His Indecent Proposal: 1

Book:Crazy Pleasure (Erotica) Published:2025-2-5

All characters in this story are over 18. Enjoy..
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My name is Catherine. My mother calls me Catherine, everyone calls Kate, and Bobby calls me Katie. Tom calls me Cat because I hate it. Otherwise he calls me Catherine. I’m twenty-two, I’m smart, I’m not lucky. Not lately.
When I graduated from college I moved back home to Chicago to get my resume in order and apply to business school. But then the economy busted, then my parents lost an impressive amount in both stocks and real estate, and then, slightly later, my car died.
I’ve worked almost my entire life. I got a permit when I was fourteen and worked in restaurants, in bars (I was too young to work in them but that wasn’t really a problem – which I’ll get to later), I’ve worked in shitty jobs and really good jobs and usually I’ve come out ahead. I didn’t get a scholarship to college. I paid for half; my parents paid for half. It was going to be the same thing for graduate school. My parents’ half was wiped out in a few short months. My car still needed to be paid off even when it was a useless piece of junk on the street. I got so many tickets just trying to figure out what to do with it.
I did manage to get a part time reception job in the city that paid fine so long as I didn’t need rent or gas or new shoes or clothes or a computer. In a year or two I would have saved up enough for about half of what I needed, and since I was still living with my parents I was willing to wait. I’m not really that patient but I didn’t really have a choice. I’m good looking, not stupid.
But for all my patience I was still a twenty-two-year-old receptionist with an economics degree, and living with my parents.
Bobby is my boyfriend. We met at the beginning of Junior year; he was a TA and is amazing at microeconomics. Since leaving college though he’s gone off to graduate school in Michigan and I’m still stuck here, so it’s a long distance thing. Which wasn’t a problem. The problem is that I’m not really sure how I feel about him now, or how I’ve ever felt about him.
Allison is my best friend. She was a liberal arts major and wants to be an actress. I think she actually just wants to be famous, but I won’t fault her for that.
We met Tom in college.
Tom was older; he was a third year when we were just freshmen. I think somebody told me once that he had three majors in college, in three different schools. I don’t know if that’s true and I’ve never asked him but it certainly sounds like it could be true. Because that’s the kind of guy Tom is. I don’t know if he’s smart. I used to think he was smart, and he isn’t dumb, but now I think he just works hard. I say Allison and I met Tom in college but we knew him before that. He did go to our high school but we never saw him much. He wasn’t in student council, he didn’t work on the paper, he wasn’t in theatre, he definitely didn’t do sports. I think Tom worked all the time. He was usually on the fringe of school, but he always had some connection. Either we had a friend who was friends with him or gym with a girl who was dating him. I think Allison said he worked at the dock. It would explain his hands. How do I explain that, other than the obvious?
I’ll put it this way. Allison says that learning how to move on stage actually requires a class, it actually requires practice. I guess it makes sense. Being up there people are watching everything. It doesn’t make sense to see you twitching or moving around aimlessly or shuffling your feet. And your hands have to be somewhere. When Tom talks, or when he moves, you don’t realize it but he doesn’t fidget, doesn’t bounce. His hands do exactly what he says he’s going to do. Or they show you. They don’t waste time.
And Tom doesn’t waste time, as most people come to find out.
I had been back in the city for about a year. I was saving money and hating how useless I felt. Allison was looking for work and not having much luck in theatre. We got together at the gym Mondays, Wednesdays and Fridays (I also went on alternating Saturdays or Sundays when I could). I love Allison but we hit the gym more because we were friends than we had the same goals in mind. Allison was more fond of the stairmaster and the track and talking to guys she knew (she has been looking for a boyfriend since she and Ryan broke up two months ago but she is exceedingly conservative and better at flirting than saying yes to a date). So here’s where I got myself into trouble, maybe.
I’m good looking. I said that before and I’ll say it again to get it out of the way. I’m 5’7″, I’m a brunette, and my breasts are not as big as Allison’s. She has full, heavy boobs that droop lower on her chest. My breasts are Cs (bigger when I’m on my period) but they’re higher on my chest and rounder than Allison’s. Some guys prefer hers. Most guys prefer me. I have long legs. I’ve never measured but it always seems to me when I squint in the mirror that my legs are longer than the rest of me. To compensate for that (I was self conscious when I was younger – still am), I went to the gym a lot. And then my ass got really round. Which I was self conscious about. So I started doing sit ups every day. And I run. A lot.
I also eat a lot, but nobody knows that. I say a lot – for a girl that just means more than you’d think. I used to purge in high school but I gave that up when I found out that my girlfriends were idiots. I do occasionally feel the urge to throw up but I don’t. I eat carrots instead. Or I run. I spend an inordinate amount of time working out. In fact, when I’m not working, I’m working out. I seldom drink anymore because I don’t like to count calories when I’m drinking. I won’t lie; recently, I have developed more of a tummy than I’d like, but my sides are still flat and Bobby tells me it’s sexy. I’m not really sure now.
I have green eyes. Dark green eyes, and long lashes. And my arms, for what it’s worth (and guys don’t know) are extremely strong. I can pin Bobby to the bed with my legs, but I don’t because it makes him nervous.
So I’m pretty, but I’ve always been pretty and it’s been very helpful getting jobs. It has not been helpful getting hit on. When I was younger I was embarrassed, when I was in high school I was flattered, in college I would either feel empowered or weird about it. Now I wish every job interviewer would stop staring at my chest, or my neck, or my shoulder, or my ass. Don’t get me wrong, I’m grateful for the way I look, but I look this way because I work hard. Allison is my height and nearly the same weight, but she’s not toned, anywhere. Though guys don’t seem to mind unless we’re standing next to each other.
I guess that’s sort of my point, in that you can look however you want to look, but you’re considered attractive for any number of reasons.
How do I feel about sex? I like sex. Girls that look like me get reputations for being sluts or ice queens. I’ve been called both. I’ve also been called “whore” and “bitch” and “cock tease” and I didn’t like that either. Bobby once told me, as a joke, “Girls don’t get to be hot and have feelings, too.” It certainly feels that way sometimes. Bobby waited for me to laugh. I didn’t.
But I guess I’ve been all those things. I had sex with the boys I wanted to have sex with, my boyfriends. I didn’t talk to guys that were slobbering over themselves or who were so deluded by their own bravado that they thought it was a real big honor for them to even notice me. And I didn’t have sex with the boys I didn’t want to have sex with, and sometimes those were my boyfriends too.
I don’t know how much sex is too much. I don’t know how much is too little. (Bobby and I pretty much stay in all day whenever he gets back from Michigan, and when he’s gone I definitely feel like I’m deprived.) I had more sex with the boys I enjoyed it with. But almost all of the sex I’ve had is either a fast and furious affair or a long but repetitive process. I’m not that creative myself. I’ve never really been sure what boys expect, and I’m beginning to fear that because of how I look, or what I look like, boys don’t want to tell me. (I have had the distinct displeasure of being “told” what to do in bed by a guy or two who thought he was being my “daddy.” I wasn’t impressed and I don’t like being hit. I stepped on his balls when he tried it again and I guess that’s where the “cock tease” nickname started.) So though I’m no stranger in the bedroom I’ve never really done anything you haven’t done. I’ve just probably done a lot more cardio. (Usually a lot more than the guy who’s showing me a good time.)
But when boys are so nervous just talking to you you tend to stick with your girlfriends and like what they like, diss who they diss, learn what they have to say, try to say it back. I’ve often wanted to experiment but I don’t think I’ve ever been sure what it means, or what I mean by that.
I guess I just have an open mind about it.
In the meantime, stuck at home and working, aside from Allison I’ve had a lot of time by myself. My parents are there in the mornings and late at night (and the weekends; but I work weekends) and Bobby’s in Michigan.
I used to love Bobby. He’s smart, he’s tall, he’s got the whole ten year plan thing covered. I still love Bobby, in a way. But I don’t love him the way I did two years ago. We’re moving apart, and we feel that, but it’s a steady thing at least having somebody, even when they’re gone for months at a time.
So my schedule is pretty set. Work as much as my part time job allows; save as much as I can; go to the gym with Allison in the early mornings or evenings. That’s it, really.
That was it.
And then, well, things took a turn.