This is a work of fiction. All the characters in this are 18 by the time anything sexual happens to them. For the record there's a lot of build up before the actual feminization starts, this story is just as much about Lynne's sexual journey as it is about Alex's. Enjoy.
Growing up in an all girl household, my brother was never the picture of masculinity. He was on the smaller side for a boy and he had long hair that made him look almost like a girl. When we were younger people used to confuse him for a girl pretty regularly, him having a gender neutral name didn't help either. I was only 2 years older than him but I was always looking after Alex more than our mother or older sister.
Speaking of our mother she wasn't the best, she was never married and out of her three children none of us had the same father. And it showed too. Our older sister, Ellie, had curly blonde hair and blue eyes. I took more after Mom and had the same straight black hair and dark brown eyes as her. Alex was the furthest from each of us with his wavy orange hair and green eyes.
Whenever the three of us were in public no one believed we were really siblings. Since Ellie was 6 years older than me people always assumed she was our babysitter. If she was I'm sure she would have been fired though cause she could never be bothered to actually look out for us. I was usually the responsible one. Being the oldest, Ellie got her own room while Alex and I had to share.
Our mom had a lot of boyfriends. Most men didn't stick around long enough for us to learn their names let alone become a positive male role model for Alex. He was pretty much raised by girls, and girls don't really have any business raising boys so Alex was always a bit feminine.
When Alex was 14 and I was 16 our sister moved out. To live with her boyfriend at the time. She had a huge fight with our mom about it. Mom didn't want her to leave but Ellie was 22 and tired of our mother's rules. To my knowledge that was was the last time either of them ever spoke to each other.
Ellie moved out and I got her old room. She didn't take most of her stuff so I got to inherit a lot of her clothing and other stuff. Most of my clothes were her hand me downs anyway but now I had access to some of her clothes she had bought for herself. Alex and I weren't as close as we had been when we shared a room but we were still best friends.
With my newfound wardrobe my style took a bit of a change. I adapted this pseudo goth style that involved wearing mostly black clothes and using dark eyeliner and lipstick. Ellie was never the kind of girl who dressed like this so I was very curious as to why she had all this goth fashion. My new style did wonders for my confidence.
When I was 18 and about to graduate high school I met a nice guy named Nick, who eventually became my boyfriend. Nick was a year older than me and was an elections apprentice. He wasn't a super masculine, macho meathead like the guys my sister dated or the creepy older guys my mom brought around. He was sweet and funny, he had sandy brown hair and light brown eyes. He was about 5'10 and was lean with the hint of muscles.
The best thing about him was that he got along great with Alex. My mom didn't hate him so he was welcome around the house as long as he didn't spend the night. We still spent a lot of time together, Nick would hang out with Alex and I. We'd often curl up on the couch and watch movies together. Alex and I both wanted to watch chick flicks like twilight and other things that guys should hate. Nick would insist on watching action movies, I agreed to a few because I figured Alex would like them but he always preferred romantic movies over action.
Nick and I dated for a few years and he'd been the one to take my virginity. It was his first time too and we had rushed missionary sex in the back of his father's Jeep. It was fun but I knew it could be better. If Mom and Ellie were so crazy about sex then there had to be more to it than that. So we had a lot more sex. In as many positions as we could think of in as many places as I thought we could get away with.
By the time I was 20 I was definitely enjoying sex more but I still was under the impression that it could be better. I felt it was time to have an awkward conversation with my sister and ask her advice. She had broken up with the original guy she had lived with when she moved out and was living with a different one. I hadn't seen her in a while but we still talked on the phone. I asked her if it was okay if I came over for a visit. She said yes and that I should bring Alex.
It was an overcast cloudy day when Alex and I went to see Ellie, he was wearing a light blue hoodie that used to be mine and a faded pair of jeans that I think might have also been mine at some point because of how tight they were on him. I was wearing yoga pants and a long sleeve t-shirt. As we approached the house Alex asked me, "Why are we doing this, Lynne?"
"Because she's our sister and we miss her. Come on I bet you can't even tell me the last time we all saw each other." I smiled back at him. Of course I didn't tell him the real reason was because I wanted sex advise. Alex was 18 now but he was still really innocent, he'd never had a girlfriend or even talked about anything like that with me.
"I don't know, maybe if she didn't date assholes we'd see her more." Alex said while staring at the ground.
"Don't be like that Alex, we're going to go in there and have a nice visit with our long lost sister." I said with a hint of a joke. Alex smiled and we went up to ring the doorbell. After a minute the door was opened by a strikingly handsome man in his early 30s. He had a shaved head and a beard. He was also considerably taller than both of us. I was 5'5 and Alex was 5'7 so neither of us were giants but this guy must have been at least 6'2 and very muscular. He smiled when he saw us.
"You must be Lynne and Alex. Ellie told me you'd be coming over. Come on in, I'm Tom." He opened the door wide so we could get past him. His house was a bit of a mess with cardboard boxes and dirty clothes on the ground everywhere and there was a funky smell. We went into the living room area where Ellie was waiting for us on the couch. In her traditional fashion she was wearing a lot of makeup and wore a tank top shirt that didn't cover most of her D cup breasts. She got up and we both noticed that her stomach had what looked like a baby bump.
"Lynne! Alex! It's so good to see you both!" She got up and wrapped her arms around us in a nice big hug. "Ahh how have you both been? I haven't seen you in so long." She squealed.
"We're good." I said as we separated. She kept a hand on either of our shoulders. "Ellie is it just me or are you pregnant?" I looked at her with a concerned smile.
"Oh jeez, is it that obvious?" She smiled and rubbed her stomach.
"Yes. Yes it is." Alex said dryly. I gave him a look that told him to shut up.
"You look lovely, sis. How far along are you?" I said quickly trying to pull focus away from Alex's comment.
"About 4 months. But that's not the only big news." She said excitedly, she held out her hand palm down showing us a gold ring with a small clear gem on it. "We're getting married!"
"Congratulations! I'm so happy for you." I pulled her in for another hug. This was kinda shocking but I know she needed at least one family member to be excited with her. I could tell that Alex was already judging her and I knew Mom would freak out.
We sat on the couch together. Tom and Ellie sat together with his arm around her, I sat on the other side of the couch and Alex found a chair after moving a pile of dirty laundry. We chatted for a while about nothing in particular, I wanted to get Ellie alone so I could ask her about the real reason I came here. After a few minutes of chit chat she got up to fetch drinks from the kitchen for everyone. I saw this as my moment to strike and followed her.
Her big sister instincts must have sensed that I needed to talk to her because once we got out of earshot of the boys she turned serious for a change and asked me straight up, "What's going on, Lynne? You look like you have something on your mind."
I wasn't expecting it to be that simple. "Yeah, it's kinda embarrassing." I nervously admitted.
"Let me guess, is it about boys?" She said as she leaned against the kitchen counter. The sink was full of dirty dishes.
"Sorta," I averted my gaze from her. "I've been seeing this guy for a while now and I really like him but the sex isn't great. I don't really know what we're doing wrong. I always thought it was supposed to be like, more fun than it is." She was silent for a moment.
"Oh honey. Some guys are just bad at sex, does he have a little dick? Or does he not last long enough?" Ellie asked with concern in her voice.
"No, his size is alright, I think. I haven't actually seen that many but it looks big. How long is sex supposed to last?" I blushed as I spoke.
"Lynne sex is supposed to last as long as it still feels good. What positions have you tried?" Said Ellie.
I explained to her that we'd tried a bunch of positions, missionary, doggy style, cowgirl. None of them did anything special for me. She thought about it for a moment.
"Okay this is going to sound backwards but I'll tell you what works for me. I get off on serving men. The more into it he is the more I get off. Maybe you should talk to your boyfriend and ask him what his biggest fantasy is and then do exactly that for him." Ellie explained.
I looked at her for a second and we both laughed. "You're right, that does sound backwards." I said through a laugh.
"I'm serious though, Tom gets animalistic in the bedroom. He fucks me hard and always cums inside. He's got a breeding fetish and I did exactly what he wanted by getting pregnant. He's happy, I'm happy. Give it a shot, if he's happy you'll be happy." She stopped laughing and gave me another hug. "Or maybe you're just a lesbian." She said and we laughed again.
I lightly pushed her away and told her to shut up but we were both smiling at each other. Ellie got drinks for us and we went back to the guys in the living room. Tom had turned the TV on and was watching football and was zoned in on it like a hawk. Alex on the other hand was paying attention to Tom. If I didn't know better I'd say it looked like he had a school girl crush on Tom. He could have just been zoned out, his eyes were droopy and he looked relaxed.
Ellie passed a can of beer to Tom and a soda to Alex. We sat for a little while longer, Tom continued watching his football game, Alex watched him and I chatted with Ellie about her wedding plans. Eventually we finished our visit and left. Ellie made us promise not to tell Mom about her pregnancy or engagement and that we'd stop by again soon.
As we walked home I asked Alex. "What were you staring at Tom for? You couldn't take your eyes off him."
He blushed a bright red and looked away. "I don't know what you're talking about. I was watching the game with him." He spoke quickly and I'd known him long enough to know he was lying.
"You know it's fine if you were. He's a handsome man." I was only half joking with him but the way he squirmed I could tell I'd made him uncomfortable.
"What were you and Ellie talking about in the kitchen? You were gone for a long time." The little bastard flipped the spotlight onto me and it was my turn to blush and look away.
"Just about her wedding and stuff." I lied. The thing about siblings is we can usually tell when the other is lying. And I'm certain that he saw through me.
"I heard what she said about Tom. How he wanted to breed her. I couldn't believe it, he looks like such a normal guy." Alex said in a pouty way.
"There's nothing wrong with being kinky, Alex. We're all entitled to our weird fetishes. Please don't judge them." I stopped walking and turned him to face me.
He looked down away from me. "I wasn't judging them, I'm actually kinda jealous." His words were hardly more than a whisper.
His words completely took me by surprise. "Oh. Well, uh. Yeah." Was all that I could say. I let go of him and continued walking. He walked a little behind me so we didn't have to look at each other for the rest of the way home.
A few days later Nick had the weekend off so he was around hanging out with us. Our mom went to stay in a hotel with some guy she'd just met so we had the house to just the three of us. I was planning on breaking her rule about having my boyfriend stay overnight. It wasn't our first time but it did feel exciting breaking rules. We spent Saturday evening watching TV with Alex. Him on one side of the couch with Nick and I on the other.
We were under a blanket and Alex was paying close attention to the tv when I got a wicked idea. Under the blanket I slid my hand down to Nick's crotch and rubbed his penis lightly through his athletic shorts. I didn't look at him when I did it so I couldn't see his reaction but I sure felt his dick harden. I took it as his permission to keep going. I rubbed a little faster and a little harder. He was definitely enjoying it when a not so quit grunt escaped him. I immediately stopped rubbing him as Alex looked over.
"Are you okay, Nick?" He asked.
"Yeah buddy, I'm fine. I just got a Charlie horse. I think it's time we went to bed, don't you, Lynne?" He nonchalantly stood up with his throbbing erection facing away from Alex.I knew what he was doing, he was ready for sex. I knew it was because of what I'd done so I played along.
"Yeah, it is getting late. Goodnight Alex." I stood up behind Nick and we both went in the direction of my bedroom as casually as two sexually charged young adults could.
We heard Alex comment, "But it's only 9:30?" Over our shoulders as we left. When we got back to my room his hands were all over me in a flash. He pulled me close and kissed me with burning passion. I felt his still rock hard cock pushing against me through his shorts.
"Wow Lynne, what's gotten into you? Lately getting sex from you has been like pulling teeth." Nick said while coming up for air between our kisses.
"What? Am I not allowed to be horny too?" I asked him while pulling his shirt up.
"No, this is great. I love the horny side of you." He backed away far enough to get his shirt off.
Before he could embrace me again I stopped him and looked him in the eyes and asked him. "Do you have a fantasy? Or something you'd like to do differently when we have sex?" I couldn't help but blush. I'd planned to be less blunt when I asked him this but I just blurted it out like an idiot.
He certainly wasn't expecting any of what I'd said. "Uh, yeah. Actually I was thinking I'd like to be a little more dominant and rough with you. I didn't know how to ask." He moved forward and held me. "Is that something you'd consider letting me do?"
I thought about it for a second and Ellie's words played back in my head. 'If he's happy you'll be happy.' I figured that it was worth a shot.
I nodded to him. "Yeah, I think that I'd be okay with that." I said sheepishly. My consent was all he needed as he pulled me over to the bed and threw me down on it. I hadn't expected him to be so quick to get into it. Before I could recover I felt him yank my shirt up over my boobs and pull my sweatpants and panties down to my knees. I wasn't wearing a bra, my B cup breasts didn't really need one when I was home. His left hand clamped down on my boob and his left hand engulfed my pussy. He put his face in mine and we kissed.
His hands started to work magic on my sensitive bits. He rubbed one hand over the outside of my vagina and with the other he pinched my nipple. I was definitely turned on at this point. His fingers on my pussy sunk deeper with every pass and I could feel myself getting wet. His tongue invaded my mouth as his stiff cock pressed against my hip.
He did let go eventually, he stood up and pulled his shorts and boxers off. His cock spring to life and stared me down, roughly 7 inches of manhood. Nick got up on the bed and held his penis against my face. I'd sucked it before but only as foreplay, he'd never cum in my mouth or anything like that. He rubbed his cock up and down my face. When I opened my mouth and tried to suck his cock he lifted it up and slipped me with it. I was more surprised than anything.
"You've been a naughty girl. I have to punish you for making me hard on the couch with Alex sitting right there. Turn over onto your stomach." Nick was getting really into this but I wasn't quite sold. My hesitation caused him to slap my face with his dick again. "Now, Slut!" He commanded me. I did what he said and flipped over, which wasn't easy with my pants and underwear around my knees.
Once I was face down Nick moved down to my butt. Straddled me with his knees on either side of my hips with his dick firmly resting between my butt cheeks. He took a strong grip on either side of my cheeks and wedged his penis against my butt. "Now beg for my cock you slut!" He demanded with a firm slap on the ass.
I winced and did what he said. "Please fuck me!" I begged him. I wasn't anywhere near as into this as he was and I think he realized it because toned down the dom thing after that. He pulled his cock from between my butt and slid it into my pussy. I was wet enough for him to glide in, I liked him being rough with me but it was the dirty talk that didn't appeal to me. Once his cock was in me though everything was forgiven. He rocked back and forth, plunging his penis into me. It felt good but not in any way that was more special than every time we'd had sex before.
I turned my head as best I could to see how much Nick was enjoying it. I got about halfway to an angle where I could see him when he put his hand on the back of my head and pushed me down on the bed. I don't think he would have done that if he wasn't getting into it so I had my answer anyway. He was grunting more than usual too. Ellie was right that I would get a sense of satisfaction from knowing how much he was enjoying it but it wasn't the feeling I was looking for.
Nick's pace sped up and I could tell by his grunts that he was close to cumming. "Lynne I've always wanted to cum on your face like you were a pornstar. Please, babe? I'm so close." I was yet again surprised, he always came inside me but I wanted him to be happy so I nodded. "Come and get it, baby." He pulled his penis out of me and got off of me enough that I could slide out from under him.
I rolled over so my face was under his cock. He wasted no time jerking himself to the point of eruption. His first spurt launched cum on to my face and neck, his second missile coated my tits and he brought the third one to my lips and directly shot his cum into my mouth. I instantly swallowed his cumshot and took the head of his cock in my mouth and brought my hand up and milked all his remaining cum onto my tongue and down my throat.
His excitement done with, he slumped back. Nick was the type of guy who could only cum once a session and after that one orgasm he was usually very tired. He hadn't given me an orgasm, I wasn't sure if ever even had an orgasm. That was one of the things that frustrated me the most. He was laying down on my bed, still naked. He would be asleep in minutes if he wasn't already.
I wanted to clean myself up. I was sticky from the cum. Part of me wished he'd just cum inside me like usual but he seemed so excited I couldn't refuse him. I pulled my panties and sweatpants up and pulled my shirt all the way off, careful not to get any cum on it.
Then I noticed something strange, the door to my bedroom was cracked open. It could have been an accident when we came in here, horny and all over each other but I could have sworn I closed it. I went over and pulled it open. I poked my head out just in time to see Alex slinking away down the hall.