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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:

- Embarrassing Moments -
Straight Male / 47

Maybe A Little Too Far...

Me and my wife are both 47 and have been married 23 years. We have had what some would call a "unique" relationship. We haven't had a declared open relationship, but we have each cheated on each other so many times I cannot count. And we both have had this kinda "whatever" attitude about it. We are secure, have stayed together, and even on a few occasions the cheating even made our sex life hotter.
Well last week she may have taken thigs a little too far. I came home from the golf course several hours early (buddy had an emergency so we cut round short). Walked in the house and immediately knew what was going on. My wife is quite "loud" when having a good sexual encounter. I could hear her screaming and it sounded like the living room. I walked in to find her bent over the side of the couch getting fucked from behind. The surprise was who was doing the fucking. It was a 17 yr old kid from down the block! Let me repeat, 17! Now my wife is still hot at 47 and I can't blame the kid. At 17 I would have done it.
I backed out of the room and quietly went into the kitchen to get a cup of coffee. I listened until it was obvious he had finished. After a few minutes of quiet I heard them walk upstairs to the bedroom. The noise started up again and they stayed in the bedroom for 2 hours!
We had a slightly awkward talk after he left. She didn't seem to be too embarrassed about the experience...

1
# 82226 - by Husband / September 8, 2025
- Fetishes and Kinky Sex -
Straight Male / 27

Good Buddy

A good buddy of mine had been flirting with the idea of doing the whole wide swap or wife sharing thing. Apparently he had spoke with his wife Blair and she was on board. Although after all this happened she at the time was 50 50 on the subject. She had agreed to try the wife share thing before the whole swap. She and I had always flirted but nothing went past that. I could never or would never do that with a friend unless he knew and was ok with it. When he agreed to get the MMF she got to live the person and blurted my name out quickly. She did say that she might have sounded to excited to nominate me but she did and he agreed. He would ask me to well help him fuck his wife. He asked me while at his place watching college football. We had a few beers and thought he was joking until Blair walked out in a very short skirt and a tank top with no bra. She had a nice set of tits c cups is kind of short auburn colored hair and from the skirt size a landing strip that was the same color as her hair.it was hot she looked good I felt good we kissed and she started to lean down felt her take my cock in her mouth. Sloppy bj her husband was eating her out we did it. I spent the night and we fucked every chance we got. I slept in the spare room she did as well her husband in there room. I passed out exhausted woke up the next morning to her warm mouth sucking away at me. Came in her mouth showered with her rammed in in her ass a few more times. We all had coffee together that morning and it was weird. From the chair to my lap she was in her panties and that was it. She kissed me I kissed back our hands where all over each other and her husband sat there. To the couch we went her husband initialed sex by forcing her head down I entered her form behind and begged for my cum. Kind of caught he this by surprise how well she liked the situation. Best weekend ever and she has swung by a few turns since and has shared herself with me again. She asked her husband for another night and he has changed his opinion on sharing and now wants to try FFM with her and her friend. Here is the problem she said no to him and offered me the Female female male encounter. I gladly accepted and got to watch and participate in 2 gorgeous women fuck lick and cum in each other then do the same to me. I actually started to date the other girl and when Blair found out she kind of got jealous and started to really slit it up for me. Now I’m banging both and Blair is insisting that I knock her up and claim her. I would not mind either to be honest

1
# 82234 - by Anonymous / September 8, 2025
- Evil Thoughts and Deeds -
Straight Male / 47

Wet And Wild

Wife is a lovely younger woman with a great adventurous streak when it comes to sex. She likes it a lot and is always willing to try something new if either of us wants to give it a go.
So it should go without saying that she's a deliciously slutty 3 hole honey and especially loves sucking cock.
She sure does like being in the middle of a man sandwich and as long as we're playing with someone from our safe group of friends, I like her taking loads in her pussy, mouth and ass.
She's very anal too and that's what I wanted to tell about.
It was when we were at a swinging party in the Spring and I was lying on my back with one of the other wives riding on me cowgirl style and another girl squatting over me and kissing the one I was fucking. Meanwhile my wife was next to me on all fours and getting spit roasted with one guy face fucking her and another plowing into her from behind. She was all wet with spit and pre cum and she pulled off the cock in her mouth just long enough to tell the guy behind her to put it up her ass. He wasted no time and quickly slid his slick and shiny wet cock right up my nasty wife's asshole as she moaned real loudly and begged for more and deeper.
So I was close to filling my rider with my load when the guy fucking my wife's ass grabbed her hips tightly and shoved in balls deep as he said he was cumming. He was kind of rude saying he was cumming in her shitter and grunting as he pumped at least 4 spurts in her anus.
I expected him to just pull out quickly even though that could be painful for my wife, but instead he stayed in her ass and waited til he got soft.
At least that's what I thought.
Next thing I knew he was grinning and my wife was sort of going "Mmmmmm, that feels nice"
and after a bit he gave her rump a pat and slid his soft dick out of my wife and wiped his dick with a washcloth or someone's panties, I'm not sure which he used.
All I know is as soon as he was out of her ass, my wife kissed me long and deep and she whispered that he had pissed up her ass after he cummed in her!
We went together to the upstairs bathroom and I kissed my wife and rubbed her nipples while she dumped the piss and cum enema she had just gotten.
It's not something for everyone, but it was really kinky and hot to kiss while she was voiding that mess that was up her ass.
After cleaning up we had some more fun and she got a couple more loads of cum, in her kitty and in her belly. We're gonna try having me piss in her but need to let her anus relax and rest a few days before taking my fat butt puncher. Ha ha, I rarely do it just cause it's messy, but she loves when I surprise her in the bathroom and piss on her before she takes her shower and gets dressed.

0
# 82213 - by Darren / September 7, 2025
- True Sex Confessions -
Straight Female / 27

Naughty Confession

I recently broke up with my boyfriend and so don’t feel bad about confessing this now.

This happened a few years ago, I was 23 years old at the time. I get a lot of attention from men due to my nice, lean figure, pretty face, long legs and tight round ass but had a boyfriend at the time, so I never really entertained their advances.

My boyfriend just started at a law firm and he was invited to his first annual staff party at a hotel venue. He wanted to take me so I put on a nice, elegant, tight black dress which showed off my long legs and figure. Plus I wanted to make a good impression for him at his new job.

Whilst at the party, I remember having so many men’s eyes on me. Skipping through this quickly, I had a few drinks so got pretty tipsy. My boyfriend however, was getting really wasted and I caught him doing cocaine outside the hotel in the smoking area where we got in a bad argument.

I stormed off, heading to a different floor to cry and call a taxi home. Another older but handsome man from the firm called Tim came to check I was ok. He started by hugging me and sat down with me in a small dimly lit lounge, away from the party. He then put his hand on my thigh and was subtly trying to slide it higher up my leg, which kind of instantly turned me on.

I opened my legs as a little sign to invite him. He ended up fingering me and kissing me on the couch. So glad no one came but it was a quiet space. I orgasmed on his hand.

We then snuck away somewhere private, away from the party and went into the hotel gym and snuck in the bathroom there to get away from people. I got on my knees and sucked his cock. It all happened so fast, he stood me up and bent me over the sink and fucked me from behind.

My gosh his cock felt so good and big. He fucked me so hard, holding my hips from behind, I felt so used, it was great. He came on my face and a bit got in my hair.

We quickly got got cleaned up and I went back down to the party by myself. I told him not to tell anyone, and we enhanced numbers before I headed downstairs. My boyfriend found me and we took a taxi home together. He didn’t know a thing.

The next morning he felt so bad about how wasted he got that he took me out for dinner and bought me g*fts. The whole time I was just thinking how good that fuck was I had with his work colleague.

Over the next two months, tim and I would send dirty texts and pics to each other. I would send revealing pics of myself and he would send dick pics which really turned me on. I met up with Tim at his place for sex on a few occasions. But we stopped because I wanted to get serious with my boyfriend.

Anyway, don’t get in a drunken argument at a work party boys. Your girl might just get pissed and sneak off and fuck your work colleague behind your back ;)

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# 82220 - by Sandea / September 7, 2025
- True Sex Confessions -
Straight Male / 47

Labor Day Niece Surprise

My wife and I have always had a great sex life (toy's, road trip sex semi-public sex) and it continues to get better with changing it up.

Earlier this year I surprised her with our friend who is a server at a restaurant we go to in our bed naked waiting for her. I wasn't sure if she was game or not but then found out that she was. Then our female mail carrier recently let us know that she was interested in meeting up with us to have sex which was great.

My wife (we've both been married before) prefers cock but realizes that she also likes the feel of a woman's body and the smell and taste of a woman's pussy.

Her niece that lives out of state who she is very close to, almost like it's her own daughter and best friend talks almost every day. I didn't realize that they discuss everything including all things about their sex lives.

Her niece came to visit us over this long Labor Day weekend. We took her out to eat, went to different places shopping and enjoyed our time with her.

One night we were sitting around having a few drinks having fun and I decided to go up and go to bed after a long day. They continued to talk about who knows what while they continued to drink.

I was sleeping very sound and got woke up when I thought that my wife had come to bed. She cuddled up to me and started rubbing my cock which I got very aroused. I turned over and started kissing her and realized that it was her niece. I was startled at first and then saw my wife standing in the door way with the dimmed hallway light on telling me that it was o.k. and to enjoy myself because she was going to watch.

I slipped out of my pajama bottom, took off her nightgown and stated kissing her while playing and sucking on her nipples. She guided my hand along with hers down to her very wet pussy and started rubbing her clit. She took her two wet fingers and put them in my mouth as I continued to finger her. I moved down to her pussy and enjoyed the smell and taste. She came squirting in my mouth and on my face which I never experienced before. I licked up her juices and moved up to put my cock inside her but she wanted me to fuck her from behind. She hiked her ass up in the air, face in the pillow and I drove my cock in as hard and deep as I could while I rubbed he asshole. Her juices were running down my balls dripping onto the bed. I came within 10 minutes and she did shortly after.

We looked over to where my wife had been watching and saw her naked with her 7" suction cup dildo stuck to the side of dresser bent over thrusting back and forth while pulling and twisting her nipples. We watched with excitement as she moaned and continued to pleasure herself, and then she came with such intensity.

She crawled into bed with a smile on her face and we laid there for a couple of minutes. My wife kissed me and could taste and smell her niece on my facial hair, and she told her niece that she needed to enjoy the taste of my cum. Her niece started rubbing my cock and got me hard very quickly and licked the head along with my shaft and then slid it down her her throat. The tightness of her throat moving up and down on my cock made me cum pretty quickly. She swallowed and licked up every drop she could.

Early the next morning I was sitting under the patio cover with the gas firepit going when her niece came walking outside naked. She walked over towards me while grabbing a cushion off of one of the chairs and got down on her knees and looked up at me and said thank you for a great time. She took my already hard cock out of my pajama bottom and slid it down her throat again making me cum within a couple of minutes. She said it was a good way of starting her day.

I didn't realize at that moment my wife was watching from the back door while pleasuring herself.

I look forward to the next time she visits!!!

0
# 82165 - by TB / September 6, 2025
- True Sex Confessions -
Straight Female / 51

Spontaneous And Amazing!

I must be getting bolder and sending out some sort of vibe that I’m a slut!! LOL. Being married for many years has always made me be careful how I’ve always talked to men. I never wanted to give them the wrong impression so when anyone would halfway flirt with me, I very gracefully shut it down. But now that I am a total slut, I’m getting bolder and apparently it is working.

I went to the park this morning to read a book. I’ve always loved going to the park and sitting and reading or even sitting in my car and eating lunch. My husband knows that I enjoy this and doesn’t think anything about it. But now more than reading a book, I’m watching all of the men who like to jog or run on the track through the park. Today there were two men probably in their thirties running together. They look like they were friends as they jogged and talked with each other. Even though it’s a little chilly this morning where I live, they were just in shorts and tennis shoes and no shirts. They were both in good shape and in my mind, I was sandwich between them as they had their way with me. LOL. They both had great muscular legs and watching their muscular chests bounce up and down as they ran had me so horny. They both had just some chest hair, which I love. Finally, they stopped about 100 years from me and it looked like they were done. One went to his car and the other started waking towards me. Now, I would not consider myself beautiful but I’m not ugly and I have an Ok figure but I was going to be surprised if he was going to actually come over and talk to me.

It turns out that his car was not too far from where I was sitting. He got in his car and I thought he was going to leave, but he got back out and told me that my wallet was about to fall out of my purse that was underneath the bench. That led to some small talk, and he came and sat by me on the bench. He was all sweaty, and I’m sure that I could not hide the fact that my eyes were saying, “dear God I want to fuck you”. LOL. I surprised myself and while we were talking, I always wave my hands around when I’m talking and I kept touching his leg. It might have seemed innocent, but I was doing this on purpose. I noticed that it didn’t bother him at all, and he even moved his leg closer to me. Finally, I just kept my hand on his thigh as I talked. He noticed my wedding ring and asked if my husband would be upset that I had my hand on his leg. I flat out told him that I didn’t care.
He told me that he was married and that he works in insurance and that he has an office that him and I could use someday if we wanted to meet. He told me that he had to go at the moment as he had a birthday party to go to, but that he thought that we should meet for lunch on Monday. I leaned in and kissed him, and while I did, I ran my hand up his shorts and grabbed his very hard dick. Thankfully, there wasn’t anybody really around.
I looked around and I could not see anyone even remotely near us, and I pulled his dick out from his shorts. It was big and gorgeous. I leaned in and kissed him on the lips, and then put my head in his lap and completely shoved his entire dick in my mouth and down my throat. He grabbed the back of my head and roughly fucked my face. I looked up to see if anyone was around and he said something that was so sexy. He said, “don’t look up slut. I’ll let you know if someone coming. Just suck my cock”. Being told what to do and sitting on a park bench sucking a married man’s dick had me completely wet. When I came I let him cum in my mouth and showed it to him.
He kissed me on the cheek and told me the address and what time on Monday. We exchanged phone numbers. God this is hot!

5
# 82166 - by SunnyHoney / September 6, 2025
- Obsessions -
Straight Female / 51

My Brother In Laws

Since my sexual awakening my mind has been racing with naughty thoughts. My sisters are both married to very nice men. They are attractive men, but I have never really had crazy thoughts about them. I’ve known them for quite a while. But recently my mind is getting very dirty when I am around them. They are both usually just pretty nice as that’s how they dress for work. A couple of weeks ago we all met directly after they got off of work to eat dinner together. It was very nice as all three of us couples got together and had a great time.
This time, though I noticed so much more about my brother-in-law‘s. Yes they have always been nice looking men but now I find both of them drop dead sexy. One has dark and gray hair and he is not very tall but very well built. The other one is well over 6 feet tall With blonde and silver hair. He is very well put together as well. They are both in their 50s but look amazing. They are both very nice man and also very funny.
A couple of times during dinner one of them would get up to go to the bathroom. Both times when they came back to the table, I could notice the outline of their dick in their pants. All I could think about the entire dinner was wanting to be bent over by both of them. I want to please both of them sexually so bad. Good God my mind is in the gutter.

4
# 82169 - by SunnyHoney / September 6, 2025
- My Cheating Heart -
Straight Female / 24

Trucker Husband

My husband is about to start working as a trucker and deliver out of state so he'll be gone most of the time. I can't go without sex too long and I just know im going to end up cheating. How many of you trucker wife's have cheated and what are some tips for me? How fun is it? I could see myself sleeping with at least 3 different men in just the first week. Where would be a good website or place to find men up for some fun?

5
# 82172 - by Anonymous / September 6, 2025
- Anything Goes -
Straight Male / 42

Question For Men

Your wife and her friends go out on a ladies night and find themselves surrounded by handsome fit males. Of course alcohol is involved and the guys approach her group and of course some guy is talking to her and she’s smiling smitten he’s a real charmer.
My question is.. does she want time alone with him and does she initiate it or takes him up on his advances? Has she found the perfect opportunity or the perfect match she’s always kept hidden? Do you think she would go make out with him ? Would she give him her number and maybe make plans to meet up again? Does she just go for it and make out with him and get all she can from him? Now keep in mind no way she can get caught or even noticed.
Do you think she would just have a casual conversation and blow him off. To be totally honest I don’t think I could trust my wife. She was wild when I met her after her boyfriend cheated on her. We met and she secretly dated others since we lived over forty minutes away but worked for same company. I don’t know that she married me for everything I was. She told me she was ready to settle down. She’s always been the aggressor and always made the first move. I don’t know if she was totally in love with me at times. It’s weird because several of her friends have cheated on their husbands and they have no knowledge and two of the four have been divorced

8
# 82217 - by Jon / September 7, 2025
- Women Only -
Straight Female / 28

Breastfeeding

I have a question and confession. I'm a new mom for the first time and I am breastfeeding my son. I didn't want to but the La Leche League talked me into it. I started and the baby wasn't latching on. I was getting blisters and my nipples were bleeding and he was losing weight. I was about to give up. I was in tears. I didn't know what to do.

One morning I woke up when he was crying to try again. I sat in the glider in his room. I ripped my shirt off in frustration. I said come on! You got to latch! Sitting there topless, I put my nipple into his mouth and it felt different! I finally latched on! As he was sucking I sat back and started to finally relax. It felt so much better now that it was happening right. I then noticed that my panties were getting wet and I felt a tingle between my belly button and my pubic area. When he was done eating I put him in his crib and put my hand between my legs. I was fucking soaked! I sat back down in the glider and I fingered myself to an intense orgasm! The next feeding the same thing happened! When he was done I was soaked again. I went to take a shower and used the pulsating shower head to get off this time! What is going on with me?

Does any other moms get turned on when they breastfeed? Is this fuckin normal or is there something wrong with me???

8
# 82187 - by New Mom / September 6, 2025
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