CRAIG
One’s outlook on life can change in a moment. That’s what I’ve noticed since I met Bailey – my first real crush. Don’t get me wrong, I just turned 18 and have had plenty of feelings for girls over the years, even a few short relationships. But I’ve never been this helplessly entranced by someone. All it takes is a flash of her dimpled smile, or even better, a cute giggle at something I said in class, and my week is fulfilled.
Bailey’s a year below me and I didn’t pay her much attention until this year. She always seemed to have a decent number of friends and I knew her name due to sports and it being a small town and what not, but she was a late bloomer. I remember her being skinny, and girlish looking, with protruding ears that were too big for her head. My friends and the other guys at school never talked about her, instead focusing on the girls that had a huge rack or a round ass by freshman year. But now, all that has certainly changed. Some girls, I don’t know, when they go from fifteen…to sixteen…to seventeen, and you don’t see them every day during that time frame, it feels like…what the FUCK happened?!
I began noticing Bailey during the late summer, before the school year started. I was entering my senior year, which I am currently completing. I’m on the football team and Bailey plays soccer in the fall and our preseason workouts overlap. I was cleaning up after practice one afternoon and going to hit up our new cold plunge tubs that the school had purchased. Everyone was so excited over those stupid tubs because it makes us feel like we’re professional athletes or something.
I was walking from our locker room to the pool and weights area where the tubs were located. Partly because I wanted to fit in with the other guys, partly because it was blistering hot, and partly because I wanted to show off my abs (that I only have because I’m skinny), I was not wearing a shirt. A cute girl with round, brown eyes and dark curly hair emerged from the girls’ locker room. She was dressed in short shorts, a t shirt, and high socks with shin guards. She had nice, tanned, toned legs. I remember my initial thought being who is THAT?
“Hi Craig!” The girl smiled brightly at me. I was surprised, and wondering how she knew my name. Hearing a hot girl say your name might be the greatest sound ever. I eventually recognized the girl as Bailey.
“Oh…sup Bailey,” I murmured, trying to sound cool.
“Getting in the tub?” Her eyes briefly scanned down my torso and back up to my face.
“Yep.”
“I’m jealous…it’s so hot out! Wish I could just skip practice and jump in,” She said. Then she strutted away slowly with a newfound confidence and that was it, believe it or not. That was all it took for me. A brief, 10 second interaction with a sweet, pretty girl, and the spark was ignited.
*****
I made it a habit to run into Bailey as often as I could for the remainder of the summer. Some interactions lasted longer than others. But she would always greet me with her kind, bright smile. My obsession grew.
I creeped on her Instagram. I subtly brought her up in conversations with my buddies – hoping to gain more info on her – whether she was dating anyone, if other guys had noticed her, who her friend group was, etc. I even went out of my way to be nice to her weird little brother Ben.
I saw him working at the library one day when I was picking up my summer reading assignment. I knew him from school but typically paid him no mind. In fact, it took me a second to make the connection that he was Bailey’s brother. They were so different. Bailey was perky, outgoing, and seemingly involved in everything. Ben, on the other hand, would not surprise me if he went postal one day. He was quiet, and odd, and…angry. I never saw him anywhere except school and, now, at the library.
“Hey man, how’s your summer been?” I asked him when I was checking out my book.
He didn’t look up at me. “Okay,” he mumbled.
“…Do anything fun?” I tried to sound welcoming but he just shook his head.
“Not really.”
“Errr….you excited for school to start back up?” I was running out of things to talk about. You think you have good social skills until you’re locked in a one-on-one with an awkward partner.
“Why would I be excited for that.” It was a statement, not a question. I tried to answer anyway.
“I dunno, see some friends. Parties and fun shit going on….hot girls…” I cringed when thinking back at that last part. Growing up I always hated it when the older guys tried to act cool and bring up girls to me. Plus, for all I know, Ben was gay.
“Okay,” was all he said.
“You’re gonna be…a sophomore now. Right?”
“Yes.”
“Alright, well….nice seeing ya! I’ll see ya at school I guess.” I made my way to the door and heard him let out a little chuckle. Or maybe it was a scoff. I don’t know. Kid was weird.
*****
You can imagine my delight when Bailey arrived in my drama class on the first day of school. I saw her in the hallways in the morning but was disappointed she didn’t notice me. She was naturally surrounded by a group of friends. I was extra disappointed she was not in either of my morning classes and was beginning to lose hope. It sounds stupid, but you really do get to know the kids in your classes better than the ones who aren’t. Then, fourth period came and Bailey came waltzing into the room like a slow-motion scene out of a movie. I acted aloof, trying to hide my enthusiasm.
Drama was a joke of a class, and almost everyone took it to lighten up their schedule. The teacher, Ms. Kealoha, let us goof off – though we did have to do performances. I had several of my friends in the class and so I felt confident and extroverted. Bailey smiled and said hi to me as the class settled in. This was shaping up to be a great senior year for me.
A Tangled Web
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drew
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Re: A Tangled Web
BEN
Sometimes, okay most of the time, I can’t stand my older sister, Bailey. She’s a stuck up, 17-year-old bitch. She’s popular and does well in sports, school, and anything else she tries. Oh, and of course, she’s hot. At least every guy at school drools over her. That’s a fairly new thing I noticed over the summer and once the new school year started. It’s annoying. Bailey has a nice body, I guess, from playing sports. Personally, I think her face is mid, but then again, I’m her brother, and biologically programmed to not find it overly attractive. I don’t let her walk all over me like the tools at school do.
Meanwhile, when it comes to school, I’m a nobody. I’m 15, skinny-fat with acne, and sucked at sports my whole life – not that I’d care to participate in the mindless ball-chasing anyway. People think I’m smart, and I am, but I don’t get great grades. I think the shit they make you learn is pointless in the real world. Also, I get the sense the teachers think I’m creepy and weird just like all the girls at school. I don’t have a lot of friends, but don’t get bullied too much, probably because of Bailey. I mainly just get ignored and people make weird faces when I talk.
Bailey’s cunt friend Leslie, however, does like to pick on me. Mainly, when she’s over at our house hanging out with my sister, which is often, because she lives nearby. Leslie thinks she’s hot shit but I’m not sure why. She’s just one of those loud, obnoxious girls who has a lot of friends because she intimidates people.
“Whatsup Ben, did you wear THAT to school?” Leslie mocked me one day after school at our house.
“Yeah?” I said back. Leslie and my sister laughed. The three of us were home alone. I was minding my own business on my computer. I’m not sure why they felt the need to bother me.
“Ben, you really need to let Mom take you shopping. Update the wardrobe, you know,” Bailey said.
“Whatever,” I mumbled.
“You got a date for Homecoming, Ben?” Leslie asked.
I ignored her.
“C’mon man, gonna be a blast. You could lose your V-card at the after-party!” She and Bailey burst out laughing. I didn’t respond to them and they finally went away.
Of course, my peace and quiet did not last long. About an hour later Leslie came wandering back over to my room.
“Hey Ben, you never answered the question from earlier,” she said.
I said nothing.
“You still a virgin? Not a big deal, I bet a lot of guys in your grade are. Let us get you laid, you’ll be a step ahead of all them.”
“Hahaha, Ben’s never even kissed a girl before!” Bailey laughed.
“I have too!” I snapped back at her.
“Oh yeah, who? We can text her and confirm!” Bailey said, standing in my doorway, hands on her hips. Now I regretted even entertaining their stupid question.
“Fuck off, you don’t know her!” I said.
“Ah, the ol’ ‘she goes to another school’ huh?” Bailey said. “Ben, I’m pretty sure I know every girl you’ve ever even TALKED to in your life.”
“Don’t you guys have anything better to do?” I said.
“Hey, I have a fun idea!” Leslie started.
“What’s that?” Bailey laughed.
“What do you say we help Ben see his first REAL LIFE vagina!”
“Shut up. I’ve seen one before,” I said.
“No, you haven’t!” Bailey accused. “Other than all the porn you’re addicted to.”
“I don’t watch porn!” I protested in an obvious lie.
“Yeah, okay,” Bailey said sarcastically.
“Well, Ben, do you WANT to see one?” Leslie asked. I just shook my head at her and tried to go back to ignoring them.
“Here’s your chance Ben….” Suddenly, Leslie pinned Bailey’s hands behind her back.
“Hey!” Bailey giggled in playful manner. “Let go!”
“Look over here, Ben. This may be the moment you’ve been waiting for! All those pent-up hormones begging for release!” Leslie continued.
Leslie was a bigger girl. Not huge, by any means, but she did play soccer, basketball, and softball and was definitely stronger than Bailey. She had no trouble holding my sister in place, though, I don’t think Bailey was taking this too serious at the moment.
“Ohhhh Bennnny,” Leslie said in a cartoonish, teasing manner. She grabbed Bailey’s cotton shorts and slithered them down and off her hips. I saw some thin, stretchy pink underwear pop into view and I looked back at my computer.
“Leslie!” Bailey cried out. She seemed a bit startled her friend had actually pulled her shorts down, but was still laughing. I turned back briefly, and saw that Bailey’s shorts were at her ankles. She had tanned, toned thighs and her panties hugged her hips, contrasting nicely with her skin. They were skimpier than I would have thought and my groin tingled, which confused me.
“Alright, Ben, you wanna come do the honors?”
“Hahaha, Leslie that’s enough! Let’s leave him alone,” Bailey said. She was beginning to give more of an effort to free her wrists.
“No c’mon, he’s never gonna see one!” Leslie said.
“That’s his problem, not ours,” there was some anxiety creeping into Bailey’s voice.
“Alright Ben, three….two…..”
“Leslie stop!” Bailey was starting to wiggle around.
“ONE!””
“Les, DON’T!!!”
Leslie had a huge, mouth open, shit eating grin on her face as she grabbed my sister’s underwear with one hand and swiped them to the floor! HOLY SHIT! I couldn’t believe she actually did it! And neither could Bailey, she was squirming around and screaming like crazy now.
“OHMYGOD, LES STOP!!! LET GO! LET GO!!” Bailey cried out.
I couldn’t help myself and took a look. I never in a million years would have guessed how thrilling it would be to discover my sister shaved her coochie TOTALLY bare!! I mean, I guess it shouldn’t be too surprising. I figured girls my age did, I just never really thought about her doing it. But I was too obvious in my enjoyment.
My eyes met Bailey’s, and she was staring a hole through me.
“GET A GOOD LOOK, FREAK?!” she furiously screamed. Her face was plum red.
“Bahahahaha!! He can’t take his eyes off it!” Leslie cackled. She was laughing so hard that she released my sister and Bailey quickly pulled her underwear and shorts up.
“I wasn’t looking, that’s gross!” I argued.
But the damage was done and both girls had witnessed my eyes going wide and my mouth agape.
“I bet he’s got a boner!” Leslie continued to roar.
She was right, but there was NO way I was gonna let them find that out. I turned away from them, back to my computer.
“I do not you stupid cunt!” I screamed. “Leave me alone!”
“Oh yeah?!” Leslie asked. She then bull-rushed over to me and began to grope me as I tried to cower. It didn’t take long for her to feel it. “OH, SHIT HE DOES!” She announced with glee. “HE’S ACTUALLY HARD, B! BAHAHAHAH!”
“AM NOT!” I shouted.
Leslie ran back toward my sister dying from laughter. Bailey gave a look of absolute repulsion.
“You’re freaking gross, dude,” she snapped. “Don’t you watch enough porn to not have to get off to your own sister!?”
“FUCK OFF!” I shouted.
Finally, they did as I commanded. Bailey and Leslie moseyed off, and left me alone for the rest of the afternoon. I was utterly humiliated….but a new infatuation had been birthed in me.
Sometimes, okay most of the time, I can’t stand my older sister, Bailey. She’s a stuck up, 17-year-old bitch. She’s popular and does well in sports, school, and anything else she tries. Oh, and of course, she’s hot. At least every guy at school drools over her. That’s a fairly new thing I noticed over the summer and once the new school year started. It’s annoying. Bailey has a nice body, I guess, from playing sports. Personally, I think her face is mid, but then again, I’m her brother, and biologically programmed to not find it overly attractive. I don’t let her walk all over me like the tools at school do.
Meanwhile, when it comes to school, I’m a nobody. I’m 15, skinny-fat with acne, and sucked at sports my whole life – not that I’d care to participate in the mindless ball-chasing anyway. People think I’m smart, and I am, but I don’t get great grades. I think the shit they make you learn is pointless in the real world. Also, I get the sense the teachers think I’m creepy and weird just like all the girls at school. I don’t have a lot of friends, but don’t get bullied too much, probably because of Bailey. I mainly just get ignored and people make weird faces when I talk.
Bailey’s cunt friend Leslie, however, does like to pick on me. Mainly, when she’s over at our house hanging out with my sister, which is often, because she lives nearby. Leslie thinks she’s hot shit but I’m not sure why. She’s just one of those loud, obnoxious girls who has a lot of friends because she intimidates people.
“Whatsup Ben, did you wear THAT to school?” Leslie mocked me one day after school at our house.
“Yeah?” I said back. Leslie and my sister laughed. The three of us were home alone. I was minding my own business on my computer. I’m not sure why they felt the need to bother me.
“Ben, you really need to let Mom take you shopping. Update the wardrobe, you know,” Bailey said.
“Whatever,” I mumbled.
“You got a date for Homecoming, Ben?” Leslie asked.
I ignored her.
“C’mon man, gonna be a blast. You could lose your V-card at the after-party!” She and Bailey burst out laughing. I didn’t respond to them and they finally went away.
Of course, my peace and quiet did not last long. About an hour later Leslie came wandering back over to my room.
“Hey Ben, you never answered the question from earlier,” she said.
I said nothing.
“You still a virgin? Not a big deal, I bet a lot of guys in your grade are. Let us get you laid, you’ll be a step ahead of all them.”
“Hahaha, Ben’s never even kissed a girl before!” Bailey laughed.
“I have too!” I snapped back at her.
“Oh yeah, who? We can text her and confirm!” Bailey said, standing in my doorway, hands on her hips. Now I regretted even entertaining their stupid question.
“Fuck off, you don’t know her!” I said.
“Ah, the ol’ ‘she goes to another school’ huh?” Bailey said. “Ben, I’m pretty sure I know every girl you’ve ever even TALKED to in your life.”
“Don’t you guys have anything better to do?” I said.
“Hey, I have a fun idea!” Leslie started.
“What’s that?” Bailey laughed.
“What do you say we help Ben see his first REAL LIFE vagina!”
“Shut up. I’ve seen one before,” I said.
“No, you haven’t!” Bailey accused. “Other than all the porn you’re addicted to.”
“I don’t watch porn!” I protested in an obvious lie.
“Yeah, okay,” Bailey said sarcastically.
“Well, Ben, do you WANT to see one?” Leslie asked. I just shook my head at her and tried to go back to ignoring them.
“Here’s your chance Ben….” Suddenly, Leslie pinned Bailey’s hands behind her back.
“Hey!” Bailey giggled in playful manner. “Let go!”
“Look over here, Ben. This may be the moment you’ve been waiting for! All those pent-up hormones begging for release!” Leslie continued.
Leslie was a bigger girl. Not huge, by any means, but she did play soccer, basketball, and softball and was definitely stronger than Bailey. She had no trouble holding my sister in place, though, I don’t think Bailey was taking this too serious at the moment.
“Ohhhh Bennnny,” Leslie said in a cartoonish, teasing manner. She grabbed Bailey’s cotton shorts and slithered them down and off her hips. I saw some thin, stretchy pink underwear pop into view and I looked back at my computer.
“Leslie!” Bailey cried out. She seemed a bit startled her friend had actually pulled her shorts down, but was still laughing. I turned back briefly, and saw that Bailey’s shorts were at her ankles. She had tanned, toned thighs and her panties hugged her hips, contrasting nicely with her skin. They were skimpier than I would have thought and my groin tingled, which confused me.
“Alright, Ben, you wanna come do the honors?”
“Hahaha, Leslie that’s enough! Let’s leave him alone,” Bailey said. She was beginning to give more of an effort to free her wrists.
“No c’mon, he’s never gonna see one!” Leslie said.
“That’s his problem, not ours,” there was some anxiety creeping into Bailey’s voice.
“Alright Ben, three….two…..”
“Leslie stop!” Bailey was starting to wiggle around.
“ONE!””
“Les, DON’T!!!”
Leslie had a huge, mouth open, shit eating grin on her face as she grabbed my sister’s underwear with one hand and swiped them to the floor! HOLY SHIT! I couldn’t believe she actually did it! And neither could Bailey, she was squirming around and screaming like crazy now.
“OHMYGOD, LES STOP!!! LET GO! LET GO!!” Bailey cried out.
I couldn’t help myself and took a look. I never in a million years would have guessed how thrilling it would be to discover my sister shaved her coochie TOTALLY bare!! I mean, I guess it shouldn’t be too surprising. I figured girls my age did, I just never really thought about her doing it. But I was too obvious in my enjoyment.
My eyes met Bailey’s, and she was staring a hole through me.
“GET A GOOD LOOK, FREAK?!” she furiously screamed. Her face was plum red.
“Bahahahaha!! He can’t take his eyes off it!” Leslie cackled. She was laughing so hard that she released my sister and Bailey quickly pulled her underwear and shorts up.
“I wasn’t looking, that’s gross!” I argued.
But the damage was done and both girls had witnessed my eyes going wide and my mouth agape.
“I bet he’s got a boner!” Leslie continued to roar.
She was right, but there was NO way I was gonna let them find that out. I turned away from them, back to my computer.
“I do not you stupid cunt!” I screamed. “Leave me alone!”
“Oh yeah?!” Leslie asked. She then bull-rushed over to me and began to grope me as I tried to cower. It didn’t take long for her to feel it. “OH, SHIT HE DOES!” She announced with glee. “HE’S ACTUALLY HARD, B! BAHAHAHAH!”
“AM NOT!” I shouted.
Leslie ran back toward my sister dying from laughter. Bailey gave a look of absolute repulsion.
“You’re freaking gross, dude,” she snapped. “Don’t you watch enough porn to not have to get off to your own sister!?”
“FUCK OFF!” I shouted.
Finally, they did as I commanded. Bailey and Leslie moseyed off, and left me alone for the rest of the afternoon. I was utterly humiliated….but a new infatuation had been birthed in me.
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mikewozere
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CursedSavinkov
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Re: A Tangled Web
Welcome back! Can't wait to see where this story leads!
I'll have another reason to check in here regularly...
I'll have another reason to check in here regularly...
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drew
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Re: A Tangled Web
BAILEY
My brother has been soooo weird lately, and I’m curious if his behavior is normal?
I’ve always been blessed with a lot of friends growing up. But this past summer going into the school year I’ve been getting way more attention from boys. Meanwhile, my little brother Ben has sort of gotten….left behind?
I personally think it’s his attitude. Especially towards girls. I mean, he’s not ugly. I don’t think anyone would mistake him for being hot per se, but he’s an average looking sophomore guy. He’s just such a jerk to girls! It’s like he thinks we’re all these slutty whores who have made a pact to personally screw with him.
Anyway, since I’ve started hanging out with boys, Ben’s been extra awful. He’ll make comments about me wearing too much makeup (when I’m barely wearing any) or dressing “skanky.” I’m not sure why he can wear shorts and a t shirt to school when it’s 90 degrees out, but when I do it, I’m a ho. And he thinks every guy – well, two guys – that I’ve brought over to the house is some fake douche who’s just trying to get some.
It also makes no sense how judgy he is because we all go to church every weekend as a family but I constantly see him rolling his eyes, scoffing, and making sarcastic comments about religion. He clearly doesn’t believe any of it, yet, he thinks I should abide by all these Christian values?
He’s just really annoyed me lately and one afternoon after school, I was probably overly harsh on him.
My friend Leslie and I were hanging out. Leslie and I play soccer together and she lives down the road so we grew up together. She’s really funny, though I admit, sometimes she crosses the line. She’s picked on Ben in the past and I’ve had to tell her to stop. Usually, she’ll listen and just not say anything to him for a few weeks.
One afternoon, she began teasing him about homecoming.
“C’mon man, how else are you gonna laid?” Leslie mocked.
“Let’s leave him alone, Les,” I said. I really don’t get satisfaction out of teasing Ben.
“Alright,” Leslie agreed.
The two of us went to my room, but eventually, we got thirsty and went back out for a drink. Ben hadn’t moved, and was still sitting at his computer. I swear he was addicted to that thing. Leslie spotted him.
“Ben, you never answered earlier, I really think you should go to homecoming!”
Ben ignored her.
“Most guys your age are virgins, dude, it’s nothing to be ashamed about. I PROMISE you, we can get you laid if you let us help, then you’ll be one step ahead of most the guys in your grade!”
“Fuck off, I’m not a virgin!” Ben snapped. I don’t know why he felt the need to lie. The fact that he was OBSESSED with making sure I wasn’t having sex, but then felt the need to brag that he was doing it really aggravated me. Just more of his hypocrisy.
“Ben, you are too!” I said. “I’ve never even heard of you kissing a girl before!” I shouldn’t have said that. Not in front of Leslie.
“Bahahaha!” Leslie started laughing.
“I’ve kissed plenty of girls before,” Ben was trying to act cocky but he was too awkward.
“Who?” I asked.
Then he tried to make up some stupid story about a girl at another school. I’m like dude you’re literally home or at school all day every day. You never leave your computer! But I didn’t actually say it. Instead, I just tried to get Leslie to leave him be. There was no point in arguing with him. All three of us knew he was lying. But Leslie kept badgering him.
“Ben, I can even show you your first real life vagina today!” She said.
Which was probably true, I thought. Leslie had no problems getting naked or flashing people – even guys. She certainly wasn’t shy about showing off and saw it all as a joke.
Then Ben started talking about how he’s seen naked girls before.
“You need to stop looking at so much porn,” I said.
He denied it. If he wasn’t so proud and being such an ass, Leslie actually probably would flash him, I thought, at the time. But when I was thinking that, she grabbed MY wrists.
“Ben! Here’s your chance! Wanna see your sister’s hoohaa?!” Leslie teased.
“Les!” I laughed. I just figured she was joking, but she was holding me tight.
“Oh Bennny! Look over here!” Leslie continued. She then slowly worked my shorts down past my hips. My underwear came into view! Ben’s face was beat red. He was just staring at his monitor, but then Leslie pulled my shorts past my butt and they dropped to my ankles. Ben looked back over and I saw his eyes run up and down my legs. Gross!
“Leslie that’s enough! Stop teasing him!”
“Ben, you wanna do the honors?” She ignored me.
Ben remained in his chair.
“LES STOP!”
“Oh, c’mon, he’s never gonna see one!” She laughed.
“Well, mine shouldn’t be the first!” I protested. I began trying to struggle to get away, but it was no use. Leslie prolly has 20 or 30 pounds on me.
“THREE!.....” She began counting.
“TWO!....” I kept trying to escape.
“ONE!” Leslie announced with glee, then pulled my underwear down to my ankles!!
OHMYGOD!!! I screamed as my you-know-what was exposed in front of Ben….and he was staring! SOOOO FRICKIN GROSS!
“STOP LOOKING, FREAK!” I snapped, taking my anger out on Ben.
“BAHAHAHAHAAHA he can’t keep his eyes off it!” Leslie was laughing hysterically. She let me go, and I quickly pulled my pants up. “You think he’s got a boner!?” She continued. I was so irritated with her, and didn’t answer. “I bet he does!”
“I do not you fucking cunt!!” Ben screamed at her with language I’d never heard him use. Wrong move.
“Let’s find out!” Leslie yelled and sprinted over to Ben. She began groping my little brother and then shouted out triumphantly. “He does! He’s hard B! He’s hard!” She continued to cackle.
I was so embarrassed and annoyed, and again, I took it out on Ben.
“You’re so gross dude, don’t you watch enough porn!? Why do you have to check out your own sister!?”
I stormed off back to my room and Leslie followed. I made her promise not to tell anyone at school about what happened. I didn’t think she’d listen, but then I told her Ben might tell on her for grabbing him and she could get in big trouble, especially since she’s 18. Really, I was just trying to spare myself the humiliation, but she bought it.
My brother has been soooo weird lately, and I’m curious if his behavior is normal?
I’ve always been blessed with a lot of friends growing up. But this past summer going into the school year I’ve been getting way more attention from boys. Meanwhile, my little brother Ben has sort of gotten….left behind?
I personally think it’s his attitude. Especially towards girls. I mean, he’s not ugly. I don’t think anyone would mistake him for being hot per se, but he’s an average looking sophomore guy. He’s just such a jerk to girls! It’s like he thinks we’re all these slutty whores who have made a pact to personally screw with him.
Anyway, since I’ve started hanging out with boys, Ben’s been extra awful. He’ll make comments about me wearing too much makeup (when I’m barely wearing any) or dressing “skanky.” I’m not sure why he can wear shorts and a t shirt to school when it’s 90 degrees out, but when I do it, I’m a ho. And he thinks every guy – well, two guys – that I’ve brought over to the house is some fake douche who’s just trying to get some.
It also makes no sense how judgy he is because we all go to church every weekend as a family but I constantly see him rolling his eyes, scoffing, and making sarcastic comments about religion. He clearly doesn’t believe any of it, yet, he thinks I should abide by all these Christian values?
He’s just really annoyed me lately and one afternoon after school, I was probably overly harsh on him.
My friend Leslie and I were hanging out. Leslie and I play soccer together and she lives down the road so we grew up together. She’s really funny, though I admit, sometimes she crosses the line. She’s picked on Ben in the past and I’ve had to tell her to stop. Usually, she’ll listen and just not say anything to him for a few weeks.
One afternoon, she began teasing him about homecoming.
“C’mon man, how else are you gonna laid?” Leslie mocked.
“Let’s leave him alone, Les,” I said. I really don’t get satisfaction out of teasing Ben.
“Alright,” Leslie agreed.
The two of us went to my room, but eventually, we got thirsty and went back out for a drink. Ben hadn’t moved, and was still sitting at his computer. I swear he was addicted to that thing. Leslie spotted him.
“Ben, you never answered earlier, I really think you should go to homecoming!”
Ben ignored her.
“Most guys your age are virgins, dude, it’s nothing to be ashamed about. I PROMISE you, we can get you laid if you let us help, then you’ll be one step ahead of most the guys in your grade!”
“Fuck off, I’m not a virgin!” Ben snapped. I don’t know why he felt the need to lie. The fact that he was OBSESSED with making sure I wasn’t having sex, but then felt the need to brag that he was doing it really aggravated me. Just more of his hypocrisy.
“Ben, you are too!” I said. “I’ve never even heard of you kissing a girl before!” I shouldn’t have said that. Not in front of Leslie.
“Bahahaha!” Leslie started laughing.
“I’ve kissed plenty of girls before,” Ben was trying to act cocky but he was too awkward.
“Who?” I asked.
Then he tried to make up some stupid story about a girl at another school. I’m like dude you’re literally home or at school all day every day. You never leave your computer! But I didn’t actually say it. Instead, I just tried to get Leslie to leave him be. There was no point in arguing with him. All three of us knew he was lying. But Leslie kept badgering him.
“Ben, I can even show you your first real life vagina today!” She said.
Which was probably true, I thought. Leslie had no problems getting naked or flashing people – even guys. She certainly wasn’t shy about showing off and saw it all as a joke.
Then Ben started talking about how he’s seen naked girls before.
“You need to stop looking at so much porn,” I said.
He denied it. If he wasn’t so proud and being such an ass, Leslie actually probably would flash him, I thought, at the time. But when I was thinking that, she grabbed MY wrists.
“Ben! Here’s your chance! Wanna see your sister’s hoohaa?!” Leslie teased.
“Les!” I laughed. I just figured she was joking, but she was holding me tight.
“Oh Bennny! Look over here!” Leslie continued. She then slowly worked my shorts down past my hips. My underwear came into view! Ben’s face was beat red. He was just staring at his monitor, but then Leslie pulled my shorts past my butt and they dropped to my ankles. Ben looked back over and I saw his eyes run up and down my legs. Gross!
“Leslie that’s enough! Stop teasing him!”
“Ben, you wanna do the honors?” She ignored me.
Ben remained in his chair.
“LES STOP!”
“Oh, c’mon, he’s never gonna see one!” She laughed.
“Well, mine shouldn’t be the first!” I protested. I began trying to struggle to get away, but it was no use. Leslie prolly has 20 or 30 pounds on me.
“THREE!.....” She began counting.
“TWO!....” I kept trying to escape.
“ONE!” Leslie announced with glee, then pulled my underwear down to my ankles!!
OHMYGOD!!! I screamed as my you-know-what was exposed in front of Ben….and he was staring! SOOOO FRICKIN GROSS!
“STOP LOOKING, FREAK!” I snapped, taking my anger out on Ben.
“BAHAHAHAHAAHA he can’t keep his eyes off it!” Leslie was laughing hysterically. She let me go, and I quickly pulled my pants up. “You think he’s got a boner!?” She continued. I was so irritated with her, and didn’t answer. “I bet he does!”
“I do not you fucking cunt!!” Ben screamed at her with language I’d never heard him use. Wrong move.
“Let’s find out!” Leslie yelled and sprinted over to Ben. She began groping my little brother and then shouted out triumphantly. “He does! He’s hard B! He’s hard!” She continued to cackle.
I was so embarrassed and annoyed, and again, I took it out on Ben.
“You’re so gross dude, don’t you watch enough porn!? Why do you have to check out your own sister!?”
I stormed off back to my room and Leslie followed. I made her promise not to tell anyone at school about what happened. I didn’t think she’d listen, but then I told her Ben might tell on her for grabbing him and she could get in big trouble, especially since she’s 18. Really, I was just trying to spare myself the humiliation, but she bought it.
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drew
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Re: A Tangled Web
BAILEY
It was one of the first home football games of the year and our student section was dressing up as Indians because the school we were playing was The Cowboys. The weather had yet to break and I was wearing a Pocahontas dress that was, admittedly, a bit skimpy. I still had a nice tan from summer and I thought I looked really cute in the outfit. Plus, some of the outfits my friends were wearing would be WAY sluttier. Nonetheless, I made sure to avoid my mom and dad when sneaking out for the nigh. Unfortunately, I ran into my little brother. He had been super weird – even for him – since Leslie pantsed me in front of him.
“Oh…hey Ben,” I sighed when I saw him in the hallway. He looked at my outfit, and his eyes lingered. You see, this is what I’m talking about. “I’m going to the football game,” I said, shortly.
“Of course, you are,” he muttered.
“What does that mean?” I snapped.
“Nothing. But that’s what you’re wearing?” He questioned. And used his faux-disgust as an excuse to check me out even more in my outfit. I crossed my arms over my cleavage. He was creeping me out.
“Uggghhhh, it’s the game’s theme, Ben. We’re playing The Cowboys. Everyone in the student section is dressing like this.”
“Slutty sheep.”
“God, you’re annoying!” I spat. “Just tell Mom and Dad I left, okay?” I snuck out of the house quickly, as I feared my brief argument with Ben would alert my parents.
*********************
The game was a blast and as I said, some of my friends and the other girls in the student section made me look like a choir girl. Leslie’s skirt barely covered her ass cheeks and her boobs were spilling out of her top. If this was school, she would’ve been sent home in the first five minutes. She had me cracking up all night.
“Watch me get one of these sophomore kids to get us some popcorn and sodas,” she said. She then turned around to the group of boys and “accidently” dropped her phone on the ground.
“Oh shit!” she exclaimed. She bent over in front of them and 4 pairs of eyes went straight down her shirt. She looked up at them and giggled, batting her eyelashes. She flirted for about 30 seconds with them before telling them she was hungry. You’d have thought they were out there on the field with how fast they sprinted from their seats and dodged the traffic, trying to get to the concession stand. They arrived 10 minutes later with our snacks.
Later in the game, Leslie was getting tipsy. She had poured one of those small Fireball bottles into her soda and was getting loud and obnoxious. She was teasing one of our soccer teammates, Shelby, about her boyfriend.
“Brad might be the worst player on the team!” Leslie chuckled.
“Shut up, he is not! He plays a lot,” Shelby replied.
“Well yeah but he doesn’t do anything,” Leslie said. “I mean, he plays ‘catcher’ or whatever right?”
“Receiver,” one of the guys sitting next to us laughed, correcting Leslie.
“That’s it….” Leslie slurred. “Is he even gonna catch 1 touchdown this year?”
“Yeah,” Shelby said.
“Doubt it! Looks like Bailey’s boy Landon is gonna score em all!”
Landon’s our star player. He’s really fast and our team basically just gives him the ball every play. He’s also gorgeous and a grade above me. He’s in math class with Leslie and I, and has kinda been flirting with me a lot.
“Shut up, he’s not ‘my boy’,” I blushed, as I noticed some of the senior girls looking at me with jealousy after Leslie’s comment.
“Ahh you just don’t know it yet, you two are definitely boinking…probably by Homecoming,”
“Ohmygosh!” I put my hand over my face, laughing.
“But anyway, yeah Shelby, Brad fuckinnn sucks!”
“Shut up, Leslie,” Shelby said, I could tell she was getting irritated. “I bet you $50 Brad scores this year.”
“Yeah!! Stick up for your man! I love it!” One of the senior girls on our soccer team, Adira, laughed.
“Fifty bones?! Way too rich for my blood. But I’ll do ya one better…if Brad scores a touchdown this year, I’ll do a naked lap at the post-game fire,” Leslie said.
“Ooooooh!!!” The crowd buzzed with excitement.
“BUT.” She paused dramatically. “If he doesn’t….well….tit for tat little Shelby.”
It was Shelby’s turn to flush red. A lot of the guys were looking at her hungrily. Bunch of horndogs! Shelby's a cute, All-American girl. Blonde hair, bright blue eyes, a cheerleader for the basketball team in the winter. I wouldn’t say this to Leslie, but there was definitely more excitement surrounding the idea of Shelby streaking. Shelby didn’t answer right away, and was breathing a bit heavy. She looked out at the football field as the rest of the crowd began to cheer loudly.
“Scoring for The Spiders, number 30, Landon Miller!” The PA Announcer’s voice boomed over the loudspeakers at the most inopportune time for Shelby.
“Bahahaha!” Leslie cackled. “It’s alright Shelby, I didn’t expect you to agree to it anyway.” She put her hand on Shelby’s shoulder. “Everyone knows Brad’s not that dude…it’s okay!”
Adira smiled kindly, but looked at Shelby a bit disappointed, then turned around back to the game. There was a brief silence.
“Okay fine, it’s a bet!” Shelby said.
“WHHHAAAAATT!?” The student section erupted in excited chatter.
Leslie raised her eyebrows at Shelby. “Seriously?”
“Yep,” Shelby said, with not so much confidence.
Leslie raised her hand out and my two teammates shook on the deal.
Leslie and Shelby’s bet wasn’t the only excitement of the game. In the second half, out of nowhere, one of the senior volleyball players, Taylor, began screaming. “WHAT THE FUCK ARE YOU DOING PERVERTS!!” She grabbed a bottle of Coke and began dumping it under the bleachers. I looked down below and noticed a group of kids down there, wearing hoodies and masks. The scurried away like rats. Everyone began murmuring. “They were taking pictures of us!! Up our skirts!” Taylor cried out. All I can say is THANK GOD I wore spandex under my dress to the game.
************
Near the end of the game, everyone had calmed down. We were getting ready to head out when the crowd cheered again. Our team had just scored another touchdown.
“Scoring for the Spiders, number 18, Bradley Wood!”
Everyone looked back at Leslie. She just laughed, and rolled her eyes. But I’ve never seen Shelby look so relieved.
It was one of the first home football games of the year and our student section was dressing up as Indians because the school we were playing was The Cowboys. The weather had yet to break and I was wearing a Pocahontas dress that was, admittedly, a bit skimpy. I still had a nice tan from summer and I thought I looked really cute in the outfit. Plus, some of the outfits my friends were wearing would be WAY sluttier. Nonetheless, I made sure to avoid my mom and dad when sneaking out for the nigh. Unfortunately, I ran into my little brother. He had been super weird – even for him – since Leslie pantsed me in front of him.
“Oh…hey Ben,” I sighed when I saw him in the hallway. He looked at my outfit, and his eyes lingered. You see, this is what I’m talking about. “I’m going to the football game,” I said, shortly.
“Of course, you are,” he muttered.
“What does that mean?” I snapped.
“Nothing. But that’s what you’re wearing?” He questioned. And used his faux-disgust as an excuse to check me out even more in my outfit. I crossed my arms over my cleavage. He was creeping me out.
“Uggghhhh, it’s the game’s theme, Ben. We’re playing The Cowboys. Everyone in the student section is dressing like this.”
“Slutty sheep.”
“God, you’re annoying!” I spat. “Just tell Mom and Dad I left, okay?” I snuck out of the house quickly, as I feared my brief argument with Ben would alert my parents.
*********************
The game was a blast and as I said, some of my friends and the other girls in the student section made me look like a choir girl. Leslie’s skirt barely covered her ass cheeks and her boobs were spilling out of her top. If this was school, she would’ve been sent home in the first five minutes. She had me cracking up all night.
“Watch me get one of these sophomore kids to get us some popcorn and sodas,” she said. She then turned around to the group of boys and “accidently” dropped her phone on the ground.
“Oh shit!” she exclaimed. She bent over in front of them and 4 pairs of eyes went straight down her shirt. She looked up at them and giggled, batting her eyelashes. She flirted for about 30 seconds with them before telling them she was hungry. You’d have thought they were out there on the field with how fast they sprinted from their seats and dodged the traffic, trying to get to the concession stand. They arrived 10 minutes later with our snacks.
Later in the game, Leslie was getting tipsy. She had poured one of those small Fireball bottles into her soda and was getting loud and obnoxious. She was teasing one of our soccer teammates, Shelby, about her boyfriend.
“Brad might be the worst player on the team!” Leslie chuckled.
“Shut up, he is not! He plays a lot,” Shelby replied.
“Well yeah but he doesn’t do anything,” Leslie said. “I mean, he plays ‘catcher’ or whatever right?”
“Receiver,” one of the guys sitting next to us laughed, correcting Leslie.
“That’s it….” Leslie slurred. “Is he even gonna catch 1 touchdown this year?”
“Yeah,” Shelby said.
“Doubt it! Looks like Bailey’s boy Landon is gonna score em all!”
Landon’s our star player. He’s really fast and our team basically just gives him the ball every play. He’s also gorgeous and a grade above me. He’s in math class with Leslie and I, and has kinda been flirting with me a lot.
“Shut up, he’s not ‘my boy’,” I blushed, as I noticed some of the senior girls looking at me with jealousy after Leslie’s comment.
“Ahh you just don’t know it yet, you two are definitely boinking…probably by Homecoming,”
“Ohmygosh!” I put my hand over my face, laughing.
“But anyway, yeah Shelby, Brad fuckinnn sucks!”
“Shut up, Leslie,” Shelby said, I could tell she was getting irritated. “I bet you $50 Brad scores this year.”
“Yeah!! Stick up for your man! I love it!” One of the senior girls on our soccer team, Adira, laughed.
“Fifty bones?! Way too rich for my blood. But I’ll do ya one better…if Brad scores a touchdown this year, I’ll do a naked lap at the post-game fire,” Leslie said.
“Ooooooh!!!” The crowd buzzed with excitement.
“BUT.” She paused dramatically. “If he doesn’t….well….tit for tat little Shelby.”
It was Shelby’s turn to flush red. A lot of the guys were looking at her hungrily. Bunch of horndogs! Shelby's a cute, All-American girl. Blonde hair, bright blue eyes, a cheerleader for the basketball team in the winter. I wouldn’t say this to Leslie, but there was definitely more excitement surrounding the idea of Shelby streaking. Shelby didn’t answer right away, and was breathing a bit heavy. She looked out at the football field as the rest of the crowd began to cheer loudly.
“Scoring for The Spiders, number 30, Landon Miller!” The PA Announcer’s voice boomed over the loudspeakers at the most inopportune time for Shelby.
“Bahahaha!” Leslie cackled. “It’s alright Shelby, I didn’t expect you to agree to it anyway.” She put her hand on Shelby’s shoulder. “Everyone knows Brad’s not that dude…it’s okay!”
Adira smiled kindly, but looked at Shelby a bit disappointed, then turned around back to the game. There was a brief silence.
“Okay fine, it’s a bet!” Shelby said.
“WHHHAAAAATT!?” The student section erupted in excited chatter.
Leslie raised her eyebrows at Shelby. “Seriously?”
“Yep,” Shelby said, with not so much confidence.
Leslie raised her hand out and my two teammates shook on the deal.
Leslie and Shelby’s bet wasn’t the only excitement of the game. In the second half, out of nowhere, one of the senior volleyball players, Taylor, began screaming. “WHAT THE FUCK ARE YOU DOING PERVERTS!!” She grabbed a bottle of Coke and began dumping it under the bleachers. I looked down below and noticed a group of kids down there, wearing hoodies and masks. The scurried away like rats. Everyone began murmuring. “They were taking pictures of us!! Up our skirts!” Taylor cried out. All I can say is THANK GOD I wore spandex under my dress to the game.
************
Near the end of the game, everyone had calmed down. We were getting ready to head out when the crowd cheered again. Our team had just scored another touchdown.
“Scoring for the Spiders, number 18, Bradley Wood!”
Everyone looked back at Leslie. She just laughed, and rolled her eyes. But I’ve never seen Shelby look so relieved.
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mikewozere
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drew
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Re: A Tangled Web
CRAIG
Things were going well for me in my senior year. I had an easy schedule, had already finished my college applications, was getting along with everyone, and had a mega crush on a girl who seemed into me.
Drama class gave me an opportunity to put my charisma on display for Bailey. Me and my buddies were putting on hilarious skits that had everyone roaring. I admit that most the ideas were stolen from comedians or movies and shows we found funny, but hey, the class was none the wiser and it was really the delivery that sold it. I cherished seeing Bailey’s cute, dimpled laugh after I said something funny.
The two of us had started talking more. I usually tried to walk with her after class as our lockers were near each other and we were both headed to the locker rooms for practice at the end of the day.
There were a few times her weird brother Ben would be at her locker asking to get into her car or borrow some money, or whatever. I made sure to say hi to him nicely every time I saw him, even if Bailey herself was being short with him. I’ve watched enough TV to realize if you’re a dick to a girl’s family member you’re hurting your chances with her. But Ben never said hi back.
Football season was going as predicted. Our team was good but I only ever got to play in garbage time. I wasn’t a standout athlete but I enjoyed the structure of sports and hanging out with the guys. Also, being around for all the get togethers and after parties.
We always had fires at my buddy Brad’s house after Friday night home games. He had a deep backyard that bordered on the woods and there weren’t any surrounding houses. His mom was the only one in the picture and was usually at the local bars on Friday nights but even when she was around she didn’t give a shit what we did. So, we’d sit around the fire and drink and smoke and try to up our rizz (yes, I know, I hate that word too) around the hotties who would come over.
It was to my utter surprise - and delight - when one September night Bailey and her friends came strolling up to the fire. She hadn’t been in attendance before. At least, not that I can remember. It was dark out, and she was wearing a darker hoodie so I didn’t notice her at first. I was relaxed, drinking some brews, and flirting with Adira – a cute black girl in my grade, when Bailey neared the fire in a shy manner and I saw her doe eyes meet my gaze.
“Ohhh,” I blurted out, nearly spitting out my beer. I straightened in my chair and put the beer down behind me. I didn’t know how she would feel seeing me drinking, but she seemed like a "good girl" and I didn’t wanna come off like a drunk. I quickly ignored Adira, turning away from her. She had a college boyfriend anyway.
“Hi Craig,” Bailey said, quietly. She smiled. She looked gorgeous, illuminated by the flames.
“Hey Bailey,” I said. “What’s up?”
“Not much. Good game tonight!”
My face went red. I played like 5 snaps.
“Ha, yeah, he sure kept that bench nice and toasty for us!” Brad said. Fucking cock blocker. He was acting all cocky cause he had caught a touchdown pass at the end of the game. His first one ever.
“Well, you guys won!” Bailey didn’t seem to care about Brad’s comment.
“Yeah man, no W if that bench was cold,” I tried to joke awkwardly. Bailey smiled, but no one laughed.
“We dressed up as Indians for the game tonight,” she said.
“I saw that, think it’s the most I’ve ever seen in the student section with everyone dressed up.” I looked around and some of the guys and girls were still wearing their outfits, showing off some skin. Some of the girls’ skirts were really short and I was disappointed I didn’t get to see Bailey in her outfit. I bet she looked hot as shit. “How come you still don’t have your outfit on?” I asked.
“I do, just got a little chilly so I put my sweats on over it.”
“Ahhh,” was all I said, not wanting to come off desperate by asking to see it. I would later regret this.
We talked a bit more, but the conversation ran dry. I was too in-my-head, and couldn’t let things flow freely like I did when talking with Adira. Probably cause I had nothing to lose with her. Fortunately, the party spiced up before things got too awkward and silent between Bailey and I.
“So Les, there’s a rumor swirling around that you made a bet on me, and that you owe a certain payment,” Brad said.
“Haha, I don’t know what you’re talking about,” Leslie said.
Leslie was in my grade and was captain of the girls’ soccer team. She was a fun hang, and gave no fucks what people thought of her. But she could get annoying in large doses. She was neighbors with Bailey and I know the two of them had been good friends for a while so I was trying extra hard to get along well with Leslie this year.
“No, no, no you don’t!” Shelby, Brad’s girlfriend argued. “We shook on it! And why are you so excited, Brad?!”
“Woah, woah, woah, you were part of this bet?” Brad asked, ignoring the accusation.
“Yup,” Shelby replied.
I could see Brad’s booze filled brain working hard to piece things together. “…and what happened if I didn’t score a touchdown? What did you have to do?”
Shelby was a little taken aback. “Well, it doesn’t matter, cause I knew you were going to!”
“Hahaha, the same thing, Boo-Radley!” Leslie said.
Damn. I was excited to see Leslie streak, I’d already seen her tits a few times before at parties and what not – though it’s been probably over a year. But Shelby was a baddie. One of the hottest girls in school. Had I known about this bet, I would’ve been out on that field trying to trip Brad, repercussions be damned. Not like the coaches could cut my playing time for punishment.
“Aww come on Babe, why are you offering to do that? Do you want these guys seeing you?” Brad said, a little upset, and I feared we were heading for a couple’s fight.
“Peer pressure,” Shelby said simply, leading to some laughs. “Brad, relax, I KNEW you would score. You had the whole year to do it. You should be happy I stood up for you.”
Brad calmed down a little. “Okay, I am....but can you not offer to do that in the future without my permission?”
Oops.
“YOUR permission?” Shelby was irritated. “I don’t need YOUR permission for anything, Brad.”
“When it comes to things like this, yeah you do,” Brad replied, like an idiot.
“No. I don’t Brad,” Shelby said. She got up out of her chair and began walking away.
“I didn’t mean it like that! Babe, come on!”
“No, Brad! Go watch Leslie streak! You know you want to! You were soooo excited before you heard I was part of the bet!”
“BABE!”
Leslie was holding her breath with her eyes wide in a sarcastic “on eggshells” expression.
Shelby got in her car and drove away.
“Well shit, thanks a lot Les,” Brad said.
“Me? I didn’t do anything! She offered the bet!....sort of,” Leslie snickered.
“Whatever. Welp, I’m in trouble anyway so I might as well get to see you naked. Go do your streak.” Everyone laughed.
“Haha, yeahhhhh need to get this party going again after that buzzkill. Bailey, come watch my clothes for me?” Leslie said.
Bailey agreed and got up to follow her friend. The rest of us waited by the fire in anticipation.
About 3 minutes later Leslie came sprinting out of the shadows buck naked. She was covering her tits and puss with her hands.
“Hell yeah!!!” The guys cheered.
Leslie was a bigger girl but she looked hot naked. She was tall and thick but not flabby or fat. Her big ass bounced in the moonlight for our delight once she passed us. Bailey turned and smiled at me and I looked back at her, as hard as it was to ignore her streaking friend. I gave her a shrug. When I looked back toward Leslie, she had completed her lap. She was still covering her goodies.
“Hey, now…you gotta at least give us a two-handed wave before you get dressed!” Brad said. The other guys voiced their agreement.
“Yeah, we never saw anything!” someone said.
I stayed quiet, knowing Bailey was next to me.
“Ha! Fine, fuckers!” Leslie said. And with that she released both hands and gave us two middle fingers – and a full-frontal shot! Her cans were heavy with big nips, as nice as I remembered them. She shaved, and had no tan-lines – anywhere- which was cool to see. She quickly covered back up and Bailey brought her clothes back to her. She got dressed and rejoined us, as if nothing had happened.
The fire crackled on.
“What did you think about Leslie, Craig?” Bailey asked me.
“Yeah, Craig, what’d ya think?” Leslie pitched in, raising her eyebrows at me.
“Err…”
“Ha, he’s so nervous!”
“Haha, fuck off. You looked nice, Leslie. Like you keep in good shape.”
“Like you keep in good shape,” she mocked me. “Bet you’re wishing it was BAY – LEE!”
Shit. Had I been that obvious?
LES!” Bailey gasped and gave her friend a slap on the arm.
“What, I’ve seen you too chatting each other up! Listen, my goal this year is to play Cupid. Let’s get as many hookups as we can. I got one year left…same with you Craigory! So, live it up! Too many prudes in this school. And you two….would be adorable!”
Bailey and I smiled at each other. And then my fun night took a wrong turn.
A black pickup truck drove its way through Brad’s backyard and came to a halt near the fire. Everyone turned to look, already knowing who was about to step out.
Landon Miller, our star running back (and shooting guard, and center fielder), climbed out of his driver’s seat, sauntered over to the fire, and sat down on Bailey’s other side.
I like Landon. He’s a good dude, albeit a tad arrogant. He looks like he’s about 20 something years old and is jacked with tats down his left biceps. Has a constant 5 o’clock shadow. All the girls are obsessed with him and it’s hard to be confident in his presence. Unintentionally, he makes you feel like a little boy.
“Sup guys....Les, you did a naked lap?” Landon wasted no time as he held up a text message on his phone. “Lil pissed I missed that,” he grunted.
“Snooze ya lose, Lando,” Leslie replied.
“Next time,” Landon said, winking at her. His eyes wandered around the circle. “Bailey!” Landon said, noticing my crush sitting next to him. I paid close attention. “You gonna be hanging out with us degenerates this year? Bold move, we’ll take your innocence.”
“Haha,” Bailey laughed. “Yeah, Leslie convinced me….” She paused. “No streaking for me, though!” She said.
“Ah, well, that’s what they all say,” Landon said. Brad tossed him a beer. He caught it one handed and cracked it open. “You didn’t dress up as an Indian?” Landon nodded at Bailey’s sweats.
“I did!” Bailey said. Just got a little too cold for my outfit.”
“We’re by the fire. You still got it on?”
“Yeah, underneath.”
“I wanna see,” Landon said.
Bailey happily lifted her hoodie up and pulled her sweats down past the bottom of her dress. I could see the back of her nice toned thighs from my point of view. Landon gave it a look-over.
“You pull it off well, you have Native American ancestry?” Landon asked. Bailey pulled her sweats back over her costume.
“I actually do, on my Mom’s side. But it’s pretty far back, and only a little.”
“Right on, that’s cool….won’t get ya any scholarships though.”
Bailey laughed….
I don’t know why I was naïve enough to think that I was the only guy who would notice Bailey this year. Cute face, athletic body, sweet innocence – she was every main character’s crush in every teen movie ever made. For some dumbass reason I thought I was the only one to “discover” her, but it looked as if I had way more competition than anticipated. Including the most popular guy in school, who had no issue cutting right to the chase with girls.
Fuck.
Things were going well for me in my senior year. I had an easy schedule, had already finished my college applications, was getting along with everyone, and had a mega crush on a girl who seemed into me.
Drama class gave me an opportunity to put my charisma on display for Bailey. Me and my buddies were putting on hilarious skits that had everyone roaring. I admit that most the ideas were stolen from comedians or movies and shows we found funny, but hey, the class was none the wiser and it was really the delivery that sold it. I cherished seeing Bailey’s cute, dimpled laugh after I said something funny.
The two of us had started talking more. I usually tried to walk with her after class as our lockers were near each other and we were both headed to the locker rooms for practice at the end of the day.
There were a few times her weird brother Ben would be at her locker asking to get into her car or borrow some money, or whatever. I made sure to say hi to him nicely every time I saw him, even if Bailey herself was being short with him. I’ve watched enough TV to realize if you’re a dick to a girl’s family member you’re hurting your chances with her. But Ben never said hi back.
Football season was going as predicted. Our team was good but I only ever got to play in garbage time. I wasn’t a standout athlete but I enjoyed the structure of sports and hanging out with the guys. Also, being around for all the get togethers and after parties.
We always had fires at my buddy Brad’s house after Friday night home games. He had a deep backyard that bordered on the woods and there weren’t any surrounding houses. His mom was the only one in the picture and was usually at the local bars on Friday nights but even when she was around she didn’t give a shit what we did. So, we’d sit around the fire and drink and smoke and try to up our rizz (yes, I know, I hate that word too) around the hotties who would come over.
It was to my utter surprise - and delight - when one September night Bailey and her friends came strolling up to the fire. She hadn’t been in attendance before. At least, not that I can remember. It was dark out, and she was wearing a darker hoodie so I didn’t notice her at first. I was relaxed, drinking some brews, and flirting with Adira – a cute black girl in my grade, when Bailey neared the fire in a shy manner and I saw her doe eyes meet my gaze.
“Ohhh,” I blurted out, nearly spitting out my beer. I straightened in my chair and put the beer down behind me. I didn’t know how she would feel seeing me drinking, but she seemed like a "good girl" and I didn’t wanna come off like a drunk. I quickly ignored Adira, turning away from her. She had a college boyfriend anyway.
“Hi Craig,” Bailey said, quietly. She smiled. She looked gorgeous, illuminated by the flames.
“Hey Bailey,” I said. “What’s up?”
“Not much. Good game tonight!”
My face went red. I played like 5 snaps.
“Ha, yeah, he sure kept that bench nice and toasty for us!” Brad said. Fucking cock blocker. He was acting all cocky cause he had caught a touchdown pass at the end of the game. His first one ever.
“Well, you guys won!” Bailey didn’t seem to care about Brad’s comment.
“Yeah man, no W if that bench was cold,” I tried to joke awkwardly. Bailey smiled, but no one laughed.
“We dressed up as Indians for the game tonight,” she said.
“I saw that, think it’s the most I’ve ever seen in the student section with everyone dressed up.” I looked around and some of the guys and girls were still wearing their outfits, showing off some skin. Some of the girls’ skirts were really short and I was disappointed I didn’t get to see Bailey in her outfit. I bet she looked hot as shit. “How come you still don’t have your outfit on?” I asked.
“I do, just got a little chilly so I put my sweats on over it.”
“Ahhh,” was all I said, not wanting to come off desperate by asking to see it. I would later regret this.
We talked a bit more, but the conversation ran dry. I was too in-my-head, and couldn’t let things flow freely like I did when talking with Adira. Probably cause I had nothing to lose with her. Fortunately, the party spiced up before things got too awkward and silent between Bailey and I.
“So Les, there’s a rumor swirling around that you made a bet on me, and that you owe a certain payment,” Brad said.
“Haha, I don’t know what you’re talking about,” Leslie said.
Leslie was in my grade and was captain of the girls’ soccer team. She was a fun hang, and gave no fucks what people thought of her. But she could get annoying in large doses. She was neighbors with Bailey and I know the two of them had been good friends for a while so I was trying extra hard to get along well with Leslie this year.
“No, no, no you don’t!” Shelby, Brad’s girlfriend argued. “We shook on it! And why are you so excited, Brad?!”
“Woah, woah, woah, you were part of this bet?” Brad asked, ignoring the accusation.
“Yup,” Shelby replied.
I could see Brad’s booze filled brain working hard to piece things together. “…and what happened if I didn’t score a touchdown? What did you have to do?”
Shelby was a little taken aback. “Well, it doesn’t matter, cause I knew you were going to!”
“Hahaha, the same thing, Boo-Radley!” Leslie said.
Damn. I was excited to see Leslie streak, I’d already seen her tits a few times before at parties and what not – though it’s been probably over a year. But Shelby was a baddie. One of the hottest girls in school. Had I known about this bet, I would’ve been out on that field trying to trip Brad, repercussions be damned. Not like the coaches could cut my playing time for punishment.
“Aww come on Babe, why are you offering to do that? Do you want these guys seeing you?” Brad said, a little upset, and I feared we were heading for a couple’s fight.
“Peer pressure,” Shelby said simply, leading to some laughs. “Brad, relax, I KNEW you would score. You had the whole year to do it. You should be happy I stood up for you.”
Brad calmed down a little. “Okay, I am....but can you not offer to do that in the future without my permission?”
Oops.
“YOUR permission?” Shelby was irritated. “I don’t need YOUR permission for anything, Brad.”
“When it comes to things like this, yeah you do,” Brad replied, like an idiot.
“No. I don’t Brad,” Shelby said. She got up out of her chair and began walking away.
“I didn’t mean it like that! Babe, come on!”
“No, Brad! Go watch Leslie streak! You know you want to! You were soooo excited before you heard I was part of the bet!”
“BABE!”
Leslie was holding her breath with her eyes wide in a sarcastic “on eggshells” expression.
Shelby got in her car and drove away.
“Well shit, thanks a lot Les,” Brad said.
“Me? I didn’t do anything! She offered the bet!....sort of,” Leslie snickered.
“Whatever. Welp, I’m in trouble anyway so I might as well get to see you naked. Go do your streak.” Everyone laughed.
“Haha, yeahhhhh need to get this party going again after that buzzkill. Bailey, come watch my clothes for me?” Leslie said.
Bailey agreed and got up to follow her friend. The rest of us waited by the fire in anticipation.
About 3 minutes later Leslie came sprinting out of the shadows buck naked. She was covering her tits and puss with her hands.
“Hell yeah!!!” The guys cheered.
Leslie was a bigger girl but she looked hot naked. She was tall and thick but not flabby or fat. Her big ass bounced in the moonlight for our delight once she passed us. Bailey turned and smiled at me and I looked back at her, as hard as it was to ignore her streaking friend. I gave her a shrug. When I looked back toward Leslie, she had completed her lap. She was still covering her goodies.
“Hey, now…you gotta at least give us a two-handed wave before you get dressed!” Brad said. The other guys voiced their agreement.
“Yeah, we never saw anything!” someone said.
I stayed quiet, knowing Bailey was next to me.
“Ha! Fine, fuckers!” Leslie said. And with that she released both hands and gave us two middle fingers – and a full-frontal shot! Her cans were heavy with big nips, as nice as I remembered them. She shaved, and had no tan-lines – anywhere- which was cool to see. She quickly covered back up and Bailey brought her clothes back to her. She got dressed and rejoined us, as if nothing had happened.
The fire crackled on.
“What did you think about Leslie, Craig?” Bailey asked me.
“Yeah, Craig, what’d ya think?” Leslie pitched in, raising her eyebrows at me.
“Err…”
“Ha, he’s so nervous!”
“Haha, fuck off. You looked nice, Leslie. Like you keep in good shape.”
“Like you keep in good shape,” she mocked me. “Bet you’re wishing it was BAY – LEE!”
Shit. Had I been that obvious?
LES!” Bailey gasped and gave her friend a slap on the arm.
“What, I’ve seen you too chatting each other up! Listen, my goal this year is to play Cupid. Let’s get as many hookups as we can. I got one year left…same with you Craigory! So, live it up! Too many prudes in this school. And you two….would be adorable!”
Bailey and I smiled at each other. And then my fun night took a wrong turn.
A black pickup truck drove its way through Brad’s backyard and came to a halt near the fire. Everyone turned to look, already knowing who was about to step out.
Landon Miller, our star running back (and shooting guard, and center fielder), climbed out of his driver’s seat, sauntered over to the fire, and sat down on Bailey’s other side.
I like Landon. He’s a good dude, albeit a tad arrogant. He looks like he’s about 20 something years old and is jacked with tats down his left biceps. Has a constant 5 o’clock shadow. All the girls are obsessed with him and it’s hard to be confident in his presence. Unintentionally, he makes you feel like a little boy.
“Sup guys....Les, you did a naked lap?” Landon wasted no time as he held up a text message on his phone. “Lil pissed I missed that,” he grunted.
“Snooze ya lose, Lando,” Leslie replied.
“Next time,” Landon said, winking at her. His eyes wandered around the circle. “Bailey!” Landon said, noticing my crush sitting next to him. I paid close attention. “You gonna be hanging out with us degenerates this year? Bold move, we’ll take your innocence.”
“Haha,” Bailey laughed. “Yeah, Leslie convinced me….” She paused. “No streaking for me, though!” She said.
“Ah, well, that’s what they all say,” Landon said. Brad tossed him a beer. He caught it one handed and cracked it open. “You didn’t dress up as an Indian?” Landon nodded at Bailey’s sweats.
“I did!” Bailey said. Just got a little too cold for my outfit.”
“We’re by the fire. You still got it on?”
“Yeah, underneath.”
“I wanna see,” Landon said.
Bailey happily lifted her hoodie up and pulled her sweats down past the bottom of her dress. I could see the back of her nice toned thighs from my point of view. Landon gave it a look-over.
“You pull it off well, you have Native American ancestry?” Landon asked. Bailey pulled her sweats back over her costume.
“I actually do, on my Mom’s side. But it’s pretty far back, and only a little.”
“Right on, that’s cool….won’t get ya any scholarships though.”
Bailey laughed….
I don’t know why I was naïve enough to think that I was the only guy who would notice Bailey this year. Cute face, athletic body, sweet innocence – she was every main character’s crush in every teen movie ever made. For some dumbass reason I thought I was the only one to “discover” her, but it looked as if I had way more competition than anticipated. Including the most popular guy in school, who had no issue cutting right to the chase with girls.
Fuck.
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mikewozere
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