Sleepover Sissy

Summary: Hannah, Rosie, Molly, and Brie have the perfect sleepover planned. It had been a while since they had a good girls night in, but things take a turn when Hannah's ex Mike makes fun of them. In a turn of events, Mike is slowly turned into one of the girls in a night he or she will cherish for a long time.

"Are you sure you don't want to come?" asked Hannah. "I know it's a girls night, but you're welcome! It might be fun? We can include you in all our activities. " Said Rosie. "Yeah. I mean we were going to do some girly stuff but if you're around, we can watch a movie or do something a little less gendered!" said Brie. "Yeah. We'd love to have you be a part of our party! Doesn't have to be a girls night" said Molly.

"Nah, I'm sure," I replied dismissively. "I'm going to go home and do something manly, like play Guns of Duty or BorderFall 3. I don't want to ruin your girls night, or be a part of it.

"Have fun!" I said, without realizing how douchey I'd just sounded.

"Fine," Hannah replied. In hindsight, she'd clearly realized it just fine. "Suit yourself. Let's go, girls." They all went upstairs to her apartment.

Hannah was my best friend. She and I had dated for a year until we realized it actually wasn't working. We'd broken it off mainly because we thought we would be better as friends. Hannah was five foot six, just like me. Whenever she wore heels, then, she actually looked taller.

I made my way to the apartment. I was just about to sit down with my microwaved meal when I heard a loud bang outside and the power went off.! I cursed loudly, then immediately called the power company.

"Yeah," the nameless operator replied. "It looks like the whole block's out. Our men are on it, but because of a transformer bust, I don't anticipate power back 'til tomorrow night. "

That wasn't good news for me. It was freezing out. With no heat, I'd be in for a terrible night if I stayed home. I decided to call Hannah.

"Hey," I said sheepishly. "It's me. Listen, there's a huge power failure here, and I need a place to stay the night so I don't freeze my balls off. Can I crash at yours? I promise I won't interrupt your girls night." I remembered what I'd said before, how I'd said it, and how Hannah had reacted. I figured there'd be some resistance - or, at the very least, a cheeky comment from Hannah.

"Yeah, okay," was all she said, casually as could be. "We'll see you in twenty minutes?"

"Yes! Thank you so much!" I exclaimed.

"Yeah, don't thank me yet," she replied. "Thank me in person."

I detected something off in her last sentence, but I was way more focused on the prospect of power and heat. I put some clothes in my backpack and headed off to Hannah's house. In twenty minutes I reached the door and rang the bell. Instead of being greeted by Hannah or one other girl, the door opened to the sight of all four. "Well, well well," said Brie. "Look who showed up for girls night after all!" She flipped her blonde hair back dramatically.

Brie was easily the tallest of the girls, standing at five foot seven. Blue eyes formed a classic combination with her hair.She was an athlete, which lent her even more of an Amazon vibe. She reveled in it; she wasn't shy about the fact that she was exclusively into women. Her breasts however, were - in her own words - "lacking," but that didn't stop her from owning it, and calling herself "Flat Bitch."

"Yeah, what gives?" asked Molly in a mocking tone. "Now you want to hang out with us girls? I thought you wanted to be a man and do manly things!"

"Now, now, it's cold and we should let her in," Rosie said as I registered the use of 'her' to describe me.

"Sorry, bro," Hannah said, "it's girls-only now - and, last I checked, you were a man! Or so you said."The girls all giggled.

It was starting to snow.

"Oh come on," I whined as I started to shiver. "I didn't mean all that. It's cold! Please, let me in."

"No," Molly said defiantly. "You said what you said, and we said what we said: girls only."

I sighed, and was about to turn around when Rosie said, "You do know what that mean,s right?"

I shook my head.

"Wow! She really is dumb!" Rosie exclaimed, using feminine pronouns again. "You can come in if you agree to let us make you a girl. "

I stood in silence, still shivering. That didn't make any sense to me at all.

"What?" I finally exclaimed."It's simple, really," said Molly. "We don't allow boys at our slumber party, so allow us to make you over, and you can be a girl, and thus allowed to stay over tonight!I really don't see how you have a choice. Plus, once you're a girl, you can join in on all the activities with us!"

"Um. Are you sure I don't have a choice?" I asked as I started to weigh my options.

"You don't," Hannah answered. "You brought this on yourself by being a massive douche. Now, I can promise that we will be the only ones seeing you tonight."

"Yeah, I can't make that promise," Brie said as she brandished her smartphone.

"Fine. I'll be a girl," I said. "Please let me in." The girls all started to clap.

"Hold on," Molly said. "Are those your boy clothes? You don't need them. Give that to me." She snatched the backpack while Hannah and Rosie each took one of my hands and ushered me inside.

The door closed. Instead of being at the mercy of the elements, I was at the mercy of four women.

"Okay," Brie said, almost as soon as the door had shut. "Let's see what we're working with here. Strip."

"What?" I exclaimed again. I hadn't signed up to be stripped naked in front of my ex and her three bossy friends.

"You heard her," said Molly. "Strip! How do we know how to size you up for a makeover if we can't see your body?"

"Mol is right, you know," Rosie chimed in. "We need to know your size, how much we'll need to wax, and how to do your hair!"

"You heard them," Hannah said. "Don't give me those eyes. You have no one but yourself to blame. Besides, who's to say you won't like being a girl more?" She giggled again.

"Yup. Strip!" repeated Brie.

Nervously, I removed my clothing until I was down to my boxers.

"You're going to have to remove those too, hon," said Hannah.

"No," I replied. "I'm done. You guys win. I'm not going to stay here." I turned and stormed towards the door. I obviously wasn't thinking very clearly.

"Sure," Molly said, "but where are you going to go? Also, going out in just your boxers? In this cold? "

She laughed. I looked to Brie who had my backpack, and had picked up my clothes.

"Yeah, you're not getting this," she said. "Remember, no boys allowed!"

"Hon, I've seen it before," Hannah said, "and I don't think it'll bother any of the other girls here.

"Think of it this way," Rosie offered. "We're all girls here. There's no need to be ashamed."

"Yeah, here." Brie said, dropping my stuff. "Here's my tits." She lifted her shirt and quickly flashed me her perky chest. "Now can we get on with this?"

Stunned, I nodded and removed my boxers.

All the talk and blushing had me sort of excited, and my dick was semi erect. I'd expected some sort of reaction to my penis, but I saw none. Hannah had seen me naked tons of times, and Brie was a lesbian, so I hadn't expected her to react much, if at all. Molly giggled and whispered something to Hannah, who nodded and giggled right back.

Rosie just said, "And turn around?"

I turned around, baring my butt to the ladies.

"Now that's a girl's butt!" Brie exclaimed. "It's super cute!"

"I will admit," Hannah said, "I used to be jealous of that butt when I was dating him. My own butt looks like cardboard compared to that." She turned her butt towards me and the other girls and gave herself a spank.

"Okay, ladies," said Brie, walking around me, and clearly taking charge. "Girly butt aside, I think our work is cut out for us. Michelle here does need a body shaving. She also needs some work on her nails, makeup and hair, and then, finally, clothes. I'm not worried about the clothes because she can borrow from us. I think her bra is roughly my size, and she looks to be your size panties, Hannah, although we may have to do something about her... situation."

"Ooh!" Molly exclaimed. "My ex was a drag queen, and they used to tuck their junk, so I can show her how to do that. I'll take care of her shaving and waxing too. Rose, do you want hair or make up?"

"I got both," Rosie replied. "Hannah can collect some clothes for her, and Brie is on Margarita duty!"

"Sounds like a plan!" said Hannah as the girls all dispersed, leaving me naked and alone - until I felt someone yank me. It was Molly. I supposed I should have known, but I was still dazed and confused.

"Okay, Michelle," she said. "I'm going to help you shave your body smooth. Get in the shower, run the water, and start shaving. Give me a holler when you get to your bikini line. You'll need my help then. "

My head was spinning. Michelle? Shaving? Makeup? I must have looked a mess, because Hannah came around and could sense it.

"Moll, do you mind if I have a word with her?" Hannah asked.

"Yup" Molly said as she disappeared.

"You okay?" Hannah asked. I was about to answer, but she cut me off. "You know what? Don't answer. Look, I guess we were just trying to have some fun - and these are my best friends. They're not going to tell anyone. If you want to quit now, we won't be mad and would understand."

Then she came closer, and whispered,"Although, going by the last time you wore my panties, we both know that you like it."

She winked at me, and that pushed me over the edge. I immediately got a boner. Obviously, Hannah saw it.

"Yup," she said smugly. "So I'm going to say that you're going to be going ahead with us, yeah?"

I nodded ashamedly.

"Moll, she's all yours," Hannah said before winking again and running to the kitchen.

I went to the bathroom and turned on the shower, got in, and then started shaving my chest, arms and legs. When I got to the bikini area, I heard the knock on the bathroom door.

"Come in," I said.

It was Molly, except now she was clad in only her bra and panties. "Okay," she said, "so, let me help you with your bikini area. You want to be really careful. Here, let me do it. I used to help my ex."

I handed her the razor. Molly was a well-built woman with dark brunette hair. She had the biggest breasts of the bunch, and I'd heard she was the sluttiest member of the girl gang, although she's settled down now.

"So you're going to want to spread your cheeks for me," she said. I did a double take. "Listen sweety, I have a razor. You're going to want to be careful of any sudden movements you make. One wrong move and your little clitty is in danger."

I moved across and spread my legs. I felt Molly put on some cream in between my butt cheeks.

"And I know what you're thinking," she continued as she began to shave my taint and balls. "Yes, I called it a clit, and yes, I have definitely seen bigger."

Once she was done, she let me shower off the rest of the cream and the stray hair. I got out of the shower and grabbed a towel. As I was about to start drying myself off, I heard another knock. At that point, I'd just stopped caring.. The girls had absolutely humiliated me, and I knew it was about to get worse.

"Come in," I said.

Rosie entered. "Oh good!" she said. "You're done. Come with me, sweetie - towel on, although it doesn't matter. We're all girls here." She wrapped the towel around my chest for me - as though I had breasts to cover up - and then took my hand. Molly followed behind us, clearly interested in watching the next part of the show.

Unlike Molly, Rosie was still mostly clothed, wearing a set of satin shorts and a matching chemise. She led me to the makeup table, where I sat down. Rosie was Asian. She had dark hair and kind eyes. She was definitely the sweetest member of the group, and, even now, was definitely more compassionate than the other girls. Rosie stared at me for a minute and was about to say something when she was interrupted by Brie, who was carrying a large tray of shots.

"I just finished the margs, but hey, now's a good time to take a shot, right?" She handed me one, and Molly grabbed another from the tray.

"Cheers bitches!" Molly said as she took the shot.

I took mine more cautiously, and felt the alcohol go right through my chest.

"Now, where were we?" Rosie asked herself, getting lost in her makeup bag.. "Ah yes. So let's start with the cheekbones..."

Rosie was a registered beautician, so she knew what she was doing. Meanwhile, Hannah had arrived, and she was holding multiple bottles of nail polish.

"For your nails, what's it going to be? Pink? Red? Or baby blue?"

"Um, baby blue?" I answered uncertainly.

. "Ooh I like it!" Hannah exclaimed. "That should be your color: baby blue! Let me see if we can get you some matching clothes. Moll, you want to take over her nails?"

Hannah handed one bottle to Molly and then ran back to the bedroom. Molly came over and started working on my nails while Rosie was doing my makeup.

It was then that I started to take stock of my situation. There I was, in front of my ex's friends, naked, humiliated, and emasculated, while they were doing my nails and applying make-up.

Rosie must have finished because Molly took a look at my face and said, "Wowza! She's hot!"

"Yeah," Rosie agreed. "I think I'm done. With the hair, it's long enough, but I think I'm just going to make it a little more fem with some clips. Luckily, I think I do have some baby blue - because that's her favorite color!"

Hannah returned. "Okay," she said, taking stock. "Nails: done. You'll need to let them dry for a bit."

Brie, meanwhile, came around again after another trip to the kitchen bar, returning with a fresh round of drinks and said, "Wow! Has she seen herself?"

I had not. Rosie moved and let me take a good look at myself in the mirror. I could not recognize myself. I was so femme. My face looked exactly like a girl's.

"Okay, I think it's dry, so you can probably change into these," Hannah said, handing me a baby blue thong, a black bralette, a pink skirt and a blue robe. "We did our best to get you baby blue. Molly even sacrificed her robe, although if given a chance Molls would just be butt naked all the time." Hannah laughed. Molly didn't disagree with her.

"Welcome Michelle!" Brie exclaimed. "So, shall we get this girls night started?"

I could not even dream of what was going to happen next. We made our way to the living room while we started drinking. Some of the girls has started taking selfies and while I tried to hide from them, they eventually found me. After some coaxing and pleading from my side, they agreed that no photos from tonight would ever see the light of day.

"Okay, one last shot and one more selfie before truth or dare!" Hannah yelled as we all huddled around the camera once again.

I could feel the alcohol getting to me. I no longer felt overly conscious of myself, despite still being vaguely aware that I was in a very weird situation. There I was, in front of my ex-girlfriend and her hot friends, wearing makeup, doing shots and celebrating.

"Okay," Hannah said, satisfied with the final picture. "Now is time for the main event. Circle!"

I looked around and asked, "What's happening now?" in my new, girly voice.

Rosie had taught me how to speak more like a girl It involved changing my pitch and talking slower. According to Molly, I was doing okay.

"Truth or dare!" Molly exclaimed. "It's a tradition! Come on, everybody knows 'truth or dare!' The only difference is, we drink! If you chicken out of the first one, you drink. If you chicken out of the second one, you drink twice! If you fail the first one, you drink twice! If you do the first one, the person who came up with the question or dare drinks twice, yadda yadda yadda, drink drink drink. It's really simple, Michelle. People get drunk super fast - and things get raunchy sometimes." Molly seemed especially excited about that last part.

"I bet you twenty bucks Molly takes her clothes off first," Brie said, ribbing me through my satin robe.

I had not anticipated them to react like this to the new me. I'd thought they would ridicule me and humiliate me - and, while there was plenty for me to be humiliated by, apart from a few remarks from Molly and Brie, they didn't go out of their way. Overall, they made me feel good - like I was just another one of their girls.

"Alright, enough boring rules talk," Hannah said. "Gather round. Michelle, since you're our guest of honor, you get to spin first, if you want.""

She placed the bottle in the center of our circle. I nodded, and gave it a spin. It landed on Brie.

"Oooh ooh. I want to," said Molly.

"Sure, go for it, Molls," Rosie said. "Truth or dare, B?"

Brie took a moment. "Dare."

"Alright," Rosie said with a wink, "I dare you to..., take off Hannah's shorts.... with your teeth!"

Hannah laughed. The other girls hooted.

"Easy peasy," Brie said. "Ready whenever you are, Hannah."

Brie and Hannah both stood up. Brie quickly swooped down, holding Hannah by her waist, and bit her shorts, quickly pulling them down in one swoop. Hannah was left in her thong, and started blushing.

"I'm not gonna lie, that was hot as fuck," Hannah said, taking her shorts. "Do I need to keep these off?"

"That's up to you," Rosie said. "Brie bets Molls will be naked first. You can keep it off to prove her wrong!"

Molly blew a raspberry at Brie.

"Alright Ros," Brie said, "Drink up, bitch, and spin when you're done."

Rosie bottomed her margarita, which I supposed was enough to count as two drinks. She spun the bottle, and it landed on me.

"Alright, Michelle," Molly said, pointing at me. "Truth or Dare."

For a second, I didn't know what to do. I didn't want to get too physical with anyone - well, I did. My dick was straining against my panties, and I was actually afraid I might burst if anything happened.

"Truth" I uttered, hoping I would get an easy one, like, 'ow many girls have you slept with?' The answer - two - wasn't great, but it was nothing compared to what I'd already endured.

"Alright," Molly said, "Here's a question for you. Who here would you most like to sleep with? Hannah doesn't count. You've slept with her already."

"Does Hannah not count, though?" Brie countered. "Mike slept with her, not Michelle." That solicited giggles from the other girls.

"Okay, fine," Molly said. "You can say Hannah too. But if you only pick her, you'll need to drink, because that, ma'am, is a cop out."

I could feel the alcohol I'd already downed rush to my head. I took a deep breath and counted it out in my head. I would have loved to have slept with Brie, but she wasn't into guys. Molly would be cool too, I supposed, but I actually liked Rosie as a person. She was the kindest to me.

"Rosie," I said. Rosie immediately blushed.

"Liar," Hannah said. "I know you found Brie the hottest amongst my friends."

"Yes, but she won't sleep with me because-" I began, but Brie interrupted me.

"Well that was before I found out you had the best ass amongst us all," she interjected. "And honey, as long as you don't try to stick that clit of yours in me, I'd do you any time, any place." She gave me a wink, and my dick twitched in my panties.

"So she did not answer that truthfully," Hannah said, "So she has to drink. Sorry, Rose. I'm sure she'd love to sleep with you, but Brie is definitely higher on her list."

Hannah handed me my drink. She stared at me expectantly until I'd downed enough to count as a double.

"Okay, Imma spin," Rosie said, spinning the bottle, which landed on Hannah.

"Okay, Hannah," she said. "Truth or Dare?"

"Truth," Hannah replied quickly. "I Don't think I'm drunk enough for a dare yet."

"Okay," Rosie said. "Was Mike the best sex you ever had?