But Bill’s sister is going off to college soon. There are only a few sleepovers left before Bill’s easy ride is over. So he’s excited when his sister invites a new friend over: Morgan, a short chick who likes to wear suggestive outfits. At the end of the night, it’s Morgan who has an itch that needs scratched, but there’s one catch: she wasn’t always a chick.
CHAPTER I
Everybody loves Saturday nights—but I really loved Saturday nights. In the Deniker household, Saturday night was a magical time. My friends were always asking me to go out with them to bars and clubs and house parties, but I never wanted to leave my house—any other night, sure, but not Saturdays.
Because every Saturday night, all of the stars would align perfectly. My parents were always out on their ‘date night’. Sometimes they wouldn’t come home until very late, and sometimes they wouldn’t come home until the next morning. It was their chance to get away from their eighteen-year-old twin children. And with my parents out of the house, I could do anything. I could have thrown house parties of my own—but that’s not what I wanted to do. All I wanted to do on Saturday nights was be around. I just wanted to be present.
Because every Saturday night, my twin sister, Melanie, would invite her friends over for slumber parties. She’d been doing it nearly every week since we were eight years old. And back when we were eight, I wasn’t so thrilled about them. It wasn’t until puberty hit me like a roaring train that I realized they were the best thing ever: a house filled with girls my age, telling secrets, gossiping, wearing cute pyjamas—it was truly magical.
Let me let you in on a little secret: women are adaptable. Most women have high standards, until the options are slim, then they adapt. When there’s only a single guy around, and ten girls, it doesn’t matter if that single guy looks like the ugly forgotten member of the Adam’s Family—not that I was a bad looking guy. All I’m saying is: I didn’t have to try.
I would casually meander downstairs to the basement where the girls were set up. I’d pretend like I was just going to the mini-fridge to get myself a cola, and then I would watch as at least half a dozen young female gazes would turn towards me. I would slip into the back room where my dad kept his weight bench, and then I would do a few reps. I couldn’t lift much weight, but the girls didn’t need to know that—the clinking of the bar against the bench and the odd grunt was more than enough. After just a single set or two, I would hear the giggling and whispering, and I would know that I had become the topic of conversation.
My sister would roll her eyes, but she wouldn’t stop her friends from fawning over me, even though I was honestly average at best. You see—here’s the thing: it just takes one girl to make a single innocent little comment. Girls fall like dominoes; they don’t like feeling left out. So as soon as the first girl says, “Is your brother still single?” then the other girls become activated like robots. Maybe it’s a status thing—or a competition. Maybe they can’t help it. Maybe it’s just programmed into their feminine brains.
Usually by my third appearance downstairs, I would end up being invited over to chat. The girls would slowly inch closer and closer to me, like hungry animals. Their eyes would glow and sparkle at the sight of me. The hormone imbalance in that room was obvious, and it was glorious. When I was thirteen years old, I got my first kiss during one of my sister’s sleepover parties. A girl named Sandy Jenkins snuck away from the party while they were watching a movie. She came upstairs to the living room where I was playing video games, and then she sat down next to me. Without saying a word, she put her hand on my cheek, turned my head, and our lips locked. She even slipped a bit of sloppy tongue into her mouth. It was her first kiss as well. Before it was over, she awkwardly reached down and grabbed my cock as if she was trying to grab the TV remote. I tensed up and nearly screamed because she grabbed me so hard, but I managed to keep my cool. When the kiss was over, she looked into my eyes and said, “You think I’m the prettiest girl here, right?”
My heart was pounding and my head wasn’t thinking right. I probably shouldn’t have said what I said. “You’re in the top five for sure,” I said. Her face turned white and then she started to cry. She ran off to a bathroom and then she didn’t come out until long after I’d gone to bed. It’s possible that she went straight home. But it’s not like she actually liked me—she just wanted me to tell her that she was the prettiest girl at the slumber party.
I got my first blowjob two years later, also during one of my sister’s sleepover parties. I went downstairs to get a cola and saw that the girls were playing spin-the-bottle truth-or-dare. I overheard one of the girls asking another girl if she was a virgin. As I walked away, I heard them all giggling. It was an hour later when I was up in my bedroom and my bedroom door creaked open. A cute little blonde named Karen slipped into my room.
“Can I help you?” I asked.
She didn’t say anything. Her face was dark red and she was trying to hide an awkward smile. She tiptoed up to my bed and crawled up. Then she reached down and grabbed the waistband of my pyjama bottoms. “What are you doing?” I asked, without moving. But she didn’t answer. She just kept going. She pulled my bottoms down and I covered my cock with my hand. Then she took my hand and moved it aside. She lifted up my shaft, bent over, and she started to suck. It was a sloppy blowjob, though I didn’t know that at the time. She wasn’t able to get much of me in her mouth, so she mostly just sucked on my tip, and she still ended up gagging a number of times.
She bobbed her head and awkwardly scraped my tip with her teeth a few times. She used one of her hands to massage my ball sack, but her grip was too tight for it to be very pleasant. Still, I ended up coming in less than two minutes, without any warning. The first blast shot down her throat. Then she winced back while choking and gagging. The next shot got the side of her face. Then she jumped to her feet and recoiled back in terror. The rest of that cumshot ended up on my bed. She wiped her face with her sleeve and said, “What the fuck!?”
“What do you mean, what the fuck?” I said. I quickly pulled up my bottoms, even though my cock was still oozing cum.
“Why didn’t you warn me?” she said, trying again to wipe that sticky cum off of her cheek.
“I don’t know,” I said. “I didn’t know I was supposed to.”
“I don’t want to taste your cum—that’s so gross! Ew!” She spat on my floor and then left. But she was back in my bedroom the next weekend—and this time it wasn’t because she was dared to give me a blowjob during a game of spin-the-bottle truth-or-dare. This time, she just wanted to save her reputation—at least that was my best guess. She didn’t want me going around and telling my friends that she gave shitty blowjobs. And her blowjob this time around was much better, as if she’d spent the week looking up tutorials.
Everyone was asleep but her. She came into my room and woke me up by tapping on my shoulder. She shushed me and then she crawled under the covers. She sucked me off in a matter of minutes, and this time I warned her. As soon as I gave her the warning, she became completely still, holding my cock against her tongue as she braced herself. She gagged a little bit as my load filled her mouth. Then she pulled a tissue out from her pocket and spat my whole load out. She tried to give me a kiss, but I winced away. I didn’t want to taste my own cum. “Gross. What’s wrong with you?” I said. She slapped my face and then she snuck back downstairs to her sleeping bag.
It was just a year later when I lost my virginity—also during one of those sleepover parties.
My sister had a new friend who was visiting the house for the first time: Felicity Andrews. Felicity already had a whorish reputation at school. I’d heard that she slept with every guy on the basketball team in a single weekend. According to one source, she slept with all of them at the same time: they all took turns coming in her pussy while she laid on her back with her legs spread out. The same source claimed that they made the guy who came last eat all the cum out of her sloppy cunt when it was all over. Though I didn’t
believe that story—not until I went to use the bathroom during my sister’s sleepover party and there was a knock at the door.
“I’ll be done in a minute,” I called out.
And then there was that knock again.
“I said I’ll be done in a minute!”
“Open up!” a female voice hushed. So I zipped up my pants and I opened the door slightly. There she was: Felicity Andrews, with her long black hair and her plump duck lips. She slipped into the bathroom without an invite and she closed the door. Then she started taking her clothes off.
“What are you doing?” I asked. I knew the girls weren’t playing truth-or-dare. I could still hear the romantic comedy movie they had put on.
“You’re going to fuck me,” she said. “I want to feel your cum inside of my panties for the rest of the night.” And in that moment, I believed the whole wild story of her fucking the whole basketball team.
And even though I was worried that she might have some sort of STI, I still fucked her. I felt her small, soft tits, and then I fingered her pussy for a few minutes. She bent over the vanity and reached back with both hands to spread her butt cheeks wide. “Do you like my butthole?” she asked. “I just bleached it yesterday.” I didn’t know what that meant.
So I just said, “It looks tight.”
“It is tight. Try sticking your finger up it.” I pressed the tip of my finger into her asshole and then she clenched tight. “I bet you can’t go any further.” She giggled. I pushed and managed to get my finger in further—but it was very tight. “Have you ever fucked a girl in the asshole before?” she asked.
“No,” I said.
“Do you want to?” she asked.
“I guess so.”
She reached back suddenly and grabbed my cock. She slid it up to her asshole and then left it there for a moment while she spat into her hand and reached back again to lubricate my shaft. “But I want you to come in my pussy,” she said. “So tell me when you’re close and then we’ll switch holes. Okay?”
“Can’t you get an infection doing that?” I said.
“No—that’s a myth,” she said.
She firmly grabbed my cock and began to press it into her back hole. She squirmed slightly and then she moaned as I penetrated her. “Oh shit,” she said. “You’re actually big.”
“Really?” I asked.
“Yeah. It might be too tight. Maybe we should just do it in the pussy.” But it was too late—I had my sights firmly set on that tight asshole. I held her hips firmly and I kept thrusting forward. She kept squirming. She let a muffled high-pitched squeal out from her lips, and then she put her face down on the vanity counter. “Oh God,” she said. “It’s too tight. It’s just too tight.”
“It’s fine,” I said. “You’re fine.” I watched as my cock disappeared into her rectum. Though she wasn’t able to take the whole thing. I only got halfway in before she reached back and pressed the palm of her hand against my pelvis.
“That’s enough!” she said. “Just fuck me with that.”
“That hardly just my tip,” I said, exaggerating a little bit.
“It’s enough,” she said. So I began to pump her with just half of my cock. It still felt good. Her butthole was warm and her spit made it nice and wet. She was tight enough that I didn’t last more than a couple of minutes. But I forgot to warn her about my cumshot. I ended up sinking my fingertips into her sides and then coming inside of her asshole.
“Hey!” she said. “I said to come in my cunt, you idiot!” As soon as I pulled out, she cupped her hand at her asshole and let the creampie ooze out. Then she stuffed my cum into her pussy. She moaned and squirmed and had an intense orgasm as she pressed her fingers into her slit. It was a mesmerizing sight, and also a very gross sight at the time.
Felicity wasn’t the only girl I got to fuck during one of my sister’s sleepover parties. Many girls followed. I was fucking a new girl every month. I was starting to lose count of how much virginity I was taking. So many girls came into my room to suck my cock. I got so many sloppy blowjobs, and the occasional very good blowjob—though I kind of liked the sloppy ones more, knowing that my cock was probably the first cock to enter into those girls’ mouths. I started keeping condoms in my bedside table. I would make the girls put the condoms on my cock for me. They loved it—giggling the whole time, getting to do something in real life that they’d only ever done in sex-ed class with a wooden model.
I made the mistake of telling my close friends about how often I got laid. They started begging me to invite them over on Saturday nights, but I never did. I knew that things wouldn’t be the same if I weren’t the only male in the house. I knew that sex wouldn’t come so easily if I had competition—even if I was still the best looking and the most experienced guy in the house. A few of my friends showed up at the house and knocked on the door. I sent them away. The next week, they came back and tried to break in through an unlocked bathroom window. I caught Parker, a guy from my English class, and sent told him to buzz off. Then, the next week, while I was getting my cock sucked by a new girl, I noticed a face outside of my bedroom window. Someone was watching from my backyard. I got up and shut the curtains. As I closed those curtains, I recognized Parker again. “What is it?” the girl asked, rising to her feet.
“It’s nothing—I guess I’m just feeling a little bit paranoid tonight,” I said. Then I pushed her back down onto her knees and pulled her head back into my crotch. She kept sucking me. I quickly learned that girls liked it when I held their heads in place and fucked their mouths by thrusting back and forth. I don’t know why they liked it—it seemed a little bit degrading. But it also seemed like girls were looking for degrading: the more degrading, the better.
They loved it when I cuffed them to my bed frame with the cheap cuffs I bought at the dollar store. Girls would come instantly as soon as I got my hands around their throats. One girl begged me to slap her face while I was pumping her, so I did. She ended up squirting all over my bed sheets. I didn’t mind—it served as a nice reminder for the rest of the night of how awesome my life was, and how much I had to look forward to next week.
CHAPTER II
It was a Saturday night near the end of July when my twin sister invited a new girl over for a sleepover, along with her usual friends. I didn’t recognize the girl from school, which we’d just graduated from a month before. She was short, with long straight blonde hair that reached all the way down her back, nearly touching her waist. She wore a white lace headband to hold her hair back—the same sort of headband a young girl might wear.
And it seemed like the ‘young girl’ look was the look she was going for. She wore a pink plaid skirt and a white short-sleeved blouse, which she kept tied up at her sternum, as if she was about to step onto the set of some schoolgirl-themed porn shoot. But even though her outfit was sexy and suggestive, she had an aura of innocence about her. I could tell—from lots of experience—that she was a virgin.
Her gaze met mine as my sister led her through our house towards the basement where every sleepover had taken place over the past decade. “Here’s the kitchen. Feel free to help yourself to anything in the pantry here or in the fridge,” my sister said. But the new girl wasn’t listening to my sister. She was staring at me. Her eyes were wide, as if she was nervous. Maybe my sexual energy was making her uneasy. Maybe she was having feelings that she didn’t expect to have when she walked into our house expecting a full-female sleepover party. I knew that look well. It was the same look they all made when they saw a man for the first time, after seeing woman after woman after woman…
My sister turned to look at me. She saw me staring at the new girl, which didn’t bother me. At least it didn’t bother me until an hour later, when my sister came upstairs to grab a bottle of white wine from the fridge. She was alone and her friends were all downstairs watching some reality TV show and chatting loudly. She grinned at me and said, “Please don’t tell me you think she’s cute.”
“Who?
Your schoolgirl friend?” I said. “Why?”
“Just be honest with me: what do you think of her?”
I shrugged my shoulders. “She’s alright. Why are you being so weird?”
“Would you kiss her if I gave you five bucks to kiss her?” My sister’s grin grew even bigger. Was she trying to coax me into liking this girl? Did the girl say something about me down in the basement? Did she like me?
“Sure—why not?”
My sister covered her mouth and then she started laughing.
“What’s the matter with you? Cut it out! Quit being a weirdo.”
“You just said that you would kiss a boy for five bucks.”
My heart stuttered. I opened my mouth to reply, but words were slow to come to the surface. “W—What did you just say?”
“She’s a transgender, Jared. She just started transitioning a few months ago. Maybe if you look closely enough at her, you’ll recognize her.”
I didn’t believe my sister at first. I figured she was just trying to mess with me. Maybe the girls thought it would be funny to toy with my head a little bit.
But an hour later, I learned that it was true. The new girl really was a transgender. I was going down to grab a cola from the mini-fridge when I heard her speaking. She looked good, with her long hair and her smooth skin—but that voice still needed work. It wasn’t quite feminine, almost as if she had inhaled a little bit of helium before opening her mouth.
She looked at me again. This time, I looked away quickly, feeling strangely flustered and embarrassed. I wondered if my sister told everyone that I would have kissed her for five bucks. What if she told the transgender girl? What if the transgender girl now thought that I was interested in her?
I grabbed my cola and rushed back upstairs. I turned off the television in the living room and then I went to spend the rest of my night in the bedroom. My ego was shaken. I knew that I would recover. I knew that I just needed to let things settle. The girls could have their fun and giggle a little bit at my expense, and then they would remember that I’d fucked nearly half of them, so they really didn’t have much to laugh about. And maybe I needed a night to remember that I’d fucked almost half of them.
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