Becoming Paula

I work in an office with 15 coworkers about 11 of them are women. I get along well with my coworkers and go out of my way to be helpful. I find it is more fun to work with friends than to work with strangers. My name is Paul and I work in an insurance claims office processing claims and making recommendations for our supervisor who signs off on the claims. In the office I am well respected and enjoy my coworker’s support. There is nothing I would not do for the people I work with. I also help my coworkers with their workloads when we are swamped, as I am a fast, accurate worker. I only wish that support extended to my life away from work.

I am basically a lonely guy once I leave the office. I can’t seem to impress women with my masculinity. I am 25, 5" 4' and about 115lbs with dark auburn hair and green eyes and I don’t cut a dashing figure, my voice even betrays me. My coworkers are more likely to refer to me as somewhat pretty, rather than handsome or dashing.

The “girls” as I call them at work often lunch with me. It is hard to believe but they treat me like one of the girls, and they involve me in their “girl talk.” You know what I mean they talk about clothes, makeup, sex and guys around me they will even elicit my opinions, but let some other guy sit down with us and the timbre of their conversation changes. They are more than somewhat protective of me from guys who use to poke fun at me. There is even a mother figure named Ginny, we all love her, she is about 38, and leads the “girls” in an assault against anybody who would torment any of us. She has read the company harassment riot act many times. Things settled down since I have proven my value and gained their respect or at least they fear the wrath of Ginny.

Our supervisor Charles encourages us to get to know each other when times are slow and anytime we are on break. The “girls” would often ask about how I was doing, my love life and family and such. It was easier for me to smile and lie saying things were great, and such.

Come 5:00 p.m. though I have to face the world and leave the protective environment of my office. I have tried dating services and singles bars. Nowadays I just save my money and drink at home, not that I drink all that much. In my off times, I often go to the mall and just walk, just to be around people. I have found that there are a lot of people doing just the same thing.

Things began to change though, when I was at the Mall one Saturday afternoon. I had stopped outside on shops and looked up at the mannequins in the window, not really seeing but just out of rote. That is when I heard, “Oh Paul” called out. I turned and saw Ginny and two of the “girls” Barbra and Rachel come rushing to me. I waved at them and we exchanged hugs all around. They asked what I was up too and I said just walking around, getting a little exercise. Rachel jumped in and asked if I was window shopping. I said yes. I do a lot of that.

Barbra said, “oh really I bet you would look good in that.”

All three of the girls were giggling at that comment, and I was stumped until I turned around and saw that it was a dress shop we were standing outside of. I must have turned ten shades of red and I started to turn to escape but was caught by both arms and the girls said we were just kidding Paul, chill out dude.

Ginny said, “why don’t you come with us Paul.”

In this matter I didn’t feel I had any say in, because I was just whisked away arm in arm between Barbra and Rachel. They pulled me into the dress shop we were outside of they were like a pack of wolves circling carrion looking for the right morsel to eat. They picked several outfits each and left three purses on my arms as they went to the dressing rooms. They would model them for me then change and come out. This went on from store to store. I was even dragged into a lingerie store. They asked me what I thought about this and what I thought about that, luckily, they didn’t come out to model for me. I noticed that I got a lot of stares from the patrons there, especially since I had three purses on my arms. I wouldn’t admit it to them but I was enjoying being with them.

After about three or four more stores and carrying several bags for the girls, we wound up in one of the restaurants in the mall. I helped the girls with their chairs I really think they would have stood there till I did. They all three were looking at me as we began talking. Talking, they were grilling me. They asked why I was at the mall. I tried lying to them but they didn’t buy it. I finally broke down and told them I came there to be around people and that this is the type of thing I do with my free time. I told them that I had not had a date in three years and it was either hang here or hang at home.

Then I broke down and told them my whole story. When I first stated school, I was tall for my age. I was nearly 5 feet by the end of the second grade but my growth slowed down and even the girls started out growing me. From the third grade through high school, I grew a little more than 4". I was never very athletic, I didn’t run well, throw, or any of the things boys did. I was teased about my size and called sissy, fag and such. Even some of the teachers treated me poorly, but there were some teachers who were like Ginny who would look out for me without my asking, and some of the girls my age would also look out for me.

College wasn’t much better but there wasn’t as much physical harassment. I admitted that I couldn’t even get a date from the less attractive girls. If I had been a girl, I would have been a pretty girl. The only date I had during college was with Carla, a confirmed Lesbian. Carla was the masculine partner and I dressed as a girl the feminine partner, for a Halloween party for her sorority and nobody figured out I was a guy. Carla made a convincing guy and I made an even more convincing girl. The girls in the sorority liked me. When they weren’t hunting studs, they would hang around me. I was even asked if I would be interested in pledging the next semester (This broke up Barbra, Rachel and Ginny till they saw my reaction). That was my date’s joke on them. While I was dressed up Carla and I would make out, but just like Cinderella, at the stroke of midnight I turned back into Paul and she acted like she didn’t know me.

I hadn’t noticed but the tea we had for dinner had been replaced with Margaritas. I was on my third when I finished my story. I didn’t know why I had said so much, it was like a dam had broken and the girls had been so attentive while I talked.

Ginny broke the silence and said, “you really would have made a very pretty girl, I just love your face and eyes, what eyelashes you have. You were really invited to pledge that sorority?”

I said, “yeah one of the members even called me after they learned about the deception and asked me to think it over, but I think it was just to tease me. I am trusting you with this story please don’t hurt me with it.”

Barbra spoke up, “we would never do that to a friend and believe us we are your friends. Have you ever thought about becoming a woman?”

My face must have turned crimson. I could feel my face flush with heat.

Barbra saw my discomfort and said, “I am sorry Paul, please forgive me for asking. It’s just you seem so feminine at times and we are comfortable around you, it’s like your one of us.”

“I like all of you and there is nothing that will change that,” I said.

They giggled and looked at each other in a knowing manner. “We think you are a great guy to Paul, we enjoy working with you,” Rachel said, Barbra and Ginny agreed.

Ginny spoke up and said, “I don’t know about you girls but it is getting time for me to go.”

I picked up the tab for the girls, which I got a round of hugs and kisses and they got up and left. I was left wondering where all I could not believe I had talked so much. I have never told anybody, so much about me. I was afraid it would come back and haunt me, but I trusted them and hoped that they would not hurt me. At the same time it felt good finding someone to listen to me and seemed to care about what I felt.

Sunday came and went and soon it was time for work again. I arrived at work and it was like the previous week. The “girls” were no different from before and I was glad and it was good being at work. On Wednesday Sharon another of the girls came by and asked me if I would like to join a few of our coworkers for drinks on Friday after work.

I said that, “I should be able to make it.” I have gone out with them drinking on Fridays before it was no big deal. It was a labor day weekend and we were closed on Monday and I didn’t want to be alone on the start of it.

Friday came and the day just flew and we were headed to the local watering hole.

Sharon said, “I took the bus Paul, I was wondering if I could ride with you?”

I told her, “I would be happy to give you a ride and glad for the company.”

When we got to the bar there were about ten people from our department there. I didn’t drink much seeing that I would be driving Sharon and myself home. After a couple of hours the crowd from work was dwindling down until it was just Sharon and I.

We left at 10:00 p.m. and I drove her home. I parked outside her place and she asked if I would walk her to her door, there had been some late night assaults in the area. When we got to her door, she invited me in for coffee. I thought that this was my lucky day, I had not thought of Sharon as a possible date, but my prospects were looking up. Inside she led me to her kitchen and started a pot of coffee.

Sharon said, “I will be right back, I need to visit the lady’s room.”

I sat at the breakfast bar and watched the pot perking. Then I heard feet coming back to me. I turned and there she was standing there with about seven other girls from work.

I could not but wonder what was going on. I honestly nearly wet my pants, behind Sharon were Barbra, Rachel, Ginny, Peggy, Donna, Marcy, and Carol. Sharon poured coffee for us. I was surrounded.

Ginny approached and said, “we thought about what you told us and we want you to understand we would never hurt you, you are such a sweet guy.”

Barbra came over to me and put a pill and a glass of water beside me. She looked into my eyes and said, “Paul, we want to have fun with you till Tuesday. If you are agreeable, we want you to take this pill, it is a sedative and you will be out for about six hours. We want to do something to you, if when you wake you don’t feel it is right, well no harm is done. If you like what we do then we could really have some fun. We don’t want to tell you what we have planned but we promise you that you will not be hurt and nothing will be done that cannot be undone. You are a very important person to us, and nothing will change that.”

I sat there for a second looking at that pill and thinking, these girls were my best friends I had. Did I trust them enough to turn myself over to them? Would I like what they would do to me, what would they do to me? Deep down I thought I already knew the answer to those questions. I remembered almost every word I had said to them and I had enjoyed being with them then.

I asked Sharon where her bathroom was saying I wanted to think for a few minutes. She took me to her bathroom and left me there. I emptied my bladder and took care of the other business there. I then looked in the mirror above the sink as I washed my hands. I opened her medicine cabinet and saw an unopened toothbrush I took it and brushed my teeth and found some mouth wash to rinse with. As I turned to leave, I saw a satin robe hanging on the door and decided to test my conclusions. I took all my clothes off and neatly folded them neatly and put the robe on securing it around my waist with the robe’s belt. I was a little frightened, but I picked up my clothes and headed back. There were a few gasps and giggles as I approached the girls I put my clothes on the table and picked up the pill and water and took it.

“Now what,” I asked.

The girls all had big smiles on their faces they all hugged me and kissed my cheeks. They led me to the bedroom and had me lay down.

Barbra asked, “so you think you figured it out don’t you?”

“I think so, but I am not sure,” I told them. “I hope you don’t mind me using your robe Sharon, and I owe you for a toothbrush also. I wanted to freshen up before you girls did whatever.”

Sharon said, “that’s fine you just made our job much easier and that it looked good on us.”

I could see the girls getting ready as I started to get drowsy. I told them that it wouldn’t be much longer. It had been about 20 minutes since I had taken the pill. Barbra came over and held my eyelid open and looked at me, and then there was nothing.

I woke up a little groggy no longer on top of the covers and not wearing the robe. I felt a weight on and pressure around my chest, my legs felt smooth and my penis felt a little uncomfortable. There was a girl on either side of me sleeping. I carefully maneuvered my self out from between them without disturbing them.

I stood and notice I was wearing a long sleeve pastel silk sleep shirt that was tickling my skin. I saw that I apparently had tits, saw that I had long red fingernails and felt that all my hair below my ears was gone. I tiptoed into the bathroom and pulled the sleep shirt up and a pair of panties down and another panty of sorts that restrained my penis between my legs. I sat down and peed. Tucking my penis back, I pulled the panties up. I stood in front of the mirror and pulled up the shirt and saw a pastel yellow satin and lace panty and bra set with silicone breast forms.

I left the bathroom and saw the rest of the girls sleeping on the floor and on the couch. A clock on the wall said 4:35am. I worked quietly and started a pot of coffee. I was on my second cup when Sharon came into the kitchen moving groggily.

“Morning Paula, you are up early this morning. How did you get out of bed without waking us?” Sharon asked.

“I was careful I didn’t want to disturb any of you,” I replied, “you all looked so tired.”

“Dang Paula. You should have been out for two more hours. So what do you think so far,” Sharon asked?

I started to reply when I finally noticed my toenails were painted a nice shade of pink that matched my nails, and said, “so far so good.”

Sharon came over and we hugged, she just held me there and whispered in my ear, “We love you, Paula, please don’t forget that please.”

My eyes were watering and a tear rolled down my face and I whispered back, “I know Sharon I love all of you.”

More of the girls started wandering in slowly and I got hugs and kisses from them. About 7:00 a.m. everybody was up and discussing what they did, and their plans for the day. Sharon and Ginny made us all breakfast and I made more coffee. At 8:00am the girls felt my face, it was very smooth. I told them I never had much facial hair. They had me sit down in a chair and had me take off the sleep shirt. One combed back my hair and put on a stocking cap carefully tucking stray hairs under it, and another, trimmed my side burns all the way off and two more started applying makeup. This went of for about 20 minutes. A wig with long auburn locks was mounted on my head and I was handed a black lace and satin bra and panty set. I unhooked the bra that I was wearing the girls giggled as I uncovered my silicone breasts. I pulled off the outer panty and pulled on the black panty and hooked the bra, a 36 B, without assistance. I was handed a long sleeve black silk front button blouse with black pearl buttons. This was a new experience because the buttons were on the left side and the long fingernails on my hands. I was handed a pair of off black pantyhose, which I stretched, and pulled them on. I was handed a padded girdle to give me hips and a pink leather mini skirt. I pulled the skirt over my hips and reached under the hem and pulled the hem of my blouse down. I buttoned the skirt and then zipped it, and smoothed the skirt down. It tightly hugged my bottom and the hem was about 6 inches above my knee. To complete my look I put on a pair of black patent leather pumps with a 3 inch heel.

I turned to the girls and strutted my stuff in front of them. I reminded them that I had done this before, even my voice was convincing. I moved to the couch and sat between Barbra and Sharon smoothing my skirt under me, knees together, then crossing my legs at the knee, to a round of applause and giggles. Several of the girls were saying how naturally I adopted to the role. I stood and walked back and forth for them and sat back in the chair head up and shoulders back, my chest out, knees together feet crossed at the ankles. A necklace, a lady’s watch, rings, and bangles came out next. I saw Peggy with a camcorder taping all of this, and I started to panic, but they assured me that it was ok.

They had me stand and introduce myself to the camera. I then walked around some more turning and posing for the camera. They hooked the camera up to Sharon’s TV and rewound and played the tape for me. It showed me on the bed sleeping and then showed my transformation step by step till they dressed me in the sleep shirt and covered me on the bed. It then showed me sitting in the chair and getting my hair done, my face made up and getting dressed, concluding with my little show. I had not seen them taping earlier but the transformation was stunning. I looked and sounded as good as the other girls. They then gave me the tape (I didn’t notice that the VCR was running in record mode but they were good to their word and never used it against me).

The rest of the girls started to get dressed for a day of shopping. I was handed a purse with some things already in it and a lady’s wallet which I place my credit cards, checkbook, and other things. I even put my driver’s license and insurance card in it.

I was going to have some fun I had a lot of money to spend since I was a very frugal spender and I was enjoying my self. I thought, too bad this is only a long weekend, but I figured I had a new hobby. I had not felt this good in a while.

We hit the mall with a vengeance it was not as bad as TV portrays it but we were on a mission. It surprised the girls when the first place I went to was a lingerie shop. The girls really enjoyed it. They had me try on so much.

Barbra brought me a corset with a full cup while I was in the changing room. She just marched in past the curtain and said, “you just got to try this on.”

The corset was a blue satin print with black lace. It had a hook and eye closure in the front and laced up in the back. I thought it looked like some medieval torture device. Barbra loosened the laces in the back and unhooked the front. After I took my bra off, she hooked up the front. I thought this wasn’t too bad until she started lacing the corset. I was in pain. The corset was taking my breath away. Just when I thought, it couldn’t get any worse it did. I nearly passed out. They took my 29" waist down to 25 inches. Ginny handed me a pair of stockings she had purchased Barbra had to help me to put them on as I could not bend to do it. She ran the garters through my panty and hooked them to the stockings. After putting my shoes back on and assuring my self that my manhood was still covered up, I pulled me out of the changing room. All the girls were there with a sales lady. I looked in a full length mirror. Something strange happened inside me as I looked at myself. I could not believe how good I looked. They had me turn around model it for them. I strutted my stuff, like a model on a runway. I received a round of applause and curtsied.

The girls said, “you gotta buy that.” I nodded and asked the sales lady if I could wear it out. She took the sales tag off and with a plier type device took the anti theft tag off. Barbra measured me with the corset on and I was a 36C-24-36 with it on.