Guilty Pleasures - Cover

Guilty Pleasures

Copyright© 2018 by Armera Llsehi

Chapter 10

Fantasy Sex Story: Chapter 10 - It's not every day a person gets to experience their life over. But for one man that is being offered to him. Yet it's not as simple as it sounds. Is it ever?

Caution: This Fantasy Sex Story contains strong sexual content, including mt/ft   Ma/ft   Teenagers   Consensual   BiSexual   Heterosexual   Fiction   Science Fiction   DoOver   Anal Sex   Oral Sex   Transformation  

George slept rough that night. Tabitha was broken after leaving Steven’s, so switching back to his normal self the man figured it would help to ignore those awful feelings. But it didn’t, they remained there and the remained as strong as ever. Thankfully Genzo seemed to be occupied, entertaining another woman. Tabitha went to school, even though she felt like not going, but just as George was keen on finishing high school and going to college, he is just as determined to do the same as Tabitha. So skipping out is not even a consideration.

Home room goes by fast. The class really isn’t long as it is, but today it seems shorter than usual. It isn’t shorter and it doesn’t go by fast, Tabitha just has a lot on her mind. This doesn’t go unnoticed by her home room teacher, Mr. Welch. After the bell and when everyone else has filtered out, he stops Tabitha to question her about what is going on.

“I just had a sort of break up,” she explains. “I can’t say any more than that, Mr. Welch.”

Mr. Welch grins and says, “Please call me Gordon.”

She looks up at him and frowns. Why would he have me do that? The girl expresses as much to him.

“Well, because I already know all about you and Steven,” he begins, which is a total shock to the teen. “Don’t worry, he didn’t go into any details, but I understand why you two split. Sam has a big mouth and if he found out it wouldn’t be good at all for Steven. But he suggested that I could help you.”

Tabitha is confused. Never did she think this man as being one to go after anyone other than his wife, and certainly not his students or underage girls. “How so?” she asks.

“Well, how about we start with you doing a little babysitting for my wife and I,” he suggests. “We have plans to go out tonight. You can get your mind off of things. I mean what works better than occupying your mind with work?”

“Yeah, I guess so,” Tabitha says.

“My wife and I haven’t had the pleasure of having a student as young as you babysitting, so it could be a good experience again,” he says and then explains. “The last time we had a student over, it got messy. After almost a year, she started entertaining thoughts of moving in with us. My wife didn’t like it and she almost caused some serious problems for us. Since then, we have stuck with college girls.” He smiles, touching her hip. “Needless to say, we go through babysitters every so often when it is time to move on and we don’t have any trouble. But you come over and sit and while the wife and me are out, I’ll talk to her.”

Tabitha agrees to babysit and gets the address and time. He’s right not only a little work will help to fend off her problems, but a change in men, and obviously women, will go a long way to help her heal and forget.


She shows up at the scheduled time, watches the kids and gets them to bed without a fuss. Afterward she sits and watches the television until they return home. Nola, Gordon’s wife, insists Tabitha to stay and drink some coffee with her. Tabitha objects to the coffee, so the woman switches the beverage to hot tea, asking to be called by her first name. They chat while Gordon heads into his office to finish up some paper grading.

Nola starts off telling the girl about their night and Tabitha tries to be enthusiastic and pleased for her, but she is still feeling down. The woman catches onto it pretty quickly and finally questions her about it. “You appear to have some sort of problem,” she suggests. “You look like you lost your best friend. Want to talk about it?”

As a matter of fact, Tabitha does. And where she had been going to the little snotling for advice, she felt she didn’t want any from him. But a woman would understand better. “Kind of,” she admits. “What did Gordon tell you?”

“Not much,” the woman answers. “We discussed you being the babysitter for a bit, but nothing really beyond that.”

“Well it’s about a teacher, and obviously a friend of your husband, Mr. Giles...” he voice kind of trails off, not quite knowing what to say or how much of it to tell.

“Let me guess,” Nola says, grinning. “You and he have been having sex and it’s become complicated.”

“Something like that,” Tabitha agree. “He’s been pushing toward something more between us, but he’s engaged and I don’t want that.”

“That man, no matter how much he says it, doesn’t want to marry another man,” Nola says, shaking her head. “He insists that living with a man is easier than a woman. I know he likes dick about as much as I do, and I’ve told him he can get it whenever he wants, but all he has to do is find the right girl.”

“That’s kind of disgusting, isn’t it?” the teenager asks.

“What? Getting some dick?” Nola asks, raising an eyebrow.

“Yeah,” Tabitha says, nodding.

“Not at all,” the woman answers, looking slightly offended. “We’re all human honey. I mean how is it not weird that two woman sleeping together or two shemales, or even a shemale with a man or woman?”

Tabitha shrugs her shoulders. “Well it hot seeing two women together. Besides I’ve...” George has slept with a shemale before, but he has always figured they were pretty much women so no big deal. Or course he has never been fucked by one—he did all the fucking. “I’ve seen it in porn.”

Nola smiles at this. “Tell me, what is the difference between and woman’s asshole and a man’s? Aside from the hair of course.” The girl shrugs. George has had plenty of that, but he never thought of it. “Nothing at all. Anyway, this isn’t about sex with men or women, is it?”

Tabitha shakes her head. “No it’s about, uh, about our age difference.”

“And you are afraid to give into your feeling because of that?” the woman asks.

Of course that isn’t why, but she can’t quite come out with the truth can she? Would the woman even believe her or would she consider Tabitha a complete nut job? “Not exactly,” she answers. “It’s a little trickier than that.”

“Well, I never understood the whole difference in age thing,” Nola says. “I mean what’s the difference between a fifty year old and a thirty-five years old? Other than age, nothing. SO why make a big deal when you what, fifteen and Steven is like twenty-five, twenty-six?”

Tabitha shrugs and Nola gives her a tell me what’s really wrong look. The teen chews on her lip, trying to think of how to phrase it. “It’s not that I don’t want to. I’m just not sure I can like a ma ... I’m just scared,” she blurts out with a rush.

“I take it that you’re not a virgin then?” the woman inquires.

The girl quickly shakes her head. “Not in the least.”

“I figured not,” Nola says. “A long as we have known Steven he has never been one to wait.”

“How long have you known him,” the girl asks, genuinely curious.

“Since middle school, believe it or not,” Nola says smiling and leaning in closer over the table. “He was actually my first fuck. I lost my virginity to him. After that I began fucking my husband. It has been nonstop since then. Every once in a while we still get together.”

“And Gordon knows about it?” Tabitha asks, not believing what she is hearing. Then she is floored by what the woman says next.

“Certainly. Even Gordon and Steven get together.” When Tabitha flashes her a look of disbelief, the woman continues. “Honey, they were fucking each other long before I met them. I think they started about the fourth grade.”

“And you don’t mind that?” the teenager asks, feeding into the revelation. “How do you deal with it?”

“What’s there to deal with?” she asks. “I know many can get hung up on it, but it’s no big deal. I like to watch sometimes. It gets me really going. What is better is getting fucked by them after they finish up. And boy does Steven have a big one.” She says this with a wink, which for some strange reason makes Tabitha laugh. Then they are both laughing by the time Gordon comes wondering into the kitchen.

“You two seem to be in a happy mood,” he says. “Discussing men and their short-comings, I assume.”

“Something like that,” his wife admits. “It’s a pity that they’re not all as nice and agreeable as you.” Then she sits up straight, looks at Gordon and then at Tabitha. “He is a very nice man,” she says softly, “very considerate and agreeable.”

Tabitha frowns a little, trying to understand what the woman is getting at. Surely she isn’t suggesting that the she get with her home room teacher right in front of her.

As if reading the girl’s mind, Nola asks, “Why not? It will get your mind off Steven while giving my husband a treat. I get the bonus of watching.”

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