleeved with little white cuffs and a white lace collar. I have had the dress altered to fit closely to my waist and down around my thighs. A slit up the left thigh completes the design.
There is something to be said for the constricting feeling of nice outfits such as this…it creates a constant massaging of all those important areas! The finishing touch to this outfit was a pair of drop-dead gorgeous patent black leather pumps with a 5″ heel.
As I slipped into them I turn to check my calves in the mirror and the shine of my legs in the sheer pantyhose. I lay down on the bed sighing and moaning with pleasure at the overall feel of all my finery. I continued to drink the champagne and, of course, after some playful self-caressing, I fell asleep!
I began to wake rather dreamily, to the sensation of soft hands running over my thighs. The feeling was extremely delicious to say the least, my dreams allowing me encounters with a gorgeous blonde willing to take her time and have her way with me. Then I heard my name being whispered, I woke fully to see Ashley sitting on the bed stroking my sheer thighs!!
I sat bolt upright, embarrassed and horny at the same time…a noticeable bulge growing under my dress. As I tried to stammer an explanation, Ashley just smiled and placed her fingers to my lips to hush me. Leaning forward she let her soft lips fall solidly onto my own. I melted in her arms and our kiss was as passionate as any I’d ever experienced, our tongues hungrily searching each other’s mouths, our hands feverishly caressing each other’s bodies. Ashley’s pantyhose felt as smooth and silky as my own, as my hands ran over her sheer legs. Her own dress rode sexily up her thighs revealing a beautiful expanse of nylon-covered leg.
After a short moment of intense, passionate kissing and heavy, heavy petting we sat back and rather shakily, I asked her how she got in and, of course, what her thoughts were. She had knocked, but as there was no answer, she convinced the house-maid that she had locked herself out and was let in. She said that her initial reaction upon seeing me was absolute shock.
“You never really know a person do you?” she said.
Then after seeing the open champagne, she poured herself a glass, sat back and while sipping, she studied me peacefully napping and began to think to herself that I actually looked rather cute — not at all bad for a guy dressed as a woman. She said she was beginning to feel little desires to want to touch me and see how the outfit and stockings felt on another person. Her curiosity got the better of her and she sat down, started running her hands over my legs and found herself, rather repentantly, definitely getting turned on. That was when she called my name and I woke.
We sat and talked for a little while longer; Ashley asking a million and one questions, and me explaining all about my crossdressing, how long I’d been doing it, how it made me feel, what style of clothes I owned etc. Ashley was getting more and more keen to explore this new situation…well, new for her anyway.
We progressed to our second bottle of champagne as she asked questions about the effort to keep smooth and trim to keep a somewhat femme-figure all the time. She commented on the fact that my smooth, shaved legs looked rather sexy encased in my pantyhose.
Then she said that, like most women, there was always that little curiosity about how another woman would feel — being that they were generally all pretty or cute in some way.
I asked if she had ever had an encounter with another woman and she looked at me with a sly smile and said, “No, but you know, you could be a very sexy substitute for such an experiment, with just that “little something extra” to offer a woman, being all girlie like you are now…the look, the feel, the smell. I could really get lost in your femme world!”
She then looked me in the eyes and said, “I have to be honest and tell you that I was hoping that something would happen between us, I do find you attractive but I always held back mainly because of being work colleagues and all that complicated stuff. But when I let myself in tonite, I had no idea the nite could turn out like this. Aaaand…the fact that there is a femme side to you makes things all the more interesting. I think we could really have some fun with this! What do you think?”
All this was obviously having a major effect on me! All this talk about lesbian-tendencies was a like a dream come true. Ashley was wearing a gorgeous little red cocktail dress, with a halter style top, fitted closely to her curvaceous body, and sheer dark-tan, pantyhose with red stilettos.
As we moved closer to each other on the bed, Ashley couldn’t stop marvelling about the feel and sensation of our pantyhose rubbing together, her legs kept scissoring over and around mine, her full breasts pushing hard up against me — my girlie-cock was so hard it was creating a large mound under my dress. (I hadn’t tucked it away between my legs as I usually do).
Slipping her hand up under my dress and grabbing hold of my nylon-encased girlie-cock, Ashley leaned closer and whispered, “You know, that little black dress with the white-lace edgings has you looking a little like a naughty, French Maid. What if I told you you better do as I say or I’ll let your little secret out?”
With my heart beating hard enough to be heard I lowered my eyes and answered, “Please don’t, no-one can know about this! I’ll do whatever you wished Miss. As long as you promise not to hurt me or, ask me to go with a man, I’ll do anything you suggest or order Miss.”
“My, my! Aren’t you just the obedient little thing! Well, I think you and I are going to have some real fun. I’ve always thought a partner I can order about and have my way with would be fun. But before we do anything we really should come up with an appropriate name for you — but seeing you like this, I bet you already have one you use don’t you?”
“Yes Miss. I like to be called Georgia Miss,” I offered.
“Georgia it shall be but, most of the time you will be called Slut or Slut Georgia when it pleases me, do you understand Slut?”
“Yes Miss, absolutely,” I offered meekly.
With a smile on her face Ashley said, “Call room service and order us some food and some more champagne. When they deliver it I want you to answer the door just as you are. And, if there is a female delivering it, you will thank her kindly and show her where to place it in the room. I’ll be sitting on the sofa watching your every move is that understood?”
“Yes Miss,” I answered.
I ordered as told then Ashley said, “While we’re waiting for that to arrive why don’t you sit beside me and tell me all about your ultimate fantasies as a woman. I’m sure a sexy slut like you must have some really wild desires and ideas flying around in her pretty little head. You couldn’t dress and be the way you are without some form of sex or fetish, entering into the equation hmmmm? Am I right?”
“Yes Miss you are right, but I’m a little embarrassed to tell you everything upfront. It just wouldn’t be right,” I answered.
“EMBARASSED?!? You’re sitting here dressed in the sexiest of all outfits looking like a just-fucked slut with someone who didn’t even know this side of you up till an hour ago and you’re worried about being embarrassed over a few fantasies?!? You better tell me Slut or your embarrassment will be company-wide when the word gets around about ‘Georgia’! In fact, don’t sit beside me, kneel at my feet and tell me all Slut!”
Ashley had taken to her dominating role rather too well I thought but it was having a wonderful effect on me. I was starting to see and respect her as a woman I could service and pleasure as long as she wanted me to.
My girlie-cock was rock-hard and it was constantly rubbing against the sheer material making things more intense every minute – I could feel pre-cum seeping from it also. Kneeling down in front of Ashley I started to explain how my dressing causes a ‘change’ in me to the point of wanting to be there for the pleasure of a partner.
A female partner — no men ever enter my fantasies, nor do they enter my normal sexual thoughts. I started to tell her how the scent and feel of pantyhose are some of the biggest turns-on I ever experience. How I like the look of a really smooth leg or the turn of the muscle and shape of a woman’s calf or thigh as it smooths up round her butt.
How the flow of a dress or reveal of a bra beneath a blouse invokes sexy thoughts of slipping my hand under a hem or running my tongue across the smooth flesh of a breast encased in a sexy bra.
“Go on,” she encouraged softly, “this does sound interesting, I want to hear everything you can think of to tell about Georgia and what she likes.”
I think my fetishes and desires may have been getting to her because she leaned back, parted her legs a little, lifted one foot out of her shoe and placed it on my lap, pressing against my hard girliecock. It was all I could do not to cum! My eyes half-closed, a soft moan escaped my lips and I continued, “….ummm…well…”
“I dress as often as possible, which is every moment really, when I’m not at work.”
“Do you wear any female items during the day, under your male clothes?” she asked.
“Um yes Miss…I never miss a day wearing at least panties, I own no male underwear at all.”
“So what do you do when you have say, a doctor’s appointment?”
“Well, I own some simple black lycra panties that could be unisex and I wear those.”
“Hmmm…you really do take this seriously don’t you?”
“Absolutely Miss — my personality is based on being femme first and male second. If it’s a cold day I’ll wear pantyhose and a cami or a bodysuit, depending on what clothes I’m wearing that day.”
“What about on weekends? Do you ever wear female clothes when you go out?”
“I often wear women’s boots with jeans, if the heel isn’t too high and I also wear women’s tops — there are a lot of unisex styles that people don’t even notice on you. Also none of my jeans are men’s they’re all women’s styles — just goes to show what you can get away with. And, of course I always wear lingerie when I’m out and about.”
Ashley sat back and smiled, her foot still rubbing slowly between my legs, “And how long has this been going on?” she asked.
“The first time I realised a liking for pantyhose was when I was about 13 or so. But the actual dressing didn’t start until I was in my 20s. As for dressing daily and being a CDer fulltime, well that has only happened in the past 10 years or so. And, I wouldn’t change it for the world! I have had a number of occasions with women where my femme side has added some serious excitement to sex!”
“So you do this kind of thing often then?” she asked rather indignantly.
“Oh no Miss; please don’t get me wrong, I don’t go out hooking or being a slut or anything. I just meant that the odd occasion has arisen where wearing panties or pantyhose under my drab clothes has been found out and well, the nite’s have got interesting that’s all.”
“Hmmm… I see. Well tonight will be…” and at that moment there was a knock at the door and “Room service!” was called. “Get that Georgia will you, there’s a dear,” Ashley said, as though she had been ordering me around for ages.
“Miss…I can’t go to the door now, look!”
I pointed to the rather large bulge under my tight dress, which she had been instrumental in forming.
“Well you should have thought of that when you dressed without panties shouldn’t you my dear? Get that sexy butt of yours to the door and answer it — NOW!”
I struggled with my hardening bulge and pantyhose and managed to push it down between my legs as best I could. Walking a little uncomfortably in my heels and with my girliecock stuck as it was, I opened the door — of course it had to be a lady didn’t it!
“Great,” I thought, and summoning up my best Georgia voice, I asked her “Please, come in, just place the tray on the table.”
She didn’t really look at me all that much but when she noticed Ashley sitting on the sofa smiling and dressed to the nines, she looked back at me and did a small double-take. It was then that I thought I was going to die, as Ashley spoke and ordered,
“Georgia, please be a good little girl and thank the lovely waitress for serving us our meal. Oh, and when you do, please curtsy to show her you mean it!”
My mouth fell open and I turned so red, I didn’t know whether to run to the bathroom and hide or just stand there and do nothing! I immediately thought this could turn bad with Ashley up and leaving if I didn’t do as asked (and trust me, the femme side of me did not want that!).
The lady was standing there not sure what to do or think, I’m sure — she was quite pretty and very young, maybe early 20’s only. She had on the usual hotel style uniform, white blouse (a white bra with lace edge very visible underneath), relatively tight black skirt to about mid-thigh, black tights, nice shoes with a sensible heel and her long hair pulled back in a tight ponytail. Her name-tag read, “Alissa”. She was just standing there with her hands behind her back.
“Ummm, that’s okay,” she said, “if you would just sign the chit I will be on my way.”
I thought I was saved until Ashley stood up and came over. She placed one hand on Alissa’s arm and said, “Nonsense my dear, Georgia here is still learning her role in the world of womanhood and she really does need to practice her manners — don’t you Georgia?”
Totally embarrassed I offered rather sheepishly, “Yes Miss.”
“Now, be a good girl and thank Alissa for her troubles.”
I turned towards Alissa, grabbed the sides of my dress and, in my best femme voice, curtsied and said, “Thank you Alissa so very much for serving Miss and I this evening, we really do appreciate it.”
“WONDERFUL!” cried Ashley, “Now that wasn’t too much to ask was it Georgia?”
“No Miss,” I answered dutifully.
Ashley took the chit and signed it off to my room and handing it to a smiling Alissa said, “You know, we are planning on a little party here tonite. If you’re interested in catching up for a chat and a drink with “the girls” you are more than welcome to join us.”
Alissa wasn’t sure what to think, she mumbled something about not getting off until eleven. She didn’t say yes, but she didn’t say no either. She just smiled and when she turned to leave Ashley grabbed a business card from her purse and said, “Here, just in case you change your mind and think the nite could be some kind of fun — call me.”
When Alissa left I turned to Ashley and said, “That was so embarrassing Ashley! How could you ask me to do that?!?”
“Excuse me?!!?” She said, “Who the fuck do you think you’re talking to bitch! How dare you raise your voice to me like that, either you apologise right now slut or I will walk!! And this little…whatever it is, is over with right here, right now!”
Ashley was standing there, legs wide, her purse in her hand and hands on her hips looking very annoyed and ready to leave any minute. I really did not want to lose what had already happened and what, more importantly might very well happen, so I lowered my head and in the best subservient, sissy Georgia voice I could muster said, “I am so very sorry Miss. I sincerely apologise for that outburst. It will not happen again and I will do as asked or ordered from hereon in, I promise.”
“I should fucking think so you little sissy, I might be new to this game of yours but I can tell that there is a big part of you that enjoys all this immensely. That is very evident with your dress style and the care you take in looking femme. For fuck’s sake that Alissa didn’t realise that you were a guy at first glance, she had to look twice.
And for the record I do find this all very sexy, and somehow exciting being here with you as Georgia — not sure why yet but that’s not important right now. What is important and what you need to understand is that if we are going to enter into some sort of relationship it will be predominantly on my terms, is that clear?”
“Yes Miss. Very clear Miss,” I offered.
“Good, now come here and kneel down! I am so fucking horny right now I wanna cum before I eat!”
I couldn’t believe my ears! I knelt as quickly as I could in front of Ashley; she pulled up her dress and pressed herself hard against my face. Under her skirt and sheer pantyhose there were no panties. Her pussy was nicely shaven with only a little hair…very cute and very wet!
Her pantyhose were literally soaked around her inner-thighs, obviously from all what had gone on already. With my face in her crotch, she pulled her dress back down over my head, trapping me under the material. Her hands grabbed at my head and proceeded to press me into her hot, wet mound.
“SUCK ME YOU FUCKING WHORE! MAKE ME CUM, AND QUICKLY!!”
I didn’t need to be told twice — and there is nothing more I love while being Georgia, than making a woman cum by eating her out. I reached up to tear a hole in her pantyhose and she yelled, “NO! Leave them alone; make me cum through them, the nylon against my clit feels so good!!”
I leant forward and opened my mouth, sucking her as hard as I could, while driving my tongue against her clit and the sheer material covering it. Her hands pushed me hard into her making it hard to breath at times but I couldn’t have cared less — the feeling of being trapped under this woman’s dress, being ordered to suck her off like a total whore, the sensation of her pantyhose against my face and the taste and scent of her drenching pussy juices, all the while dressed as I was only helped to make me want to serve her more and more.
It only took a few minutes and I could tell Ashley was almost cumming. Her breathing got faster and faster, her hips were thrusting against me now as though she was literally fucking my whole face! She opened her legs wider and bent at the knees pushing my face harder into her soaking cunt. I grabbed her hips, pressed a finger as hard as I could between her arse-cheeks, trying to finger-fuck her cunt and arse.
She bucked and stopped momentarily, I heard, “OH FUUUUUCK!!” and then she came with a torrent…her pussy juices soaking through her pantyhose and literally cascading around my mouth and all over my chin. As I sucked and licked at her to swallow as much of her cum as possible, Ashley jerked and moaned, “F-Fuck! C-Cumming Georgia! I-I’m cumminnngggg!!”
I kept flicking my tongue and fingers against her clit making her jerk and twitch in that after-orgasm, sensitive way. She pulled back, dropped to her knees and ferociously French-kissed me, licking her juices from around my mouth and chin.
“Mmmmm…it tastes as good off you as it does from my own fingers,” she offered. “Nice,” I thought, “a woman who likes the taste of her own cum!”
We sat there cuddling for a moment while catching our breath, and then moved to the bathroom to clean up for dinner. Ashley didn’t have any clean pantyhose to put on so I offered her a pair of mine (I always pack many pairs when I travel), she is a few inches shorter than me so my pantyhose would fit her quite okay. I told her I would choose her pantyhose and seeing as she had no panties I found a pair that were sheer black and with a French-lace pantie embroidered into them.
I took her soiled ones, ran some warm water in the basin and while she watched I said, “Let me wash these for you Miss. I’ll have them nicely dry, scented and folded for you tomorrow.”
Ashley smiled and said, “You read my mind Georgia, I was just about to order you to do that!”
Dressed in new pantyhose and having fixed her makeup Ashley went out and left me to my chores.
It felt so natural standing there in my femme finery doing my duty for Miss. I had an overwhelming sense to cry, feeling as though I had found my place in life. After all the years of wishing and hoping that a woman would come along to treat me how I wanted to be treated.
And, for that woman to want someone in their life like me too — someone to serve them in the manner to which they deserve — I sincerely hoped that what had just occurred was not a one-night fling. I so very much wanted it to be more. I would just have to prove to Ashley that it could be so. After finishing my chore I went out to the suite and stood before Ashley, “Miss,” I asked politely, “could I be so bold as to ask permission to wear a control panty?”
“Whatever for sissy??” she asked.
“Well, it’s just that I am so hard and my pre-cum girliejuices are all over my pantyhose and I’m afraid I might get them all over my dress Miss. I just wish to be clean and comfortable while we have dinner Miss. And, if Miss allows me to wear them, it would also help to keep my form and figure more girlie Miss — no ugly bulges to speak of.”
“You offer a good point Georgia — yes, I think a control panty would be a good idea. We don’t want that silly little thing of yours getting all messy now do we. But, I get to watch.”
Smiling sheepishly I took a black, boy-leg control pantie from my suitcase, removed my shoes, lifted my dress up around my waist, and then pulled the panties up slowly. I then my pantyhose down to tuck my girliecock between my legs, which was hard because it was still semi-hard and very slick with pre-cum. Ashley watched with a smile on her face as I pulled my pantyhose back up, then my control panties over the top…smoothing my dress down and finally slipping into my shoes, I stood and offered a twirl in front of her.
“Good lord Georgia! Your figure is lovely — especially now that that ugly bulge has gone. I kinda thought it was sexy seeing it sticking out from your dress, but you know what? Seeing you like that and just knowing that there is a gorgeous cock under all that finery is even sexier than actually seeing it! And in that dress, your butt is seriously cute too! Who knows, we may have to see about fucking that sometime!”
Hearing that, my heart skipped a beat, my knees almost buckled and my mouth must have dropped open because I heard Ashley say, “Snap to it Sissy! Stop acting like that is something new to you. I bet you’ve dreamed long and hard about someone taking your cherry. If you’re half the sissy or slut that you look and act like, I bet it’s on the top of your list of ‘must-dos’. Now get over here and serve me before this dinner goes cold and we have to get Alissa to serve us again!”
On excited but trembling legs I moved to Ashley’s side and began placing her dinner before her, opening and pouring the wine and settling her napkin on her lap — all the while her hands were running up and down the backs of my legs, teasing me by slipping up to my throbbing girliecock, confined so very nicely in all its finery.
“Thank you Miss. Thank you so much for making me a very happy girl tonite,” I offered.
“Oh Georgia, it’s not just going to be for tonite, I think we could have a very long and happy future ahead of us, don’t you?”
“Yes Miss,” I added, “I do hope so Miss and thank you again.”
Ashley looked up to me, her hand still firmly between my legs, her fingers rubbing and pressing into my crotch, “Sit down dear and eat your dinner and maybe later we can do something about this,” she said pressing her fingers hard against my throbbing bulge.
I took my place across from Ashley and as I started to eat she asked, “Why don’t you take up where we left off before room service interrupted us. You were telling me all about growing up as Georgia and all that goes with being femme — continue Sissy…”
Omg laci that was absolutely amazing that was one hot horny story, thank you so much for sharing,xx
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