Tommy's Neighbourhood Ch. 06

She looked away from his cock, into his eyes for just a moment to give him a smile of encouragement, then went back to staring at his swelling sausage.

He rubbed the sides of her breasts, feeling the soft, undulating flesh give under his caress.

Janine was focused on her ministrations. Tommy's cock was about half-hard. It had thickened quite a lot, but was still quite soft and spongy to the touch. She was in a kind of trance, almost shock, at the size of his organ, as it continued to grow in her hands.

Tommy jiggled her boobs in his hands, watching them shimmy and shake inside her bra and top. It caused her sweater to inch downwards, revealing just a little more breast flesh to his hungry eyes. He felt the resulting surge of blood flow to his rod, causing it to thicken and harden just a little more.

He looked down, over her head, towards her tush as it rested on the bed. Her position had pulled her sweater up, exposing the creamy skin of her lower back. Her jeans were tight, but Tommy was still able to catch a glimpse of her panties. She was wearing a G-string, a maroon colour. The sight of the flimsy underwear caused another throb in Tommy's cock. It had thickened and hardened until it was straining for attention, now nothing less than a rock solid erection.

Janine marvelled as his cock surged in her light grip, and now stood up on an angle away from Tommy's body under its own strength. It was enormous, probably the better part of a foot or so.

"How... how big is it Tommy?" she asked him.

He was a little startled from his reverie of feeling up her nice, big tits and gawking at the tiny, itsy bitsy panties he could see. He actually had no idea how big his cock was, he'd never bothered to measure it. He'd never even thought of doing so. Was he supposed to know, was it embarrassing that he didn't?

"I-I don't know," he stammered, a little uncertainly.

Janine looked at the pulsing member, slowly weeping a drop of pre-cum. She had to know how big this huge cock actually was. Whenever she gossiped with friends, they always tried to one up each other with the size of the biggest cock they'd had. Tommy's monster easily surpassed any of them, so she'd need to know the exact figure to rub it in all of their faces.

"I'll measure it, wait here," she said, then stood from the bed and darted out her door, dragging her soft breasts from Tommy's grasp.

He found himself standing naked in her bedroom. He noticed a few things that made it clear her family had a lot more money than his. He noticed an iPad and a laptop, as well as a TV and DVD player, all in her bedroom. He remembered that Tiff and she herself said that her Dad cut her off, but it seemed like a huge contradiction to Tommy. Maybe rich people were just weird.

Janine reappeared in the bedroom like a whirlwind. Before Tommy knew what she was doing she was on her knees in front of him holding a measuring tape up against his tool. She then wrapped her hand around it and gave it a squeeze.

"It's not fully hard is it?"

She hadn't been gone long, but he'd gotten distracted, unsettled, left alone in a girl's bedroom naked, the slight possibility of it all being part of an elaborate prank. So she was right, it certainly wasn't straining the way it was a moment ago. He shook his head in reply.

"Well we can't have that," she said. "Do you want to see my boobs?"

Nothing would please Tommy more. "Oh god yes," he answered.

She took hold of his arms and turned him around, before pushing him back so that he sat on the bed. He stared at her in rapt attention.

Janine decided it was time to play out a little fantasy she'd had, by doing a little strip tease for Tommy. She'd considered it a couple of times, but first, she'd never really had the opportunity, in the past the guys had just been eager to get them both naked and get at it, and second she'd never before been pretty confident that the guy wouldn't spread rumours about her being some kind of stripper-slut. Tommy didn't seem the type to spread rumours, after all it seemed like he had quite a few secrets of his own.

Tommy watched as she went over to a small radio and turned it on. He didn't recognise the song but it didn't matter, because Janine started scanning through stations. She stopped on something he didn't recognise, but that wasn't a hard thing to do. The music had a strong, slow beat, and it sounded pretty old.

"This will work," Janine told him as she turned to face him.

Thinking about something and actually doing it were two different things Janine thought, as she realised she was about to do a strip tease for a guy. She wasn't sure where to start at first, but then she remembered she usually had the urge when she was dancing, not every time she danced of course, but she realised she had to let the music take her there.

He watched as she started by swaying to the music, sensually twisting her body. Then she added her arms, swaying and moving them to the music. She started running her hands up along the sides of her body, as he stared, enraptured.

Janine began to feel the music, and let it control her body.

Tommy was amazed at how sexual this was. She was fully clothed, and yet she was eliciting such passion in him.

Janine took hold of her top, crossing her arms across her torso, beneath her breasts, and lightly, teasingly tugged it up just a little bit, folding it back over itself. She took the opportunity to peek through her eyelids at Tommy, to see his reaction. Predictably, he was staring at her movements. She pulled the top up even higher, exposing her navel. She heard Tommy gasp as he caught sight of her pierced navel. She'd caught hell from her father over that. She continued to sway her hips and twist her body back and forth. The idea of taking a stripper course was appealing to her at that moment. She had to start pulling the top out over her boobs now, feeling the material stretch in her hands.

She was really going to strip in front of him, Tommy realised. She pulled her top slowly upwards, exposing what looked like a cotton bra. The cups were mostly white, with little red flowers, while the trim was in the same maroon colour as he'd seen of her panties. He'd already seen most of her cleavage, but now he could see both ends, the bottom of her cleavage below the top and the rest of her long cleavage just before it was obscured by her rising top. It had already been clear that she was quite slim once you got past her hips but before you hit her chest puppies, but seeing her naked flesh really drove home the point.

Her top finally cleared her tits, and he noticed the top seemed so much smaller when it wasn't stretched out. Her breasts were snug in her bra, and it seemed to fit well, as her breasts looked quite comfortable and weren't bulging out of it. If it wasn't clear that she was so stacked, Tommy may have been disappointed.

She pulled her top off over her head and hair with one arm, flinging it aside, before throwing her head around, causing her hair to splay out in a halo around her head. She paused with her hair hanging behind her again, in her bra, jeans and boots. She pushed her chest forward, accentuating her breasts, while he could see her butt stuck out backwards.

Janine was enjoying this, and she knew she'd be doing it again. She kept stealing furtive peeks at Tommy and revelled in his attention. Whether it was him or not, she wasn't certain, but she suspected that having any male so captive would be exciting. She turned around to face away from him as she prepared to pull off her jeans. Then she remembered her boots, and realised she had to get them off first. Strippers didn't wear boots like that, they either wore easily slipped off shoes, or long, come-fuck-me boots that they could remove sensually as they sat down, hers were short, and zipped up, how was she going to make that sexy? Janine turned again to face Tommy as she had an idea. She threw her leg up and brought her foot down on the bed, between Tommy's thighs, narrowly missing his balls. That would have ruined it all.

"A little help?" she asked as she gave him a wink and looked at her boots.

Tommy looked at her foot between his legs. If he hadn't been so aroused he'd have thought she was going to kick him and flinched away. He saw the zip, and pulled it down, releasing the boot from her foot. He wasn't sure how much help she wanted, so he held onto the boot to help her remove it.

He was helping her out of the boot, holding onto it, not really part of her planned strip, but she hadn't thought of her boots anyway. She twisted her foot out of the boot, and Tommy placed it on the floor, before the two of them repeated the process for the other boot.

She turned away from him abruptly, flicking her hair out behind her and stepped away, before placing her legs a little over shoulder width apart. He watched in awe as she bent over and put both hands on the ground, causing her hair to hang low and brush the ground. He could see her panties peek up above her waistband again.

She stood back up but kept her butt stuck out at Tommy. He could see her unsnap her jeans as she started jiggling her butt at him, causing the cheeks to jump and dance. She had her thumbs beneath the waistband as she brought her hands around the back, dropping the jeans only slightly. The top of her thong came into view, with thin material acting as waistband and crotch, but meeting in a triangle of white cotton with red flowers, all edged in maroon, matching the bra cups.

Tommy moaned in arousal.

She pulled the waistband down beneath the cheeks of her bum, and then bounced her butt on the top of her jeans as Tommy stared transfixed at the jiggling flesh. She let go of her jeans and ran her hands back up her sides.

Janine thought about what to do next. She wanted to take her bra off, but should she do it facing him? Facing away? Should she hold the bra onto herself or let it drop?

Janine reached back behind her, and Tommy knew she was going for the catch of her bra. He was awed by the deft way she quickly unsnapped it, but then, she had to do it every day. She kept her other arm in front of her, but slid the straps down her arms. He couldn't believe how sexy she looked, without a stitch of clothing from her head to her tailbone, her naked back unmarred by anything until reaching the skinny maroon and white thong, followed by her jeans lodged beneath her sexy butt.

She slowly turned to face him and he could see she was holding the bra in front of herself with her left arm, pressing it up against her big titties. She suddenly pulled the bra free with her right arm, leaving her naked breasts smooshed up against her left arm, bulging above and below her outmatched limb. She jiggled her boobs with her arm for a moment as she stared into his eyes. They failed to make eye contact though as Tommy was unashamedly staring deep into her breasts. He even missed the sight of her panties peaking out of her open jeans at the front, displaying the common white with red flower material, slightly discoloured due to the moisture accumulating at the junction of her tight, sexy legs.

Again she turned away from him. She released her melons, allowing them to hang from her chest and Tommy could see them shimmy, slightly visible either side of her chest. She snuck her thumbs under the waistband of her jeans again, and bent over to push them down her creamy thighs, followed by her tight calves. She pulled her legs in close together, just in time to hide her boobs as they hung down and would have otherwise become visible between her legs. With her jeans pooled around her feet she somehow gracefully slipped out of them completely and stood, now naked aside from her little thong.

He could feel that his cock had reached iron-hardness, and stood like a flagpole from his groin in his seated position on the bed.

She turned to face him, holding her breasts in either hand, concealing the nipple and as much tit-flesh as she could hold.

Janine was proud of her little strip tease, and she'd enjoyed it. She knew she'd be doing it again. She even began thinking about the kinds of clothes and lingerie she could wear to strip out of. Then she looked down at the sight of Tommy's cock.

"OH MY GOD!" she exclaimed.

Tommy was startled, but was immediately distracted as Janine forgot what she was doing and dropped her tits to jiggle and come to rest on her chest. They were a hefty size, with pink areola. Her nipples looked hard, and quite thick. Tommy wanted nothing more than to take one between his lips, into his mouth and suck on it.

"It looks even bigger than before," she said before scrabbling over to kneel between Tommy's legs.

Softly, she touched it with her fingertips as if to confirm it was real, but not wanting to scare it away.

Tommy couldn't decide what to watch, her big, jiggling tits as she moved around, her tight rear end as she turned this way and that, or now her lustful, appreciative eyes as she stared at his erect manhood.

She lightly ran her fingertips all over it, before taking it into her hands and eventually moving towards stroking it in her light grip.

"I've never seen a cock so big, or so hard Tommy. You're gifted. Do you know how big it is?"

Tommy furrowed his brow, wondering why she was asking the same question he couldn't answer before, "I don't know, you were going to measure it?" he said before indicating the tape she'd dropped with his eyes.

"Oh, right," she said, and moved to grab the tape.

Tommy enjoyed the way her breasts swung, and her tight body moved and flexed as she grabbed the tape.

She knelt back in position and put the tape alongside his dick. She fumbled, and tried to find the right spot to start her measurement.

"Oh god Tommy," she told him, "your cock is 10 inches long. And I thought 6 inches was long."

It didn't really mean much to Tommy, he was just focused on Janine's hardened teats, and longed to get them into his hands, or mouth, or both.

Dropping the tape, she started kissing his dick. It was like a switch had flipped in her brain, and now she was going to lavish his cock with her oral attention.

Over the next few minutes she used her tongue and lips and hands to caress him as best as she could. She was obviously experienced, and very good, but it wasn't Tommy's best he decided. Thinking that made him feel guilty, so he decided he wouldn't tell her that. As she worked she moaned, while her lips kissed, and sometimes tried to swallow his shaft.

She moved back off his cock, panting quite a bit.

"Oh my god, it's amazing," she paused, taking a few deeper breaths and stood up in front of him.

Tommy took the opportunity to admire her sensual curves and the way her breasts heaved with her breathing.

"I have to have your cock inside me," she said, looking up into his eyes for the first time since she'd measured him.

Tommy was certainly keen and stood up, eager to get things started.

"Wait," she said, "I have to get... we need to..."

She went over to her desk and opened a drawer.

Tommy watched her delectable rear twitch as she moved around. She bent over to look deeper into the drawer, obviously searching for something elusive.

Tommy couldn't take anymore. He stepped over to her quickly. His hardened cock led the way. He pressed himself against her, the spongy head of his prick colliding with her arse crack and pushing upwards as Tommy shoved himself against her, sliding along the thin fabric of her thong.

"Oh!" she gasped.

It was quite a shock for this timid, well-hung geek to suddenly man up and push himself against her. She immediately felt his prick pushing up along her crack, seeking entrance wherever it may, rubbing against the crotch of her thong, wedged into her crack and being pushed deeper.

Tommy put his hands on her hips to give himself a bit of leverage. The skin of her bum cheeks as they pressed in at the sides of his schlong felt so smooth and supple. He used his hands to push them together tighter around his cock head as it burrowed into the sweetness.

"Oh god," Janine moaned.

She wasn't really sure why, but somehow, having driven Tommy's lust to the point where he had to push himself up against her, was extremely erotic. She was already very wet, but she felt her pussy spasm, and soak her thong until it was sopping wet. She could feel the ridge around the head of his prick dragging back and forth between her cheeks as he forced himself against her and her thong.

"Oh damn," he moaned as he pushed himself against her. He caressed the waistband of her thong panties, feeling the smooth, supple skin beneath it. He ran his hands up the smooth skin of her sides, much as she had, feeling the tight muscle beneath, until he reached the bottoms of her divine, round orbs.

Tommy looked up and realised he could see a reflection of the two of them in a glass frame. It was a fantastic opportunity to check out her breasts again, this time as he mauled them in his hands.

Janine was impressed. Tommy was like an octopus, his touch was everywhere over her boobs, but it was also light, pleasant, polite, his groping was turning her on, rather than causing her discomfort as was usually the case.

Tommy needed relief, and Janine was just the busty person to provide it. Gently, he urged her forward until she put her arms on her desk and leaned forward over them. He leaned back himself and again got an eyeful of her delectable, tasty-looking buttocks, divided by the flimsy material of her thong.

He reached between them and pulled the string of her thong, pulling it out of her crack, down and to the side. He dove back in with his cock, sliding his sausage through the hotdog buns of her butt cheeks.

It was nothing but a short entree for the main meal he desired now though. He pulled his hips back and probed between her legs with the tip of his cock, seeking the moist sweet spot that would bring him the pleasure he desired.

She was certainly wet, and when his tip found its target, he spread it around, feeling her buttery warmth, before pressing forward, intending to sink deep inside her honeyed snatch.

"Wait!" she exclaimed, and Tommy stopped, poised at the threshold.

She sighed, almost wishing he hadn't listened to her, "You... you have to wear a condom." She went back to shuffling things around in her desk drawer.

At first, he was confused, because he certainly didn't think he had to wear a condom. He'd been inside five women and hadn't worn a condom once in his life, so why did he suddenly have to wear a condom? Then he remembered sex education at school. They had learned all about STIs or sexually transmitted infections, and of course pregnancy. He suddenly came to the realisation that he'd been incredibly irresponsible every time he'd been with a woman. Sure, most of them seemed like they weren't out sleeping around, but he'd never discussed contraception once. He could be on the verge of being a father to five different children to five different mothers. Oh GOD!

Janine scrabbled around in her drawer and finally produced a condom from the depths. In sex ed they'd been shown how to put them on using a cucumber, and then they'd all been given one after the class, but Tommy had been embarrassed and he honestly wasn't sure where it ended up, somewhere in his room he presumed. Some pornos had the male stars wearing them, but they never showed them in packets, or being put on. He looked at the packet in her hand. He'd never even touched one outside of its packaging.

She turned around to face him and sank to her knees in front of him. She tore open the packet and proceeded to roll it onto his cock head, pinching the tip the way the sex education teacher had shown them at school. She then rolled it down the shaft as far as she could.

She giggled, "Extra large, I got them as a joke a while ago, but never thought I'd actually need them. I don't think anything smaller would have fit this monster."