Jill

Jill is the daughter of a friend. There is an age difference between us. She's 38 and single. I'm 55 and divorced.

This past spring I got stuck with an extra theater ticket for the musical Camelot. I gave Jill a call and asked if she would like to join me. She agreed to meet me for dinner and the show.

Let me describe Jill. She about 5' 7", about 140 lbs, 38B, shapely, dark brown shoulder length hair, nice legs, beautiful brown eyes. She is a very attractive package with a smile that lights up a room. She works as a graphic designer.

We agreed to meet in front of the theater on Saturday evening and then go for dinner.

Saturday night came and I waited in front of the theater. Jill finally arrived in a cab; carrying a briefcase. I couldn't figure out why she had that. Jill looked fantastic with a nice skirt. We walked to a nearby pub and had dinner and a few drinks. Before we went to the pub Jill asked if I could put the bag in my car. I asked what was in it. She said it was some projects she wanted to show me.

Dinner was uneventful. Just some small talk. I told her about some consulting projects I've been doing. She told me about her work. We finished dinner and walked to the theater.

The show was fantastic. We both enjoyed it. I suggested that we head back to my condo for some coffee. Jill had not seen it since I fixed it up. I said I would drive her back home to her apartment.

Arriving at my condo I showed Jill around. She had not seen it in a while. We sat together on my sofa. I got some cold beers and put on some smooth jazz on my new sound system. I put my arm around Jill and we started making out. She got up and told me she would be back. I assumed it was just a trip to the bathroom. She seemed to take forever to return but when she did was I shocked. She was wearing just one of my long sleeved Brooks Brothers dress shirts, her panties and as I later discovered had also taken off her bra. I've never seen my shirt look so good!

Things started to heat up. I unbuttoned the shirt she was wearing and started to suck on Jill's ample breasts. I was like a starving man with food. Jill pushed me away. She said she was nervous because it has been a while since she had sex. I suggested using my bed instead of the sofa

I lead her back to my bedroom and I quickly took off my clothes down to my briefs. Jill sat on the bed. I helped her to take off the dress shirt. I removed her panties without objection. I just slid them down her shapely legs.

The foreplay was great. I wanted Jill well lubricated before I entered her since she said it's been a while since she had sex. I did not want to hurt her. I asked if she was on birth control and she said no. So I got out Rough Rider condoms and KY Jelly just to be sure she was well lubricated. I put some KY in her pussy.

Jill had an orgasm two or three times during foreplay. I felt she was ready for me. I told her I would stop right now if she wanted me to. She told me she needed me inside her now. I got on top of her; nothing weird. Just the missionary position. I put on a condom. I gently spread her legs apart a bit more because I couldn't enter her the way she was positioned.

I asked her one more time if I should stop. She didn't reply but she began to guide me in. She was very tight when I entered her; almost like a virgin. I'm glad she was well lubricated. I kept moving in a bit at a time until I was fully inside. I began to trust. She came a few more times before I finally came.

We spent the rest of the night cuddled with each other.

Sunday morning I awoke to find Jill naked on top of me playing with my dick. We spent the rest of Sunday morning having other round of sex. Jill was still tight but not as tight as last night. I got up and made us some breakfast. Jill looked 100% stunning in my shirt. She admitted to me that she was a bit sore but a good kind of sore.

After we ate she asked me to get her briefcase and finally told me what was inside. A change of clothes and some toiletries. She figured that she would be spending the night.

We started dating on a regular basis. Our usual ritual was Jill would come over after work on Friday and stay with me for the rest of the weekend; leaving to go back to her place after dinner on Sunday. We would have dinner at my place on Friday. Saturday Jill would finish some work and then in the evening we would go out; maybe to a movie, maybe to dinner or we would just stay home and relax. Each night during our time together was filled with wonderful sex. Each week Fridays couldn't come fast enough. After about three months of dating, Jill was my "steady".

I convinced her to give up her lease and move in with me. I helped her financially to buy out her lease. Initially her parents were not too happy with the difference in our ages but they finally came around.

I surprised her with plane tickets for a trip to London for 10 days. Once we get to London there is another surprise waiting for her. With the help of her sister I got her ring size. I bought her an engagement ring.