Chapter 1

It's funny how things can come together for you when a sexual fantasy suddenly moves very much into the realm of sexual reality. I'd been fantasizing about a friend's high school age daughter, Catharine, for nearly three years. Like many young teenage girls, even as a high school sophomore, Catharine had been very sexy and increasingly mature physically during her last three years of high school. As a high school senior, she'd been nothing short of a total fox. I had enjoyed being around Catharine, seeing the pics her mom had shared with me and I'd stroked myself to orgasm many times imagining how hot it would be to actually fuck Catharine one night during the year.

When Catharine's mom asked me if I'd write a letter of support and recommendation for her sexy young daughter to get financial aid and for entrance to the better colleges, I knew things were falling right into my lap. I told her mom, "Sure, I'd love to write letters of support, but I'll need to sit down with Catharine and get to know her a little bit better so I can write the best and most accurate letters possible," and her mom said that her senior year daughter would come over to my place anytime convenient for me so I could interview her. I could hardly wait.

I set up an appointment for Catharine to come see me the next afternoon. Sure enough, at the appointed time after her high school classes were out for that day, she arrived at my house and I showed her into my family room. Catharine was dressed in a nice top, and matching pants that looked very attractive on her slim shapely figure. Her breasts looked to be at least B-cup in size and verging on C-cup in fullness and my cock responded immediately.

"Hi, Mr. Land," Catharine greeted me as I showed her where we would sit to talk. "Thank you so much for being willing to help me get some college aid to go to school," the young teenager said as she sat and waited for me to ask her some questions. We quickly dispensed with the things I needed to know to write good letters of support for her, and then I turned to what it was going to cost Catharine for me to help her out.

"Catharine, I'm more than happy to write these letters for you, but I have to let you know that there's going to be some cost to you as well. I'm not talking about money or that sort of thing, I'm talking about you giving me something in return for my time and effort," I said as I felt my cock flinching involuntarily inside my briefs. "Let me just spell it out for you, Catharine," I said as I shifted to relieve the pressure on my hard cock. "You're a very sexy and very attractive young woman. I honestly don't know if you're still a virgin or not, but here's the deal, you're going to have to agree to have sex with me this afternoon and at least once a week from now on until you either finish college or graduate school whenever you're here in town, OK?"

Catharine looked me straight in the eyes as I told her the price of my support for her college plans. She hadn't protested what I'd demanded of her but she hadn't flippantly said, "no problem; let's get it on now" either. She sat there listening as I told her what I expected. I felt sure Catharine had never expected this as an exchange for my assistance nor had her mother figured on this when she'd sent her daughter to see me that afternoon. I KNEW her mother never expected her beautiful teenage daughter to be taken sexually by an older man -- but we'd find out how Catharine felt about my proposal to her.

"Well, Catharine, there it is -- my offer. What do you say?" I asked as I looked at the sexy girl in front of me.

"Tom, what if I told you that I was agreeable to all that you've said, and that I'd go along with your demands -- and that I'm a virgin and you'd have to be the first man to make love to me. It's true. I am a virgin and I've never been fucked or had sex with a man before," Catharine said as I felt my cock growing very hard and thick in my pants in response to the reality that she'd just shared with me. "But, I know you're probably sitting there wondering where I'm at with all this -- I'm right with you, Tom," Catharine said as she moved over closer to where I'd been sitting and let me get up and move next to her as well.

"Tom, I've thought you were very hot for some time, and your demands are more than fine with me, " Catharine said. "I need to learn about making love, having sex and what turns men on and you're a perfect man to be my instructor, if you're willing," the sexy young teenager said.

"Catharine, you know I'm willing. I hadn't quite figured on being your firs sexual teacher, but that's a role I'll gladly take on with you. So, you're still a virgin, huh?? I must tell you that makes you even more sexually exciting than you were already," I reassured Catharine as I stood from where I'd been sitting and walked over to the sexy teenager.

I wasn't quite sure where to start with Catharine; I hadn't been presented with the challenge of deflowering and teaching a sexy 18-year old teenager who was also a virgin in a long time. Oh, I'd taken several virgins but never one in this these circumstances. I felt my cock already growing very hard inside my pants.

"Catharine, what do you know about sex?? Anything?" I asked, not wanting to presume anything but not wanting to waste time showing her something that she already knew about. I knew that just because she was technically a virgin did not mean she was totally inexperienced sexually.

"Well, I've never had sex with a guy -- not with a cock in my pussy, that is. Yeah, I've given guys blowjobs and I think I do a pretty good job of that. I've talked with girlfriends about how to make a blowjob really good and I've practiced in my bedroom at night with hairbrush handles and things like that," Catharine said.

"Good, that'll do for starters then," I said, as I stood there in front of Catharine and unzipped the front of my pants and reached inside to pull out my cock that was already at nearly full erection. "Suck this, Catharine, and while you're doing that for me, I'll decide what our next step will be in your sexual education as a young woman," I said, and Catharine immediately reached up, taking my cock in her hand and she seemed to like the size and thickness of my hard cock.

"Your dick is certainly bigger than any of the guys my age that I've sucked off before," Catharine said. "I hope I can do this good for you, Tom."

"Catharine, the first lesson in enjoying sex and being good with a guy is just to let yourself relax and go with what feels right. OK?? Don't get stressed out whether you're going to give me the best head I've ever had in my life. Believe me, at your age and your sexual inexperience, you probably aren't, but it's going to be very fucking sexy having you stroking and sucking on my dick, so enjoy it, baby," I said as I moved over and sat back down, letting Catharine get in between my legs where she could comfortably get at my hardon.

Catharine quickly began stroking my erection and she was making it feel really good. Her soft firm hand jacking my cock up and down was sexy, and I let myself moan and encourage her to give her the feedback that she was doing a good job. I wanted her to enjoy it as much as I wanted her to give me the best blowjob she'd ever given any guy before.

"Ohhhhhhhhh, yeah, Catharine, oh yeah, mmmmm, that's feeling good, baby," I moaned and as Catharine continued to jack my cock up and down and she caressed my balls, I reached down to the sexy young teenager's chest and cupped her right breast through her top. Her nipple felt very hard and I knew that having my naked hardon in her hand was really turning Catharine on. That and the fact that she was getting ready to suck my dick and no telling what else when I told her what I wanted her to do with me and for me. Catharine seemed like the kind of sexy teenager who'd be willing to do whatever I asked within reason. I hoped she'd be a quick and wiling student.

After just a couple of minutes of stroking my cock, Catharine leaned over and she began licking her tongue across my cockhead, licking off the drops of pre-cum that had already begun to ooze out from my juice hole. She was eager to do whatever she thought I'd like, and she seemed to enjoy licking and pleasuring my cock. I continued to squeeze and play with Catharine's breast through her top and wished that I'd thought ahead enough to get her undressed before we started our sexplay. Catharine moaned and sighed in response to the touch of my hand on her tit and I loved the way she seemed to enjoy my titillation of her breast.