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Make sure to read Part 1 first. Even though Part 1 doesn't contain any sexual activity, it's short and it's important to get the background for these characters. This chapter also has a slow build, but that's the path the story decided to take :) Towards the end of this installment however, we get our first release. I hope you enjoy it as much as my characters do!
Parts 3 and 4 (might even be a 5) will follow shortly and those will be shorter and raunchier since we'll already be familiar with Sasha and everyone else.
All characters are at least 18.
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Come Monday afternoon, I was in my room staring at the ceiling. I had just come home from school and I was in a bad humour. It had been an awful day, I had practice early in the morning, then a full day of classes, but I felt all out of sorts the whole day. Firstly, I ran some of my worst times in practice that morning so coach was already pretty cross with me. After training, he pulled me aside and gave me a whole speech about how I should start training for the 3,000m as well, on top of my training for the 800m and the 1,500m, which I absolutely did not want to do because I didn't want to lose focus. He kept on talking about building my aerobic base and my endurance, which will help me for the 800m as well, but, honestly, I stopped listening to him pretty soon. I think he was being pressured by the school to register a 3,000m runner in the next event and I was the closest to maybe achieving that.
The only reason why I started doing track and field was because Dick was pressuring me to get into sports. Apparently, I was too much of a sissy boy and needed toughening up. (Guess he was half right on that one!) He initially had me try out for the basketball team, but it only took one training session to realise that I would have absolutely hated any kind of team sports. The locker room atmosphere was something that I wanted nothing to do with. Jacked up bullies trying to out alpha male each other constantly. I almost had a panic attack right then and there when I realised that I had to come back. Luckily, Andi was already doing track and field at our high school and, even though Dick thought it was still a bit sissy to just run around in a circle, I told him that this would strengthen our sibling bond and, as he liked to preach constantly, family comes second only after god, so he saw a silver lining in that. Obviously, there was still a locker room in track and field as well, but since we were individual competitors in different types of races and with individual training, we tended to keep to ourselves. There were no cliques, more like groups, but nowhere near as bad as in team sports and if I didn't want to engage with people, they left me alone which suited me just fine.
Now, I would be lying if I said I didn't grow to enjoy it. There was something liberating about running alone, mind empty of thoughts, and I did get a kick out of the physical effort as well. All in all, it had become one of my favourite things to do. They put me in middle distance running due to my body shape: tallish, slim, with a narrow torso and long limbs, and very little fat. And pretty soon I got really good at it. Last year, I qualified for the state event and this year I was in with a chance at a medal. For a hot second, I had hoped that I could get lucky and get a full scholarship for college and get to move far from home, but my coach brought me down to earth when he told me that full scholarships for track and field were almost unheard of. I still depended on Dick and Gina to go to college, and only where they allowed me to go.
After practice, I had a full day of classes, but I couldn't focus on anything and mostly day dreamed the whole day. The worst part was when our Biology teacher caught me staring out the window and called me out and I had no idea what was being discussed. He almost gave me a bad grade which would have been a disaster since I needed good grades in Biology. Luckily, I narrowly escaped it by promising to write an additional paper this week. Well, it's not like I had a social life to screw up.
And now, there I was, back home, in my room, staring at the ceiling. Normally, I'd be in Andi's room, going through her drawers, but I promised her last week I would stop that. She made some promises to me, as well, but I didn't reopen the conversation with her after that. I didn't want her to freak out, or to think I'm too eager and maybe it was a bad idea to indulge me, or to hear that she had changed her mind, or... Or any of the million bad things that I could imagine. And now I waited for her to make the next step. So I scrolled insta for makeup tutorials and then tried some gender swap filters and wondered how screwed up it would be to jerk off to my feminised photos and finally I just stared at the ceiling.
About an hour later I heard movement in the house. For a second, I wondered who it could be. Andi had classes, mom had the afternoon shift at the store and dad was out of town on church business. I prepared myself mentally to go and investigate, but then I realised I didn't really care. If it was a robber, he was welcome to anything in the house. If it was a crazed murderer, even better. However, 5 minutes later I heard two knocks on the wall that separated my room from Andi's. I didn't understand what it was right away so the two knocks were repeated a few moments later. Now I remembered. It was our signal from when we were kids. Two knocks was "Are you there?" She was asking if I was home. I replied with two knocks of my own: "Yes." She knocked three times: "Are we alone?" I replied with two knocks again: "Yes." Two knocks, followed by a pause, followed by another knock meant "Can you come to my room?" "Yes."
I got up and went into her room. She was sitting on the bed, smiling.
"What are you doing home so early?"
"I'm cutting classes. We're alone till later, right?"
"Naughty, naughty," I smiled back at her. "Yes, at least until 8.30."
"I promised you something last week, didn't I?" I felt my heart jump out of my chest and my cheeks started burning. "Wow, you've really been waiting for this," she said, noticing my changing demeanour. "Who's the naughty one?"
"I'm not."
"Sorry, I'm teasing you a bit. I'll stop it."
"Oh, it's ok, I guess, I don't mind. I like this kind of talk."
"Girl talk?"
I blushed and I shook my head yes.
"Ok, so I freed up this drawer for you," she said, opening an empty drawer in her dresser.
I could barely contain my excitement. I was tilting on the balls of my feet and I was holding my hands by the tips of my fingers in front of my lap.
"Calm down, you little slut, or you're gonna explode."
My eyes were wide with shock, I'd never heard her use any word remotely close to that one.
"Hey, you wanted girl talk," she shrugged. "And just so there's no misunderstanding, you use that word affectionately and only with very close girlfriends. You never use it to shame someone, ok?"
I nodded dutifully.
"Ok, let's get back to business. We want to have as much time as possible to play around. So, let's see what we put in this drawer, ok? Let's start with the ones you've... umm..."
"Ruined," I finished her sentence.
"No, no. Don't say that. The ones that have been stretched. I guess we'll start with these ones," she said, holding up the pair that I was wearing the other night. They were a pair of white cotton cheekies with red cherries printed on them. "Are these your favourites?"
"I like how my butt looks in them," I said sheepishly.
"Well spotted, babe, that's what this cut is for. Ok, so these go into Sasha's drawer."
I felt my chest warming up, not just because she had just gifted me my first pair of panties, but because she was using my name.
"Ok, what's next? Tell me which pairs you used the most."
"The pink boy shorts," I whispered.
"Can't let go of old habits, I see," she said as she moved them into my drawer.
"They're... umm... functional. I can tuck better in those."
"Oh, makes sense. Ok, one more."
"Oh, my gosh, Andi. You're giving me three pairs?"
"I'd give you all of them, honey, but you know how little money they give me."
"I'm fine with two pairs, really. It's more than I ever dreamed."
"Nope, pick one more. This is not negotiable. Besides, I told you, I'd rather not wear the ones that you... played in, you know. So tell me which pair you used the most."
"The black g-string, with trim lace."
"Well, you're definitely a little slut," she said and then she added, "These are a great choice," with a hint of regret.
I realised immediately that those must have been her favourites. I was such an idiot. Of course they were. I can't even imagine how she got those past Dick and Gina, but they were definitely never going to let her buy a second pair.
"You know what, I changed my mind."
"None of that," she said curtly and she put them in my drawer. "Well, I feel like I'm building a dowry for my daughter," she laughed. "I hope you'll be happy wearing them."
"Oh, my gosh, Andi, you are the best little slut in the world," I said with tears in my eyes and I gave her a big hug.
"That's not how you use it. But I appreciate the sentiment," she laughed and hugged me back.
I held her in that hug more than I normally would have, but she deserved it. When we finally broke it, I moved in front of the drawer, my drawer, and stared into it like it was a chest full of gold. I could start wearing them again, this time with no guilt that I was ruining Andi's privacy. I moved my hands inside the drawer and, one by one, felt them in my hands, I traced their shape, felt the texture of the material, fingertips tingling with excitement. My preciouses.
"I promised you something else, as well, remember?" Andi broke my reverie.
I hadn't dared to hope that she would actually do it.
"Noo!" I said incredulous.
"Yes," she replied with glee.
"Noo!" I said again with a big smile on my face.
"Yes," she smiled and clapped her hands.
"Get outta here!"
"In a second, after I give you your present. And then I'll get out and let you change."
And with that she produced a shopping bag that had been hidden behind her bed.
"Now, before you get all excited, there's nothing spectacular in this bag. No Victoria's Secret. It's two cheap bras. I wish I could have gotten you something better. Every girl remembers her first bra."
"Gimme, gimme!" I was bursting with excitement and I practically ripped the bag from her hand. I couldn't care less about expensive bras, I wanted bras that were mine, no matter how cheap they were. I opened the bag like a kid on Christmas morning who can see from the shape of the wrapped box that they got exactly what they wanted.
Inside the bag were two bras, a black one and a white one. I picked the white one and took it out of the bag.
Andi started to explain, "This is a..."
"A bralette," I interrupted her. "A lace bralette. Oh, my gosh, I love it," I yelped. I held it up in front of my chest and moved in front of the full length mirror mounted on one of the walls. "I love it," I yelped again and I jumped up and down a couple of times. I didn't even care how I sounded.
I dug in the bag and pulled out the second bra. "I don't know what you call this," I said. In fact, I knew what it was called, but I realised that I wanted Andi to share my excitement.
"Yey, I can teach my baby sister something." She clapped her hands excitedly. "This is called a balconette bra. See the horizontal cut, it's only half-cup and it's supposed to just cover above your nipple. And it has these thin straps, they're called spaghetti straps. And, oh my gosh, this bow in the middle, I just love this bow, it's so cute."
"It's so cute," I screamed with her. I put it against my cheek and two big tears rolled down. Gosh, I was crying so much lately. But I didn't care, they were tears of joy, for once.
"Ok, I'm gonna go downstairs and let you change. And then, if you want, you can show me what you chose."
"Don't go. Please, stay here."
"I don't want to see you naked. Really."
"You can just turn around when it's time, I don't want to do this without you."
"Ok, if that's what you want."
"Ok, before I start... Gosh, where do I want to start? So many choices." I picked them all up and turned them all around and inspected them carefully, one by one, both of my bras and all three of my panties. It may not seem much to you, but in that moment I felt so spoilt for choice.
"Ok, so, I love the balconette, it's so sexy. And that goes best with the g-string. But I also like my cheekies and I think that goes best with the bralette." I took a deep breath as I pondered my choices. "I don't know, I don't know," I yelped again. "Ok, ok, the bralette with the cheekies," I finally made a decision. If I were alone it probably would have taken me longer to decide, but I didn't really want my sister to see me in a g-string. Not for my first viewing. "You can turn around now."
As Andi turned around I quickly dropped my shorts and boxers. I picked the panties and slid them carefully up my legs. I tucked my penis as best I could inside them and then I ran my fingers along the leg openings and then along the elastic band, making sure that they didn't crumple anywhere and that they fit neatly across my ass. Gosh, I loved how they made my ass perk up. And I loved feeling the fabric across my skin. I was starting to get an erection so I had to think unsexy thoughts to make it go away, which took a few moments.
"Are you done?"
"No, not yet, just enjoying the feeling."
"Well, finish up and enjoy it afterwards. I can't wait to see you."
I then dropped my t-shirt and picked up the bralette. I slid my arms slowly inside the straps, trying to savour this moment as much as I could. I then struggled a bit trying to fasten it, but I figured it out pretty quick. I smoothed the lace across my chest and then ran my fingers along the straps and the band to make sure they weren't twisted. It fit so well on my chest. With all the training I was doing I had a bit of definition in my chest and the small cups were, well, cupping my barely existing pecs just right. And feeling the bra brush across my nipples made them a bit hard and gave me that warm feeling in my tummy.
"Ok, keep it together, Sasha," I thought to myself. "No erection." I took another deep breath and I calmed myself down.
Ok, I was ready. Ready to be seen for the first time dressed in a way that felt right to me. I tried to strike a sexy pose before I called for Andi to turn around, but my mind was blank. I finally turned a bit to the side and bent up one knee slightly. "I'm done, you can turn around now."
"Oh, my gosh, you look so pretty," she said as she covered her mouth in what I hoped was astonishment. "You're such a pretty girl, Sasha. And your ass really looks good in those panties. Better than I looked in them. Wait till we find you a pair of high heels that fit. Those will push your ass out even more."
"Thank you, Andi. This is all because of you. I'll never forget this," I barely muttered before I started crying again, prompting Andi to start crying as well. She took a step towards me and gave me a hug and I hugged her back as we were both sobbing.
"Oh, my gosh, we're crying like a couple of bitches," I said.
"Yes, yes, we are," she laughed through her tears.
"Thank you, thank you, thank you."
"And thank you for giving me a little sister. Don't get me wrong, you're a great little brother, but I'm so excited I get a little sister, too. Someone I can teach how to be a woman and impart valuable words of wisdom to."
"Admit it, you wanted a live sized doll, didn't you?"
"So what if I did?" she smiled at me cheekily. "Don't I deserve something, too?"
"No complaints here. I'm happy to be it."
"Ok, let's get you in front of the mirror now so you can see what I'm seeing," she said after we wiped our tears.
I took a deep breath and stepped in front of the mirror with my eyes closed. I took another deep breath and opened them, getting a look at Sasha myself for the very first time. A mix of excitement and disappointment washed over my face. I guess it was pretty noticeable, because Andi saw it immediately.
"Oh, no. You don't like them? It's ok, I can take them back and get you something else," she worried.
"No, no, that's not it," I said as two tears rolled down my cheeks again, only this time in frustration.
"Really, I can take them back."
"No, really, it's not the bra. I love it. It fits so well."
"Then what is it? Is this not what you were expecting? It's ok if you don't actually want to dress up."
"No, that's not it either."
"That's the thing with fantasies, we build them up in our mind and when we actually do them we realise that they were just that, fantasies. I had an experience like this myself. I thought I wanted to do something so much, that was all I could think about and when I did it, well, I just wanted it to be over as quickly as possible."
"No, really, it's not like that. I like the clothes and I like being in them. They feel so good. And so... right, you know. It's just..." I couldn't finish the sentence as I chocked up on another round of tears.
"What is it honey? You can tell me."
"It's just... I feel so good in these clothes, but when I look in the mirror I don't see a girl. I see a guy in a bra," I said before I started sobbing uncontrollably.
"Oh, honey. That's not... That's not something to worry about now. It's your first time dressing up."
"And what, I'll magically turn into a girl the second time?" I bawled. "Look at... that," I said pointing at the mirror, "it's so ugly."
"Don't say that. You are not ugly."
"This was a bad idea. I'm not a girl! I'm just confused. Dad was right, I'm just weak, I need to man up."
"Stop it. He's not right. You don't mean that."
"I do. This is wrong. I'm a disgusting pervert. Gosh, I'm gonna be sick."
"It's ok, honey, it's ok. Let it all out," Andi said and held me at her chest until I finally calmed down.
"Listen, I have an idea."
***
Saturday morning, Andi and I were on our way to Bianca's house, one of Andi's best friends. Chris, her other best friend, was also going to be there. How did I let myself get roped into this?
"Let's go back. I changed my mind."
"It's too late, they already know."
Ugh, that's right, she already told them. Why did I say yes? Remember when Andi said she had an idea? Well, I couldn't really feel like a girl looking like I do and we couldn't do a makeover session at home. First of all, it was too risky, Dick or Gina could come home early unannounced and there wouldn't be time to clean up before we got caught. Second of all, Andi had very little makeup of her own because Dick and Gina didn't like her using any at all. In fact, she wasn't even allowed to use any makeup until she turned 18. I remember when she was about 14 and tried on some of Gina's stuff and when she got home and saw her, she yelled at her for hours, calling her words like "trollop" and "jezebel". Dick would straight up kill me if he saw me like that.
Apparently, Bianca and Chris helped Andi a lot. She would get invited almost every weekend for a "slumber party" at Bianca's and those were actually makeup parties, where she was free to use their makeup and they would teach her what to do. Bianca's parents were aware what the situation was in our house and were more than happy to accommodate Andi whenever she needed.
So, Andi's idea was to organise my first makeup party at Bianca's. Now, we had to do this during the day, because I couldn't say that I was going to a girl's house for a sleepover (duh!), but we picked a day when they were out of the house and that meant that we had a full day to play around. Gina would be pulling a double shift at the store this Saturday because another one of their employees had quit with no notice (gee, I wonder why) and Dick was, again, away on church business, whatever that meant.
As excited as I was, this also meant that I had to let Bianca and Chris in on my secret. Which was really hard for me to do. I didn't know them as well as Andi. I knew them a little because, at one time or another, they had both been in our track team, that's how Andi met them. Chris was one year older than me, she was already a freshman in college. Bianca was the same age as me, still a senior in high school. They were all right as people and they were Andi's friends, but they weren't my friends. And the risk of one of them letting out this information about me, even by mistake, was the thing that I dreaded the most. Especially since Bianca was still in high school with me, imagine word getting out, my life would be over.
Oh, and truth be told, I had a little crush on Bianca and I wasn't sure if I wanted her to see me like that. Not that she would ever be interested in someone like me, she was dating a pack of meat from the football team, but I still didn't know how to feel about the fact that she would see me as not a man at all. But, in the end, did I want to be seen as a man? Fuck, man, I don't know. It was all very confusing.
Eventually, I decided that if Andi trusted her friends, then I would trust them, too. Also, my desire to go through a full transformation was too big to ignore. So, there we were, Saturday morning, Andi and I, knocking on Bianca's door, Andi with a big grin on her face, me with a huge pit in my stomach.
"Morning, bitches!" Bianca yelled as she opened the door.
"Morning, bitches!" Andi yelled in response and the three of them hugged.
"Uhm... hi!" I said.
"Oh, look at her, so shy," Bianca teased me. "Come here," and she pulled me into their hug. This lack of inhibition on their part made me feel less apprehensive. I thought that it would be awkward af and we would all tiptoe around the elephant in the room, but they seemed all right with what we were there to do.
"Well, come on in, come on in," Bianca continued, "I made mimosas for everyone. That's champagne with chilled orange juice. Don't worry, there's just a little champagne and a lot of orange juice." Those last two remarks, she looked straight at me, she probably knew that I'd never had any alcohol.
We all picked up a glass and they yelled, "Makeup party!"
"Makeup party," I mumbled after them. I was basically keeping an eye on the door, wondering how weird it would be if I just ran away.
"Makeup party and dress up party," added Bianca looking at me up and down.
"So, don't freak out," Andi said when she saw my eyes widen in panic, "but we thought maybe we could try more than doing your makeup today. I know I'm too petite for my dresses to fit you, but Bianca here is more similar to you. Ok, maybe you're a couple of inches taller, but otherwise, you have the same body shape so maybe you could fit into one of her dresses."
"We'll see," I mumbled again.
"Yeah, yeah, we'll see and then we'll dress," Bianca said. She looked into my eyes dead serious, "I'm gonna make the prettiest girl out of you and you will not deny me," and then she giggled. These girls were on a mission today and I was their plaything.
"Ok," I said sheepishly. "Uhm, are your parents home?"
"No, and they're not coming back anytime soon. Listen, I promise you no one will know unless you want them to know. I made you a promise and I'm taking this shit very seriously."
"Thanks."
"Thank me when we're done, honey. And relax a little, don't be such a hedgehog."
"Well, you girls go upstairs and get started, I'll make a fresh bunch of mimosas," said Chris.
Stepping into Bianca's bedroom was like stepping inside a gum bubble. The walls were a light pink hue, her bed frame was white and she had pink sheets, the chairs were white with pink fabric, a pair of pink panties was hanging from a corner of her vanity table. I guess I shouldn't have been surprised, Bianca favoured pink in her makeup, her blonde hair and milky white skin went really well with her pink eye shadow and her pink nails. Was this how all girls' bedrooms looked like? Andi's was far more spartan, but I guess that was to be expected in our house. And obviously I'd never seen another girl's bedroom before.
Andi and Bianca sat on the bed with their legs crossed under their bums and I just looked around feeling like I didn't belong.
"Ok, let's see what we're working with," Bianca said. "Alex, have a sit here. Sorry, I meant Sasha. Sorry, I'll get it right."
"It's ok. I think Alex is ok when I'm in boy clothes. Less confusing."
"Ok, makes sense. I'll remember that. Sorry," she apologised again. She was obviously embarrassed by what she perceived as a faux pas, but I didn't know what else to say to make her feel better.
"Actually, before we get started," Bianca said, "you should go and take a shower. You can use anything you want in my bathroom."
"I took a shower before we left home," I protested.
"Honey, I'm not saying that you're dirty or anything like that, but when you come out you'll smell more like a girl, you'll feel better like that. Also, you need to shave your body. I left a new razor in there for you."
"Nooo," I said, voice filled with panic.
"Remember how you said that when you look in the mirror you see a guy in a bra?" interjected Andi. "This is one is pretty high on the list."
"What if someone notices?"
"You'll wear long sleeves for a few days, it's gonna be fine."
"Ok," I relented, but this still felt like going to far.
"Ok, so, after the shower, you'll shave everywhere," Bianca continued. "And I mean everywhere. Even down there," she said pointing at my crotch, "and back there," pointing at my ass.
"Really? But nobody's gonna see there, not even me."
"Alex, this is about feeling like a girl. And you're not gonna feel like a girl with swampy hairy ass. Trust me."
"Oh, yeah, you can't have a hairy ass," added Chris as she was entering the room with a tray with four glasses freshly filled with drinks.
"Ok," I replied unconvinced.
"Good. So, shower, shave and then use the moisturising cream that's on the sink. Use it all over the body. It's going to help prevent itchiness and it makes your skin feel smoother. Oh, there's a fresh towel in there for you, the pink one." Of course it was pink.
"Got it."
"If you have any questions, just open the door and yell. Ok, girl?"
"Ok," and with that I made my way towards the bathroom, shuffling my feet, like a criminal heading for the gallows. This was too much.
"Hey, trust me, you'll feel better when you come out," said Andi as I was walking out of the room. I guess they weren't making fun of me, they were really trying to help.
I took a quick shower, and Bianca was right, her shampoo smelt so nice, so feminine that I was starting to feel less anxious about the whole thing. I then lathered my whole body with shaving cream and started shaving. Arms, chest, legs went pretty quickly. As I was going lower from my chest to my belly, I was starting to feel nervous again. I shaved the fuzz below my navel, then gently started shaving my pubes. I moved the razor carefully around my penis, then even lower to my sack, very careful not to cut myself. I wanted to be a girl, but not to that extent. Before I moved on to what was to be the biggest challenge, I took a look at my back in the mirror. I actually didn't know if I had any hair there. Turns out there was some on my shoulder blades. "Goddammit," I thought as I contorted my body to reach it. And then some more fuzz on my lower back, just above my ass. I contorted some more and got rid of it, too.
Only my ass hair was left. I tried reaching around, but I couldn't see a way to make it work. Maybe I'll just leave it, they're not gonna know. But what if they see it somehow? They're doing all this for me and I can't commit fully? But how do I do it? Since I couldn't think of a way, I opened the bathroom door just a little and called softly.
"Uhm... Bianca?"
Nothing. I could hear them across the hallway, talking and laughing and clinking their glasses.
"Bianca?" I raised my voice a little. I didn't want to shout, but they definitely couldn't hear me. "Bianca!" I called a little louder.
"Shh, shush," I heard Bianca react in her room. "Shut up. I am needed. Step aside," and she appeared in her door frame.
"Yes, honey, what do you need?"
"Do you have some of that cream that is used to remove hair?" I asked hopefully. "I don't know hot to get behind there and I don't want to cut myself."
"Oh, no, you don't want that. Not the first time. It really depends on how sensitive your skin is, you could get a nasty burn. Really, the razor is your best option."
"Uhm... I can't reach?"
"You gotta put a leg up on the tub, then reach back with one hand to spread your cheeks and use the other hand to shave. I know it seems difficult the first time, but trust me, it can be done. I've done it so many times by now. Hey, don't tell anyone else, but I have a pretty hairy ass myself."
I heard giggles from Andi and Chris.
"She does. We've seen it," they both shouted from inside the room. I giggled a little to myself, they really saw me as one of them.
"Ok, I'll try. Can you wait there for just a second? Till I give it a try?"
"Yeah, sure. I'll be just outside."
So I closed the door and did as instructed. Put a leg up on the tub, spread my cheeks with one hand, used the other to lathe, then picked up the razor, then leant forward to get a good angle and... fuck me, I slipped. At the last moment I managed to grab the sink so I didn't fall down, but that meant that I had to drop the razor, which fell on my foot as it was sliding under me. I managed to stop myself and regained my balance. Nothing happened, but it was close. I could have been lying on the floor with a cracked skull and a cut up foot.
"Are you ok?" Bianca said worried. "Do you want me to come in?"
"No! I'm fine! I don't think it's working."
"Do you want me to do it for you? It's ok, really."
"Nooo! No, thank you. Absolutely not."
"Ok, well then, try to dry the floor a little, get better balance and try again. It's really no hurry and you're gonna have to learn how to do it at some point. Might as well learn now."
"Yeah, I guess." She made a good point.
Attempt number 2. Put leg on the tub. Spread cheeks. Lathe. Try to shave. Ok, this time I managed to do one small swipe with the razor. I was all sweaty and felt like I was about to pull something, but I'd done it. And little by little I made progress, while Bianca was guiding me from the other side of the door. At one point, she even got into an argument with the other two girls.
"Hey, what's going on there? Can we help?" they yelled from the bedroom.
"Stay there, it's all under control," Bianca replied from the hallway.
"Hey, if anyone's helping her shave her ass, it should be me, I'm her sister," yelled Andi.
"No one is helping me shave my ass, I'm doing it myself," I yelled from the bathroom and all three of them giggled. I giggled, too. It was funny, to be honest.
"Ok, I think I'm done," I announced after what felt like a couple of hours.
"Yey, you can come out now," Bianca replied.
"I think I need to take another shower, I've been sweating like a pig."
"Well then, take your time, we'll wait for you in my room," Bianca said. "Hey, give me your clothes."
"What do you mean? I'm not coming out naked."
"You're not putting your stinky boy clothes back on either. You can wrap the towel around you. That's how a girl comes out of the bathroom anyway."
I begrudgingly agreed and gave her my clothes. If this is a prank... no, stop it, no one's pranking you, stop doing this to yourself.
A quick shower and another round of moisturising later, I wrapped the towel around my hips and came out. I even tried to style my hair a little more feminine, but it was way too short to do anything with it.
I knocked on the bedroom door and announced myself. "Hey, I'm coming in."
"Oh, did you hear that girls, the princess is coming in," Chris mocked me, but in a playful manner, not a mean one. "Come in already, we're dying to see you."
"I don't really look all that different," I said as I stepped into the bedroom.
"What are you talking about? Look at your skin, it's glowing. And you smell so nice," they all chimed. I looked at the floor and blushed.
"Oh, look how bashful she is. You're just so adorable," Chris commented.
"Ok, now take a deep breath and lose the towel," said Bianca. "Don't think about it, just do it."
"What are you talking about?"
"Well, first of all, it's all wrong. A girl fixes her towel above her chest, not around her hips. What are you doing with your tits out?" Bianca said and they all giggled again, even me.
"Second, we need to see if you did a good job shaving. There's nothing to be embarrassed about, we all do it with each other." I looked at Andi questioningly and she nodded a "yup, that's what we do".
"Third, we have to see what we're working with so we can build a look for you. Do you want me to continue? I've got like nine other reasons."
"Hey, nobody's pressuring you to do anything you don't want to. We can stop everything if you're not comfortable. Just don't say no because you're embarrassed. You're with friends here," added Andi.
I closed my eyes and let the towel drop.
"Ok, not bad," said Bianca as she looked me up and down. "Can you stand on your tippy toes for a second, just to get an idea what you would look like in heels?" I did as she asked. "Ok, that's enough." Then she took my hands in hers and lifted them so they were shoulder height and she turned me a little to the left, then a little to the right.
"Ok, ok, not bad at all. Give us a spin, babe." Again, I did as instructed.
"Oh, wow, look at that ass. Girl, you're making me jealous."
"Stop it, you don't have to..."
"I'm not, you have a good body shape. Tall, lean, flat stomach, just enough of muscle, a great ass. All that running worked out great for you. Slap some tits on you and you could be on a catwalk somewhere." I blushed for like the hundredth time that day and definitely not the last.
"Yeah, and look at that clit," said Chris whose eyes were glued on my penis.
"Hey! Stop that!" Andi was shooting daggers out of her eyes at Chris, but I kinda liked her calling it a clit, I'd never thought of that.
"What? I like what I like. Don't shame me."
"Don't listen to her. She's always inappropriate."
"Ok, ok, show's over," said Bianca. "Put some panties on. Did you bring anything or do you want me to give you a pair?"
"No, I brought my own," I said and I pulled my black g-string from my backpack and put them on quickly. For the first time in my life I appreciated the difference a shaved ass makes. I could feel the thin piece of fabric snuggle tightly between my cheeks. The front, however, didn't offer much protection, a little excitement and I would spill out quite easily.
"Are those...," Bianca started, looking at Andi, but Andi shut her out quickly. "Those are hers." God, I really stole her favourite pair of undies. I have to make it up to her somehow.
I also took out my black bra and put it on.
"You look very pretty," was the consensus around the room and, now that I had my girlie underwear on, I felt more at ease. I rubbed my hands over my exposed skin, my arms, my belly. It felt so good without any hair on, so soft, so velvety. I still looked away from the mirror, but I felt like this was one step in the right direction.
"Ok, babe, have a seat in front of this vanity," said Bianca, "and let's get going on the makeup. I'll do my own makeup and you just follow along. I'll try to explain what I'm doing, but you don't need to learn everything today. Remember, it took us all of our teen years to learn how to do it right and what works for each of us. When you're going to try it alone, it won't look perfect for some time, but the important thing is to not feel like you've let yourself down. Practice, practice, practice. You know, like coach says." We all groaned at the mention of coach. "God, you have such a beautiful structure, with those high cheekbones, those full lips, oh, I could just eat you up." I felt my cock jolt a little in my panties at the thought of her mouth molesting my face. I took a deep breath and tried to calm down.
I sat down on the chair, face to face with Bianca, heart pounding in my chest in anticipation.
"So, the first thing you have to learn is to do your makeup for the occasion. At first, you'll feel like you want to put everything on, otherwise maybe you'll still look like a boy, but you'll actually achieve the opposite effect. The more makeup you put on, the more you attract attention. Now, if you're going to a party, for example, you want attention. But if you're going out to the shops at 11 in the morning or just to meet your girlfriends, maybe you don't, get it?
"All you want is to cover up any discolouration, beard shadow, blemishes and so on. And you want to have a natural look. You want it to look like skin. Make sense?"
I nodded yes, but I was a bit panicky inside. Was I going to remember everything?
"Ok," Bianca continued, "the first step when you do your makeup is not makeup. It's moisturising."
She opened a jar and scooped some cream with her fingers as she continued, "You want to hydrate your skin and create a healthy base for the primer and the makeup." She rubbed some cream on her face, making sure she covered every inch and then she handed the jar to me and I copied her.
"Ok, we'll let that absorb for a second." She paused briefly and then came out with it: "So, do you like boys or girls? Or both?"
My eyes widened and I felt a knot in my throat.
"If I'm being too pushy, I'll stop. But that's what girls usually do when they make themselves pretty, they talk about boys. Or girls. Andy and Chris are into boys."
"I'm not into boys, I'm into dicks," quipped Chris, plucking at her eyebrows. For the last few minutes, my attention had been focused solely on Bianca, but, behind me, Andi and Chris had started working on themselves as well.
"I mean, I'm also into boys. Mostly," continued Bianca, unfased by Chris, I guess I was learning that's how she usually talked. "But, honestly, I'm curious what it's like to be with a girl."
"Yeah, she can't wait to lick some pussy."
"Listen, bitch, I saw you tasting yourself when you masturbate. And liking it, so... Anyway, it's not about pussy. It's just that girls are so pretty..."
She then turned her attention back to me.
"I think the moisturiser was absorbed by now. Next step, we're going to use a primer. This will create a smooth layer between your face and the makeup. It does a lot of things, like filling in wrinkles, pores, helps with oil control, it makes the face crease free so you have a good canvas for applying the rest afterwards. For you, it might also help with irritation from shaving. This one that I'm using now is in stick form, so I'll just run it over my skin, all over my face."
I watched her intently as she was applying it to her face.
"I like girls, too. I think," I whispered to her. It felt awkward not to share, but I also wanted to be part of the discussion.
Bianca smiled as she handed me the stick to copy her. I guess she was pleased that I was trying to open up. "Anyone in particular?"
I couldn't tell her that I had had a mad crush on her for a few years now, but she was so close to me and her attention was focused on me so I blushed hard. She smiled and put her hand on my knee. "It's ok, you don't have to tell me."
"Ok, now we're going to apply a little colour correction. I usually use it under my eyes where I get these blue circles, see? For a girl like you, it's also useful to hide facial hair, especially if you get a 5 o'clock shadow. See, I've been doing research," she said turning to Andi.
"So, do you get 5 o'clock shadow?"
"More like a 5 day shadow," I chuckled.
"Well, that's good that you don't have to worry about that, but today we'll practice anyway. So, facial hair has like a bluish hue, just like my dark circles, so for that we're gonna use an orange or a peachy concealer. I'll take this concealer brush and just tap it where I need it and then I use my finger to blend it in. Ok, now you do it."
I tried copying her moves while she watched me intently and corrected me a couple of times. Even though I was sitting at her vanity, I didn't want to look in the mirror. Not yet.
"Ok, go light and if you need more we can add it later. We need to work in thin layers to get that natural look. Now we're gonna let this dry out completely for a couple of minutes. We don't want it to mix with the foundation later."
As we waited, Bianca continued to probe me.
"So, you have a crush on this girl you don't wanna tell us about." She paused a second to see if I was going to offer more info, after which she continued. "Any boys?"
"No. I don't think so. Honestly, I didn't think about it."
Which was a lie, I did think about it. I didn't want to, but thoughts don't care what you want, they just pop into your head and leave you trying to figure out what they mean. And yes, I know that mostly I was afraid to think about it because of how I was brought up, but that doesn't mean that you can just ignore what has been drilled into you your whole life. I did notice that I was thinking about boys only when I tried some panties on, not when I was in boy mode myself. I don't know if this meant anything, but that's when those thoughts came. When I was lying down on my bed on my belly, I sometimes imagined what it would be like to have a boy on top of me, his body pressed into mine, his lips gently kissing my neck. My dick would start to swell and I'd rub it against the mattress, at the same time wiggling my ass in the air, rubbing it against this imaginary boy.
"I think you're thinking about it right now," said Bianca, noticing that I went somewhere in my mind.
"One time... You know David?"
"David Simms? From the running team? Damn, you have good taste."
"Yeah, one time we were in the locker room..."
"And you were checking him out?" smiled Bianca.
"No, that's not it. The other guys were talking about trans girls. I don't know how that conversation started, but they were making these gross jokes, you know, it's not a chick with a dick, it's a dude with tits... Anyway, David said he didn't care, that if he liked someone, it didn't matter what sort of a girl she was. And they started making fun of him, that he was gay and so on. And he just smiled at them and said 'You're just a bunch of children' and, I don't know, in that moment, he seemed so mature and so, I don't know, attractive, I guess."
"Yeah, I know what you mean. Boys our age are just that, boys. I can't wait to go to college and meet some grown ups. Or at least a bit more grown up."
"What about Jimmy?" It was my turn to probe, I guess. Jimmy was Bianca's boyfriend. He was on the football team and he was exactly how you would expect a high school football player to be.
"He's ok. I don't want to be a bitch, cause he's nice and he treats me well. But all he he thinks about is football and sex. And I don't mind it, he's pretty good at both, but sometimes I wish we did something else together or talked about something else, at least.
"Ok, I think we waited enough. Let's move to the next step."
And on we continued. A little bit of foundation, a little bit of red blush, a little bit of mascara. The only place where we went a little bold was a red eye shadow. Bianca also wanted to pluck my eyebrows a little, but I was afraid that it would be noticeable and Andi agreed that it was a bit too risky. We finished it all off with a bright red lipstick. The moment of truth was approaching. The moment when I would have to turn around in my chair and look in the mirror. My stomach was in knots in anticipation.
"One more thing," Bianca cut off my train of thought. "I have a surprise for you," she said as she swiveled in her chair. She opened a drawer and pulled out a wig.
"It's the only one I have, I bought it for Halloween, but I think it's gonna look good on you."
The wig was straight black hair, going past the shoulders, with bangs.
"I think this kind of haircut really suits your bone structure and your alabaster skin and your black eyes."
Andi and Chris interrupted what they were doing and turned towards me as Bianca was fixing my wig. As soon as she was done, I could see shocked expressions appearing on their faces. Was this good shocked or bad shocked? I couldn't tell.
"Oh, my god, Bianca," Andi mumbled, "that's... uhm, that's..."
It was bad shocked. I knew it.
"It's fucking gorgeous, that's what it is," yelped Chris. "How the fuck did you do that? She looks... That's a girl. No way that's Alex, that's a girl."
"She's so beautiful," added Andi.
"You know who she looks like? She looks just like that porn star, what's her name, Bailey Jay," offered Chris.
"She does not look like a porn star. Are you crazy? Why would you say that?" exclaimed Andi and punched her in the arm.
"I didn't say she looks like a porn star. She looks like that particular porn star. She's gorgeous by the way."
"I don't care how gorgeous she is, stop saying that. You know who she looks like? She looks like that Egyptian princess from that movie we saw last week. The Mummy."
"Oh, yeah, she does look like her a bit. But her skin was more olive."
"I'll tell you who she looks like," interjected Bianca. "She looks like Angelina Jolie in that movie when she's a spy."
"Oh, yeah, that's right," both Andi and Chris agreed.
There was no way I looked like Angelina Jolie, but maybe it was good? I still hadn't looked at myself.
"Come on, turn around and look in the mirror. It's good, trust me," said Andi.
So I turned in that chair towards the mirror, closing my eyes as I was turning, not sure if I was ready for this moment. This was the moment of truth for me, the moment when hopes could take flight or be broken for ever. So many times I looked in the mirror, not happy with what I saw. Will I ever be beautiful? I looked in the mirror and asked myself that question since I was maybe 12. I looked in the mirror and saw something that could be beautiful, but, oh well, you're a guy, so... You could've been a beautiful woman, but, oh well...
So, I took a deep breath and looked in the mirror. And for the first time in my life, I was beautiful. I looked in the mirror and saw a beautiful woman looking back at me. Tears sprung from my eyes and I could feel my chest explode with happiness. Uncontrollable happiness.
"Hey, you're gonna ruin your...," Bianca started, but I think she realised that these tears could not be held back. "Never mind, we'll fix it afterwards," and all three of them embraced me.
***
Half an hour later, makeup fixed, I still couldn't take my eyes of myself in the mirror. I kept turning my face a little to the left and a little to the right, observing every little detail, moving a strand of hair a little bit to the side, pursing my lips, fluttering my eyelids, blowing kisses to myself... I was completely enthralled with this image of me that would be burned in my memory for the rest of my life, no matter what happened next. My instincts had been right all along, I never wanted to be anything else again. And yet, I knew that in a couple of hours this will all be carefully taken off until, maybe, next weekend.
We were a couple more mimosas in and I'd never felt better in my life. I finally tore myself away from the mirror and turned to the other three who had been chatting away, giving me time to get acquainted with my new self. I looked at the other girls and, for the first time, I was struck by how beautiful they were, each in her own way. And for the first time I appreciated how each of them amplified their features with their makeup.
Bianca was the typical girl-next-door beauty, with long blond hair put up in a pony tail, a round face with fat cheeks with cute dimples, big blue eyes, all matched very well by the pink hues that she used in her eye shadow, her blush and her lipstick. Chris was a quasi-goth girl. She had raven black hair, cut in a bob with the hair a little longer in the front than in the back, and black jet eyes. Her eye shadow and her lipstick were dark red. For her face she used a foundation that was a shade lighter than her skin tone and on one of her cheeks she drew a fake beauty spot. Andi, I'd never looked at her as a woman before, she was a bit of a tomboy, not as tall as me, but slender, with great muscle tone. Her makeup was the most understated of us all, just a touch of peach on her cheeks and a muted red lipstick. However, whatever she did to her almond shaped eyes really made them stood out and draw all the attention in the room. Her haircut was similar to the one I was sporting. Looking at her after seeing myself in the mirror really brought home how much we looked alike.
"Are you ok?" Bianca asked.
"Yeah. I'm sorry, I've been a bit self-absorbed."
"Don't worry, Sasha. We get it."
"Thank you so much. For everything, not just for the makeup. Thank you for accepting me."
She put her hand over mine and squeezed it.
"So, what were you guys talking about?"
"They're bitching at me because I only take it up the ass," Chris said nonchalantly.
"Yeah, she wants to be a virgin on her wedding night," Andi rolled her eyes.
"That's not what I said. I didn't say I'm a virgin. It's just, I want to share something special with my husband. On my wedding night. Is that ok with you?"
"So you're telling me you've never had anything up your pussy? Ever?" Andi asked in disbelief.
"Nope. Not a dick, not a dildo, not a cucumber, not even a finger. Ok, I've had tampons, but you're not gonna tell me that counts."
"You're so fucking weird."
"I get enough orgasms from my clit. And enough penetration from my ass. I'm not missing out on anything."
"Ha! Not missing out. You have no idea..."
"I don't get it. What's it to you guys how I choose to get fucked?"
"No, you're right. It's just... weird. Not even when you masturbate?"
"How many times have you seen me masturbate? You never noticed?"
"I guess I didn't."
"Aww, you hurt my feelings," she mocked and threw a pillow at Andi.
"Oh, shut up!", Andi replied with a giggle and threw the pillow back. "So fucking weird."
There was a moment of silence as we all sipped from our glasses.
"So, Sasha, do you take it up the ass?" Chris turned to me.
I snorted my mimosa out the nose and looked at Andi, panicked.
"What? You're a big girl," Andi shrugged. "Share what you want to share."
"I... uhm, no." I made a pause. "Actually, I've never had sex."
"Wow, so you must jerk off a lot. Especially with your... you know, your junk," Chris continued casually, vaguely pointing at my dick.
"What do you mean, with her junk?" Andi intervened quite angry.
"I don't mean anything. I'm not saying she's a boy, it's just... she went through boy puberty. With boy junk. And you know how much they jerk off... the people with penises?... teens with penises?... what? they do!"
I didn't take offense at anything she was saying. It was a fair question, and quite amusing, the way she worked her way through it.
"Yeah, I guess I jerk off a lot."
"Yeah, me too. What's your personal best?"
"What?"
"You know, how many times in a day. I once did it 10 times in a day."
"10 times? I think my 'junk' would've fallen off," I replied to everyone's amusement. "I don't know, 6 I think. But the last one, I was shooting dust."
"Dick's are so weird, man," mused Chris.
"Fun, but yeah, weird," added Bianca.
"Did you ever taste yourself?" continued Chris.
"You mean my sperm? Yeah, a couple of times."
"How was it?"
"Actually, kinda bland. A bit salty, a bit... metallic... i guess...? I don't know. It wasn't very memorable. To be honest, I liked the texture more than the taste."
"Ha, me too. I don't get all the girls who say it's gross. I like how it coats my mouth, especially when they come a lot."
"Apparently, the taste depends on like diet and other stuff," I continued.
"Yeah, I heard that too. I've been trying to get my boyfriend to eat more pineapple. It's supposed to make it so much better."
"I can run an experiment if you want," I offered as a joke.
"Of all the things you could've bonded over," Andi interrupted, "the taste of sperm was not on my list. Although, with you, Chris, I shouldn't be surprised."
"Listen, I know I overshare a lot. But I like sex. And you guys are my friends."
"No, you're right. I know I'm a bit of a prude sometimes also. Still trying to shake off what I learned at home."
"Have you tasted pussy also?" Chris returned her attention to me.
"No. I told you, I'm a virgin. Probably the only 18 year old in the world who hasn't had sex yet."
"Nah, don't worry about it. You had more figuring out to do than the rest of us. You'll find somebody. Soon, I'm sure."
I gotta say, the way this group accepted me, it was making me even happier than the makeover. They could've said yes to this afternoon just to accommodate Andi, but they seemed very genuine towards me. It made me feel more like a girl than that image in the mirror.
I was getting more and more relaxed with the conversation (the mimosas probably helped, but I was also getting more comfortable), but I didn't expect the next thing that Chris was gonna say.
"Hey, guys, remember when we used to finish our makeup parties with a session of group masturbation? Let's do that! You know, give her the full experience."
"I think she had enough experiences for today," Andi replied curtly.
"Why not? It's fun!"
"I'm not masturbating next to my little sister. No way!"
"So you're telling me if she was born your little sister from the beginning and she came with you to our parties a couple of years ago, you wouldn't have done it?"
"That's different."
"How?"
"Yeah, how?" Bianca chimed in.
"I don't know. It just is."
"I think you're still thinking of her as she used to be," continued Bianca.
I was going to intervene on Andi's behalf, I didn't really want to jerk off next to my sister either, but before I said anything Bianca continued: "I think it would be good for her. You know, add to her feminine experience. Besides, now that it's on the table, I kinda want to do it, too."
The thought of seeing Bianca masturbating next to me made my dick wake up. Actually, a couple of seconds later it was straining the tiny piece of cloth that was having difficulty hiding it anymore.
"Look, she wants it, too," Bianca said, pointing at my penis. I instinctively covered it with my hands before it popped out due to too much attention.
I turned to Andi and said, "If you're not comfortable with it, we're not doing it."
"Do you want to?"
I shrugged and looked at her pleading with my eyes. Yes, I wanted to. I'll be honest, I don't know if I wanted to because it was another feminine experience that I could tick or just because I really wanted to see Bianca naked and she just pointed at my dick. But I really, really wanted to.
"Ok, why not, I guess?" Andi conceded.
"Yey, jerk off session," yelled Chris. "I call the bean bag."
"You can take the head of the bed," Bianca said to me, "and I'll take the foot. And, Andi, you can take that chair, that way you and Sasha won't be directly in each other's eye line."
Ok, so I'm sat at the head of the bed, legs crossed under my bum, a boner that's already spilling out of my panties and freaking out of my mind. Now what? Luckily for me, nobody cared. Chris was out of her clothes before I could blink and was getting comfortable on the bean bag. Bianca was down to her panties and was caressing her belly. I involuntarily took a peek at Andi as well, she was still fully clothed, her eyes were closed and she was massaging her breast through her t-shirt. I released my cock from the confines of my tiny g-string. I was super hard.
I started to stroke it, but it felt no different than what I usually did. Shouldn't it feel different? I took another peek at Chris, she put two fingers in her mouth, coated them with saliva and started massaging her clit. Bianca was still in her panties. Lying against the footboard, she was now rubbing her nipples. God, she was so beautiful. I started salivating looking at her pink nipples that were getting harder under her fingertips. Suddenly, she opened her eyes and looked straight at me. I blushed and averted my eyes. "Sorry!"
"It's ok, I don't mind."
"Are you sure your parents aren't coming home soon? I don't think they'd like to see a guy jerking off in their daughter's bed."
"Stop thinking outside of this room. Just be here!"
"I'm not really sure what to do. I don't know how to masturbate like a girl."
"You can try to copy me if you want. We all learned from each other."
I fumbled with the bra for a second before taking it off. I laid against the headboard and opened my legs.
"Wet your fingers and rub your nipples."
I brought one hand up to my mouth and sucked on my fingers a couple of times until they were wet. I brushed my nipple with my fingertips. I can't say I felt anything pleasurable, but I continued to watch Bianca and copy her. If nothing else, the image in front of me was making me hornier than anything I was doing. I wet my fingers again and started tracing circles around my areolas. I started feeling a little tingle in my chest. I caught my nipple between my thumb and my index finger and lightly pinched it. A small jolt of pleasure spread through my chest. Ok, this was feeling nice. And it was something new. I moved to the other breast and repeated everything. Yeah, this was definitely feeling nice. A drop of precum appeared on the tip of my penis. Bianca saw it as well and smiled at me.
"Looks like we're starting to get somewhere."
"This is pretty hot."
"You're hot, too," she said softly and smiled at me again. "Let's move on to our clits."
She raised her butt slightly off the mattress and shimmied out of her panties. I did the same. My eyes were glued to her pussy. I never thought I would see it, let alone be so close to it. She had a neatly trimmed bush above two fat outer lips. Like really fat lips. And at the top, peaking out from between those fat lips, a big clit was already pulsing. My mouth watered and my dick throbbed at the thought of sucking on that clit. After a few seconds I raised my head to meet her eyes.
"You like?" She had watched me watch her hungrily.
"It's beautiful."
"You don't think it's too big? I used to be so self-conscious about it. I guess I still am."
"It's really beautiful."
"Yours is beautiful, too. And even bigger than mine," she said with a naughty smile. "Wet your fingers again." She put her index and her middle finger in her mouth and sucked on them a few times, until they were slick with saliva. "And then rub your clit lightly."
I tried to copy her, but with just two fingers, it wasn't really working for me. I wet my thumb as well and caught the head of my penis between the three fingers and started rubbing them around it. It was nice, but nothing earth shattering. I tried to focus one finger on my frenulum, which I knew was more sensitive. It was better, but not by much. I looked at Bianca again, she had closed her eyes and was working her clit with one hand whilst pinching at a nipple with the other. Soft moans started coming from her mouth. I tried to refocus on my motion, but soon I found my hand wandering all along my shaft in order to keep momentum. I was back to jerking off like Alex. At least I had the best view in the world.
Moments later, Bianca opened her eyes again and saw my motions.
"Let's try something else," she said and stopped what she was doing. "Give me a pillow."
I handed her one from behind me. She kneeled on the bed and put the pillow between her legs. "Now you." I took another pillow and did the same.
"Sometimes I like to rub one off like this," she said and she started grinding her pussy against the pillow. "I like to bear down on the pillow. The pressure on my clit really gets me going."
I made a little canyon in the pillow to fit my dick and I started grinding against the pillow. Yeah, that was better, there was enough friction to get me going. Both her hands free, Bianca pinched both of her nipples. So did I. The jolt of pleasure in my chest was bigger this time. I was getting into it. After a few more thrusts, however, the pillow started to feel a little rough against my penis. I guess Bianca's pussy was giving her enough lubrication, but the few drops of precum that had leaked out of my penis were not enough to lubricate my whole shaft. A couple more thrusts and I started wincing.
"Not good?"
"It's kinda rough."
"Hmm...," she said, trying to think of a solution.
"Listen, I don't want to fuck up your mood. I'll just go back to jerking off. It's cool, I'll get more practice at home, find something that works."
"I have an idea," Bianca interrupted me. She turned towards a drawer and picked something from it. "Do you trust me?"
"Of course."
She had a tube of lube in one hand and a condom in the other. She opened the lube and squirted some on her hand. Without any warning, she took my penis in her hand and rubbed the lotion quickly onto it. Then she opened the condom wrapper and took it out. She grabbed my penis again and rolled the condom on my lubricated cock.
"Try fucking the pillow again. Now your clit should be lubricated enough."
Holy fucking mother of all that's holy. She moved so deftly that I didn't even have time to react. Did she just grab my dick? Twice? I was lucky that she moved so quickly, a couple more tugs and I would have cum all over her hands. I closed my eyes and took a deep breath, trying to calm myself, but my brain was in a haze. A couple more breaths and I managed to get some control back. I dropped my dick into the pillow and started grinding again. This was much, much better. I even let out a small moan.
"Yeah, that's it," Bianca said satisfied and resumed her own pleasuring.
We were both grinding on our pillows, face to face, and soon we even got into a common rhythm. Moans were getting louder, from both of us. After a while, I caught a glimpse of myself in the mirror. I pursed my lips keeping my eyes on myself. Fuck, I was pretty hot. I pinched a nipple with one hand and put the other hand in my hair. Yeah, baby, work it.
"This girl you have a crush on, is it you?" Bianca joked, seeing me put a show on for myself.
"No," I smiled back at her, "but she," and I nodded at my reflection in the mirror, "is starting to grow on me."
A few yelps came from Chris's corner of the room. I turned my head instinctively towards her, just enough to see her orgasm. She was turned to one side, clamping her hand between her legs. Her cheeks were red and her mouth was open. She was frozen still, but every couple of seconds a spasm jolted her whole body and she would let out a loud moan. This was the first real life woman orgasming that I ever saw and it was very hot.
I switched my attention back to Bianca. As hot as that was, she was way hotter.
"This girl you have a crush on," Bianca looked deep into my eyes, "is it someone in this room?"
Unable to escape her gaze, I bit my lip and I blushed. A large smile appeared on Bianca's face. Fuck, did I just give myself away? Or did she think I meant Chris?
This time, from the other side of the room, a couple of soft mewls could be heard. This must have been Andi. Half of me wanted to turn and see, but I managed to resist the temptation. The sounds she was making though, were very erotic. I hoped someday I would make a woman sound like that.
After a few more moments of grinding on the pillow, Bianca said: "Wanna try something else?"
"What?"
"The grinding, it's feminine enough, but I think I have a better idea."
She stopped, took the pillow out from between her legs and put it behind her back. "Give me another pillow." She laid back against the bedboard, put the second pillow under her lower back and spread her legs. I did the exact same thing, facing her. Since the bed wasn't long enough to fit both of us, our legs were sort of intertwined. My left leg between hers, her left leg between mine. As she spread her legs, she ended up resting one on top of mine. She took the bottle of lube and squirted some more onto her fingers. She threw the bottle to me and I did the same.
She moved her lubed hand between her legs, but not to her pussy. Lower. Of course, why didn't I think of this? What was a more feminine experience than being penetrated? Although I did feel a trepidation at the idea of invading myself in that manner for the first time (and with an audience!), the trepidation was mixed with a lot of excitement.
As Bianca's hand reached her ass, she didn't go directly inside with her finger. Instead she started massaging slowly around the hole. She was lubricating herself, but also teasing and caressing her little pucker. I moved my hand between my legs as well. Boy, was I happy I went through with the shaving. As I touched myself, my body gave a little shudder in response to the cold sensation of the lubricant and my hole spasmed in concert. But as I started gently rubbing in circular motions, some good sensations emerged. I guess I was discovering a bunch of new nerve endings in my body. As I experimented, I noticed that a lighter touch produced more of a sensation, and the more I rubbed, the closer to the hole I got.
All this time, my eyes were constantly glued to Bianca, not just because I wanted to see what she was doing, but I also because I wanted to admire her. After a few minutes of gentle rubs, she started poking at her opening with the tip of her finger. Short taps, like she was ringing a doorbell, all the while lubricating the outside of the rim. I copied her movements immediately. I wasn't sure where this journey would end, but I was very keen to get there.
Tap, tap, tap and then some more lube on the finger. This light stroking was sending vibrations all through my belly. Tap, tap, tap and then a longer push. My sphincter protested. Tap, tap, tap and another push and I was one knuckle in. My ass clenched around my finger and I stopped all movement. The feeling of this gentle breach was amazing. I grabbed a nipple with the other hand and squeezed it. My cock twitched in response. I waited for my sphincter to relax around my finger and when it finally did, I started a circular motion against the inside of the rim, trying to relax it further.
"Yeah, bitch, work that ass," I suddenly heard Chris exclaim. "Momma knows what she's talking about." We all snorted in amusement at her interjection which, in my case, produced another clenching around the finger, but this time more pleasant.
I turned my eyes towards Chris who had two fingers up her own ass and was rubbing furiously her clit, working on her second orgasm. I guess she wasn't lying earlier, no fingers were going up her pussy.
I turned my head towards Andi as well. I don't know, at this point, it felt ok. It was the first time I was seeing her naked since we were taking baths together as little kids and we were definitely not little kids anymore. I saw her svelte breasts slowly raising and lowering with her deep breaths. I saw the wisps of hair surrounding her thin pussy lips as two of her fingers were pushing in and out between them. She turned her head towards me as well and gave me a quick wink. I guess it was ok.
"More lube," Bianca whispered to me. "You can never have too much lube." Reluctantly, I removed my finger from myself and smeared them with another squirt from the bottle. I went right back to my back door. This time, I only rang the bell twice before going inside. I was already a familiar in that house. Still just one knuckle in, I restarted the circular motion that not only relaxed my anus, but also sent tiny waves of pleasure around my lower body. I caught myself moaning with each revolution.
It was time to be bolder. I gently pushed my finger a second knuckle in, surprised at how smooth it felt inside me. I let it rest for a few seconds to get accustomed to this new depth and then I started rotating my finger inside me again. Suddenly and unexpectedly, a high pitched yelp came out of my mouth. I don't know what that was, but it felt amazing. I went back with my finger and touched the same spot again. "Oh. Oh, yeah," I heard myself moan again.
"Think she found her g-spot," Chris announced to the room.
"My what? What is that?" I thought only women had g-spots.
"Your prostate," explained Bianca. "Most guys don't know this cause most guys would never put a finger up their ass, but the prostate is a major pleasure centre for men."
"How do you guys know all this?" I asked rubbing my finger against that spongy patch again, trying to confirm if that was true. "Ooooh," these moans kept jumping out of me, out of my control. "Yup. Yes, it is."
And like a kid with a shiny new toy, I started to play with it. At first I massaged it gently with the tip of my finger, sending small shivers through my pelvis with each stroke. I remembered reading that, in order to stimulate the g-spot in women, a "come hither" motion was recommended so I thought maybe this would work here as well. Oh, boy, did it work. With my finger curled, I started stroking my prostate. A pressure started growing in my belly with each stroke. I started writhing involuntarily and letting out audible moans. Suddenly, on one of these strokes, instead of an increasing pressure, I felt a release and a bunch of fluid shot out of my dick. It wasn't an orgasm, but it felt really good. Luckily, I was still wearing the condom, otherwise who knows where that would have landed. I decided to keep it on, just to be safe. (haha, get it? safe!) I didn't want to have to wash Bianca's bed sheets or, if this was just the beginning, possibly repaint the wall behind her bed.
It took me a few moments to process this new sensation that I had just experimented. I called it a pressure earlier, but it was pleasure. Pleasure from my finger working my ass. I had to keep going. I pulled my finger out to get more lube onto it and back in I went. This time I wanted to get a sense of this organ. Where did it start and where did it end? Which parts were the most pleasurable?
With the pad of my finger I found the margins of this pleasure hub. I started massaging around its edge. Slow circles all around it, clockwise at first, then counter-clock wise. I started spiraling slowly inwards, each go-round bringing me closer to the centre. And with each go-round the pleasure built and subsided, but never dropping to the level where it'd been before. I was moaning constantly and I did not care. My very hard dick was also begging for my attention. I started stroking it lightly with my other hand, trying to see if this would switch the focal point from my ass to my dick. It didn't, instead it added to it.
Small waves, originating from my loins, were spreading through my body, each a little more intense than the previous, each reaching a little bit further. I discovered that the prostate reacted to changes in pressure. As I reached the middle of my prostate, I pushed slightly on it with my finger. Another wave shot through me and a warmth started making its way from my pelvis towards my balls and my penis. I started stroking my penis harder.
"Oh, yeah. Oh, fuck. Mmm. " I'd never been this vocal during my self-pleasuring sessions. Quite the contrary, I always made sure that not a sound was heard. Right now, however, I had no inhibitions left. I moaned, I grunted, I turned from one side to the other, I pushed my hips up in the air and ground my ass against my finger. "Yeah. Yeah. Fuck that feels so good."
Remembering the doorbell technique from earlier, I started applying it to my p-spot. Instead of circling, I started gently pressing against the centre. I felt some more liquid dripping from my penis. I kept on ringing that bell, each time a little harder and a little longer, each time bigger waves of pleasure shooting through my body.
As the pleasure kept building, everything was becoming a blur. I looked at Bianca, two fingers in her pussy, one in her ass, caught in her own vortex of pleasure. She was moaning loudly each time she was pushing her fingers inside herself. As we were both writhing in bed, our bodies gravitated towards each other and we were much closer than where we started, our bums almost touching. As she shifted her body again, her leg ended on my shoulder. Without thinking, I turned my face towards it and kissed her ankle. A big, wet kiss. Apparently she liked it, because she pressed her sole on my face. I bit the arch of her foot lightly and elicited another moan from her. I stroked my dick faster and increased the pressure on my p-spot, while licking and kissing the bottom of Bianca's foot. She was working her pussy furiously now and, moment later, as she screamed in ecstasy, I felt her toes curling through my hair.
This was enough to send me over the edge. A hot wave of pleasure emerged from inside me, found my dick and shot through it. I grunted and I ejaculated violently in the condom, probably harder than I had ever done before. My sphincter contracted around my finger, sucking it deeper inside me, causing it to rub against my prostate again, causing me another moan. This happened several times, until my orgasm finally subsided.
This orgasm was like nothing I had experienced before. It was like I was enjoying another deeper, more intense orgasm on top of the usual kind of orgasm I was familiar with. I don't know how long it took me to finally ride the pleasure to a full stop, but when I finally did, my face was still buried in Bianca's sole and her toes were playing with my hair.
"Wow, you two are something else," finally Chris broke the silence. "I wish I'd filmed it, this is definitely going in my spank bank forever." We didn't respond. In fact, we didn't even break eye contact.
"You really got into it there at the end, no one's ever kissed me like that before," Bianca said to me.
"You liked it?"
"Yeah. Very hot. Don't tell anyone we did that."
"Of course not."
"I'm glad it happened, though."
***
It was heartbreaking taking off my wig and my makeup, putting my boy clothes back on. It was like putting on a prisoner's uniform. I realised halfway through that I didn't even take a picture and I almost broke into tears, but the girls assured me that this was only the first time of many and so my spirits went back up.
I must have hugged and kissed Andi a thousand times by the time we got home. I was floating on seven types of clouds. For the first time in my life, I felt one with myself. I didn't even think that such happiness could exist. We were holding hands and giggling as we went through the front door of our house and made towards upstairs.
"In the kitchen," were the words that stopped us in our tracks. Dick was summoning us.
"Where have you been all day?" This wasn't the first time Andi had been caught going out without permission, but I looked guilty as sin, and I knew I did, and I still couldn't compose myself.
"You two have been up to something lately. I knew if you thought you were alone all day, you'd be doing something that you shouldn't." Shit, this was a setup. He wasn't gone anywhere.
"Where have you been all day?" His voice went into a growl, which was worse than yelling.
"We went to see a movie, daddy, at the mall, and then we...," Andi started, but Dick was having none of it.
"You always have a lie ready, you deceiver, don't think that I don't know you. You go to your room and we'll see what the boy says."
"I'm not lying, daddy, really, we went..."
"Go to your room now," he growled again and a made like he was lunging at her, prompting her to run upstairs. Not knowing if he was really going for her, I tried to move between them, but he grabbed me.
"You're gonna protect your sister, boy? That's very noble. If only you weren't so weak," he barked at me, his face mere inches from mine. I pushed him away, but this only made him angrier.
"You wanna have a go at me, boy?" He grabbed my face and pushed me against the wall. "Come on, have a go." But I was too scared to do anything. "Yeah, I didn't think so."
He squinted his eyes and brought his face closer to mine.
"What's that smell on you, boy?"
"Wha... What?"
"What's that fruity smell on you. Are you turning into one of'em faggots, you unholy thing?"
"It's... just.. shampoo," I whimpered.
He pushed me harder against the wall and didn't say anything for a few moments.
"You better get your head on straight, boy, or I'll straighten it for you. You hear me?"
"Yes... yes, sir." Tears were running down my cheeks.
"You're so weak and pathetic. But I'm gonna change you, you hear me?"
"Yes, sir. Thank you, sir."
"Go to your room and don't come out until I tell you."
I ran up the stairs, into my room, collapsed in bed and started sobbing with my face buried in my pillow. Everything was ruined.
Some time later I heard two knocks on the wall. "Are you there?"
"Yes."
One single knock. "I love you."
"I love you, too."
Will continue in Part 3.
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