Straight Male / 21

Boss' Ol Lady

I work construction, building houses. Have done it since I was 17, and I managed to get in tight with my boss. He's an older biker time guy, and he lives around 10 hours from here with his wife. Every other weekend I'd drive him home (too many dui's to drive himself) so he could see his kids and all.

I'd been driving him every other weekend for around a year, and it was awesome. Had alot of fun, made a bunch of new friends, and even found a chick that I could see while I was up there.

One night my girl had brought me back to the bosses house, and I let his wife know that I scored some good weed. She comes outside and sits across the table from me, but opposite from my girl. We pack a bowl and begin to pass it around.

My girl was telling her about our day when my bosses wife (much younger than him, only 3 years older than me) turned and spread her legs. I noticed immediately, but averted my eyes. She wasn't wearing panties, and her gown wasn't covering anything. As we smoked, she passed it to me and when I was taking my toke, she saw me looking and pulled her gown out of the way for me to see better.

I passed the pipe to my girl while feeling my dick stiffen up in my jeans. Trying not to get caught staring, I tried my best to not make it obvious, but every time I would look away, she would do something to draw my attention. Rub her clit a little, spread her lips, slide a finger in.

While my boss's wife was hitting the bowl, my girl reaches over into my lap and feels my hard dick. She turns to me and looks me right in the eyes and leans in like she was going to kiss me, and sees my bosses ol lady shut her legs. She acted like she didn't notice, and kissed me. When she sat back in her chair, my boss' wife opened back up.

My girl just smiled after watching my eyes pointing in that direction. Without saying a word, she reaches over and bumps my leg. Gestured towards my bosses wife sitting on the other side of the table and back to her crotch. I nodded slightly.

She scoots her chair closer and leans in to undo my belt. I watched my boss' wife watching as she reached into my jeans and pulled my dick out, and started to finger herself while watching my girl stroke it. That went on for a few minutes until my boss' wife asked us to move from right outside of the front door of their rural home, and guided us around through the garage to a set of stairs that went up to a bonus room above.

My girl whispers when we got up there to her, "you like watching me jerk his cock?" She answers "fuck yea." My girl pulls my cock out again and pulls my pants and underwear down to my ankles. She sits me down in the middle of the couch and asks if she would like to see her put it in her mouth, to which my boss's wife eagerly nodded. I watched her sit on her feet beside me on the couch and spread her knees, then took my hand and began rubbing her pussy with it. It didn't take long before I took charge an began exploring.

My girl gave room when she asked if she could suck me for a minute and took her clothes off too, and put her pussy close enough for me to use my free hand on her.

The boss's wife even helped rub her clit while I fucked her with my fingers. Next thing I know, she was guiding my girl to straddle me and putting my dick inside my girls pussy.

After a good 10 minutes, she had came a few times and asked if I wanted to feel my boss's wife's pussy around my dick, and when I said yeah, she got up and swapped places. Not going to lie, my girl had some good pussy, but my boss's wife felt so much better. Maybe it was tighter, maybe it was just the situation, but after a couple minutes of her riding me, I was ready to pop! I told her I was ready to cum, and instead of getting off, she rode me harder until I filled her pussy with my cum.

My girl watched my cum running down my shaft as she rolled off and laid back on the couch opposite of my girl, with my cum was oozing out of her pussy. "You're gonna make a mess, let me help you with that" my girl said as she leaned across me to lick her pussy clean. It wasn't long before I was ready to go again and left one in my girl too, but my boss's wife wasn't there to finish her with me. That was the first of many experiences with his wife. Some together, some on my own. Always risky, always amazing, and never got caught... thank the gods!

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# 65411 - by Company man / May 6, 2023

- True Sex Confessions -

Straight Male / 45

Wife On Camera

I like to fuck my wife on camera. She's 27. The other day we fucked in front of a guy who was wanking the whole time. I sent him some pictures of my wife and he came on them and sent them back. The wife has no idea.

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# 63918 - by Foreigner887 / February 14, 2023

- True Sex Confessions -

Straight Male / 42

Wife Shocked Me, Big Time,

My wife and I were married at age 20, we had dated about 8 months before tying the knot. I took her virginity about 2 weeks before we were married, since she had been on the pill a month or two.

Like most newlyweds the first few months we tried sex in every way imaginable. One night she was lying on her stomach, My head was down around her waist and I had two fingers in her pussy slowly sliding them in and out. I had her butt cheeks spread slightly and I pushed my thumb against her asshole, just pressing slightly. She twitched and giggled and I did it several times.

I put my thumb in my mouth and got it wet. I slipped two fingers back in her pussy and pushed my thumb in her ass about an inch. When I pulled my thumb out, she told me to do it more she liked it.

I lubed up my cock and laid down on top of her and slowly started pushing my cock in just enough to have the head inside her. I asked her if she was ok and if it hurt. She told me no, just keep going. I had never done anal before and I was really turned on. I kept pushing it in deeper and she was moaning and twitching. I was in deep and kept slowly pumping my cock in and out of her ass as she rubbed her clit.

I blew my load in her tight ass as she shook and orgasmed really hard. I went to roll off, but she said just lay still and leave it in. After about a minute or so of heavy breathing ,she started fingering her clit and got herself off again moaning and gasping.

After that anal sex became a regular part of our love making. After a few times I asked her why it was so easy for her. To my shock, she confessed that her older brother had been fucking her ass since she was 16.

I was confused about the whole thing. Should I have been pissed that her brother was fucking her ass or should I have been grateful to him because the backdoor was now always open and she loved it as much as I did.

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# 63919 - by Duz it Matter. / February 14, 2023

- When I Was A Kid -

Straight Male / 51

New Friend

I was 15 years old when a boy, his mother and sister moved into our neighborhood. There weren't many houses and kids in our neighborhood so it was good to have a new friend. When I got invited over to his house to use their pool it was interesting. I was introduced to his mother and sister and didn't know what to think. They were both naked. We went to his room to get undressed and when I pulled out my swimsuit he said we don't use those here. It was my first time swimming naked with others. I was nervous at first and then became more relaxed. The mother and sister walked around like it was no big deal. This was better than the porn magazines I had.

I went over regularly until they moved away which was only for a few months. It was a few months after they left when I heard my mother talking with another neighbor. They brought up that they were nudists and how disgusting it was. They were talking about how exposing yourself to others was perverted and anyone who did that should be arrested. The neighbor went on to say any mother who lets herself and children be seen by others naked should have the book thrown at her. My mother said she would never let her son do that and if I did I would get one hell of a whooping.

I guess she didn't know I had been over at their house naked many times with all of us seeing each other naked. I just kept to all to myself and never told her.

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# 62807 - by Kid / December 24, 2022

- It Was Disgusting -

Straight Female / 46

Spring Break Experience You Don't Want To Have

This really happened to me. It was 1997 in Mexico for Spring Break. We met some guys and went to a party. I got stripped and taken outside and put in a van in a dog kennel and to some other place. A high pressure hose was used up my behind and vagina to 'clean' me out. Men, of various ages, came buy and wrote down their best offer and put it in a bowl. I couldn't raise my head and my hands and knees were digging into the wire in the kennel.

The bowl was taken inside and a man came out and said he had won the auction and I was his. A collar and chain was put on me and I was let out like that and I was taken, by the chain and the collar around my neck, back into a room where nothing was sacred. After he had his fun, he tied my chain to the leg of the bed and left me there still naked on the floor. A girl came in to check on me and I guess to see if I was still alive. She grabbed the chain and took me to a bathroom to shit and pee before walking me outside where I was pressure washed again and put back in the dog kennel for the next group of men to come and write down their offer.

I was auctioned off three times that night.

I was left naked on the side of the road before sunrise. I was lucky, the person said who picked me up, that I was left like that, usually girls are found dead.

That's my story about Spring Break. My friends looked for me and didn't find me and they were told that I had gone with a guy, so they went back to the hotel.

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# 62632 - by Can't say / December 14, 2022

- I Did It For The Money -

Straight Male / 27

I Do Old Women For The Money

For about 2 years now I have sex with old ladies for money. I moved to Florida for a new job and it was going well. I made decent money, but not so much that I could afford that new Corvette I wanted. Well one night after work I was having drinks with colleagues and a senior partner was talking to me asking me a lot of personal questions, was I involved with anyone, was I straight, and so on. We had already had enough to drink to not be able to legally drive when she said what would change my life forever. Would you fuck an old broad like me for money? It totally took me by surprise but I just blurted out hell yeah. What I didn't realize was how much she was willing to pay. We got a Uber and went to her place. A mansion by my standards, very nice indeed. We went straight to her bedroom and she started unbuttoning my shirt and I did hers and we ended up naked in minutes. She's not a bad looking woman even at her age, near 60. Tall thin, small tits, shaved pussy. I hadn't had sex in a while and was very horny. But I took my time and seduced her. Kissing her passionately then the back of her neck then her nipples which responded nicely, I kissed my way down to her pussy and ate her to quite a few orgasms. She has a nice pussy. It tasted and smelled great. I'd never had sex with anyone near her age so I didn't really know what to expect. I then fucked her brains out for at least 45 minutes before busting a huge load in her old pussy. We laid in her bed after for a bit kissing laughing and talking. I went back down and ate her old snatch again licking my cum out of her then fucked her again, and after a few minutes she said fuck my ass stud. She had lube in her nightstand grabbed it, and slathered it on her ass and my raging hardon. I plowed her ass like my life depended on it and she fucking went wild. Fuck my ass you young buck. Yes fuck this old bitch! I did as I was told and eventually unloaded in her ass. We fell asleep after and woke later in the morning. We showered and I ate her out again then fucked her one more time. She gave me $1500 bucks for the best fuck she had in years. We had breakfast and she told me that she had lots of friends who would pay me even more for the same treatment. Fast forward to today... I've been fucking her and 12 of her friends regularly. I paid cash for that Vette a year ago. And have over $50K in the bank. Yeah most of them aren't nearly as hot as Miss K. But they pay well. There is one who is really fat and gross to be honest. But she pays me just to suck my dick and then once in a while I'll put it in her pussy and fuck her for 10 minutes and she's extatic. She pays me $1000 if she just blows me and double if I fuck her. It's gross for sure but for just a few minutes a couple times a month I make good money. I still work but it's remote and I've actually fucked many of them while on the clock.

I do fuck Miss K a lot. And for free now. I love fucking her actually, she's the best piece of ass I ever had. I absolutely love fucking that ass and she goes crazy when I do. I also love eating her pussy and do it every time we get together. She did buy me a condo on the beach. But she has a key and the only stipulation is that it is our place. No one else gets fucked there. I'm good with that. She really treats me great. And my real confession is that I love her. We do spend a lot of time together. We go to expensive restaurants all the time and go on cruises and such. We hold hands and kiss in public as if we were just another couple.

I'll probably fuck these old ladies until they want me to stop. But I'm investing all this money and getting my broker's license soon and won't have to work after age 30 and I'll be very well off. How lucky can one guy get? If Miss K asked me to stop fucking all of her friends I would though. I don't think it'll happen because she loves hearing about their experiences with me from them. And I do her for free! She calls me her boy toy but one time when she had a few drinks too many she said she couldn't think of her life without me in it. I feel the same Miss K. I love you.

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# 62356 - by Deuce / December 2, 2022

- I Did It For The Money -

Bi-Sexual Male / 32

Needed A Phone

So it wasn't really for money but I broke my phone and don't have insurance on it to replace it. A older buddy of mine had an old phone he offered to sell or trade, I didn't say yes instantly and waited almost two weeks before my phone fully stopped working and he knows my past so instead of cash he just wanted to make the first video on it, and now I have a phone again.

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# 62571 - by Doitifitfeelsgood / December 12, 2022

- Evil Thoughts and Deeds -

Straight Female / 52

If My Hubby Only Knew

The hubby has really been on this kick for me to become a hotwife. When I quizzed him if he thought that he could eat me after I had someone unload inside of me, he said that he wasn’t sure but most likely not.

So here is my confession. My husband and I started dating in High School when he was a senior and I was a junior. Anyway on my senior trip I spent most of days and all of my nights with a classmate. First it was very exciting to cheat, also knowing that we wouldn’t be doing this again, that lead to the sex being extremely erotic. Every time we had sex, I had at least one orgasm, most of the time 2 or more. Being young and naïve, we didn’t use a condom and he finished in me every time. I did him twice on the bus ride home, we finished about half an hour before arriving, spent that time making out, treasuring every stolen moment.

My husband, then boyfriend was waiting as he was my ride home, we talked about the trip, I became exceedingly horny and snuggled up to him and asked if we could go parking before he dropped me off. His car was a real fuck wagon, so we pulled off and crawled in the back, lifted my skirt, pulled my panties off and went to town eating me, I came. He certainly seemed to enjoy how I tasted. Then he fucked me and it was the first time that I’d had an orgasm during sex with him, and it certainly was a mindblower too.

That was a long time ago but I have masturbated many times to that memory.

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# 62690 - by Bonnie / December 17, 2022

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