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Derwood_lolly

Derwood_lolly Avatar
Gender: Straight Male
Age: 40
Relationship Status : With someone
Profile Visits : 331
Number of Comments : 55
Number of Confessions : 0

Derwood_lolly's Favorite Confessions:

- True Sex Confessions -
Straight Female / 45

Recurring Dream

I've been fantasizing about younger guys. Not just a couple of years but like 20 years younger. There's this coworker Bill he's 22 great guy and just graduated college. One night before leaving work. He laid me on top of his desk pushed up my skirt. Then seeing I had not been wearing any underwear. He slid down and licked me until I moaned fuck me. I heard him unbuttoned his belt and unzipped his pants. I then looked down to view his stiff cock. I smiled and said fuck me. I then felt him penetrating my wet willing body. I pushed back on his cock like I just gotten married. After he released, he moaned can I fuck mommy again. I shook my head yes. He ended up fucking me twice. Afterwards I returned the favor and sucked his dick and licked it clean. I knew he was about there, and he held my head in place. And dumped his load in my willing throat. After getting home Sam my husband 47 asked how was your day dear. I reply fantastic.

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# 79659 - by Jenny / June 11, 2025
- Funny As Fuck -
Straight Male / 28

She Was Beat Red

I am hooking up with this married little hottie for the gym. She’s in her late thirties had a killer body very petite has a nice set of tits and a plush little ass. Very soft squeezable for sure. I’d been hitting on her for a while and she must have had some issues at home because she took up on offer to meet up after the gym. We did this for a while before getting really intimate. Once we crossed that line she was open for business. We truly care for each other I could tell she was sincere i have this older suv that the top can be removed. It’s all updated really nice tinted windows the back seat lays back and her and I spend a good amount of time back there. Since it’s private because of the tinted windows. I absolutely love giving it to her form behind. Most of the time she just pulls her legging down below her ass and gives me access to her. Her ass makes a little heads when I’m smashing have tons of pics and videos. She gets into it we usually find a quiet parking lot or garage. We have a marina close by that can get busy at time but at the end of the parking lot is a yacht club so it’s private and I can rail her she can get a little loud and we have a good time. I had been out with friends and some ass broke my window and got in and ripped my stereo and some other stuff. I got it replaced as well as the window. Problem was the rear window was replaced and it came with out the tint. I met up with Yvette at the gym she was being super knotty that day and we ended our work out early. She hopped in my truck and I drove over got the yacht club. There was an event going on so lots of cars so I parked closer to this restaurant that’s between our gym and the yacht club. Some people walking but it was loud because of the even lots of people but it didn’t bother us. I was horny she was horny we made out she sucked on me she got on all 4s pulled her leggings down exposing her tight Litte ass. I licked and licked and she had her head down I pulled my cock out and started to push it in she still has her head down and started to slam back into me. It felt amazing and I looked up and saw 2 guys and a women just sitting down and watching us. Then realized that the rear window was not tinted. It was hot to have some people watch us. They laughed the 2 guys gave me the thumbs up. I picked up the pace and Yvette started to cream herself I grabbed her by the hair and pulled it up. Loudest she could she told me she was cumming and to keep fucking her. She then looked directly into the eyes of the 3 people watching us. She tried to wiggle away but i picked up a harder pace and she went with to. We fucked for another 10 minutes until I shot my load inside her. At one pint I lifted her up and showed them her tits. We checked the event after and the 2 guys complimented me and Yvette on her performance. She was so embarrassed she made me take her back to her car. I got more head there and we fucked one more time. I got the window tinted short after that. Still hammering away and occasionally we roll the window down and let a few people watch.

2
# 79666 - by Anonymous / June 11, 2025
- Fetishes and Kinky Sex -
Bi-Sexual Male / 28

The Experiment

My wife Julie and I are a slim, fit,attractive couple in our late 20's.Julie was a party girl before we married having various sexual adventures with both men and women then toned it down when we got serious. Our sex life was pretty hot up until about a year ago. We both had gotten a little bored and basically had sex once or twice a week without much passion. Julie and I had a long talk and she said she loved me just as much and I felt the same. There was just no real excitement.

Julie and I discussed swinging with other couples and her eyes lit up. " I have a better idea " she said. "Something kinkier" she added. I listened as she proposed another scenario. She mentioned there was a lonely guy in her office. His name was Chuck and he was a balding overweight guy around 40 who had not dated in years and was definitely in the plain looking category.He hung on my wife's every word and appeared enthralled by her. Julie continued" What if we have a little sexual experiment with him one weekend". "He is desperate and needy for any kind of attention. Imagine how excited he would be to have sex with me". I thought she had either lost her marbles or she was not serious and pulling my leg. Either way I called her bluff." OK sure invite him over". She smiled and went to watch some TV.

Late the next week she came home from work and said" It is all set. Chuck is coming over Saturday night". I nodded still thinking this ain't happening.

Saturday evening arrived and Julie got some wine out after we had dinner. She changed into a see through negligee and asked me to match her by wearing some thong underwear. I thought oh my this is silly and put a black pair on.

The doorbell rang and Chuck did arrive. He looked nervous and had another bottle of wine with him. I had seen him once before when I picked my wife up from work so knew what he looked like. He was homelier and pudgier than I remembered. I thought she cannot be thinking of going through with this. My wife invited him in and she got the wine ready. He was wearing grey slacks and a big blue sweater. We went to the living room and Chuck stared at both of us.

After several glasses of wine my wife led us to the bedroom. She lay back on the bed after taking off her negligee and asked Chuck to join her. I looked on as she had him undress and reveal his heavyset body. Even his chest had man boobs. He fumblingly reached to caress one of her breasts and she pulled him close. She gave him a little kiss which excited him. He reacted by giving her some sloppy wet smooches.Julie told him slow down we have lots of time. "Here let me show you how to kiss properly" she said. She kissed his mouth softly and you could see him start to match her technique. They kissed a little deeper and deeper until it looked kinda passionate. My wife then urged him to go down on her. He eagerly got between her wide spead apart legs. He kissed and licked her pussy hungrily. Julie started moaning. I did not expect this. "Tongue me Chuck make me come" she urged him on. He kept doing it as her legs quivered and shook. She cried out as she had her orgasm. It was a bigger one than I had seen her have for years. Her body shook wildly then it was done. My cock was rigid seeing this happen. My wife had a demure expression on her face one I don't think I have ever seen before. " Get on top of me Chuck". " I want to feel you in me ". Chuck got on top of my wife. His short fat cock slid into her wetness easy. She clung to his heavy body and they kissed as he thrust frantically inside her. He came quick and surprisingly she had another orgasm to match him. He was done and slowly pulled out. My wife smiled at him and said she loved how he made love to her. He grinned and lay back. Julie motioned to me to lay on the bed. I did and she took my thong off revealing my erection." Chuck baby can you take care of my husband with your mouth like you did me?". I looked at my wife puzzled. Before I could say anything Chuck's mouth covered my mouth. He gave me a deep wet kiss.I tasted my wife's juices in his mouth.My cock stiffened even more. I was shocked I enjoyed his kiss." Kiss him back darling" she told me. I kissed him and discovered his kissing excited me more than my wife's did. He went down my body and his mouth kissed my cock. I groaned as he took me all in. It was sexier than when my wife sucked me.... deeper more intense more needy. I blasted my load down his throat and he took it all.

I fell asleep after my orgasm. I woke up in the middle of the night to see Chuck and my wife moving in rhythm. They were fucking again in the missionary position and kissing like we once did. Chuck let go eventually and gave my wife another load.

That night changed the three of us. Chuck comes over all the time now. He has sex with my wife and then with me.

6
# 79672 - by Enamored / June 11, 2025
- Anything Goes -
Straight Female / 31

Ex Coworker

When I was 22 I was working 3rd shift at a store. One of my coworkers was this hot single dad in his late 40s.

One night on break I gave him a bj in his suv. I was so surprised to see a big uncut dick in his pants. Never would I had thought he was hung or uncut. I swallowed his cum and he went back into work.

A few nights later he said I can come to his place after work since his kids weren’t there. So I went to his place.

The sex was great. Loved sucking him and taking him in my pussy was a challenge at first because of his size. I was young and very tight.

Then the unthinkable happened. He asked to fuck my ass. I had only tried anal once and it wasn’t that good I thought. But I let him.

Half a bottle of lube later he was in my butt. I was stretched to the max. My tight little ass had his big dick almost balls deep.

I was laying on my stomach moaning as he fucked my ass. I was surprised I could take it so well.

He cummed pretty quick because I was so tight. As he pulled out I could tell my hole was stretched wide open. And he confirmed it was when he told me I was gaping wide open. He said my young small tight ass was really nice.

He wiped my hole clean with a towel and we fell asleep pretty quick.

When we both woke up I rode his dick until he cummed in my pussy.

I went to work that night wearing the same jeans and thong that I wore the night before but borrowed one of his shirts.

It was our secret we were hooking up the whole time we worked there. For a little over a year I was sucking his dick every day we worked and he was fucking but butt a few times a week. He really loved anal sex saying his ex would rarely do it.

2
# 79664 - by Abby / June 11, 2025
- Anything Goes -
Straight Male / 23

He Wants To Join In, I Think.

My newish neighbours across the street Alice and John are both in their mid forties. John drives buses for a living which means he works different shifts.
And for the past eight months I've been fucking his wife pretty much every single day.
Alice is an average looking woman, however she is by far the dirtiest slut I've had sex with.
She is constantly horny which suits me as I have a very high sex drive, especially when the woman is prepared to do almost anything sexual.
We began fucking the very first time we met outside our local shops. It was clear she was interested in me sexually as we spoke, and like she was asking me about the weather Alice wanted to know if a young guy like me had sexual stamina.
I told her there was only one way to find out and fifteen minutes later in her kitchen i was fucking her from behind as she leaned over their kitchen table.
Since then I've fucked her mouth pussy and arsehole most days.
Yesterday we drove over to bluebell woods where I fucked her as another man watched and wanked nearby and she couldn't have cared less.
Also yesterday, and I genuinely didn't know this, is her husband John knows and accepts his wife is being fucked by me. In fact he's asked Alice if I would let him watch
Now I know some married men are into this, but I'm not into guys sexually at all. So is John just wanting to watch me fuck Alice, or do you think he wants to take part and interact with me.
I don't want to stop fucking his wife, but I'm not sure id want him involved so I can continue fucking her.

5
# 79665 - by Addy / June 11, 2025
- Obsessions -
Straight Female / 18

What I Like

I know it sounds ultra-lame probably, but I love going online and watching videos of guys ejaculating. I don’t care if it’s jerking off, gay, pulling out, facials, that thing where they jerk off on a pic of someone (tribute I think it’s called), I just love hearing them moan right before they start shooting their creamy goodness on everything. The more they cum the more it excites me. I don’t typically like watching the stuff leading up to the ejaculation, just the ejaculation itself.

5
# 79667 - by Allie / June 11, 2025
- My Spouse -
Straight Male / 42

Circled Back Around

When I was right out of high school I had a part time job working at a liquor store gas station. It was a small town always the same people that came in. There was 4 of us that worked there the boss Todd his sister myself and this girl named Carrie. Todd and his sister were kind of strange but they let us get away with just about anything as long as the work got done. I’m pretty sure his sister wanted me but it was strange because Todd and her looked a lot alike. Carrie on the other hand was a cute blond thick girl. You could call her a bit chubby she was soft around the midsection she had nice tits some thick thighs big ass. She seems to always be in jeans. She was not ugly and she wasn’t a super model but was a closet freak. We often worked together and when ever we had any alone time we would fuck. She would give me head and I’d eat her out. A few times he would sit under the counter and suck me off. She gave really good head and i benefited from it. We worked together for a while and I left we kept in touch but after a while we broke ties. I went on left after 2 years of community college and transferred to a 4 year college. I came back went to work for family stayed in the family business. When it was time inside the opportunity to buy my other family members out of the business. Not one of my brothers and sisters wanted anything to do with it until after they had sold there share and I was doing very well. That’s a different story I'll tell later. I never married dated a lot no kids work kept me busy. I have a good life enjoy my hard work nice house cars etc…. I don’t date at work and encourage my workers to do the same. Just lots of drama that can damage profits. I was in need of an assistant I had hired a few girls and they had not worked out so I went with a temp agency and asked for a girl with good qualifications.

It was Wednesday my HR manager came in and introduced me this women named Carrie Blahah I was not paying attention at first and my HR lady who is a close friend said hey look up so I did and there still Carrie the girl form the old liquor gas station. To be honest she looked the exact same she didn’t remember me at first until she took a second look and she asked me if I remembered her I felt juts like the last time I had seen her and said yes I remember you. We chatted for a bit my HR lady looked at me funny and off they went. She was just the first couple of days she still had that cute look same body didn’t have caring on first thing I noticed. After a week we chatted some more and more found out she was divorced guy was a real POS. She was still the happy go lucky type. One day after work she left and after about an hour came back and brought her and I a 6 pack which i thought was cute. We each had one and I put the other 4 in my office fridge. Before we knew what was happening she was on her knees and my pants where around my ankles. She was still so damn good at giving head. Never gagged cleaned up afterwards ate all she could then it was my turn i retired the favor that night we left around 7 and ended up at my place. I had to let my HR lady know what was happening and she herself said that it was my rule. I had to let her go after 4 months. Yup I fired her and she could not believe it. She was ok with it because she was already living with me by then and a year later we married. My now wife always tells the story of how I fired her so I could marry her. She always leaves out the fact they she absolutely gives the best head I have ever had. She still comes by and does that for me. If there something she really wants or wants me and her to do she will ask me while she has my cock down her throat and she knows I won’t say no lol. I wonder if there are more people that have a similar experience or met there significant other like this or similar situation.

0
# 79668 - by Carrie / June 11, 2025
- My Spouse -
Straight Male / 43

I Got Past It But A Benefit From It Makes Me Want To Leave Her

My wife dated a guy she went to high school with until she was 23. He was crazy into his church and my wife told me they never had any sexual activity.
I met her doing work at her parents house, my sexual experience was the complete opposite of hers. I fucked every girl I dated in high school and college.
When my future wife finally decided that she wanted to have sex it was over the top to her. She was tore up about losing her virginity.
Flash forward 15 years, she was steady and rarely tuned down my requests for sex, but, it was very vanilla. I licked her asshole once and she told me to just stop, she didn’t want to have sex after I did that. Turns out she felt like she missed out. I never had my cock in her ass.
So I caught her cheating on me, turns out she gave into a threesome with a couple “friend” of ours she let the wife lick her as my wife sucked the guys cock. She admitted she met them over 20 times for sex and even fucked the guy in our home.
This just made her want more, she thought she would experiment with them and then settle back into our life together. Instead she just went wild. Meeting many guys over a two year timeframe. I caught her because the wife of one of the guys my wife was fucking came to my work and in my office told me my wife was having an affair with her husband. I confronted my wife and she broke down crying. Turned out she was addicted to new cock. She loved ass fucking yet she never let me know the back was open, knowing I would put it together.
So we went to counseling, after some time past my wife asked if I wanted to “enjoy” her new skills? She even offered a threesome to “even it up some”. I declined.
Ass fucking her was almost an every time thing. She squirted and came like crazy. Especially if she leaned back and rode my cock as she toyed her pussy. For once she looked at my face and I guess I was emotionless. You know don’t you she asked me. I just said yes not knowing what the fuck she was talking about. Crying she said it just happened and then she couldn’t quit. Fucking DP, my whore of a wife hooked up regularly with groups of men.
I’m 4 years past her cheating and I’m just done with this shitt.

4
# 79653 - by Andy / June 10, 2025
- Anything Goes -
Straight Male / 28

Should He Be Mad

My friends Sammy and Anita and I have been friends for a while. I met Sammy while working at a warehouse job we got along had similar interests and became close friends. With that his wife Anita also became close with me. She is a rather thick Puerto Rican woman very pretty large ass large hills thick thighs small boobs. Do I check her out yes and until recently I would never cross that line. When was that line crossed about a year ago. When after a night out we ended up leaving my date and me coming back home with them. Sammy had always talked about swinging or bringing another girl into there life to try it out. Apparently after some drinks everything came out. They had intact brought girl in a few times Sammy showed me pic’s and videos of Anita and this girl going at it and finally fucking. I called him lucky and he waited and then said that Anita wanted 2 guys now. I told him I’m not touching you like they touched each other. He laughed and aid no she wants 2 guys its only fair. Didn’t take much convincing she walked out in a bra and thigh highs. We went at it. Sammy let me and Anita ge tot know each other and what was supposed to be a 3 some ended up as Anita and i fucked like animals. I think Sammy at one point maybe had her suck him off while I railed her. That evening I put her to bed and woke up next to her. She was facing away I woke up with my normal morning Hard on I woke her up with me slamming into her again I covered her mouth and railed her I felt her tense up and cum I pulled out and gave her ass a pounding. I poured my cum into her ass and we laid in bed kissing. Since then she has asked Sammy over and over to do it again. And we have but I can tell that Sammy is distancing himself and Anita from me. He asked me and is mad for fucking his wife but he asked me. What he doesn’t know is that Anita has come over on her own and has been letting me ride her like a horse for hours. Getting to butt fuck her or bang her in the doggie style position is amazing. It’s hard thing to pass up a women that loves that much Ana’s and begs for me to make that ass clap.

2
# 79562 - by Anonymous / June 6, 2025
- Obsessions -
Straight Male / 35

Secretly A Good Thing

My neighbors next door are a bit older in there late 40 Matt and Natalie. We talk I’m more interested in his wife than I am making friends with him. He was in a bad accident recently and ended up with a broken neck. He is in this brace that limits his mobility. I have always flirted with Natalie she is a fake blond big fat ass that jiggles and she seems to always want to show it off. Some neighbors think she shows to much I like it and since the accident she has been stressed. She had a break down one day while we where talking and that ended with me finger fucking her until she came. It was so intense she squirted all over my garage soaking her leggings she was in suck a daze that I used her mouth to unload my stress. She liked it and now whenever she can sneak out she’s comes over and lets me relax and relive stress. I took her ass and she acted as if she had never had anal before. She admitted that they had tried but she was always not really into it. I told her with an ass like she has it’s a shame not to fuck. She openly admitted that she can’t believe she is actually being slutty as she has always kind of been a prude when it came to sex. I guess she let lose with me because she is acting as if she is one step away from porn. I asked if she would be interested in possibly getting made air tight or a DP. Her husband is in a brace sitting at home and his wife is blowing me taking cock up the ass and thinking about letting me and 2 friends use her as a fuck doll. I have a feeling that if I just had my friends show up she wouldn’t say no. So tomorrow afternoon she is supposed to run errands and have lunch with her mom. She will drive down the road park her car and Il pick her up and bring her back and have 2 of my friends show up while I’m fucking her. Il update how she handles everything

2
# 79566 - by Anonymous / June 6, 2025
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