For about a year now my wife Olivia, a really hot cougar/MILF, has been getting fucked once a month by a young man half her age, with an unusually large prick. She loves it, he loves it, and I’m okay with it, for reasons I will tell you about.
It all started with my wife’s niece, Alice, who lives and works in a nearby city. She is in her late 20s and is an unusually attractive lady, tall, slim, and shapely. About three years ago, Alice’s long-time best male friend, Ross, finally became a “friend with benefits.” The two of them had not hooked up previously because neither of them wanted to risk their friendship on an affair that might or might not pan out. But then Alice began hearing from some of her female friends that Ross was unusually well endowed, and that he knew how to use what he had. The word was that his cock was nearly nine inches long. Alice was intrigued, but resisted for a time her impulse to bring up the subject with Ross.
But one evening, over a dinner accompanied by a liberal amount of wine, she found herself probing and even teasing him a bit over what she had heard about his manhood. Ross took it in good spirit, and admitted that his endowment did indeed measure up to the rumors she had referred to.
When I got divorced and moved to a new neighborhood two years ago, I met a lady named Letitia, who hung out at a local bar which I also frequented. She was a good looking, mature woman, who I guessed to be in her late 40s or maybe early 50s. She was pleasant to talk to, and we often sat at the bar and chatted over a few drinks. Over the course of a few months we became good friends. She was really a hell of a nice lady, widowed but not bitter, and very outgoing.
I often wondered why she didn’t have a man. I couldn’t see a gray hair on her head, and no stretch marks or wrinkles, other than some very faint crow’s feet around the eyes. She had curly dark hair, blue eyes and a nice smile. She also had the prettiest pair of legs I’d ever seen, smooth and shapely. I told her several times that her legs should be on a billboard somewhere, advertising stockings or high-heeled shoes, but she just laughed. I sometimes heard other people making comments about her legs as well, even though her hemline never rose more than an inch or two above her knees.
I found her legs so attractive, along with the rest of her, that after a time I began to flirt with her a little. Since I had never seen her come in with a guy, I figured I had a good chance. Letitia knew what I was after, and she was good-natured about it, even seeming to enjoy the chase, though she would scold me gently whenever I suggested that she go home with me.
It was my 52nd birthday, and to celebrate, my wife Maggie and had I decided to spend the weekend in a hotel in the city. The plan was to spend two days having sex, going shopping and eating at expensive downtown restaurants.
We checked in early on Saturday, and as soon as we got settled in our room Maggie began to unfasten my pants so she could suck my dick before she rode me to a climax.
After she had done that, having experienced two orgasms in the process, my wife decided to pay a visit to Victoria’s Secret to buy some new lingerie. She asked me if I wanted to come with her, but I decided to pass, saying that I hoped she would model her purchases for me when she got back, and she promised to do so.
Maggie is a beautiful woman, five feet three and 115 pounds, with perfect 34B breasts and nipples that measure three quarters of a inch when hard, which they are most of the time. She is 51 years old but can pass for 35, and she still attracts a lot of male attention wherever she goes.
While she was at the mall, as she related to me later, a young black guy saw her looking in the window of the store and made his way over to stand next to her. As usual, she wasn’t wearing a bra, and her nipples were trying to burst through her tight white T-shirt.
My daughter and her boyfriend recently left the military and moved in with me until they could find good jobs and a place of their own. For me at 43, after living alone for several years, it felt good to have them. It felt especially good to have a man in the house again.
Within a few weeks my daughter indicated that they were getting close to having “an announcement,” which pleased me. Nate’s a great guy—good-looking and fit, with a great personality.
My daughter took a job working nearby which left Nate and me home alone in the daytime, since his job entailed several weeks of swing shifts each year. One day while she was working, after he took his shower he came up behind me while I was making breakfast, still wearing my sleep shirt and panties. I turned around and the towel around him simply dropped! We were about face-to-face. He tried to pick it up in a quick move and accidentally bumped my head. I fell back, but he grabbed me before I hit the stove and pulled me to him. His cock pressed into me, and wow, did it feel good!
My buddy Ron and I had cut the doctor’s lawn for a couple of summers, but last summer, after we graduated from high school, the doctor and his wife became our favorite customers.
Cynthia always teased us by bending over and showing off her fine ass and giving us views of the bottoms of her gorgeous tits through half-shirts and crop tops. One day she asked me to give her a hand in the tool shed. I was there in a flash, as Ron kept mowing. It turned out that she gave me the hand—in my shorts!
She wrapped her fingers around my quickly growing prick and said, “Mmm, that feels nice. Would you mind if I taste it?” I nodded, and she was on her knees in a flash, her big blue eyes looking up at me.
Three years ago I caught my wife in bed with a guy she worked with. After punching him in the face, I packed my shit and went to my mom’s, but she wasn’t home, so I called her best friend Gwen, who told me to stay with her till Mom got back from vacation. She said she’d love the company. (She’s a widow.)
It was nearly midnight, and Gwen greeted me at the door wearing a thin robe and not much else. I felt the kiss was a little longer than normal. I followed her to the kitchen and she got me a drink while we talked. When she leaned over, the robe gapped at the top, allowing me a full view of her tits. I had an immediate hard-on. When Gwen bent down to put some pots away, the bottom of the robe “accidentally” caught in the cabinet door. As she stood up, the robe was pulled open, exposing her 49-year-old body. Since she had a bottle of brandy in one hand and a pan in the other, she couldn’t close it until she sat the items down.
About six months ago my wife Nora went up to visit our daughter at college for a weekend. Originally we were both supposed to go, but there was a last-minute emergency at my business, and I was forced to stay behind while my wife drove up alone. When she returned two days later, she was looking a little guilty, and she said she had something to tell me. Leading me up to the bedroom, she began her story.
Nora and Kate, our daughter, have always been close—more like sisters in some ways than like mother and daughter, despite the 22-year age difference between them. When Nora arrived she met Kate at her sorority house. Nora had, as it happened, been a member of the same sorority back when she was in college, and as a former member she was welcomed and made much of by all the girls. She found herself being treated more like a contemporary than like an older woman, which she found quite flattering.
Because of my work schedule I’ve been going to the same laundromat every Monday for the last seven years. During that time I’ve seen all types of people in there, from weird to dangerous to downright sexy.
One person who usually showed up at the same time I did was a woman of about 47 named Linda. The first time I saw her I noticed her nice figure and sandy blonde hair. For a woman of that age she looked very sexy in a pair of jean shorts and a white top. I think she knew I was checking her out, because she flashed me a knowing, flirtatious smile as she went about her business.
After seeing her several times I got up the nerve to strike up a conversation with her. I learned that she and her husband had three grown children, and that she was actually a grandmother. When I told her she was too good looking to be a granny, she blushed and thanked me.
I don’t know why but I’ve always had an infatuation with older women. Back when I was just 18 I had a bad crush on a mature lady, a neighbor of ours named Evelyn. She was a widow in her late 50s, with long dark hair flecked with gray. She had a beautiful face for a woman that age, and I thought she might have been a model when she was younger. She had a medium build with a nice round butt. She used to walk around the countryside wearing a tweed skirt and followed by her dog. I guess she kept in shape by walking so much, and by working in her garden and her yard.
But all I knew for sure was she turned me on, and I wanted to fuck her in the worst way. She was always very friendly and cordial to me, but that was all. Then at one point she happened to mention that she liked chess. I quickly took up the game, and one day I suggested to her that we play sometime, and she agreed.
That got my foot in the door, and soon I was playing chess at her place every day. It was just chess, but I always left with a hard-on at the end of the evening, and I would jerk off repeatedly in my room once I got home. My lust for her was killing me, and I knew I had to do something, but I was very nervous and didn’t know how to go about it.
About a year ago, as I was changing the bed in our spare room, I found some adult magazines stashed between the mattress and the box spring. I questioned my husband about them, but he said they weren’t his. Next I questioned my 18-year-old son, who also denied ownership. I could see that he was holding something back, however, and after some more pressure he admitted that they belonged to his friend Kyle, who had left them behind the last time he stayed over. Kyle’s mom and I were good friends, and I didn’t want to get him in trouble, so I let the matter go.
A few weeks later Kyle came to spend a weekend with us. On Saturday morning, when I passed the spare room, I heard a strange noise from inside. The door was open a crack, and I peeked in to see Kyle lying on his back, naked, with his face smothered in one of my bras and a pair of my panties wrapped around his cock as he masturbated furiously.
Quite shocked, yet also, I admit, just a bit excited, I quietly closed the door before he saw me. But 20 minutes later, when he came out to go to the bathroom, I stopped him and asked him what he was up to. Before he could say anything I looked into the room and saw my bra and panties still on the bed. I went in to pick them up, but quickly dropped them when my fingers touched what could only have been semen in the crotch of my panties.
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