Originally posted as a comment fic for a kink meme at Milady/Milord, as I answered a prompt from an anonymous commenter. But since I had an open spot today, I decided to post it here as well. Yet after this and "Mistress Annie" I promise there won't be any more kink from me for a while.
Jeff had held back dirty fantasies of Annie longer than he cared to admit. And quite a good deal of them involved her full, heaving, marshmallow shaped, gradually more and more exposed breasts.
Truthfully, he had seen some bigger ones – he would know after all his years of careful studies. But….these were Annie's boobs. And considering how Annie made him lust after body parts he rarely had before – like eyes, a smile, hair and hands – huge boobs were a welcome and supple constant. Especially these boobs.
So when he finally got his act together and told Annie how he felt one weekend, the boobs were a big part of how he showed her what she did to him. He could have buried his face in her tits all night, and doing so killed at least a good 10 minutes. Yet he put the more advanced Annie's boobs fantasies in check, since this was their first night together and Jeff wanted to ease her into this – and himself into her.
But the fantasies he didn't get to fulfill still hung over him the next morning. It didn't help that Annie dressed herself in one of his bed suits – with two buttons open and clearly no bra on. Nevertheless, Jeff stayed focused on the rest of Annie, even when she decided she wanted to talk about where they stood.
Jeff had trained himself to endure these 'define the relationship talks' before he invited Annie to his apartment last night. He knew that he wanted more than sex from Annie – and if he still wasn't entirely confident that he would succeed, he wanted to try now. Annie was more than worth the effort – even before the amazing effort she showed in bed for their first time. He made sure to tell her that, which made Annie hug him in relief that this was actually for real.
It was more than real all right – especially since Annie bent down to hug a sitting Jeff and gave him quite an eyeful of cleavage. With that, Jeff felt he earned an extra reward for getting through this. So he sneakily kissed the valley between her tits right before Annie pulled away.
"Jeff!" Annie scolded him as she put her hand over her cleavage – but it couldn't hide the blush on her face. "Come on, it's not like you need to hide those from me now. You did a worse and worse job of hiding them from me when you tried," Jeff reminded her. Annie started to scold again, but then thought back and conceded, "Yeah, maybe…."
"Definitely….you have no idea," Jeff admitted as he returned to ogling her chest. "It wasn't easy to hide that I wanted you….and these things made me work really hard at it. You know how much I hate working," Jeff stated as his hands went onto Annie's waist.
"I hope….they weren't the only things that convinced you to man up," Annie hoped while she could still talk.
"Of course not….they were a big and perky and perfect and…..yummier than I ever imagined reason." Jeff ran off as he palmed her breasts over his shirt – which was hot in too many ways to list. "But I don't know….maybe boobs do mean more when they're attached to the right person. Attached to you….well, they're way too good to be names for monkeys."
Even mentioning that monkey didn't make Jeff or Annie less hot, especially when Jeff capped it off by kissing and nibbling the real Annie's boobs through his shirt. Finally he went up to kiss the actual skin on her breasts, burying himself back in her cleavage while setting the rest of her ample flesh free. Once Jeff helped Annie get the rest of his shirt off, he suckled on her actual nipples as deeply as he did last night, which made Annie's knees buckle.
That gave Jeff a long overdue idea. Although he wanted to slowly introduce Annie to more intricate sex stuff, he couldn't hold back on this fantasy anymore. "Get on your knees," Jeff stated, stopping right before he could say please and sound desperate.
"All right….I figured it was supposed to taste better the second time anyway," Annie reasoned as she sank to her knees. "No no, you won't be doing that to it…but it will play a big part in this anyway," Jeff hinted. He pulled down his pants so he could explain faster, then sat back down on the couch, grabbed his erect member and aimed it between Annie's chest.
"Why are you putting it there?" Annie inquired. Jeff hoped this wouldn't turn into a birds and the bees type lesson, since he still wanted to see Annie as an adult. So he showed her without words by taking her breasts, putting them on both sides of his cock and thrusting in between them twice.
"Fuccckkkk…." Jeff couldn't stop himself from groaning loudly at the sensation. Annie's own groan was much quieter by comparison, yet Jeff heard it clear enough. "Oh…." Annie realized once they both got quiet. "They can be used for that too?"
"They can be used for a lot of things….and I imagined every one," Jeff confessed as he fucked her rack as slowly as he could. "God, Annie, my imagination didn't do these things justice….and it worked overtime!"
"Geez Jeff….oh God, Jeff…." Annie trailed off as Jeff squeezed her breasts tighter against his cock, moving his thumbs onto her nipples. "You act like…..oooh….you haven't seen a ton of these before…."
"Not like these…." Jeff admitted, hoping he could stop talking and just focus on the warm, pillowy feeling from her tits. He jiggled them up and down against his erection, sometimes just doing that instead of thrusting into them. But he got in a good deal of thrusting too.
Jeff focused enough to dip his cock head between the hidden center of Annie's breasts, letting it rub right against it. He then reluctantly took his dick out and rubbed the head against her nipples, even putting the slit right against one. Having it cover Annie's tempting nipple, even slightly, got Jeff fired up again to go back and fuck her tits even harder.
"Jeff…..God, Jeff, keep doing that…" Annie asked shakily.
"I plan to….I got way too much wasted time to make up for," Jeff confessed. "Why didn't I do this earlier?"
"You wanted to….do my….vagina first, remember?" Annie reminded while just barely getting out even that word. Amazingly, that made Jeff laugh even while he was screwing her breasts. "I meant why didn't I do….all of this sooner? I had reasons, but these things and….well, you….make them look so stupid…."
That actually made Annie a bit wetter and hotter than the tit-fucking. With that, she made her move and got Jeff's hands off her breasts, so that she could grab them and start moving them against his cock. "I'm gonna have to start learning this stuff now, right?" Annie rationalized as she thrust her chest up.
Jeff let Annie work out the mechanics on her own – but naturally, the A+ student got the hang of it fairly quickly. He placed his hands over her own and her boobs to get in one more squeeze, then moved them up and let her go to work. His hands went on her shoulders to steady her, then froze along with the rest of him when Annie looked up at him.
Her doing that brought Jeff closer to cumming last night than he cared to admit. Yet seeing those big beautiful eyes gaze up at him while her big beautiful boobs were rubbing his shaft brought him thatclose to his first….premature ending in years. Somehow Jeff contained himself, although the strain on his face told Annie all she needed to know about how well she was doing.
As such, she gazed back down and intensely studied Jeff's cock head as it kept emerging from her chest. In fact, it was getting closer and closer to her mouth, especially when Annie bent down a bit lower. Jeff noticed this and wanted to stop her, fearing it really would end too soon if she got lower. But when Annie stuck her tongue out onto his head and he didn't cum – amazingly – Jeff figured he could risk it a little longer.
Yet Jeff pumped slower between her tits as he intended to pace himself before the last act. However, he soon started going faster and getting near Annie's mouth again before long. For her part, Annie took another few tentative licks – then started moving her lips downward too.
Before Jeff knew it, his tip started sliding into Annie's mouth with each thrust – and then Annie put her head down further until Jeff's entire head was in there. What's more, she put her teeth at the bottom of his head to trap it in.
Jeff now had his shaft in between Annie's warm, hot, soft boob cavern, with his head trapped inside Annie's warm, hot, soft mouth cavern. That double-whammy combined with Jeff's hands going into Annie's hair, her eyes looking up at him again – plus her tongue licking all over his tip and her moaning from the taste – made Jeff snap.
"Fuck fuck fuck!" he yelled out of control, as he thrust rapidly into Annie's mouth and tits a few final times. He then willed himself not to cum in her mouth, fearing she wasn't ready for that yet. So he got her mouth off him, pulled his cock out of her boobs and then just rubbed the head against them before he finally exploded.
Annie finally got her hands off her boobs so they wouldn't get sprayed, although her breasts weren't so lucky. Jeff coated as much of her tits as he could – and with all the buildup even after last night, it was a good amount. When he was finally finished, it took several more seconds to stop groaning and focus downward, taking in just how wet Annie's boobs were.
He had never been more tempted – really never tempted period – to lick up his own cum before. If it meant he could lick it off Annie's wet and well fucked tits, it might just be worth it. But he was still properly grossed out and manly enough to shake that off – plus he didn't want to gross Annie out that much either. Therefore, he settled for forcing himself to walk again, so he could find some tissues and wipe her breasts clean.
"Yeah….why didn't you do this sooner?" Annie asked once he was done and she had enough energy to talk again.
At least now that her breasts were clean, Jeff could laugh right into them and revel in how he didn't need confusing, puzzling answers to that question anymore.