A Pretty Sissy Bridesmaid

Danny's sister is getting married. His mom, girlfriend and sisters all have an opinion on the role he should play in the ceremony.

Preface - First of all, I'd like to address the fact that the story below is very much a 'genre piece'. That is, it knowingly contains many of the stereotypical plot contrivances that the majority of TG fiction also contain. Regular FM visitors will notice them immediately, so I won't go into them here. However, the story below is anchored in truth. 1. I really do have three elder sisters. 2. They did tease me about becoming a girl and threaten to dress me in their clothes 3. They DID dress me in their clothes occasionally - always skirts and dresses, and I pretended to hate it (but loved it)(there was no punishment from Mom, as in the story below, although I LOVE that storyline when I see it elsewhere) and 4. My eldest did tease me about being her bridesmaid, dress and all. Everything else is pure fantasy, although I remain on my own journey of transformation and self-discovery, some of which is reflected in this story.

Caitlin
xxx

CHAPTER ONE.

Growing up with three sisters can mean putting up with a lot. Especially when you're the youngest. For me, that was no different.

For as long as I can remember, my sisters Alice, Betty and Chloe, teased me mercilessly. Mostly, of course, as young girls do, for being a boy.

They would call me 'ugly Danny' because I didn't have pretty bows in my hair or wear cute clothes like they did, taunt me by lifting their skirts and flashing their underwear, or surround me and start kissing me without any let-up (what could be worse for a three year old boy?)

Later, completely innocently of course, the teasing became more psychological. They did things like hang a dress up in my room, and then say things like, "Doesn't Danny want to wear his pretty dress?", or offer to tie ribbons into my longish brown hair. They'd also tell me my legs would look good in skirts, and offer to put make up on me, if I wanted.

Later I found out this was a relatively ordinary experience for a boy with one or more elder sisters. At the time, I even began to think about it a little.

Mom sometimes joined in too. She'd threaten me with having to wear a skirt for misbehaving. Only once did she follow through on her threat. To punish me for swearing at my sisters, I wore a selection of my sister's skirts, along with other feminine under- and over-garments, for a whole week during the summer holidays when I was eight years old. Including outside the house.

Of course, I was mortified, but no-one was looking for a boy in girl's clothes, and it was easy to assume I was a girl, with my just short of shoulder length hair.

I never swore at my sisters again (in large part because as we grew up, all four of us became so close).

But that's another story (and one I might tell in future). This, however, is the true story of how I came to be the bridesmaid of my eldest sister, Alice.

Oh! And in case you thunk it ended with me being a bridesmaid, think again. My life was never the same again.

-------------------

My name (in case you hadn't realized by now!) is Danny. You already know I have three sisters and a mom. What I haven't told you yet is that I was also the only male in the house.

Dad had left just after I was born (in an ugly, but once again, innocent, episode, my sisters once told me he'd left because I was born a boy, a lie for which they were punished by mom). It would be easier for me to say that he left for another woman, or that the pressures of having to care and support four children had gotten too much for him.

No, he left because he finally came to terms with being gay. Something my mom had not realized until they very day he walked out. She never talked about him, and I had never known him.

Financially, it wasn't a problem. Mom came from a wealthy family, and we lived in a lovely house with a large garden and a swimming pool. Emotionally, it wasn't difficult for me (I had never known him) but I would say it must have been hard for my sisters who he doted in their early years. But Mom did so much to raise them well. Looking back, it would be fair to say they grew up to be headstrong, independent women who never relied on a man to feel good about themselves.

---------------

I was sixteen years old when I found out that me eldest sister Alice was getting married. By this time, Betty and Chloe were both in college, and Alice worked in fashion, for a fast-growing wedding magazine. It was just me and Mom at home. I remember the moment she told me clearly. It was just before Christmas, and all three of my sisters were due home for the holidays.

I walked through the door from school. "Danny! You'll never guess what?" Mom said with a big grin on her face. "Alice is getting married!!"

"To Eric?"

"Yes, of course, silly!" Alice had been dating Eric for just over a year. He was a trainee officer in the army. A big, serious guy. "We're going to start planning once all the girls are back."

That was on Friday. By Sunday, Alice, Betty and Chloe were back. Betty was studying psychology and was in her final year. Chloe was a first year medical student. Being attractive young women and surrounded by college guys...as we sat around the fire in the lounge, catching up, you can imagine how much of the conversation went.

"So Chloe, tell me about Freddie!!" exclaimed Alice.

Chloe lifted and then smoothed her skirt after crossing her legs defensively. "There's not much to say really. He's cute, and he has huge muscles..."

"He's a hunk then! Yummy!" Betty butted in.

"...but it's only been a couple of weeks and I wouldn't call it serious, not yet anyway. Let's just say there's potential."

"Another wedding on the cards, perhaps?" teased Mom.

"Oh, don't be silly Mom," replied Chloe.

"What about you Betty? Any recent romances you should be telling us about?" asked Mom.

"There've been a few, but I still haven't found the one," said Betty. "I'm having fun looking though!" she continued, to laughter.

Mom smiled, but also looked a little concerned. "As long as you're being careful Betty. You don't want to ruin your studies by getting pregnant."

"I am Mom. Don't worry about me. I'm careful with that sort of thing."

"Hmmmmm. I don't want the details", said Mom, "but just be careful."

"WE want the details," said Alice. "By the way Betsy Boo, your dress is cute. Where'd you get it".

"Oh, it is, isn't it." Betty stood up and gave a twirl. "Anthropologie. Glad you like. You can borrow it if you like."

"Speaking of dresses," said Chloe, "have you chosen your wedding dress yet Ally?"

"No, not yet, but Mom, I'd LOVE it if YOU would make the bridesmaids dresses."

Mom looked overjoyed. She owned a small boutique in town, mostly dresses, but also other women's clothes. She did lots of the tailoring herself. "I thought you'd never ask! Of COURSE I will. Who ARE bridesmaids anyway?"

"Betty and Chloe of course!! Who else!"

Both girls squealed with delight. "Thanks sis!" said Chloe.

"SO cool!" replied Betty. "You'd better pick nice dresses though! What colour are you thinking?"

"Either pink or lilac. They'll be cute, I promise!"

It was my turn to speak. "What about me Ally?"

Chloe butted in, "Feeling left out Danny? Don't worry, you'll look great in both pink or lilac!!"

I could feel myself blushing. If anyone noticed, no-one said anything. "Ha bloody ha Chloe. No, I mean, what would you like me to do on the big day?"

Alice pursed her lips thoughtfully. "I don't know yet, but I'll think of something. If you could be a bridesmaid, it would be SO much simpler. But don't worry. There'll be a role for my little brother! Besides, you'll be bringing Yasmin, right?"

Yasmin was my girlfriend of six months. My first girlfriend.

"If she's invited, yes."

"Of course she's invited," replied Alice. "How are things going with her anyway? I saw the photos on Facebook. She's a little hottie!"

"Yeah little bruv," contributed Chloe. "How'd you manage that? Is she on the swim team as well?"

"No. She's a cheerleader, but we met at a swim meet. It's nothing serious though."

"I should think so too young man!" said Mom. "You're sixteen!"

"Oh pipe down Mom!!" said Alice. "Things are different these days. Besides, you'll be careful, right, baby boy?".

"Of course I will! And for your information NOTHING has happened between me and Yasmin!! Not like 'that' anyway."

"Good," said Mom.

"Besides", said Betty. "You need to fill out a bit before you get jiggy with the ladies. You're as skinny as a rake."

"It's the swimming sis," I replied. "I train twice a day, but I eat like a horse. I can't help it."

All of my sisters looked at me sympathetically.

Our time apart had, if anything, brought us closer now we were back together. The rest of Christmas was amazing. It was just the five of us, before Alice left to spend New Year with Eric, and Betty and Chloe left to spend New Year at their respective colleges. I missed them lots.

--------------------

A few weeks after they left, I'd once again settled into a routine back at school. Things were going well between Yasmin and me. We'd definitely gotten more serious, and we were spending much more time together, and much more time in each other's houses.

Yasmin lived in a huge house on the hillside. Her father owned a local car dealership business that had grown over the last few years to now include several garages. She was an only child. And was absolutely doted on by both of her parents. They were very protective.

Which meant alone time in her bedroom, with her parents out of the house, was very rare.

One day in late January, we were kissing on her bed, when things got a little more heated than usual.

She was running her fingers through my long hair, when it started. "Danny," she whispered into my ear, "touch me."

"What do you mean?"

"Like this," she replied, holding my hand, and guiding it under her short pleated skirt.

I'd never done anything like this before, but I knew basic anatomy, and my sisters had talked to me, which meant I had some idea what I was looking for. I pushed her panties to the side, and started sliding my finger back and fore, gently between her legs. She was soaking wet already.

I carried on for a few minutes, when she whispered in my ear again. "Danny...I want to...give you a nice time..."

She brought her hand down to the fastening of my trousers, and felt around the outside of my trousers.

"Where is he?" she asked, confused. "I can't find it...I know..."

She slid down my body, bringing her head level with my crotch. Then, she unfastened my trousers, reached in, and...hesitated.

Just for a split second, but the pause, and it's meaning, was clear.

"Oh...he's so...so...cute."

Smiling and stifling a giggle, Yasmin pulled my erect penis out, kissed it once, awkwardly, and then wrapped her lips around it with ease.

I came, immediately. Yasmin swallowed, and brought her head back up, level with mine. She was still stifling a laugh, smiling awkwardly.

"Why are you laughing?" I knew the answer, but I needed to hear the words.

"Danny. Please don't take this the wrong way. But he's kind of...well...a bit small. And, well, I'd hoped you might last a little longer, so that we could...don't be offended though babe. It was...it was nice."

"I'm sorry Yasmin. I...I..."

"Shhhhh. Don't worry. Why don't you just finish what you started, but with your tongue."

With that, she pushed my head down underneath her skirt. She took fifteen minutes to orgasm, to my five seconds.

There were more intimate moments with Yasmin in her bedroom over the next few weeks, but always with me pleasuring her with my tongue. She took little or no interest in my penis, sensing my awkwardness whenever she got near. I wanted her to, But my embarrassment always won out.

-------------

Another month passed, and I was at home with Mom on a lazy sunday afternoon. I'd been working extra hard in swim training, to get fit for a competition the following month. Which meant, if anything, I was even slimmer than I'd been at Christmas time. Coach had also suggested I shave off my body hair, to get that extra split second edge. (A week later I'd take first place in a county competition, by less than one tenth of a second, so it was worth it).

I was reading downstairs, when Mom entered the room.

"Danny, would you please do me a favour?"

"Sure Mom. What do you want me to do."

"Okay," Mom said, looking a bit awkward. "I need your help with something, but I don't want you to be weirded out, ok?"

"Sure Mom. What is it?"

"Come with me upstairs."

I followed her up to her workspace. Mom did a lot of her tailoring up there, for her boutique business.

"I'm really struggling to hem these dresses. I'm usually fine with this sort of stuff, but without Betty and Chloe here, it's hard to know I've definitely got it right, even though I have their measurements."

I didn't like where this was going.

Mom continued. "I know you're the same height as Betty and Chloe (5ft 6, in case you're wondering) and I thought you wouldn't mind standing in for them while I made the adjustments. Just to be sure. Do you mind?"

"You mean...wear the dresses..."

"While I adjust them, yes." She could see me start to blush. "No-one will know Danny. Please?"

I knew this was a big deal for Mom. How could I refuse?

"Ok," I said, weakly.

"Oh Danny! Thank you SO much. You're SUCH a darling! Ok. Why don't you take your clothes off and come and stand over here."

"Take my clothes off in front of you?" I asked, apprehensively.

"Yes," Mom replied, laughing. "I've seen you naked before you know!" Sensing me hesitate, she continued, "Seriously Danny. Don't be a wuss! It's nothing I haven't seen before you know!"

Reluctantly, I stripped down to my underpants.

"And those," Mom said. "You didn't think you would be wearing boxer shorts underneath such a pretty bridesmaids dress, did you?"

I slid my boxer shorts down, and stood naked in front of her. I saw her glance at my penis, and noticed the double take. She didn't say anything. Just looked back up at me and smiled.

"Okay darling girl. I can see this is going to work." She handed me a pair of sleek pink panties. "Here, put these on cutey pie."

What did she mean, 'I can see this is going to work'? Humiliated, I slid the panties up. The panties were tight, giving me an almost smooth front...just the hint of a bump. I could feel myself blushing. I was regretting agreeing to do this already.

"Perfect. They're the same style of panties that Betty and Chloe will be wearing on the big day. Here, now put this on." She handed me a bra.

"Mom!! A bra? Really?"

"Oh don't be a baby!! The dress won't fit otherwise. And it's also the one the girls will be wearing on Alice's special day. It's padded a little, so you'll be the right shape for it."

She helped me put the bra on, then held open the dress for me. "Here, step into it, like this." I stepped into the dress, and put both legs together. She slowly pulled it up over by body. She looked into my eyes all the time, as if she was looking for a reaction. I gulped and bit my lip as I felt the pink tulle and chiffon skirt brush then caress my legs, and Mom zipped up the dress.

"Awwwwww. You look ADORABLE! Like a princess! You know Danny, I really didn't think you'd agree to this. Your sisters were right...with your small frame...maybe..."

'Maybe what?' I was thinking! My 'sisters were right'!? About what?

I had no time to ask. Mom continued. "At least it's a good fit. Now, put these shoes on so I can get the length right to hem the skirt."

Mom passed me some peep toe shoes that matched the dress. They had a bow on the front and a three inch heel. I stepped into them, and Mom got to work hemming the skirt to the right length.

As she was hemming, she kept talking about how pretty the dress was, and how good I looked in it. 'Like a real girl.' I was now starting to get aroused. If she noticed, Mom didn't say anything. Once she'd finished hemming, she looked at me strangely again.

"Danny, would you please indulge me? I need to see something."

"Okay Mom."

She spent the next 20 minutes styling my hair with curling irons, sliding in some clips, and finishing off with a pink ribbon. Then she added a some lightly applied make-up, some mascara, eye shadow, rouge and a pale pink, neutral lipstick. It really had an effect.

"Let's see you. Oh, my darling girl!" Mom looked at me wistfully.

"Mom! I'm not a girl!!" I cried. But I was still turned on. The shape of the skirt must have been hiding it.

"You could've fooled me. Have you seen yourself??"

I looked in the mirror. I looked like the younger sister of Alice, Betty and Chloe. Like a sixteen year old girl. In a pretty pink bridesmaids dress.

"I need photos, to show Betty and Chloe their dresses. And so they can see you, like this. Like their sister."

I felt humiliated. But I knew how important the dresses were to my sisters, so I let her. Plus, although I would never admitted it, I sort of liked it. Mom took some photos. I didn't pose much. I just sort of stood there, although Mom did ask me to put one foot slightly in front of the other, and clasp my hands together at the front.

"Ok. That's Betty's dress. Now let's get you into Chloe's."

I unzipped the dress, and slid it down. Like I said, the tulle skirt had hidden a bulge in my panties. A bulge that was noticeably bigger than it was when I'd put the dress on earlier. It might have been just a bit bigger, but for me it represented full arousal.

Mom definitely noticed this time. "Danny, I hope you don't mind me asking, this is really quite awkward for me. But I love you, and care about you deeply. So I have to ask. Danny, does Yasmin know, you know, about your...er...little problem."

"Mom!!!"

"It's ok honey. You look so pretty in the dress. Just like another daughter. There's nothing wrong in that. And you, er, seem to, to 'like' wearing it. We might be onto something...does she know?"

I looked down and answered, sheepishly. "Yes." Mom could tell I was embarrassed. She didn't push any further.

We spent the next few hours making sure the dresses were correctly adjusted. All the time, Mom talked to me about how pretty I looked, and about how she'd like to see me in the dress again. She even had tears in her eyes at one point.

As we finished, and as I walked out the door of her room, Mom said, "Danny. We must do this again. Perhaps with your little problem, it might be for the best."

I gulped, and asked, "Mom, what do you mean?"

"I mean, you, instead of, I don't know, pretending all the time... You could spend some more time in pretty dresses. See if you like it."

I walked out, and in fairness, Mom didn't press it with me again. Things went back to normal, and we didn't discuss what had happened for a few days. In fact, the the next time it was mentioned, it wasn't Mom who did it.

It was Yasmin.

------------------

I next saw Yasmin at her house just a couple of days later. I knocked on the door, and she looked excited to see me. More excited than normal. I could tell she was in a mischievous mood.

"Come in my beautiful boy! Let's go straight upstairs!"

Did she call me 'beautiful'? I was immediately on guard. She grabbed my hand and pulled me up the stairs and into her room, shutting the door behind her and turning to face me.

"Please don't be embarrassed by this question Danny. It might even...well...help explain some things."

Ok. Now I was nervous.

"I saw these photos on Chloe's Facebook page."

She showed me the photos. Oh my God. "You're Facebook friends with Chloe now?"

"Yes, since I got the wedding invite. Anyway, she posted these photos of her bridesmaids dress being modeled."

I looked at the photos. They were of me. But they were taken of the dress only, from the feet up to the neck. Phew. She couldn't see my face.

Yasmin continued. "The thing is, they still have the date in the corner of the photo. They were taken on the weekend, when your sisters were all away. And it's clearly your house in the background. That's your Mom's room."

She grabbed my hand, and with us both sitting on the bed, pulled it onto her lap. I was immediately conscious of my fingers touching the soft material of her skirt. I don't know why.

"So. I was thinking. If the photos were taken in your house, and it's clearly not your Mom in the dress...who's modeling Chloe's dress?"

"I don't know. Maybe one of my sister's friends?"

"At first, that's what I thought. Then I noticed this..."

Yasmin pointed to to a feint scar on the arm of the shoulder of the person wearing the dress.

"...and I thought, who do I know with a scar like this?"

Yasmin looked deep into my eyes, still smiling, and whispered, "It's you, isn't it?"

I didn't say anything. We both knew I had the same faint scar. My world was collapsing around me. I just looked at Yasmin. My lips parted, but no sound came out.

"I knew it!!! It explains so much! And there were moments I thought there was something wrong with me!!"

I just looked at her. "B...b...but..."

"No 'buts' Danny. I mean, what kind of man would agree to doing this? Donning a pretty dress, with shoes...and I can even see a bra!! SO cute. And the thing is, you actually look beautiful!!"

I just looked at her, too humiliated to move.

"I can tell you what kind of man! Not a man at all. A sissy! And especially with what you're packing downstairs. That's no good to any woman!"

"Yasmin...why are you suddenly being so cruel?"

"Not cruel, my pretty girl. It's for your own good. I'm going to help you. To help you find out if this is what you really need. To see if this is how you really...belong...in the world. I mean, I can't see your face, but you look GORGEOUS. You have the perfect body for that dress, and God knows you don't have the perfect body to be a man! Tell me, did you just wear the dress, or did you let your Mom do anything else? Did she do your hair?"

I returned, meekly. "Yes"

"Make-up?"

"Yes."

"Were you wearing panties? Surely not..."

I just looked at her, and although my lips parted, I didn't say anything.

"Wow! You agreed to all of that? Why?"

"To help my Mom! Honestly!"

"Really!? What sort of man goes that far to help their Mom!? To wear a pretty dress, lingerie, shoes, make-up?"

"I..."

"Listen Danny," said Yasmin, with an unmistakable gleam in her eye. "What I'm about to do, I'm doing for your own good. If you want to stop those photos circulating around the Facebook accounts of everyone at school, here's how things are going to work..."

So it came down to bribery. And apparently, for my own good. I still could've argued though.

I didn't.

------------------

Later on, Mom and I had just sat down to eat a meal she'd cooked. I was still embarrassed about the whole dress fitting episode. Looking back, clearly she was too. It's fair to say the conversation wasn't exactly flowing. Small talk, nothing more.

We'd both just finished our meal, when I decided to say something that wasn't small talk.

"Mom, about the other day..."

"Oh I'm so glad you brought it up. Danny, I'm so sorry. I just got carried away. You know, after the 'week in skirts' episode when you were younger, I sometimes thought it would be nice to have another daughter. Especially with your sisters gone. I know, for you, it was punishment. But for me, well, at times it was nice."

"Mom..."

"No, please Danny. I have to finish. I've been thinking a lot about it. Maybe it's because I miss your sisters. Perhaps it's just the thought of having another girl around the house. Or it could be because you're so slightly built for a boy, and, at least in my eyes, kind of pretty. I thought I might be, well, showing you another way. In any case, I'm so sorry Danny. It won't happen again."

I didn't know what to say. All I could think of was pictures of me all over Facebook. I had no choice.

"Mom. I don't know how to say this, but, I...I...I sort of...liked it." I couldn't believe the words had just come out of my mouth. And all to keep Yasmin from carrying out her threat.

Mom looked stunned. "You mean...you mean you LIKED wearing the dress? I don't believe you. I forced you to do it. You're a proper boy, not a girl. Not a ...a ...sissy."

"Mom, I liked it."

"I still don't believe you. I need to hear you say it." Mom looked half upset, half intrigued.

"But Mom! I just told you!"

"No Danny. I need to hear you say it. Say it all. Say...say...'I liked wearing the pretty dress."

"Moooooommmm. This is hard enough already. Do I have to?"

"Say it!" Mom snapped.

"I liked wearing the pretty dress." I can't believe I just told her that.

Mom continued. "I liked looking like a girl."

"I...I...liked looking like a girl."

She didn't stop there. "And I want to be your girl again."

"I...want...to...to be your girl again."

"Say it again. I don't believe you. Say..."

I repeated everything Mom asked me to. "I'd love to wear more pretty dresses... I need to stop trying to be a real boy... I want to wear cute lingerie... I'd like be a proper girl..." And most tellingly, "I'd like to be your daughter."

Mom suddenly had an idea, judging by the look on her face. And then she hit me with it. "Danny. Say, 'Please help me to be a pretty bridesmaid at Alice's wedding'."

"Mom!!!"

"If you want it, SAY IT. If you don't, it can all stop here. You can be my son again. But if you DO say it, then there's no turning back. You WILL be a bridesmaid at Alice's wedding. Pretty pink dress and everything."

I thought about Yasmin and her threat. Posting the pictures on Facebook would ruin me forever. In contrast, wearing a dress for one day...it might actually be something nice to do for Alice. And it's only one day, right?

I bit the bullet. "Please...please h...h...help me to be a pretty bridesmaid at Alice's wedding." I added, "After all, Mom, it's just one day. Right?"

Mom looked at me intensely. "I don't think so Danny. The wedding is in two months. To do this properly, we need to start right now."

"What do you mean?"

"Danny. This is Alice's big day. If you're going to be her bridesmaid, you need to be convincing. Like a real girl. With the look, mannerisms and voice of a real girl. You need to move like a girl, dress like a girl, feel comfortable as a girl, in the eyes of everyone at the wedding, BE a girl. You can't overshadow Alice by looking like a tranny."

Mom clasped my hand in hers, smiled and continued. "It starts right now."

I couldn't believe I'd gotten myself into this. One day in a dress had turned into two months of training. When Mom uttered her next words, it got even worse.

"And I know exactly who can help us. Someone who understands what it's like to be a pretty sixteen year old girl in these times. Who is feminine and understands fashion. Someone who knows you well. Who understands your...er...how can I say...little problem. Who can help train you, dress you and support you. But will also care for you, AND will be at the wedding."

"Who?"

"Who do you think? With your sisters all away from home, there's one obvious candidate. Yasmin."

-----------------

I later found out that although Mom had sent the photos of me wearing the bridesmaids dresses to all of my sisters, she hadn't told them I was the one wearing them. Remember, my face was cut out of the photographs that Yasmin had confronted me with.

Only Chloe, who'd posted the pictures on her Facebook account, had asked Mom who was modeling the dresses. Mom had told her it was Yasmin. We were a similar size. Another reason why Yasmin was the perfect person to guide me.

So none of my sisters knew anything at that point. Mom had planned for it to be a big surprise until the rehearsal dinner, when I would be unveiled as a girl, so the shock wouldn't overshadow Alice's big day the day afterwards.

I helped Mom with the washing up, and then she called Yasmin and invited her around. Mom was adamant that I had to tell Yasmin myself, oblivious to the fact that Yasmin already knew and was blackmailing me.

And that's how I found myself in the lounge, sitting on an armchair, opposite both Yasmin and Mom who were sitting on another couch.

Mom began. "Yasmin. Sorry to call you over to the house at such short notice. The thing is, Danny has something to tell you."

Even at the time, I have to tell you, I thought Yasmin's acting was amazing. She pretended to know absolutely nothing. And I couldn't let on to Mom because otherwise my wearing of the dresses would be exposed to the whole school.

I didn't say anything. Even though Yasmin knew, it wasn't easy to say. Especially to a girl I was supposedly dating. Mom said, "Go on Danny. Tell her."

Yasmin could see I looked nervous. She lent over and put a hand on my knee. "Danny, you can tell me. What is it?" she turned to Mom. "Is he sick?"

"No, no. Nothing like that," said Mom. "Danny. YOU have to tell her. She needs to know anyway. You're dating her for goodness sake!"

Yasmin actually pretended to look concerned. Yet to do so, it was obvious to me that she must have been thrilled with my predicament. Her hand was still on my knee. "Babe. You can tell me ANYTHING."

I looked at her. She was SO beautiful. She was wearing a casual, yet pretty, purple shift dress, with tights and heels. Her hair was immaculate. And she even had on a little make-up. It stuck me that she'd actually dressed for the occasion.

"Go on," said Mom, again. She folded her arms and crossed her legs defensively. As she did so, I was extremely aware of the way she lifted the hem of her knee length pencil skirt and re-set it on her crossed legs. Why was I noticing these things! "Danny, this needs to come from you."

I took the plunge. And with it, my life changed forever.

"Yasmin," I said, "I'm going to be a bridesmaid at Alice's wedding."

Yasmin laughed. "Is that all?? Is that why you invited me over? Honey, that's nothing. I've already been to a wedding with a male bridesmaid. Or more accurately, a best man to the bride. My cousin's wedding last year. Her brother was her best man. He looked after her ring, and even gave a toast at the reception. They were best friends as well as family - he was a natural choice. So it makes sense to me that you would be chosen to help Alice on her big day...I guess it just changes the sort of suit you'd wear. That's all, right? Plus, does it mean I get to sit at the top table?? That would be SO cool!"

Inside, I was shocked that Yasmin had chosen to make this more difficult for me. I just wanted to get this over with.

"No, Yasmin. I mean..." I looked over at Mom. She just nodded her head towards Yasmin, as if to say, 'tell her'. "I mean I'm going to be a proper bridesmaid. To be Alice's bridesmaid, with Betty and Chloe."

Yasmin looked stunned. Even though I knew she wasn't. She opened her mouth, but it was at least five seconds before any words came out.

"You mean...you're going to wear a dress? Like your sisters?" asked Yasmin.

I looked down at my shoes. "Yes."

Yasmin carried on. "Is anyone forcing you to...I mean...you actually WANT to?"

Mom spoke. "Yasmin. He ASKED to be a bridesmaid. He WANTS to wear a dress to the wedding."

Yasmin looked at Mom, then at me, then at Mom. "You mean, he WANTS to wear a dress. To look like a girl? Like...like a sissy?"

"Yes Yasmin," said Mom. "He came to me and asked me to be a bridesmaid. To wear a dress like his sisters."

"But why didn't you just say 'no'? I don't understand," said Yasmin. "I know it's stating the obvious, but he's a boy!"

"There's something I've missed out. You see, I needed someone to help me adjust the dresses, and only Danny was in the house. The only way of being sure I was hemming the skirts to the correct lengths was to have someone wear the dresses. So Danny helped me. He wore the dresses."

Yasmin looked shocked. "So he's already worn the dresses?"

"Exactly," replied Mom. "And a bra. And panties. And shoes."

Yasmin turned to me. "I didn't know you were gay!"

"I'm not!" I cried. "I like girls. I like you!"

Yasmin held her finger up to me, and I stopped talking immediately. "Yes," she said, "it all makes sense. I'm sorry to say this in front of your mother, but...well..." Yasmin turned to me Mom. "He never seemed... well... that... ahem... aroused... when we were making out."

Mom looked a little embarrassed, but not enough to stop the exchange.

"I was! It's just...just that I'm...I'm...smaller than most guys!" I said. What a thing to have to use in an argument.

"No," said Yasmin. "That's not it. You were small, but also...well...floppy."

Mom butted in, clearly trying to change the subject. "Here, I have some photos."

Mom picked up her iPad, and showed Yasmin the photos. The versions with my face still in the picture. THE VERSIONS WITH MY FACE STILL IN THE PICTURE!!!! I couldn't believe that there were photos with my face on!!! I genuinely didn't know Mom had taken any like that.

Yasmin looked at the photos and looked both surprised and amused. "Oh. My. God. You're...you're...cute. I mean, you look good in the dress. AND you have your hair styled. AND make-up. You look...like a girl. A bit more work and you'd be gorgeous."

Still looking at the photos, Yasmin said, "But that still doesn't explain why you wouldn't just say no. Even if Danny looks good in a dress, how can you let your own son be turned into a girl? I mean, what does this mean for me and Danny?" She looked up from the photos at my Mom.

"This is embarrassing," said Mom. "But he clearly...enjoyed it."

"Yes," said Yasmin. "I can tell from his smile in the photos. But..."

"No," said Mom. "That's not what I mean. You can't tell because of the tulle skirt. But when we changed dresses, he had...I don't know how to say this...a bump...in his panties. Bigger than normal."

Even though it was true, I had to deny it. "No I didn't!!"

"You did," said Mom, quite calmly. "Why would I lie about that? You think it's easy for me to say? That my son likes to wear pretty dresses and underwear? That's he wants to look pretty...to be more attractive to...that he's gay?"

"I wasn't turned on! And I'm not gay! I'm attracted to Yasmin!! And she's a girl!" I sounded desperate, and I knew it.

"There's an easy way to find out," said Yasmin, looking at my Mom.

My Mom understood immediately. "Yes. All of your sister's old clothes are still in their bedrooms. The ones they didn't take with them. Come on. Let's go upstairs. We'll soon see if you're telling the truth, Danny."

Mom grabbed me by the hand, practically dragging me out of the room. I say practically, because I still went willingly. I looked behind. Yasmin was following us upstairs. She smiled and winked at me. Now she had access to the photos with my face in. Although I could have passed for a girl, to anyone who knew me, I was completely recognisable.

I knew Yasmin had me in a corner.

We went into Chloe's room. As the youngest of my elder sisters, she had most clothes still in her closets. My Mom opened the closet doors, at the same time directing a firm, "strip please", at me.

"But Mom! I can't..." I complained.

"Yes you can. It's nothing neither Yasmin or I haven't already seen. Yasmin, see if you can find some panties and a bra. Something pretty. That drawer there."

Yasmin grinned at me. She looked in her absolute element. "Sure thing!" She rummaged through the drawer, as Mom looked for some clothes. I had no choice but to strip.

Yasmin found some pink Elle MacPherson panties and a matching bra, the most feminine set she could find. She held out the panties for me to step into, smiling at me all the time. I pulled them up. Yasmin checked for a reaction, some arousal. Nothing. Because of my small penis, I was almost flat, like a girl. I gave Yasmin a look that said, 'told you so.' she just looked more determined.

Yasmin then reached around me to secure the matching bra. Still no arousal. Mom looked away from the wardrobe and over her shoulder at me . She smiled, and said, "cute lingerie Danny...hmmm...pink," almost casually. She returned to looking for an outfit, while Yasmin quickly tied my hair back, leaving side bangs to frame my face and securing a flower hair clip.

I looked down at myself. Aside from a small bump in my panties and a lack of breasts, I looked like a girl. No leg hair, because of the swimming. And a lean body. Partly because of the swimming, but also, I knew, I was a late developer. I was still just sixteen.

Yasmin was looking casually for any stirring in my panties when Mom suddenly exclaimed, "Oh yeees! This will do nicely!"

She turned around from the wardrobe towards Yasmin and I holding the cutest, prettiest pink party dress I've ever seen.

"I bought this for Chloe when she turned sixteen, so it should fit you nicely Danny." Mom turned, grinning, to Yasmin. "Chloe wore it to her sixteenth birthday party, and so she was wearing it when she received her first ever kiss from her first boyfriend, Mark."

"Aaaaaw," said Yasmin. "So this dress DEFINITELY attracted the guys! Cute! What do you think, Danny?"

I said nothing. Oh my God. I knew that story. Chloe had fancied Mark for over a year, and had finally made out with him on her sixteenth birthday. Mark was a year older than her, and a real jock. What Mom didn't know, and that Alice, Betty and I did, is that Chloe, refusing to lose her virginity with him, had given Mark her first ever blowjob that night. In other words, I was thinking at the time, Chloe had worn this dress, and sucked her very first cock. And, I knew, from Alice and Betty teasing her at the time, that she'd enjoyed it. Every minute.

And why wouldn't she? Mark was an athletic, muscular guy with an apparently impressive package. Chloe had swallowed everything he gave her, partly to save her pretty dress, but mostly to ensure no-one else at the party could find out what had happened.

The dress was very, very girly. It had thin straps over the shoulders, a tight bodice, and a knee length skirt with a tulle underskirt to give it some volume. It was three different shades of pink, and was made from a super-soft material. Inside the top half it was lined with a silky material. The tulle of the skirt, acting as the lining, was high quality and very, very delicate and soft. Not the hard, corse tulle you sometimes find on cheaper clothes.

Yasmin continued. "So Danny. What do you think? How do you feel knowing you're going to wear the dress that Chloe used to ensnare that gorgeous hunk of a man, Mark??"

I can't explain why, but as Yasmin was looking for a reaction after her words, and as Mom held out the dress for me, my penis stirred a little.

"Oh my God!" said Yasmin, noticing immediately and turning to Mom. "You were right! Danny DOES like guys!"

"No I don't. I just...I...I..."

Mom just said, "I'm not looking Yasmin." She looked at me, looking amused again. "Let's just get this dress on you, shall we my darling girl?"

Mom held out the dress, and I stepped into it. As she pulled it up my body, I shuddered with sensation. The soft material of the dress, and the tulle underskirt slid gently past my legs. Mom couldn't have picked a more feminine outfit. Yasmin had the pleasure of zipping me in, giving me a quick peck in lips once she'd done so.

Once I was in the dress, Yasmin stepped behind me, running her hands lightly down the length of my dress (yes, MY dress)and gently over my body. She held my skirt on either side of my legs and shook it lightly. The sensation on my bare legs was both heavenly and disturbing.

Mom, standing in front of me and admiring, suddenly said, "Hmmm. We're missing something...I know! Shoes!!!" She stepped out of the room, giggling excitedly. Yasmin and I were alone.

"How do you feel, Danny??" she whispered in my ear, still caressing my body gently. "How is my sissy? It's so good to see you in such a wonderful dress, in the flesh. You look SO pretty. And to think, this is the dress Chloe wore to get her very first kiss. Mark obviously LOVED her in this dress. Now YOUR dress."

While Yasmin spoke I could feel myself getting more and more aroused. "Stop it," I whispered back, demurely. "Please..."

"Ssshhhhhh gorgeous girl. The thing is, and I'm guessing here. Sixteenth birthday party...good looking girl like Chloe...wearing this dress...I bet she did more than just kiss Mark."

Yasmin moved one of her hands over the front of my skirt. Over my crotch. She stroked very lightly, through the skirt.

"I bet Chloe was practically fighting Mark off, one he'd seen her in her pretty dress. I bet he was VERY pleased to see her. I think, while they were dancing close, she'd feel his hard penis pushing against her. And she'd think, 'I want to keep him happy. What can I do?' I bet she spent some of the night on her knees, with her lips around his hard penis...sucking..."

How did she know? I later found out, she didn't. It was just what Yasmin and countless other good looking teenage girls had done in similar circumstances to keep the men they fancied satisfied without having to put out.

"Just think Danny. You're sixteen now, but on your seventeenth birthday party, that could be you. In your darling pink dress. One of the hottest girls there. Getting lots of male attention. On your knees. Wanting to please him. Sucking your man's penis." Yasmin laughed at my reaction. Humiliation written all over my face. Yet a stirring in my panties as she lightly touched me through the dress. A stirring she could feel.

Mom walked back in the room. "Here you go Danny! Some nice pink heels. Four inches this time. Let's get these on you."

As I stepped into the heels, my legs elongated, pushing my bum out slightly. Mom was busy doing the straps of the shoes up. Yasmin, still behind me, moved her hand from my front, and around to the crack of my behind. Through the skirt, she pushed a finger gently but firmly towards my hole. Mom couldn't see a thing.

Yasmin whispered very gently, out of Mom's earshot. "And after you've sucked his cock, perhaps he'll bend over, flip your skirt up, and you'll beg him to take you here."

She pushed her finger firmly against my hole. At the same time, I moaned and came into my panties. It was obvious to both Mom and Yasmin that I’d orgasmed. Yasmin covered her mouth with her hand and smiled. Mom's reaction was different. She looked stunned.

"Danny! What have you done!!!???" She lifted up my skirt. I was mortified. My Mother had just seen me orgasm. As far as she was concerned, in response to me dressing like a girl, in a pretty dress and heels. "Lucky for you there's none on the dress. It's confined to the panties. Now go and clean yourself up. No need to take your dress off. Just lift your skirt up, rinse yourself off and change those panties. Yasmin, please find Danny a new pair."

"With pleasure", said Danny.

Once I'd cleaned myself up and was wearing a new pair of panties, Mom said, "Danny. I think we need to talk."

-------------------

Five minutes later, the three of us were sitting in the lounge again. This time, all three of us were in skirts. Yasmin in her purple shift dress. Mom in her pencil skirt. And me in my pink party dress, along with heels.

Mom began. "Danny. First of all, you need to sit like a lady. Cross your legs please, and smooth your skirt down afterwards."

With the thought of the photos going public, and the humiliation of orgasming in front of Yasmin and my Mom while wearing a dress, I did as she told.

"That's better Danny. First of all, we need to come to terms with what just happened. Obviously your request to be a bridesmaid is at least partly motivated by your emerging sexuality. Wearing the dress Chloe wore for her first kiss had caused you to...well, we all saw what happened."

Mom turned to Yasmin. "I'm sorry you had to see that Yasmin. Obviously you won't be dating Danny any longer, but I would like you to continue to help. Danny will need a role model, someone her own age."

'Her?', I thought. I'm a boy!!! "But Mom!"

"No Danny. My turn to speak now. Yasmin, is that ok?"

"Sure. Of course I'll help her," said Yasmin while smiling sweetly at me. "How can I abandon her now when she needs to come to terms with being a sissy?"

"Exactly," said Mom. "See Danny, how lucky you are? To have someone like Yasmin? Most girlfriends, or more accurately, ex-girlfriends, would be furious. I know I was when I found out about your father. But Yasmin is putting YOUR needs first."

"But Mom, I don't need..."

"How will you know what you need Danny? This is your first time being a girl. Yasmin and I need to talk this through. Work things out for you. On the one hand, we need to prepare you to be a bridesmaid for Alice. On the other hand, we need to think about what today's events mean for you, and your future."

“Yes”, said Yasmin, smiling. “Your future as a girl”

----------------

To be continued.