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My First Business Trip - Part 1
🕑 Added 2021-01-12 10:30:37 +0000 UTCI was nervous and excited on the way to the airport. This was to be the first business trip to my new job. I was on my way to a two-day seminar with three of my co-workers. All of my co-workers were female and senior to me. One of them, Nancy, was my boss.
We arrived at the airport and the skycap took our luggage. We found our gate and soon were in the air. The flight was a long one and we started drinking cocktails after the meal. It was really the first time I had spoken in a social setting with the three women.
Shelly was a pixieish woman with a crooked mischievous smile. I knew from office gossip that she had lots of lovers but was not a slut Shelly just liked men.
Cathy was a tall woman. She was large, very Rubenesque. She was Italian and very dark with long jet black hair. She exuded a smoldering sensuality.
Nancy, our supervisor, was an older woman with close-cropped salt and pepper hair. She had a very commanding presence and was always in charge no matter what the situation.
One thing all three women had in common was that they were always immaculate in appearance. Each had the touch of a professional when it came to makeup, and even though they were competing in a man's world, all three women were the epitome of femininity at all times.
We arrived at the airport and upon deplaning I felt a little tipsy. A glance at the women showed that they were too except for Nancy, who was always in control. We went to the baggage carousel to retrieve our bags. As the bags went by and the machine spun around I felt nauseous. I was happy to grab what looked like my bags and haul them to a waiting cab.
We arrived at the hotel and were shown to our rooms. The seminar didn't begin until the next day but there was a mixer scheduled for later that night in the ballroom for all participants.
We were in adjoining rooms. Nancy's was a suite. I went into my room and set the luggage on the bed. As I did I noticed a worn spot on one of the suitcases. "That's funny," I thought to myself, "I don't remember that spot."
The connecting doors to the rooms were all open and the three women and I were talking back and forth so I wasn't really paying attention as I opened the suitcase. I wasn't even looking as I reached down to take out an undershirt. Instead of the cotton undershirt, I felt something very cool and smooth. It was like reaching into cool flowers. I looked down and saw that it was women's underwear, lingerie. The entire suitcase seemed to be filled with nothing but lingerie. Instead of the white, I expected to see there were pinks and lavenders and sleek black. I started pulling the frilly things out. They were as light as air.
I opened the other half of the suitcase and found blouses, skirts, a pair of black 2" heels and a pair of pink 4" heels. Off to one side was a large plastic bag full of makeup. I was in shock but thought I would be OK. But when I opened the other bag, instead of finding my men's business suits I found women's business suits instead, along with a pink designer cocktail dress and a beautiful little black dress.
I let out a moan and the women came running to see what was the matter. When they saw they open suitcases they began to laugh hysterically. They began to tease me. "My, you have good taste in panties." "Look, he wears a push-up bra." "You could catch a man in that black dress honey." When they calmed down a bit Nancy called the airport. I could see her frowning as talked on the phone. She hung up and said. "The airport has no unclaimed luggage. It seems that whoever got your bags
hasn't opened them yet and noticed the mix-up. Until that happens you're stuck."
I was in trouble. For comfort, I had just worn old jeans and a sweatshirt on the plane. The seminar was about to begin and I was in a strange city with no good clothes. I had another problem. My credit cards were all at their limits. I didn't have enough money to buy a new suit of clothes for the seminar.
I sat at the end of the bed in shock. I was sure I would miss the seminar now and probably lose my job as well. Sadly I explained my predicament to the three women. They consoled me and patted me on the shoulder saying, "We should be able to think of something." I noticed that Nancy had gone back to looking through the women's clothing in the suitcase. She held up one of the suits and cast a critical eye towards me. She picked up one of the high-heeled shoes and said, "What size shoe do you wear?" I told her and she motioned over the other two women. They huddled for a moment and I thought I heard giggling. When they turned around all three had a devilish gleam in her eye.
They came over to where I was sitting and stood around me crowding close. "Now," said Nancy, "as your supervisor I am telling you right now that if you miss this seminar, you will lose your job." My heart sank at her words. "But," she continued, "the girls and I may have a solution to offer you." I felt a glimmer of hope. I was so glad that Nancy had decided to help me. "You don't have your own clothes but you do have these clothes." She pointed to the suitcases and my heart sank.
"But Nancy, I stammered, "I can't wear these. I can't wear dresses."
"I'm a man."
"Listen to me, by some kind of crazy coincidence the stuff in these suitcases seems to be in your size. Even the shoes will fit. It seems like fate to me so you might as well go along. Besides, when you get right down to it it's this or your job." I could not argue with that and after a few more moments of hesitation, I lowered my head and mumbled,
"Oh, all right."
I was sent off to the bathroom with orders to shave my entire body baby smooth. I had to use one of the women's razors from the suitcase. I sat in the tub and shaved my legs with the pink razor. "Don't forget your underarms," Nancy called through the door.
When I was done I got out of the tub and wrapped a towel around my waist. When I went back into my room I saw that the women had unpacked "my" suitcases. Dresses and blouses and skirts hung in the closet and the drawers were full of panties and bras, stockings and slips and silky camisoles. On the bed was a pair of black nylon panties with lace trim around the waist and leg. A matching bra and demi slip. "Put on what's on the bed and then we'll get started," called Nancy through the door.
I pulled the panties up my smooth legs and they felt wonderful as the cool nylon encased my rear. The bra was difficult but after a few minutes of struggling I got it on. I let the silky demi slip fall over my shoulders. It felt wonderful and fell to just below my hips.
"OK," I called out and the three women came into the room. Shelly and Cathy started giggling when they saw me but Nancy had a strange look in her eye. It was almost a possessive look of desire. She came over to me and took my chin in her hand. She lifted my head until I was looking at her in the eye. "You should do very nicely as a woman."
I was marched back into the bathroom and my hair was shampooed again then some other type of goo was put in it. Cathy just ignored me when I asked what it was. After my shampoo, a towel was wrapped around my head.
I sat on the edge of the tub as Cathy rubbed Oil of Olay all over my legs. It felt good to have her massaging my smooth hairless legs with the lotion. She left the room, ordering me to put the lotion all over my body before coming out. I undressed and rubbed the sweet-smelling lotion all over my body. For some reason, I blushed when I rubbed it on my chest. I was starting to have some very strange feelings but I wasn't afraid. I put on my panties, bra, and slip back on, and went back into the bedroom. The women led me to the vanity and sat me down to begin my makeup. First Shelly used a moisturizer on my face. After wiping off the excess she began to apply liquid makeup. The smell was delicious. She used pencils and shadows on my eyes and applied a pair of false lashes. Blusher and lipstick, and then perhaps half an hour of fussing and fixing with more paints and potions, and a feminine face began to appear.
At this same time, Cathy had begun to work on my hair. She took off the towel and ran my hair through her fingers for a few moments while studying my face. Then she went behind me and got out a huge bag of rollers. She began to put the rollers in my hair one by one. What looked like hundreds were all avered my head. Something about the color looked different too but I thought it was only because my hair was still wet.
By now a very different me was looking back in the mirror. My head was covered in curlers. They all had pink ends sticking out and as they dried they began to get tighter. My face was that of a woman's. Arched eyebrows over long-lashed doe eyes. Pink blusher brought out my cheekbones and my lips were pursed very plump and kissable red. Cathy began to do my nails. To each finger, she attached a long acrylic nail. They were tapered nails and almost 1" long. I wasn't sure I would be able to manage them but I had no choice in the matter. The women didn't ask me if I wanted my hair or nails done. They just pointed to a chair and I sat and did as they said. Something about my attire, panties, curlers, makeup, and now long nails were making me very submissive. I was no longer in control.
Cathy spent a long time doing my nails. Shelly had brought her portable hood dryer from her room so I sat under the dryer while Cathy finished my nails. Shelly came up and sat on the floor to give me a pedicure and paint my toenails the same shade of fiery red that Cathy was making my fingernails. The polish was very bright, very red and I thought it was too much. Cathy just hushed me, saying that this polish was in the makeup kit in the suitcases so that meant it went with the outfits I was going to wear.
My nails and makeup were done now and Nancy herself came over to do my hair. My tightly curled hair had dried now and the curlers were ultra-tight on my head. Nancy began taking them out. The feeling of the tight rollers being taken off was heavenly and soon she was working with brush and comb and hairspray. After about a half-hour she was done. My hair was long and curly and to my horror had been colored and frosted. It was reddish-blond now with pretty highlights. It was a very normal woman's hairstyle long and feminine with soft bangs, but could never be mistaken for a man's. I began to panic. After all, trying this masquerade for a few days was one thing, but I had to return home afterward. How could I with my hair looking like this? The woman calmed me down, saying that the color would wash right out. I had never heard of this before but wanted to believe them.
Cathy brought me a pair of pantyhose from "my" suitcases and instructed me on how to put them on. They felt so wonderful on my smooth lotioned legs. I pulled the pantyhose all the way up and then Nancy brought me the pink cocktail dress from the closet. After filling out my bra cups with some panties from the drawer, she helped me into the dress. It fit after a little struggling. It was very tight but the women assured me that it was meant to be. It had puffy sleeves and was made of pink satin. It pulled me in at the waist and the flounced skirt created the illusion of feminine curves. I sat down in my dress and Shelly brought over the pink 4" heels. The color matched my dress. Shelly put the shoes on my stockinged feet and then Cathy came over and put on long bangle clip-on earrings and matching chain and locket, a few bangles on each wrist, and a woman's watch. Last Cathy bent down and put an anklet around my ankle. It was a very delicate gold chain with a dangling heart.
I stood and looked in the full-length mirror. Looking back was a beautiful woman. She was dressed all in pink and had beautiful blonde hair in long soft curls caressing her face. Her makeup was perfect and dramatic, but at the same time very natural. The woman in the mirror turned on her 4" heels and spun in the mirror-like all women do.
I turned around to my friends and said. "I think this might work. But why am I so dressed up tonight? Is it just for practice?"
Nancy turned to me and her tone was very commanding. "You don't think we would let you come with us to the seminar unless we know you can pass as a woman do you?" "As soon as Cathy, Shelly, and I can get changed we "four" girls are going to go down to the ballroom for the mixer. If this year is like last year's seminar there should be about 10 men for each woman. You will have plenty of opportunities to practice being a girl."
I was crestfallen when Nancy told me that. What at first had seemed like an unorthodox, but necessary disguise was turning into something much more. I was having feelings that I didn't understand as I thought about the mixer and 10 men to each girl. I sighed and went into Cathy's room to watch her get ready for the party. She had invited me in and when I hesitated said, "Come on in honey, after all, it's just us girls.
I can show you some makeup tips and we can work on your voice for a while."I went into Cathy's room. I could not help but wonder if I had gone into a woman's room for life.
I sat in Cathy's room waiting for her to finish dressing. I had my smooth nylon stockinged legs crossed at the ankle with my knees together, and I was perched on my chair with my head up and my bosom thrust out the way she had shown me. Cathy was talking to me as she finished her makeup. She was explaining every step as she went. Every once in a while she would turn to me with a brush or powder puff and touch up my makeup. She sprayed me all over with a heavenly perfume and with very little coaching she had me speaking in a voice that while not angelic was at least acceptable as a woman's as long as I kept my mouth shut most of the time.
It was Cathy who first said, "Hey honey, we have to have a name for you don't we?" She called through the open door to the next room "What are we going to call our new girlfriend?" Shelly came to the door dressed only in panties and bra. Her eyes were gleaming as she looked at me. I felt embarrassed at her bold look and in fact clenched my smooth nyloned knees together with a little. She noticed this very feminine gesture immediately and she smiled a wicked smile.
Nancy came to the door and said, "That's right, what will we call our new little missy? Missy? That's it, Missy!" Cathy and Shelly laughed and said, "Hi Missy." I felt humiliated and wanted to ask Nancy to let me have some other name but one stern look from her and I changed my mind. Now I was not only dressed as a woman but my name was Missy! Even worse, I had a feeling that there was more to come. The attitudes of all three women had undergone a change. All of them were now treating me like little more than a slave although Shelly and Cathy were still very friendly.
But as I sat with Cathy while she dressed, me in a pink cocktail dress and heels, with beautiful nails and hair, I started to like the way I was. I started to enjoy shifting my hairless soft legs in my pantyhose and the feeling of silky slippery panties on my bottom as I squirmed on the chair. My slip was smooth and cool under my dress and I could feel my long earrings dangling every time I tossed my head girlishly the way that Cathy had shown me.
Nancy was ready now and she came into the room "Shelly, Cathy, Missy, let's sit down here for a minute and talk about work." What a relief!
At last, things were getting back to normal. I was so relieved to have something to think about other than the fact that I was completely dressed as a woman. But I was soon to be again in dismay.
Nancy started out OK, talking about our goals at the seminar and how we would need to use a team approach. But soon she started making references to "Schmoozing," and "Making new friends for our company." I wasn't really sure what she meant but it was soon made clear to me.
"Missy, most of the participants in this seminar are men. It is very important for us to be able to make new contacts and promote our firm in any way we can. If it becomes necessary for one of us to grant certain, shall we say, favors, to an important potential client, we will. This includes you, Missy. If one of these bigshots asks you for a date, the firm, and I, expect you to do your duty."
Nancy didn't even give me a second to consider this astounding statement. The next instant she and the other women were on their feet and hustling me towards the door. I was stuttering, "But Nancy, a date, what, what do you mean?" But then we were in the hallway, and there were strangers there. I shut up and concentrated on just walking down the hall in public in heels, hose, and a dress. I walked behind the women and tried to match the way they swung their hips and carried their shoulders.
We passed men who tried to make eye contact with us. I was scared at first and whispered to Cathy, "Why are they looking at me like that?
They must know I'm not a girl."
Cathy just laughed. "They aren't looking at you like that because they think you're a man Missy." Cathy told the others what I had said and they both turned to look at me as I swayed along seductively in my pink 4" heels. They laughed too.
We got into the elevator with four men. I kind of liked the way they stepped aside to let us in, but one of them was standing very close to me. Then, just before the car reached the first floor I felt a hand on the back of my thigh. I thought it must be one of the women playing a joke. The hand went up to my leg and under my dress until the fingers just reached the lace trim on my panties. Suddenly the car stopped and the hand vanished. I looked over my left shoulder to see which of the women had done it but only Nancy was standing there. I could not believe that she would do such a thing. I looked over my right shoulder and a man was standing there. He was tall and handsome in a boyish way and he smiled at me. Had he been the one? I was becoming very confused but I was starting to realize some of the facts of life for a woman.
We entered the ballroom and I could see that Nancy had not been kidding about the ratio of men to women at the seminar. Almost all of the participants were men. "Missy, I want you to stick with Shelly for a while," said Nancy, "and when she says you are ready, go out on your own and mingle. Be on the lookout for new clients." I started to protest but Nancy had already spun on her heels and disappeared into the crowd. Cathy leaned over to me and gave me a peck on the cheek. "You'll do fine Missy," she said. "Just remember all the feminine gestures I showed you and no one will ever guess your little secret."
"Come on Missy," said Shelly. "Now that we've finally gotten rid of those two let's get a drink and have a little chat." I was grateful to Shelly, maybe she wouldn't make me go off on my own after all. We sat at a table and ordered drinks and started to talk girl talk. Shelly told me that she thought I was really a good sport to do what I was doing. She said that she was sure that Nancy would be very grateful to me for going to such an extreme for our company.
Then she started to tell a somewhat strange story. It started out normally enough, something about one of her boyfriends and Halloween. She had convinced him to dress completely as a woman and to his surprise, he had been incredibly aroused by the experience.
To her surprise, so was she.
As she told me the last part she was looking me in the eye and I felt myself blush. She leaned forward to tell me more, but at that moment the waiter came with more drinks. Shelly told him we hadn't ordered any, he said they were from the gentleman at the bar. Shelly and I looked over and saw four men at the bar toasting us. She raised her glass back to them and I did the same. They started to walk over.
"We're on Missy," she said.
At first, I was very nervous but soon I began to realize that none of the men could tell I was not born a woman. I began to relax and even, with a little coaching from Shelly during a trip to the ladies' room, to flirt a little. Shelly had mercy on me and stayed by my side as we began to circulate through the now crowded ballroom.
I noticed one pattern throughout the night, I was trying to steer the conversation towards business and the men all wanted to talk about was me. Some of them tried to stand very close and they were constantly putting their hands on me, touching me. It was strange but quite erotic. Throughout the evening my panties were very wet and I was constantly aroused.
As it got later I began to feel tired and a little drunk. Once I almost stumbled in my 4" heels but as I did I felt a pair of strong hands grab me around the waist. I turned around to see who it was that had saved me from falling and saw that it was the man from the elevator. He smiled and said, "We meet again." I started to speak to him but Nancy appeared from the crowd. "Come on Missy," she said, "we've been invited to a go out for a bite to eat. We'll meet the other girls in our rooms and freshen up first."
We got in the elevator. We were alone. Nancy told me she appreciated what I was doing. She took my hand as we talked and this gesture from her surprised me. She had always been so cold to me in the past. When we got to her room the other girls weren't there yet. Nancy told me they might be a few minutes. We sat in her suite and had a drink and then she went into the bedroom.
After a few moments she called out, "Missy, could you come in here for a minute." I went in and found her sitting on the edge of the bed.
"Missy, my feet are tired," she said. "Come over here and take off my shoes." I went over to her and kneeled down. I took the shoes, with their 4" spike heels, from her stockinged feet.
"Now massage my feet, Missy," she said. I started to massage her feet.
Nancy found the foot massage soothing and she began to speak to me in a kinder tone of voice. She began to tell me about herself and soon told me that one of the reasons she may have appeared cold at the office was the fact that she was bi but preferred women.
I could not believe Nancy was telling me all this, she must have been drunker than she appeared.
She said she was what was called a lipstick lesbian and she was partial to lovers who made themselves very pretty. As she said this I looked up at her and saw the same look as I had seen earlier. She seemed to be staring deep into me and her lip curled into an almost cruel smile.
We heard a noise outside, and I heard Cathy calling for us. I jumped up from where I had been kneeling and left the bedroom before Nancy could stop me. Cathy and Shelly were sitting, waiting, and exchanged a knowing look when I came from the bedroom straightening my skirts.
"Hey Missy," said Shelly. "I saw that big hunk who was following you around all night."
"I don't know what you mean," I told her.
"Yeah," she said, "He may be one of those big bashful types but I noticed he seemed to be somewhere near you all night." Now that I thought about it that was true. He had been near me almost the entire night. Holding my chair, buying me a drink. In fact, I had gotten used to having him near me. I had started to like it and began to smile at him sweetly when he did me on of these little courtesies.
"Big bashful type nothing," said Cathy. "That guy just happens to be the owner of one of the 10 largest firms in the southeast. He's catch honey, in more ways than one." Just then Nancy came into the room.
"Well, our little Missy here seems to be reeling in. "Mr. Catch, doesn't she?" she said. The other women laughed but they also nodded in agreement. "It would be a real coup for me," said Nancy, "if one of my girls got that account."
Cathy brought me a lacy shawl to wrap around my shoulders and after a quick touchup of my makeup and hair, we were off to our dinner party.
The four clients who turned out to be our dates were four balding fat guys from some farm state. Nancy paired us up and it soon became apparent that she had given me the worst of the lot. He wasn't bad looking but from the minute we sat down he was all over me. Everything he said was sexual in nature and he was not shy in hinting what he would like to do to me. Once he leaned over and put his tongue in my ear as he lunged for my breasts. When I looked over at Nancy for help all I got was an amused smirk.
I somehow got through the meal and our merry band left the restaurant. The men were clamoring to go to a nightclub and Nancy said we'd go along for one drink. We couldn't all fit in one cab so we split up. I tried to stay with the women but they just shrugged me off and I somehow found myself in a cab with my date alone. He gave the driver our destination and then he turned to me. He pulled me close and kissed me. It really wasn't so bad but then his hand began to go up to my leg. I held him off. We kissed again. I thought maybe if I kissed him I could keep him occupied.
I was wrong. He began to probe deep into my mouth with his tongue. I felt his hand on the back of my head and realized he was trying to push my face down into his lap. I fought back but he was very strong.
Almost before I knew what was happening I felt the head of his cock on my red lips. I tasted his salty precome and then his hand pushed my head down and his cock was in my mouth. He was much stronger than he looked but I was also remembering Nancy's words from earlier in the evening. He began to guide my head up and down on his glistening shaft and after only seconds I felt him stiffen and his come began to spurt into my mouth. I swallowed by reflex as I heard him groan. Just as he spasmed his last the driver announced that we had arrived at our destination.
I hurried out of the cab and into the club. I was sure that everyone could see what had happened to me and I could still taste my date's semen on my lips. But no one seemed to notice my obvious distress. The other women were tiring now and after getting what he wanted during our cab ride my date seemed to lose interest in me. The men drifted off once they realized that they would have more fun elsewhere.
Nancy, Cathy, Shelly, and I got in a cab and went back to the hotel. We went upstairs. I wanted to tell them what had happened to me during my cab ride but I was too ashamed.
"Come into my room Missy," said Cathy, "I'll help you remove your makeup before bed." I went in and she let me take off my heels. It felt great but in a moment she handed me a pair of pink maribou high-heeled slippers. "Put these on Missy, Your feet still need more time in heels to help you get used to them."
She helped me off with my dress and then, after using a headband to hold my bangs off my forehead, used a cream to remove my makeup. She applied more moisturizer and then I was surprised when she began to apply some makeup. "Just a touch Missy. Just a touch of makeup so you can be pretty even in your sleep."
Nancy and Shelly came in and we chatted for a few minutes as we all worked on our nails and lotioned our hands and legs. Nancy came over and looked at my hair. "We don't have time to do your hair every morning Missy. Tomorrow you will have to make an appointment at the hotel salon for a cut and set. For tonight I'll do your hair myself. Go put on your nightie first."
I went to my room to change. A cut and set at a beauty salon? Somehow that had a permanent sound to it. I entered my room. Laid out on the bed was a short pink chiffon nightie with spaghetti straps and lots of swirling material. Ruffled full-cut panties and a long flowing gown with flounced sleeves and lacy bosom completed the ensemble. I took off my slip, pantyhose, bra, and panties and put on the lacy pink dream. I went back into Cathy's room and sat at the vanity. Nancy wetted down my hair and then applied setting gel as she put me up in curlers. Soon a pink curled head was looking back at me for the second time that day.
When Nancy was done she wrapped a pretty scarf around my set and patted my curled head.
"Good night Missy, I have a feeling this might not be the last time you go to bed in curlers," she said and she winked.
I went to my room. Shelly passed through on the way to her room and she kissed me goodnight. Her soft hand with its long red nails caressed mine as she did. When she left, I didn't notice that she hadn't locked the door.
I laid down in the bed and turned down the lights. What a day this had been! I snuggled up in my nightie and curlers and thought about all the things that had happened and all the new things I had felt.
Comments
Brianna Demonet
Can't wait for the next part
Julia Miller
This is a great premise to start the story. Our poor heroine has already had her first taste of spunk, and some say there is no going back after that happens... I have had mixed up luggage at the airport many times, but always found my bags or stopped someone else from taking them. Maybe this would have happened to me, had I not been so diligent. lol
Clive hooks
Liked this start
