Dear Diary: My Older Women

When I was 18, I worked with a lot of women, mostly older. Aging from my age, up to their 50s and even 60s. One that I really enjoyed flirting with and talking to was in her late 40s. A gym rat, she was into fitness competitions and was fantastically fit. We would joke around, but I didn't really know what I was doing, and still had my v-card.

One day, she had asked a couple of the guys at the front if someone could help out moving some of the equipment in her home gym. Her husband was a trucker, and was often away. Goodness knows why she didn't ask him, as he was big and burly, but I suspect she may have had ulterior motives.

I jumped at the chance.

We planned it for our next day off. I helped to move what needed to move, and we decided we would go for a hike, locally. We did so, and came back to her place. She offered the hot tub to relax in afterwards, I had to say yes.

She went to her bedroom to change into her bikini. I teased I would be in a few minutes, she said, no you won't. and made a point of closing the door. Damn.

I climbed into the tub, and she came out wearing a gorgeous teal bikini with half of her toned ass hanging out. She climbed in, offering me a beer as she did so. not sure if she knew I was technically under age, but it went over easy enough.

It took about 5 minutes before I had my tongue down her throat, and she put up only token resistance. Soon enough I had her top off and I was exploring her tits while we kissed. Soon we were naked. She expressed concern that the neighbours may see her, so we went inside. She made it a point that we not do it in her bed but in the spare room in the basement.

It was there I lay with her, and she sucked me until I came in her mouth. It was my first blow job, and it felt weird to have my cum spit back out on to my thigh, but I didn't care. She wasn't about to swallow me, but I didn't mind. We fucked for about an hour, and then decided we would call it quits, because the kids could be home from school sooner than later.

I moved into the spare bedroom in the basement while I went to university, and paid $200 a month to live there. All the food was included, and we would have sex quite often for the first couple months. She started to feel guilty after a while, so we called it quits.

The next time was when I was 20 she was 33. It was a 1 night stand. We met online. We chatted a bit, and she invited me over. I spent a few hours, we cuddled, fucked, cuddled some more. I didn't stay the night. That was the only time for us. I think her name was Jen, and I remember leaving my watch at her house.

I had a 3 month relationship with a 35 year old when I was about 21. We will call her G. Again, we worked together. We didn't really even get along at first, I found her a bit abrasive. She was attractive blonde hair with wide hips and a strong core from riding horse. One night a group of us went out for drinks at the local pub. I had received a tip from one of the girls that G was interested in me, and so I thought I may as well see what I could do.

I made sure to sit beside her at the table, and we chatted and bantered for a while. Once it was time to disperse, she asked if I wanted to go for a walk with her along the water. (I may have invited her, I can't remember). We agreed, She said, lets stop at my car first. We did, and I watched her take her bra off and slide it through her sleeves, and toss it into the car. "So much better". She had me. I pushed her against the jeep, and we spent the next few minutes tongue wrestling against the side of her car. Then we walked along the water, holding hands, and started a 3 month relationship of hanging out, sex as often as we could, and working together.

She rode horse, and had fantastically strong thighs. sweet perky breasts, and a nice wide ass. She loved me going down on her, but didn't like sucking cock. At one point, we had been fucking from about 11 til around 3 in the morning, and she actually fell asleep on her elbows and knees while I was fucking her from behind. I tried to sneak a polaroid of her, but she was just barely asleep and put a stop to that idea, very fast.

She was also married, but was in an open relationship and while it seemed a bit weird to me, I liked her husband (also worked with him) and wasn't about to say no to frequent fliers with his wife.

It was a bit scary when one afternoon we had just finished up and were laying on my bed cuddling, and I could hear my parents pulling up in the driveway to visit. It was unexpected. She got her clothes on as fast as she could and snuck out the back door. She was fun.

I'd also had a girlfriend at that time, she was my age. I was a dick and messed around on her. I remember one day, I had spent the night at the girlfriends, and we messed around in the morning before she went to work. I went home, and G came over, and we messed around. That night, I had invited another girl from work over, whom I know had a crush on me forever. That was the first time I'd had 3 different women on the same day. Fuck was I tired.

T was another woman at work. She was in her mid 40s. Tall, about 5'11". Italian, with dark hair, shoulder length. Always smiling, she had a great attitude. She also had great curves. A nice wide ass and big but not too saggy tits as well. She had 2 kids of her own. A daughter, who was about 13, and a son, who was about 18.

Every time I'd see her in the hallway, I'd tell T how good she looks, or start some kind of small talk. It took a few months, but, she was down in her office in the basement when I was finishing up shift. I popped in to say hi, and she was rubbing her neck, complaining about a loong day. I wasted no time, I stood behind her and started rubbing her shoulders, and a bit of a scalp massage. Once I got a handful of hair, yanked her head back and started sucking on her neck. Thats when I knew I had won.

After that, every Sunday morning, we would meet up at work in an empty room and spend 15 minutes of just pure, NSA, fucking. Then we would go back to work and nobody was the wiser (as far as we knew). I would see her son at work once in a while, and we would be chatting, and all I could think was...dude, I plowed your mom this morning.

T was fun, she was loud. Loved me eating her out, then we would fuck for a bit, and I'd always finish inside her. Such a good "job".

That was the end of my older women days, so I thought. I was married for about 8 years, when I found out my wife was having an affair with my best friend without me knowing. They had fallen in love, and so it was the end of the marriage. I moved out, and into a basement suite in a house where the landlady was a 58 year old Polish woman and her 33 year old personal trainer daughter.

I had hopes of seducing the daughter, but I also didn't want to shit where I eat. She had 2 kids very close in age to my own, so it was a great arrangement. Then one day I got a call saying that they had to put the house up for sale. It was difficult to hear, I'd only moved in about 4 or 5 months prior. The house sold within a week of going on the market, and I had 3 months to find a new place to live.

The daughter and her two kids moved upcountry, leaving me in the basement, and the older woman (Lets call her K) upstairs in a huge place by herself.

I'd mowed the lawn and cleaned the gutters and did what I could to help keep the place up. About a month before I had to go, I had sent her a text, offering to go out for dinner and drinks if she wanted some company.

She jumped at the idea, and she dressed up as if it were a date. It kind of was, and she talked my ear off. Very interesting stories, an amazing life story. We talked about her past, and her partner had died of cancer about 10 years prior. She hadn't been with anyone in the last 10 years!

Over the next couple of days, I sent some flirty texts, each one becoming more risquee than the next. It culminated in an indecent proposal, offering her some company for a warm body and someone to take care of her needs, since it had been so long.

I should point out that K had been doing yoga for the last 10 years and was firm and fit, in fantastic shape.

After I sent her the text message, I sat and waited at the top of the stairs, at the door leading to her place. She was talking to herself, she couldn't believe what she had read. She even called one of her friends at work and told her about my proposal. I could sense that she was very conflicted, but she talked about how thirsty she was. I knew I was in. That night, I invited her down for drinks and a movie. She declined, saying she was already in bed, and had just started to watch something. I told her I'd be up in a minute.

I came upstairs and we sat in her bed together watching who knows what for about half an hour. She was shaking a bit, and so I didn't pursue anything. Two days later, she sent me a text saying she picked up a movie from the library, and asked me if I wanted to watch it with her.

I did, and we lay in bed watching for about 20 minutes. Then I made my move.

I leaned over and I kissed her, softly. Then I reached behind her head and grabbed a handful of hair, and kissed her hard. Her tongue pushed into my mouth and soon I had rolled her over onto her back and was straddling her while we kissed. It didn't take long before I pulled her pants off and had my head buried in her thighs. I don't know when the last time she had had an orgasm like that but her whole body was shaking and she was near tears. Once I had made her cum, I took her shirt off and sucked on and played with her nipples while I teased her pussy with my cock. It took a bit, but I slipped inside her with a bit of work. She was wet, but was so tight that it almost hurt her to have me inside. It didn't take long, and soon I was thrusting hard with her on her back, knees up to her shoulders. We went on for about half an hour. When I had finally climaxed, we lay in the bed, I held her, spooning her from behind, for about 20 minutes.

It took 2 days until she asked me to come upstairs again. I was also dating someone at the time, and I was doing shift work so I wasn't home every night. During the last week before moving time, I snuck upstairs at about 4:30 in the morning, and crawled into bed. She had no panties on, and was wearing a nightgown. We fucked for an hour until she had to get ready for work, and I went back downstairs to my suite.

She asked me to her new place to help set up her bed and christen the new place. I declined because things were starting to get serious with the girl I was seeing, and I wanted a clean break. She confessed that I'd awoken something in her that she had managed to keep bottled up for the last decade. She couldn't fight it anymore, and decided she needed to find someone again.

I don't know if its a good thing that I pushed her out of her solitude and back into finding a partner. I hope she finds somebody, because she was very sweet and brilliant, and loved getting it from behind. She sucked great cock and had no qualms about running her tongue up the back door and wherever else she pleased while she had me in her mouth. Sometimes I feel like sending her a message, but I think it best to let this sleeping dog lie.