Deli Girl

My name is Tom, I am 54, separated now about a year now, with the divorce becoming final soon, from an 8 year marriage that should have never happened, but oh well. I was married before too, that one lasted 24 years and two kids. She wanted to live a single life, one she really never got to experience because we married so young. I am 5’ 10, about 185 lbs, with salt and pepper hair. I guess I am of average looks, with a slight gut now. I work as a software specialist, and have been with this company 15 years.

For the last ten years I usually go to lunch and pick up something to eat out of the deli, at this local grocery store. In doing so, I made friends with many of the ladies that work the counter there, especially Debbie. Now Debbie is an attractive woman, but not drop dead gorgeous. She is 5’2, 140 or 145 lbs., with brown hair, and I know she is 55 years old, and is a widow of 3 ½ years. Her husband of 30 years had a massive heart attack while cutting the lawn back then. Debbie also has a very nice chest too, I would say 36D, and nice bubble butt, but also has that pouch many women have, at that age, in the belly area, but all in all, she is cute.

I usually stop there 3 or 4 times a weeks for lunch, and unless Debbie is off, she waits on me. She has a quick wit and loves to tease and flirt. Always has a smile on her face now. She was even like that when her husband died. I believe work was her refuge. I always would ask how many men were lined up at her door, dying to take her out? She would just giggled and say, oh, there is a few, but I keep the door closed, waiting on that special one, to come a knockin. She would always ask too, wheni was going to take her to lunch, and I would always laugh and say, when you think you can handle me for lunch.

A while back, I stopped in on a Monday, and had the usual banter with her, and when she asked about lunch, I said oh hell, and said to her, how about tomorrow at this time. She said seriously? I said yes. She goes you are on. Then I saw a radiant smile fall on her face, like she just won the lottery or something. Now I know from past chats, she hasn’t been out with any man, except one, and he lasted two dates, but was so full of himself, she couldn’t stand to look at him after the second date.

The next day I got to the store at noon, and Debbie was near the exit door, and waved to me. I went up and hugged her and asked if she was ready, she just nodded, and we left for this little diner that was two blocks away. Lunch was great, and the talk was even better. We really got to know one another. When her husband died, I did go to the funeral, and when it ended and people were leaving, she made a special effort to come up and give me a hard hug, and kissed me on the cheek and thanked me for coming. We talked about family life and she asked how being single was going. I told her it was good, but did companionship. She said the same thing, and now isn’t sure she could live with another man, or at least not get married again. I told her she should be dating and she said, she would, but it is hard to meet good guys. The one’s she has met want to get married, or live together, and she just doesn’t want that, unless he was the ONE.

We left the diner about ten to one, knowing she only got an hour. As we were walking back, I thanked her for a wonderful time. She said it was nice and wouldn’t mind doing it again sometime soon. I said, yeah, I would like that too, and then, for some strange reason, I leaned down and kissed her on the lips. She didn’t back away either, and when our kiss broke, we acted like it was natural. As we started walking, I asked if she wanted to do lunch again on Thursday, and she said really? I said, yep, this was fun. She said sure, but where this time. I said, how about I pick us up some fried chicken and do lunch at the park, if it is nice out, otherwise we’ll wing it. She said it sounds lovely.

That Thursday, I arrived about 15 minutes early to picked up some chicken and these big fries called JO Jo’s. Debbie was the one who waited on me. I asked for two breast, and she said yeah, you look like a breast man and I asked what she wanted , and she picked thighs, saying she was a thigh girl, which I said yeah, you look like a thigh woman. She just winked and said, wouldn’t you like to know. I got us some iced tea’s, and checked out and waited for her.

We drove over to the park, and surprisingly, there was no one around, for a warm June day. I said this is perfect, no one to bother us, and no screaming kids. She said, what, you don’t like kids? I said I do, but not when they are screaming like little banshee’s. We each have a couple of grandkids, so we do know what little one’s are still like. She said she loves her grandkids, except when they are acting up and don’t listen. I agreed with her on that. She was asking why I don’t date, and I said I really haven’t decided if dating is right for me, or just go out for casual fun. She said, oh, for casual sex then. I laughed and said, well yeah, but that hasn’t worked out to well yet. She said she sometimes thinks she would like to find a nice guy, go out, then maybe get busy in bed, with no strings attached to it.

We finished eating and cleared up the mess and I said we still have 30 minutes, would you like to walk for a bit, and she said sure. We walked, and for some reason, I just took her hand in mind, like we were on a date. She looked up at me and just smiled. Then I bent down and kissed her again, first lightly on the lips, and then pulled back to gage her reaction. Her eyes smiles, then her lips formed a smile, so this time I went in for another. As our lips met, we both parted them, and let our tongues explore each others. It turned into a long passionate kiss, and as we kissed, I pulled her in close, and could feel her breast mash up against my chest. They were definitely full, that’s for sure. I am pretty sure she could feel my cock, which was now hard, pressing against her stomach area. We stayed kissing for a few minutes.

When the kiss broke, all I could say was Wow, and so did she. I told her she was the first woman I have kissed like that in almost 3 years, and she said it has been over 3 and half for her. I told her that she was a wonderful kisser and she said the same back to me. She then asked, why so long, and I told her how the last two years of marriage, my soon to be ex, lost any desire for sex in any form. She was going through the change of life and what ever pill they had her on, killed any drive she may have had. Debbie said she can understand that, and said, the change of life is a bitch, and thank god I am through with it. I also told her that the ex enjoyed sex until after we married, then it started to decrease as time went on, and her bitchiness got more and more. Which is the main reason I left. I could do no right by her, even though I tried. We even went to consoling, but that didn’t help either. Debbie said she and her husband had a wonderful married life, and the sex was always great.

As we started back to the car, she asked if I could do her a favor, and I said sure, what is it. She said her computer, at home, somehow got a virus and now she can’t even go online. I chuckled, and said you really have to lay off of those porn sites. She laughed and said, but why, it’s a good way to pick up new tricks to use. I said, my my, you are a bad girl aren’t you. She laughed and said, wouldn’t you like to know. In my mind I am thinking, oh hell yeah I would. I said I could come over Friday evening, but she said she has to close, so I said how about Saturday morning after I go into the office for a bit. She said that sounds great and that she is usually up at 7:30 or 8 on her day off. I said great, I’ll be there then.

As we got to the car, and I opened her door, I leaned in once more and kissed her, and she kissed me back, with her arms going around my neck and mine around her waist. This kiss also lasted a few minutes. When we broke, she said, damn, how am I supposed to work now. I said, yeah I know. My cock was so hard now, and I am betting, she was quite wet. As we drove back, she wrote down her address and number for me, and I gave her my number. When she was getting out, at the store, she leaned back to me and kissed me again and said she had a great time today, and hoped to see me again tomorrow, at lunch time. I told her I probably wouldn’t be in, since I had to meet with a client. She gave a little pout and said well, then I guess I’ll have to wait until Saturday.

That night and Friday night, all I could think of was Debbie, and how much I wanted to be with her, sexually. I even stroked my 7 ½ inch cock thinking of her. Since neither of us was active sexually, I am sure we’d cum within minutes of doing anything. I was hoping she was laying in bed right now, using a dildo, or something, to get herself off too. That would be fun to watch, I am sure.

I was up at 5am Saturday, shaved and showered, and even though I don’t have a lot of pubic hair, I trimmed it back some. Before I was married, and dating another woman, she got me in the habit of shaving it all down there, but that can be a chore, and after meeting my wife and getting married, I quit doing it. She said it didn’t look natural shaved. Of course, her giving a blow job was usually out of the question. She usually had to be drunk to do that.

I left about 5:30 and headed to the office, and just before I left, I took a little blue pill with me. About 5 years previously, I was having trouble getting it up, so the doctor prescribed that, but I really think it was because I just couldn’t stand the bitching at home anymore, and that caused the ED. I got to work at 6am, and finished up a report for a client pretty quick. I popped the pill about 7am, and just waited around the office until about twenty after, and said oh well, I am going over and hopefully she is up too.

I got to her place, which was a nice house, in one of those well groomed neighborhoods, about 20 minutes from my work place. I pulled in and got out, went to the door, and rang the bell. I waited about 20 seconds, thinking maybe she wasn’t even up yet, and then the door opened. She stood there, wearing a wine colored silk night shirt, that just barely covered her ass. The top two buttons were undone, and I could easily see her cleavage and her nipples were poking out the material. She said, wow, I didn’t think you’d be this early. I apologized and said I could come back later. She said bull, come on in and said, I must look a mess right now. I said you look absolutely gorgeous just like that.

She guided me back through her home to the kitchen island and asked me to take a seat, then asked if I wanted any coffee, which I said please, that would hit the spot. She went to the cupboard to get me a cup and had to reach up to get it. When she did, her shirt lifted with her and exposed her ass, which was covered by a red, laced pair of panties that did not cover much. Seeing that made my dick twitch some. She had to know I could see it. Then she turned back around and as she did, I made it seem like I was looking around at her family room, which was off the kitchen area. After she poured me a cup, she fretted about her appearance, and I said you look fabulous, and if I may be bold, very sexy. She blushed some and thanked me. She said she didn’t expect me here so soon and I told her I got done with what I needed too, and figured you may be up already. She laughed and said she was up at 6am, but was just lounging around reading. I said I like how she lounges.

I was wearing only tan cargo shorts and a t-shirt, very casual like, and black silk boxers. She said that may be she should come over my place tomorrow morning and see how I lounge around. I said that would be fine with me, and I usually just wear boxers around the house. She goes, mmmmmmm, sounds even better. We both laughed at that.

I was sitting on the end of the island and she came over by me and stood there, while we drank. She said I have to tell you, I could not get those kisses out of my head these last two days. I told her that was all I could think of too. Then I stood up and took her in my arms, and kissed her passionately. Our kiss lasted for what seemed like hours, but was actually or a few minutes. My hands explored her back, feeling the silky material, but was wondering how her skin would feel. She was doing the same with me, but also pulling me in so we had no room between our front sides and I know she could feel my erection.

When she broke from the kiss, she asked, what do you usually wear to bed? I said, boxers, and in the winter, a t-shirt too. She said, mmmmm. She then surprised me when she said, well, since I am in my nightwear, you should be too. I looked at her and asked, really? She said why not, might as well be comfy before you work. So I stepped back and took off my t-shirt, and put it over the chair, then I undid my belt, and unbuttoned my shorts and let them hit the ground, and stepped out of them. I also removed my sandals. She stepped back and saw I had on black, silk, boxers. Then she came back in and just before we kissed, she said very nice, and very sexy. We kissed again, but this time I let my hands wander down to her ass, and squeezed both cheeks, and as I did, she moaned in my mouth.

After we broke from the kiss, she looked down at my boxers, and could see my raging hard on, but didn’t say a thing. We were like two teenagers doing it for our very first time, and not knowing what to do. Finally, she grabbed my hand and said some on, let’s get the computer taken care of. Here I am, with this beautiful lady, and we are scan’tily dressed, and she worried about her computer. I said ok, let me grab this CD and then off we went. She said her computer is in her bedroom. My mind was racing now, and wondered if I would even get close to fixing it.

Once in there, the desk was right across from her bed, and she booted it up. I sat down and inserted my CD, which would sniff out any virus. After a few minutes, the program did its chore and I found it. I then removed it, and went into the root section and made sure it was gone. Then I opened her browser to see if it left a cookie, which some do. I saw the cookie and removed it and then looked to see if any more were around, and that’s when I saw what she looks at, and was surprised. She logs on to Sex Stories dot com a lot. I looked up at her, which was just off to the side of me, with her hand on my shoulder, and said, oh you naughty, naughty girl. You like the site too? She blushed and said, well yes. I said me too. Some of the stories are out there, but most are written quite well, and very erotic. Theni asked, do you ever submit any stories? She stood there for a second, thinking how to answer, then just came out and said yes.

I asked what her pen name was for it, and she blushed again and didn’t answer. I said oh come on, maybe I have read some of them. Finally, she said it is Swing Gal. I said no way, I have read those. You are an amazing writer too. You really know how to capture a readers attention and are very erotic, which is what we look for, when we click on one. She said thank you, I try, and I really enjoy writing them. She asked if I ever wrote any, and I said I have, told her my name, but she said she hasn’t got to any of those yet. I logged onto the site, and then logged onto to my name, went to my stories published and clicked on one. Most of hers involved swinging, and a few of mine did too, so I picked one I thought she may like. It popped up, and I grabbed her hand and said come sit in my lap and read. She giggled and said, well, I don’t think we’ll need to worry about anything popping up, because it’s already up. She sat right down in my lap, wiggled her ass a little, which now had my covered cock resting between the cheeks of her ass.

She started reading, and as she read, she was moving around in my lap, and I could tell when she was getting to the sex parts, because she squirmed around a lot, which was driving me crazy. As she finished, she turned towards me and said, wow, I never knew you got into swinging. I said I had no idea she did too. She said that her husband John, and her started swinging about 10 years before his death. A couple they were friends with, introduced them to it, and they found they really enjoyed it.