The Bet - Billy's Parents Visit

THE BET - ANN AND WILLIAM VISIT BILLY

Ann and William Jarrett were going to visit their son, Billy, at college. This was their first visit there. He had been home a couple of times, and they had met halfway a couple of times. But this was their first visit at his dorm.

When they arrived, they got a motel room, took their luggage in, freshened up, and called Billy to meet them at the restaurant. While they ate, they caught up on what was going on with each other. They went back to the dorm to see Billy's room.

After the grand tour of the dorm and his room, they sat down to talk. Billy's roommate, Larry, had gone home for the weekend. Billy said something about the baseball game there tonight. It was the season opener and a home game. William said he would love to see and asked Ann if she would like to go. He was a baseball fan, she wasn't. She said, "No, but you two go ahead. I'll just hang out here while you're gone. No use fighting that traffic back to the motel, then back here to get you. My laptop's in the car. I'll get it and keep myself occupied."

Billy and his dad left to walk down to the stadium. Ann went out to get her laptop. She got a Coke from the little fridge, kicked off her shoes, and leaned back against the headboard of Billy's bed to read and answer emails. That done, she started browsing stuff on the internet to kill time.

CHAPTER 2

After about 45 minutes she heard the door opening. She wondered what the guys were doing back so soon, but didn't look up.

Someone said, "Oh. Shit. Who are you?"

Then she looked up and realized it wasn't William and Billy. It was somebody she didn't know. "Oh. Sorry. I'm Billy's mom. Who are you?"

"I'm Larry, Billy's roommate. I'm sorry. I didn't know anyone was here."

Ann had gotten up off the bed. She said, "No problem. It's good to meet you." She held her hand out to shake his hand, and he took it. "Billy said you were gone to see your parents. If I had known you were here, I wouldn't have stayed here. He and his dad went to the game. I was just going to wait here, but I can go."

"No, no. It's fine. My car broke down and I had to get it towed, and get a ride back. Nice to meet you, too. I heard some guys talking on the way up here. They said there was a MILF in the building. But I didn't expect to find her in my room. It's a pleasant surprise."

Ann didn't particularly like that word MILF. But, she was flattered at the same time to be considered one. "I don't care for that word," she said.

"Oh. Sorry. I didn't think. It just popped out. I'm used to talking to a bunch of guys."

Ann smiled. "It's okay. I have a son. I know how guys talk."

Larry said, "Make yourself at home. I can go out for a while and give you privacy. I'll hang with the guys or something."

"No. Don't be silly. This is your place. I'll go to my motel room."

"Really. That's not necessary. You stay here. Make yourself comfortable. Can I get you anything? We don't have much, but there's a commissary real close."

"I'm fine. I got a Coke out of your fridge. Hope that's okay."

"That's fine. Help yourself."

Larry sat in one of the chairs, and Ann sat on the edge of the bed. They talked for a while. Ann found out he was studying electrical engineering, and was from Louisiana. He had gotten about 25 miles when his car broke down.

Ann's phone rang. She looked at it and said, "I'm sorry. I need to take this. But you're fine, it's not private or anything." She answered her phone. As she talked she reclined back against the head of the bed again and stretched her legs out.

Larry took this opportunity to check her out. The guys were right, she is a MILF. She wore a blue dress. Not real short, but about 6 or 8 inches above her knees, showing nice legs. She had either hose or pantyhose on, and black high heels which sat beside the bed where she had kicked them off. Her dress was not real low-cut but showed just a hint of cleavage. It was sleeveless. He had noticed right off that she had big tits. And nice legs. Now he took the time to really take it all in and appreciate how beautiful she was. And the room was filled with the pleasant aroma of her perfume.

Larry saw that she was getting upset as she was talking on the phone. She seemed almost on the verge of tears a couple of times. When she hung up, she was trying not to cry. She sat on the edge of the bed. He got her a roll of toilet paper. They didn't have any tissues. He sat beside her and asked if everything was okay. She said, "It's okay. I don't want to bother you with it. I'll be fine."

"It's okay. Tell me." He put a consoling arm around her shoulders.

She looked at him, paused a few seconds, and said, "My sister said her husband moved out. She's really upset. And I can't be there for her right now."

Larry hugged her from the side. "I'm sorry. I wish there was something I could do. Is she going to be okay?"

"Yeah, she'll be okay. I just wish I was there with her. I think it helps to have someone with you in times like this."

"Absolutely. It always helps to have support."

Ann laid her head on his shoulder and softly wept. After a minute she straightened up and said, "I'm so sorry. I just met you. I shouldn't burden you with this stuff."

"It's fine. We all need a shoulder to cry on sometimes. You can use mine anytime."

"Thank you," Ann said, and hugged him.

CHAPTER 3

Being the hormone driven, horny teenager that he was, Larry was getting excited hugging such a beautiful woman. And he had always had a thing for older women. He started rubbing her back. He put his other hand on her head to hold her head to his shoulder. He felt her silky hair with his fingers, and breathed in the sweet smell of her hair and her perfume.

He didn't know what to say, but tried to console her. "It'll be okay. She'll be okay. You can be there with her when you get home. You're a good sister."

Ann had stopped sniffling, but continued to let herself be hugged. It felt good to be comforted. When she felt calmer she pulled away from Larry, put her hand on top of his on his thigh, and said, "Thank you. That was a big help. I'm so embarrassed. I should keep myself under control better."

Larry turned his hand over to grasp hers. He said, "Nonsense. You controlled yourself very well. You were just upset. We all are sometimes. Don't be sorry. You have nothing to apologize for. But I'm glad I could be here for you."

"You're a very nice young man, Larry. Thank you."

CHAPTER 4

A few minutes later, when Ann was back to normal, Larry said, "I don't know if you do this sort of thing, but when I'm upset about something I like to smoke a bowl. Would you like to?"

"I don't. Not anymore. I used to, but I haven't in over 20 years. But if you want to, go ahead, it's your place."

Larry got a bowl, a baggie of pot, and a lighter out of his nightstand. He sat in the chair, filled the bowl, and lit it. Ann watched him as he toked on it. He thought she looked like she missed it, and wanted to try it again. He got up, sat beside her on the bed, and offered it to her.

She shook her head and said, "I shouldn't."

"Oh. Go ahead. You said you've done it before. You know it won't hurt you. It'll make you feel better."

When he held it out to her again she tentatively took it. She hesitated, then put it to her lips, and gently sucked in. She immediately went into a coughing fit. When she quit coughing she said, "I forgot that part of it."

Larry laughed. "That's the bad part.Just toke a little easier until you get used to it."

She tried again, with better results this time. She held it in a few seconds, then exhaled. It felt good. She coughed a little bit here and there, but was able to take a few tokes successfully. Larry got them both another Coke to help with the cottonmouth, and sat back down beside her.

Larry had put on some music. They sat listening for a few minutes and laughing at pretty much everything. Ann said, "I always loved this song. Me and my friends used to dance to it all the time."

Larry stood up, took her hand, and said, "Come on. Dance with me." He pulled her to her feet.

"I don't know. I haven't danced in 20 years."

"Come on.You don't forget how. It's a slow song, nothing wild." He pulled her to him and put his hand on her lower back. She let herself be pulled in and started swaying to the music.

She put her arms around his waist and laid her head on his shoulder. They danced this way until the song ended. Larry said, "Don't sit down. I'll put on an album we can dance to. You like Bob Seger?"

"One of my favorites."

He started the album and came back to take her in his arms and start dancing. He held her against him enjoying the feel of her breasts pressing into his chest. He let his hand on her back drop lower to the upper swell of her buttocks. When he dropped it a little more she reached around and pulled it up.

When they had danced to another song Larry asked, "How about a few more tokes?"

"Not me, but you go ahead. I'm not used to it. I don't know how it will affect me after all these years."

"You know how you feel now. That's how it will affect you. Do you feel good"?

"Oh yeah, I feel great."

"There you go." He lit the bowl and they passed it back and forth a few times. Then he set it aside and pulled her in to dance some more.

"This is nice," Ann said. "I can't remember the last time I danced. Or felt this good."

"Enjoy." Larry had his hand on her ass now and she hadn't moved it. He gently cupped her buttock on one side. She didn't stop him. Her head was on his shoulder as they slowly swayed to the music. He loved feeling her breasts against his chest. He pressed his now hard penis against her. He thought she was probably pretty high and not aware of what he was doing.

As they continued to slow dance Larry started slowly pulling her dress up in the back, bunching it up in his fingers. She swatted his hand away. He worked a hand between their upper torsos and felt a breast against his fingers. He took it slow. He eventually had his hand where he could feel a nipple against his palm. He gently squeezed. Ann didn't seem to notice. He started trying to get her dress up in the back again. But once again his hand was swatted away.

Ann was enjoying dancing. And being high again after all these years. And, as much as she hated to admit it, she also enjoyed being felt up by a young man. She knew it was wrong, but the attention was nice. She hadn't felt that way since her interlude with Don, her son's friend. And with her own son, but she tried not to think about that. She thought it was probably alright to let Larry feel her breasts a little. Nothing more.

They each took another toke of the pipe, and resumed dancing. Well. not so much dancing as just standing in the middle of the floor swaying. But they were having a good time. Larry fondled Ann's breasts a little more, and pressed his erection into her. She was aware of his hardness and was proud that she still had that effect on young boys.

With Ann's head on his shoulder Larry put his hands on her back again, letting them drop down again. He was able to get her dress pulled up this time. He felt her panty covered ass for a few seconds before she reached around and removed his hand, allowing her dress to drop back into place. He fondled her tits some more and ran his hand up and down her back. He took the tab of the zipper on the back of her dress in his fingers. He started to slowly and gently pull the zipper downwards. It seemed Ann didn't notice. When the zipper reached the bottom Larry waited a few seconds. He pulled back from Ann a little and took the shoulders of her dress in his hands and tried to pull it off of her shoulders. She stopped him and said, "Larry, I think that's far enough." But she didn't zip it back up.

He pulled her close again. He just enjoyed touching the bare skin of her back as they swayed some more. He worked his hand into her dress at the bottom of the zipper. He felt the top of her panties. He worked it a little lower and cupped her panty-clad ass cheek in his palm.

Ann knew she should stop him, but it felt good, and she would stop him before it went any farther than it is now.

Larry kept one hand on her ass under her dress and used his other hand to get between them and feel her tits again. He was really enjoying Billy's mom. He had heard from other guys that had seen pictures of her that she was gorgeous, but he had no idea how gorgeous, or how much fun.

He got his hand inside the top of her dress to cup her tit over her bra. He felt her hard nipple pressing into his palm. He worked his fingers into the top of her bra and tweaked her nipple with his fingertips. He once again brought his hands to her shoulders to pull the dress down. As he drew away to allow enough room to pull it off of her shoulders she didn't resist. She let him slide her dress down her arms and she pulled her hands free.

Larry gazed at her partial nakedness for a few seconds. But he didn't want to take too long or she might change her mind. So he stepped in closer and pulled her face in to kiss her. Her tongue came out to meet and wrestle with his. He had a hand on her tits and alternately fondled one, then the other. When he reached around to unclasp her bra she told him no.He was content to feel her tits through her bra. And feel her panties with the other hand. After a few minutes he went for the bra clasp again. She didn't stop him this time. He unclasped it, slid it off her shoulders, and pulled the straps down her arms and off.

He looked at her tits for a moment. They were the biggest he had ever seen in person. After complimenting her on how beautiful her breasts are, he leaned in to kiss them. He kissed one breast as he squeezed the other, then switched. He took a nipple between his lips and gently suckled. Ann held his head in her hands as he loved her tits.

After a couple minutes of this Larry raised up to lock his lips on hers once again. As they kissed his hands went to her back. He rubbed all over her bare back and let his hands drop to her waist. He started pushing her dress over her hips. Ann came to her senses and stopped him. She said, "Larry, I can't. I'm happily married. Well. Married anyway. That's probably far enough."

"Okay. Whatever you say. I'm not going to force you." He started kissing her again. And rubbing all over her upper body. And fondling her breasts. He kissed her neck, her ears, her forehead. He stood behind her and fondled her breasts while nuzzling her neck and pushing his erection against her ass. He touched her crotch through her dress. She stood still and let him make her feel loved and wanted. She sighed and moaned and let herself get lost in her ecstasy.

He turned her around and began kissing her again. When he reached to push her dress down again she did not stop him. Her dress dropped from her hips and pooled at her feet. Larry started guiding her backwards toward the bed. She lifted her feet one at a time to step out of her dress laying on the floor. When she felt the bed against the back of her legs she sat down. He pushed her back to lay on the bed. He laid on top of her and kissed her.

He kissed her lips, then her neck, then moved down to her upper chest while he fondled her tits. He began kissing all over her tits and belly. When he started sucking her nipples he slid a hand down to feel her pussy through her panties and pantyhose.

Ann stiffened. She knew this had gone way farther than she ever intended to let it. But she thought that maybe they could just get each other off with fingers and hands and let it go at that. So she let him feel her hot pussy through her panties.

Larry raised up on an elbow to gaze at the beautiful older woman he had nearly naked on his bed. He looked at his hand rubbing her hot, wet pussy. He got up and stood beside the bed. Her ass and hips were at the edge of the bed and her feet were on the floor. He lifted her feet and kissed them one at a time. He rubbed her calves. He reached for the waistband of her pantyhose and slowly pulled them down her legs and off.

Her panties were a light gray color with black lace around the waistband and the legs. And what looked like a little black teddy bear off to the side. They covered her pussy completely but he could see a dark patch of hair beneath. And there was a wet spot right where he had been rubbing.

He still had her feet in his hands. He sucked on her toes on each foot. He licked and kissed his way up her legs, one, then the other, stopping when he got to her knees. He slid her back on the bed a little farther. He leaned over and kissed and licked higher on her legs, above her knees. She spread her legs. He kissed the insides of her thighs. She thought, 'Okay. I can go as far as oral.'

He stuck his tongue out and licked around the waistband of her panties. He licked around the leg bands, avoiding her pussy for the moment, wanting to increase her excitement, anticipating when his tongue was going to lick her. She raised her hips, trying to get his mouth to make contact with her anxiously waiting hot pussy.

After what seemed like an eternity he finally kissed the center of her wet, smelly panties. He licked the wetness and breathed in the intoxicating aroma. Ann let out a cry. He loved her through her drenched panties for just a minute, then hooked his fingers in the waistband and slid them down her long beautiful legs. She lifted her hips to help.

Larry got on his knees on the bed between her legs and leaned over to taste her now naked pussy. Her hair was short and neatly trimmed. Just enough to be downy soft and look good. He kissed her right in the center of her lips. She let out a yelp. He lightly licked her swollen lips, then up and down the crease between the lips. Ann continued to writhe and moan and lift her hips toward his mouth.

He inserted a finger into Ann's very wet cunt as he continued to lick her. He lapped at her juices that were lubricating her entrance in preparation of being fucked. When he took her engorged clit between his lips and sucked on it Ann screamed quietly and grabbed his head to force him in tighter. He nibbled on her clit gently with his teeth and she came hard. She couldn't muffle her cries of delight as she felt Larry licking up as much of her juice as he could.

Larry stood up and was undressing while Ann calmed down and caught her breath. When he removed his underwear Ann sat up and took his hard cock in her hand. She stroked him for a minute with her silky smooth soft hand. He stood there watching her. She slid off the bed to her knees and took him into her mouth. Larry's cock was not all that large so she was able to take it all in. She reached up and fondled his balls as she sucked him.

She removed her mouth and ran her tongue all along the length of his shaft, almost putting him over the edge when she licked the sensitive underside. Larry marveled at his good fortune as he gazed down at the goddess sucking his cock. He reached down to squeeze a titty as she put her lips around his dick once again.

When he could stand it no more he told Ann, "I'm going to cum." Knowing she would want to take her mouth away and let him shoot on her face or chest or somewhere. Instead, much to his delight, she kept it in her mouth and swallowed every last drop. When she felt him stop squirting she removed her mouth and licked his cock clean.

Larry lifted her under her armpits to stand and they laid down side by side on the bed. Larry ran his hands all over her exquisite body as they kissed. She did the same. As he fondled and kissed her breasts, and felt her hot, wet, pussy, she massaged his soft dick. He felt himself getting hard again.

He raised up and got on his knees between her legs. He lifted her hips and put a couple of pillows under her. He wanted to be upright so he could see her while he fucked her. He guided his hardness into her. She was wet and ready, but surprisingly tight. He had never fucked a mother before and assumed she would be loose after having a child, but found that not to be true. He slowly stroked his cock in and out, not all the way, watching her. Her eyes were closed, her head moved from side to side, she had a big ole smile, and she sighed, moaned, and let out cries of joy. Larry decided older women were more appreciative.