Begging For It (Part 1)
anonymous
September 2 2012, 03:42:49 UTC
Jeff got into bed with Annie feeling a bit relieved. True, today’s study group adventure got him in huge trouble, and got him more than a few lectures about his selfishness - from his friends and his four-month long girlfriend. But as usual, a last minute save and a Winger speech saved the day and bailed him out - plus Annie was still sleeping over instead of going home. So she couldn’t be too mad at him anymore.
And when she pulled off the covers and reached into his pajama pants, Jeff truly felt off the hook.
“Ah, perfect reward for a day well saved,” Jeff bragged. That might have been too much bragging, given how badly the day started thanks to Jeff. Yet Annie wasn’t pulling away. In fact, she stroked him for a few more minutes, although she barely looked at him.
Jeff would insist on eye contact if she was sucking him off, but he could let it go for this. Actually, he would let go regardless in a few more minutes. Or he would have if Annie didn’t pull her hand back from him.
Jeff figured she was getting ready for the next step, but she didn’t remove any clothing - on her or him. In fact, she went back to her side of the bed and started reading, of all things. “Um, Annie, you kind of skipped a few steps over here,” Jeff reminded. “Do you mind?”
“I will. As soon as you beg for it,” Annie blandly said.
“Come again? I thought I heard crazy talk, but that’s not your style anymore,” Jeff commented.
“It’s clear in English too. If you want to climax, you have to beg for it. Otherwise I won’t do it. And if you try to do it yourself, then no sex of any kind for a week,” Annie informed. Now instead of trying not to cum, Jeff was trying not to laugh - and was barely succeeding.
“Annie, I already know you’re funny. There’s no need for that kind of comedy hail mary!” Jeff chuckled. “Fine, if you’re still mad at me for some reason, I’ll just finish somewhere else and call it a night.”
“No!” Annie commanded. “Jeff, you’ve got to learn your lesson! And after four months in here, I know sex is the best way to get through to you. Or a lack of sex.”
“Annie, I just did what I always do. I do something stupid, you all yell at me, I redeem myself and barely have to apologize, then rinse and repeat next week. Why make a big comedy show of punishing me now?” Jeff inquired.
“Because we’re leaving Greendale soon, and that formula won’t work in the real world! It might have worked when you were a lawyer last time, but times are different now! You’re different now! If you’re going to do this crap anyway, you have to learn there are consequences. Like having to beg and embarrass yourself before the next time you get off,” Annie informed. “So are you going to learn your lesson early or not?”
“I think I’m going to sleep. I’m sure I can study my lessons in dream world. Good night,” Jeff huffed, turning his back to Annie and shutting his eyes.
Unfortunately, his back was still exposed to Annie, who took advantage by rubbing it and kissing his neck. Jeff then rolled on his other side to face Annie, but still closed his eyes and folded his arms. Yet this left his pants perfectly vulnerable as she reached into them again. Jeff thought of rolling back, but a few good tugs by Annie kept him still.
Jeff’s next idea was to stay quiet, so Annie wouldn’t know when he was on the brink until it was too late. But Annie just had to glide her finger up and down his shaft - and she just had to palm his balls like that too. God, why did he teach her that trick? Because he wanted her to make him cum hard, of course - and she pulled her hand away again before that could happen.
Begging For It (Part 2)
anonymous
September 2 2012, 03:43:23 UTC
“Annie, come on, this doesn’t work as a running gag,” Jeff insisted.
“It isn’t a gag. Beg me to make you cum or you don’t get to. You do it yourself or leave this bed, then no sex for a week,” Annie repeated.
“Damn it Annie, you know Jeff Winger doesn’t beg in bed! He causes begging, he doesn’t do it, and you know that all too well!” Jeff recalled, then got another idea. “And you know it. That’s why you won’t follow through. You can’t survive sex without me for that long, so this is just an empty threat! As empty as my balls will be in a few minutes, so hah!”
“I survived sex without you for three years,” Annie reminded. “Even after getting it, I know I can still last without it if I have to. I don’t know about you, though.” Before Jeff could insist otherwise or demean her plan again, she pulled the front of his pants down and sucked him off - for only seven seconds before she tucked him back in.
“Okay, now this really isn’t funny!” Jeff yelled, his newfound frustration building. “Fine, if I can’t leave the room, I’ll sleep on the floor!” He went to do just that, but the minute he laid down, Annie laid on top of him and grinded down on him as deeply as possible. As angry as he was getting, Jeff just couldn’t get Annie off him when she did that.
So he played dirty by grinding back, hoping to get Annie off and make her forget about not getting him off. Yet that failed too, as Annie got up and jumped back on the bed before Jeff could stop her. But with her up on the bed and Jeff still on the floor, he might be able to tug himself a few times - and it might be enough after that grind.
However, Annie came back and caught him right as he put his hand in his pants. “That’s a week and a half of no sex if you go further, Jeff!”
“Oh, come on, seriously?!” Jeff growled.
“That’s growling, not begging. You’re getting warmer, though,” Annie all but teased.
“Damn it, fine! I’ll just wait until you go to sleep, you can’t stop me then!” Jeff gloated.
“Really, Jeff? Me going to sleep before you? Especially when I have all these great books to reread? You must be too worked up to think straight,” Annie certainly teased that time. With that, she grabbed her Greendale backpack from the floor and took out one of her books to read - while keeping an eye on Jeff every few seconds.
Jeff groaned and went back to bed, his back turned to Annie again. But after only a minute - not long enough for Jeff’s hard on to go away - Annie put down the book and reached over to pinch his ass. This made Jeff get up again, but Annie was too quick and actually pulled down his pants.
In his shock, he couldn’t stop Annie from getting his cock and sucking him off again - for longer than seven seconds. As much as Jeff wanted to fight it, that mouth was too strong. So were those eyes when they looked up at him extra wide, and so was that cleavage when Annie pushed it up. That head then bobbed extra hard and fast on him, which almost made Jeff’s knees buckle.
Jeff again tried to keep quiet so he wouldn’t tip Annie off. But that became impossible when Annie’s tongue used that special trick on his tip. Why the fuck did he teach the super student of Greendale things?!
And how the fuck could she pop off his cock and go back to bed without sucking him dry?! Did she forget whose cock this was?! But with the way she brought him to the brink and left him hanging, he almost forgot too.
Jeff grabbed himself out of desperation, but Annie then decreed, “Two weeks, Jeff!” and made him stomp his feet like a child. Annie chuckled at the irony and went back to reading, then noticed Jeff trying to reach the bathroom and corrected, “Three weeks!”
“Come on, can’t I pee this out?!” Jeff spat out.
“Not unless you leave the door open. If you don’t, it’s three and a half weeks,” Annie shut him down. Now Jeff was losing it like he was on monkey gas. He stomped around, almost reached for himself again before stopping himself, and kept groaning from the buildup in his balls.
“Annie, you’re starting to kill me here! Please - I mean, uh, just finish me off!” he backtracked.
Begging For It (Part 3)
anonymous
September 2 2012, 03:44:48 UTC
“Well, you started to say please that time. So I suppose…” Annie left hanging until she climbed onto Jeff’s lap and inserted him into her.
Jeff threw his head back and groaned in relief, especially when Annie started riding him. He was so blissed out and ready to go, he kept his hands to his side and didn’t try to embrace Annie. And by the time he was coherent enough to try, Annie climbed off him and rolled over to Jeff’s side of the bed.
“SON OF A BITCH!!” Jeff cried out at this latest blow - or lack there of. “Annie, I swear to God I’ll, I’ll….” But he was too horny and backed up to think of any good threats. None would be good enough to top this torture anyway.
“You know, since you won’t beg and take care of things, I guess I should take care of myself,” Annie offered, before placing her hand on her wet opening. As she inserted a finger and made it wetter, Jeff groaned some more and reached for her. But he stopped himself and growled again, not knowing what he was allowed to do - and not willing to risk four weeks or another way too short fuck.
Jeff tried to at least ignore Annie touching herself. But he couldn’t ignore her moans, even when he covered his ears. He couldn’t ignore her when she kept moving around to stay in his sight. And when she pulled her wet finger out of her pussy, trailed it up and down his cock and then sucked it dry, it was close to a breaking point.
“God! You dirty, precocious…..gah!! I just want to cum already!” Jeff yelled, lying on his stomach and banging his fists against the mattress.
“Well, that’s a good start,” Annie said while inserting her finger all the way inside her. Out of sheer madness at this point, Jeff resorted to humping the mattress - until Annie announced, “And that’s a month, Jeff, congratulations.”
Now utterly broken, Jeff practically screamed into the mattress and them slumped in defeat. “Okay, okay….” he finally muttered, then lifted his head up. “Annie….please let me cum.”
“Not quite, but you’re getting there,” Annie noted. Jeff didn’t even have any energy to nitpick anymore.
“Please, please let me cum. Get me off however you want, I don’t care! I’m at your mercy, just let me have my release! Please, please, please,” Jeff tried again.
“Closer….in more ways than one,” Annie answered while getting herself off deeper. And now that there was a race against time, Jeff finally didn’t care how he got it right.
“Okay, I’m begging now! I’m begging you to get me off, happy?!” Jeff spat, but instantly knew he’d have to sound less angry. “I need you to make me cum, I’m begging you….and I’m sorry. Don’t make my dick suffer because I’m such a dick, please!”
He saw he was on the right track when Annie’s face softened, so he finished with, “I know you feel like you haven’t changed me at all when I do this crap! But you have, you fucking have! I would have just left anyone else by now, both tonight and for good! But you’re still here, and I want you here, and I want you to get me off….because no one can get me off like you! I don’t want anyone else to! Please, I’m begging you to prove it one more time….”
This was by far Jeff’s most emotional Winger speech of the day. Something told him it wasn’t completely because he needed release. But he just tried to focus on Annie’s face and how it reacted, instead of watching her finger. When he couldn’t take the waiting, he laid on his back and sunk into sexual misery again.
That is, until he felt Annie climb on top of him and sink onto him again. Yet even that didn’t relieve Jeff, since she’d probably just climb off in no time. Yet when she kissed him, squeezed her thighs on him, and didn’t move when his arms went around her, it hit him that it actually worked.
And when Annie broke and whispered, “You can cum for me now,” something else hit Jeff.
Begging For It (Part 4)
anonymous
September 2 2012, 03:45:16 UTC
Normally, he would still try to hold off until Annie came, but enough was enough. Yet midway through the most powerful orgasm in recent memory, Annie released herself and made him go off even harder. They both groaned at the top of their lungs and rode their long overdue relief out together, even after fighting all this time.
By the time it was finally over and Jeff was utterly drained of everything, he found himself admitting, “Maybe I should beg more often.” This also let him realize, “I guess it’s not a punishment anymore, then. You’ll need another way to teach me a lesson in here.”
“I’ll think of one,” Annie muttered, somehow sleepier than Jeff was.
“You would, wouldn’t you?” Jeff let wash over him. Annie was diabolical like that - 80s cartoon supervillain diabolical, even. This seemingly sweet young lady was probably the most sadistic, vengeful person he knew when she was crossed. She was torturous, she was an evil genius, she was….a woman after his own cold heart.
Only she made it less cold and more gooey when she wasn’t being evil. Like when she just laid on top of him and gave him warm feelings he’d never had in bed before - even after losing this epic game of sexual wits. Even with the loss, he didn’t want it to turn out any other way, because then it might not end like this.
It’s a wonder why he let himself disappoint her the way he did to start today. Maybe not doing that as much would be a decent way to pay her back. He wouldn’t do that for anyone else, but…. “That’s why I love you.”
He wasn’t too sleepy to realize he said that out loud - for the first time. But he was too sleepy to jump up and draw attention it. So he just gave in, went to sleep, and hoped Annie didn’t hear him and torture him with that too.
Unfortunately, he was wrong on both counts. But Annie decided to go to sleep with a smile and save the torture for tomorrow.
And when she pulled off the covers and reached into his pajama pants, Jeff truly felt off the hook.
“Ah, perfect reward for a day well saved,” Jeff bragged. That might have been too much bragging, given how badly the day started thanks to Jeff. Yet Annie wasn’t pulling away. In fact, she stroked him for a few more minutes, although she barely looked at him.
Jeff would insist on eye contact if she was sucking him off, but he could let it go for this. Actually, he would let go regardless in a few more minutes. Or he would have if Annie didn’t pull her hand back from him.
Jeff figured she was getting ready for the next step, but she didn’t remove any clothing - on her or him. In fact, she went back to her side of the bed and started reading, of all things. “Um, Annie, you kind of skipped a few steps over here,” Jeff reminded. “Do you mind?”
“I will. As soon as you beg for it,” Annie blandly said.
“Come again? I thought I heard crazy talk, but that’s not your style anymore,” Jeff commented.
“It’s clear in English too. If you want to climax, you have to beg for it. Otherwise I won’t do it. And if you try to do it yourself, then no sex of any kind for a week,” Annie informed. Now instead of trying not to cum, Jeff was trying not to laugh - and was barely succeeding.
“Annie, I already know you’re funny. There’s no need for that kind of comedy hail mary!” Jeff chuckled. “Fine, if you’re still mad at me for some reason, I’ll just finish somewhere else and call it a night.”
“No!” Annie commanded. “Jeff, you’ve got to learn your lesson! And after four months in here, I know sex is the best way to get through to you. Or a lack of sex.”
“Annie, I just did what I always do. I do something stupid, you all yell at me, I redeem myself and barely have to apologize, then rinse and repeat next week. Why make a big comedy show of punishing me now?” Jeff inquired.
“Because we’re leaving Greendale soon, and that formula won’t work in the real world! It might have worked when you were a lawyer last time, but times are different now! You’re different now! If you’re going to do this crap anyway, you have to learn there are consequences. Like having to beg and embarrass yourself before the next time you get off,” Annie informed. “So are you going to learn your lesson early or not?”
“I think I’m going to sleep. I’m sure I can study my lessons in dream world. Good night,” Jeff huffed, turning his back to Annie and shutting his eyes.
Unfortunately, his back was still exposed to Annie, who took advantage by rubbing it and kissing his neck. Jeff then rolled on his other side to face Annie, but still closed his eyes and folded his arms. Yet this left his pants perfectly vulnerable as she reached into them again. Jeff thought of rolling back, but a few good tugs by Annie kept him still.
Jeff’s next idea was to stay quiet, so Annie wouldn’t know when he was on the brink until it was too late. But Annie just had to glide her finger up and down his shaft - and she just had to palm his balls like that too. God, why did he teach her that trick? Because he wanted her to make him cum hard, of course - and she pulled her hand away again before that could happen.
Reply
“It isn’t a gag. Beg me to make you cum or you don’t get to. You do it yourself or leave this bed, then no sex for a week,” Annie repeated.
“Damn it Annie, you know Jeff Winger doesn’t beg in bed! He causes begging, he doesn’t do it, and you know that all too well!” Jeff recalled, then got another idea. “And you know it. That’s why you won’t follow through. You can’t survive sex without me for that long, so this is just an empty threat! As empty as my balls will be in a few minutes, so hah!”
“I survived sex without you for three years,” Annie reminded. “Even after getting it, I know I can still last without it if I have to. I don’t know about you, though.” Before Jeff could insist otherwise or demean her plan again, she pulled the front of his pants down and sucked him off - for only seven seconds before she tucked him back in.
“Okay, now this really isn’t funny!” Jeff yelled, his newfound frustration building. “Fine, if I can’t leave the room, I’ll sleep on the floor!” He went to do just that, but the minute he laid down, Annie laid on top of him and grinded down on him as deeply as possible. As angry as he was getting, Jeff just couldn’t get Annie off him when she did that.
So he played dirty by grinding back, hoping to get Annie off and make her forget about not getting him off. Yet that failed too, as Annie got up and jumped back on the bed before Jeff could stop her. But with her up on the bed and Jeff still on the floor, he might be able to tug himself a few times - and it might be enough after that grind.
However, Annie came back and caught him right as he put his hand in his pants. “That’s a week and a half of no sex if you go further, Jeff!”
“Oh, come on, seriously?!” Jeff growled.
“That’s growling, not begging. You’re getting warmer, though,” Annie all but teased.
“Damn it, fine! I’ll just wait until you go to sleep, you can’t stop me then!” Jeff gloated.
“Really, Jeff? Me going to sleep before you? Especially when I have all these great books to reread? You must be too worked up to think straight,” Annie certainly teased that time. With that, she grabbed her Greendale backpack from the floor and took out one of her books to read - while keeping an eye on Jeff every few seconds.
Jeff groaned and went back to bed, his back turned to Annie again. But after only a minute - not long enough for Jeff’s hard on to go away - Annie put down the book and reached over to pinch his ass. This made Jeff get up again, but Annie was too quick and actually pulled down his pants.
In his shock, he couldn’t stop Annie from getting his cock and sucking him off again - for longer than seven seconds. As much as Jeff wanted to fight it, that mouth was too strong. So were those eyes when they looked up at him extra wide, and so was that cleavage when Annie pushed it up. That head then bobbed extra hard and fast on him, which almost made Jeff’s knees buckle.
Jeff again tried to keep quiet so he wouldn’t tip Annie off. But that became impossible when Annie’s tongue used that special trick on his tip. Why the fuck did he teach the super student of Greendale things?!
And how the fuck could she pop off his cock and go back to bed without sucking him dry?! Did she forget whose cock this was?! But with the way she brought him to the brink and left him hanging, he almost forgot too.
Jeff grabbed himself out of desperation, but Annie then decreed, “Two weeks, Jeff!” and made him stomp his feet like a child. Annie chuckled at the irony and went back to reading, then noticed Jeff trying to reach the bathroom and corrected, “Three weeks!”
“Come on, can’t I pee this out?!” Jeff spat out.
“Not unless you leave the door open. If you don’t, it’s three and a half weeks,” Annie shut him down. Now Jeff was losing it like he was on monkey gas. He stomped around, almost reached for himself again before stopping himself, and kept groaning from the buildup in his balls.
“Annie, you’re starting to kill me here! Please - I mean, uh, just finish me off!” he backtracked.
Reply
Jeff threw his head back and groaned in relief, especially when Annie started riding him. He was so blissed out and ready to go, he kept his hands to his side and didn’t try to embrace Annie. And by the time he was coherent enough to try, Annie climbed off him and rolled over to Jeff’s side of the bed.
“SON OF A BITCH!!” Jeff cried out at this latest blow - or lack there of. “Annie, I swear to God I’ll, I’ll….” But he was too horny and backed up to think of any good threats. None would be good enough to top this torture anyway.
“You know, since you won’t beg and take care of things, I guess I should take care of myself,” Annie offered, before placing her hand on her wet opening. As she inserted a finger and made it wetter, Jeff groaned some more and reached for her. But he stopped himself and growled again, not knowing what he was allowed to do - and not willing to risk four weeks or another way too short fuck.
Jeff tried to at least ignore Annie touching herself. But he couldn’t ignore her moans, even when he covered his ears. He couldn’t ignore her when she kept moving around to stay in his sight. And when she pulled her wet finger out of her pussy, trailed it up and down his cock and then sucked it dry, it was close to a breaking point.
“God! You dirty, precocious…..gah!! I just want to cum already!” Jeff yelled, lying on his stomach and banging his fists against the mattress.
“Well, that’s a good start,” Annie said while inserting her finger all the way inside her. Out of sheer madness at this point, Jeff resorted to humping the mattress - until Annie announced, “And that’s a month, Jeff, congratulations.”
Now utterly broken, Jeff practically screamed into the mattress and them slumped in defeat. “Okay, okay….” he finally muttered, then lifted his head up. “Annie….please let me cum.”
“Not quite, but you’re getting there,” Annie noted. Jeff didn’t even have any energy to nitpick anymore.
“Please, please let me cum. Get me off however you want, I don’t care! I’m at your mercy, just let me have my release! Please, please, please,” Jeff tried again.
“Closer….in more ways than one,” Annie answered while getting herself off deeper. And now that there was a race against time, Jeff finally didn’t care how he got it right.
“Okay, I’m begging now! I’m begging you to get me off, happy?!” Jeff spat, but instantly knew he’d have to sound less angry. “I need you to make me cum, I’m begging you….and I’m sorry. Don’t make my dick suffer because I’m such a dick, please!”
He saw he was on the right track when Annie’s face softened, so he finished with, “I know you feel like you haven’t changed me at all when I do this crap! But you have, you fucking have! I would have just left anyone else by now, both tonight and for good! But you’re still here, and I want you here, and I want you to get me off….because no one can get me off like you! I don’t want anyone else to! Please, I’m begging you to prove it one more time….”
This was by far Jeff’s most emotional Winger speech of the day. Something told him it wasn’t completely because he needed release. But he just tried to focus on Annie’s face and how it reacted, instead of watching her finger. When he couldn’t take the waiting, he laid on his back and sunk into sexual misery again.
That is, until he felt Annie climb on top of him and sink onto him again. Yet even that didn’t relieve Jeff, since she’d probably just climb off in no time. Yet when she kissed him, squeezed her thighs on him, and didn’t move when his arms went around her, it hit him that it actually worked.
And when Annie broke and whispered, “You can cum for me now,” something else hit Jeff.
Reply
By the time it was finally over and Jeff was utterly drained of everything, he found himself admitting, “Maybe I should beg more often.” This also let him realize, “I guess it’s not a punishment anymore, then. You’ll need another way to teach me a lesson in here.”
“I’ll think of one,” Annie muttered, somehow sleepier than Jeff was.
“You would, wouldn’t you?” Jeff let wash over him. Annie was diabolical like that - 80s cartoon supervillain diabolical, even. This seemingly sweet young lady was probably the most sadistic, vengeful person he knew when she was crossed. She was torturous, she was an evil genius, she was….a woman after his own cold heart.
Only she made it less cold and more gooey when she wasn’t being evil. Like when she just laid on top of him and gave him warm feelings he’d never had in bed before - even after losing this epic game of sexual wits. Even with the loss, he didn’t want it to turn out any other way, because then it might not end like this.
It’s a wonder why he let himself disappoint her the way he did to start today. Maybe not doing that as much would be a decent way to pay her back. He wouldn’t do that for anyone else, but…. “That’s why I love you.”
He wasn’t too sleepy to realize he said that out loud - for the first time. But he was too sleepy to jump up and draw attention it. So he just gave in, went to sleep, and hoped Annie didn’t hear him and torture him with that too.
Unfortunately, he was wrong on both counts. But Annie decided to go to sleep with a smile and save the torture for tomorrow.
Reply
Leave a comment