The older woman and me at nude beach Sex Stories 2024 – Y2 Stories

She was widowed, 68 at the nude beach. It was crowded, she made room for me. She let me lose my virginity in her old hairy pussy

I was 16, in college early and went to the nude beach one afternoon. It was so crowded, I was in my swimming trunks but already had a hard cock from looking at all the tits and pussy. I’d honestly only seen my mom naked before. From about age 11 she would change everyday after work in front of me, then at night again to get into her nightgown. This wasn’t my mom though, girls and women of all ages, body shapes, tit shapes and sizes, shaved pussies, trimmed pussies, hairy ones. Some were blonde on top and dark brown on their pussy, others blonde or redhead all over. However; I walked halfway up the beach and couldn’t find a place to lay my towel. On my way back I moved up further from the water to see different pussies, and and older woman told me I could put out my stuff next to hers. She moved a cooler over and I thanked her. I laid down and she commented that I still hadn’t taken off my swimsuit. I leaned over on my side and mentioned that she only had her one piece pulled down below her breasts. They were really nice looking too, I figured a C cup, they were a D, and she had reddish brown nipples about half dollar size area around her nipples. She said that she didn’t like to go all the way as she hadn’t shaved or trimmed like most of the girls do these days. I mentioned that my mom didn’t do any of that either and it looked ok. So she dared me, she’d take hers the rest of the way off if I did. Mentioning my mom made my cock go soft, so I stood up, she stood up and we stripped. Laying back down she was on her back sort of propping herself up in a half sitting position. She commented to me after about 15 minutes that unless I had some sunscreen I’d better turn over. I blushed and said I really shouldn’t. She told me that it was OK, half the guys there got hard several times. Besides, she had some lotion and asked to rub it on me. I let her, and she rubbed all over, and now I definitely couldn’t roll over. She just poo poohed that and made me roll over. She rubbed on me, and then even rubbed some on my cock with her hands wrapped around it. I jolted up. “Don’t worry, you have to protect this too” I whispered that i was hard, and she said it was nice knowing and old granny like her could get a young guy like me hard.

I rubbed lotion on her, first her back, then hesitantly on her butt, “get in my crack” she said and I did. Then rolling over she was looking into my eyes as I rubbed her shoulders, her upper chest, and she said to be sure to get her boobs, but under her boobs too. After that she pushed my hand down to her belly and her pussy. “Even though there is hair it needs it too”. She was moaning under her breath and told me how good it felt, her pussy was getting wet. “I’ll bet your girlfriend would be mad at your for doing this, especially to an old hag like me”. She got the response she wanted about the old hag, and I told her I’d never had a girlfriend. I told her how old I was and that I was a 3rd year in college and because I’m so young and in classes with 20 to 22 year olds all day, everyday I wasn’t likely to find a girl.

Soon she talked me into walking up to her apartment which was at the end of the nude beach and overlooked the ocean and all the naked people. Upon entering she told me she had a rule. Unless her family was over, which rarely occurred, anyone coming in had to be nude. So we both stripped off and as she fixed lunch I watched her. She was 68 I’d found out, widowed, still had natural brown hair on her head and on her pussy, she had incredible looking legs, and a really taught butt. Her tits were big but were really full, sagging some but still made a nice pictures. Her face was very pretty, I’m sure in her youth she was beautiful. She was beautiful when I was on top of her in her bed, fucking her. She’d already given me my first BJ, now my first fuck. I went to see her several times a week. Naked upon entry. We were fucking and fucking, I learned how to eat her pussy, lick on her ass hole, and eventually fucked her ass too.

After about three weeks, I used my own key and opened the apartment door. There was my old woman Delilah, naked with a friend. It was an other woman, slightly older, gray hair even on her pussy, though her pussy hair was pretty sparse. D told me to strip, I knew the rules. Her friend O, commented that I was a pretty boy and look like I had a nice cock. D said “It is nice, I’ve told you how good he’s gotten”. Then to me. “you know O hasn’t had her pussy eaten in over 20 years, why don’t you show her all I’ve taught you?” I didn’t think it was much of a request so I got down, naked in front of O as she spread her legs. It took a while to get her wet, D explained that as women grow older it takes more to get them wet and excited. But O did get wet, and my tongue on her clit brought her off. I thought after two times it would be enough, but she just held my head to her gray haired pussy and I kept going. After four times cumming she stopped. D hauled me up next to her and kissed me. “Hmmm all that pussy juice on you, you are ready aren’t you?” my hard cock in her hand. She started to go down on me. O stopped her and said she had something special. For me to close my eyes. It felt unlike anything before, it was definitely a BJ but it was so different, really good but different. I opened my eyes and she had taken out her false teeth and was gumming up and down on my cock. As soon as I saw what it was, I came in her old mouth. She swallowed, most some slipped out of her mouth onto my leg, she scooped it up and ate it too. She looked at D and then at me and said how good I tasted, she’d not had that in such a long time. She put in her teeth, sat on my lap and kissed me. Then she got dressed and left. D told me how much she appreciated me doing all that for her friend. Two days later, D gave me an envelope from O. It had $300 in it. I wanted to return it but she said no that I should take it. Just tell her how much it meant to me. I did that, even ate O again, this time fingering her pussy too. The next day D told me that O would like me to go over to her apartment, just down the hall from hers, and fuck her. She wanted sex, and she wanted to pay me to give it to her. I really didn’t want to take money, I’d come to like O as a person. D told me she was very wealthy and it’s something she wanted to do, she had no family.

It was agreed between them that I would walk down the hall naked and knock on O’s door. She opened it and was also naked. I made love to her, not just fucked her, I kissed, nursed on her sagging almost empty tits, licked my way down to her pussy, and I slipped into her once she was ready. I fucked her for about 20 minutes, she came but stopped me. “Am I hurting you? I can stop if you want” I said. “No baby, no, I wonder if you’d do something special for me, something my husband used to do for me?” she answered. “Sure anything you want”.

“Stick it in my butt and make love to me back there, will you?”

Now I love anal better than anything, and an old, tight ass that hasn’t seen a cock in over 20 years? I’m onboard. I lubed her ass up with her pussy juice, and slipped in. I didn’t just buttfuck her, I did what she said I made love to her in her ass. She started bucking and heaving, moving up and down pulling my head to her mouth, to her tits, begging me to keep going. I honestly could only go about 10 more minutes, I’d never had D like getting buttfucked, she let me do it but didn’t cum. O loved it. I shot off deep up her backside and just collapsed on top of her. She got out from under me and came back from the bathroom, “Roll over baby” she said. She had a warm washcloth and wiped my cock and balls off, then wiped her pussy and her ass. She took it back in and came back and got in bed with me again. In about 20 minutes it was a repeat and I shot another load up her backside again. Again washing me up, I got dressed and she still naked, gave me an envelope. I walked back down the hall to D’s place and there in the envelope there was $ 1000.

So D got a bright idea. She was retired, and on limited income. However; she knew lots of rich women, a lot old like O, some young in their 30s but were quite fat or unattractive or both. I was soon servicing her friends, and she and I split the money. I was still spending a lot of time inside D’s various holes too. By 6 months I’d fucked over 20 women, fat, old, ugly, fat-old-and ugly but didn’t care, I’d gotten lots of pussy, mouth, eaten pussy, and even fucked a few in their asses, especially the fat ones. One day I’d been with D for the weekend and on sunday I buttfucked her on her balcony, she came in and told me it needed to go both ways. Not knowing what she was meaning, she came out of her room wearing a strapon dildo. “I’m going to fuck you in the ass too” she stated. Bending over her lap she lubed me and started with just one thin finger, moving to two then three. I was stretched enough for the thin, short strapon. She said she had more and bigger but later. By two weeks I’d get fucked everyday by her strapon. I was now taking on the 9 inch long modestly thick one.

I came in a week after taking the biggest one several times, and found her on the couch with a guy behind her. He was fucking her asshole from behind, and she told me just to sit and watch. The guy finished quickly and pulled out the thickest cock I’d ever seen. I didn’t realize she was fucking other guys, and she said she wasn’t but that was her landlord who was saying everyones rent was going up and this put it off for a month. I asked about how big he was and how she could take that big, she said it hurt as she’d not been stretched out like she did to me. He was married, pretty wealthy he owned the building and his wife wouldn’t blow him or let him touch her ass with his cock.

The day came, and I was being left alone in the apartment for the landlord. He came in, I was in light makeup, panties, thigh highs, and a camisole, it was what he requested. He wanted to get a virgin ass and mouth, even if it was from a guy. I was shy, he liked it. He had me get on my hands and knees next to the open balcony door. He wanted the spying neighbor with the spyglass across from us to see, and the neighbors to hear what he was doing to me. He asked me if I was a virgin and I told him to gay sex yes. He made me suck him off so he would last longer. He came a ton. After some waiting time playing with my ass, he lubed me, made me lube his big cock, and he slowly but steadily pushed it into me. It was bigger than the dildo but D told me to whine and wince so he’d think it was hurting me. To tell the truth it did hurt. I knew he wanted it, so I was loudly grunting and talking. “aaggh that big thing hurts baby, please take it easy, oh god remember I’ve never done this before you’re hurting me” things like that. He shot off and strangely I wondered if women felt this in their ass or in their pussy, I felt every shot of his hot cum shooting into me. He was a big cummer too. I couldn’t hold it all in, as stretched out as i was my ass was gaping, he took a picture. I stood up and it leaked out and down my thighs as I saw the guy across the way looking in his telescope at me. I turned and bent over letting him see the gape in my formerly virgin asshole. I went and shit it all out of me, what hadn’t already come out. Then it was round two. This time bent over the back of the chair so mister telescope could see it all. I put my panties back on, and he told me to tell D that he was good, that would keep her for 6 more months.

I spent three years getting paid to fuck, and eventually even fucking with and getting fucked by some couples. I and D had sex together with the landlord every 6 months after 3 years he signed a waiver for her lower rent for life. I got one of the ugly women pregnant at her request even. In my personal life I had lots of girls, all satisfied with what the older woman taught me. She was at my wedding to the girl I knocked up.

I couldn’t ask for a better teacher, or a better past sexual history. My wife thinks she was a slut by having 5 cocks before me.