Exploring Bases with The Babysitter

Babysitting for Josh and Kathy had been more lucrative than any of her other sitting gigs, they called at least twice a week and sometimes as many as five times. Josh worked away a lot and Kathy was a baker who often worked night shifts. They were thrilled when they found a sensible and dependable girl to help. The only problem was, it was seriously affecting her love-life, or total lack there-of.

At twenty-one she had been a late bloomer, in fact it had only been in the past few months she had started getting attention from guys. She had kissed a few guys, but that was it, she had never gotten near second base and she was beginning to think she never would. Being a virgin at twenty-one was not something she was happy about! She had meant to be on a date but Kathy called in a panic, she was on night duty and Josh had been held up at a site meeting, and wouldn't be home till eleven pm.

The kids were asleep by the time she arrived at eight twenty-five, "You are an absolute life-saver Jen!" Kathy said with a quick hug before running out the door. "There's food, bla bla, you know the drill!"

"Have a good night at work!" Jen replied with a smile.

She settled on the couch and decided not to watch tv but instead to get through some of the book she had to read for her Lit class. The End of The Affair by Graham Greene had been an unexpected hit in that semester's reading list, she was sure she would hate it but was drawn in almost immediately. The book was set during WWII in London, and focused on a doomed love affair, she pulled the fluffy blanket from the back of the couch and lay down to read.

She came to a scene that caused a tingle between her legs, the main characters were going to have sex and were making their way upstairs, his hand rubbing her sex over her clothes. It was so subtly sexy. She tried to resist but couldn't and slid a hand under the waistband of her jeans and knickers, quickly finding her throbbing clitoris. She closed her eyes, imagining the hands of a man on her, her fingers strummed hard on her little swollen nub. She was not teasing, she needed to come and was rubbing in earnest.

"Hey Jen I... uh... shit..." The voice felt like a gun-shot, she pulled her hand away and jumped up to find Josh standing in the doorway, hours early and very red-faced.

She burst into tears, racked with sobs, trying to grab her stuff, she just wanted to get out of there.

"I'm... sorry... I... I..." She couldn't form the words, sobbing her heart out.

Josh walked across the room and put his arms around her, pulling her close, "Hey it's ok, please don't cry." He said as he rubbed a comforting hand on her hair, "It's ok, it's ok." He repeated.

It took a few minutes but Josh's words worked, she was calming. He led her back to the couch and sat her down, she put her head in her hands, unable to meet his eye.

"Josh I am so very sorry. I was reading this book and... I've never done that before when I babysat, I dunno what came over me..." She trailed off.

"Don't worry, it happens..." He replied.

"I'm mortified, I could die of shame right now!" She said, sneaking a sideways glance at him before quickly burying her head in her hands.

"Listen, it was a bit of a shock and it would probably be best if you didn't do it when you're babysitting, in case one of the kids were to wake and come down. But it's not the end of the world, do you know how many times I've been caught?" He asked, reaching an arm around her shoulder, physically reassuring her.

"You've been caught?" She asked, looking back up at him.

"When I was at college, I got caught by my roommate, more than once, my coach caught me in the shower after a game... you don't need to feel embarrassed." He answered with a smile, rubbing his hand on her shoulder.

"Thank you for being so kind about it." She smiled weakly. "I'm sure you want to rip your eyeballs out." She added, trying to lighten things.

"Uh no, on the contrary, I'm kinda sorry I opened my big mouth before I saw what you were doing!" He said, grinning, causing Jen's face to redden again.

"You'd have watched?" She asked in a barely audible whisper, her pussy throbbed in reaction to his words.

"I probably shouldn't admit to that, but fuck yes. That's the hottest thing I've seen in... years!" He let his finger trail from her shoulder to her collarbone and back.

"You're just saying that to make me feel better!" She said.

"There's a tent in my trousers to prove I'm telling the truth!" He glanced down towards his crotch and her eyes followed, settling on his erection.

"I've never been this close to an erection before." The words were out of her mouth before she could stop them.

"What?" He exclaimed, clearly shocked.

"I can't believe I just said that, honestly, I don't know what has come over me." The blush was now extending to her neck and ears.

"Jen, are you a virgin?" Josh asked cautiously.

"Yep, never even been to second base." Her answer was more candid than she had intended.

"No wonder you... well, you must be really horny!" His hand explored her arm as he spoke.

"Yeah, I think you've seen just how horny I am." Her tone was lighter than it had been and he wondered if she was flirting with him.

"Have you been saving yourself?" He asked, his cock straining against his pants.

"Not really, I guess I was holding out for someone who knew what they were doing... but then it just never happened and now I'm twenty-one and it's just embarrassing now." She looked away.

He took her chin and lifted it so she was looking at him again. "You are a very beautiful girl, you have no idea how many men would dream of being with you, of taking your virginity." He watched intently, looking for any sign she wanted him to push further. She put a hand on his thigh.

"Thanks Josh, that's really kind of you." She cooed, gazing up at him.

He leaned down and kissed her very softly, moving from her lips to her neck and eliciting an immediate response. Her breath ragged, she moaned a low expression of pleasure.

"Why don't we go upstairs and I can show you some of the bases?" He asked hopefully. "We don't have to do everything all at once." He added, not wanting to spook her; he was desperate to be the one who took this beautiful young woman's virginity.

"I'd like that." She whispered, trembling. She had never been so turned on.

He stood and took her hand, pulling her to her feet, towering over her. He led her slowly through his home to the guest bedroom. As soon as the door closed behind them he was on her, kissing her hard, pushing himself into her.

"Have you ever touched a cock before?" He asked.

"No, I've never even seen one in person." She replied. "I want to though, can I touch yours'?"

"I'd like that a lot, shall I undress?" He took her hand and rubbed it on his clothes boner.

"Yes, should I undress too?" She asked expectantly as he immediately began peeling off his clothes.

"I would love to see your body!" He replied as he slid his boxer shorts off.

He climbed onto the bed and watched as she pulled her t-shirt over her head, revealing a plain white bra supporting her perfect shapely boobs. It was all he could do not to yank at himself when she undid the bra and set it aside. Her tits were a marvel, big but pert with big pink Areolae. She was lean without being skinny, a small waist accentuated by wide hips and a flat stomach. As she pushed her jeans to the ground and stepped out of them, he got his first look at her legs, long, lean and tanned. He longed to have them wrapped around him! Her knickers were a plain, white match to the already discarded bra.

"Come over onto the bed." He said, and she complied.

The sight of her crawling up the bed towards him was almost enough to make him lose it.

"You are so beautiful!" He said through kisses as she reached him.

He took her in his arms and easily lifted her, setting her on her back, he used his knees to push her legs apart. He laid between her legs, letting his hard cock rest against her knickers, feeling the heat from her pussy. He leaned in and kissed her, their bodies totally connected, and gently started to buck against her. She kissed him back with vigour and moaned into his kiss as he humped her.

"So this is technically first base, albeit with fewer clothes, second base is hands, would you like to go to second base?" He asked in between kisses.

"Yes" She panted.

He climbed off and lay down beside her, scooping her up so his arm was around her shoulders, he leaned in and kissed her, her face in his free hand. He let his hand trail down across her jawline, down her neck to her breasts, he explored both while continuing to lavish her with kisses. He let his hand trail down over the soft skin of her stomach and down over her knickers, teasing her by rubbing her over the fabric; she gasped in pleasure. He pushed his hand under the elastic of her knickers and across the soft, smooth skin of her mons; surprised to find her hairless. He parted her lip and rubbed the length of her, she cried out as he grazed her clitoris.

"Oh my god..." She gasped as he pushed a finger inside her tight hole.

He gently fingered her and used his thumb to rub her clitoris, she was writhing in his arms, panting and barely containing her cries. She was very wet and very responsive to his every move. He loved how tight she felt, even on his finger!

"While I do this, take my cock in your hand, rub up and down." His breath heavy and fast, it was all he could do not to explode as her small hand took his cock. He could tell they were both very close to explosive orgasms.

The addition of a second finger sealed the deal and she came hard, her pussy clamping hard on his fingers as she cried out. Feeling the tight grip of her pussy sent him over the edge and he erupted as she pumped his cock.

"Oh shit!" She cried as his cum shot all over her hand and stomach. "I didn't know it would come out like that!"

"It doesn't always come that hard, you made me hornier than ever!" He answered, kissing her.

Josh got up and fetched some towels and helped her clean up.

"Would you like to stop there, or would you like to see what third base is like?" He asked hopefully.

"I can't imagine anything feeling as good as that, but I wanna find out!"

"Do you know what third base is?" He asked.

"Uh not really, a blow job I guess?" She was unsure.

"Not exactly, baby." He purred, crawling between her legs and peeling off her knickers.

"That's part of it, but we can save that for another day."

He kissed his way down her body, paying special attention to anywhere that made her moan. When he parted her lips and thrust his face between her folds she tensed up. "You don't have to do that, it must be gross." She said.

"It's not gross, it's delicious, you're delicious." He answered and dove back in, "Honey relax and don't think about it, just feel it. This is the most natural thing in the world." He said feeling her nerves.

He explored her with his tongue, lapping hungrily at her but it wasn't till his tongue found her clitoris did her body relax, a long moan escaping her. He licked, flicked and circled her clit before sucking on it with a gentle force that dissolved her and sent her crashing into another shattering orgasm.

It took a few minutes for her breathing to settle, he took her in his arms and cuddled her, petting at her.

"Did you enjoy that baby?" He asked when he thought she was back down to earth.

"Oh my goodness... Josh, I have never felt anything so good in my whole life!" She panted. "Are you going to fuck me now?"

"I was hoping you'd say that!" He said, grinning. "Are you sure?"

"I'm sure, I want you to put it in me." She whispered, blushing.

He once again crawled between her legs and lined his rock hard cock to her virgin cunt, dipping the head in a little and rubbing it along her slit to lubricate himself. "I'm going to go very slow until you are used to it, if it's really sore just tell me and we can slow down more; OK?" She just nodded, wide-eyed.

He lay down on his elbows and pulled her legs up so her knees were bent, and very delicately pushed inside her, once the head was in he stopped, rocking slightly. Every cell in his body was urging him to bury himself in her but he wanted her to enjoy this. After a minute he pushed in an inch farther, he had never felt anything like it; she was vice-tight. Incredible. He started to thrust gently in and out with about a third of his length. Her body was relaxing and she was starting to moan and writhe around. When he felt her hands on his arse, he knew she was ready for a bit more and thrust in an inch deeper, she cried out in pleasure. He thrust again, and their bodies met as he bottomed out. He kept still for a few seconds, "Are you OK?" He panted.

"Yeah, it's a little sore but it feels so good." She was really writhing now.

He kept his cock buried but started grinding into her, she was getting really vocal, moaning and panting. All control was lost and Josh pulled his cock almost all the way out and pushed it in until their bodies touched again. She almost screamed; he had to put a hand over her mouth. He started to pump at a steady pace, he knew he wouldn't last long, her pussy felt incredible as it clamped his member.

"Can you go faster, I think it's gonna happen again!" She said, pulling his hand from her mouth.

It was all he needed to hear. He started pumping into her at pace and seeing she was so close to coming; he thrust as hard and fast as he could. It didn't take long of his hard fucking before she bit down on the hand over her mouth and shuddered as an orgasm ripped through her. Her pussy spasmed hard, gripping his cock so tightly that he exploded, pumping rope after rope of hot cum deep inside her. He could barely breathe, both of them panting hard, his cock still buried ball-deep in her; he collapsed onto her. Spent.

It took several minutes for them to decouple; he slumped beside her, still lying half on her.

"Are you ok? Was it ok?" He asked, cupping her face in his hand.

"Baby!" She grabbed him and kissed him deeply.

"If I'm caught late again tomorrow, would you be up for learning some more new techniques?" He was hoping beyond hope.

"I can't think of anything I'd like more!"

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