That’s what the fellas call me. I have a rare sexual specialty: I anally penetrate almost any girl I fancy. I’m a Greek bandit. Let me tell you how I got that way. My real name is John Benderson. In high school they called me Bend-her-over, ironically. I had never been with a woman that way, as everyone knows. That was their clever way of drawing attention to the fact. Get it? I was of middling popularity, but ran with a cool crowd, guys and girls. They were more stoners than jocks and cheerleaders. They were also above average in looks, and socially at ease, unlike me. They liked that my family had money, nice cars, and a big house. Especially they liked our in-ground pool, where we partied during my parents’ frequent vacations. The group didn’t respect me, for many reasons and particularly because my life was a romantic desert . Hence the ironic nickname.
While they paired off two by two (sometimes in my pool), I was always the odd man out. Partly, this was due to my not-so-secret shortcoming: my penis is undersized. 3 3/4 inches long when erect, and noticeably thin. The guys knew from gym class, and everyone remembered that time in junior high when Mike Stanton pantsed me, undies and all, when we were playing soccer in the field by our school during an off-period. Can’t say it was cause and effect, as I might have had the same personality with a monster cock. In any case, by senior year I had no experience, and it was hard to get experience without having experience. The rich get richer, and all that. Lust was in my heart, like any red-blooded young man. I wasn’t an ascetic. My buddy Jeff’s on-again, off-again girlfriend Christine featured prominently in my fantasies. (At least two times a day, if you must know)
She was tall for a girl, 5’7″. Blonde, with small tits and a tight ass. Slender all the way through, and built like a model. Which I don’t usually care for, but her face approached the ideal of feminine beauty. She was shy and quiet, in contrast to her reputation, which was as colorful as any in the school. Her apparent modesty made you forget how many guys had been there. Of my three best friends, Jeff, Martin, and Adam, she had done two: Jeff and Adam. I assumed Martin was just a matter of time, though he was a bore and overweight. Didn’t stop him from getting laid, unlike me. Jeff didn’t mind what Christine got up to during their frequent breaks. She wasn’t important to him, except as a fallback lay. I resented this, in my naively chivalrous way.
I also resented Jeff’s reputation as a cocksman. I knew first-hand his equipment was impressive. He had also verifiably banged a dozen of the top beauties at school, and not just the easy ones. Adam, on the other hand, I knew to be of modest size. He compensated by being disarmingly handsome and a sneakthief. He was always poaching girls from other guys. He did my sister on a regular basis; not because she was hot but because she was around. I despised him more for having got into Christine. She was becoming an obsession for me. I hated the fact that two of my friends had her, and that I hadn’t had anyone. Then suddenly my fortune changed. One of those dumb, ephemeral pussy-chasing summer teen movies became a phenomenon.
Everyone was talking about The Wrong End, a particularly raunchy specimen of the genre. The premise was that a group of girls go to comedic lengths to lose their anal cherries. I’m surprised law enforcement let our little town theater run it. Jeff convinced me, Adam, and Martin to go with him. He brought Christine along, with whom he was on-again. After one hour and thirty-seven minutes of mind-numbing stupidity and gratuitous T&A, we strolled through the parking lot toward our cars and got to talking.
“Remember when Flip cupped that girl’s tit from behind, and she kneed him in the sack? That was awesome,” said Jeff.
I added, “I thought the whole thing was a waste of time. How many girls actually want that?”
“Yeah, what are they, homos?” asked Martin.
“It’s not gay if a guy is doing it to them, dumbass,” said Adam.
“Only gay guys like to get reamed.”
“Oh, shut up. Chicks do it. You know they do.”
“Maybe the skanks you sleep with. Not normal girls.” Adam turned to Christine, who had been silent the whole day. “Is that true, Chris? Have you done it? Would you?”
“Not with me,” Jeff interjected before Christine could answer.
“Nobody would with you. You’d split them in two,” joked Martin.
We all laughed.
After a pause Christine finally spoke up. “I never have. My friends talk about it, though. More lately.”
The influence of trash culture, putting ideas in impressionable minds. I might have denigrated it at the time, but I was soon to benefit. Little did I know, there was an epidemic of dirty talk among our crowd in the wake of this ass-flick. Girls didn’t want to admit it, but they were curious. They didn’t want to miss out on what they guessed their friends might be enjoying behind closed doors. Keeping up with the Joneses for a brief period started to mean losing your anal cherry as fast as possible. As I was soon to discover. Jeff asked me to come to his place one Saturday in a series of texts. He had something to talk about, which was unlike him. Unlike all of us, in fact. We never talked about anything serious. I got there around 6. His parents were in the living room watching their flat screen. They told me he was in the basement. I found him playing Grand Theft Auto. He paused the game.
“Dude, Christine is out of control.”
“What does that mean?”
“I don’t want anyone to hear this.” He looked up the stairs, making . Sure the door was closed. “It’s that movie. Got her hot. She says Sandy and Becca and Dara have all let their boyfriends, you know, do them that way. She wants to. She’s so ready, but doesn’t think she can do it with me.”
“This is what you brought me over to talk about? I don’t think I even want to hear.”
“Don’t be a prude. Virgins are always prudes.”
“Dude, for the last time, I’ve done stuff, just not all the way…”
“Stuff, yeah. With your sister…Anyway, it’s not about that. I have to ask you a favor.” It didn’t immediately occur to me what he was after. “I want to get this out of her system, but I can’t trust just anybody. That asshole Adam has probably already started in on her. I want to go away to school this fall not tied down, knowing Christine is waiting for me when I need her. Not waiting in Adam’s lineup. You gotta help me, dude.”
“How? Adam’s gonna do what he’s gonna do. I can’t stop him.”
I was sitting on his couch uncomfortably. I didn’t like getting caught up in these cool kid in fights. They always made me feel like an outsider looking in.
“Look, we know you have a, you know…” I didn’t know. God, I was naive. “…” I added
He took a bit to build up to it. “You’re not the biggest guy.” It hit me. I was less nervous than I might have expected. I was excited, actually; turned on. Jeff wasn’t in the room for me anymore. I could only sense the absent Christine. “If you did her, she could get it out of her system, and you could finally get some.”
We didn’t talk for a bit. I was thinking of her tight butt. Eventually, I responded. “Like she would go for that.”
“She’s already on board, dude. I didn’t want to tell you until it was set up.”
“What…how could she even…she doesn’t like me that way.”
“She thinks you’re cute, man, she told me so. And it isn’t even like she wants this to be a thing. She just wants to do it to get it over with. Come on.”
“How would this work, anyway?”
“Let me take care of everything. All you have to do is show up.”
I drove home soon after. My mind ran at the speed of light. Christine, my obsession. The demure slut. She could be mine, however briefly. Mine to do what? Jeff didn’t specify. Would it be restricted to the wrong end, or would we do everything? I wasn’t sure. One sure thing: what was formerly my biggest shortcoming was now my greatest strength. My little dick was the key to unlock the gateway to my fantasy girl. Soon it would unlock other gates, as well.
Soon Johnny Buttfuck would be born.
I went online immediately upon arriving home, seeking to learn everything I could about anal sex. There was a lot of information out there, as you can imagine. I also wanted to learn everything I could about Christine, so I went on her Facebook page. Maybe I could find a gift for our night together. Not a dozen roses, but something to put her at ease. Jeff said he’d take care of everything; I just had to show up. Which was both a load off and a load on my mind. With a sure thing in my future I was left with nothing to do but ponder the unknown. What will it be like? How should I act? What will she allow me to do? Are we even going to kiss? Will I be any good ? Will she respond to me? Will she laugh at me? How much will she tell Jeff? A thousand scenarios ran through my head, then a thousand more. But I’d just have to wait. Wait I did: six days’ worth.
My bratty, older sister bothered me about Adam daily. Not overtly, but via hinting questions. I barely saw the other guys, but I did see Adam talk up Christine from a distance at the mall. I was there to buy Christine a bottle of Moscato, her favorite wine. Was wine too presumptuous? What was I asking? I already knew how our night together would end, if it ever arrived. I had half a mind to tell Adam my sister was still hot for him. Not that I saw why he’d care. She’s overweight with acne, not ugly or a nerd but not worth pursuing by his kind, I thought. I spied on her one afternoon not long ago changing in the cabana; couldn’t help myself. She has big tits and a backside, but not much else.
I like her, despite her brattiness; we used to be close. Less so since she started seeing boys, and especially since she started banging Adam. One time, I heard them through the upstairs window while I was in the pool. My sister is loud, and apparently Adam knows what he’s doing. Fearing that he’d spoil my plans by being on Christine’s trail, I figured I should toss down my sister as a red herring. So I did. I texted Adam from her phone asking for a booty call. He showed up at our house a couple of hours later, looking for her. I told him she was up in her room.
Adam barely said, “Thanks, Bend-Her-Over,” then blew past me.
I waited outside her door for a minute or so, then heard familiar sounds. My skullduggery had worked. Pervy or not, I was suddenly seized with the acute desire to watch Adam go at it with my sister. This was practical education, I told myself. I had never seen live sex. I should gather data for my night with Christine. I had already gone further than I thought my previously firm morals would allow me with this Wrong End stuff; might as well go all the way, beyond good and evil. The door was open a crack. I leaned on it, easing it forward, careful not to squeak. There was Adam’s ass pounding rhythmically in a standing position, my sister splayed on her back on the bed.
“Ooh, ooh, ooh,” she whimpered in a high pitch.
He wasn’t making a sound. I could swear I heard squishy noises. He pulled out and put his cock next to her mouth, and she greedily accepted. I saw him erect for the first time. (I caught glimpses of him nude in the locker room before, but never in full tumescence.) He was long and girthy. Not as big as Jeff, no doubt, but respectable. That thing had been in Christine, I thought, as would my little thing soon be. Speaking of which, I was hard as iron and sticking straight up. I felt guilty, because I could see my big sister’s wet, brunette bush and my buddy’s cock. So I slipped back out. Two days to paradise, and Adam seemingly out-of-the-way. Jeff emailed me details that night, and I poured over them.
It was fairly simple: Christine would show up at my place. My parents were absent, as usual, and I could ensure my sister would be gone. (Maybe over at Adam’s getting plowed.) Christine would take it from there. I was told she knew what to do, but I bought all the necessary paraphernalia, just in case. The night of nights arrived. I spent all day a nervous wreck. My sister had indeed gone out to meet Adam, on a date to see that movie, of all things. Hopefully she didn’t get any ideas. I set the mood in my parents’ room, with music, lighting, and refreshments.
Christine arrived on the dot. Oh, my God. The doorbell rang, I answered, and she stumbled in. Already a wee bit tipsy, wearing nothing special: a faded t and jeans with flat shoes. Probably no bra; she didn’t need one. She wasn’t made up and her hair looked greasy, but to me she was a vision of loveliness.
“Jeff told you all about it, I’m sure,” she said softly. I had to learn in to hear. She smelled like strawberry bodywash. “He loves me, but this isn’t something he can do for me. I hope this isn’t too weird. We’re friends and we can stay friends, this doesn’t have to be a big thing, it’s just sex, you know? Am I talking too much?”
She was rambling a bit. I was afraid to say anything. “I thought we’d go upstairs,” I said, and motioned in that direction.
“Sarah’s not here, is she?” Referring to my sister.
“No, just us.”
When we got to the room she seemed surprised by the layout. I offered her a glass of wine.
“Better not. I already had some.” I could tell. She went over to the iPod dock. “I love this song.”
Instantly she backed into me and started dancing. Her ass–soon to be my ass–rubbed against my crotch. I was hard already; she must have felt it, small or not. As she danced she shed her clothes. This was happening fast. She had milky-white skin. Yup, no bra. Her breasts were tiny, almost flat, with puffy pink nipples.
When she was down to her turquoise panties she asked, “Are you going to catch up?”
I disrobed moderately fast. Didn’t like the idea of getting to the end. In my tighty-whities I reached the moment of truth. I knew she hadn’t been present the day of my infamous pantsing. I hooked my thumbs into my waistband, and pulled down. She smiled without laughing. My tiny penis, all upright and angry-like, was what she expected. I walked up to kiss her, but as I got close she backed off.
“No extracurricular’s, mister.”
Was that a rule between her and Jeff, or was it me? I didn’t know. But I knew it meant no blow job, no pussy licking, no intercourse. I was to keep my vaginal virginity. She prepared herself on the bed as I watched from a distance. Aside from the grinding, this night was turning out clinical. She called me over and applied a condom. A girl was touching my thing! She asked me if I knew what to do, and we talked about it briefly. Then she got on all fours near the edge of the bed. I positioned my hard, little dickie near her entrance. Her slender behind was raised in anticipation.
I grabbed Christine by her narrow hips. Even for a girl her size I had to get close to penetrate. She wasn’t making any noise, and her body was tensed up. I felt distant, mounting her from behind like this, with no communication between us. I wished I could see her face. My parents’ floor-length mirror (Lord knows what they did with that) wasn’t angled properly. She made no sound or movement as my tip pressed against her ring. I fumbled around to find that, but once I touched upon it I thrust forth.
“Oh, ah, ooh, slowly, slowly,” she said.
My size was enough to be uncomfortable for her, at first. Once I popped her ring, the resistance and her discomfort dissipated. I felt the strangest sensation. Since I’d never been inside a woman before I had nothing to which to compare it, but it wasn’t what I expected. There was pressure from the ring, then nothing. Like a void. The void was enough. Despite my foresight in jacking off beforehand, I felt a familiar bubbling deep within. I was going to cum already. One more shortcoming to show off to Christine, who was starting to respond somewhat.
Rocking back and forth slightly, she moaned, barely audibly, “Mmmm.”
That was enough. I popped in the condom, just before I managed to let out, “I’m gonna cum.”
“Oh, that’s okay,” she said, reassuringly.
I didn’t know whether she was patronizing me. Didn’t much matter. She wasn’t expecting a stud, I rationalized. She was here to lose her anal virginity, and had. Nevertheless, I felt embarrassed, and apologized.
“Sorry, you’re just so hot.”
“That’s okay, that’s okay,” she said softly.
We laid together for a spell. I smelled her body wash again. My little dick stayed hard the whole time. She didn’t comment on that. Then she spoke, “Jeff’ll be happy we got this out-of-the-way. He’s been pushing me. I didn’t want to at first, but he said it’d be good for me to get what everyone else is getting.”
So it wasn’t her idea after all. That’s explains why she’s been distant all night, I thought, and why she showed up tipsy. Jeff is a bastard, roping in his safe buddy to buttfuck his hesitant girlfriend. I felt guilty for being a part of it.
“I did like it, though. Maybe we can do it again, if Jeff says okay. You were gentle. When Jeff tried it hurt so bad. He said you’d be good to break me in, but I don’t think anything can prepare me for him.”
Double bastard. This was all about Jeff. He wanted me to break her in so his big, fat cock could get off with his skinny girlfriend’s tight ass. Girlfriend? More like fuck buddy, although she didn’t see it that way.
“Aren’t you gonna say anything? What did you think?”
I considered my words carefully. “I think you’re perfect, a goddess, and I’m lucky to have been with you.”
“Aw, you’re sweet.”
She kissed me full on the lips, with suction, and got up. That was a surprise. She went straight for my parents’ bathroom and turned on the shower, leaving me swimming. My dick stayed hard. I was lost in thought. She reemerged nude, a long, thin body walking toward her pile of clothes across the room. I watched her dress in silence.
“Thanks. Jeff said he’d text you later. I’ll tell him all about it. Bye.”
“Bye,” was all could say.
Just like that, she was gone. I was left to clean up. Then I went into the bathroom, her smell still in the air. I showered, still lost in thought. I can’t recount what went through my head, there was so much. When I got out I went to the sink to grab my toothbrush, still dripping. “Nice,” said a voice to my side. I had left the door ajar.
“So my brother has a baby dick,” said Sarah, my sister, back from her date with my friend Adam.
I put my hand over my crotch, too late. “I thought they called you ‘Bend-her-over.’ Guess that’s B.S.”
“Shut up,” I snapped, slamming the door shut.
Shit. Now she knew. Does the whole world need to know about my shortcoming? Next morning my parents showed up. Sarah intimated she knew about my tryst the night before. Veiled comments, sky insinuations She even brought up Christine’s name at breakfast. Did Adam know? Had he told her? I wouldn’t have put it past Jeff to brag to Adam about breaking in the ass of the slut they shared. I waited until we were alone to confront Sarah.
“What’s up with you?”
“What do you mean, little bro?”
“You’ve been dropping hints like anvils.”
“Hints? ‘Bout what? You have something to hide? Besides washing your baby dick in mom and dad’s bathroom, I mean ”
Grrr. Did she have to talk like that? “I mean more than that. About Christine and all.”
“You saw that movie The Wrong End, too, right?”
“Adam said it put some ideas in your friends’ heads.”
Jeff had told Adam. Triple bastard! “Whaddyou know about it?”
“I know you watched Adam and I fuck the other day. I know you were meant to put your baby dick in the Ice Princess last night. That’s why I agreed to leave the house. The last thing I want to walk in on is you and that skinny bitch.” I was dumbfounded. “Adam told me you only got to fuck her because you’re under-endowed, but I had no idea.” Again with the insults. For a psych major at college she sure lacked compassion and risked giving me a complex. “He said she was like doing a dead fish.”
“I don’t know why Adam bothers with a girl like you when he can lay Christine. Don’t you have losers at school lining up to do you?” I said.
I feared I may have gone too far with that comment, but I had to defend Christine. “Yes, but I’m not at school. Tell me, how was the Ice Princess? I couldn’t see, did she give your baby dick frostbite?”
My sister was deadly jealous. I guessed she was afraid that Adam would abandon her for a nod from the Ice Princess. “Nevermind, Sarah. Don’t say anything to mom or dad, or I’ll tell them you’re screwing my high school friend.”
We parted on that note. My texts back and forth with Jeff didn’t lead anywhere. I didn’t want to confront him about what I had learned, and he got the full story from Christine. My mind that morning was on moving past the whole charade. I wanted nothing to do with the lot of them, frankly. Except Christine, but it would be impossible for me to pull her from the sex triangle, square, or whatever they’d built around themselves. Then my life took another turn, and I inched farther in my ascension toward Johnny Buttfuck status. Jeff got back in touch. Another girl he had fucked last year, Heather, was bit by the Wrong End bug. For real, this time. Jeff said Heather had reached out to him, but obviously he wasn’t in a position to pop her cherry. He asked me if I was up for it. The gall! He probably wanted to swoop in and do her afterwards, too. I was his warm-up act. Heather, you must know, we nicknamed ‘pornstar’.
She had melon-sized tits on a small frame, big 80s hair, thick make-up, and an ass like a coffee table. You could set your drink on it. Even if I wanted to do her, which of course I did, I don’t know if my guy would make it past her cheeks. Jeff was gung-ho about it, however. Next day he texted me that Christine and he had told Heather about me. Christine agreed to the set-up? No doubt she was ignorant of Jeff’s larger plans. It gave me a boost, I must admit, that the girl I had been obsessing over recommended me to the Pornstar. I must have done okay. To think, days ago I was sexless. Now I had the chance for not only more anal cherry popping, but possibly full-on sex as well. I agreed to have Jeff set me up with Heather.
She was waiting for me at the mall food court three days later. I spent three hours getting ready. When I showed, she was nowhere to be found. Twenty minutes and two Orange Julius’s later, she showed. Wow. Halter top, epic cleavage, cut-off jeans, visible butt cheeks. Her bare legs were shapely; everything about her was shapelier than Christine. Heather wasn’t nearly as pretty, but who is? She approached my table, and my heart was in my throat. I felt scared yet powerful. Because here was this girl, come to see me of all people. Coming right at me, on purpose. I stood up, acknowledging her presence, smiling.
“Hey, Heather, nice to see you. How’s your summer?”
“I dunno, okay. I’m working, saving up,” she said.
“Yeah, at the diner? I think I saw you there once.”
“Waitressing sucks, but my tips are great. Specially from the dads.”
She winked. This girl was forward. I chuckled uncertainly. “Saving up to go to state?”
“Yup, headed there like everyone else. Cept you. I bet your parents probly sending you to the same place as your sister.”
“You know Sarah?”
“Yeah, we have…stuff in common.”
Of course. Heather was one of Adam’s conquests. I wouldn’t say they dated. Did all the girls Adam fucked know each other? “You mean Adam?” I came right out with it.
“Haha, yeah. That a-hole was seeing us at the same time over Christmas break. She stopped in and talked to me about it at the diner once.”
This conversation was getting off topic. Why were females suddenly so open to me about their sex lives? The movie, that’s why. After an awkward pause, she continued.
“Jeff tells me you have a rare talent.”
She smirked devilishly.
“I don’t know if you’d call it that.”
“I want to cut this short. You know what I’m after. How about we go back to my house and you show me that little thing of yours?” I didn’t have a response. “I want to be like Shirley with that guy Pinky in Wrong End. Know the scene where he whips it out, no foreplay? It was like, bam!”
I knew the scene. I was coming around on that movie. She shifted in her chair, and her neckline shifted to the side. I saw a whole lot of sideboob. She didn’t have to say anything else. Bend-Her-Over, soon to be Johnny Buttfuck, was about to bag another one.
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