Becoming a Bridesmaid Pt. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Before heading downstairs, I transferred my essentials from my handbag into the pink heart-shaped clutch bag which we all had to match with our outfits. There wasn't much room in the clutch bag, so I made sure I had my phone, some lipstick and foundation for any touch-ups, and a couple of discrete panty liners. I had recently started to get used to carrying panty liners, as unfortunately the cage took some drying and I would occasionally leak slightly, so if in a rush I would use the panty liner rather than risking my panties. I suppose it was just another part of my life as a woman.

Everything moved quickly after that. It wasn't long before the four of us gathered, and had a few photos taken. Stood around Jessica in her wedding desk, with myself, Ellie and Lou in matching bridesmaid dresses, I had never felt more in the right place. I knew, deep in my heart, this was right for me. I smiled in the photos, feeling on top of the world, before we headed outside to travel to the Church.

*

After about 5 minutes at the Church, I started to relax and feel even more comfortable. I had worried for the last few weeks what people would think about me, if people would point and stare, but it wasn't like that. For one thing, all the focus was on Jessica, but also I felt so confident in my look, I knew I looked amazing.

The ceremony itself was beautiful, I was stood at the front of the Church as Jessica walked up the aisle and looked stunning. I was so enraptured by the beauty of it all, the grand building, the guests, and the clear love between Jessica and Adam. At one point, I felt as if I was about to shed some tears, but stopped myself at the thought of my make-up being ruined.

During the exchange of vows, I ended up briefly locking eyes with the best man, who I later found out was called Jamie, and was Lou and Adam's cousin. He gave me a smile, and I smiled back. I thought it was just friendly, but I couldn't help but notice how great he looked in his suit. For the last week or two, I had started noticing men more and more, something I had barely thought of before. I put it down to my frustration at being in chastity, especially since Lou got me thinking about it with the magazine, and her telling me about experiencing the 'real thing'. I tried to shake the thoughts out of my mind, and returned to being entranced by the ceremony.

After the vows were exchanged, and we started leaving the Church, I felt enormous happiness for Jessica, as well as being proud that I had done it. Something that didn't feel like a remote possibility not too long ago, I had done it, at first for my friend, but I had found something for myself along the way. At my heels clicked along the Church floor as we left, I felt as if I was walking on air.

*

The venue for the reception was a short drive away, and Lou grabbed me as we headed out as she found a ride for us. One of Adam's friends was driving us over in his car, with Lou sitting in the front. I sat in the back on my own, but realised we were waiting for some others. As I looked out of the window, I saw a couple of the groomsmen heading for either door, one was the best man, Jamie.

The other groomsman, Dan, opened the door opposite me, with Jamie opening the door next to me. I started scooting into the middle seat, careful to not let my dress ride up my legs too much. It was a tight fit in the back of the car, and both of the men either side of me took up plenty of space as they settled in, spreading their legs wide. I pushed my legs together, as Jamie put his hand onto my knee as he adjusted for more space. I have to admit, I did feel that twitch in my clit again.

On the short ride, Lou introduced me to Dan, Jamie and the other man driving, Addy. I was very conscious of myself, at the centre of the car, but reminded myself that I looked great. Jamie then complimented me, "You look amazing." to which he clearly smiled as he saw me blush.

As we exited the car, Jamie turned around as he stood up, and offered his hand to me, I grabbed it, again feeling a twitch.

"Let me buy you a drink."

I blushed even more.

***

"Lou has been telling me all about you," Jamie told me after he bought me a cocktail.

"Really?" I giggled, looking up at him as he sipped a beer.

"Oh yeah, I was excited to meet you, but you look even better than I imagined."

"Thanks... you look good too."

"Well, we will have to do something about that then."

Just then, we were interrupted by Dan who dragged us over for some speeches. It gave me a chance to compose myself, was I just flirting with a man?! Also... was I enjoying it?! I headed over to the table where everybody was gathering for speeches, and tried to focus on that instead.

It was beautiful hearing the speeches, from Adam, Jessica, her parents, and then Jamie himself gave a speech. I couldn't help admire him as he stood up, so tall, looking muscular under in his tight fitting suit. My mind kept flashing to images of Lou's magazine, of muscular men in tight underwear, and then back to Jamie, my clit was twitching.

Again, trying not to think about this too much, I allowed myself to be whisked to the dancefloor by Ellie to watch the first dance. Jessica and Adam looked great together, and it felt so wholesome to be watching, stood with Ellie hand in hand. We joined the dancefloor with others after their first dance, having a good time dancing with Ellie, then Lou joined in too, I was one of the girls.

Myself, Ellie and Lou giggled, danced and drank for most of the evening. I must have had quite a few cocktails by that point, and was feeling tipsy, but a really good kind of tipsy. With the music playing, being with my friends, and my bridesmaid dress fluttering as I danced, I had my best night out. Over the years, on the rare times I had been dragged to a bar or a club by Ellie or Jessica I had always felt uncomfortable and out-of-place, conscious of myself, and essentially just waiting to go home. Tonight, I felt like I was meant to be there, I had the attention of others, and I was loving it.

After a good while dancing, a slow dance started, and I took it as a chance to filter off the floor. I think it was a Taylor Swift song. As I was heading towards the bar, a hand appeared around my waist, it was Jamie.

"Up for a dance?"

"Err... sure" I tried to remain cool.

He took the lead, and held me close. He was without his suit jacket now, just his white shirt which I could see his muscular torso rippling through. I could feel his hard upper body pushing up against me as he pulled me in tight, taking a firm grasp of my hips. I moved my hands high up to his shoulders, which I was surprised by the broad and strong feel of. We swayed like this for a while, locking eyes, I had never felt anything like this.

Then, Jamie started to move, he removed one of his hands from my hips and too my left hand. The grip on my hips with his other hand tightening. He guided me around slowly, me just following, and looking up into his eyes. Lights flashed by, but all I could focus on was Jamie. Occasionally his crotch would graze my upper hips, and I couldn't help thinking about those moments constantly, almost trying to make it happen.

The dance felt both eternal, and too quick. As the song finished, I struggled to peel my gaze and smile from Jamie.

"Quite a show." he whispered to me.

I smiled, but then looked around, and saw that by the end it was just us on the dancefloor, with a decent crowd watching. I immediately saw Ellie and Lou as part of that crowd, both smiling. Whilst I was ready to start blushing and feeling embarrassed, that didn't happen, I was proud.

Afterwards, I made a beeline to Ellie and Lou, who fussed over me, asking me all sorts of questions. I smiled, and admitted that I did like Jamie, I couldn't hide it any more.

After a couple more drinks, the night was winding to a close. As most of the remaining guests started either getting a taxi, or heading to the hotel rooms, Lou grabbed me and handed me a key card.

"What's this for?" I asked.

"My room, you can have it."

"What? I'm sharing a room with Ellie, it's okay."

"I'll share with Ellie now. I think you might be a bit busy..." Lou winked, handing me the card before walking away.

I then saw Jamie heading towards me.

*

The walk up to room had nerves returning. I was definitely thrilled as well, but I was also terrified. Jamie remained calm, and held my hand, reassuring me.

We entered the room, and it was luxurious. Though the main focus was on the huge king-sized bed in the middle.

Jamie closed the door, and gently pulled me in for a kiss. My world alighted, and I loved the feel of his stubble rubbing on my face. His kiss was powerful, but without force, and he tasted so good. My head was swimming. I wanted him.

As he reached for the back of my dress, I quickly asked to freshen up in the bathroom. I tottered to the bathroom in my heels, and composed myself. First, touching up my make-up slightly, and then checking myself. I removed the panty liner, which I was right to add before the dancing, as I had noticed I leaked slightly during my dance with Jamie. The last kiss didn't help either, so I tried to dry myself, before pulling the panties back up, and heading back out.

Jamie quickly removed my dress, leaving me in only my white bra, pink lace panties and silver high heels. I sunk to my knees, and he stood firm in front of me. I grasped for the fly of his trousers, and pulled down the zip. He only helped by removing the clasp on his trousers, letting me easily pull them to the ground. Then, in front of my face, was a large cock barely concealed by the tight Calvin Klein underwear. I was astonished, entranced, but also worried about what to do next.

I caressed his cock through the pants, it was so big, I had no experience of this. I tried to think of what I would have liked before I was in chastity, but this felt completely different. Jamie had a huge, thick cock, my clit was short and even before it was locked up, I had never felt it hang, and I couldn't even get a full hand around mine. This was different, I was going to learn.

As my face got closer, obsessed by the huge package in front of my face, Jamie pulled down the front of his boxers. The cock flung out, and actually hit me in the face.

"Wow!" was all I could say.

"Impressed?" Jamie smiled.

I nodded, and went to kiss the head. I was slightly embarrassed as I gently kissed the tip of his penis, but it grew slightly as I did. Taking that as a good sign, I gently licked the tip more, starting to fit the head of the cock into my mouth. It was so warm, and I couldn't help but think about how much I loved the taste too. I noticed I could still lift the cock higher, as it was only semi-erect; which meant two things, firstly, I had work to do, but also, this thing got even bigger!

I continued to suck Jamie's cock, enjoying the taste and feel. I could start to feel the cock throbbing as I felt the warm head start to grow even further in my mouth. I tried taking it further and further, knowing it was the right thing to do. Jamie held the back of my head, helping me. Though as hard as I tried, with the warm and wonderful feeling of the cock deep in my throat, I could barely get a third of the way down. This was a real cock, at this point the head of Jamie's cock alone was probably twice the size of anything my clit had ever done.

I took a break from choking on Jamie's cock to attend to his balls. They also hung, huge, and impressive. I greedily licked every inch of them, also enjoying the taste and feel. So warm. I tried to maintain eye contact with Jamie the whole time, even though he didn't always look down at me. On my knees with Jamie's warm balls in my mouth, starting up past his thick cock into his eyes as he stood and enjoyed it, I felt in completely the right place.

I returned to his cock, now clearly fully erect, and throbbing. I enjoyed the feel in my mouth and throat once again, before Jamie pulled back slightly, my mouth opening and allowing the cock to exit as I stared at him. He pulled me from my knees and carefully but powerfully turned me around as I rose. I then felt him push the top of my back towards the bed, I allowed my head and body to fall on top of the bed. I then felt my panties quickly rip off and fall to my ankles, realising my heels were still on, so they didn't fall off.

"On your knees." Jamie told me.

I quickly shuffled forwards, my face down in the bed, my hips and ass up in the air, with my knees together. The next feeling was one I will never forget. I felt intense pleasure as his warm cock started to enter my pussy. He clearly struggled, and despite my training over previous weeks with toys, the size of Jamie meant there was an effort to fit inside, but he kept pushing until he slid inside. It was painful, but it felt so good.

My eyes rolled into the back of my head from pure pleasure, I had never felt anything like this. Lou was right, the real thing was so much better. I was completely lost in pleasure, my face buried deep into the bed, eyes rolling with pure joy, I couldn't help letting out high pitched moans constantly. Jamie thrust behind me, his strong hands firmly on my hips. This was true pleasure.

I don't know how long it took, it could have been 5 minutes or 5 hours, but pleasure rose up inside me beyond anything I had ever experienced. I felt myself orgasm, but not was I had in the days before chastity, something on another planet. As Jamie thrust deeper and deeper inside of me, as presented myself on my knees, the constant pleasure built up into a huge crescendo, I felt my body surge with pleasure. I moaned so loud, my body starting to shake, and I felt the soft leaking that had come from my clit throughout the fucking turn into a true orgasm, and cum gently seeped out from my cage.

"Enjoying that eh?" Jamie breathed after hearing my shakes and moans, still thrusting.

"Yes... fuck... God YES!" I screamed.

He continued to thrust, and it still felt good. What was happening, didn't cumming mean I was done? But as Jamie continued, I didn't want it to stop, it was still the best feeling.

He picked up the pace, thrusting harder, occasionally slapping my butt and jiggling it. His breath grew quicker, I continued to moan and beg for him, he was getting close. I wanted to make it as good as possible for him, after he gave me the best feeling of my life. He continued to hold my hips tight and thrust harder and harder.

"Where do you want it?" Jamie asked.

I was unsure at first what he meant. Then I realised his cum. "Wherever you want" I replied.

Jamie pulled out of me, which was a strange feeling, I felt so much... empty space. Though he quickly spun me onto my back, and raised his knee onto the bed. I raised my head slightly, but he pushed me back down. Looking up at his giant cock as he was about to burst. He brought his cock closer to my face, and finally exploded. There was so much cum, completely covering my face. I felt huge loads over my lips, my forehead, some dripping into my eyes. I just smiled and thanked Jamie as he lay down beside me.

I started to feel for the hot cum on my face, allowing myself to taste some of the loads which had fallen on my lips. It was so warm and salty as I held it in my mouth, but felt strange as it all held together, I decided to swallow it, and the feeling of Jamie's hot cum sliding down my throat was heavenly. I caught Jamie looking, and he smiled.

"Fuck that was good." I told him.

"I know."

***

Epilogue

I woke the following morning, at first wondering where I was. My head was blurry from all the drinking.

As I pulled myself together, I noticed my head was resting gently on a thick muscular torso. Jamie. It all came flooding back.

Wow. I suppose it had really happened after all.

Jamie gently rose, and asked me how I was. We chatted briefly, but it wasn't long before he was guiding me under the sheets to give him a proper wake up call.

*

Jamie left the room for breakfast, whilst I went to get ready.

I showered, needing to clean my hair well from the cum that had dried there last night and the fresh load left earlier that morning. I also noticed some dried on my face, giving it a good clean.

After applying my make-up, I realised I had left all my clothes in the room I was supposed to stay in with Ellie. All I had here was my bridesmaid dress, and some cum-covered panties. I messaged Lou.

Ten minutes later Lou arrived, quickly giving me an impressed look as she saw the mess of the room.

"I take it you enjoyed yourself?"

I smiled and nodded.

"Here," Lou handed me my clothes, "I'll see you down at breakfast?"

I nodded. Though just as she was leaving I couldn't help but notice no key on her ankle.

"Is the key in here too?" I asked, pointing to my stack of clothes.

"Oh, no, I didn't think you would be wanting that. I gave the key to Jamie."

Lou left the room. I was shocked, but also, found that I didn't mind too much. After what I experienced last night, I realised I couldn't go back to how I used to get pleasure. The orgasm with a clit was beyond anything I had experienced before. I suppose I could ask Jamie for both, but, somehow, I didn't think he would want that. Besides, I after seeing the size of his cock, I couldn't claim to have one myself.

No, I was ready to fully accept life as a woman now. I had been sold on the clothes and the lifestyle for some time, but now I had accepted it all.

I pulled on Miss Julie's old red lace thong and matching bra, and pulled over a pink bodycon mini-dress. I was ready to head downstairs.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
20 Comments
4Leather4Leather22 days ago

Think I typed a note once before. Love the store now that Jamie has the key leaves the door open for a third chapter. Please

AnonymousAnonymous5 months ago

This was really hot but I didn’t like the cishet normativity, one can absolutely be a woman without being with a man. Giving the key to a guy without asking for consent was also particularly fucked up. So yeah, no. It’d have been way hotter if the main character actually had sex with her boss, even if the cage stays.

JackiemichelleJackiemichelle10 months ago

Great story. Would be great to become who you always should have been. To be loved and accepted

AnonymousAnonymousabout 1 year ago

There's no way that Lou should pass the key on to Jamie without finding out if they wanted the cage remove she was conniving and not very good and shoot God Jamie too have sex with her that is wrong totally wrong I disliked it all together thank you

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
Working the Holidays Classic Christmas tale of blackmail and forced feminization.in Transgender & Crossdressers
More Stories