Working on a small team in a large office with all women meant I got an insight into women’s lives that many men miss out on. Sometimes I feel like I’m missing the banter, but to be honest the without the constant competition when it’s all men, which let's face it can be tiring, so it was refreshing to work in a nurturing environment.

Although the talk about split ends does get annoying sometimes. I never ever got them in my hair and it was as long as some of the girls, I just didn’t put so much ‘product’ on it so it didn’t suffer as much.

Maureen, although she hates that name so we call her Mo, our manager came back from a meeting and sat down to give us all the good news from up high. There was never anything interesting in them so I would fade it out, until I realised she was talking about me. “What’s that?” I asked, hoping I was pretending I listened. She wasn’t fooled.

“They want to hold a beauty contest at the Christmas party and as the only man on the team that means you.” She said. There was nothing buff about me; I was short and skinny, with a geeks ponytail. “Huh?” I said.

Then she explained and all the girls were looking at me, even the ones that work at the other end or little bit of the office. It was a drag beauty contest. I told them I wasn’t sure, but secretly I was thrilled at the idea. I hadn’t dressed for 14 years when I was 8. It seemed so long ago and I just wasn’t brave enough or knew the right people to do anything about it.

Mo said the party was in seven weeks, so there was plenty of time to decide and that they would all help me. Karen, Pam, Sue and Laura who I worked closely with each leaped into pleas to get me to do it and that they would help me. I um’d and ah’d a bit and said yes I would but they would need to help me.

And that’s why on Thursday evening Karen picked me up at home to take me to Mo’s. I said bye to my flatmates but they were cuddling up watching a film and looking forward to some alone time tonight. I hadn’t told them what was happening, I couldn’t bare the embarrassment. Karen had several bags on the back seat of her car, which felt a bit ominous. She told me had some things for me and that each of them were bringing outfits for me to try out.

At Mo’s, her husband was out with their kids and we had until ten when they would be back. We went up to her bedroom, and Sue and Pam were there already, each with a bag of clothing. Karen was closest to my height and build so she had more with her. We dumped her bags and Karen opened one, handed me a pair of her knickers, told me to put them on and they waited outside.

It was a long time since I’d held them to put them on, and some of the old feelings came back, dressing up with the girl who lived next door, our parents laughing, and being so upset when she moved away and not having the dress up time anymore. I started to take of my clothes and pull the panties up. I tucked myself back but I still had a bit of a bulge. I told them I was ready and they came back in, looked me up and down with satisfied looks on their faces.

Pam said, “We need to lose the body hair.”

Laura, “And a better hairstyle as well.”

Sue, “And the bulge needs to go as well.”

They all went into the bags and Karen handed me a bra to put on. It matched the panties. Then it was all business, Mo and Laura started working on my hair and sorting out makeup. Karen handed me a pair of tights and I rolled them up to put them on. They were opaque and a little shiny and covered what little leg hair I had. When I sat back down, they carried on with my hair and Mo started to put some cream on my face. “Foundation.” She explained. I watched them in the mirror as Karen started sliding shoes on my feet to see what fitted. A pair of simple court shoes, about an inch high heel fitted me.

Karen said, “You’re a size five like me.” I looked at her a bit confused thinking, no I’m a seven. “Girl sizes are different.” She said. I carried on watching the transformation of my face and hair take place, amazed at what they were able to do. It was still me, but a way more feminine me. The make up and everything made me look like a young woman.

Finally they were happy and told me to stand up. Karen slipped something cold into the bra and I tried to back away from them, but they soon warmed up. “Breast enhancers. These are the big ones, I used them when I dressed as a Playboy bunny once.” Karen told me. I looked down and I had a shape now. In the mirror there was a half dressed female me looking back. She smiled. I was handed a skirt and I pulled it on back to front so I could zip it, and then twisted it around.

They looked at me in surprise this time. “I’ve had girlfriends.” I said, and we all giggled. Mo got a bottle of wine and Laura handed me a top. I carefully pulled it over my head trying not to damage the makeup of the hairdo they had given me. I never knew my normally lank hair could have so much body and feel so fluffy and light. I took a drink of the wine and saw some of my lipstick on the glass.

“Ok, lets see you walk.” Pam said. I walked like a fool and felt it. They spent the next hour making me walk up and down. Sit down and stand up, holding my glass and taking sips until they were reasonably happy. I was passed a handbag and put my phone in it. Mo put some of the makeup I was wearing it, and told me to empty my wallet into the purse as well, and put it in the bag with my keys.

There must have been a big siren at this point, but I missed it. We went downstairs and walking down them in the heels and skirt was something they hadn’t taught me, but it was obvious how to do it, turn slightly sideways and be careful. The reduced movement from the skirt did surprise me, but I made it. I did find myself admiring the skirt for the first time, knee length in a what I later found out was a tulip style so it flared out and hid the bulge in my panties. Karen was wearing a short bandage skirt that was really tight and I wanted to try it on. The bulge meant I wasn’t ready too.

When I got downstairs I was handed a jacket and helped into it. Now it started to dawn on me. “Karen suggested we go for a drink, so we are.” Pam said.

I said no. A big no! They told me they have hidden my clothes so if I want them back I’m going for a drink. I was trapped and had no choice. I didn’t want to bump into her husband or my flatmates dressed like this. I didn’t have enough money for a cab so was screwed. “Ok, but I want to feel safe so we go to a gay pub. At least I won’t get beaten up there.” I told them.

They reassured me that wouldn’t happen, they would look after me, but a gay bar would be fine. Mo said she’d never been in one before so it will be fun.

I sat in the car scared stiff. They kept talking to me and every so often told me to adjust how I was speaking. When I got out of the car and walked with them to the bar, I was scared, but talking more like a woman. In fact I was gabbling a bit with nerves. Plus already my feet were hurting. Why are the soles on girl’s shoes so thin?

We walked in the pub and ordered some drinks. Turns out on Thursdays there are a lot more lesbians in the bar than men, so we didn’t stand out. I am a guy so I was checking them out, I couldn’t help it, but I was also looking at how they were moving and what they were wearing.

We sat down and before long I had relaxed and we were just a bunch of girls out for a night in bar we wouldn’t be hassled in. Although a lesbian did come on to me at one point, and when I told her the truth she was really flattering in her compliments to me saying she hadn’t realised. She also told she was tempted but I should know she’s a top and likes using a strap on if I was interested.

“Can’t we just be friends?” I said and she laughed. She came back with me to our table and we all chatted away. Before long Mo, Pam and Laura had to go home, but I didn’t want to leave. Sue offered me her spare bed and I said yes. Then I remembered my clothes were at Mo’s and as neither Mo nor Sue worked on Friday, she offered to bring them round the next day. I asked if I could have the day off and she laughed and said yes.

The three of them left so me Karen, Sue and me stayed and drank having fun. The lesbian who hit on me, Kim, well her brother, Joe, came over now that there was space to sit and started talking to us and I realised he was flirting with me and because I was trying to act as feminine as I could, I was flirting back.

I went to the ladies and Karen came with me. I felt panicky about it and she calmed me down by saying that girls flirt with guys all the time, it means nothing. I told her it does to him as he might think he’s in with a chance. I went in a stall to have a pee and sat down, thinking nothing of it. After I wiped and stood up, I felt something happen down there. I looked down one of my testicles popped out of me. It didn’t hurt. I gently pushed it back up and it went back into me. I tried it with the other and it went in. I pulled my penis back and then the panties up and I was smooth down there. I’d discovered tucking by accident.

Back in the bar I was more relaxed but still a bit flirty with Joe. Karen had to leave so I kissed her cheek we said goodbye and me and sue carried on. Joe asked me for a dance and I said yes. I watched the other girls and just copied how they were dancing, it wasn’t difficult; a little hip movement, run you hands along your body and you’re doing a sexy dance. I kept flirting with Joe and his hands were on my hips, moving with me, sometimes behind me with our bodies moving against each other. I even rubbed my butt against him a bit as well. Then a slow song came on.

“It’s the last song.” He told me, as he pulled me close. I let it happen. As we danced I could feel him pressing against me. ‘You know I’m not a girl?” I told him.

“Yes, but it’s ok. I’m bi.” He said. Now I did feel scared. He knew what I was but still fancied me, and I could feel his hardness pressing against me. I tried to move away, but he was leading and when I did he moved with me to keep the contact. Finally the song ended and he gave me a kiss on the cheek, but as close to my lips as he could get. “Naughty.” I told him, but he took the opportunity to kiss my lips, just a peck on the lips really.

“Sorry, I couldn’t resist it.” He said with a smile as we walked back to the table. Sue was looking at me with a big smile. “He kissed me, I didn’t kiss him.” I told her, but he still had his arm around my waist and I wasn’t pushing him away.

When we left I hugged Kim and Joe gave me a kiss on the cheek again and I kissed his as well. He whispered in my ear that he hoped to see me again. In the car with Sue as soon as the door shut she told me she could see his erection when we walked back. I just laughed it off and reminded her that Kim came onto me as well.

I slept in her spare room and when I woke up realised I only had the clothes I wore the night before. I pulled the skirt and top on and went to have a shower. Back in the room I got fully dressed in last nights clothes and looked in the mirror. My hair was flat again and with no make up I felt a bit silly. I opened the purse and looked to see what I had. I’d repaired my lipstick and mascara in the pub, but this was starting from scratch.

I had some powder so I put that on and it seemed ok, then I put some eyeliner and mascara on, then the lipstick. My hair I just put in a ponytail with a band I found in the room, but put it further up the back of my head. I could hear someone moving about downstairs so headed down, following the smell of coffee. Sue’s fiancée was in there.

“Hi, you must be Steve, although maybe I should call you Sarah. I’m Ron.” He said.

“Hi Ron, and yes, I think like this Sarah makes more sense.” He got me some coffee and Sue walked in, fresh from the shower. She said I did an ok job on the makeup, a three out of five maybe, with an extra half point for effort. We sat and chatted with Ron and he already knew all about what I was doing. He didn’t look down on me or treat me badly in anyway. After he left for work Sue told he was a modern man and not an idiot. “If you were here as Steve he would act the same.”

We waited for Mo to turn up and just after half ten she got here. She came in with a bag and I wondered why she had brought one of Karen’s.

“Are mine in there?” I asked. She looked at me confused for a moment and said that Karen told her these were my clothes. I opened it up and it was all of Karen’s cast off she’d brought along for me to try. I collapsed on the sofa and they told me to put my knees together. I had no clothes; Ron was a lot bigger than me. Sue and Mo told me not to worry, I looked great and they can re do my hair and make up and not to worry.

I felt like a passenger in the conversation. They were going through the clothes and picking something for me to wear and discussing what to do with my hair. They sat me down and started working on me, but this time they explained everything and how to do it, even getting me to do some of it. Before long I’m joining in the conversation and asking questions. I was just being swept along by the tide and decided to swim rather that sink.

Just before midday they declared themselves happy with my look and we were going for lunch somewhere. Wearing a denim skirt and a jumper with a light jacket on, outside was freezing. I was happy to be in the car quickly. Mo and Sue had thicker coats on and felt sorry for me. Sue’s coats were so big on me (she’s taller and quite a bit larger than me), so the first stop was a shop so I could get something better. Thankfully my debit card only had my initials on it, so I got a coat and a pair of knee high boots to wear the rest of the day.

We went for lunch and had a look in the shops and seeing that I was now Sarah for the day, Mo told me more about the beauty contest.

“I really want to win this, we’re a much smaller team, and most of the others will have two people entering. There’s three parts to it, a career part where you dress as your characters job, the swimsuit and off course the evening gown, although they’ll accept cocktail dresses. Are you ok with that?” She looked at and I could see how much she wanted this.

“Yes. What’s the plan?” I asked.

None of the girls at work wanted me to be a drag queen, they wanted me to be as real a woman as possible. It would mean a lot of training and both Sue and Karen were happy to let me stay at theirs while I was Sarah. She’d booked the afternoon off for me the day before the contest to go to a salon and get waxed and my hair done ready for the day of the party. At three on the day I would go with the other entrants to get ready in the conference room and I could have help if needed. Then we would parade to the staff restaurant and after each section we would just mill for a bit before going to the next stage to make the whole thing last longer and get everyone involved in the fun.

I ended up staying at Sue’s again that night and going home on Sunday, with freshly shaved legs and armpits. I’d ordered one of those no-hair things advertised on TV to use on my face to get me as smooth as possible and not worry about a five o’clock shadow. I rarely ever got one anyway, but at least it should take away the hassle of shaving my face as well as my legs and pits.

Back at work, other than the team being happy I was going through with it, my girl team of Mo, Sue and Karen wouldn’t tell anyone any details until they saw it on the day.

On Wednesday after work I went to Karen’s with her and my girl bag with lingerie, shoes and some clothes. We got there before her husband Sid, so I got changed. Tonight was about being Sarah in front of someone new, and other than us going for a quick drink, nothing much happens. Sid was ok with the whole thing, he even said I looked cute which made me blush.

The most embarrassing thing was hearing them have sex when I was in the room next door. Sid was gone when I got up and got dressed as me, which I was pleased about; I didn’t really want to see him as me now. Karen apologised about the loud sex but Sid was horny and he always knows how to turn her on. I wondered if Karen knew that everyone at work knew about the sex tapes with both of them on the internet that showed her and Sid with other couples.

In the end as she was honest with me, I told her as we walked to the bus stop. Turns out she uploaded them as they are both swingers so she wasn’t bothered. They use the videos to hook up with new couples.

The weekend was meant to be with Sue again, but she had to go away so I was with Karen. In a way I was pleased as it meant I had access to a bigger wardrobe. I got changed and by now I was ok with doing my own hair and makeup. She told me we were going clubbing tonight and helped me with the smoky eye look. It was also the first time I had tried liquid eyeliner and after many attempt and removals finally got it right.

Sid came home, jumped in the shower as me and Karen were trying on dresses. I’d forgotten we were in their bedroom when Sid walked in with a towel round his waist. We were both standing there in lingerie, stockings and heels. I tried to cover myself but he told me not to worry, he’s seen me now so what’s the matter. And then he dropped the towel and stood there naked.

“See, there’s not a problem as far as I’m concerned.” He said.

Well there was for me! I was blushing like crazy and when I looked down the blush was over my whole body it seemed. Sid walked over to Karen and gave her a kiss, which turned into a much deeper one. When they separated his penis wasn’t so much hanging as growing a bit. Karen told me to ignore him and not pay any attention to the poser. It was hard to and I felt like he was taking his time on purpose to show off. His penis was impressive and I felt myself wondering about Joe’s when it was pressed against me.

Anyway, he finally put some Calvin’s on and I’m sure he got bigger before he walked out. She told me he was showing off for me, and I’m sure he was fully hard when he walked out. Karen and I had finally picked dresses and I went for a LBD and she went for a red one. My heels for tonight were a little higher than normal, four inches high. I’d been training in them for a while and tonight was the big test for them.

We got back from the club about three, and it was one of the best nights out I’ve ever had. We danced and Sid flirted with me and I flirted with him and other guys. The dancing was a repeat of me and Joe, except that Sid was running his hands over a lot and I felt worried for a minute, he is my friend’s husband after all.

Again I heard them having sex when we got back and in the morning Sid made no effort to hide his nakedness with me. He was playing football later so we went to watch; Karen told me I should wear flats. A could of his team mates were looking at both of us and laughing and I got really paranoid. He came over for a bit and I stifled my anger to ask him if he had told them about me.

“No, they know we swing and they think you’re a swinger as well.” He said. He looked hurt that I accused him of betraying me. “Oh, sorry.” I said. And then for their benefit I put my arms his neck and pulled him closer to me, intending to make them think we were kissing. What happened was we did kiss, I even opened my mouth a little and out tongues played lightly with each other. As we parted I looked him in the eye and said sorry. He smiled and patted my bum saying my pleasure. “Although a few on them will hit on you now, you realise?” He said.

Now I went really red. A few of them did but I gently refused their passes at me. In the evening we just went to the cinema and nothing else happened. I was getting a lot more comfortable being Sarah in public. Sunday I went home and my housemates had gone away for the weekend, so I was back to being me and relaxing. I need that time to get mentally ready for work and stop acting like a girl. The no-hair thing had arrived and when I tried it on my face it worked really well.*

On Wednesday I was back round Karen’s and putting on a short denim skirt with a sleeveless T-shirt when she told me what was planned for the evening. I was going to be surrounded by women and none of them would notice me at all. I had no idea what she was on about until we turned up a big pub that had a function room which we headed for. There was a poster saying it was male stripper night. I looked at her and felt confused. “Trust me,” she said, “you are going to have a great time.”

And I did!

When we got home we were a little drunk. Sid was still up and Karen told him all about the evening, we were all sitting on the sofa and he was in the middle. He asked how the evening was and I felt really embarrassed. Karen told him what happened.

“When we got there she really shocked but I knew she would have a great time. We got a couple of drinks found a seat and the guys came out and started dancing, taking off their clothes. She was really surprised when they got the audience involved and had them rubbing oil on their bodies. We were a bit further back at that point, but before long she was screaming along with the rest us ‘off, off, off’, and they whipped of the thongs.

“Each of the guys then went over to girls who grabbed their cocks and started wanking them to hardness, and that’s when I thought her eyes were going to pop out of her head.”

“What happened?” he asked. She went on.

“Well then they moved their cocks to the girls mouth and they started to suck them. The guys danced back to the stage and came back holding cams of cream, which they squirted on their cocks and offered it to women.”

Sid had a big smile on his and I could see his bulge was growing. He looked at Karen and asked, “How many did you try?”

“I had a couple of them in my mouth.” She looked at me, “How many did you have Sarah?”

It was true, when it was offered I was so worried at standing out by not joining in, I licked the cream off. That wasn’t enough for the stripper and he pulled my head towards him and he went in mouth. I was sucking his cock, feeling both enjoyment, embarrassment and a bit of shame that I was doing it. I told Sid this and he put his arm around my shoulders and pulled me close. I found myself cuddling into him.

“Sarah, don’t feel same. You’re a beautiful woman enjoying herself.” He told me and kissed the top of my head. “So how many did you have?” He asked me.

“Five.” I told him. “I’m not sure how many times. There was only one of them I didn’t have in my mouth.”

Sid smiled at me. “Did you want him as well?” I nodded and felt shame. I admitted I was jealous of the girl he took on the stage and she gave him a full blow job till he came.

“Why were you jealous?” Karen asked. Oh god! Why did I say that? I hid my face in my in may hands and Sid cuddled me closer.

I think Karen realised at that point what I was thinking. She reached over and with one of her hands pulled my hands away from my face. I looked at her as she asked me, “Did you want to taste what it was like?” I nodded. With her other hand she was stroking Sid and he was gently stroking my arm with his thumb.

“Do you want to try it now?” She asked as she slowly undid his jeans. I couldn’t speak, couldn’t move. I really didn’t know what to do as Sid continued to cuddle me and Karen got to her knees in front of him and pulled them down. His erection sprung free and she took it in her hands, stroking it lovingly. I watched as she took him into her mouth and reached the bottom, deep throating. She lifted up and smiled at me. “Join me.” She said. It wasn’t a command or a request, more an I know you want to so why not?

I looked at Sid and he smiled at me and moved in to kiss me gently. This time it was a full on kiss. We broke apart and he said, “I’d like it a lot.” I slid slowly to the floor and knelt next to Karen. She took my hand and put it on his cock, slowly stroking him with my hand before she took hers away. I’d stroked five erect cocks already tonight, but this one was different, the person it belongs to knew who I was. Karen nodded at me and I leant in, licking the head and running my tongue around it. Then I opened my mouth and took him in, enjoying the feel and taste of him in my mouth as I worked up and down. I couldn’t go as deep as Karen but he didn’t seem to mind. As I was sucking away and playing with his balls, I could hear him sighing and moaning, giving him loads of eye contact. It was so erotic, and pleasurable.

I was only half aware that Karen had moved away form me; when I looked up at him she sat next to him and they started kissing. My first threesome and I’m the one with a cock in their mouth I thought. I could feel the passion in him rising and that he was getting close. I sped up to make it happen, I wanted to taste him and I did, swallowing as well. I would never have thought cum was so hot.

In the morning I could hear Sid in the Kitchen and guessed that Karen was still in the shower. I quickly put last nights clothes on and some eyeliner and lipstick and went downstairs. He looked at me and smiled, no shame or problems about what happened last night. I said hi and he it said it back, asking me if I slept well. I apologised if him cumming meant he didn’t have sex with Karen but he told me it was ok; he enjoyed what happened as he sat down at the kitchen table.

This morning I was sober and had no doubts so I sat next to him and put my hand on his penis and felt it start to grow. He looked at me and smiled. So I got under the table and went down on him again which is how Karen found me. She said morning to us both and got her breakfast as he came in my mouth. I swallowed it all again and didn’t feel hungry anymore. He really was a heavy cummer. After he left I jumped in the shower and washed off the makeup ready for work. Karen did tell my girl team about the stripper night but left out all of the details.

Friday I was at Sue’s and we went out for a meal, mainly so I could get dressed up to be in a cocktail dress and stockings and I kept flirting with the waiter. Sue told they had an idea now for the character I would play during the contest and it was either playboy bunny or slutty nurse but no one could decide yet. The team would go out for a drink on Thursday and we would make the final decision so we could get what we needed.

Saturday afternoon I packed my case and got a cab to Karen’s. I’d been shopping in the morning and brought myself a new dress, just because I could. It was red and figure hugging with a flared skirt. I’d also been practising with cleavage makeup so it was low cut.

Tonight I was going clubbing again and I knew what I wanted to do, but not with Sid.

*In real life it doesn’t work very well at all.