Time within the mansion continued to flow. Between my frequent bouts with Mom, my occasional BJs from Madison, and my flirting with Hannah, time passed quickly. Madison was in her first year of Academy, and thus was quite busy most of the time. Meanwhile, Hannah was getting ready for Academy, using all of Madison’s old material to study for the entrance exams. Both of my sisters were bright, so I had no worries that Hannah would succeed just as much as Madison.
As for myself? I had no reason to worry about the Academy. The entrance was automatically assured for men. We were all put into a single classroom. All four years of Academy actually put us in the same classroom. Every year, there were between 4-8 incoming male students, who were naturally very popular throughout the Academy which consisted of nearly 3000 women. With four years of Academy, that meant a total amount of 24 men to 3000 of the world’s brightest and most promising teen girls.
The education system in this world was vastly different than my own world. All education before sixteen was done privately. You either could afford to put your kids into a private school, or performed the teaching yourself at home. Of course, Hannah and Madison had been private-schooled for ten years, while I was exempt.
Academies then were a strange combination of a high school and a college. Rather than spending 4 years in high school and getting a degree, followed by 4 years in college for yet another degree, Academy lasted four years followed by a specialization. It was usually two years of generalized coursework, two years of specialized coursework, and then two years as an on-the-job intern. It didn’t matter what high education job you wanted, it was required that you work under educational requirements for two years to earn your degree. In some ways, I felt it made more sense than my old method, where people could graduate from various jobs with no practical experience.
Either way, men didn’t have requirements going into the school, and it seemed like we didn’t gain any requirements after being in school. Our only responsibility was to learn a base education, enough to be able to read, write, and handle money, and to deliver our sperm to women. In fact, the entire point of men being in the Academy was to get us close experience with the most suitable women. We were being conditioned to favor wealthy, educated women, and plopped in front of a buffet of girls right in their prime. It’s no surprise that most women become pregnant in the Academy. In fact, there are many women who only work so hard to get into the Academy just so they can become pregnant.
All of this was what I learned perusing through the library, asking Mom, a few maids, and even Madison, who begrudgingly answered a few of my questions stiffly. I was getting a better grip on this world, which seemed to be about the same as our modern world in technology. However, things were always different. The same technologies had different names. Some things were more advanced, while others were behind. For example, their healthcare system seemed to lag behind my worlds, yet their interspace, their version of the web, was actually much better, not that Mom allowed me to use it.
My mom was quite strict in her desire to keep me cut off from the world until Academy, and even though I managed to convince her to let me stick it in her butt, which felt tight and warm, but made me feel like I had to wash my dick ten times after I was done, I still haven’t managed to convince Mom to get me a VS, a holodisk player or a personal CD . Those would be this world’s magical equivalents to televisions, movie players, and computers. They called computers computational devices. I still only had just pieces of information I could glean from them.
As to why Mom was so paranoid, she was deathly afraid of me being taken advantage of. Considering dad had died because of a crazy fangirl, the feeling seemed legit. Those fangirls were called hares, by the way. They seemed to be the antithesis to the lipstick lesbian. Hares were man fanboys who obsessively chased after and wanted to fuck men. Their love of men grew to the obsession, and they were known for attacking women who they felt weren’t acceptable for their man of choice, which usually turned out to be all other women. This was apparently really bad in Academy, which kept most women from actively pursuing the men, thus reconfirming the custom of men having complete control of choice in this world.
For Mom’s part, she tried to educate me as much as possible. Sometimes, she felt like a crazy bible thumper as she spoke of all the horrific ways women could abuse me. As she described it, only Mom would truly love me and would always love me. I knew Mom spoke from her heart and it was truly unintentional, but had I not had the thirty-five-year-old reincarnated me to deduce reason, this kind of treatment could have been called brainwashing. Had I truly just been a naive thirteen-year-old boy, Mom’s brand of obsessiveness could have easily infected me to the point where I was a complete Momma’s boy.
Well, I suppose it was my thirty-five-year-old self who shamelessly started a relationship with his biological Mother that was partially to blame. She truly wouldn’t have lectured me so fervently had her love for me not long surpassed the realm of a normal, healthy relationship between a parent and a child. I wasn’t just her kid to protect, I was her man. Mom would truly do anything to protect me, even if it was a little smothering at times.
Naturally, her lessons also included sex. She worked to try to improve my sex drive, as well as my technique. I doubted if many other boys grew up being taught the techniques that pleased a woman the best. You usually just fall into a relationship with a woman who expects you to know what to do to please her, and her silence only leads to bad sex and disappointment. My mom, meanwhile, loved me so openly that she was very willing to explain just how she liked it.
I’d take some of her advice and use it on Madison or Hannah, leaving the girls red-faced and breathing hard. However, I had yet to go all the way with either one. Part of the reason was that Mom asked me to wait to pop their cherries until I was in Academy. She knew about my relationship with Madison, and she had an inkling that I was more than brotherly with Hannah as well. So, in the name of being open, she had simply asked me to wait until then to prevent any complications.
When I asked her what complications she was talking about, she only gave a hidden smile and shrugged. Personally, I think she just didn’t want to share me for as long as possible. If Mom wanted to monopolize my time for a few more years, I decided to let her have me. Mom was very generous and very loving, so naturally, I couldn’t complain about my sex life. My own feelings for Mom had definitely become love. Was it love for a parent, or love for a sexual partner? I didn’t really need to distinguish which, so I didn’t bother to.
Instead, I just enjoyed Mom however I could. As much as I spoke of Mom being experienced, that term was quite relative in this world. Mom had been in a relationship with dad, and had presumably had sex with him almost as much as she was having sex with me now. So naturally, she picked up a lot of things and had experience beyond the theoretical. However, I had been in a relationship for just as long myself.
In reality, while Mom tried to teach me sex, I was just as knowledgeable, if not more knowledgeable than she was. It amused me sometimes listening to her talk about sex, trying to explain things half-understood or flat out incorrect. Even porn in this world was underdeveloped, that book I made Hannah read being about as graphic as sex got. With so few men, there were few porns. Lots of romance books though, but they left things to a girl’s imagination, and once again, led to the seeming lack of practical experience.
For example, Mom was shocked when I finally suggested sticking it in her butt. She had never considered that hole. She originally told me ‘no’, not because she wasn’t curious, but because she didn’t think it’d work. She was convinced that no matter how hard I pushed, the butt only went one way and would somehow reject my penis. The look on her face when I popped it into her butt was so priceless that I wished I had a camera. However, it seemed to hurt Mom a lot and she didn’t appear to get much enjoyment out of it, so I ceased trying more anal for the meantime.
Furthermore, the three positions, missionary, doggie, and cowgirl… were the only positions Mom knew. I mean, she figured that you could fall into a different configuration of parts, but it never occurred to Mom to do something like that deliberately. One particular night I was feeling rambunctious, so I wanted to plow Mom wheel barrel style. I’m only thirteen so picking Mom up was out of the question, but sitting the edge of the bed, I managed to fuck Mom who had her legs on either side of my hips, her ass in my lap, and her face and arms on the floor at my feet.
After I showed her such a strange position, she became oddly fascinated with trying out as many other positions as she could. Soon, I had her in half a dozen different positions before she finally admitted that doggie still felt the best to her. Well, there was a reason missionary and doggie were the most popular. They’re the positions that have worked the best and have the most consistent satisfaction.
As to Veris, she didn’t come back in a month, nor two months. Nine months had passed and gone, and I could only wonder if I now had a kid out there somewhere. I had asked Mom about Veris once, and Mom only frowned and muttered something about Veris quitting on account of illness. Of course, I knew the truth. Veris had gotten what she wanted from me, and no longer needed to be here. Perhaps, originally, she never had any desire for my seed. However, something happened and she needed my seed badly. Her guilt over taking it led her to not wanting to show her face again. That was the end of that, I supposed.
While I didn’t feel guilty at the time, as I grew more connected to this world and my family, I started to. Maybe it was my mom’s constant brainwashing on the importance of seed, but I found myself unhappy thinking that I may have a kid out there I don’t know. That’s not the kind of person I want to be. In a moment of hormonal weakness, I realized I had made a mistake, and it was too late to take it back.
Hannah’s birthday came, which was two months before my own. I had been in this world for about eleven months now, at least from a reincarnated point of view, and had settled down pretty successfully. I had sex daily with Mom, sometimes with a BJ from my cute sister Madison. Speaking of which, the night before Hannah’s birthday, I got a visit from my eldest sister.
“Brother, do you want to do that now…” Madison asked directly.
The shyness she once had could no longer exist, given the number of times she’s sucked me off. If anything, it had basically grown into a routine. The entire process was natural to the point that if Madison didn’t come and suck me off, she’d start to get itchy. As I sat with my feet hanging over the foot of my bed, Madison got down on her knees. I leaned forward and grabbed her chin, giving her a quick peck on the lips. Madison accepted the kiss without complaint.
Over the course of nine months, I hadn’t just sat back and done nothing while receiving Madison’s attention. Of course, I always tried to push the envelope. My cute elder sister was a stubborn girl, but even she couldn’t help but grow in intimacy with me after so many intimate encounters. By three months in, I had gained full boob access, able to even put my hands up her shirt and squeeze her nipples without her own protest. Once in a while, such as when it was her time of the month, she would tell me they were sore and smack my hands away, but for the most part, I could feel them all I wanted to.
It took six months before she started letting me kiss her. First, it was just a cheek kiss, but after slowly moving my lips over until I reached the corner, soon I was able to peck her lips. A few times, we had even made out when Madison was feeling particularly horny. She usually forced me to stop and finish off with a blowjob before I could get her shirt up over her bra and her boobs exposed.
More recently, I had been working on her ass. She’d let me lean over and squeeze and rub it all I wanted now. I had worked my way into her pants, and could now feel her soft white butt in my hands. I had tried to work my hands down enough that I could reach up and attack her pussy, but I just wasn’t tall enough to do it from that position. I once tried to stick my finger in her butt, but she got angry at me and stormed out and I didn’t get any attention from her for two weeks.
If I wanted to rub her clit, I needed to attack from the front, but she was very apprehensive about my hand reaching between her legs. I could do light petting over the pants, but the second my hand tried to slip in the front, she’d grab it and pull it out. Thus, to this point, I’ve yet to touch Madison’s pussy in the slightest.
While I was considering these things, I realize that Madison hadn’t started working yet. She had her hand on my shaft, but she was staring off as if she was deep in thought.
“Hey, sister, what’s up?” I asked.
My words seemed to kick Madison out of it. She looked at me with a surprised expression, but as if to make up for her lack of movement, she started moving her hand rapidly up and down my cock. She was doing it perhaps a little too hard, and her small hand kept hitting my balls. It wasn’t enough to cause me that kind of pain, but it was uncomfortably close enough to it that I wanted her to stop.
“N-nothing,” Madison responded.
“Madison, I’m your brother.”
Madison tensed at those words. “I-I know…”
“Whatever it is, I’ll be there for you. I promise!” I made this declaration.
Madison’s look was expressionless, but after a moment she shook out of it and started sucking my cock. Meanwhile, I began to touch her B-size boobs. I had gone through a growth spurt in the last half-year. My height was now taller than Hannah and about the same height as Madison. Mom was only a few inches taller than me, and I would definitely outgrow her by next year, making me the tallest in the family. Regrettably, my sister didn’t have any such growth spurts, and her boobs were still tiny things, about half a handful.
That’s not to say I didn’t enjoy the feel of them in my hands. There was something I got from being able to hold those entire things in my palm that I didn’t get from Hannah and Mom, who’s boobs exceeded my hand size and could only be held up or squeezed, not engulfed in entirety. However, it was all part of Madison’s charm, who looked willowier and more delicate than the rest of my curvaceous family. Of course, that was likely because she was only a half-sibling, after all.
Soon, I was working my hands down Madison’s stomach again, abandoning her breasts to touch the area I’d been wanting to manipulate for months now. As my hand began to push under the elastic of her skirt, I was elated to find that she didn’t prevent me. In fact, even though Madison was still sucking my cock, she seemed to be doing it subconsciously. I could tell she was distracted by whatever was going on again. Thus, I took advantage of her distraction, and soon my hands found their way into her panties.
As my hand brushed across the light stubble of her pubic hair, I nearly creamed in her mouth right there. However, once I came, my expedition would be over, so I fought to keep control. It wasn’t difficult since Madison was distracted and not focused on making me cum. For the first time, I got to bring my fingers through my sister’s pubic hair. She wasn’t as thick and bushy as Mom. Of course, Mom shaved it into a perfect landing strip, so Mom wasn’t hairy, but her pubic hair was thick, curly, dark and full.
In comparison, Madison’s was thin, straggly, and hard to see. Madison hadn’t shaved it into any kind of pattern, but there wasn’t enough of it to make her look hairy either. It was actually the pubic hair of a currently developing young girl. Even Hannah probably had pubic hair grown up much like Mom’s. At least, the times I had managed to rub her through her panties I had felt some thick hair up there, but it looked like lagging behind in development didn’t just affect Madison’s breasts. For a woman who had been blowing my cock for almost a year, she was very underdeveloped. Her pussy was fresh and untampered.
It was those kinds of thoughts that edged me along, and as my finger lowered the last couple of inches, I finally came across a thinner, ruffled texture which felt a little wet against my skin. That would be Madison’s clit, which was now literally at my fingertips. With that, I couldn’t hold back any longer. My fingers started to attack her clit. I tried to emulate the motions I had seen Veris use on her daughter. If it drove Nada, the expressionless daughter, crazy, then it was bound to work on my cute sister, who already grew quite breathless just by playing with her butt and boobs.
“Nnnn!” Madison finally realized where my fingers ended up and her eyes widened.
She reached down immediately, grabbing my wrist. Just when I was afraid she’d yank my hands from her pants, she then froze like that. Her face looked slightly strained as she looked at me, her mouth slightly open and breathing roughly, but she continued to let me rub her clit as her cheeks grew more and more pink. She still had one hand on my hard cock, while the other held my wrist as it made little swirls around her cunt. She wasn’t sucking my cock, rather she was looking at me with her brow furrowed like she was still considering something. Since her lips were free, I leaned forward and pushed them.
“Mmm…N…” Madison could only let out a moan as my tongue pushed its way into hers.
Being more familiar with making out, Madison was quick to accept my tongue and dart hers out. We continued to swap saliva, our tongues dancing in each other’s mouths while my hand blazed over Madison’s cunni and Madison’s hand gripped my shaft.
“Mmmm… mmmm… MMMM…” Madison’s body started to shiver, and her hips suddenly started rocking.
I didn’t understand what was happening as I continued to kiss her while her eyes closed tightly and her body convulsed. It wasn’t until I felt a sudden gush of liquid on my fingertips that I realized Madison was unconsciously humping the air, cumming as a result of my fingers. I broke my lips away from Madison, and the concentration and tenseness in her eyes were gone. Instead, she had an odd dreamy look, her mouth slightly open, a little bit of spit strung between our lips.
“I love you, Madison.” The words came out.
I really did love my sister. Unlike Mom, I was very clear what kind of love this was. I was in love with my elder sister. She was so beautiful and cute. She sucked my cock every day and swallowed. She was tenacious, pouty, generous, giving, but selfish in all the best ways. I wanted to hold her and love her. This was a girl I wanted to date in high school. Hell, this was a girl I wanted to date as an adult. A part of me knew these were just teenage feelings. One advantage, though was that Madison was a teenager too, and thus was just as prone to be caught up in her hormones as I was.
Madison didn’t respond when I told her I loved her. However, she did start pulling off my shirt. I pulled off hers as well. Soon, underwear went as well and there stood a brother and sister completely naked. We ended up on my bed, holding each other and kissing. As I pressed my naked body against Madison’s, I realized how much of a different experience this was than when with Mom. Mom was voluptuous and curvy, with big boobs and a nice round butt.
Madison was much lankier and thinner. My arms could wrap around her entire body. In my grasp, she felt so thin and fragile. I felt so big beside her. Mom could sometimes overwhelm me, her big boobs sometimes made the power dynamic between us lean on her side since I was shorter and overall smaller. However, Madison was my height, and much skinnier, and whether it was her boobs or her butt, it was all perfectly hand-sized, as if Madison was crafted just for me.
“A-are you sure about this?” I asked, finally moving so that I was on top of Madison.
I already had her legs spread. My dick was hard, Madison’s pussy was wet, and I was one thrust away from taking my sister’s virginity forever. My heart was beating wildly, and I probably looked just as flushed as Madison. I was so excited and so happy to be feeling this small girl under me. I truly felt powerful, like a real man, for the first time since I’d been to this world.
Madison looked up at me tearfully, but she nodded. “I-if it’s Brother… then I don’t mind having your baby.”
“Ah…” I gave a noise, but then quickly shook my head and smiled at Madison’s words.
I forgot once again how different this world was from my own. This was a world obsessed with pregnancy. Even my cute and beautiful sister wasn’t spared from seeing all sex as a means of becoming pregnant. Well, I wanted to take my sister’s virginity now, but I had no desire to make a baby. I would pull out and blow it on her stomach if it comes to that point. However, before I spend too long thinking about ejaculating, let’s get it in first.
Knock. Knock Knock!
The sound of someone at my door was like an explosion. Madison shoved me away so fast I nearly fell off the bed. Madison herself was beyond panicked, pure fear on her face as she desperately looked for her clothing. I also ran around looking to grab my own.
Knock. Knock. Knock.
“Clyburn, it’s Mommy, let me in.”
Although Mom knew I had some relations with Madison, she probably didn’t know we were two seconds away from going all the way. Well, I didn’t know we were two seconds from going all the way until right before it happened. Now that moment was passed and I didn’t know how long it’d take before I got another chance.
The panicked Madison fled through the side door and no sooner did the door close then I ran up to and unlocked my room.
“Took you enough time!” Mom sniffed, pushing her way into the room.
“M-Mom! What is it?” I asked.
I wasn’t really too worried, as Mom did know about Madison. However, Madison didn’t know Mom knew, so I still had to be careful. Madison could still be in the other room just like Mom was that one time, so at the least, I needed to make sure Mom didn’t say anything that could incriminate us. Mom merely walked into the room and with a single glance, turned to me with her lips slightly upturned.
“Hello, my dear, I just needed to talk to you about some things,” Mom said cautiously.
I nodded, heading over to the bed and sitting down. Mom walked over and sat next to me, thankfully not getting too close as to be revealing.
“What things?” I tried to sound casual, even though I glanced at the door where Madison had left a few seconds ago.
“Tomorrow is Hannah’s birthday. Normally, that wouldn’t be a big deal, but… we’ll be having a guest come by tomorrow. It’s an old classmate from the Academy. Her name is Rose. She wants to have some kind of birthday celebration. She says they’re big overseas.”
“She? A guest?” I asked, only then realizing that given the rate of men to women, it’d be much weirder if the guest wasn’t a woman.
“She would be… how do I put it?” Mom tapped her finger on her lips. “She’s my sister and your aunt.”
My eyes widened in surprise. “Grandma had two children?”
Mom nodded. “With two different men, so we’re half-siblings, but she’s still your aunt and we grew up together, so I feel I have some responsibilities to her. We’d been together since private school, but I ended up marrying your dad and afterward, we sort of drifted apart. She suddenly contacted me recently.”
“Well, that’s fine, I guess… is that what you wanted to tell me?”
Mom smiled. “She is… a woman, so I must warn you…”
I immediately nodded. “Yes, yes… don’t trust her. Don’t be in a situation alone with her. Treat all women like they’re after my seed.”
I repeated the doctrine my mother had spent the last year drilling into me. It appeared like Mom didn’t even trust her half-sister, a woman who she grew up with and considered a friend. Truly, I was the most important person to Mom.
“Good boy.” Mom patted my head.
“I-is that all?” I added, a little afraid she might toss herself at me right away.
“No, but you’ve been naughty so the secret I was going to tell you is just going to have to be a surprise,” Mom said mischievously, suddenly standing up and putting something in my hand while leaning into my ear and whispering, “Come to my room tonight, you have some explaining to do.”
Mom turned around and walked away, not saying anything else until the door closed. Only then did I open my hand and pull the cloth she had handed me out. It took me a moment to realize what it was. They were Madison’s panties. She must have left them on the bed when she had rushed to get dress and flee. Mom had seen them. I gulped, feeling a little guilty that I almost broke the promise I made with Mom. I’ll need to head over to her room and plead forgiveness. I also planned to relieve some of my own stress, naturally, built up from Madison’s unfinished job.
On that note, when I checked on the room, I saw that Madison had indeed fled back to her room pantyless while Mom was in here. Madison’s panties were small since Madison herself had small hips and a flat butt. They were a frilly white thing, nice enough that I suspected she selected them knowing I’d see them. There was a clear soiled stain in the front, where I had made Madison cum. It was the first time I had touched her pussy, and I had made her soil her panties. I had almost taken her virginity as well.
Thus, I took those panties and kept them. They were right next to the panties of the girl who had taken my virginity in this world. It wasn’t my intention to be a pervert, but somehow, I was starting to gain a collection of soiled panties. I wondered a bit if I should claim a pair from Mom as well. Shutting the drawer and considering getting a lock for my collection, I headed off to Mom’s room to apologize and then have my way with her. Life was good.