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He'd felt a little anxious, and the worry had left him unsure if he should continue, but Janine didn't even notice. She stood and turned, repositioning herself back in front of him, her soaking pussy again lined up with his now wrapped cock, ready for the two to meet.
Tommy's anxiety faded away. After all, what's done was done, he couldn't change it now, and at least they were being safe now.
He started to push inside her tight, sweet pussy. It was so tight in fact that he had trouble getting in.
"OH FUCK! STOP!" she yelled and he complied, "Oh god, you're so big. Your cock is so huge that I don't know if it'll fit."
Tommy wasn't really sure what to say in response. He'd probably only gotten an inch or so inside before he'd had to stop. His body wanted to pull back, and push forward again. He did so slowly, drawing back a fraction of an inch.
"Oooh," she moaned.
He pushed back in again, sinking an extra inch or so inside, before stopping due to the incredible pressure.
"OH GOD! SLOWLY TOMMY! Again, but slow," she cried.
He repeated the move, slower again.
She couldn't believe this. It was actually embarrassing the effect he was having on her. She'd known by looking at him that he was the biggest she'd ever had, but she hadn't actually considered what that actually meant when it came to sex. The only time she'd had such a problem had been when she was a virgin. After that she'd kept herself entertained with all kinds of objects, such as a hair brush handle, until she got hold of an actual dildo. Unfortunately for her present situation, she hadn't played with anything of Tommy's size. It was humiliating telling him to slow down, as she saw herself as the one in control here, the experienced one, deigning to grace Tommy with her body and skills, but that's not how it was working out. She was surprised at herself though. There was pain there, but amazingly the pain didn't make her want the experience to stop. The thickness of his cock, which wasn't something she'd focused on, was pushing her open to a degree she'd never felt, and though there was discomfort, there was something compelling about it, her body wanted more of it. So she asked him to keep going, but slowly, to let her get used to it.
Tommy concentrated to a degree he never had before during sex. He could tell she was in pain, but she pushed on regardless. He tried to tell himself that he would stop if she asked him to, but he was really, immensely hoping she wouldn't, as he didn't want to face that test.
He had over half his long, thick shaft inside her, and he noticed the difference now that he was wearing a condom. Her beaver felt fantastic, that was undeniable, but he also knew that it didn't feel as nice as it had before. There was a layer of latex between his sensitive skin and her soft folds, and of course that insulated the sensations. He tried to remember if they'd mentioned that in sex ed, he had been embarrassed and wished he was in English class instead, but he was pretty sure that they hadn't covered that particular fact.
Tommy was slowly stroking in and out now, using about half his cock, and on every third or fourth stroke he felt himself slide and extra fraction of an inch inside.
"Oooh, UH, oh, uhh, ooh, uh, OH, oooh," Janine moaned and grunted to each of Tommy's strokes, her volume rising every now and then.
Janine lay atop her desk, her boobs pressed into the top with her arms bordering them, trying to support her torso and keep her weight off her tits, but she was failing miserably. Her entire room had ceased to exist as Tommy had forced more and more of his enormous cock inside her. The only thing that she felt, the only two things in her existence, was her crammed honey pot, and Tommy's titanic truncheon, plumbing her depths.
Tommy had his hands around the thinnest part of her waist, pulling her back into him, feeling the part of her waist that started tapering out towards her hips. She felt much more muscular than Ms Stern, but that wasn't really surprising as Ms Stern was much older, and of a different body shape. Any further thoughts of comparing Janine with anyone else were abandoned, as he took the opportunity to slide his hands all over her smooth hips. He fingered the thin straps of her thong, pulling on the elastic and letting them snap back into her.
He wasn't taking the time to look, or measure, but he was pretty sure he was over two thirds, possibly even three quarters of the way up inside her snatch now. His pussy pleaser was pushing into her depths repeatedly, with a degree of difficulty. Janine was juicing as if her life depended on it though, certainly the serenity of her pussy needed the lubrication her body was producing.
He was fucking her pretty fast now, watching her shake from his efforts, her dirty blond hair matted with her sweat.
Janine struggled to remain on her feet. The pleasure and full feeling had her almost out of her mind, and her legs threatened to fail her. If it weren't for Tommy, she would have already fallen to the floor. But it couldn't last forever.
"Uh, oh, Tom, Tom-my, we have to, have to move, to the bed, I can't stand up, anymore," she struggled to tell him.
Tommy didn't want to stop, and his first instinct was to bodily pick her up and carry her to the bed, keeping her impaled upon his tube steak.
Janine was surprised when Tommy reached down and pulled her up by her tits. They now stood facing the same direction, joined cock to pussy. He was pushing hard up into her, and she was clenching, afraid of the pain he'd cause if he pushed all the way in all at once. He put his arms around her, hugging her from behind tightly. A moment later she lurched into the air as he turned and flung her onto the bed. At least, that's what she assumed he was trying to do. If it weren't for the studly cock he was manipulating into her tight cunny, and the fact that he was swiftly wearing her out, she would have found it funny. What he actually did was hug her tightly and pick her up off the ground for about half a second, before dropping her back to her feet. She stumbled, surprised, but caught herself before falling all the way to the floor.
She pushed back against Tommy and then moved forward, extracting herself from around Tommy's thick log, causing a loud pop that neither of them acknowledged that they'd heard.
Tommy was embarrassed that he'd failed to pick her up, but he wasn't at all surprised. He really wasn't sure where the urge had come from as it was really out of character for him.
Janine turned and hopped on the bed. She laid her chest down flat on the bed, squishing her breasts against it. She kept her knees under her though, which left her arse stuck up high, giving him great access to her treasures.
"Come on Tommy, I want that cock inside me. I can take it, I know I can," she pleaded.
Who was he to deny that?
Tommy quick-stepped over to the bed and climbed on behind her. His prick looked a little strange squished inside the clinging latex, and he thought that the little reservoir in the end looked a little small. Still, despite the insulation his cock yearned to dive back inside her slick, tight little honey pot. He admired her round bum, her creamy skin split by the maroon strings of her thong, the slick lips of her cock-sheath peeking between the soft, round curves of her tush. Again he pulled the crotch of her sexy panties to the side, hooking it over the smooth mound of her booty, listening to it squelch wetly as it parted with her slick pussy lips.
He carefully lined up his coated cock with her dripping beaver, and then slowly pushed back inside, "Aaaaah..." he sighed.
"Ooooh," she moaned at his entrance.
"Oh yes," he blurted, as he got back into the rhythm of slowly putting more of his giant wang into her tiny box.
Tommy didn't realise how much he was helping Janine stand up, but he did notice that pushing and pulling his hard shaft back and forth inside her buttery quim was for some reason much easier.
"Oh, oh wait, oh Tommy, Tommy, slower," she pleaded.
He couldn't hear her anymore. He was now seeking his own release, and was steadily putting more of his shaft inside her.
Tommy was thrusting just slightly past the threshold of what would have been completely comfortable for Janine. She moved forward on the bed slightly, pulling her arse further away from Tommy, but it was no good, she could tell he had now essentially, 'gotten his fuck on', and he just extended his strokes to take up the extra space. The longer strokes did cause him to accidentally slip out though, and she sensed his panic at the loss of her tight quim surrounding his pecker. Disaster struck when he found it again and pushed inside.
When he found her pussy again he slammed inside her, and Janine again tried to move forward to soften the blow, unfortunately she lost herself and slipped forward, falling flat to the bed on her stomach.
Tommy meanwhile was going deep, and wasn't willing to risk slipping free again, so held himself inside her. As she fell forward, he fell with her, which unfortunately for Janine pushed almost the entire thing up inside her in one huge stroke.
"AAAAAAAAHHH!" she screamed. "MOTHERFUCKER! OH FUCK! OH JESUS Tommy, Tommy... oh god..." she felt tears gathering in her eyes.
Tommy was mortified, her scream had lifted the haze he'd been in and he felt terrible, or at least, most of him did, there was a small, well large apparently, part of him that was experiencing the pleasure it had been seeking. Tommy felt guilty, but his cock was as happy as a pig in mud.
"I'm sorry Janine, I'm so sorry, I slipped when you moved... I'll... I'll pull out..."
Janine was in a bit of pain, but to be honest, the worst of it lasted less than a second. It was a shock, but she probably overreacted. She felt Tommy start to pull back.
"No! Stop. Just hold still Tommy, hold still," she ordered him.
He was lying almost flat on her. He certainly wasn't supporting any of his weight. His pelvis was pushed up hard behind hers, joining them snugly.
"Fuck your cock is huge Tommy, you have to be more careful, give a girl a chance to get used to it. I know it's frustrating, but think of the girl honey," she told him.
"I'm sorry, I didn't mean to," he replied.
They fell to silence. Tommy manoeuvred his arms around, surreptitiously copping a feel of her side-boob as he got them under himself.
Janine's movements were subtle. She'd mostly gotten used to him now, and she was pretty sure that she could take some light fucking now, in fact she desired it, but she was still a little afraid of his size and the potential for pain involved. So she lightly, almost imperceptibly started to twist and flex her hips and buttocks. The subtle movements caused Tommy's cock to probe her gently, preparing her depths for further assault.
Tommy eventually realised that Janine was flexing her hips and buttocks. It wasn't quite fucking, but it was feeling pretty good. Her pussy was so tight that even such slight movement was stimulating him, even through the condom. His passion was rising, and he wanted to start fucking her again, but he knew he had to be careful. Did she realise she was making these little movements, he wondered.
As slowly as he could, he withdrew a couple of inches.
Janine moaned as she felt him pull back gently. She was worried, but it felt good, so she let him continue. When he pushed back in she was surprised at the lack of pain. She expected some, but instead there was just a little bit of discomfort.
Encouraged by her lack of reaction, Tommy repeated the stroke, and even picked up the pace a little.
"Oh god," she moaned, as Tommy resumed fucking her with slow strokes, this time much deeper than before.
Tommy was fighting the desire to start slamming in and out of her. He lay on her back, hunching his hips and pelvis in order to drive his slab of cock meat back and forth inside her. He filled his hands with the sides of her boobs, and jiggled them in his hands. He drummed his fingers against them as they jiggled to his motions.
His speed and force continuously built. His strokes were still short but he was certainly starting to slake his own desires.
"Uhhh, yes, ooh," he grunted and moaned as he thrust his hips.
"Oh, oh, oh, oh yes," Janine gasped as he continuously pushed his pork sausage into her.
Tommy spread his legs, wide, and leaned up, looking between the two of them. Her round buns jiggled to his motions, her thong still sexily decorating them.
Tommy's hips were swinging back and forth, sort of rolling and rotating, allowing him to fuck Janine without having to exert his entire body. He felt like he could keep it up forever.
He put his hands on her jiggling buns, sinking his fingertips into the soft flesh, and giving them a sensual squeeze. Again he felt up the material of her thong, something about having sex with her while she still wore her panties was driving him wild.
He kept his hands on her sexy, round bum between the two of them, and pounded into her with everything he had, using his whole body now and letting his torso rest on her back while trying to balance his body to keep as much weight off her as possible.
"OH FUCK TOMMY! YES! FUCK ME! FUCK ME! FUCK ME!" she screamed in response.
His efforts to thrust harder into her was changing their position, causing him to get further behind her and push her legs underneath her somewhat, until they were fucking doggy style. Tommy was exerting himself now, trying hard to reach an orgasm despite the condom he was wearing.
"Come on... fuck... oh god..." he moaned.
"OH FUCK! FUCK! FUCK! I'M CUMMING! YES! YEEEEEEEEEEEEEESSSSS!" Janine screamed as she came.
Tommy felt urgency like he'd never felt before. He needed to come, and now that Janine was coming too, he wanted to join her. He slapped her arse.
"YES! FUCK!" she shouted.
He forced his hands beneath her and grabbed hold of her big, soft breasts, squeezing them hard, and finally reached the point of ejaculation.
"YES! I'M FUCKING CUMMING TOO! FUCK YES!" he shouted, joining her in ecstasy.
Tommy felt the cum firing into the condom, causing the head to be drenched and getting all squelchy. It was something that Janine was used to, but Tommy certainly wasn't.
He continued sliding back and forth inside her as they both came down from their orgasms.
They panted for a moment and then Tommy finally, slowly pulled out, his cock having lost a lot of hardness.
They lay side by side on the bed, catching their breath.
Tommy wasn't really sure what to do with himself now, but he wasn't entirely comfortable, laying on her bed with a full condom dangling off the end of his dick.
Sex Ed hadn't really covered how to remove a used condom. He sat up and after a few false starts, started pushing it off towards the end.
Janine looked over and giggled, "Mmm hmm hmm, Tommy, have you ever used a condom?"
He stopped and looked at her. "No, I haven't."
"But you're not a virgin, are you?"
Even if he had been 15 minutes ago, he wasn't now he thought, but he hadn't been then either, "No."
"Naughty boy, here let me show you," she replied.
Janine manipulated the condom off his cock slowly, showing Tommy how to keep as much spunk inside it as possible. She then deftly tied a knot in the end and threw it in a small bin by her desk.
"I'll have to throw that in the big bin under some other rubbish so Dad doesn't find it," she told him with a smile.
He half-smiled in response.
Janine lounged back on her elbows while Tommy sat at the edge of her bed, a little uncomfortable.
"Everything ok?" she asked.
"Yeah I just... I should probably go, but I don't want to like... run off... but my Mum was probably expecting me hours ago."
Janine smiled in humour, "Oh you mean now that we've had sex you need to leave, but only because you have to, it's not your fault, right?"
Her smile didn't look forced or sarcastic, but it didn't match her words, so Tommy wasn't completely sure how she felt.
"Really... I mean, maybe I can just give her a call, let her know I'm still out..." he suggested.
She grinned now, "I'm just kidding you Tommy, it's cool, I've got stuff to do anyway."
Tommy started pulling on his clothes while stealing looks at Janine lounging back on her bed, her panties covering her little honey-pot, but her big titties lying on her chest, sticking up like a pair of hills. Another notch in his bed post he supposed. Or was it her bed post? It was her bed...
He thought of Brian and Lissa and the date they'd had. Janine wasn't much older than him. She probably represented his best chance yet of going on a date.
He mustered his courage as he buckled the tight pants. It was a long shot, but aside from Sarah, all the women he'd slept with were significantly older than him. And as for Sarah, going on a date with her, in a public place, was simply downright scary as she'd be liable to suddenly scream out that there was a bomb in the cinema or a snake in the restaurant or something.
"Janine..." he said, asking for her attention.
She turned her eyes to his, glanced at his crotch, thinking of his now flaccid, heavy, thick cock, and then looked back into his eyes.
"I was wondering... if..." come on, he thought, you can do it, "maybe, if you're not busy, we could get together? Maybe go to a movie?"
If it wasn't for his cock, he'd have been adorable, but with that cock, the word adorable simply didn't fit. She wasn't sure what did fit exactly. Hung? He was certainly that, but it didn't describe his personality. Cute? He was cute enough, but that dick was not 'cute'. Majestic? His member was that and more, but he was a little skinny for that. She gave up trying to classify him.
He asked her to go to the movies? Most guys asked her out just to get into her pants, and she was usually happy enough to let them in. Once they'd gotten in though, they usually just wanted to 'stay in' and get into her pants every chance they got. But he was 'in' already, and yet he'd asked her out afterwards. Not, 'let's do this again' or 'want to hook up again later', but literally a date. It was unusual. She'd gotten used to a 'date, date/sex, sex, sex, sex and so on' procedure, and if she was honest, she enjoyed it. Maybe 'sex, date/sex, date/sex, date/sex and so on' would work just as well?
She pictured herself on a date with Tommy. He was sweet. She imagined he'd be pretty attentive and thoughtful, he was after all a bit of a nerd from what she knew from school, and they were usually fawning all over their dates. But she'd never dated a nerd, never even considered it, never been approached by one. Would she date one now? She wasn't at school anymore, was she going to be the girl she was in high school all her life? She still hung out with her friends a bit, but a lot had gone on to college. It's not like she'd have to hang around with people making fun of her for dating a nerd. Besides, if she ever really had trouble, she could show them the size of Tommy's manhood, which would shut pretty much anyone up.
Tommy waited with baited breath. She was thinking about it, he could tell that much, but he had no indication which way she would decide. She'd hung out with the pretty popular kids in high school, not the super snobby, but she was out of touch of him at the time. But wasn't life after high school supposed to be different? She was out, and he was just about finished.
He so wanted her to say yes.
She'd go with cute, she thought, as it matched his face, physique and personality. His enormous donkey-dick was simply the exception to the rule.
"Sure," she said, "give me your phone and I'll give you my number."
He fished his phone out of his pocket and handed it to her, feeling a little lightheaded.
She punched in her number, saved it to his contacts, and then handed his phone back.
