Always the Bridesmaid...

...Never the Bride.

Growing up I always knew there was something different about me. I didn't fit in with the other boys in school, I wasn't into sports and all my friends were always girls. At a young age, I didn't understand sexuality and always assumed that I would end up marrying a woman and having children. But as I got older, things started to make more sense to me. By the time I reached university, I had a close group of friends were all women. When we'd be going on a night out, they'd all start getting changed in front of me and I wasn't checking them out. The one thing I was checking out was their lingerie and how I'd really like to try it on.

Eventually by the time I was 21, I came out as gay and it was a weight lifted from my shoulders. None of my friends were shocked, they were more surprised it had taken me this long to come out to them. From 21 to 23, were what I would class as my experimenting phase. I tried topping but I didn't feel like I was getting enough out of that, so I found myself an older man who was willing to fuck me for the first time. And that was the best decision I'd ever made. He fucked the cum out of my cock whilst I screamed underneath him and from that night onwards, I was 100% a bottom. Shortly after that night, I was able to move into my own place where over the next couple of years I slept with around 30 different men, but I'd never had a relationship. I stayed safe whenever I could, but immediately signed up to get myself on PrEP.

The one thing I kept from my friends, was my newfound love of women's panties. I had thrown away all but a couple of pairs of my male underwear and now exclusively wore panties. When at work, I always wore black or white bikini briefs so that if anybody spotted them it wouldn't be obvious that I was wearing women's underwear. I always made it clear when meeting men that wearing panties was my preference but if they weren't into it, I could either wear boring boxers or go commando.

I also already had a feminine figure. I was very slim, only around 5ft 4 inches tall so I was the perfect size and shape if men wanted to throw me around the bedroom. I signed up for a gym membership purely to work on my ass until I'd developed a nice little bubble butt. And by the time I was 25, I grown out my long blonde hair so that it was just past my shoulders. I quite liked having it pulled when someone was fucking me from behind. But like most people over here in the UK, I was stuck in a lockdown when COVID hit. Going two years without sex was an absolute killer for me and there was only so much a dildo could make up for.

But I think it's selfish of me to complain too much when my best friend had put her wedding on hold for two years. My best friend Katie was due to marry her long-term partner Cassie abroad before the pandemic. Katie and Cassie were complete opposites when it came to looks. Katie had long blonde hair that went down to the middle of her back, while Cassie had short hair that she dyed a dark shade of a purple on a regular basis. Cassie had tattoo's all over her body where Katie had none. They were both attractive women but when they told people they were together, the reaction was always shock.

I'd known Katie since school. We'd been best friends since we were 14. That meant my Mom was good friends with Katie's parents. My Dad would've been to, but unfortunately, he passed away when I was young. Luckily, my Mom and Katie's parents were both very understanding and didn't care about our sexuality as long as we were happy. I still hadn't brought a man home to my Mom but thankfully she wasn't the pushy type.

We'd had to cancel the bachelorette parties and luckily, they were able to get a refund for most of the things we'd pre-arranged. Thankfully though, the pandemic had moved on and we were able to get on with re-arranging the wedding and parties. All the plans had completely changed. Nothing would be taking place abroad. The wedding would take place in the Welsh countryside and the venue had hotel rooms and lodges where people could stay overnight. And the bachelorette party was now going to be a night away in York which was a long journey from London.

Our group of friends were all very LGBT friendly, with many of us either being gay or bisexual. We had some straight friends as well and they were very supportive of us all when we were on nights out where we might face some form of abuse. When they originally organised the wedding, Katie had asked me to be her groomsman or bridesmaid, I'm not entirely sure what the term is when you're supporting two brides. And Cassie had chosen her best friend Jane to be her chief bridesmaid. Jane was bisexual and was currently in a long-term relationship with her boyfriend Chris.

So, one Saturday in the build up to the bachelorette parties, the four of us met up in our local pub so we could finalise the plans of how we were going to get there and how many would be going. Everything was going smoothly as we quickly sorted out the different plans and we all agreed on everything so there was no need for any arguments. That just left us to have a few drinks and a catch up. We were approaching summer in the UK, so the weather was warm enough for us to move to one of the benches outside. We found one in the corner where nobody would be sat behind us. I sat next to Katie with Cassie and Jane sitting on the other side. After a while, Cassie and Jane headed into the bar to get us our next round of drinks whilst Katie quickly nipped inside to use the toilets.

Katie got back first and walked around the table behind me and sat back down next to me. She dropped her bag onto the floor and leaned into me, 'are you wearing lacey underwear?' She asked me with a big grin on her face.

I'd completely forgotten, but because I'd come from home, I hadn't thought about changing into my usual bikini briefs which were a lot more discreet than the Victoria's Secret thong I was wearing now. I reached behind me and could feel the lace on the waistband on the thong before pulling my t-shirt down to cover it. 'Do you want to say that a bit louder? I don't think the family on the other side of the car park heard you,' I said with a bit of an annoyed tone in my voice.

'So?' Katie looked at me with a blank expression on her face and when I gave her the same one back, she said, 'explain?'

'What's there to explain?' I replied to her. 'I like wearing women's underwear.'

'Since when?' She seemed amused by the whole thing.

'The last few years, I literally only own panties now.' I said feeling a little more comfortable about the situation.

'Oh my god,' she grabbed a hold of my arm. 'I have such a good idea now; you're going to love it. You can be my bridesmaid at the wedding. Like an actual bridesmaid.'

'What do you mean?' I was confused.

'You can dress up, we'll get you a dress, you'll look amazing. Please say yes.' She pleaded with me.

Before I had chance to respond, Cassie and Jane were heading back towards the tables with the drinks before retaking their seats. As we continued talking, I could see that Katie was on edge and really wanted to tell the table what she'd discovered about me. She kept looking across at me and smiling and then looking over at Cassie, I wasn't bothered if she told them, I wish she'd just stop acting so weird.

'Why are you two acting so weird?' Cassie asked. 'What happened while we were gone?'

Katie looked back across with me, like she was asking for permission to tell them. I looked at her and said, 'go on, you've been dying to tell them since they got back.'

Katie clapped her hands in excitement and then told the other two to come closer, so they started leaning over the table. 'James wears women's panties.' Cassie and Jane both gasped, putting their hands over their mouths. At least none of them laughed which was what I was most concerned about.

'How does everything fit in there?' Cassie asked after a little while.

'It just does,' I blushed a little bit. 'You just buy panties that can hold everything in place and for me that's a lot of them.'

Everyone around the table laughed. 'I'm a grower not a shower, what can I say?' I shrugged my shoulders. And it was true. When completely soft I was usually around 3 inches, maybe 4 at a push. But when fully erect, I was a good 7 inches and thick.

'So, back to my idea,' Katie started before looking across to Cassie and Jane. 'I thought it would be such a good idea for James to be my actual bridesmaid. We could help him dress up, it's a good idea, isn't it?'

Katie was looking, pleading with Cassie and Jane to agree with her. 'It's an amazing idea,' Cassie said. 'But that's only if James is okay with it. We're not going to force him into a dress for our wedding.'

Katie turned her attention to me, giving me her best puppy dog eyes. 'What do you think?' She asked me.

I mulled it over and thought about it. Secretly, I'd been thinking of dressing up for a while. I loved women's clothes, and I could everything in my sizes including the shoes which was good. 'We can give it a try,' I said before Katie jumped on me and hugged me. 'But what do we tell our parents?' I asked. With us being such close friends, my parents were invited to the ceremony but couldn't make the reception so they would still see me during the day. And of course, Katie's parents would be there.

Katie pondered on it for a little while. 'We'll tell them all together. They can come round ours and we'll tell them at the same time, we'll go shopping beforehand and they can then see what you'll look like.'

Suddenly I felt very nervous but agreed to ahead with the plan. We agreed to do it next weekend, that way I could tell them before the bachelorette party. And Katie's plan was to have me out dressed for that weekend. All in all, I'd have to be out in public 3 times, the party, the dress fitting, and the actual wedding. After the night in the pub, the following week seemed to go by slowly. I spent a lot of time online trying to figure out my size and what kind of outfits I thought I'd suit.

I invested in some more lingerie, this time focusing on bras and bodysuits. I was even lucky enough to still get some matching bras to the panties I already had. I also made a small investment in some fake breasts. They were only a B cup, so were small enough that people wouldn't notice but still gave me some extra curves on my chest. I started to look at my figure in the mirror and was so thankful for the ass that I'd worked for. It was an ass that most women would love, and I was so proud of it. On the Friday, I took the next step. I'd bought some hair removal cream and some razors and all though I didn't have a lot of body hair, when I had a shower than evening, I removed everything apart from my hair and when I slept that night, the panties felt so good.

When Saturday came around, I was full of nervous excitement, Katie picked me up in the morning. I just had a t-shirt and some jeans on as we made our way to our local tube station before heading into London to go around the shops. By the time we returned to Katie's house, I had about 10 full bags of clothes and shoes. And my bank card was in the middle of having a meltdown. We were sat having a cup of tea when Katie's parents and my Mom arrived. My stomach started to do somersaults as we sat and chatted. I was just waiting for Katie to start the conversation.

'So, as you know the wedding is fast approaching,' here she goes I thought, taking deep breaths. 'And James here, was going to be my best man, bridesmaid or whatever you call a guy supporting a bride. But you see, we have something different planned.'

'James is going to become my chief bridesmaid,' she said after a long pause. I looked around the room and tried to see what the reaction was, but nobody seemed to flinch.

'I think it's a great idea,' my Mom was the first to speak up. 'I think you'd look amazing.'

Katie's parents also agreed and for the first time, I felt quite calm at the situation. 'In that case,' Katie started again. 'We're going to head off upstairs and when we come back, I suppose you'll get your first look at James... or should we say Jamie now?'

Katie took me by the hand and took me up to her bedroom. Once we were in there, she turned to me and told me to strip. I did as I was told, not without awkwardness as I was stood there in a pair of pink bikini panties and nothing else whilst she watched. She then handed me a robe which I quickly put on and fastened before she sat me down in front of her vanity mirror.

She handed me a bobble and I tied my hair up into a bun, so it was out of my face. And for the next twenty minutes or so, I was at her mercy as she applied make-up whilst I just sat there and waited to see what the result was. By the time she was nearly finished, she started to apply some lipstick which felt strange before asking me to put my lips around some tissue which is when I saw that the lipstick was a shade of pink. The final thing she did was take my hair out of the bobble and use a curling iron to style my hair. When that was done, she asked me to turn around so I could look in the mirror.

'Holy shit,' was my first response when I saw myself. 'I look so different.' Luckily, I didn't have much of an Adam's apple so I could easily pass as female when I looked like this.

'It's not the best, but it was quick and on the day of the wedding we have a make-up artist who will do it all for you. Are you happy with it?' She asked nervously.

'Happy? I don't think I've ever looked better.' I gently touched my face to make sure it was me still.

She hugged me from behind before suggesting that I put some clothes on before our parents think we've ran off together. She handed me a white summer dress that was figure hugging on the top half and quite flowing on the bottom. Once I had the dress on, she finished the look by handing me some brown sandals and that's when we decided I'd need to get my fingers and toes painted before going out in public.

Katie held my hand as I made my way downstairs and into the living room as our parents all stopped what they were doing and looked in my direction. Katie's parents were all full of compliments for how good I looked. My Mom sat there with a gasp and her hands covering her mouth, she looked slightly emotional. I was an only child and had always thought about whether my Mom had wanted a daughter.

'You look beautiful,' she finally said before standing up and hugging me.

'Thanks Mom,' I said. 'I can't take all the credit, 99% of it was all Katie's hard work.' That made her laugh. 'Do you think I look okay?'

'You look perfect,' she said as her hands cupped my face.

I gave them all a twirl again, making sure not to flash my panties before heading back upstairs. 'Maybe have a better choice of underwear colour next time,' my Mom called out to me as I was on the stairs. I hadn't even noticed but my pink panties were obvious through the white dress.

After I'd gotten changed, Katie helped take my make-up off before helping me to my Mom's car with all the bags I'd gotten from the shopping. I was going to need a whole new wardrobe to deal with all this. Mom drove me home and helped me into my apartment with my bags. As she was leaving, she gave me another hug, and told me how proud my Dad would be. That made us both cry before we pulled ourselves together and she headed home.

The bachelorette party was next weekend. So, throughout the week, I bought myself some make-up and started to practice on myself two or three times a day depending on whether I was at work. As the weekend got closer, I felt comfortable enough to be able to do my own make-up if I wanted to travel to York dressed. I also had another spending spree and bought more lingerie and clothes, so I had plenty of options for the weekend.

By the time Saturday came around, I had a decision to make. There would be 15 of us travelling to York on two minibuses. I would be on the bus with Katie, Cassie, Jane and the two Mom's. And then they each had five friends coming each who would be travelling on the other bus. As a last-minute decision, I decided that I wanted to travel as Jamie. I packed some guy clothes just in case I bottled it at the last minute. But I got showered, got rid of any hair on my body and then got dressed. I chose a simple pair of white panties and bra. And then for comfort I chose a pair of my new joggers which had juicy written across the bottom, a simple spaghetti strap top which showed off my little tits with my fake ones inserted into my bra and then I had the matching jacket for the joggers. In my bag, I also packed anything I would need in case I got a little lucky on the night out, I'd asked for my own room overnight just in case I had the opportunity.

I made my way out onto the bus and prepared myself for the long journey. Initially they were all shocked at my decision to travel dressed, but I already felt so comfortable as Jamie, so I just had to. Once they got over the first shock we started drinking. We had a couple of stop offs on the way before we finally made it into York. As we were getting off our bus, the other people were just arriving and making their way into the hotel. Jane's partner had travelled up on the other bus and he was standing with another guy who was fit. I wouldn't kick him out of bed in the morning if I woke up next to him. He was the only other guy on the trip apart from me and Jane's partner. The rest were all women and a couple of them I recognised. The others I hadn't met before. One of them was stunning though. She had long blonde hair and was wearing a strapless top without a bra underneath showing off her perky nipples. She'd also travelled in comfort and was wearing a pair of leggings which turned see through in the right light, revealing her leopard print underwear underneath.

'Where's James?' Jane's partner asked when we were all off the bus.

'SHE'S already here,' Katie said pointing me out to Chris.

'Fuck off,' he shouted me when he saw me.

'No way is that James,' Megan said, who I recognised as one of Katie's friends.

Chris walked towards me, 'is it really you?'

'Yes, it's really me,' I said in the feminine voice I'd been practicing all week.

'Prove it,' Chris stood with his hands on his hips.

There was only one way I could prove it and it was a drunken mistake I'd made when I'd turned 18. We were on our first holiday abroad and we all decided to get a tattoo, the one I went for was a pair of red lips on my ass cheek with the letter 'K' underneath to represent Katie's name. So, when Chris told me to prove it, I put my bags down and pulled my joggers down enough so he could see my tattoo.

'Fuck, it is him.' He finally accepted, 'you look amazing.'

Once we got that out the way, we all headed inside and checked in. Luckily, my room was next to Cassie and Katie. Their Moms were further down the hall sharing a room as well. The rest of us were sporadically all over the same floor. I unpacked my things and started showering as we only had just over an hour before we were meeting up. We only had today, so we wanted to make the most of the time we had. I jumped in the shower and made sure I was thoroughly clean. Once I was done, I put on my complimentary hotel robe and headed next door.

Katie was already waiting for me and walked me to their vanity table. After about 30 minutes or so, I was done and looked just as fabulous as I did the other day. This time she straightened my hair for me, and I realised how long it was as it reached the middle of my back. Finally, she helped paint my fingers and toes a lovely shade of red which would match my outfit when I was ready. When I was all done, she sent me on my way, so I went back to my room and started to get dressed. I'd been planning my outfit all week and eventually settled for a pair of tight blue skinny jeans with a red lace bodysuit and a small pair of black heels. Underneath I went for a matching red lingerie set with thong panties and a lace bra that was see through.