Jill's Deflowering

Characters are over 18.

This story is fictional, and some things are sexy in fiction but not in real life and rape is one of them. Please treat the women in your life with respect. Get consent.

*****

Jill was scared, but she didn't want to go back now that she had spent so long on her plan. It was her friend Sarah who had started it really, telling her all about her experiences. Sarah had gotten fingered by one of the boys and school and told Jill about it so much that Jill hadn't been able to contain her curiosity. But Jill didn't want any of the high school boys - she wanted a man. And not just any man, one she'd had a crush on for a long time. His name was Ray but she usually called him Mr. Peterson. She babysat his two sons, and ever since she had laid eyes on him he had given her butterflies. He was divorced from his wife, so it wasn't cheating for her to do things with him.

With encouragement from Sarah she had started to flirt with him. She wore shorter dresses to babysit the children, and when he was home she always bent over to give him a peek at her backside. She thought it must have an effect on him as he often licked his lips and had started to watch her body more closely all the time.

Jill didn't really know how to take the next step, but Ray took care of it for her. One evening he called asking her to come over and babysit the boys. Jill drove over and knocked on the door, adjusting her short silky dress as she waited. Ray opened the door and gestured her inside.

"Good evening, Mr. Peterson." she greeted him politely

"Thank you for coming on such short notice, Jill." he replied, closing the door behind her.

"Where are the boys?" Jill asked after scanning the room and noticing the silence.

"They're at their mother's this weekend." Ray said, as he laid his hands on Jill's waist from behind. She spun to face him and he pressed his mouth firmly down against hers.

Jill was taken by surprise and felt her whole body stiffen, but Ray was not deterred. His tongue fought its way into her mouth and began to probe around. One hand held the back of her head, but the other wandered over her body; first to the small of her back, then down to give her ass a squeeze, then up to her small breasts. She wanted to protest, but Ray's hungry mouth was covering hers, and besides, what could she say? This was what she had been trying to make happen, wasn't it? She tried to relax into it. Sarah said it would be amazing, so she should just enjoy it.

Jill gasped with surprise as Ray scooped her up in his muscular arms. He was stronger than she had realised; she felt like a ragdoll in his grip. He carried her to the next room and laid her on the couch. Immediately, his mouth was back on hers, but his hands became more insistent now. He pushed the straps of her dress down off of her shoulders and let the fabric fall to her lap. And then with one hand he reached around her back, unhooking her bra while the other caressed her.

As her bra fell away, he broke off their kiss to take her breasts in with his eyes. Her small pink nipples were soft and delicate-looking, with a little dot of shine where the light caught them. He smoothed his thumb across the tip of a nipple and Jill squirmed. Just a little, but he noticed and grinned. The next thing she knew, his mouth closed over one of her nipples, and his hand began insistently working the other. He rolled and pinched her nipple between thumb and forefinger. It hurt a little, making Jill scrunch up her face, but it also felt good. She felt a familiar tingling between her legs. When Ray pulled his mouth away, her nipples stood stiff, even smaller than before.

Now Ray began to kiss his way down her stomach, slowly. Jill's heart began to pound when she realised where he was headed. He pulled her dress all the way down her body, lifting her hips to slip the dress off. And then he kissed his way up her thigh to her panty-covered pussy. Her panties were a pale pink, simple, but they matched her nipples, which made Ray stiffen even more. He pulled them aside gently to reveal her pink slit, shiny with moisture. He liked that Jill had shaved her lips, but left the soft hair above her mound untouched.

He was aching with desire by now, so he didn't wait to pull her panties down her legs too. Jill had never felt so exposed in her life, lying naked on a man's couch while his eyes drank her in. It didn't help that he was fully clothed.

Ray took one of the couch pillows and tucked it underneath Jill's hips, lifting up and exposing her pussy even more. Ray knew that it would make it easier to get into her, especially if she struggled. And then he descended on her with his mouth, swirling his tongue in circles and flicking it across her clit. Ray had an experienced tongue, and soon Jill was wriggling with pleasure. He has been married, Jill thought, so it makes sense that he knows how to have sex, but I never thought it would be so good!

Ray slipped a thick finger into her, finding her well lubricated for him. Jill was fit to burst with excitement. Now he's fingering me, she thought, I'm no longer a virgin! When Ray went to insert a second finger, he found it took some force to get it past her lips.

"Jesus you're tight!"

"Is that... is that bad?" Jill asked, extremely insecure, and feeling an unpleasant stretching inside her from the intrusion.

Ray laughed "Not for me, it ain't!"

Ray began to move the fingers in and out of her, only slowly so she would have time to adjust. Even so, Jill was cringing as she stretched. Ray continued to move his tongue over her clit, and soon he felt Jill responding. Her hips started to rock, and her toes clenched. As her orgasm built, Ray felt Jill's pussy muscles clenching. He gave her clit a sharp smack that made her yelp.

"Don't tighten your muscles. Relax, or I'll never get in you later."

Jill didn't seem to understand. "But you are in... there, aren't you?"

Ray would have laughed, except her innocence was too arousing. She had no idea what was coming next, she thought she was being fucked now!

"You're in for a surprise in a moment sweet, but now just enjoy this." He put his mouth back to her clit, working it furiously with his tongue.

Jill's mind was reeling and she had a bad feeling about what he had said, but she couldn't think straight with what he was doing to her. With his fingers moving ever so slowly inside her and his mouth working on her clit, she was soon rocked with an orgasm. Her whole body shook and she moaned with the pleasure of it.

As she came down from her orgasm, Jill slumped back and closed her eyes. She was trying to slow her breathing. Ray took this as his chance and he moved off of her and began to remove his own clothing.

He stood naked over her, his large cock straining. He wasn't sure if he'd ever been this hard, knowing that he was about to deflower this beautiful girl.

He kneeled down over her, one knee on either side of her little body, and when she opened her eyes, his cock was jutting towards her face. Jill's eyes went as large as saucers. "I..." Jill began to protest but was too shocked to know what to say. Sarah had never mentioned this part. And his... it was so big!

"Come on now, it's only fair that you please me now, isn't it? After all of that I thought you would be grateful."

"I am! I just... I don't know how."

"I'll show you, don't worry. Just open up and keep your teeth to yourself."

Reluctantly, Jill did as he said and took the tip of his cock into her mouth.

"That's it, now move your tongue. That's a good girl. Now let me in a little deeper."

He pushed himself further into her mouth and heard her gag almost immediately. She spluttered and pulled away from him.

"I'm really sorry, Mr. Peterson, but I don't like this." she said in a small voice "I... I don't want to be ungrateful, but it won't fit."

"It's okay Jill, I understand. There's something even better I can do. And you just need to lay back and relax."

Relieved, Jill laid back against the couch as he kissed his way back down her stomach again. She was still satisfied from her orgasm, but if he wanted to do it again, she wouldn't argue.

When he got to her pussy, he licked all around her slit, getting her good and wet. As tight as she was, he wanted to make sure she wouldn't tear. He moved himself into position against her upwards-tilted hips. One hand laid on Jill's chest, half so he could play with his nipple, and half to hold her down if need be. The other hand guided his cock to her opening. He began to press himself into her, but made no progress into her before Jill snapped her head up and saw what was about to happen.

"What? No, that will never fit!" She yelped, afraid

"It will sweetheart, don't worry. I'll go slow. You'll enjoy it before the end."

Heart pounding, Jill knew she couldn't resist him. After all, he did make her feel very good, she owed him this much. With one hand he pressed her back down against the pillows, while the other moved to her little clit. He pushed into her again, this time getting past her lips. Jill gasped and her hips jerked back, pulling him back out of her.

"Silly girl, look what you've done." he scolded.

"I'm sorry. It just hurt so much."

"And now I'll have to do it again - does that make it better?"

She shook her head.

"I didn't think so. You won't do that again will you?" He moved his hands to her hips just in case. He had half a mind to take her in one stroke. He was sure her scream would be sweet and girlish, and that breaking her that way would help her to remember this special moment forever. But despite her squirming, he didn't want to punish her, and he knew even moving slowly he would hurt her.

He pressed himself into her again. This time he got past her lips and another inch. He waited a moment before pushing deeper. Jill was struggling against his hands now, her hips moving to evade him. She desperately wanted him to take it out of her, but he wouldn't. The stretching feeling only got worse the deeper in her went, every muscle in her virgin pussy straining and stretching.

As he pushed a little deeper, he found a barrier. At first he thought it might be her cervix, but he was nowhere near deep enough for that. He decided it must be her hymen, which aroused him greatly. His wife, although a virgin when they met, had never had a hymen, so this would be a first time for him.

He couldn't hold himself back any longer, so he pulled back out until just the tip of his cock was in her. Grabbing her hips firmly, he thrust himself forward with all his strength. Jill screamed as he had hoped she would, and he felt himself break through her hymen, though he still hadn't managed to get hilt-deep inside of her. With her hips to grip onto, he pushed himself deeper into her. Her muscles were so tight all around him, it felt incredible. Finally he felt himself bump her cervix, though he still had a little length to go.

He pulled out to just his tip again, rapidly enough that Jill gasped, then thrust himself in again. This time he hit her cervix on the thrust and she yelped. She had never felt anything like this, it felt like he was thrusting all the way to her stomach. The dull thud when he hit deep inside of her ached.

He began to hammer into her, knowing he couldn't last much longer. Nevertheless, as he has promised, before he came, Jill had started to enjoy it. Her juices were gleaming on his cock and running onto the couch, and each thrust began to elicit a moan from Jill rather than a yelp.

Ray slammed into her one last time, and spent his seed right against the door to her womb. Somehow he liked the thought that he could get this innocent little girl pregnant. After he pulled out, he kept her hips tilted to keep his seed inside her. With his tongue he helped Jill to her second orgasm, her stretched pussy gaping.

Afterwards, he helped her to dress before showing her out the door, and Jill drove home in a trance, having gotten much more than she had bargained for.

-