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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:

- Fetishes and Kinky Sex -
Straight Female / 45

Derby Day Baby

Me and hubby in town for derby. We had a great Friday and we ended up at the hotel bar. Some 20 something, hell maybe 30 something guys… lol were drinking with us. I was a bit flirty and even touchy. I didn’t mind them touching back. The bartender set us up with three or four more rounds and shut the bar down.

Ended up with just one guy sitting at a table in the dark lobby area. We were kissing and he was feeling me up. My husband doesn’t care if I fuck, we usually hookup with couples, like we plan to tonight.. lol. But I did want this guy so I asked. Can he fuck me? My hubby replied so we could both hear. “Only if he sucks me off first and then I’m going to sleep in the other bed.” I thought fuck, that’s a hard no. The guy counter offered. Let’s go to my room. I’ll suck you off and then you leave. Then I’ll fuck your wife until she’s ready to go back to you. I didn’t even wait, I said deal. Grabbed their hands and we were in the elevator. The guy rubbed my husbands cock as we made out. We get to his room and he gets me naked and pulls out the chair telling me this should be the best view. My husbands cock was already hard when he unzipped. In less than 5 minutes my husband came as was telling me to have fun.

Oh my fucking god, did I have fun. He kissed me and I could taste my husband’s cum in his mouth. My pussy was dripping wet as I heard the door shut behind hubby. His cock was long and so hard I didn’t waste much time with him in my mouth. I rode him in the chair to my first of many orgasms. He filled me up twice, which never happens. I’m a condom girl, but the night was full of decisions I didn’t expect. I just got back to our room 9 AM, damn. I’m going to sleep for a few hours. I usually like hubby to fuck me after I’ve been with other men, but I hope he leaves me alone…. lol I’m sure there will be questions.

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# 78798 - by Leigh / May 3, 2025
- True Sex Confessions -
Straight Female / 22

Boyfriend

I've been with my boyfriend for a year and we live together. He is five years older than me. When I was a high school senior my boyfriend at the time fucked me twice. My boyfriend now told me he has slept with more than twenty girls when I asked him. He knows I am unexperienced sexually and talked with me about it. He said he would like me to have some more experience and said I should try other guys now and then if I could see it as just recreational sex.

Last week I slept with a guy who I found attractive. I met him in one of my classes. I went over to his apartment. We made out and his hands were all over me. I told him I was loyal to my boyfriend and could only be friends with him. He went down on me which I love and I sucked him. When he put himself inside me, it felt wonderful. We came together and after some time went by he fucked me again.

I told my boyfriend. He said good and that he hoped I had fun. I did have fun. My boyfriend hugged and kissed me. He asked if I felt emotionally involved with the guy. He was a nice guy, but it was just sex. I loved coming with a new guy, but my heart is with my boyfriend. It's amazing that he let me sleep with another guy.

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# 78800 - by Josie / May 3, 2025
- My Spouse -
Straight Male / 53

Tipping The Guys

Around 15 years ago I was over at my gf's flat when suddenly the ceiling above her computer desk just collapsed and a big portion of the ceiling came crashing down. She was not sitting at the desk at the time so it was just a really big mess but no harm done.
We called the landlord and informed her of the situation. The collapse was near the windows and there'd been a water leak when it rained and it eroded the integrity of this area until it crumbled and the plaster just came cascading down.
Anyway, the landlord sent a couple of men around and the decision was made that they would remove the damaged area and seal up around the windows, etc. and then they'd use a couple of panels of drywall to make the repair and paint it to match the rest of the ceiling when done.
So the work begins a few days later and the two workers got busy with what they figured would be a two or three day job.
The workers were a fellow named Brad who had been there at the flat before doing small repairs over the months my wife, then my gf, lived there. Stuff like replacing sink washers to stop drips. Light repairs and spruce ups. She got along well with Brad.
The second fellow was called Trey and he seemed affable as well.
The men told my wife they would be fine working in the living room and she could come and go as she pleased and if she were out when they finished for the day they'd let themselves out and lock up. They also could come in even if she was out because Brad had a key.
So the first day everything went well. Second day it's kind of a hot Summer day and she made a pitcher of lemonade and some cookies and asked the men if they wanted a little break.
They were very grateful and stopped for maybe 20 minutes to have a cold drink and some cookies.
My wife says they were wearing a tee shirt and shorts and the other fellow had a tank top and shorts. During the afternoon they took off their shirts and worked in just their shorts.
My wife was getting hot looking at these guy's muscular legs and chests and was really horny.
She put on a filmy sheer short little nightie and laid on the edge of the bed and called out to Brad. When he entered the bedroom he saw her laying there and obviously wanting his dick in her mouth. My wife loves to suck cock and she's damn good at it, always sucking and swallowing and she finished Brad off in just a few minutes. When he was done she asked him to send Trey in for his tip too and she took a second load in her belly.
The men were very very happy to come back again for the last day of work and to take some more of her mouth and fingering her holes as she blew them.
Brad said they'd be happy to come over and do any little jobs she needed done.
She actually was very good and told me all about it and we fucked like bunnies cause I wanted to watch her sucking them off but then her lease was up and I asked her to move in with me.
We moved across the state soon after and never saw Brad or Trey again.
Sometimes I tease her when she's blowing me and tell her I wanna call Brad for some handyman work at our house.

1
# 78804 - by Dave / May 3, 2025
- True Sex Confessions -
Straight Male / 53

Moms Friend

This was when I was 17. My mom's friend Susie was a beautiful blonde. Tall, big natural tits and a curvy big ass. At 17 I had fantasized about Susie for a while. They had known each other for years and I had sniffed Susie's panties many times. I would cum in her panties every chance I got! One night Susie stayed all night with us. We watched TV and played a card game then they said they were going to the room to talk. Thinking nothing of it I done the dishes and when I finished I started walking to my room but as I walked past the living room Susie was on all fours completely naked! Ass in the air she turned and said "get what you've always wanted" I nervously knelt behind her, licking her pussy, ass crack and tonguing her asshole. She was moaning like crazy when I slid my cock as far as I could inside her pussy. She felt so fucking good! She said is this better than my panties? I was pumping in and out of her pussy when I noticed my mom barely visible watching me fuck her friend! I'm thrusting away at this beautiful pussy, my mom is rubbing her pussy watching, I couldn't take anymore and exploded inside Susie. Hands down best pussy ever but I think she told mom about the panties and decided to fuck me! I guess mom got a little turned on by Susie's panty talk too! Never happened again and it was never mentioned.

3
# 78808 - by Jungle Joe / May 3, 2025
- Evil Thoughts and Deeds -
Straight Male / 65

I Pretended To Be Her For Information

My wife was sexually active with others early in our marriage, I was generally unaware for the most part until she finally stopped.
Her last affair with a younger co-worker ended up with her getting pregnant.

To shorten the story, she stayed with me and I raised the baby as my own.

I was hurt and angry about the affairs. However years later, she has been faithful and not seeking other guys, I found myself turned on thinking about the other guys having sex with her.

I ask her often to tell my about the affairs and the sex in detail. She has told my quite a bit about some of the sex she had and it always makes me horny and want to fuck her.

The last guy though I have always felt she held back about him some. Maybe because he is the one who got her pregnant.

My wife had an alias Facebook page she made not using her real name. She did this so she could look up groups and other various things without our kids or family finding out and asking questions. Stuff like tattoos, rockabilly, Goth and just other things not really naughty but family might question if they saw it on her FB. I had full knowledge and access.

She had this page a couple of years then kind of lost interest. I hatched a plan to use this now neglected page to look up a few of her ex lovers. I sent friend requests to the few I could find.

The only one who responded was the guy who got her pregnant. She had a few pics posted there that kind of hid her actual identity.

I don't think in the beginning he thought it was her. He accepted the friend request and we chatted some. Pretending to be her, I always tried to lead the conversation to sex. He generally complied but seemed the conversations always lead in other directions soon. I was getting frustrated not getting the information I was looking for. Wanting to escalate this, I posted a couple of pics that strongly gave hints of my wife. He caught on quickly and started asking questions about her, or me since I was chatting. He finally asked if this was my wife. I confessed that it was. That kind of opened the door to him opening up about the sex they had. He asked if I remembered a certain time. Well I of course was clueless about very much of their sexual escapades. I was now out of my element and not able to BS about details. I didn't want to blow this opportunity to find out the things I wanted to know. It was time to bring this to my wife and get her involved.

I told my wife that I had been chatting with him on FB under her alias page. I asked her what she thought of this. She was surprised and a little angry at me, but, she was also curious about the conversations. I fessed up to her my motivations. I told her to remember how I love to hear about the sex she had with her lovers.

She opened the page that night and sent him a message on messenger. He soon responded and she reopened the conversation about his question about a certain sexual event. The place they went, What led to the sex, what they did, etc. It was great sitting beside her while she chatted with him about sex. I sat there with a hard on, getting hornier by the second. I slipped a finger between her legs and she was wet too.

They chatted like this for several months in the evenings. I was able to see the chats and get horny as they discussed their sexual past. I did find out much information I wanted to know.

It came to an end when our adult daughter used the computer one day and accidently discovered the FB page. She thought there was something going on and she confronted us.

We explained that was all just fantasy and it was between her and I. We had to delete the Fb account due to this, and she had to block him from her actual FB page so my daughter would not see him popping up there.

A month or 2 later I created another alias FB page for her using another name. She helped create it and we used a few pics that does not really identify her. We sent him a new friend request but he has not responded to it. I don't know if he was pissed from the abrupt deletion of the other account or what.

I can say, I wish he would send me a friend request. I would love to chat with him about the sex they had. He would probably think that's too weird. I guess it is.

0
# 78807 - by Sladd / May 3, 2025
- True Sex Confessions -
Straight Female / 25

Letting My Boyfriend's Friend

I met a guy during the summer and we started hanging with each other. He was very sexy and the first time he fucked me was on the moonlit beach at Newport. I loved it. On weekends we would go to his friend's cabin at Lake Arrowhead and spend the time getting high and generally having fun.

One night at the cabin the three of us were in the living room and my boyfriend had me lie down on the carpet and started kissing me. I was into it, but then he started to take my top off and I stopped him because his friend was in the room watching. My boyfriend looked at me and in a gentle voice told me it was was okay. For some reason I completely relaxed and he undressed me. He sucked my nipples and played with me. When I was wet he told me his friend was now going to fuck me and told me to enjoy. My heart felt like it stopped. I was high and, as I said, my boyfriend's voice told me I should just relax and I did.

His friend pushed into me and began fucking me. It was like a surreal dream. I was being fucked in front of my boyfriend and I was moaning because it felt so good. When he came in me I almost forgot where I was. Next, my boyfriend fucked me and came in me pretty quickly. For the rest of the summer, I was shared. Between the two of them I was probably fucked a dozen times each weekend. I had never had so many orgasms. I had never had two guys before and I have never had two guys since.

I am married to another man now, but I've never told him about that summer. We have a great sex life, but sometimes when he is fucking me I think about the time two guys shared me and how erotic that was.

6
# 78760 - by Margie / May 1, 2025
- True Sex Confessions -
Straight Male / 28

My College Girlfriend

We were very young when we got together in college. We were full of sexual energy and the times encouraged freedom and exploration. We were living with another couple in a rented house. We were all pretty open around each other. One night I told my girlfriend that I wanted her to sleep with our male housemate and also told him he should sleep with her if she wanted.

A few days later, she took him to bed and they made love. When I asked her if she had fucked him, she said she had and that it was good and his girlfriend was good with it. It was arousing to hear her describe their love-making and I fucked her as she talked to me about it. It was a one-off she said.

Several months later, I came home early because a class had been cancelled. As I came in, my girlfriend was fucking our housemate on the floor of the living room. They were startled, but I told them not to stop and I went to my bedroom. When my girlfriend finally came in, I fucked her really hard. As it turned out, she had been fucking him nearly every day when I was in class. She admitted he'd cum in her over a hundred times. I felt betrayed. And even though I had occasionally slept with his girlfriend, I was angry with him for taking advantage. Until, of course, I realized my girlfriend wanted to fuck him a lot.

I left and found an apartment by myself. My girlfriend apologized, but I couldn't get over it. In retrospect, I think I was okay with her fucking our friend, but when I lost all control over her fucking him constantly, I couldn't take it. So, it was my fault really.

4
# 78761 - by Jason / May 1, 2025
- True Sex Confessions -
Straight Female / 26

Spontaneous Swap

My husband, from the beginning, had always let me know I could have sex with other guys if I wanted. I loved that he gave my that freedom. In turn, I let him do the same, although I tended to be more active.

I met a married guy, Tim, and was attracted to him. One thing led to another and I fucked him regularly over a couple of years. My husband knew. Tim's wife did not. Gradually, my husband and I became friends with the Tim and his wife and we did things together. Three of us knew I slept with Tim, but we didn't talk about it.

One evening we had dinner at their place. I went for a walk with Tim and when we got back, we got in his van before going in and he fucked me really well. A few hours later, we all went to bed with my husband and I in their guest room. In playing around, my husband noticed cum in me and I told him I had fucked Tim earlier. We got to talking and my husband said he would like to fuck Tim's wife. She still did not know I had been with Tim.

My husband and I were naked when we went into their bedroom. I immediately sucked Tim's dick until he was hard and then I got on top and I started to ride him. Tim's wife was receptive to my husband as she watched me fucking Tim. She got out of bed to see to birth control while my husband watched me fucking. When the wife came back, my husband slid into her and fucked her. In the meantime, both Tim and I came and we watched our spouses fucking. The wife moaned loudly as my husband came in her.

Tim and I moved to the guest room and my husband stayed in the bedroom and fucked the wife three more times that night. Tim told me he was a bit surprised that his wife readily let my husband fuck her, although he did say that she had been shared for a few months with a friend a few years ago.

The next morning, we made breakfast and my husband and I went on our way. We never had another swap with Tim and his wife, although I continued to fuck Tim until he moved away. Strangely, years later I visited the city where Tim lived and we hooked up one last time. Tim filled me twice before we said goodbye.

8
# 78767 - by Angela / May 1, 2025
- My Cheating Heart -
Straight Male / 23

Friend Asked Me

I was housemates with a friend of mine and his wife during my senior year in college. My friend's wife Linda was a drop dead beautiful woman with a body to match. She was also a great person and I truly enjoyed them as friends.

After we had been living in the house for about a month, my friend took me aside one night and said he wondered if I would like to fuck Linda. I didn't know what to say. First of all, any guy would love to fuck Linda, but she was married and I didn't know what she thought about fucking someone other than her husband. My friend told me that while he was gone, usually from mid-morning until later in the afternoon, I had his go ahead to sleep with his wife. He said he had told her to fuck me.

The next day, I was home with Linda. She was in the kitchen and I walked up behind her and gave her a hug. I moved my hands to her tits and kissed her neck. I eased her to the floor after pulling her shorts down and I fucked her until I came hard. She seemed to like it, but was not overly responsive. Over the next two weeks, I took her to my bedroom every week day and fucked her. By the end of the second week, she moaned and came with me when I unloaded in her. Not long after, she would come to my bed without being asked when her husband left the house and she would passionately fuck me.

This went on for seven months and I came in her countless times. My friend knew she was fucking me, but he had no idea how much. At the end of the school year they moved away. Several years later I visited them in the city where they now lived. My fiend told me Linda had finally told him that she had fucked me a few hundred times when we were living together. He said he was angry at first, but then got over it and acknowledged that he had asked his wife to sleep with me. The weekend of the visit, Linda came to my bedroom on Friday and Saturday nights and I enjoyed her once again.

It was time for me to fly home on Sunday. Linda was at the kitchen sink. As I had done the first time, I hugged her. She turned and kissed me. She took my hand and we went to the bedroom where she fucked me up until I had to leave for the airport. My friend is okay with all of this and I can hardly wait to visit them again.

9
# 78768 - by Jay / May 1, 2025
- My Cheating Heart -
Straight Female / 28

Weekend Slut

I had a previous encounter with my husband's friend Will. My husband Jack had hinted that he and Will might enjoy a threesome with me. I was noncommittal, but was quietly turned on by the idea. I had never done that before. Will understood what Jack intended and one Saturday night, without asking, they stripped me naked and played with me until I wanted them. I very willingly went along and wanted them both to fuck me. Jack fucked me in front of Will, and then Will pulled me on top of him and I fucked him until he came in me. And, although we were around each other regularly after that night, I did not have sex again with Will for a long time.

But, a year and a half later, Will invited me to his house. Jack was going to be away for the weekend, and he encouraged me to go. I'm pretty certain the guys set me up. I was both apprehensive and aroused at the same time when I thought about what might happen. I imagined Will fucking me and me having Will in my mouth. I almost didn't go. Jack made dinner and afterward we went to the living room and after talking for a bit, we started making out. Will's hands were on my breasts and he rubbed me through my shorts. He finally led me to his bedroom and I sucked his hard penis. I undressed for him and he bent me over and fucked me hard from behind. He filled me with his cum. When he recovered I told him I wanted to be on top and I slowly fucked him until I had a huge orgasm. He fucked me twice more that night and I let him do whatever he wanted.

In the morning, he had me. We showered together and I sucked him until he was hard again. He fucked me in the ass which I had never done before, but it felt good. During the day and through the following night we pretty much stayed in bed. Over the weekend, Will came in me probably a dozen times. I was a complete slut with him. Will asked me if I was going to tell Jack what we had done and I told him I would. I let Will know that Jack got off when he thought about another guy fucking me.

When I told Jack what I had done, he said he was glad I had fun and then fucked me. I told Jack that I had felt like I had his okay to be a slut with Will. As Jack. asked me to give him more details, I did. He fucked me very long and hard again. I told Jack I had felt less inhibited just being alone with Will and did whatever Will asked. Jack said he'd like me to occasionally be alone with Will.

Jack now also fucks me in the ass while he has his fingers in me. I usually have multiple orgasms. The best was when Will and Jack had another threesome with me and while Will fucked my ass, Jack fucked my pussy. It felt like I was being sexually knit by the two guys. It was another first for me. Will has Jack's agreement to fuck me whenever we want. I usually spend a couple of hours each week with Will. I love having two men. I love Jack and I like Will, so things are very good. I love that Jack is so open-minded. I figure this won't last forever, but it's been very erotic to this point. If Jack ever wants to stop, I will do what he wants.

4
# 78737 - by Jana / April 30, 2025
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