The Bet - Cover

The Bet

Copyright© 2005 by FreeJack

Chapter 4

Erotica Sex Story: Chapter 4 - Cassie bets she can seduce Jack's mother. Will she come through?

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Reluctant   Lesbian   Oral Sex   Masturbation   Squirting   Exhibitionism   Voyeurism  

"You want me to do what?" I asked, thinking I couldn't have possibly heard her right.

"You heard me," Cassie replied, quickly dispelling that notion, "I want you to seduce my mom."

I looked at her amazed. I really hadn't seen this one coming. "Are you serious?" I asked.

"Yeah, I'm serious," she answered, "I want you to seduce her, I want you to fuck the shit out of her, and then I want you to come back here and tell me all about it."

I continued to stare at her dumbfounded. The idea of me fucking her mom was... well, I didn't know what it was. It was new, that's for sure. We are completely (okay, almost completely) open with one another about our sexual fantasies, and have talked openly about who we would like to have sex with, be it a real possibility or just pure fantasy(in fact, that's how this whole thing got started, with my fantasy of fucking my mom, which Cassie set out to make come true), but through all the people we've discussed, her mom's name never came up. Now she had the opportunity to make me do anything, or anyone, she wanted, and this is what she came up with. Interesting.

I thought about her mom for a second, wondering suddenly why her name never had come up before, when so many others had. It wasn't the taboo of incest, that's for sure. We both actively enjoyed erotic stories about incest, and had speculated more than once about members of our own families — my mom(obviously) and my aunt, her older brother and a couple of her cousins. And it's not like her mom was a bad looking woman. Obviously, she shared some of her daughter's good looks; but whereas my mother was still only 38 and single, Cassie's mom was in her mid-forties and had been a married housewife for twentysome years. Over time, she had let her body slip a little. I wouldn't call her fat, but she definitely had some extra pounds on her — although much of it was in the right places, her tits and her ass. All in all, not the typical woman I would think of having sex with, but it was Cassie's mom and the perversion of that made the idea quite intriguing, after all.

Cassie was looking at me expectantly, and I realized that I was supposed to have some kind of answer or something. "I, uh... your mom?" I asked again, just to make sure.

"Yes. My. Mom." she replied slowly, as if I were retarded. "I want you to seduce my mom. Just like I seduced your mom. I want you to fuck her and do all kinds of dirty things to her, just like I did to your mom. Now do you understand?"

"Yeah, it's just that..."

"Just that what?" she asked, raising one eyebrow like she had a way of doing. "Don't you try to get outta this. I won the bet, fair and square. Now you have to pay up."

Wow, she really did want me to do this. I was starting to get turned on by the idea, but I had just one reservation. "What about your dad?"

"What about him?" she laughed. "You could probably do it while he's at home in the other room. He wouldn't care. My parents haven't slept together in years, they don't even share a room. From what my mom tells me, he lost his sex drive a long time ago. In fact, he'd probably be grateful for keeping her from bugging him."

"Really," I said. Well, who knew. I guess I should pay more attention when she's talking about family stuff.

"Yup. So, now are you ready to accept the terms of my payment?"

I couldn't see any way out of it. And now that the thought had been planted, well, it was already starting to take off in my mind. Who knows, if I was successful, maybe in time there'd come a day when both of us would be fucking each other's mother, or maybe even our own mothers, at the same time. Now that would be something.

"Okay," I said, "I accept."

"Good," she purred, "Now let's go to bed, and you can tell me all about the nasty things that you're gonna do to my sweet old mom."

Cassie woke up the next morning pleasantly sore from all the sex the day before. She wanted nothing more than to remain cuddled up in bed all morning, but it was Monday, and that meant the gym. She got up, got dressed in her work-out gear and headed for the gym, leaving Jack still softly snoring in bed.

The gym was a couple miles away, so she had to drive there, but it was small and rarely busy, and that's why she liked it. Today was no exception, there only being four or five other people inside, and she went about her normal routine without anyone bothering her. She did a half hour of cardio, then moved on to weights. Some of the others had finished up, and now it was just her and two older guys, most likely retired and with nothing else to do, left. She was halfway through her second set of arm-curls when another girl, or should she say young woman, for she guessed her to be about 27 or 28, entered and took up one of the treadmills. She had seen the woman a couple times before, but had never really spoken to her before other than to say 'hello'.

For some reason, Cassie found herself watching her. She was quite pretty, with thick dark hair pulled back in a ponytail, and a nice shapely ass. She had a bit of a stomach, although you couldn't tell from a casual glance, and nice full breasts that bounced enticingly as she began to pick up speed on the treadmill. Cassie wasn't sure why, but for some reason she got the distinct feeling that the woman was a relatively new mother, and here at the gym to work off the last of her pregnancy weight.

Cassie kept watching her on and off, trying not to be too obvious as she continued to do her reps. She finished her arm-curls and moved on to the next machine, placing her now almost directly behind the woman. Now she could watch with impunity, and she found her eyes locking onto that ass every time she looked up.

And what an ass it was, framed beautifully by the tight spandex shorts that clung snugly to its curves. Cassie began wondering what it would look like naked; she bet it would be perfect and smooth, with just a scarce dusting of delicate dark hair circling her anus. She thought about how it would feel, those firm white cheeks cupped in her hands, and pictured herself lowering her face down into that spread cleft, inhaling deeply of her musky scent, her tongue eagerly lapping at the girl's sweet nectar. As she watched, she could see a dark sweat stain beginning to form at the base of the woman's crack, and her twisted mind quickly had her thinking about licking that dark valley clean too.

She suddenly realized how aroused she had become, her pussy was wet and weeping into her panties, and it was all she could do to not touch herself. She squirmed about on her seat, seeking some relief but finding none. She couldn't get those thoughts out of her mind, and every time she looked up, there was that ass — beckoning to her. She wanted to go to the woman and grab her, to seduce her, to beg and plead with her, anything... to be able to be intimate with her right now. But she knew she couldn't, she didn't even know her name, she couldn't approach her like this, out of nowhere. She would have to come up with a plan, just like she had with Jack's mom. But for now, she had to get out of here.

She put down her weights, her set unfinished, and headed for the locker-room. There she quickly stripped down and ducked into the shower, hoping the water would cool her down — in more ways than one. Normally, she went straight home after her workout and showered there, but today she was going to make an exception. She adjusted the water temperature and began to lather up. She was tempted to pleasure herself right here, right now, while she was already worked up and the vision of that ass was fresh in her mind, but she would just die if someone were to come in and catch her.

Besides, she needed her pussy licked really, really bad, and since Jack was sure to be gone to work by now, she had just the person for the job. His mom's workplace was only two blocks from here; and by Cassie's estimation, it had to be just about her lunchtime.

"Hi, Cin. What's up?"

Cindy jumped unexpectedly at the sound of Cassie's voice, and nearly knocked over everything on her desk. She worked as a real estate agent for a mid-sized firm, making decent money but nothing special. But she did have her own desk.

"Oh, Cassie! Jesus Christ, I didn't hear you come in," she said, gathering her composure, "What are you doing here?" She tried to make it sound off-hand, but it came out kind of forced and almost accusatory, and her cheeks had already turned a bright red.

Cassie smiled, pleased. Apparently, Cindy remembered yesterday, and if Cassie's presence alone had this much effect on her, then there was no way Cassie was going home without having her needs tended to. "I was in the neighborhood, so I thought I would stop by and take you to lunch. My treat."

"Umm, that's nice of you, but, uh... well, you see, I've got a bunch of clients coming in later, and I've got to prepare a bunch of documents first, so uh, I'm actually going to have to skip lunch today. You know how it goes." Cindy's face reddened some more, and she was doing everything she could to not make any eye contact, as her hands fluttered nervously about her desk. It was quite obvious that she was lying through her teeth.

Well, Cassie had figured as much, which was why she had checked up front with the secretary (who was quite a hottie) on her way in. In truth, Cindy only had one meeting scheduled for today and that wasn't until after four o'clock. She moved to the corner of the desk and casually leaned up against it, sliding half her ass and one leg up onto its surface, her other leg remaining on the floor. She had changed into clean clothes after her shower, and was now wearing a light colored halter top and a loose skirt. Sitting as she was, the skirt was riding up a little exposing her long, smooth leg and part of her thigh. She watched, amused, as Cindy tried hard not to look.

"Really?" she said, "That's weird. I asked the girl up front and she said you were open 'til four." Cindy's face went even redder if possible at being caught in a lie, her cheeks were positively glowing now. "Are you sure you can't slip away just for a little bit?" Cassie continued, pouting, "I planned this really nice lunch for us as a way of saying thank you for going shopping with me yesterday, and it'd be a shame if you can't go. We can make it quick, I promise. The place is just around the corner. It's new."

Cassie waited, having used her best little-girl voice and effectively shot down all of Cindy's arguments already, while Cindy looked at some post-it notes on her desk, pretending to think about whether or not she could spare the time. Cassie was pretty sure she was actually trying to come up with another logical excuse not to go, but evidently she failed, because she finally sighed and said, "Yeah, I guess I can sneak out for just a little, as long as we're back fairly quickly."

"No problem, we will be," Cassie replied, standing up, "And trust me, lunch is going to be just wonderful. You're going to love it."

They left the building and got into Cassie's car. She took them down a couple blocks, made a left and then a right, and pulled into a parking garage. She took one of the automated slips and started down to the second level.

"What are we doing here?" Cindy asked, "Isn't this the parking garage for the hospital?"

"Yep." It was. Or one of the outlying buildings to the hospital anyway, used mostly by the hospital staff and also by the workers of the surrounding businesses. Cassie found and open space and pulled in, shutting off the car.

"Why are we parking here? There's nowhere to go around here."

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