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My First Business Trip - Part 2
🕑 Added 2021-01-13 12:30:41 +0000 UTCI didn't even hear the door open when Shelly slipped into my room. But I started when she slipped into my bed.
"SShhh," she whispered and she snuggled up close to me. She had on a very short babydoll nightie but didn't seem to be wearing panties. I felt her lips reach mine and our soft smooth legs began to intertwine. My eyes had grown accustomed to the light and I looked at Shelly and she was smiling and cooing, "Ohh, Missy."
I started to make love to her as a man but Shelly stopped me. "There are no men in this bed tonight," she whispered to me. She pushed me back and we began to kiss and caress. I followed Shelly's lead and we began a long slow night of passion.
Shelly pinched my nipples between her fingers and massaged my breasts as I did the same for her. She guided my head down between her legs and instructed me in the special techniques that one woman uses when making love to another. I used my tongue and fingers on her warm moist vagina and clitoris. When she tightened her thighs she pressed hard on my curled head. The feeling of my tongue probing deep into her as she stroked my curlers was fantastic. She had me turn and we slipped into a 69 position. I felt the electricity course through my body when her lips touched my erect shaft. When she began to probe into my rear with her finger I was startled at first but she said soothing things to me and I relaxed. Soon I was thrusting my rear in response to her hands as she put one, then two, then three fingers deep into me. She timed her thrusting fingers to coincide with her mouth sliding down on my cock. I was in heaven as we lapped and stroked and penetrated each other. She would not let me place my cock inside her. Even though I begged her she just laughed at me and said, "What woman has a cock darling, That's just your oversized clitty and girls don't use them like that."
When Shelly finally brought me to a climax I let out a loud girlish moan that I was sure must have been heard on the entire hotel floor. It was very intense and the power of it took my breath away. I was shuddering and my hands and feet felt numb. I fell asleep with my tongue in Shelly and her fingers deep inside me and my cock in her warm mouth.
When I first awoke in the morning I thought that it had all been a beautiful feminine dream. But then when I rolled over I felt the curlers tight on my head and the soft nightie on my smooth shaven body. It wasn't a dream after all. I was very happy. I was not really sure why.
I patted the other side of the bed but Shelly had gone back to her room sometime in the night. I got out of bed and noticed I wasn't wearing my panties. It took me several minutes to find them. I could hear the other women stirring and the doors to the rooms began to open. Shelly stuck her head in my door. She was wrapped in a towel.
"Good morning Missy," she said, "Did you sleep well?"
"Yes," I told her blushing, "when I finally got to sleep."
"Take your shower," she told me, "I'll help you dress and do your makeup when you are done. Don't forget to use a shower cap to keep your set dry."
I put on my pink chiffon peignoir and went to the bathroom to shower. I found the shower cap provided by the hotel and put it on over my curlers. I looked in the mirror before I stepped into the shower. Even though my body had not been changed by my time in women's clothing it looked very different. I was completely hairless except for a patch above my groin and had long red nails and toenails that were a matching fiery red. With all my body hair shaved off I looked much softer and rounder than I ever had before and when I tucked my genitals between my legs my body was neither a man's nor a woman's but definitely more feminine than masculine. I stood daydreaming for a moment and tried to imagine what I would look like with perky breasts with big womanly nipples on my chest. I made a kissy face at the curled head in the mirror and smiled a pretty smile.
I stepped into the shower and began to lather my hairless body with a sweet-smelling beauty bar. Shelly stuck her head in the bathroom door and said, "Hurry up Missy, we don't have all morning to make you into a beautiful working girl."
I shaved my legs and underarms with a pink razor and stepped from the shower to towel myself dry. Shelly had left a pink bra and panty set for me along with a large box of body powder. I picked up the big feathery puff and started to powder my body all over. I put on my panties and bra and my lacy pink chiffon robe took off my plastic shower cap and went into my room.
A women's business suit had been laid out on the bed. There was a black A-line skirt with a high midriff jacket and a white silk blouse with ruffles of lace at the cuffs and neck. Sheer pantyhose, a black camisole, and half slip and two-inch heeled black pumps were there waiting for me. I took off my robe, picked up the pretty camisole, and let it fall over my powdered shoulders. I then put on my pantyhose and pulled the half slip up my nyloned legs.
Nancy came into the room with Cathy. "Well, good morning Missy dear, did you sleep well last night?" she asked with a sly smile. I was sure she knew that Shelly and I had spent the night together.
"Yes Missy," said Cathy, "I thought I heard a noise last night coming from your room. Did you have a bad dream?"
I was blushing furiously. I knew they were teasing me. Shelly came into the room. "You girls leave Missy alone now. We have to get her ready for the seminar. Don't forget, 'Mr. Catch' is waiting for our little Missykins." The three women all laughed a conspiratorial laugh.
"Oh, Missy, by the way, did you call the airport to see if they found your luggage yet?" asked Nancy.
I hadn't. In fact, the thought had never even entered my mind. I was confused for a moment. The idea of returning to men's clothes somehow didn't appeal to me. I slowly reached for the phone.
"Don't bother," said Nancy, "I called them earlier and there is still no sign of your things. I guess you will have to stay Missy for at least a little while longer." I felt a strange sense of relief when I heard this. The women all noticed and smiled.
I sat at the vanity in my camisole and half slip and Cathy came over and started my makeup. Shelly came over to do my hair. Nancy turned to leave the room.
Before she left she said to me, "Missy, don't forget I have made an appointment for you at the hotel beauty salon for 1 PM. You will have just enough time between the morning and afternoon sessions."
I started to ask her why this was necessary, after all, I only had to dress as a woman for one more day after this, and then I could go home and resume my normal life. But she was gone before I could speak. Shelly told me that Nancy had some early meetings to attend. We would catch up with her later.
With Nancy gone the other girls and I (Yes, I had started to think of myself as one of the girls by now) were much looser and soon all three of us were chattering happily as Cathy did my makeup and Shelly took the curlers from my hair. Shelly did my hair in a much less festive style than I had worn it the night before and Cathy did the same with my makeup. They explained that I was going to work today, not to a party.
They both laughed at my disappointed pouting expression, but I knew they were right. Cathy put just a touch of perfume on my wrists and neck.
When they were both finished they helped me with my skirt and blouse and Shelly brought me some jewelry to wear. Simple gold clip-on earrings and a chain along with a ladies watch and a bracelet. Cathy gave me two gold rings with semi-precious stones and I slipped them over my long nails onto my fingers. I put on my black pumps and slipped the jacket over my silk blouse. I looked in the mirror and a smiling career girl was looking back at me. She looked lovely and feminine but at the same time quite businesslike. Cathy and Shelly exchanged a laughing handshake at the success of their creation and after grabbing the materials for the seminar I stood in my heels to leave the room.
"Wait a minute Missy, don't forget your purse," said Shelly with a twinkle in her eye. She picked up a black patent leather purse with a long shoulder strap and began to fill it with lipsticks, compacts, and blusher. She took a pair of panties from one of my dresser drawers and put them in my purse. She reached into her own purse and took out several tampons and put them in too. "Just in case Missy, just in case," she said. I felt the blood rush to my cheeks once again and then we were in the hall outside our rooms.
We went down to the restaurant and had breakfast. Even though I was famished the women would only let me order coffee, toast, and fruit.
"You have to think of your girlish figure Missy," they said.
On our way to the conference room, we passed the salon where Nancy had made my appointment. I was surprised to see that it was not a unisex salon. The men's barbershop was on the other side of the lobby. I felt a tingling inside me as I looked in the window of this very feminine place. Surely I would be found out if I entered this women's sanctum.
We entered the conference room and found our places. I looked across the room and there was Nancy talking to "Mr. Catch." They were chatting and joking like old friends. Then I saw them huddle close and Nancy pointed over to me. "Mr. Catch" looked over and waved and smiled his handsome smile. I found myself waving back with my long nailed, bejeweled hand. I noticed that my panties were becoming damp once again.
The morning session began and I soon found that being dressed as a woman meant that I could not sprawl in my chair like I would have as a man. I had to keep my knees together all the time and sit up straight. Every so often I would slip and my knees would start to spread but once when I did I noticed a man in a row in front of me. He was looking back and leering at me. He almost had drool running out of his mouth. I could not figure out why but then I realized that he was trying to look up my skirt. I clapped my knees together and tried not to look at him for the rest of the morning.
We took a break after about two hours and the girls and I went to the ladies' room. I was really beginning to enjoy these trips to the ladies' room where we would touch up our makeup and chat for a few moments inside our cocoon of womanhood. I tried to hint to Nancy that I was interested in what she and "Mr. Catch" had been talking about but she ignored my not so subtle hints. She said, "Don't worry Missy, I'm not trying to steal your man." That shut me up. I didn't bring up the subject again.
I was nervous as the morning passed thinking about my appointment in the beauty salon. I tried to convince myself that surely Nancy would only have them fix up my hair a little. Before I knew it the morning session was over and I found myself being marched to the salon arm in arm with Nancy.
We entered the salon and Nancy had me wait while she spoke to a woman who seemed to be in charge. Every once in a while they would look over at me as I waited. Finally, Nancy and the woman came over to where I was standing in my chic suit, heels, and hose.
"Missy, this is Miss Gilda, owner of the salon. She and I are old friends," said Nancy. I mumbled a hello in the most feminine voice I could muster.
"Hello Missy," said Miss Gilda, "Nancy has told me ALL about you and I am so happy to have you here in my salon. Please go into the changing room and take off your suit and pantyhose and put on one of our smocks."
I started to protest to Nancy. I couldn't understand why I had to disrobe to have my hair done. Nancy cut me short with a wave of her hand. "Missy, you are to follow Miss Gilda's instructions to the letter." I hung my head and once again did as I had been told.
I entered the dressing room and removed my jacket, skirt, and blouse, and then took off my shoes and pantyhose. I put on the frilly pink smock and was shocked at how short it was. It barely covered my thighs and I was sure that the bottom of my pantied rear was exposed. I put my shoes back on and reentered the salon. It felt very strange to be walking barelegged in high heels and the short smock but none of the other women in the salon seemed to notice me. Miss Gilda herself came over to me as I emerged.
"Ah, Missy, come over here honey and we'll start making you even more beautiful than you already are." She took me to a chair and I sat down.
A salon girl came over with some kind of a pot that seemed to have something boiling in it. It turned out to be hot wax which she applied to my legs. She let it cool for a moment then she tore it off. The first time she did it I let out a yelp but after all the other ladies in the salon turned to look at me I didn't make another sound. She worked her way up one leg and down the other and then she asked me, "Bikini wax doll?"
"No, no thanks," I blurted out in terror. She just shrugged and turned to go. Miss Gilda had started on my hair and another of the salon girls came over with a nail station on a rolling cart. After she set it up the nail technician came over, smiled at me, and began to work on my nails. She removed the false nails that Cathy had applied, worked on cleaning and shaping my own nails for a few minutes, and then began to attach a long set of tapered acrylic nails. They must have been two inches long. I couldn't imagine how I would be able to do anything with my hands. I felt so helpless, yet so feminine with them on.
Miss Gilda had me lean my head back into the shampoo sink as she lathered my hair with a sweet-smelling potion. When she had rinsed me out I sat back up and she began to do something to my hair with what looked like pieces of tin foil. Soon I had the pieces of foil all over my head and she began to apply a liquid to the places where she had placed the foil. There was a very strong smell. I noticed that she was wearing gloves as she used a plastic bottle with an applicator tip on my hair. When she was done she told me it would be a few minutes. I sat like this in the beautician's chair as the pretty young nail technician finished attaching the last of my nails. She used a pearl base coat polish on them and when that dried she put on a cherry red topcoat. Then she began applying what looked like decals. I could see that she was also gluing what looked like diamonds to my nails, one or two to each nail.
Miss Gilda took the tin foil pieces from my hair, rinsed it, and began to cut it. When she finished she started to put my hair up in curlers.
These were not like the curlers that Nancy had used on my hair. They were hard plastic and much smaller. Miss Gilda saw me looking at them in the mirror and said, "You act like you've never seen a perm rod before Missy." Soon my head was covered in the hard blue plastic rods and she began to apply another strong-smelling liquid to my hair. Soon she was finished and the smell of the perm solution almost choked me.
"We won't leave that on too long Missy, I want to give you nice soft curls. Nancy suggested a very curly perm for you but I think I know best what will go with your face and your new look."
I looked at her quizzically. "Oh yes," she said, "Nancy has paid for a complete makeover for you. She said it was a thank you gift for something you had done for your company."
At that moment I came as close to getting up and running away as I had the entire time since the beginning of this whole crazy affair. But the combination of the way I was dressed and the faintness I was feeling from the perm solution fumes kept me in the chair. Miss Gilda began to take my perm rods out and then she rinsed the solution from my hair. She began to work with brush and comb and blow dryer.
Another of the salon girls had removed my makeup and applied a facial pack. It was bright green and I began to take on the most bizarre appearance yet. Miss Gilda turned me from the mirror as the girl peeled the pack from my face. The skin on my face felt more alive than it ever had, almost as if I was breathing from every pore.
Miss Gilda stopped fussing with my hair and went to get a cosmetologist's cart. She began to work on my face. I was familiar by now with some of the things she was doing but her work seemed to be much more detailed than that of Cathy or Shelly. I winced when she plucked my eyebrows and hoped she wasn't taking too much hair from them.
She began to work with my makeup and my hair at the same time as she worked towards an integrated whole. She would fuss with a hairbrush and then apply a powder to my cheeks. Then she would do something with some Bobbie pins and use a very thin brush to outline my lips. She was very deft and worked quickly. Finally, she seemed satisfied.
"Almost done Missy, just one more small detail," she said. She went behind me and then I felt her take my earlobe in her fingers. I felt something cold and metallic and then a sharp pain but before I could react she was on my other side and I felt the pain in my other lobe.
"All done sweetie," said Miss Gilda and she spun the chair around so I was facing the mirror.
The fact that I saw in the mirror was familiar, but it was surely not mine. My hair was now honey blond with silvery white highlights all through it. It was styled in soft curls that flowed back off of my forehead and cascaded down the sides and back of my head. I had long bangs that fell almost into my eyes and she had done something to make the hair on top of my head rise up very high. It looked like the hairstyle of a playboy bunny, beautiful and ultrafeminine.
My thin, high arched brows were raised as if in surprise above my sultry smoldering long-lashed eyes. My cheekbones were highlighted with a pretty pink blusher. My lips were outlined and shaped into a bow with a dark pencil then filled in with a deep crimson, creamy textured lipstick. My lips were pursed into an "O" which just made them appear more kissable. I thought I looked like a real live Barbie doll and then I noticed my earrings. My ears had been pierced and long dangling gold earrings hung down from each lobe. I raised a hand to my ear lobes and saw my long nails. They were colored a beautiful pearlescent red and had swirls of gold and small diamonds encrusted in them.
I was very faint for a moment, and then I realized with a start that I was having an orgasm. I sat in the beautician's chair lost in the heavenly feeling. It wasn't at all like the orgasms I knew as a man.
It seemed to come from somewhere deep inside me and it went on and on in waves of pleasure. When it was over I realized that it had only lasted a few seconds. I looked around but no one seemed to have noticed my condition.
Miss Gilda took me by the hand and helped me up from the chair. I was in a daze as I went into the dressing room to put on my skirt and blouse. I took off my now soaked panties then took the pair of dry panties from my purse and put them on. I pulled my pantyhose up my smooth waxed legs. I put my blouse, skirt, and jacket back on then my high heels. I swayed out of the dressing room and headed towards the door.
"Bye Missy, I hope we see you again soon," said Miss Gilda. Several of the other women in the salon looked towards me as I walked towards the door. I thought I saw envy in their eyes but thought I had to be mistaken.
As the door to the salon closed behind me I heard Nancy's voice say,
"Here's our Missy now." I looked up to see her standing there in the lobby with Cathy and Shelly. She let out a low whistle as I came close.
"That Miss Gilda really is a miracle worker," she exclaimed. Cathy and Shelly were staring at me in disbelief. Finally, Cathy said, "Missy, you really are a knockout, girl." Shelly just nodded in agreement and looked at me with a lascivious smile. Then the women parted and from between, they stepped "Mr. Catch."
"Missy," said Nancy, "this is an old friend of mine who is just dying to meet you." The tall, handsome man came forward and took my hand.
"Missy," he said, "it's always a pleasure to meet one of Nancy's girls. I hope we can get to know each other better. Perhaps over dinner later?"
I heard a soft feminine voice say, "I'd love to." It took me a few moments to realize that the voice had been mine.
As we returned to the conference room for the afternoon session of the seminar I was having some very unusual feelings for a young man. But I guess that for a young man in woman's lingerie and business suit who had just come from the beauty parlor my feelings were not so strange at all.
The afternoon flew by and I don't think I remember a word of what was said at the seminar. All I could think about was my date for later that evening with "Mr. Catch." I knew his name now but I couldn't help but think of him still as "Mr. Catch." The other women noticed how distracted I seemed and teased me about it when we went to the ladies' room during a break.
"Missy," said Nancy, "you are acting like a lovesick schoolgirl."
"Yes Missykins," said Cathy. "Do you need to go to your room for some dry panties? Hmmm?"
Shelly took me by the hand and said, "You're such a lucky girl Missy, he's so handsome, and such a gentleman too. How much longer will it be until you're 'Mrs. Catch?'"
They kept teasing me this way. My newly pierced ears were throbbing a little and I couldn't seem to do anything with my long beautiful red nails. Even holding a pen required that I use a different and very unnatural grip.
I snapped back, "I've had just about enough of this! You all seem to be forgetting that I'm a man. I'm only dressed this way to save my job!"
Nancy came over to me. She slapped me. I was shocked. She took me by the hand and marched me across the lobby and out of the hotel. We were downtown and the streets were filled with people. As some of the men passed they leered at me in a predatory way. The women looked at me coldly. There were some hookers standing there and they eyed me as if in the appraisal.
"You just settle down right now Missy," she said, "I want that account, and you had better do what it takes to get it or I will notify the home office that you have been fired and the hotel front desk of the same thing. You will have to check out of the hotel immediately Missy. Are you really ready to be kicked out of this hotel dressed as you are right now? How long do you think you would last out here on these streets?"
I was terrified at the prospect. I didn't even have enough money to buy a plane ticket home. I begged Nancy to forgive me and I told her that I would do anything she asked. I was almost in tears before she finally relented and said, "That's better Missy, You just do as I say and everything will turn out just fine."
We went back into the hotel and back to the seminar. If I had misgivings before I was really stirred up now. This thing had gone way beyond my dressing up for a day or two. I was being feminized by Nancy.
I could see that now. Some of the changes she was making to my body were permanent. I began to suspect that she had other motives.
Something else was disturbing to me. I was beginning to like being Missy. A big part of me was looking forward to being dressed up in beautiful long hair, a dress, heels, and hose, and going out on a date with a handsome gentleman. I wondered about what would happen at the end of the date. When I thought about it I imagined my date kissing me goodnight as he pulled me close. I imagined his hands caressing my plump, round, rear.
I suddenly realized that I was very aroused. Nancy noticed and frowned in disapproval. I had to pull in my stomach and arch my back so that my hard cock would not show through my skirt.
I was glad when the afternoon session was over and we went up to our rooms. "Don't get too comfortable Missy," said Nancy. "You and I have a little shopping to do before your date. You're going to need some help with your girlish figure and I know just the place to get what you need."I touched up my makeup in front of the mirror before we went out. As I sat at the vanity I could feel my silky pantied rear and I marveled once again at how serious women's clothing was. Soft and sleek. Cool and airy. Nylon and lace.
Nancy came to my door to get me and we were off. We got into a cab and Nancy gave the driver an address. We drove for a few minutes and then pulled up in front of a little shop. In the window, there were Mannequins in lingerie, one in a pretty black maid's uniform, and girdles on torso displays. The sign said DuPrissy Lingerie Shoppe. We entered the shop and when we did Nancy spoke for a moment to the owner, a tall, buxom brunette, named Rene. After a moment Rene went to the door and put a closed sign up. I was informed that I was to have a private fitting. I followed Nancy and Rene to a side of the store where there were comfortable chairs and many mirrors. Nancy sat down but indicated to me that I should remain standing.
I took off my jacket, skirt, and blouse and pantyhose then Rene began to bring me what seemed like an endless procession of foundation garments. Nancy sat in a chair and had me model each item for her in front of the mirrors.
I tried on waist cinchers, all in ones, longline bras, and girdles of every description from panty girdles to old-fashioned Playtex longline girdles with zippers up the side. But as I tried on each new garment Nancy always said, "No, try something else." Finally, we seemed to reach the end. I thought that Nancy would pick one of the girdles I had tried and make me wear it. But no. "None of those will do Missy." She turned to Rene and said, "I guess we will have to try a corset." Rene went into the back of the shop and then brought out a red satin corset with long garters. It had heavy boning and didn't look to me like it would be too uncomfortable. Little did I know. I raised my arms above my head and the owner began to lace me into my corset. I got the hooks in the front closed. The corset was very tight and as she laced up the back it got much tighter. I could feel a shallowness when I tried to breathe. She continued to tighten the laces and the pressure became intense. Finally, she seemed satisfied and tied off the corset laces. Her hands lingered on my pantied rear for a moment. When I looked in the mirror I saw that I now had a narrow waist and a woman's wide hips and protruding ass. As I got dressed I noticed that I could no longer bend at the waist but had to daintily bend at the knees to reach the floor. When I tried to walk my hips swung wide. It was the most natural motion for me now in the tight corset.
"Now Rene," said Nancy. "We need something for her top. Poor Missy is not very well endowed you see. Panties won't do for padding if your date holds you close Missy."
"I have just the thing," said Rene and she reached into a case and removed several boxes. First, she handed me a pink underwire bra to put on. I was alarmed as it seemed to be a C cup bra. Even I knew enough about bras to know that that was a bit large. I was really shocked when Nancy came up behind me and unhooked the bra I was wearing in front of Rene.
"Never mind Missy, said Rene, "I've seen girls of all shapes and sizes." She and Nancy began to laugh as if at some private joke. I put on the bra that Rene had given me and then from another box Rene took out a pair of silicone breast forms. She brought them over and fitted them into my bra. As they warmed to the same temperature as my skin they quickly started to feel real. As I walked the jiggled provocatively. They had very prominent nipples.
"There's just one more small detail," said Nancy. She held out a lycra brief to me. "Go into the dressing room and put this on under your panties," she said, "we don't want any repeat performances of this afternoon Missy. Now, do we?"
No, I did not. I went into the changing room and took off my panties. I pulled the lycra brief up my smooth legs and when it was pulled up and I was all tucked in I put my panties back on. I was amazed at how feminine it made my body, and the feeling of my nylon panties sliding across the lycra on my butt every time I moved along with the jiggle of my breasts was incredible.
I sat down to put on my stockings. In my corset, I had to sit very straight. I pulled on the nylons and attached the garters. I loved the way my legs felt in the nylons. They were so much more fun than pantyhose.
When I put on my skirt I was amazed at how easily it fit, I had to use my belt to pull it in a little. When I turned in the mirror I saw that I know had the hips and rear end of a woman, large and round with a narrow waist. My tummy was flat and my skirt fell so as to give just a hint of the feminine "V" it concealed. I now had breasts that were much larger than before and seemed to really be a part of me. My nipples showed through my blouse and I blushed as I closed my jacket over them.
Nancy and I said goodbye to Rene and she hugged me. "Come back anytime honey," she said.
After another short cab ride, we were back at our hotel. Walking through the lobby with my round hips swinging wide and my breasts bouncing was a new experience. I had to work to keep from being too wiggly. Men were turning their heads and Nancy was smiling broadly at me.
When we got in the elevator she said to me, "You had better learn to control that sexy body of yours Missy. You were driving the men wild with your 'Jayne Mansfield" walk'."
I was shattered. Now even my own body was starting to be beyond my control.
We went to my room and I took off my jacket, blouse, and skirt. Nancy brought the little black dress from the closet. I slipped it over my head and it just fit. It had a rather high neckline in front and back but was flirtatiously short. The hem just covered the tops of my nylons. My breasts were large and round and my nipples were there for anyone to see. I put on my black pumps and then Cathy did my makeup for the evening. She just added a bit to my look from the salon and made my eyes much more dramatic for the evening. Shelly came into my room and sprayed me with some heavenly perfume. She handed me a small beaded bag and when I looked inside I found makeup, tampons, and condoms. I looked up at Shelly but she just winked at me. I blushed crimson red as I snapped the purse closed.
There was a knock on the door and I heard Nancy talking to someone.
"Missy, your date is here," she called out. Shelly and Cathy went into a frenzy of primping and fussing over me. Finally, they stood back and I went to meet my date. He took my hand gently as I entered the room and then held the door for me to leave.
"Have a good time you two, and don't worry about having Missy in too early. Tomorrow's seminar starts late so she can sleep in," said Nancy.
My date put his hand on my waist as we walked to the elevator. He told me he understood if I was a little shy and didn't talk much. He told me he could talk enough for both of us. We went to a romantic restaurant for dinner by candlelight. He ordered us an expensive wine and after a few glasses, I began to feel warm and fuzzy. I began to lean closer to him as he talked.
After dinner, we went to a nightclub and he asked me to dance. When I pressed my breasts to him during a slow dance he held me close for a moment and I could feel his hard cock pressed against me.
We drank and laughed and danced some more and soon it was late and we were on our way back to the hotel. In the back of the cab, we kissed in the dark. He was very patient and gentle with me and I felt like a woman in every way. I touched his firm rod with my dainty hand. He was huge. I wanted to be his woman.
We went upstairs and to the door of my room. He asked me if we could see each other again the next night and I nodded my assent demurely.
He took me in his arms and we kissed again but then he said "Good Night, Missy." I was shocked. I was almost ready to ask him if he wanted to come into my room when he turned on his heel and was gone. I opened my door with trembling fingers and went inside. I sat at the vanity and looked in the mirror. There was no trace of my male self there. There was only a pretty, somewhat bewildered woman in a black dress. The other women heard me come in and began to filter into my room with a million questions. They helped me undress and Nancy unlaced my corset. I put on my nightgown and we all sat around and talked. I told them about what had happened.
"He's just being a gentleman honey, you don't see that every day," said Shelly.
"That's right Missy," said Cathy. "Besides are you the kind of girl who sleeps with a man on the first date?"
"I think she is," said Nancy with a sneer.
I didn't know what to think. I had never been attracted to men before. Why was Missy falling in love with one?
I took off my makeup and applied some lotion to my hands. Cathy and Shelly said goodnight and went back to their rooms to go to bed. Nancy lingered in my room.
"Come with me Missy," she said. I arose in my marabou slippers and followed her into her suite.
We sat and she made us a drink and she began to speak. "I know you expected more from your date tonight Missy. I am sure you don't really understand why. I know your date well and I can assure you that your second date won't end like the first."
"Missy, do you have any idea what might happen then?" Nancy asked me.
I had to admit to her that I did not. I had an idea but it was a murky thing that was not filled with much detail.
"I'm going to help you get ready," said Nancy. "Go get into my bed."
I did as she told me and curled up in her big bed in my short chiffon nightie. Nancy turned down all the lights and went into the bathroom.
My head was spinning at the events of yet another day in dresses and my old self seemed far away. I was having trouble even remembering his face.
I saw the bathroom door open and in the split second before Nancy shut off the light I could see her silhouetted in the doorway. She had something like a harness around her waist and as she turned I saw a long shadow. The light went out and she came to bed.
Nancy began to kiss me. As my eyes adjusted to the light I could see that she was wearing a latex dildo. She guided my head down to it until I had the tip in my mouth. Nancy had me suck her latex cock. As I was doing that she had begun to lubricate my ass. "I want to be the first in your sissy pussy, Missy," she said. She began to work her fingers in. First one then two. As I relaxed it started to feel good. Nancy had me move to the center of the bed on my back and then she put a pillow under my hips. She took my ankles into her hands and raised my legs up into the air and there I was, in a position of total submission to her.
She began to enter me, slowly at first. I did not think I could take it and I started to whimper a little. "Be quiet bitch," said Nancy.
"Women go through this every day so you had better learn to like it."
With that, she pressed deep into me and I let out a little cry. Tears were running down my cheeks as she moved in and out of me, pushing deeper with each thrust.
But soon the pain was replaced by something else. I started to enjoy what was happening to me. I began to thrust my hips up to meet Nancy as she drove her cock deep into me. Nancy stopped and pulled out and had me get on my hands and knees. She entered me doggie style and began a series of thrusts that drove me wild. She would slowly pull her cock almost all the way out of my grasping sissy pussy and then drive it deeply back into me. As she did this she reached around and took my cock in her lubricated hand. She began to stroke into me in unison with her hand moving up and down on my hard cock. Soon I was crying and laughing and babbling my head off as Nancy rode me into the night. The last thing I remember before drifting off to sleep was Nancy inserting a tampon into my sissy pussy. "Just to remind you of me, dear," she whispered in my ear.
After my night with Nancy very little of my former life as a man seemed to remain. I got up in a daze late in the night and went back to my room. I slept fitfully and dreamt of Mr. Catch holding me close and kissing me. But in my dream when I pulled back from his embrace he had Nancy's face. In the morning my bottom was a little sore but I had a golden glow all over me. Nancy had brought me to orgasm after orgasm. She had played the male role and did not allow me to assume anything but a female posture during our night together. I had been swept away by the ecstasy she brought me and the remaining male parts of me seemed to have been swept away as well. I was her woman in every way now.
I sighed and got out of bed. I looked in the mirror. My beautiful hair was a mess. But it was long and blond and curly with pretty highlights.
I brushed my fingers through it and saw my long red nails. They made my hands appear thin, delicate, and feminine. A long gold earring hung from each of my pierced lobes. Even without makeup, my face was very feminine with its thin high arched plucked brows. Just enough residue of my lipstick remained to make my lips pink and kissable. I could feel the tampon in my bottom and true to what she had said it did remind me of Nancy.
I hated the way I looked, but not because I looked so feminine. I hated the way I looked because I was so disheveled. I wanted to be pretty again and I set out to do just that.
The seminar sessions didn't begin until almost noon so I had plenty of time. I decided to begin with a long hot bath in my room's huge tub. The hotel had provided some sweet-smelling bath oils and I put all of them at once into the steaming water. I pinned up my hair as best I could, took off my panties and nightie, and slipped into the tub. The hot water was divine and as I soaked I felt like I was drifting on a cloud. I soaped my legs and shaved them, taking my time. There was not much hair to shave after my leg wax at the beauty parlor the previous day but my pubic hair was still quite shaggy and wild. I lathered it and shaved it. I kept making errors as I tried to even it out and by the time I was finished only a small triangular patch remained.
I luxuriated in the hot scented water and began to lather my body all over. As I lathered my breasts I lingered on them and my nipples became erect. I have aroused again but in a very relaxed and dreamy way. I could not help but touch myself and almost before I knew it I was orgasming again. What was it about the newfound femininity that had left me so sexually charged? It was almost as if my libido had been transformed as well as my appearance.
I was almost drifting off to sleep when Cathy came into the bathroom. She did not speak but just held out a big fluffy pink towel. I stepped from the tub and Cathy wrapped the towel around me. Not around my waist as a man would, but around my bust as a woman does. I smiled at Cathy and she returned my smile and gave me a peck on the cheek.
"Poor Missy," she said, "I'm sure that you are just a bit bewildered by now."
I was amazed at how perceptive she was, and how tender. She really seemed to understand the state that my mind was in. I started to talk and soon was spilling my guts to her telling her everything that had happened to me. About how I was starting to love dressing and living as a woman. My cab ride and oral violation the first night. My night with Shelly. My innermost feelings about my date with Mr. Catch.
And, most embarrassingly, about my night with Nancy. Cathy just held my hand and listened to me. When I described my night with Nancy and I got to the part where she had stripped away my manhood a single tear fell from my eye. Cathy wiped it away.
"Missy," said Cathy, "I really do understand what you are going through, probably a lot more than you think I do. I know what, we have a couple of hours before the session begins, let us go shopping. That will perk you up. But no business suits. I have some clothes you can borrow."
Cathy went to her room and returned with a cute pink silk pantsuit. I put on my panties, bra, and adjusted my breast forms. I put on my pantyhose and camisole. I put on the pantsuit. I loved the way the silk felt against my skin. It seemed to caress my whole body in a feminine sheath. Cathy sat me down and did my makeup. By now I was doing some of it myself but not as quickly or as well as Cathy did.
The only shoes I had that matched where the pink 4" heels. I put them on and looked in the mirror. I was a vision in pink. I was so glad that Cathy had not made me wear my corset.
We went to the lobby, got a cab, and soon were at the mall. We spent the next two hours talking and shopping up a storm. It seemed like every store had a pretty dress that Cathy or I had to try on. We looked at pairs of lovely shoes and giggled as we compared pretty panties at Victoria's Secret. At a huge stand selling earrings, Cathy bought a pair for me as a gift. They were delicate gold chains with a tiny heart dangling at the end. She bought the matching ankle bracelet for me as well and even clasped it around my ankle.
We visited all the makeup counters in the department stores and I found I couldn't choose between what seemed like hundreds of colors of lipsticks. I wanted them all! When I told Cathy this she smiled and a sparkle came into her eye.
"Just like a woman," she said.
All too soon it was time to go back to the hotel and to the afternoon session of the seminar. We carried our bags out to the taxi. I was walking much easier in the white flats I had bought at the shoe store. Cathy had loaned me the money.
We returned to our hotel and went upstairs to change. I took off the pink silk pantsuit but hung it in my closet instead of returning it to Cathy. She had told me to keep it in my closet for now.
Nancy came into my room as I stood there in my panties and bra. She came over, and after glancing at the door to make sure we were alone, she took my chin in her hand and she kissed me.
"I'll help you with your corset Missy," she said. She held out the red satin garment to me. Nancy laced me into the corset and it was even tighter than it had been before.
"Oh yes," she said into my ear, "tighter and tighter as you become corset trained Missy." Finally, she was finished. I could hardly breathe and I wasn't sure I would be able to sit down. Nancy ordered me to bend as best I could in my corset and remove my tampon. When I was done she handed me a new one and waited while I inserted it. I was terribly humiliated to have to do this in front of Nancy but she just waved my complaints away.
Nancy helped me attach stockings to the garters of my corset and then slid my camisole over my head.
She brought my other suit from the closet. This one was different from the one I had worn the day before.
It had a long flowing pleated skirt that came to just below my knee.
The blouse was pink satin with a big floppy collar tied into a bow. The jacket was long and cut like a smock. I put it on and then my 2" black pumps a few gold bracelets and some rings and I was ready to go. A glance in the mirror showed a very chic me looking back. A little less formal than the suit I wore the first day but although it was very feminine the look was all business.
Just before we left Shelly came in with a pair of women's glasses. They were styled with very large lenses. Shelly gave them to me and when I put them I found that the lenses were just glass. I looked in the mirror and now with my glasses and chic suit, I was every inch the career girl. I squeezed Shelly's hand and whispered, "Thanks."
We went downstairs and just as we were entering the seminar Mr. Catch came over and took my hand. He kissed me softly on the cheek and said,
"Hello, darling. You look lovely this morning." He told me that he would be working late but wanted to get together after for drinks. I murmured my pleased assent. I could feel my tampon as my sissy pussy spasmed in anticipation of the night ahead.
We sat through the session and then as the seminar started to come to an end we broke up into smaller groups. Every time we went to the ladies' room Nancy handed me a new tampon.
Nancy took me with her into a room where a group of businesswomen was meeting. Even though there were not that many women in attendance at the seminar, once they were all in one room it was a pretty good crowd of 30 or 40. I was accepted by them as a woman, although a few of them did look at me a little strangely. I would see them whispering amongst themselves and looking at Nancy and me.
We talked and networked. I got lots of compliments from the women on my nails and hair. I told them all about the little shop in the lobby and Miss Gilda. Soon a group of us moved to the bar for cocktails. The seminar was formally over now. In the morning we would all be returning home. The thought of it made me sad. I started to drink a little too much.
Soon we were all laughing and having a ball. The drinks were flowing. When some of the girls began to demand that we go to a club I was glad to go along. By now Cathy and Shelly had joined us and we were all in a happy mood. About six of us jumped in a car and several other cars filled up the same way as our party was on the road. After only a few minutes we arrived at the club. It was a strange sight though, only women were in line at the door. As we got out of the cab and I looked more closely at the club I could see why. It was ladies' night, and the entertainment was to be male strippers. I wasn't sure that was what I wanted to see but I was taken in the arm by Cathy and Shelly and marched into the dark bar.
Cathy argued and insisted with the Hostess and soon we were seated in the front row. The bar was filled with women from the seminar and being surrounded by so many friendly faces made everyone even more raucous.
They began to chant for the dancers and when the lights went down and the music began the crowd exploded. The first dancer was dressed as a cowboy but he didn't have any pants on under his chaps. I was almost knocked over when a woman rushed the stage to put money in his skimpy briefs.
As the show went on I found myself drew in and began to yell a bit myself and once I even put some money in the jock of a long-haired California surfer type as he danced in front of me. He winked at me and ground his hips in my direction as I put the bills in and I loved it.
The last dancer of the evening was a hunky Latino in a Zorro costume. Just as he began his act I felt a hand on my leg. It was Cathy. She glanced at me and smiled as she moved her hand up my thigh. She reached for my panties and moved them down. She began to caress my cock. It was very hard and stuck up out of my skirts as she kneaded it lovingly.
I was having trouble maintaining my composure. The hunky stripper, my feminine dress and role, and Cathy's hand were all making me wild. Just when I thought I couldn't take anymore the dancer moved to the other side of the stage. The lights suddenly were shining on us as we sat at our ringside table.
First one then another, then soon all of the women on the other side of the stage could see what Cathy was doing under the table.
They could see what she had in her hand.
The dancer saw too and began to dance towards me in a very suggestive way. The women were shrieking with delight now and as they did I orgasmed with more power than I ever had before. I spewed white cum all over and even reached the edge of the stage with a few drops.
I thought I would pass out for sure this time. Everything got very hazy. When I regained my senses Nancy was hustling me towards the door.
Women were patting me on the back and telling Nancy how much they loved her little surprise. Others were shouting "Where can I get one like that honey?" and "Your boyfriend is so sweet."
Nancy got me to the street and to a cab and soon we were back at the hotel. I had never been so humiliated. After all the things that had happened to me since I got off of the plane, this was the one that really broke my spirit. To be exposed, in front of all those women, as a man in a dress. It was just too much. Nancy held my hand and said soothing things to me. She told me that the women would keep my secret.
She had told some of them beforehand that I was a transsexual, so even though I had male organs, they thought of me as a woman.
Almost before my tears were dry Nancy took me to her bed and made me submit to her again. I was too weak to resist as once again she pushed her strap-on dildo deep into me. Afterward, she held me and gently kissed me for a while.
Soon we got up and I went to get ready for my date with Mr. Catch. Nancy pushed a tampon covered with lubricant into my sissy pussy. I hoped I could hold it in. he said I would find out later what it was for.
I decided to wear the pink silk pantsuit that I had borrowed from Cathy.
But even though I was wearing pants Nancy made me leave my nylons on and also made me wear my 4" pink heels. She touched up my makeup and put my hair up in a semi-formal way. High on top held up with pins and lots of loose tresses falling down.
A soft knock at the door and my date had arrived. He took my hand and kissed me lightly. He stepped back and looked at me and said, "Missy, you look good enough to eat."
"Well honey," said Nancy, "the night is still young."
We left and went to the bar. My date could see I was a little down about something and began to entertain me with little jokes and stories.
He complimented me over and over again. Soon I was feeling better. We decided to leave the bar and went to a club to dance. We began barhopping. My date seemed to know every little hole in the wall dive in town. We had been in one place for a few minutes before my eyes adjusted to the light. I looked around at the crowd but something wasn't quite right.
Then it hit me. All of the women were men. Some of them were quite beautiful and some had breast implants and were flaunting them in low-cut dresses. My date was sitting very close to me now and as he looked in my eyes he said, "I think you should know that Nancy told me all about you. I know your little secret. I don't care. In fact, you are the woman of my dreams."As he said this his hand had gone onto my silk pants. His fingertip had come to rest just on the outside of my sissy pussy. He applied just enough pressure there for me to feel it.
I started crying then as he kissed me deeply. I melted into his arms and we kissed again. Hidden by the booth we were in he pushed one of his fingers deep into me.
"Let's get out of here," he said. As we walked from the club he held me close and one of his hands caressed my rear possessively. In the cab, we could not keep our hands from each other as we kissed. My nails lingered over his hard cock and when I lowered my lips to it in the dark he shuddered.
Back at the hotel, we went to his room and again I melted in his arms. We sat on the bed and caressed and he began to slowly undress me. He took off my pantsuit, bra, and breast forms and began to kiss and nibble on my nipples. I held his head to my breast and cooed. He pulled down my panties and gently pushed me back onto his big bed. He kissed and caressed every inch of me. He began to probe into my sissy pussy and when he found my tampon he pulled it out. He took my cock into his mouth as his fingers went deep into me. He couldn't wait another minute. His strong arms were around my waist and then my legs were spread wide as he entered me. My sissy pussy was wide and waiting. The lubricant from the tampon had made me that way. Even though his cock was huge it slid in easily and I began to moan with pleasure immediately.
We made love far into the night and each time was a new phase of ecstasy. He was gentle but all man. He made sure I was satisfied over and over. He filled me deeply and made me beg for more.
Morning came all too soon. I gathered my clothes and kissed his sleeping forehead as I left to go back to my room. I felt something dribbling down my leg. It was my lover's cum. I put in a tampon as soon as I reached my room.
I sat down at my vanity and looked at the woman in the mirror. I was lost in thought when the phone rang. It was the front desk, calling for my male self. They didn't recognize my soft feminine voice as the one they were seeking. They told me that some luggage had been found. Should they send it over to the hotel?
I told them to forget about the whole thing. The gentlemen in question had checked out.
Epilogue.
Eleven months, three weeks, and 5 days later my heels clicked smartly on the floor as I walked down the corridor to Nancy's office. My breasts ached as they jiggled but at least the soreness was mostly gone now. In the three months since I had my implant surgery, I had not been able to really enjoy my new breasts but now I was feeling much better. And what better place to show them off than at the seminar in a new, sexy, lowcut outfit. I was on my way to a meeting with Cathy, Nancy, and a new employee who would be joining us this year.
Shelly has gone on to become supervisor of our northeast division. I have been promoted to her old job. I still see Mr. Catch whenever he comes to town. He spends the weekend and we sometimes don't wear a stitch of clothing the entire time except for me modeling sexy lingerie.
Cathy had to take a leave of absence this year. She had major surgery. It wasn't until we became roommates after last year's seminar that I found out something about my friend Cathy. She was a pre-op transsexual. Now she is a woman. The same thing I will be after my surgery this year.
Nancy keeps tormenting me and putting off the date. She says Mr. Catch likes me the way I am. And by the way, we did get his account.
The meeting began and we all had our luggage ready as per Nancy's instructions. If our new employee was wondering why he had to have his luggage ready the day before the flight he didn't say anything. Just as I hadn't said anything the previous year. I saw Nancy sizing up his bags. She even took a Polaroid of them for reference when no one was looking but me.
As we were chatting he asked, "What should I wear on the flight?"
"Oh, something casual," I told him. "You will have lots of opportunities to dress up at the seminar."
We ladies all laughed.
The End.
Comments
J Chimera
A truly great hot story! Loved it.💓
Natasha
Great story feminization turns into enjoying being a girl and feminine desires
Brianna Demonet
I would like another part,as always LOL! One nice long one with another seminar adventure and to see how Cathy, Shelly, Missy and Nancy are doing. Of course to see about any new recruits.
Brianna Demonet
Very hot story i loved it.
Randy linders
❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️💋
Julia Miller
Happy ending for another great story. Our heroine Missy came through her forced feminisation with flying colours. She got the man of her dreams and for Missy, it really wasn't forced at all, as she enjoyed the journey from a shy young man, to an outgoing beautiful woman all in the time for a 2 day seminar. Amazing! I especially liked the twist at the end of this story!
