Chapter 2

While the sex with Rosalind was good, I knew that what we had shared was just a "get your rocks off" kind of sex. I wanted to continue my sex education and see what more there was to learn. But, just one sexual encounter was not going to make me a lady's man. Not by any stretch of the imagination. I was still shy when it came to talking to girls. Over the next few months I did go out on dates a couple of times, but they were more a case of a couple of friends doing something together as opposed to a real date. So there was no real chance of furthering my education. And then circumstances intervened and taught me something new.

Debbie called me one afternoon and asked if she could talk to me about something. Now Debbie had become a bit wild since her dad had left. I knew she had been experimenting with drugs and stuff and the two of us had not spoken much in the last few months. So I really could not imagine what she wanted. When she came over to talk, I discovered that what she wanted was money. She wanted to know if I could loan her about $50. Now this was a good bit of money back then, especially for me since I was working my way through college.

Now as I've said earlier, I liked Debbie. She was the stuff of fantasies. She had blue eyes with long blondish-brown hair. Her chest was considerably bigger than her mom's. And her jeans fit her just so perfectly. Well, you get the idea. As much as I wanted to help her, I knew two things. She probably wanted the money for drugs or liquor and I would probably never see the money again if I loaned it to her. I decided to put her off as best I could. I told her I did not have that much money on me at the time but would loan it to her if I did. Debbie said, "Well, could you get it for me by tonight?"

"Debbie" I said, "I just don't know if I should loan it to you. I mean, it is a good bit of money. What do you need it for?"

"I just need it," she said. "Wayne, I need the money badly enough to do a favor for you if you can get it to me tonight. Mom won't be home and if you bring it over around ten o'clock I think I can make it worth your while."

That had my mind racing. I could not believe she was hinting at sex in exchange for money. I tried to rationalize things in my head. I know that taking money for sex is prostitution. But I just could not think of this beautiful girl I had known for the last five years as being a prostitute. So if she was offering me sex, it had to be just as a thank you for loaning her the money, kinda like interest. I decided I could live with that idea. And after all, how many guys get their first two sexual encounters from a mother and her daughter? Could I give up that possibility? So I shrugged and said, "I think I can be over there with the loan somewhere around ten." She smiled and replied, "Good. I'll be waiting for you." She gave me a friendly hug and headed out.

After going to the bank and getting the money, all I could do was wait around the house until the appointed time. I didn't want my parents to know what was going on for various reasons, thus I was hoping they would not decide to stay up late. They didn't. I was able to leave the house without being noticed just a little before ten o'clock. I went across the street and knocked quietly on her door because I sure didn't want to wake her brother and sister up. She must have been waiting for me because she quickly answered the door and got right to the point. "Hi Wayne, did you bring me the money?" She let me in when I nodded, closed the door and said, "Let's go back to my room where there will be more privacy. My brother is still up watching TV."

In her room, I handed her the money. I said, "Now this is just a loan, right?" I guess I was still debating the legalities of this transaction. Just did not want to make her into a prostitute. "Of course Wayne," she said, "I should be able to pay you back in a couple of weeks. I really appreciate this." What I wanted to say was, "Yeah, well, then how about showing me how much you appreciate it." But instead, what came out was a simple "No problem Deb, just whenever you can get it back to me is fine."

There was a lingering silence, which left me thinking maybe I had totally misread her meaning earlier in the day, I started to reach for the door when she grabbed my hand and said, "I seem to remember promising to make this worth your while." She reached up in back of her and undid the tie on her halter top. As it dropped I could not help but stare at those beautiful, large tits. At this point in my education, I was no expert on tits. But Debbie's had to have been double the size of her mom's. I slowly reached out and lifted them with my hands, feeling the weight of them. Debbie pulled my head to her chest and whispered "Suck on them Wayne." For the next several minutes I did my best. When I came up for air, I realized that at some point Debbie had managed to push her shorts down, revealing a bush the same color as her hair.