Lost virginity to a cougar

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It was summer of 1987 and I was a guy age 18 in-between my junior and senior year in high college. I was a nerd and never had a serious girlfriend – had a few dates, but kissing is the farthest I’d ever gotten before.

We lived in a normal suburban neighborhood and one day while riding my bike, a lady a few blocks down from us stopped me and asked if I’d like to earn some money during the summer helping with some chores around her house. We knew her – I’ll call her Mrs Robinson – and she was in her 40s, but my parents never socialized with her. I didn’t have a summer job and was excited about earning some extra spending money, so I said sure. That night I told my parents and they looked at each other funny but did not say no. Overhearing them later that night, I realized they wondered it was terrible that she was divorced – something that raised alarm bells in my family, but I was still encouraged to help her out.

The first time I went to help was just hanging and replacing pictures on walls. The second day, she had me clean the pool and the patio. Now those first two days, she was very nice to me – bringing me soda and snacks and was with me the entire time encouraging me on and giving direction. I remember I found it annoying. Now that I look back, she was like a hungry carnivore playing with its prey, and was testing to see how best to approach me. I also remember the risqué clothes she wore that I didn’t even think about – or probably wondered it was odd on an old lady.

That third day I went to help move furniture. Before I even started, she offered me a beer. I’d had beer before, but never had it offered to me by an adult. This is a cool lady I wondered. I drank it while she explained the jobs we would do. Finally, after 2 beers (she reminded me I was being paid even just sitting with her at the kitchen table drinking beer), we moved to the living room where we would move the sofa, love seat and a couple chairs around. There on the coffee table was a playboy magazine opened up to the centerfold. It was a blonde wearing a white bathrobe and she was pulling her underwear off to the side to expose her pussy – which was not shaven back then. Anyway, she noticed me staring, how could a 17 year old not, and asked innocently if I’d never seen a naked woman before. I lied and said of course I have. She explained how her ex husbands magazine still came to the house and she wondered I would like this centerfold. She said that when a woman pulled her panties to the side like that, it was an invitation to touch. That should have raised alarm bells in my head, but it didn’t. I was getting hard and wanted to pick up the magazine and look at the other pages, but of course, I didn’t. Funny now, but I was oblivious to her coming on to me and was just thinking how I could bring the magazine home to look at all the pages.

Again, I was a virgin and not quite getting this, but soon I had a stone hard erection that was not going down anytime soon, and was a bit uncomfortable. Mrs Robinson noticed and motioning toward the bulge in my shorts made a opinion about how I obviously appreciated the photo. She picked up the magazine, handed it to me, and told me to sit and enjoy, that I earned it after all the work I’d done. She then left but returned with a third beer and left again. I nervously flipped the pages – OMG, this woman was letting me look at playboy magazine and drink beer. This was a dream. She retuned wearing a white bathrobe just like the centerfold and was drinking some adult mixed drink I heard her make in the kitchen.

She asked if I’d like to see more playboy magazines and I said No. The situation felt very weird and odd, and I thought if this was some sort of test or setup. No way could I be this lucky and this is happening to me. I could not help but think my parents would burst through the door and I’d be in trouble. But the beer was starting to make me relaxed a bit. She was sitting in a chair across from the sofa and was talking to me. I don’t know exactly what she said, something about her exhusband, and men. But slowly I noticed she’d tug at the bathrobe, or move a bit, and the robe would open just slightly revealing a bit more cleavage and leg. My erection was still there but I had the magazine in my lap to hide it. Soon one of her nipples was showing and below was open enough that I could see she was wearing white lace panties. Despite all my attempts to keep my eyes focused on her face, they darted between her tits and her visible panties. For me, she had transformed from some old neighbor lady, to that playboy centerfold.

She noticed me looking too. She said the playboy magazines are great to look at, but seeing a real live naked woman in person was so much better. And she asked me if I would like to see her naked? I didn’t say a thing and I did not have to, because she did not wait for an answer, and stood up and let the robe fall to her feet. She had amazing breasts, but what did I know, and I could see the dark patch of public hair through the lace undies. She asked if I wondered she could be a centerfold, and I said Yes to be nice, although she really could have been. But god this was so uncomfortable for me. My heart was racing and part of me wanted to touch her and part wanted to run home and hide in my room. Then she said what was even better than seeing a live naked woman, was getting to touch one. She knelt in front of me and told me I could touch her breasts. I swear, I was still thinking this was not real and this is when the gig would be up. Police or parents breaking down the door as soon as I touched them. But that did not happen. As weird as this was, my hands reached out and obeyed. I played with her nipples and breasts for a long time and she just smiled at me like she was watching a child playing with a new toy. The magazine had slid off my lap and there was a wet spot on my shorts. She touched the wet spot and played with the tip of my dick through my shorts while I continued playing with her nipples. I moved uncomfortably in my seat. For the next few minutes she played with my dick through my shorts. I could not believe this was happening, but there was no way for me to stop it. Finally she unbuttoned my pants and unzipped my fly which relieved the pressure. She pulled my underwear down a bit to expose the top half of my dick. I didn’t do or say anything as this felt better than anything I’ve ever experienced before. She removed my shoes and when she tugged at the pants and removed them and my underwear, I wondered my heart would explode. There I was sitting on her sofa with my bottom half naked and my hard dick in full view, with a mostly naked woman kneeling in front of me. I wondered I was gonna die. Then she pushed me back so I was leaning against the back of the sofa and told me to relax as she could see how tense I was. My dick was throbbing and she stroked it with her fingers and rubbed the precum that formed on the tip around. Then she went down on me and sucked. I had absolutely no control and within a minute I was unloading a large amount of cum in her mouth. She did not flinch, never stopping, and swallowed the entire load. She looked up with a smile, that only now I realize was comical awareness of my inexperience and inability to hold out longer. But she then continued sucking – it was painful since I was hyper sensitive – but it subsided and after a few minutes, I was rock hard again.

She stood up and took my hand and without saying anything led me to the bedroom. She took off my shirt and instructed me to lie down. She took off her panties and climbed on top of me, straddled my head, and lowered her pussy onto my mouth. I’d never tasted pussy before and it was amazing. She was warm and wet and I licked erratically and crazily and she moved back and forth across my tongue. She let out a loud moan. I did not know it at the time, but she had cum. She lay next to me for a while and then told me to get off the bed and stand up. I remember thinking she was kicking me out having realized she’d made a terrible mistake and was gonna call my parents, but that was not it. I nervously watched her from the side of the bed and she got on her hands and knees and then down on her elbows and raised her ass up so that it was sticking right in front of me at the perfect height for me to enter her pussy with my once again pulsating cock. She said something to the effect that if a naked woman gets in this position, no man cannot fuck her, that animal instinct kicks in and no matter what she looks like, her height, weight or color, any man around will stick his dick inside her. I wanted so badly to do that, but also worried about getting her pregnant, but told myself I would pull out. I still had that wondered in my head while I was inserting my dick inside that wonderful hairy wet pussy. I did fuck her like a wild animal and I lasted a bit longer this time, not by much, but a bit. She let out a little yelp with each thrust and pushed back in rhythm so that it was pretty powerful when my hips banged into her ass. I realized there was no way I could pull out and came inside her.

We lay together on the bed side by side and she put my hand on her pussy and told me to just hold it there and feel our warm sex. We stayed like this in silence for a while until I told her I was worried about getting her pregnant. She told me she was on the pill, which I did not even know was a thing.She then sprang up from the bed and told me to come back tomorrow to finish moving the furniture. And she allayed my fears by reminding me not to tell any of my friends or else we’d both get in deep trouble. The next day and another 10 or so days over the course of a month I went back and she paid me to fuck her. Watch for part 2.

NSFW: yes

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