Sissyficatio- 30 Books Mega Bundle Page 2

  It didn’t last long. The moment I saw her again, I was a mess.

  CHAPTER III

  That weekend, our parents went away together for their honeymoon. They didn’t go far, just a few hours away to a ski resort for the long weekend, but it left the house to me and Kelsey.

  And I was starting to get the thought that Kelsey wanted me to make a move on her, like she was trying to seduce me. Every time we crossed paths, she would let that sly little smirk slip (that smirk alone was enough to make my legs weak, and I think she knew it). She would take showers with the door open slightly—just across the hall from my bedroom. Surely she knew I could see inside, and with the help of the bathroom mirror, I could see a sliver of her naked body through the slit in the curtain. She wasn’t afraid to walk around the house wearing nothing but a tiny towel which hardly covered her nipples, and only extended a few inches below her crotch.

  All I needed to do was pretend like I dropped a pencil and I would have gotten the answer I was looking for, whether she had a cunt or a cock.

  “What are you watching?” she asked, while I was sitting on the couch, watching a movie.

  “I don’t know. Some old action flick,” I said, and she took a seat right next to me, leaning into me. Her body was warm.

  “Mind if I watch?” she asked.

  My heart was aflutter. We were cuddling, but was I cuddling with a man or a woman. She was soft, fresh out of the shower, smelling amazing as always. She had an old t-shirt on and a tiny pair of cotton pyjama shorts.

  Did it even matter if she was a man or a woman? She was sexy regardless. She felt, looked, smelled, and acted like a woman, so what difference did it really make? It’s not like if I was attracted to her, that somehow made me gay, right?

  After about an hour, I could see through the television reflection that she had fallen asleep, her face nestled against my side. My arm had found its way around her body and my hand had found its way onto her stomach, just inches from her crotch. It was my chance to solve the mystery, to see what was really there. My heart rate sped up drastically, pounding against my ribcage. If that didn’t wake her up, then nothing would.

  Carefully, I let my hand creep down. After a deep breath, I subtly slipped it over her crotch. My plan, if she woke up, was to pretend as though I was asleep, that my hand just slipped there by accident.

  There was a slight bulge between her legs, though it was hard to tell what it was. It was soft. It could have been a plump pussy, or it could have been a flaccid cock tucked between her legs. I was still nowhere closer to knowing for sure.

  But my little move didn’t seem to wake her up. How far could I go without waking her up? I took another deep breath. If putting my hand over her crotch didn’t wake her up, why would it wake her up if I was under her shorts?

  I carefully pushed my fingers under the waistband of her cotton shorts. I was so nervous, I could hardly breathe. If she woke up now, it wouldn’t be so easy to explain. ‘Oh, I fell asleep and my hand slipped under your shorts. Woops!’ No one would have believed that. She wasn’t wearing panties. Her pubic hair was soft and neatly trimmed. I pushed my hand down further.

  And then my hand was on it: her flaccid cock. She had a cock. That was no pussy. I could feel everything—her long shaft, her bulbous tip, her warm ball sack. My dad wasn’t screwing with me after all, she really was born a man. She really was undergoing a sex change.

  She moved. My heart sprung into a panic, but instead of pulling my hand out from her bottoms, I froze. She wasn’t awake, she was just repositioning herself. Still asleep, she reached down and put her hand over mine, pushing it down against her cock. Shit—now I couldn’t move. I couldn’t pull my hand out without waking her up. She had me trapped, my hand sandwiched between her hand and her cock. She started to rub my hand, forcing me to rub her long shaft. She let out a cute little sigh. I made sure she was in fact sleeping and her eyes were in fact closed—they were, and she was.

  I needed to think. If I pulled my hand out too quickly, she would have been jolted awake. Though I wasn’t sure I would be able to pull it out slowly either, not without her noticing. My other option was to wait until she repositioned again and moved her hand so I could escape discreetly. That option didn’t look too likely either, seeing as she really had a good handle on my hand between her legs, forcing me to massage her dick—and she was getting hard, fast.

  Holy shit, she was getting hard. I had my hand on my sleeping step-sister’s cock, and it was getting hard. The thought alone was absurd. The fact it was really happening—I thought for a minute I was dreaming, that I would wake up any second. But I wasn’t dreaming. I was really massaging her cock. I needed to think of an out. I needed to just find the right timing to pull out quickly, so quick that when she wakes up, she doesn’t realize I was ever down there at all.

  She reached over and slipped her free hand over my cock. She started to rub and fondle my dick. I became frozen. Was she still asleep, or was she just pretending? Was it possible she was dreaming of giving me a handjob? Like a dog dreaming of chasing a rabbit, kicking its legs in the air as it bounds through a field—except unlike the rabbit, my cock was really there. I looked down again. Her eyes were still closed, but that didn’t necessarily mean anything.

  She was rock-hard now, and somehow my fingers were wrapped around her impressive girth. She finally released my hand, using her newly freed hand to reach up and squeeze her tit. It was my chance to pull out of my conundrum, but I didn’t. I kept my grip on her cock. I allowed her to continue massaging my dick. It felt too good to put an end to. Besides, it was quite the sight—the most beautiful woman I’d ever seen snuggled up against me, massaging my dick as she squeezed her perfect tits. Except she wasn’t actually a woman. She was a man. I was getting my cock rubbed by a man. I had a firm grip around a man’s throbbing erection.

  She slipped her hand into my pants and took hold of my cock for real, skin-on-skin. She started to stroke me, her eyes still closed, maybe asleep, maybe not. I played along, carefully beginning to stroke her length.

  I couldn’t believe how big her cock had grown. How was she able to hide such an impressive beast between her legs? Especially in that skin-tight dress, and those little short-shorts she wore. Wasn’t she worried she would get aroused accidentally? In that red dress she wore at the wedding—her erect cock would have ripped right through the thing for crying out loud!

  She moved again, making my heart skip a beat. This time, she reached down and shimmied her shorts down to her thighs before reaching back up, slipping her hand under her shirt so she could fondle her nipples. If she was sleeping, I wondered, who was she fucking in her dream? Was it me she was giving a handjob to? Was it me jerking her off?

  Her cock was out in the open now—in plain sight. There was no possible way of denying it—she was born a man, and a well-endowed man at that. That cock was definitely no prosthetic, no fake. I couldn’t believe I actually had my hand around it. I couldn’t believe I was actually jerking it off. What if I actually got her to come? Would that wake her up? Would she realize she was getting a handjob from her brother-in-law and then freak out?

  She had me rock-hard in my pants and she was working my shaft like a seasoned pro, sliding her fingers up and down my length with just the perfect pressure in all the perfect spots. There was no doubt she had experience with this kind of thing—I suppose it helped that she had a cock of her own to practise on.

  “I’m going to come, baby,” she said, her eyes still closed. My heart skipped a beat again. “Oh fuck, I’m going to come.” She bit her lip and let out a long, soft sigh. God, it was cute. She was beautiful. Cock or not, she was perfect in every way imaginable. “Fuck, baby, here it comes.” She turned her face into my body and then released a muffled moan. She came, her warm cum shooting up, hitting me, hitting her, and then the final few eruptions billowed down over my fingers. It was a mesmerizing sight—totally seducing.

  I ended up coming immediately after, my own hot load filling up my underwear and her tight fist. Fuck, it felt amazing. I turned my head and rested it on hers as I caught my breath and gathered my composure.

  Carefully, I took her hand and brought it down to her cock, slipping it under the waistband of her cotton shorts. Then, I slipped myself out from our cuddle, laying her down gently on her side. She would wake up with her cock in her hand and that would hopefully explain the cum that was all over her—it was her own cum, after all. As I snuck away, her eyes were still closed and there was still that sleeping smile on her face.

  It was a close call, unless of course she was actually awake the whole time.

  CHAPTER IV

  I tried to convince myself she had been asleep, that she was completely unaware of our little mutual-masturbation session. If she was awake, she would have opened her eyes—right? Why would she pretend to be asleep? So I would keep going? Maybe she thought that if I knew she was awake, I wouldn’t have gone ahead with the jerk off. Maybe that was her way of getting an easy, guilt-free handjob.

  It was strange. Even now that I knew with absolute certainty that she was born a man, I was still wildly attracted to her. When I saw her walk past my bedroom, I couldn’t help but stare at those long, smooth legs and that perfect, perky butt. Whenever she took her open-door showers, I found myself peeking in, trying to get a glance of that big, thick cock of hers. Whenever I heard that water running, I would close my homework and I would creep into the hall. It was a few days later that I actually caught her masturbating.

  The door was open just enough that I could see the mirror, which reflected sight through a slit in the curtain. She had her big cock in her hand, and it was rock hard. She was stroking it quickly with a firm grip. Her free hand was above her head, holding onto the curtain rod. God, the way her tits jiggled as she stroked her beautiful rod—that was enough to get me hard. I could feel my face becoming warm, my cheeks red. I watched her bite her lip and tilt her head back. Her lips parted and she let out the cutest little moan. I watched her cock as it blasted out a seemingly endless load.

  I had to retreat into my own bedroom, locking the door behind me. I rubbed one out. I had no choice. It was a desperate attempt to control the insane levels of lust that were swirling in my body. It was only a temporary fix though. It seemed like every time I saw Kelsey, that lust would just fire back up, and I would be a sloppy mess all over again.

  “Want to help me bake some cookies?” she asked me one afternoon. She was wearing very little—a pair of tiny booty shorts, a loose-fitted crop top, and a cooking apron that made it look like she was wearing nothing at all.

  “I should probably finish this essay,” I said, though I had just finished the essay. I didn’t want to spend any unnecessary time around her. It was seeming like the more time we spent around one another, the more out of control my desires were becoming. I still had a few months left before I was moving out—I needed to control myself until then.

  “Oh, put it away for half an hour. You’ve been locked in your room all day. Come help me down in the kitchen. It’ll be fun,” she said. She had a big, cute smile on her face, and I couldn’t resist it. How can someone say no to a smile like that? How can someone deny themselves the opportunity to be around someone so beautiful. I was weak.

  “Okay, I’ll be down in five minutes,” I said, and then she skipped her way down to the kitchen with that big smile still on her face.

  I met her down in the kitchen, where she was busy combining flour and sugar and whatnot into a large bowl. Her back was to me and I could see the curve of her rump, poorly covered by her little shorts. She had such a perfect ass—so soft but somehow so perky. It had just the right bounce to it. “Hey,” she said, turning around. She had a little white smear on her nose. “Nice of you to join me.” She grabbed a cooking apron and brought it over to me.

  “I don’t mind if my clothes get dirty,” I said.

  “Oh, don’t be a drag,” she said, and then she went ahead and put the apron on for me, reaching around me to tie it up. I’ll admit, it was nice to have her pressed up against me while she fastened the thing. She smelled like vanilla and flowers. She stepped back. “You look good.”

  I looked down and realized the apron said ‘Kitchen Bitch’ on it. She laughed. “Have you ever made cookies before?” She turned around, returning to her mixing bowl.

  “No,” I said. My eyes drifted back down to that perfect, plump ass. I wanted to grab it and squeeze it with both of my hands. How could someone born a man possibly have an ass like that? It seemed impossible. Most models didn’t even have asses that perfect.

  “Your job is to separate the egg yolks from the egg whites,” she said, motioning me towards a carton of eggs and two bowls. I walked over to the little station, picked up an egg, and cracked it. I let the egg fall into the bowl, and then I thought for a moment about what to do next. How do I separate the white from the yolk?

  Kelsey was laughing at me. “What the heck are you doing?” she asked.

  “I’ll get it,” I said, picking up another egg and cracking it, this time leaving it in the cracked shell. When we were kids making Easter eggs, we would bore little holes in the bottom of the eggs to let the insides fall out. Would something like that work? I carefully began to open the egg up, but then it all fell into the bowl. Kelsey was laughing again.

  “Let me show you,” she said, and then she stepped up behind me. She reached her arms around me, pressing her warm body up against my back. She took my hands in hers and then began to guide me through the motions. “First, we crack the egg,” she said, bringing my hand and the egg down to the edge of the bowl. She rested her chin on my shoulder. My face was pressed up against her beautiful face. “Then we carefully break it into two halves.” She helped me do that, too. “And then we carefully transfer it back and forth, letting the whites fall out into the bowl.” She giggled. “Just like that. Let’s do another one.”

  I could feel the bulge of her cock against my ass as her warm beauty enveloped me. Her gentle perfume was making me crazy. She turned to face me, smiling, her lips just millimetres from mine. “See? You’re not so bad.” I kissed her. I had to. Her lips just looked so soft, so warm, so inviting. I couldn’t resist her overwhelming beauty. She kissed back. After a moment, her tongue penetrated my lips. My hands were all over her. Screw the cookies—and screw the fact she had a cock. I didn’t care anymore. She was more of a woman than any of the girls in my school. She was more beautiful than any woman I’d ever seen before. I wanted her. I needed her.

  I reached down, pushing my hand down her little shorts, and I grabbed her cock. I began to fondle it. I could feel it throbbing, growing, hardening. Her balls were soft and warm.

  Without breaking away from our kiss, she managed to get my pants down, around my ankles, and she was quick to get a firm grip of my cock. My heart was racing. This wasn’t just some innocent, sleepy handjob on the couch, this was the real deal. There was no wondering whether she was awake, no blurred lines.

  She spun me around. “Put your hands on the counter,” she demanded, so I did. I should have felt vulnerable, standing naked in the middle of the kitchen, the windows all open on a bright, sunny day, but I didn’t feel vulnerable. I was excited. All I could think about was her, her perfect body, her perfect cock. She reached around and placed a hand on my chest, gently sliding down, back onto my cock.

  Then I felt it: the tip of her hard, throbbing cock pressing up against my anus. “Ready?” she asked. But I wasn’t ready. I’d never had anything in ass before—especially not a big, throbbing dick. But I didn’t protest. I wanted her as close to me as humanly possible. I wanted her inside of me. I wanted her to do whatever she wanted with me. And that’s exactly what she did. Not waiting for an answer, she began to push in.

  My legs began to shake. Her cock was so big, so thick. There was no way I was going to be able handle it. I didn’t think it would actually fit, but she made it fit, cramming it deeper and deeper into my asshole. I clenched the edge of the counter. “You really are my kitchen bitch,” she said with a giggle, and it was true. With her soft hand fondling my erection, I would have done anything she asked me to do.

  She began to thrust in and out of me. It was a strange feeling at first—feeling totally stuffed one moment and then completely empty the next, and having no control over it whatsoever. But as I started to relax, the pleasure started pulsing through me. She was hitting a sweet spot. Every time the tip of her cock pressed against it, I melted a little bit more, my legs began to tremble a little bit harder. After just a few thrusts, I was a moaning mess, slumped over the kitchen counter, my head rolling from side to side in an increasing euphoria.

  “Your asshole is so tight,” she said. She reached down, and with her cock still ramming into my asshole, she began to draw little circles around my anus with her fingertip. It just pushed me even further over the edge. I’d lost control completely. I probably looked so foolish, moaning and squirming on that counter, but I couldn’t help it. I was on a different plane of reality where there was nothing but me, Kelsey, and an insurmountable amount of uncontrollable pleasure.

  It wasn’t long before I was coming, my cock blasting a hot, sticky load all over the kitchen cupboards and all over her soft, warm hand. “I’m going to come in your ass,” she said, leaning over me further, pressing her tits against my back as she fucked me like a dog from behind.

  I thought her cock in my ass was an intense euphoria—but her cum was an even greater experience. The feeling of it filling me up deep nearly made me come a second time. I wished the moment would have lasted forever, but of course it couldn’t. As she stepped back and slipped her cock out from my ass, I knew it was over. Our parents would be home from their honeymoon soon and things would inevitably change. There was no way my father would let me fool around with my transgender step-sister. If he found out about our little kitchen romp, he would probably kick me out of the house.