Sex Lessons with Jack

In a typical street in the nicer part of town, sits a row of almost identical well-kept houses. The residents are generally well off retirees or families with high paying jobs and nannies to look after their kids. In the end terrace lives a man who's done very well for himself given that he's only 31.

Jack works in IT. While we was at uni he successfully developed and sold an app to a large corporation, if he wanted to, he'd never have to work again. So he dropped out of uni, bought a nice house and a fancy car and decided to work for himself. He continued to develop software and apps for companies, but was also well known in the local community for helping out with domestic tech problems too. Working from home meant he was always happy to pop round someone's house and install a printer, or unlock a blocked phone.

Jack had a sizeable house and had converted it to be exactly what he wanted. He had a large garage built onto the side of the house. His ground floor had a comfortable living area with a huge TV, a state of the art kitchen and his own personal gym. Upstairs he had a master bedroom with en-suite, a guest bedroom, a large walk in shower room and a sizeable workroom with all the computer equipment he needed to keep the money coming in. He was attractive, with short dark hair and piercing green eyes, average height and a well maintained physique (thanks to his home gym) that wasn't too muscly. He was always well dressed, usually in a shirt and jeans, even at the weekend.

Jack had a beautiful silvery- grey cat that liked to follow him around the house, called Bonnie. That was as much commitment as he was interested in. Jack had no interest at all in a long term relationship. His life was exactly as he wanted it, he couldn't stand the idea of someone coming into his house and trying to change things, or change him.

Of course, that didn't mean that Jack didn't enjoy sex, but he'd found a way to make sure that was never in short supply.

Jacks street was in walking distance of two sixth form schools as well as the college campus. As well as popping into peoples homes to solve their technical issues, occasionally people would call in to his house for help. Jack kept two mobile phones for this reason. One that he gave out to family and neighbours and one he kept for special clients. These special clients were usually between the ages of 18-21, who would call in on their way to or from sixth form or college.

Jack had a reputation among the girls for helping them lose their virginity. This way Jack got the sex he wanted and they got a decent experience for their first time that wasn't going to lead to a relationship. Usually girls that had already been with him passed his number onto other girls in need of his services. They would then text him requesting his special services and he would reply with a date and time.

Today was one such occasion. Jack had been busy that week with various work commitments, so this girl had been waiting almost a week to come and see him. He didn't allow them to randomly come over, that might look suspicious. So he always gave them a time and date that suited him and made it look like he was helping them with a tech problem.

He wiped down his spotless kitchen worktops and checked the time as the doorbell rang. She was 5 minutes early.

He opened the door to the hallway and greeted her like any other client.

"Hi," he smiled, "I'm Jack, why don't you come on in?"

The girl smiled nervously and stepped onto the grey laminate flooring as Jack gently closed the door behind her. "I'm sorry sweetheart, remind me of your name?"

"Oh!" She blushed furiously, "Sorry, it's Rebecca... Becki..."

Jack smiled again, "A pleasure. Now what can I do for you?" He knew full well why she was there but he did enjoy watching them squirm.

"Well, my friend Sarah came to see you a couple of weeks ago... she gave me your number because I have.. uh... well, the same problem..." she was blushing furiously again and struggling to look him in the eye.

"Why don't we go through to the kitchen? Would you like a drink?"

She followed him nervously into the kitchen. She hadn't expected hospitality, she thought they'd get straight to it. She perched on one of the high stools as Jack busied himself around the kitchen.

"Do you drink?" He called over his shoulder.

Becki fiddled nervously with a loose thread on her sleeve.

"Sometimes, what are you having?"

Jack smiled to himself as he sliced cucumber into the glasses in front of him, topping them up with gin.

He turned back to her and held out a glass. She took it cautiously. This definitely wasn't the cheap wine she was used to. She tried not to wince as she took a small sip of the potent drink.

Jack swirled the ice around in the glass. "So Becki, what it is you're looking for today?"

"Well, sex really..." she mumbled, focussing on her drink.

"Don't be embarrassed to say the word sex sweetheart. It's perfectly natural and nothing to be ashamed of. You are a young hot blooded women and there's nothing wrong with wanting sex."

He took a moment to look her over, enjoying the fact that she was still in her sixth form uniform.

"So, what have you done so far?"

"Not a lot. I have a boyfriend and we've kissed and done some touching... only over our clothes though. He really wants sex but I'm so nervous. I just want it to go right. I don't want him to leave me because the sex is bad..."

"Where has he touched you?"

"My breasts but that's it really."

Jack nodded while sipping his drink, checking out her firm breasts through her tight white shirt.

"So do you just want sex? Or do you want to do oral or anal... do you want me to do a bit of everything? What sort of things will your boyfriend want to do with you?"

Becki looked at him blankly and Jack chuckled. "How about we head upstairs and see what happens?"

"Upstairs?" Becki paled.

Jack chuckled again, "To my bedroom? Sex in the kitchen might be fun but it's not ideal for your first time!"

Becki could have kicked herself, he must think she's a complete idiot! She quickly finished the gin and followed him upstairs.

Jack opened his bedroom door and smiled, "Make yourself comfortable."

Becki perched on the edge of the bed, taking in the immaculate room around her. Jack pulled his dark blue sweater over his head and hung it carefully over the back of a plush maroon chair in the corner of the room, before returning to the bed. He sat comfortably against the pillows and patted the bed next to him, signalling her to move closer. She moved awkwardly up the bed, unsure of how she should position herself.

Jack enjoyed being in control. He liked order and routine, which is probably why he preferred younger inexperienced girls. They weren't bossy and controlling, he could do whatever he wanted with them. He placed his hand lightly on her side, feeling the warmth of her skin through her thin blouse.

"I've always liked girls in uniform, but it looks especially good on you." He purred, "You've no idea what pretty girls like you do to men like me..."

Becki blushed, "You think I'm pretty?"

"Of course! Boys must be after you all the time."

"You'd be surprised. I'm not one of the popular girls."

Jack pulled a face as if he didn't believe her. "If at any point you want me to stop, just tell me ok? We'll start with a bit of foreplay, maybe some oral to make sex more comfortable..."

"How will I know what to do?" Becki asked.

"Just do what feels good sweetheart." He smiled as he leaned in to kiss her firmly on her young, tempting lips. She gasped a little as he slipped his tongue into her mouth, but soon fell into a familiar rhythm as if Jack was her boyfriend. They had done plenty of kissing and she started to feel less nervous.

Jack ran his hand slowly over her chest, squeezing her right breast gently as he passed over it. Her breasts were small and pert in his hand, just the right size. He felt himself harden at the thought of her untouched nipple in his mouth. Becki had mirrored his movement and rested her hands on his chest, feeling his tight pecs under his shirt.

Slowly Jack untied her striped school tie and dropped it over the side of the bed, before starting on the buttons of her blouse. He took his time unbuttoning each individual button, still kissing her to keep her distracted. Becki felt her skin prickle as cool air brushed against her skin through the opening in her blouse.

Leaving her blouse on but unbuttoned, Jack slipped his hand inside and cupped her breast through the white lace of her bra. Becki let out a small moan as Jack explored her bare flesh. He slid her blouse off over her shoulders and nudged her onto her back.

He straddled her, his eyes hungry for her bare flesh. He leaned over her and gently kissed the spot below her left ear, starting a trail the led over her shoulder and down to her breasts. Becki fumbled with Jacks shirt buttons and he helped her take it off, still continuing to caress her skin with his lips.

He glanced up at her, his face between her firm breasts. "So, no one's ever taken your delicious looking nipples into their mouth before?"

Becki shook her head, barely breathing. Jack smirked as he tentatively kissed one of her nipples through her bra. Becki gasped, arching her back a little as he moved to the other nipple. As she arched her back, Jack expertly reached underneath her and unclasped her bra, discarding it quickly on the floor. Jack let out a small moan as his lips closed around her firm, pink nipple and sucked gently. While he enjoyed one nipple he used his hand to caress and lightly pinch her other. Without realising it, Becki ran her hands through his hair, silently begging him not to stop. Jack switched to her other nipple, giving it the same attention as the first. Becki moaned again as the cool air reached her now wet nipple after the warmth of Jacks mouth.

She felt a familiar aroused sensation starting between her legs as Jack continued to enjoy her breasts.

He glanced up again, "Is that good sweetheart?" Becki nodded, her eyes closed and her hands still holding his head against her. "I'm going to move down a bit now..."

Becki couldn't reach him as his kisses trailed down her stomach and over her navel, she found herself gripping the bed covers tightly instead.

She lifted her bum up so that Jack could reach under her to unzip her short plaid skirt and pull it off her. Jack breathed in the scent of her arousal, pausing a second to savour it. Instead of tights, Becki had long white, knee high socks on and Jack took his time rolling them off in turn. He stood up, Becki watching nervously as he unbuckled his belt and dropped his dark jeans to the floor. She could see the bulge of his cock straining against his boxer shorts. Her mouth went dry at the realisation he was going to put that inside her.

Jack slipped back onto the bed, him head near her stomach and propped himself up on his elbow. His other hand trailed lightly over her abdomen towards her white lace thong. Becki shivered lightly at his whispering touch as he teased her with his finger tips. "So... I really, really enjoy pussy." Jack growled quietly, as his fingers wandered achingly slowly over the top of her thong and down towards her mound. "I love the sound of a woman when she has her pussy eaten for the first time. When she realises how good it feels to have someone make her cum with just their tongue."

Jack heard Becki let out a shuddering breath as his fingers ran over her thong between her moist lips. She throbbed with desire and need, but he kept the pace slow, holding her on the edge.

"Do you want me to make you cum Becki? Do you want me to suck on your virgin clit until you're howling with pleasure?"

"Yes... now... please... I really need you to..." she whimpered, still fisting the sheets beneath her trembling body. Jack stroked her lazily a little longer until he couldn't wait anymore and whipped off her thong. He ran his hands up the inside of her tanned thighs, slowly parting her legs for him.

He let out a predatory growl of appreciation at the sight of her moist lips. Her pubic hair was light and neatly trimmed and as he nudged her legs a little wider, he saw the glistening entrance of her pussy, waiting to be deflowered by him. Jack breathed in her arousal again before lowering his head, placing a light kiss on her tight opening. He heard Becki yelp in surprise as he suddenly ran his tongue along the inside of her lips. She had never experienced anything like this before. She had masterbated a little in the past, but it wasn't amazing. This on the other hand, was something else.

After sex, giving oral was top of Jacks list of things he enjoyed. He knew a lot of men didn't like it, but how could you not enjoy the sense of power that came with it? You could make a woman explode with just your tongue and a bit of effort. He found virgins even more enjoyable as they had no idea what to expect, usually came hard and made a lot of noise as they enjoyed it. He liked having his hard work appreciated.

He focussed on Becki's delicious pussy lips as his tongue explored every inch that was open to him. Her legs were open wide as she gave him access to her most intimate areas. As he moved up to suckle her throbbing clit, she cried out, her skin flushing uncontrollably.

"You like that sweetheart?" He breathed against her, "You make all the noise you want to..." She groaned again as returned his attention to her clit.

Now she was dripping wet, Jack positioned two fingers at the entrance to her pussy, stroking gently as he worked on her with his tongue. Becki was breathing heavily as his fingers slipped inside, working her in a steady rhythm as his tongue continued to drive up the incredible feeling building inside of her.

Becki arched her back, letting out a loud squeal as she came hard against his face, Jack continuing to work on her with his tongue as he greedily lapped up her precious juices. Becki laid back, panting hard as Jack sat up and wiped his mouth with the back of his hand.

"I think you're wet enough to take me inside you. Would you like that now Becki? Would you like me to fuck you now?"

Becki whimpered, "Yes. I want you to fuck me."

"Good girl." He smirked, "It is going to hurt a little, but it's worth it."

Jack pushed his boxer shorts off, freeing his hard cock before stroking it firmly with his hand. Becki watched anxiously as Jack positioned himself between her slick thighs, rubbing the tip of his shaft against her opening. She whimpered again. She wanted him to make her cum again. She needed him to.

Jack groaned at the resistance from her tight pussy. Another reason he enjoyed virgins, nothing compared to a tight unfucked pussy wrapped around his cock.

Becki let out a squeal of discomfort that Jack ignored as he pushed his way in further. Once he was in as deep as he could go he paused, letting her adjust to his size. "Relax sweetheart, it'll hurt less." He whispered as he ran his hands over her breasts again. Becki let out a breath and tried to relax, ignoring the sharp stretching pain inside of her.

Jack eased out part way before sliding back in, again and again until she was relaxed and wet. She started to moan, giving herself to him fully as he worked in and out of her. Jack watched as her skin flushed again as his rhythm built. Instinctively she reached for his hips, holding him against her as he fucked her faster. "Is that good sweetheart? I want to hear how much you're enjoying being fucked, then I'm gunna shoot a load of cum in your tight little pussy..."

Becki was embarrassed, but she couldn't stop herself from moaning loudly with each of Jacks thrusts.

"Shit you're so tight." He groaned, closing his eyes as he rode her hard. He felt her contract against him as she let out the most erotic moan Jack had ever heard. He felt his balls tighten as he grunted, pumping his thick cum deep inside her.

Jack pulled out and collapsed onto the bed next to her, glancing at the pink tinged moisture on his cock where she'd bled a little.

"So, you have two choices Becki. We can stop there, I gave you what you came here for... or, I can show you a couple of other things?"

"Like what?"

Jack smirked to himself, he knew she wouldn't say no. "Well sweetheart, if you really want to make your boyfriend happy, you can't go wrong with doggy style. Men can't get enough of that. Then there's one last thing you'll need to be able to do well if you don't want to end up single forever..."

"What's that? If the other girls know about it then I want to."

"Good girl..." he smiled, placing a lingering kiss on her lips. She pushed her lips against his, desperate for a repeat of the last orgasm he'd given to her. He ran his hands over her firm tanned skin.

"Get on your hands and knees..." Jack breathed against her lips. Surprised by his request, she sat up and turned over, steadying herself on all fours. Jack knelt behind her and stroked her pert ass cheeks, kneading them gently as he lined his cock up behind her.

Becki cried out as he entered her roughly from behind. She was sore from last time and her pussy stung a little from being so stretched out, but she soon found herself moaning again as he built up a rhythm inside her.

Jack grabbed hold of her hips as he fucked her roughly from behind, enjoying the sight of her puckered asshole as he ground into her wet pussy. He grunted happily as his balls slapped against her. Jack reached forward and fondled her breasts as he felt himself coming close again.

"Do you like it rough sweetheart? There's nothing like a good hard fuck... if you really like it rough, there's always anal?"

"No!" Becki squeaked, "Not that!"

Jack chuckled, "Your loss..."

He drove himself deep inside her, over and over until she cried out and he filled her for a second time. She fell forward exhausted, sweat glistening on her back as Jack caressed her ass cheeks one last time.

"Before you go, I suggest you come and shower with me and I'll show you that last thing that men can't get enough of..." suggested Jack as he stood at the side of the bed. Becki nodded, unsure if her wobbly legs would support her. She slipped off the other side of the bed and winced as she glanced at the spots of blood on the sheets. Jack followed her gaze and shrugged, "You're not the first and you won't be the last."

She followed him into the walk in shower, gazing at the beautiful simplicity of the slate tiles all around her. Jack flicked on the water from the large shower head above them and picked up an expensive looking bottle of shower gel from a small recessed shelf in the wall. He squirted some into his hands and beckoned her towards him. Becki moves towards him slowly, unsure of what he was about to do. Jack smiled, "Relax, I just thought we should clean up."

Becki let out a relieved breath and relaxed as his soapy hands covered her whole body gently. She moved to kiss him as she followed his lead and helped to lather him up.

As he worked the soap between her legs she slipped her foamy hand around his hardening cock. Jack let out a soft moan against her lips as she started stroking his shaft. "Let's get this soap off and I'll show you one last thing."

Becki stepped back and let go of his cock as the hot water ran over them both, washing the soap away.

"Now, on your knees again." Jack commanded. Becki obeyed quickly, keen to learn the last thing that men love.

"Good girl. Now... suck my cock."

Becki glanced at him, "What do I do?"

Jack smirked, "Trust me sweetheart, you can't really go wrong."

Becki moves towards him on her knees and reached out her hand for his cock. Tentatively, she touched her pink tongue to the tip of his cock. She looked up to find Jack closing his eyes and bracing himself against the wall behind him.