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!"
