Gabby 1

After my divorce I started going to a local diner for dinner maybe 2-3 times a week. It's a nice place. It's clean, the food is good and not too expensive. I got friendly with one of the waitresses Kim. She's a real looker. Unfortunately she's married. I later discovered that her 21 year old daughter Gabriella (AKA Gabby) also works there as a part time waitress. She goes to college full time in the area and is a social work major. She lives on campus. I always asked to sit in Gabby's area and made sure she got a nice tip from me.

Gabby is a real looker too just like mom. Long dark hair. Beautiful brown eyes. She has a great shape. She has curves where there should be curves. She's about 5" 3", slender and has a great pair on her. About a 34B. Her smile lights up a room. She's 21 years old. I'm 50.

Around Thanksgiving I got stuck with an extra jazz concert ticket. My date had to go out of town for business. I was at the diner one night and asked Gabby if she wanted to go with me to the concert. To my pleasant surprise she said yes.

I picked her up near her house. She didn't want her parents to know she was going out with me. We had dinner at a high end steakhouse near the concert venue. Dinner was great and the company was even better. We each had a drink with dinner. Gabby can put away plenty of food for a small girl. After dinner we went to the concert. I could tell Gabby really wasn't much into jazz.

We went back to my condo and I put on some jazz on my sound system. I also brought out some beers for us. I started to kiss Gabby and reached for her ample breasts. She was OK for some petting but when I started to unbutton her blouse she asked me to stop. I drove her home around 1 AM.

About or week so later I got a text from Gabby asking if we could meet for dinner. I said OK. She managed to get off from her job on a Saturday. I picked her up near her home and we went to a local Italian restaurant. Dinner was fantastic and Gabby's company was even better.

After dinner we went back to my place and I made some coffee. We started kissing again and this time she did not stop me when I unbuttoned her blouse and unhooked her bra. What a wonderful sight! Her breasts are fantastic and I started to suck on her nipples and play with her breasts. I knew Gabby had a few orgasms. I reached for the button on her slacks but she asked me to stop. She said she didn't want to rush things. I told her I understood and drove her home later that evening.

A few weeks later I texted Gabby and asked if we could get together for New Years Eve. She said OK but could we eat at my place. She didn't want to go out. I picked her up around 7PM near her home and we got some Chinese take-out. We had dinner and Gabby helped me clean up. I got out some beers and we started watching the NYE festivities on TV. We started kissing. I gently undid her blouse and discovered she wasn't wearing a bra. She told me she wanted to help me. Things started to heat up and my hand moved to her slacks. This time she let me unbutton and unzip her slacks. She slid off her pants. There she was in all her beauty. Nude except for her panties. I walked her back to my bedroom. Gabby's first time was going to be in a bed; not a sofa or the floor. I quickly took off my clothes. Gabby got into bed. I put my hand in her panties and gently removed them.

I put on a condom and put some KY inside of Gabby. I wanted to make sure she was well lubricated before I entered her. I continued to suck on her tits and play with them. She had an orgasm. I put my finger inside of her vigina. I wanted her get used to something inside of her before the real thing. She started to moan. Gabby grabbed my penis and started to give me a blow job. But I stooped her because I wanted to cum inside of her and not her mouth. I gently got on top of her and asked if she wanted me to continue. I got a yes and a kiss. I gently spread her legs apart and moved my penis closer to her pussy. I asked one more time if I could enter her. She kissed me again and started to guide me in. I slowly eased my penis into her. I didn't want to rush things. I let her get used to the feel of a penis. I kept going until I hit her hymen. I backed out a bit and this time pushed harder. Gabby's hymen broke. She started to moan and begged me to stop. I held her close and told her that all the pain was over and the fun was about to begin.

I began to thrust as hard as I could. Gabby came a few times. Gabby is very loud during sex. I held back and I finally came too; my sperm exploding into the condom. Afterwards we cuddled for a while. This was the best NYE for me in years. I thought I would have to drive her home but Gabby surprised me. Her parents were away for a few days and she would spend the time with me. Gabby was cold so I got her one of my old flannel shirts.

We finally fell asleep. New Year's Day I awoke to Gabby on top of me nude. We had sex again and took a shower together. I made us brunch. We spent the rest of day just relaxing; watching movies. The two of us made dinner. Gabby left after dinner.

We continued dating. Either I picked her up on the weekend at her dorm or near her home. We would go to dinner and then sometimes to a movie. Either way we always ended the evening back at my place for sex. This went on for a few months. Finally the two of us sat down and had a discussion about our relationship. Both of us agreed that we liked being together. I felt we should be up front with Gabby's parents. Gabby felt her parents would be angry especially her dad.

We went to her parent's home one night and explained the situation to them. Gabby and I explained to them that we do love each other and enjoy spending time with each other. While it may not lead to marriage we want to be together at least for now. While her parents didn't seem happy about our situation they understood and were most part pleasant.

Gabby stopped living on campus a few months ago and moved in with me. She needed a car to get back and forth from school so I bought her a used 2011 Subaru Legacy sedan.

We're both happy to be together. Where this is all going to lead I have no idea but it's sure fun!