Milf to Cougar

Sexy young milf moves in across the street, but at 10 years old all I could do was fantasize. But years later the Milf becomes a Cougar.

When I was around 10 years old the house across the street from ours had been for sale for over a year. I had been hoping once the old couple that had lived there forever had gone that a family with kids my age would move in, but I turned out to be something much better than I could have ever dreamed of when a couple moved in and though they had no kids, I’d soon learn I’d hit the jackpot. Brenda who was in her early 20’s and was the sexiest woman I’d ever seen in my short life. Her husband looked like he’d be old enough to be her father. They both turned out to be really nice but the husband Jerry was kind of a second thought to me right away. Where Brenda became my obsession. They moved in on a weekday so most of the neighbors were at work, so I elected myself the ambassador of the neighborhood and went over to welcome them to the neighborhood. Brenda was absolutely perfect. She was about 5-10 with long shapely legs, a nice peach shaped ass and pear shaped tits. I’d suddenly decided that I loved fruit…lol. She had tanned skin I learned later was from her part Indian heritage and she had long dark brown hair and beautiful brown eyes. Her full pouty lips would over the years start to really turn me on. She had a perfect 36C-24-36 body and just an air about her that even at my young age seemed to tell me she’d be a very classy lady until she got in the bedroom, and in there she’d be a total slut.

Her husband was a couple of inches shorter than her and a little chunky, and was starting to lose his hair. I got the impression very quickly that he was only being so nice to me was because I was a kid. I felt like he wanted to put on Aires with grown up’s making sure they knew he was rich and showing off his hot young wife, the same way he showed off his new Corvette and his Hummer. I’d overheard some of the neighbors comment about how the way he showed off those cars told them he must have a very tiny dick. As I got older I figured out what they meant and eventually learned that they’d been absolutely right about his tiny pecker. I couldn’t believe my luck when I saw they’d taken the front bedroom as the master. From my bedroom window I had a perfect view into theirs, and they weren’t fans of closing the drapes. And Brenda apparently loved very sexy and very sheer lingerie. I was jerking off almost every night thinking about Brenda and during the day finding any excuse to be around her. If she went to the market I was there to help take her things in, if she was planting flowers I was right there helping. Any excuse to be around her I was right there. I’d also started being there when she didn’t know, as I was sneaking over and peeping in her bedroom & bathroom windows. That was where I learned that she masturbated a lot, and when a friend from her old city came for a weekend that Brenda was also into girls. I’d secretly spied on my sister a lot and had seen her with another girl on a couple of occasions. But they were neither anywhere near as hot as Brenda and her friend.

This all went on until for a few years as an obsession until I started fucking my older sister. I was still watching Brenda and jerking off thinking about her, just not as often. I’d been fucking my sister for 2-3 years until she left for college and I got my drivers licence and started dating. I was tall and considered nice looking and between having a big dick and the experience I’d gained from years of sex with my sister I was doing pretty good with the girls. And well having a really cool car didn’t hurt. I’d still help Brenda with groceries and stuff if I saw her, but was seeing her less since I was driving. Brenda had always dressed kind of conservatively but I suddenly noticed she was dressing a little sexier, and was floored when I came home and she was washing her car in a pair of shorts and a bikini top. Not long after then was when I learned she and Jerry had separated and she’d filed for divorce. But I tried to put that in the back of my mind. I’d started dating the local preachers daughter. She was quite conservative where I was not so much. Lynn dressed ultra-conservatively and wore her red hair up in a bun and was forbidden to wear any make-up. But I knew under all of that was a very sexy redhead with a rocking body just begging to be seen. At 5-8, 120, 34-DD-24-35 she was sexy as hell. And I knew she was tired of the whole deal of hiding that sexy body from the world.

Soon after we graduated from High School and we were both 18 we got married. We’d expected that our parents were going to freak out. But my parents thought being married to the preachers daughter would calm me down and her parents thought it was nice that she was marrying into a wealthy family that gave her stability. We lived in an apartment at first but my parents soon divorced and neither really wanted to stay in the house so they arranged for us to buy it. So there I was living across the street from Brenda again. In the year I’d been away she’d changed her hair style and was dressing sexier and just seemed to be acting younger. But Lynn and I had made some changes in that time also. We’d gotten into the swinger lifestyle. She still had to dress conservatively in our small town to keep up appearances, but at home and when we were out of town, which was almost every weekend she was a very different and much more adventurous person. We’d gotten started after taking some nude pictures and after seeing them for the first time realizing how hot she was. So she started trying to show as much of her body to as many people as possible. This was around the time we started having threesomes with some of my friends which lead to us getting into wife swapping and Lynn realizing she was also into girls. So lots had changed for Brenda and me in the year I’d been gone.

I guess Brenda decided to return the favor of me welcoming them to the neighborhood and came over to welcome Lynn and me. Lynn was wearing a low cut top and no bra and her hard nipples were poking out on the thin material of her top, and she was wearing some pretty short shorts. Brenda was wearing shorts as well and a tight fitting tank top without a bra, the cold from the AC bringing her nipples to full attention as well. I couldn’t help but notice their eyes moving over each other’s bodies and it was clear they liked what they saw. We went into the family room and had a drink as the girls got to know each other as if I wasn’t even there. And on several occasions complimented the other’s body. As they had a look like they wanted to jump each other’s bones. But eventually Brenda left and she and Lynn gave each other a very intimate and long hug as she left. Lynn wasted no time in saying normally she wasn’t into older women, but she’d do Brenda in a second, and in the same sentence asked if I’d ever fucked Brenda. I said I hadn’t but had spent half my life fantasizing about it. Lynn with a sexy grin said to believe her when she said that given half a chance Brenda would fuck my brains out, then said and I’d be crazy to pass it up. I commented how I thought it looked like they were into each other as well. Lynn laughed and said you think and said she had no doubt that Brenda was going to try and put a move on her within a week.

A few days later Brenda called and asked if I could come over and help her with something. When I got there she told me on the intercom to come in and said she was upstairs. She was wearing a very sheer housecoat and said she was just getting out of the shower when her bedroom lights went out. I went in and tried a lamp and it didn’t come on and when I turned she was about a couple of inches away from me. She raised up and started kissing me as she let the housecoat drop to the floor leaving her totally naked. Her hand went right to my belt and she started undressing me. She said she’d wanted me for years. I told her I’d been mentally fucking her ever since I first saw her and she said she’d kind of figured that, and told me she often fantasized about me being just across the street jerking off as I thought of all the nasty things I wanted to do to her. I asked if that was why she always left the curtains open. She said yes, that it turned her on knowing there was a chance I’d see her naked. About then she went to her knees and was saying how often she’d thought to herself that I’d have a nice cock, but that it was even bigger than she’d imagined. She started sucking me off, then paused and asked if Lynn sucked my big dick for me, I said that she did and that she was very good at it. She sucked me some more then asked if I’d ever fucked Lynn in the ass, saying she loved taking it in the ass. I said yes and so did Lynn.

Then I just came out and said there wasn’t much Lynn hadn’t done and that she’d done everything I wanted except one. Brenda said what’s that, and said she bet she’d do it. I said the only thing Lynn hadn’t done that I wanted was to see her sucking on Brenda’s tits and eating her pussy and that I wanted to see her do the same to Lynn. Then said that Lynn had already said she wanted to lick every inch of her body. And that she wanted to watch Brenda ride my cock and then eat my cum out of her pussy. At that she led me to the bed and I finally got to fuck that pussy I’d been fantasizing about as a kid. She screamed like a whore with each of her several orgasms, and when I was ready to cum I pulled my cock out and shot my load all over her, from her face to her tits and all over her stomach. Then said I bet she would love to have Lynn lick up every drop of my cum off of her. She quickly agreed and asked if we’d ever thought about having a threesome with another woman. I said you mean more threesomes with more women? She seemed surprised when she learned we’d had threesomes and I’d told her with both girls and guys. It assured her she’d be surprised at the experiences we’d had. That seemed to turn her on, saying anything we hadn’t tried she’d like to help us experience it. This was before the term cougar was heard. But that would certainly fit the definition now. A woman in her early to mid 30s taking on two teens as her cubs. I later learned that she’d been dressing up to show off her sexy body and going to clubs and bringing home the youngest guys she could find while I’d been away. But keeping her bi desire still closely guarded. Back in the 70s being thought of as a slut or cradle robber wasn’t good, but being outed as Bi or Gay was still a big deal.

When I got home that night by the length of time I’d been gone and the smile on my face she knew I’d fucked Brenda. Her only regret was that she wasn’t there to join us. We decided to play it cool for a while so we met Brenda at a Hotel about 50 miles away from our little town. I let the girls have some fun first. It was like a dream come true watching my sexy wife and the woman I’d fantasized about for over a decade since I was a kid exploring each other’s amazing bodies. Sucking each other’s big tits and eating each other’s pussy, fucking each other with various toys. Then it was my turn to join in, but this time Lynn just wanted to watch, she knew how long I’d fantasized about Brenda and that she wasn’t there to see our first hook-up. Brenda took her time licking & sucking my balls then taking more and more of my cock down her throat, but still not able to take it all like Lynn. I fucked her from behind and then with her legs over my shoulders. And finally I fucked her in the ass, which was something fairly new to her. But she had her biggest orgasm of the night with my cock buried deep in her tight little ass. But I pulled out before I shot off and rolled her over and straddled her putting my cock between her tits. I had to explain to her to press her tits together as this too was something new to her, having never had her tits fucked despite how perfect they were for it. Soon I’d coated her tits in cum and Lynn wasted no time in licking them clean. Brenda couldn’t wait for me to cum on my wife’s tits so she could lick her clean..

It looked like Jerry had been one of those guys who stuck his cock in her pussy and shot his load and that was it. She said the only orgasms she had when they were together was when he’d on occasion he’d watch her masturbate. Lynn introduced Brenda to something else she had never tried but it turned out to really turn her on. She ordered a pizza and Lynn answered the door in a totally see-through housecoat that didn’t have buttons or a belt. The guy could already see right through it, but as Lynn went to get the money out of her purse that was across the room under a chair she let it fall open. About then Brenda came out of the bathroom in a garter belt & stockings and see through bed jacket that only went above her waist and like Lynn’s was wide open. She opened the pizza box and commented how good it smelled, looked at Lynn with a sexy grin and said that was going to be the second best thing she’d had to eat that night. The way they were dressed, her comment, and the big double headed dildo and strap-on laying on the bed made it clear they’d had sex with each other. But when Brenda planted a big wet kiss on Lynn’s mouth as she squeezed her ass really sealed it. I’d bet money that that guy could have cut diamonds with his cock about then he was so hard. As he left he thanked them for changing his whole day, and explained that the whole day had sucked, but that that delivery had made up for it. Brenda wanting to screw with him some more said well sucking can be good too.

Brenda said she’d always wondered what it would be like to do something like that and now that she had she had to say it was one of the biggest turn-on’s ever. I’d been on the balcony watching and when I came in told her she should have been there the night she fucked a pizza delivery guy. She wanted all the details and said we were going to have to do that again the next night as we were staying the whole weekend. She didn’t get to fuck the guy from another pizza place but he did feel her up and suck on her tits. Lynn went outside and watched with me and for the first time got to see what I’d been seeing and found that voyeurism could be almost as hot as exhibitionism. Lynn and I continued to go out of town almost every weekend and Brenda usually went with us about once a month. We couldn’t get her to go to an adult bookstore with glory holes, but we did go to an adult theater where Brenda & Lynn stripped and let a bunch of guys watch them kissing & sucking each others tits and eat each other’s pussy. And Brenda gave me a blowjob and I shot off on her tits and Lynn licked up all of my cum off of Brenda’s tits as a bunch of guys watched. And we had lots more hot experiences with Brenda over the next few years.

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