A Sissy for A Bridesmaid

It was the night before my sister's wedding when she approached me.

"I need to ask you a big favor for tomorrow," Jessica said, "And I don't think you're going to like it."

"Just tell me," I said, "It's your big day and I'll do anything that I can to make sure it goes well."

I had always been a bit of a pushover, someone so happy to help that it didn't take much to make me do things I wouldn't normally consider, just because a friend or loved one asked. So, I kind of knew already that I'd do basically anything if my big sister wanted a favor on her wedding day of all days. But even so, I wasn't entirely prepared for what she was about to ask me.

"I want you to be a bridesmaid," Jessica said.

I guess for a lot of people their sister asking them to be their bridesmaid would be an honor. But then most of those people would be girls! For a straight guy to be asked to be a bridesmaid was a whole different proposition.

"Cassie's had to pull out. She broke her leg," Jessica said, "And you're the only person who'll fit her dress!"

Jessica and Darryl had been planning this wedding for eighteen months, trying to get the ceremony she'd always dreamed of when we were kids. She hadn't gone full bridezilla, but she was determined to make sure that everything ran smoothly and perfectly and that everything fit her picture perfect dream wedding. And Cassie not being able to make it across the country had thrown that all off. You see, Jessica was very much one of those brides who had picked out her bridesmaids and their dresses to fit a certain look that she had in her head. They all needed to match, which meant that they were all her tall and slender friends. And, most importantly, they all needed to pair with Darryl's groomsmen. Like Darryl himself, these were all - from his cousins to the guys he used to play football with in high school - strapping athletic black guys. And here's where the trouble came in. Darryl had a best man and four groomsmen, but, without Cassie, Jessica had a maid of honor and just three bridesmaids. And symmetry in the wedding party was a big part of the bride's vision for her perfect wedding.

"Why me?" I asked, "Surely there's another girl who would be a better choice."

"They're all too short or too curvy," Jessica said, "Believe me, you've got a better body to be flattered by this dress than most real girls! Nobody else would come close to fitting it."

"Why not just have one fewer people?"

"Because then both sides won't match," Jessica was sounding increasingly frustrated in a tone that I knew would soon make me cave to her will, "Darryl won't drop any of his groomsmen and I'm not letting one of them come down the aisle alone. It will look weird. Jayden was supposed to be paired with Cassie. He'll go fine with you. He's a good guy."

"OK, fine," I sighed as my sister's face lit up with delight, "But what would I actually have to do?"

"Just what any bridesmaid does," she said, "Wear a pretty dress, walk with me down the aisle, look cute in all the photos and dance the night away at the reception. It's the easiest job in the world!"

I admitted that wouldn't exactly be the worst way of spending the day.

"And you get to play a bigger part in the happiest day of your sister's life. Surely it's worth it just for that."

"Wait, what do Mom and Dad think about this? Have you run it by them? They can't be crazy about their only son being dressed like a girl in front of the whole family!"

"They said to go for it. They know how important it is for tomorrow to be the perfect day for me, so they'll let me do things however I want."

It was true that Jessica was pretty much a spoiled princess for our parents. Unlike me, she could do nothing wrong and they happily catered for her every whim. Hell, they'd already forked out a small fortune on this wedding. Of course they weren't going to stand in the way of their favorite child now.

"Well, then, I guess there's no way I can say no, then."

"Great," said Jessica, "You'd better go get an early night. The bridesmaids have all got to be up at 5 in the morning for hair and makeup!"

And with that she left and I had agreed to spend my sister's wedding day as a male bridesmaid. Oh well, I guess it would be an experience to remember.

***

I was up bright and early the next morning, not entirely sure what to expect from the day to come. The wedding ceremony and reception were taking place in a luxury hotel, which was also where the wedding party and family were staying. I headed to the bridal suite where Jessica had spent the night apart from her fiance and where this morning the bride and her bridesmaids were getting ready.

"Don't mind Leo," Jessica said to the other bridesmaids as I arrived to find them in various states of nightwear, underwear and bathrobes, "Just for today he's one of the girls. Think of him as Lulu not Leo!"

"So, you're a bridesmaid, too, "Lulu"?" said Beth, Jessica's best friend from high school and maid of honor. Beth was tall, leggy and an absolute knock out, with chestnut hair in a short bob and dark brown eyes. Back in high school hundreds of guys had crushes on her and I was pretty sure that she knew I was one of them. So it was pretty exciting to see her wearing little more than a chiffon slip, sipping a glass of champagne. "Welcome to the party!"

"Grab a glass and join us," said Ashley, my sister's college roommate and another bridesmaid, an athletic, sporty blonde, "If you want to be a bridesmaid then you've got to take advantage of one of the few occasions you can drink before breakfast!"

I happily took a glass and took a big sip. I had a feeling that getting a couple of drinks inside me was what I would need to pluck up the courage to go to a big public event dressed in female fashion. I sat in the suite's lounge area among the half dressed girls and tried to enjoy being given access to these hot women at a time that few guys would. Along with my sister the bride, Beth and Ashley, there was also Tara and Lauren, a pair of sisters who were also college friends of Jessica. A couple of years apart in age, they could almost have been twins with their long legs, tanned bodies, blonde hair and full lips. Both were dressed in plush robes with their hair up, waiting to get ready.

Hanging up on one side of the room I could see the four bridesmaids' dresses, the ones that could only fit me and none of Jessica's other girl friends. The dresses that had sealed my fate for the day. The dress was a dusky pink in chiffon with a just above the knee A-line skirt and a scoop neck with lace edge. There was a pink ribbon around the waist. Honestly, I could definitely see the likes of Beth, Ashley and the sisters looking very good in it. Jessica wasn't the kind of bride who was jealous of her hot bridesmaids stealing her spotlight and dressing them in ugly dresses. No, she was the kind of bride who made sure her bridesmaids would all look almost as good as her to make everything picture perfect!

"OK," said Jessica, "I have something else for you all, including Lulu. Well, it was for Cassie, but you can have it instead. It's the underwear to go with the bridesmaid dresses."

She opened a box and pulled out five matching sets of pink strapless bras and lace thongs.

"Here we go, 32B for you Ashley. Lulu, I guess you're an A cup!"

"OK, I agreed to the dress, but why would I need the underwear?" I asked. This whole thing was really starting to get away from me.

"It won't look right without the right things beneath," said Jessica, "Back me up here, girls."

"That's right, it will ruin the line and shape of the dress," said Tara, already out of her robe and showing off her bare chest and a pair of delightfully perky tits as she put one of the bras on herself.

I was embarrassed and didn't know where to look. Tara was brazenly and shamelessly exposing her breasts, seemingly without a care. The gentlemanly thing to do would be to look away or leave the bridesmaids in privacy. But wasn't I supposed to be "one of the girls" too today? If I was going to have to go through all the rest of this then a little naked female flesh to gawp at was the least reward I expected. So gawp I did.

"Besides, I'm sure you won't have a problem wearing the underwear," Jessica said in my ear so that only I could hear her, "Given how often you used to borrow mine! Be a good bridesmaid and I'll stick to keeping that just between us."

I was shocked. Yes, it was true. Like many guys I was fascinated by sensual women's lingerie, far sexier than anything guys got to wear. And, like many guys, that curiosity had led me to want to try it for myself. Yeah, it felt good and sexy wearing panties and stockings, I could definitely see why girls were into this. And of course the nearest place I could find sensual lingerie to borrow was from my sister. But I never guessed that Jessica knew about this little habit, this kink, of mine. This was the first time she had ever mentioned it. Had she been saving the knowledge up for a moment like this? Hanging it over my head? Was my secret desire to wear feminine underwear the whole reason for my current bridesmaid role?

I had a million thoughts and questions, but none of them that I had time to dwell on now. Right now I just had to get on with it. Jessica was, as ever, in control and I was going to follow her demands. She was right that I would rather everyone not know it was not my first time wearing women's underwear. And for that reason I had to wear them now. Besides, it was also true that I kind of did want to wear the bra and panties and feel so sexy. I'd just never imagined doing so in front of an audience of other people.

Getting shirtless and putting the strapless pink bra on wasn't so bad. I wasn't exposing much of myself and in return got the treat of four gorgeous babes revealing four fine sets of luscious young breasts. I particularly appreciated the opportunity to see the beautiful bare boobs of Beth, the biggest crush of my teenage years. Two perfect round orbs with little firm nipples, I couldn't help imagining sucking on them. But putting on the lacy thong was more of an awkward experience.

Beth had dropped her little slip to reveal a perfect shaved pussy and pert little ass, before stepping into the sexy thong. She did it in front of all the other girls, who were following suit and doing the same, which meant that I had to as well. At least Jessica had gone into the bedroom to get herself prepared and bring out her wedding dress, so I was spared the humiliation of showing my big sister my little dick. There was no way of avoiding doing the same, though, in front of her closest friends.

Knowing that I would have to spend today in a knee-length dress, I had got up earlier that morning and completely shaved not just my legs but every bit of hair from my skinny pale body until I felt totally smooth all over. I had heard that shaving your balls and pubic hair can make your dick look bigger, but it didn't seem to have had much effect on making my puny pecker look any less embarrassing in front of the other bridesmaids.

"Wow, what a tiny little thing you've got there," Ashley giggled as I slipped off my shorts, "It's probably more suited to a pretty pink thong than boxer shorts anyway!"

Any hope that I had of subtly slipping the panties on without the girls paying too much attention to the little floppy piece of white meat dangling between my legs was gone. Not once Ashley drew attention to it. Now the other three all wanted a look. It seemed like in the all-female space of the bridesmaids' room, and with a couple of glasses of champagne inside them, the girls had no sense of decorum or any need to hold back. They were just having giggly fun.

"Wow, no kidding. I've been with a lot of guys and I don't think I've seen one smaller," Tara said, actually coming over to get a closer look. She had already put on the underwear and was now the first in the room wearing the dusky pink bridesmaids' dress as well. Now here she was kneeling in front of me examining my flaccid little penis. I'm sure that having a hot girl in her bridesmaid outfit kneeling up close to his dick is what many guys want from a day at a wedding. But in those scenarios I doubt the bridesmaid is holding it between finger and thumb and giggling at its miniature girth. "What do you think, sis, tiniest ever?"

"Maybe," Lauren, Tara's older sister joined her, "I might have seen one or two white boys this small before I followed Jess' advice and went black!"

"I feel sorry for you, then," laughed Ashley, "I don't think I'd even feel a little pecker like that inside me. Hell, Lulu might as well have a big swollen clit. It's much the same!"

I couldn't believe it, but the bridesmaids' mocking was actually getting my little manhood hard. Maybe it was just that my cock had never received this much attention from so many hot girls, but I think perhaps having my inadequacy pointed out in blunt, crude terms was actually turning me on!

"Come on girls, that's enough," Beth came to my rescue, stepping over and tucking my semi-erect little creature into my sensual lacy panties, getting me even more aroused with her touch, "Yes, Lulu might not have much when it comes to manhood, but doesn't that just make her all the more perfect as another bridesmaid."

"What was that? Lulu's not got much? We can fix that with these?" Jessica said, coming out of the bedroom in her underwear, carrying her wedding dress. Fortunately it quickly became apparent that she wasn't referring to what was between my legs, but instead thought that the conversation she had just heard the end of was about my chest. She was holding up a couple of oval-shaped flesh-colored objects. "Some of the girls use these to pad out their bras a bit," she added, "You can put them in yours to give you a bit of a chest. It will make the dress suit you better that way."

I was far too humiliated and focused on trying to hide the little erection in my panties to put up any fight about the fake breasts that were swiftly stuffed into my bra. Then I slipped into the dress. I needed Ashley's help to zip it up and tie the pink bow around my waist. But it only took a moment before I was wearing a pretty bridesmaid's dress like the four other girls and it really did make me feel like one of the team. The cute dress with its pink lace and knee-length skirt was like a uniform that made me into one of the girl squad. The other bridesmaids teasing my small white dick may have stripped away some of my masculinity but now that was being replaced instead by some newfound femininity.

Jessica herself was wearing some quite plain underwear, designed more to shape her body under the form fitting gown she had picked out for the day, than to look great in itself.

"But I'm ready to give my man a night to remember," she explained, "I've got my bridal lingerie all picked out to change into once I'm out of the dress. And it'll give my new hubby just what he wants on his wedding night."

She showed us what she was planning to wear and the bridesmaids cooed approvingly. I didn't really want to think of my sister in a sexual way but, as someone with a history of "borrowing" her underwear, I had to admit she had good taste in sexy lingerie and what she planned to wear tonight would drive any groom on their wedding night wild. There was a white satin bustier with a floral lace pattern, a white lacy garter belt and stockings and a pair of lacy white bikini-cut crotchless panties.

"So sexy, Honey," Beth said.

"He just won't be able to resist," added Ashley.

"He'd probably just want to skip straight to the wedding night once he knows what's waiting for him," the blushing bride herself admitted.

Along with Beth, who was also now in her pink A-line dress, I helped get Jessica into her bridal gown. It was a gorgeous, form-fitting white dress with a flared mermaid skirt and sweetheart neckline, sparkling with sequinned patterns. The bride had to be laced into it from the back, which required the efforts of both me and the maid of honor, but once it was on it looked incredible. And now all six of us were ready for our hair and makeup.

The girls all knew just how they liked their makeup to enhance their already attractive features, but this was a whole new world for me so I was grateful that wedding prep came with experienced professionals.

"Don't worry, when I'm done with you you'll look every bit as gorgeous as any of these girls," Mary the makeup artist was telling me as she sat me down and began to apply foundation to my face, "You wouldn't even be the first boy bridesmaid I've worked with and by the time they were ready it was impossible to tell them apart from the real girl bridesmaids!"

"And with your hair there's plenty of wigs, extensions and hair pieces we could use to make you look more feminine," Paula the hairstylist jumped in from where she was teasing the bride's brunette locks into a curly up-do.

It took a while of Mary's expert attentions, blusher, dusky eyeshadow, mascara, carefully painted and lined lips in a rosy shade; but sure enough I could see in the mirror my face becoming more and more beautifully feminine. Once Paula added a wig of long, brown waves that looked a lot like my sister's natural hair, I had to admit that it was true that I could easily pass for a bridesmaid who had been a girl all along. In fact, taking in my whole look - the pink dress, my hair and makeup - in the bridal suite's full length mirrors, I thought that I didn't just look passably feminine. I looked hot. I looked like the kind of bridesmaid that drunk and horny guys desperately tried to hook up with at the wedding reception. Hell, I looked like the kind of cute bridesmaid that under normal circumstances I would probably hit on!

"Looking good, Lulu," said a genuinely impressed Tara as she noticed me checking out my own reflection.

"Yeah, you're definitely one of the girls now, Lulu," Lauren chimed in.

"You're gonna have to be fighting the guys off this evening," Ashley laughed, "I hope you'll be OK with that!"

"Careful you don't make the bride get jealous of her own hot bridesmaid," said maid of honor Beth, seemingly only half joking, "You can't go outshining a girl on her wedding day."

"Wow," my sister, the bride, added coming over and giving me a hug, "I never knew what a pretty girl you'd make. This is going to go even better than I thought. Maybe it's for the best that Cassie couldn't be here."

And, you know what, I was starting to think that too.

***

"You look stunning, Honey," my dad said as we stood outside the hall where the ceremony was due to take place, awaiting the processional. He was saying this to the bride, I should mention, not to me. "I'm so proud of you today, looking every inch the beautiful blushing bride."

"And you," he said, turning to me, "You look like a girl, son.

"I guess I was wrong to tell Jessica that this was a crazy idea, because she's right. You'll pass as a bridesmaid. I mean, you look more convincingly like a girl today than you ever passed as a man before!"

"Dad!" said the bride, with largely affected shock and offence.

Beth had handed us all bunches of dusky pink roses and gypsophila, with Jessica carrying a far larger bouquet in similar shades of pink, cream and white. We were waiting for the processional and I was trying to practice walking elegantly in the pink strappy sandals that all the girls were wearing. I'd never walked in heels before and, after three morning glasses of champagne, I was tottering uncertainly on top of these four inches. My heart was fluttering with nerves at least as much as the bride's about walking down the aisle like this. What if I humiliated myself by tripping and falling, my skirt flying up and flashing my pink panties to a hall full of my sister's friends and our family?