The first time

I was about thirteen and had a continual hard-on which was embarrassing most of the time. I had a paper route and every day made my rounds with a canvas bag around my shoulders which threatened to make me permanently lopsided. I used to pull the bag around in front to hide my erection. A plus to this was that the bag rubbed against my cock and felt good.

The paper route wasn’t very large. I only had about forty customers. One of these customers was a lady in late middle age. She lived alone in a small house and every day she would invite me in for milk and cookies. I loved it because she usually wore a flimsy robe that showed her nipples as pointy little knobs straining against the fabric. I suspected that she didn’t wear a bra but in my inexperience I really didn’t know. I did notice that day-by-day she got bolder in her exposure. Each time I went there, she showed a little more skin. At first it was just a little cleavage and then more each time until I could start to see the curvature of her breasts. She would wear the robe loose and bend over toward me so that I got a good look down her dress. She was sending me some sort of signal but in my naivete I just didn’t get it.

When she would pour the milk, she would stand next to me and press her boob into my shoulder. Finally, one day as she was pouring the milk, I boldly ran my hand up her leg. I expected this would make her mad and I would be banished forever. She didn’t bat an eye and my hand was soon on her bare pussy. She tilted her head back and softly moaned. She undid the front of her robe and dropped it to the floor. It was a pubescent boy’s dream. I could see everything...tits, ass and cunt...everything. With my hand still on her pussy, I started sucking on her nipple. She moaned again and managed to choke out, “Take me into the bedroom and fuck me!”

When we finally fumbled our way into the small bedroom, she jumped onto the bed which made her tits flop around like puppy dog’s ears. I had a hell of a time getting undressed. If she hadn’t helped me, I probably would still be there, whirling like a dervish. I finally got mostly undressed, at least the important part, and jumped on her. I started stroking almost before my cock was fully in her hole. It was veeery good. It was also over very quickly. Fortunately she was on a hair trigger so we both got our orgasm.

OK, what do I do now? I had fantasized about fucking a woman for years. I never gave any thought as what you say or do when it’s over. Do I say “Thank You” or “good fuck” or what? She saved the day for me by wrapping her arms and legs around me and saying, “Stay in me boy. It’s been a long time since I’ve felt a man’s tool in my love hole and it feels soooo good.” I didn’t know that women could talk dirty like that. It was so exciting that I got another hard-on. She felt it and said, “Fuck me again. I really want it again.” And so I did.

Besides talking dirty she threw herself into fucking with wild abandon. She moved her pelvis around and up and down, all the while groaning and carrying on. This spurred me to even greater efforts. I think we did it four times but I wasn’t in the mathematical mode at the time.

From then on it was a daily thing. I made sure that she was at the end of my route and boy did I hustle to get there. I got a commendation from the paper for my speedy delivery. I would run as fast as I could with a king-sized hard-on in my pants, getting to the ladies home in double quick time. She would be waiting for me with nothing on but that flimsy robe. The minute I came in the door she would drop it and be standing there in her birthday suit. God! I can see her now. Her tits were huge and she had dark black cunt hair. With this incentive I got my undressing down to just a few seconds. That was the time it took us to get into the bedroom.

One time she was feeling frisky and had me fuck her on the living room floor. It was great. Anyone could have looked in the windows and they would have seen everything.

I had this fear that it was all too good to last so when I came into the house one day and she did not disrobe I thought it was over. My fears were groundless. She was having her period and didn’t want to fuck. She was a very kind lady and knew my need was great so when I came in the door she got down on her knees, opened my fly and gave me my first blow job. I hadn’t considered that women did this but was highly gratified by the whole thing. It was a new sexual dimension. Not quite the same thing as plunging my rod deep into her cunt but on the plus side it was very exciting. She actually had my cock in her mouth and was enjoying it! I came in her mouth and could see my cum running down her chin. Wow!

After this I started asking the girls in my school to suck my cock. About ten percent said yes and many of those were first timers. I had no idea. These girls had been there all the time, ready to suck my dick, and I had said nothing.

When I told the lady about this new adventure, she said that the girls were excited about having sex but the fear of pregnancy made them say no. Sucking cocks was a way for them to have the sexual excitement without the fear. I said I didn’t see how they could enjoy it without an orgasm so she introduced me to the delights of 69. I loved it!

I tried this double ended licking on my next date with one of my school girl sluts. She loved it and, as I should have guessed, told all her girl friends about it. I was overwhelmed by the number of volunteers who were ready to gobble the goo. Soon the other boys were reaping the benefits of 69. The school was the center of licking and sucking. I was amazed by the thought of all those goody-goody virginal girls getting it off with a cock in their mouth. It was Paradise.

One day when I stopped off at the lady’s house for my daily piece of ass, I was surprised to see that she had a visitor. The lady said that the visitor was her sister who had heard of my prowess and wanted to try me out...in short she wanted me to fuck her. I’m anything if not agreeable when presented with a free fuck, so I agreed. She was a slightly built woman with hardly any tits at all and skinny as a rail. Ah well, pubescent boys like myself look at every woman as a potential sex partner and mentally undress them. Guessing what women look like in the buff is a continual game. Now was my chance to see and fuck one of the thin ones.

We went into the bedroom and undressed each other. She had no breasts to speak of but her nipples were hard, prominent little knobs. When I sucked them she really reacted. She had an orgasm right there. I later learned that women with small breasts had all their nerve endings concentrated in a small area which made them very sensitive. The fact that I had my finger in her cunt probably helped.

She was very lively in bed and insisted that she should get on top. This was a new experience but had many advantages. I could see all her goodies at once and would give an occasional assist by reaching out and massaging her clitoris. She loved it. As she was riding my cock, up and down, I could see her face as she threw her head back with her mouth agape. She was panting and moaning. I don’t think she had a single inhibition in her skinny little body. The fact that the lady of the house was standing there, watching, didn’t slow her down one bit.

Well, all this was many cunts ago. I’ve always found that older women are ever anxious to help young men gain experience.