First Time with a Woman

This story is about me being almost 19 and still a virgin with women. I had played around but never got home, I was shy and not very sure of myself. I had a couple of friends who didn't know this but always thought they would fix me up, on one occasion my friend who had a steady who was a nurse said his girlfriend had a neighbor who was a little older and needed to go out would I double date with them. I agreed and we set it up.

On the night of the date, he said we were going to the drive in movies, I said ok, and when a car pulled up to pick me up it was him and his girl in the back and an older lady driving. I didn't know it at the time but she was in her 40s but looked a little younger, not a model type but very attractive with a fair body. We introduced and I got in the front seat and off we went to the drive in, not being really sure of myself I took it very slowly. In the rear view mirror I could see my friend get a blow job from his girl. I slowly kissed the woman and she liked and gave tongue.

We made out throughout first movie and when my friend and his girl went to the concession stand we chatted, I told her I was nervous and then sprung it on here that I had never had sex with a woman, she said are you gay, I said no but very shy. She told me that a first time shouldn't be had in the car and she was ok with just fingering and stuff. She told me she would like to get me in bed and take my cherry, I was a little taken aback but she laughed and said I would enjoy it. We set up a date.

After the date my friend said, why didn't I fuck her and I told him she didn't want to do it in the car but was enjoying the backseat show. He laughed and said his girl was an exhibitionist, I said I could tell. I told him she was hot and we set up a meeting again. He smiled.

On the night we were to meet, she drug me to an off the wall bar and I told her I wasn't older enough to drink, she said she knew everyone and I would get served with no problem. We had a couple of drinks and she said lets go to my house. I said OK, I was very pumped but also a little nervous, my cock didn't notice as it was hard as a rock.

We got to her house and she said I am very horny and we headed right for the bedroom. She unbuttoned my shirt and undid my pants, I was really ready, I groped her trying to undo her blouse and bra, she had very nice breasts, I am more of a leg man, when she got my underwear off my cock was sticking straight out, she rubbed it and said it was nice, not too big, as I finally undid her panties I thought I was going to cum just looking at her nice pussy with just a small tuft of hair, she pushed me down on the bed and proceeded to get on top, like I said I was not going to last long, she moved up and down a couple of times and stopped just as I was ready to cum, she smiled and said to ease into it she moved up and down a couple of more times and I unloaded, she stayed on top for some time and then got off and licked my cock off, I could feel it getting aroused again.

She then asked if I knew how to eat pussy, I said I hadn't done it but had tasted pussy juice on my fingers, she slowly moved over my head and told me to lick her clit, which was pretty big, I did and as I was licking it some of my cum dripped into my mouth, she then sat on my face and told me to eat my own, and I did, it was very different tasting your own cum. Pretty soon I could feel her getting much wetter and she grabbed my head and pushed her pussy hard into my mouth. We laid there for a while resting.

She then turned me over and massaged my back and ass, then I could feel her fingering my ass, I moved a little and she asked if it bothered me, I said it hurt at first but now felt pretty good. We did sixty nine and I even licked her ass which she liked a lot. She gave me head, which was the first from a woman, she could swallow my whole cock which was exciting.

I pushed her away saying I was about to cum again but she went right back down and took the whole load, she swallowed it all and then we laid there just resting. She asked if I had enjoyed it so far, I seriously thought we were done, but she had other ideas, we laid for a half hour and she started sucking me again, when she got me hard she rolled over and I took her doggie style, and fingered her ass as I fucked her. She started moaning and I could feel her wetness increase as she came, this time I lasted for a much longer time and a couple of different positions.

I spent the night at her place and was surprised when I woke up with her sucking me, we fucked for the third time and I was getting the hang of not cumming right away as she controlled my movement and helped me, she even whispered in my ear that when I came back the next time were would have some new things to explore, I asked her what but she said we will keep that a surprise.

I can say that the first time with an experienced woman was very good for me as it taught me a few new things plus I learned control and making sure that the woman was taken care of.