Jill and Me

After college I rented a room in a house where a buddy of mine lived. It was just him and his mom living there before I moved in. We were both in our early 20s and trying to make our way in the world. Jim was in the construction business and I was a musician.

Jim's mom was a reporter for the newspaper and often had to go out of town. I think she liked having someone else around so the house wouldn't be empty as often. She also encouraged her friends to stay at her house for days at a time.

After several months, Jim moved out of the house and got an apartment closer to the city with his girlfriend. Celia and I now lived in the house together alone. Nothing ever happened between us, but one day one of her old friends came to town for a visit.

Jill Parsons was from Celia's childhood. They were old friends growing up together and they still stayed in touch. Both were now divorced and in their 40s.

It was a warm summer day and I had been out running errands all afternoon. When I got back, Celia and her friend Jill were sitting on the porch enjoying each other's company and a frosty beverage.

Jill had a rather brazen sense of humor, and as I walked up to the porch she said, "Who is this strapping young man?".

In keeping with the silly mood I replied, "Mrs. Robinson, are you coming on to me?".

We all had a laugh and Celia introduced us "officially". I went inside and started to get ready for a concert I was playing that night with my band.

Jill stayed for the weekend and on Sunday night flew back to her home in another city. She was really pretty and there were two or three times over the weekend that one of us caught the other staring. It was amazing to me how much can be communicated with just a few seconds of looking into someone's eyes.

She visited two more times over the next several weeks and we got to know each other a little bit better each time. On her forth visit, however, we got to know each other much more closely.

Jill arrived on a Thursday night and Celia had to leave early Friday morning to follow some story she was working on for the newspaper. I had a busy day on Friday and that night at around 7:00 I was going through my bills and realized that the phone bill had not been paid. I lived and died by my phone so I had to get this paid as soon as possible (no cell phones or internet back in those days!). I realized that I had to write a check and get it to the post office mail box that night so it would go out the next morning.

I asked Jill if she wanted to walk with me to the post office. It was around 9:00 in the evening and there was a warm late-summer sunset going on. She said that she would love to walk with me so off we went.

It was about a half-mile walk to the post office and we talked the whole time. On the way back we went back a different way that took us by a playground. We sat down on the merry-go-round and talked some more. It was getting a bit chillier and the sun had completely set.

As soon as we sat down we both stopped talking. We both knew that the sexual tension had built up and there was nothing more to say. Now it was time to start doing something!

We turned to face each other and looked into each other's eyes. After a couple minutes of this, Jill and I started kissing. While we kissed, our hands explored each others' body.

I felt all of her lovely curves that I had looked at so many times up until that point. He shoulders, her legs, her beautiful red hair... I closed my eyes and memorized every inch of her that I felt as though I were a map maker. She did the same to me.

Eventually we wanted to take it to the next level so we walked back to Celia's house, holding hands along the way.

As we walked up the stairs to my bedroom she became quite nervous about getting pregnant. She had an 11 year old son who lived with his dad. She said that when she and her (then) husband tried to get conceive, it happened on the first try.

She said that she had no protection and neither did I. Bummer! But we did roll around naked in my bed after I agreed that we would not go all the way that night. Instead we kissed and touched each other. I sucked on her beautiful dark red nipples. They were big and protruded out quite far. Her breasts were firm and oh so squeezable.

We ended our first sexual experience with her sucking on my penis until I came. After giving me a blowjob, she asked me if I had ever masturbated while thinking about her. I told her that I had - ever since the day I first met her.

She said, "Well here's something that you can't do for yourself, but I can.", and put my cock back into her mouth. After a few minutes I spewed another huge load of cum into her, which she promptly swallowed.

After that, we both lay there for about an hour. Then she got up and went to her room saying that Celia would be returning the following morning so she didn't want to be seen coming out of my room.

The next day as I was running errands I stopped by the drugstore and bought a pack of 3 condoms- just in case things worked out in my favor that night.

When I got home, Celia was back and she and Jill were sitting on the porch. I went up to my room and there on top of my dresser was a giant box of condoms! Obviously Jill had the same idea as me, but she was thinking ahead!

That night after Celia went to bed Jill snuck up to my room. We barely said anything to each other because we were so excited (and horny!). She tore off her clothes as I tore off mine. She laid me down on the bed and rolled the condom on to my penis as it was getting ready to blast off like a rocket. She then mounted me by sitting on my cock facing my feet.

She rode my cock up and down- softly moaning all through the adventure we were having. In a few brief minutes she moaned louder and I could feel her vagina contracting. She was cumming!

After she came, she got off of me and laid down next to me- her strength having left her. She spread her legs wide for me and I mounted her. I thrust my cock in and out of her for just under a minute and then I came. After this, I laid down next to her and we both stared at the ceiling while we held hands.

A few minutes later she got up, put her underwear and shirt on and said good night. Then she left my room.

I lay there for a long time thinking about what had just happened, and what had been happening over the past several weeks that led up to this incident. It was all so surreal. For one thing, I was 24 and Jill was 40. She had done so many things in life and I was just starting out.

The next day we were all at the breakfast table, as we had been many times before. But now it was different. Jill and I looked at each other differently now, but did not let on to Celia.

Jill had to head back home that afternoon, but we both knew that she would come back again, and couldn't wait until she did!