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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 / 20

After Rehearsal

Ok, so I've been dying to tell someone about this since it happened, but due to the nature of the situation, cannot. I'll try and make it short and sweet. So, my sister (26)recently got married. I gained a nice, new BIL(27). I met all of his family a few months ago, and I have to say his Dad..Jack,is so hot. Def eye candy. He's like mid 40's(looks 30's easily) 6 ft. 3ish or something, really good shape, blue eyes that just sparkle at you! He always makes me a wet mess when I'm around him! lol. Although we never say too much about it, I believe he has the same effect on my Mom(40) because I've watched her eyeing him every time we're around them. So, at my sister's rehearsal, everything went well except I decided I wasn't going to spend the entire evening there and was going to get my mom to take me home earlier. Upon hearing this, my sister said Jack, was having to leave early as well and she would see if he would mind taking me home. He said it was no problem I was totally welcome to ride with him. Little did I know JUST how he meant that, but would soon find out! From the minute he said he'd take me, I started fantasizing about him. In the car with him I was so on fire and hoping he would do something. He didn't. He just kept talking and eyeing my legs and short dress. I felt like he liked what he was seeing, and I wanted him to just pull over and take me. He didn't. He waited until we pulled up at my house, wanted to check and make sure it was ok before driving off(which I loved! But, I believe he was also making sure no more family, or anyone was home.) By the time we got back to saying "Bye" he leaned down to hug me. I felt his arm around my lower back, and he pulled me in tight and said"I hope you don't mind me saying this, but there is such a gorgeous girl in your sexy dress!" He immediately added"I could have that backwards, it may be a very sexy girl in a gorgeous dress!" He was still holding me and I could feel myself starting to soak my panties! He asked which it was and I just kissed him...right there. His hands were immediately under my dress exploring. When his fingers made it to my panties, I was right, I was sopping wet! He pulled his fingers out to show me, then quickly stuck them in his mouth and licked them clean(God, I loved that!). I quickly yanked his zipper down and found the most beautiful, big, thick cock I have ever had! I seriously couldn't reach around it. It was so freaking hard, too. There was like an inch or more between my fingers and thumb! He picked me up and carried me into the downstairs den, laid me on the sofa, and literally ate me like no one ever has, EVER! I came the same way...like never before. At least 5 or 6 times. When he spread my legs and entered me, I was already spent. He def stretched me out! It didn't take long before it was feeling so incredible each deep stroke! My clit, was riding his entire length, back and forth. He fucked me into 3 more orgasms and when it was his turn, for some reason(and I had never done this before) I wanted to taste his cum, and feel it pumping into my mouth. And boy, did it. It was a lot! It wasn't near as bad as I'd always imagined cum tasting. Actually, in the moment, I was feeling so slutty, and loving it!! He, was cumming so hard. I wanted to show him I could please him. He just kissed me, and told me I was fucking amazing!( his words and I loved it!) Before I got up, he bent down, kissed and licked my well used pussy, and thanked me for being so yummy and hoped I might want to do this again. He also reminded me that it went without saying"This is our secret, ok?" I easily told him yes on both things. I def wanted more. It was a bit awkward seeing him with family at the wedding. Hoping to have a repeat soon. I noticed my mom checking him out several times again, too. When it dawned on me, how he knew his way around our house so good. He carried me straight to the downstairs sofa. Like he had been there before.Then, it hit me. I bet he had been there before....with my mom. I don't know what to do now. How to find out. It just seems weird now. It's def messed me up wondering now.

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# 78892 - by GiGi / May 8, 2025
- True Sex Confessions -

A few years ago, my husband kept the kids while I went for a visit with my best friend from college. Sunni is the sexiest woman I know and not surprisingly she is often involved in polyamorous relationships. I knew when I planned the trip that she was living with two men and another woman, but I didn't care. Little did I know that it would come to matter very much.

I arrived on a Friday night, planning to leave a week later. When I pulled up outside the house, the first thing I was struck by was how small it was for four people living there. Imagine my shock when I learned that there were actually five in residence!

Sunni came out wrapped in a sarong, a glass of sangria in one hand. She was followed by three of the hunkiest guys I've even seen and two equally good lucking women. New Mexico might be a retirement mecca, but evidently there was a shortage of young flesh. Certainly, it was on display that night.

Clearly I had overpacked since Sunni's housemate and lover, Claris handed me a not so large rectangle of silk as a sarong with instructons to change. Since the desert heat was searing and my luggage had disappeared I obeyed, dressing in a tiny bathroom off the living room.

When I came out, Sunni hugged me. I could feel her strong but slim body through the thin layers of fabric between us. The scent of jasmine wafted from her hair and a subtler female odor and I was suddenly curious about how often she shared her body with the gorgeous people she lived with.

Did they have a rotating schedule? Were there threesome, foursomes, or (with the new addition of Leilani)moresomes? It would have taken a huge bed if they did because the guys were all above 6 feet. The smaller two must have weighed between 225 and 250 lbs. The third, a guy who looked a lot like the Black and Samoan wrestler The Rock was 6'7"probably weighed 280. There wasn't a spare ounce of fat on any of them.

Suddenly I was curious about the sleeping arrrangements. All of the house I'd seen so far was a tiny bathroom and a small all-purpose area with a couple couches, a refrigerator, sink, and stove. Neither couch looked like a pull out and the house wasn't large enough for a guest bedroom.

"Where's my bed?" I blurted

I must have blushed because Sunni laughed and said that she guessed that I was tired and would appreciate a lie down. She said that a siesta was customary and not to worry. Everyone was about to take a pre-dinner nap.

My thoughts went from where I'd be sleeping to with whom!

(to be continued...)

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# 6342 - by Anonymous / September 24, 2005
- My Spouse -
Straight Female / 64

Back In The Day

Years ago, not long after we were married and we were in our late 20s, my husband Kent hinted at me fucking his best friend John. I did not know quite what to think because I had never been shared before. The idea of fucking John was alien, but also exciting in a forbidden way. Kent had clearly mentioned fucking me to John. When John came to visit us, the guys got on either side of me on some big pillows in the living room the first night. Before long I was naked while both guys were still dressed. As they played with me and got me wet, they took their clothes off. I sucked Kent while John fucked me. I lost my breath when he entered me. Both John and Kent are large. I went with the guys and let them have me. That was my first time with another man since I had married Kent. It was exciting to have John. I orgasmed with him and he filled me with his cum. Kent loved fucking me after John had cum in me.

From then on, for the next ten years, whenever John would visit us I would fuck him several times. When John finished, Kent would fuck me. In between visits I was monogamous. During visits, I was a slut encouraged by my husband. John fucked me hundreds of times during those ten years. None of our friends or families knew I was shared. It was an erotic and sensual time. A couple of times, I spent several days alone with John when I visited family in his city. We were in bed most of the time.

I'm in my mid-60s now and Kent and I are monogamous and have been for a long time now. But we do reflect on how incredibly sexy it was when John was fucking me. Kent would watch sometimes and join in, but often I was with John alone and tried a lot of different things with him. Kent and I still have great sex when we talk about the times I was shared.

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# 78868 - by Janelle / May 6, 2025
- My Spouse -
Straight Male / 28

Group Sex

My wife and I have been married for three years. Deb is a pretty, slender woman with a very nice body. We were invited to a party with two other couples we know. The invitation had a hint of possible sexual activity. My wife had been shared a couple of times with the husband of one of the couples. At the party we all had a great dinner, good conversation, and we got high. Our host suggested going to the living room. After a bit, he started making out with his wife and eventually took her clothes off. My wife and I started playing with each other and watched as the couple starting fucking. That completely broke the ice. Before the evening was over, my wife had been fucked by the two other men and I had fucked the other women. At one point I heard my wife, who was fucking the guy she had been shared with before, that it was good to have him in her again. When I finally fucked Deb, she was full of cum. It felt great. The three couples have gotten together for sex three more times. It's more uninhibited each time. I watched Deb at the last one with two dicks in her.

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# 78860 - by Caleb / May 6, 2025
- My Cheating Heart -
Straight Female / 51

The Time I Cheated On My Husband

My husband and I got married when I was 23 and he was 24. We had a great marriage and sex life up until about the time I was 34. After 2 kids our sex life just decayed to once or twice a month plus we really didn’t do anything as a couple ever.

At the time I was working at a grocery store in the small village we lived outside of. Being 34 and not having a lot of sex made me so horny constantly. I wanted sex daily but my husband didn’t.

The owner of the store was a 65 year old guy. Super friendly guy. He was friends with my parents too. Me being super horny I always noticed he had a really nice bulge in his pants. It’s like he positioned himself in his underwear to show off what he had

As we were talking one day about marriage he told me that his ex wife stopped having sex with him for years before they finally divorced and he hadn’t been in a relationship since. So I told him my husband only wants sex once or twice a month. He was surprised to hear that and said why would he not want to get you naked daily at his age.

So I hit on my boss that day. Honestly I didn’t expect it to turn into sex but it did. In his office in the back of the store I was unbuttoning his pants and pulling his briefs down.

To my surprise out flops a big uncut dick! Way bigger than my husbands! And uncut was not something I expected to see. I told him this is a big dick and he said that is what I’m told

I began to suck it thinking I’d just give him a bj but I took my pants off and my panties. I got on his desk and laid on my back. He stood up and stuck that big dick of his right in my hairy pussy. The sex was quick because we both were excited. He cummed in my pussy saying I could hold it any longer to which I told him that was really hot.

From that day on every day I worked he fucked me. I was on the pill so he always cummed in me. I can remember the first time I wore a thong for him. He had never seen a thong on a woman in person and it made his dick so hard.

The days my husband wanted sex we usually had morning sex. Those usually were on my days off but my husband wore a condom so no cum was in my pussy if my boss fucked me the same day

I even got curious to try anal and let my boss stick his big dick in my butt.

The sex with my boss went on for 3 years. My husband and I ended up moving so I quit that job and had to break the bad news to my boss that I wouldn’t be near by anymore. He wasn’t mad at all he just said I’ll get a good few fucks in then you should work it out with your husband

After my husband and I moved we started having regular sex again so my cheating secret is still with me but my husband is unaware

5
# 78862 - by Sarah / May 6, 2025
- True Sex Confessions -
Straight Male / 48

Dogging In England

My wife is obssessed with dogging . I told her i had seen people from the road . Who must be dogging . She wanted to see them . The following weekend i took her to look . It was in a big car park in trees and back from the road . There was the trunk of a long tree down the centre of the car park . Dividing it in two . All the cars were facing this tree trunk and they had their headlighs on . I parked away from them where it was dark and turned my lights off . A man was walking up to the passenger door stroking his cock . We could see him with all the lights behind him . My wife asked me what he was doing . I told her he wanted her to wank him . She asked if i was joking . I told her to wind down the window and wait . He came up to her door . I asked if she was going to help him now she had invited him . She reached down and wanked him . When he had cum he turned and walked away . She pulled her hand in and got the wet whipes out of the glove box . Whiping it . She was watching the people over near the tree trunk . Men and women . There were women with thier dresses lifted up . Leaning over the trunk and getting fucked . When the man had cum . He pulled his trousers up and got in his car to drive away . The woman pulled her dress down . Getting in her car and driving off . There was a man on his knees giving a blow job . A woman sitting sideways on the seat of her car . Getting her pussy licked . My wife had her hand in her knickers rubbing her pussy . I was wanking in to a tissue . Everywhere we looked people were having sex . My wife wanted to join in . I told her to go for it . She walked up to a young guy and spoke to him . The next minute he had her leaning on the log . Fucking her . When he had cum he walked back to his car and left . She came back to the car telling me to feel her pussy . My hand came away covered in cum . My wife licked it clean . Driving home she told me she wanted to be fucked by a line of men . When one had cum and he pulled out . The next one fucking her . This idea turned me on . The next time we visited . My wife was talking to a group of men . There were 10 of them . She was bending over the log . One after the other they all fucked her . When the last one had cum . She walked back to our car . Wanting me to put my hand under her pussy . She held it there . When she let me pull it away . The palm of my hand was full of cum . A mixture from all the men . She told me to lick it clean . I had to swallow all that cum . Then she led me over to the log . Leaning over it for me to fuck her . Her pussy was still full of cum . It was too wet . She made me fuck her . She talked about being fucked by all those men . This got me arroused enough to cum . When i pulled out we both walked to our car and we drove home . She wanted to have more men fuck her . It never happened . Once watching them was enough for me . The following day when i went to the car . Her seat had a big stain on it and some moist cum . I showed her . She got down to lick it . It turned her on . In the house we fucked on the couch . My wife has looked for all the dogging places on a map . There are a lot within 30 miles of us . The nearest one is only half a mile away . In a supermarket car park . My wife likes me to take her to them . She gets out of the car to have sex . There are only a few couples there . Most of them are singles . All strangers . I have been fucking a woman leaning over our car . With my wife facing me leaning over being fucked by a man . Everyone is normally anonymous . But we got to know two othe couples . We all got together at each others houses in bad weather for sex . Using separate bedrooms . Also all of us having sex together in the lounge . I have leaned to suck cock and let them cum in my mouth . I get blow jobs from other men . I ge t blow jobs from women . Some must be older than 70 . My wife gives blow jobs . We enjoy watching each other . Sometimes if i am fucking a woman . My wife stands next to me to watch . I stand next to her when she is getting fucked . She likes to wank me and another guy at the same time . Anything goes . Sometimes we get to know a man or a woman and take them back to our house for sex . Mostly we are all strangers . Sometimes I drive past the car park in the day . I saw cars leaving by the back corner and following a dirt track . One day my curiosity got the better of me . I had to drive up the track . It was a long drive . Up and down hills . I could never have done it if it was wet . It must have gone on for over a mile and a half . At the end of it it stopped in a small wood . There were 7 cars in a small car park . With 6 women and one young guy . I talked to them . The women used this place in the day . When their husbands were at work . To have sex with each other . Or with a young guy .

1
# 78867 - by Oscar / May 6, 2025
- True Sex Confessions -
Straight Female / 34

Sexual Depravity

I am a 34 year old white woman. I have been married 10 years. I have 2 daughters. I work at a dentist office. From the outside, I appear to be your every day 34 year old, living a normal and happy life.

About 4 years ago, on an otherwise normal morning, we had a patient come to the dentist. He walked in and my world changed. It was like my mind, body, soul and pussy all disconnected and made me into a bumbling mess. 6’, fit, very well spoken and flirty, all wrapped in a sexy dark skin exterior. His name was Jeffrey. Noticing my discord, he gently says to me ‘finish what you are doing, I am in no rush.’ I go to the back, regain some composure and return to my desk. ‘How can I help you?’

Jeffrey was there for a cleaning. It was his first visit as he just moved from out of state for work reasons. He mentioned his newness to the area. His address was in the next town over. He noted he was single as work kept him out of the dating scene. He was flirty and it brought some flirty out of me too. I told him if he had questions about the area he should feel comfortable enough to ask me anything. He eventually sits and eventually is taken into his cleaning.

When he came out, his smile and words took me over. He asked for his next appointment and I made it for him. He said thank you and said the words that changed me - I hope that isn’t the next time I see you. My pussy went hell fire on me. My mind went completely into the gutter. My mouth, completely out of character says ‘you know where to find me if you want to see me again!’ He walked out and all I could do was try to squash my immediate regret. That night I made sure my husband fucked me good. He did, but Jeffrey was in my mind and in my pussy the entire time. That night, I rode my husband until he begged me to stop. I slobbered on his dick until he came in my mouth.

Two days later, Jeffrey calls the office. I am shocked but I hold myself together. He asked me to meet him after work that day. I could have said no, but I accepted his invitation. My mom was getting my kids off the bus anyways. We met at the park and I ended up in his car. I was so fucking horny. The park was empty and before long we were touching hands, kissing and going down a very bad road. I could feel hell fire burning underneath my thin (and damp) leggings. I was incredibly vulnerable.

His hand found my pussy. My mind told me to stop but my pussy won the day. I found is dick - holy fuck! Just as he finds the inside of my pussy he says do you want to take this to my house? I should have declined but my pussy won the day.

As we entered his house, I felt like a whore or a slut. I still could have backed out, but the kissing and touching was too good. I unbelted his jeans, pulled down his boxers and unconsciously got on my knees. Without any hesitation, I started sucking his gorgeous black dick. As hell fire burned in my leggings, his hands found my hair and my head. He encouraged the slut to come out of me. I willingly allowed it to come out. I sucked his dick into a frenzy.

He pulls his dick out of my sloppy mouth, walks me to the couch, pulls off my leggings and my soaked panties. He opens the table and pulls out a condom. He puts it on, strokes it on his dick and lays me on the couch. He kneels down, spins me to the edge and enters me. I am full. He is deep. He starts to fuck me. There is no love here. He is fucking me. My legs are hooked in his arms and flopping around as he slams deep into me. I feel him getting me. I tell him to fuck me harder. I tell him to fuck me faster. That is when it happened. I had my first black dick orgasm. He made sure I was okay and kept fucking me. For the next hour and three condoms later, he had taken my pussy as his own.

I got home that night and I had trouble looking at everyone. I was a slut that day and nobody was the wiser. As much as a had regret, I desired Jeffrey’s dick. I wanted it again. I would do anything for it again. He would have me anytime he wanted until January 1st, 2022.

On New Years night, my husband and I got hammered. While going in with a bang, Jeffrey came up. Matt ran with it and we roll played it. The next morning we talked about it over breakfast and we decided to incorporate Jeffrey into our sex life. Jeffrey is no longer hidden from my husband. Jeffrey is my lover and has access to my body as he desires, just like my husband.

3
# 78828 - by Angela / May 5, 2025
- True Sex Confessions -
Straight Female / 19

Slept With My TA

I'm a first year college student. Needless to say, I have several intro courses that are required. I've let two different teaching assistants fuck me in hopes of getting good grades. The first TA was an attractive guy and I let him fuck me in his office. I simply told him I wanted him. I sucked him and swallowed his cum and when he was hard again I fucked him and he came a second time. He generally worked at night on his dissertation and I would come to his office to have sex with him for most of the semester. I got an A. I'm actually a pretty good student and can get As without help. But, I love having control through sex. I probably need to change, but I like the sex with smart guys.

7
# 78843 - by Janelle / May 5, 2025
- True Sex Confessions -
Straight Female / 30

My Boyfriend Husband Gave Me Freedom

Andrew, my boyfriend of about five months, moved to another state. To be honest, I didn't know if that meant the end of our relationship or not. We kept in touch with regular phone calls, messages, and so forth. He also came to visit me. I slept with three guys while Andrew was gone, but I told him about them. After three months, I found some time and went to visit him. We spent three weeks doing all sorts of things. We had an incredible time together. At the end of the three weeks it was settled. We were very serious about each other and we agreed I would move in with him five months later when I finished up my responsibilities. We were definitely committed. Andrew had a long conversation with me before I left and told me that while I was away, he was fine with me having sex if I wanted. He had earlier been okay with me fucking guys before we agreed to live together, so this was no change in his attitude about my sex life.

About a month later, I told Andrew I had been sleeping with a guy I met. I did let the guy know that I would be leaving in a few months to be with my boyfriend, so any relationship would be very impermanent. I generally spent weekends and a couple of days each week with him. I loved being fucked regularly, especially knowing Andrew had given me a pass. Over the four months that I was intimate with my friend, he would fuck me four or five times during the week and on weekends he would cum in me seven or eight times. We both liked sex and we fucked a couple of hundred times I am sure. At the end of four months, I said goodbye and moved in with Andrew. The guy was a bit hurt, but I reminded him that I was absolutely clear that I was going to Andrew despite sleeping with him so much. I fucked him a couple of times before I got into my car and drove away with his cum in me.

When I moved in with Andrew, he wanted to know what I had done sexually and I answered all of his questions. In fact, hearing some of my stories turned him on. We continued with a great sex life together. We had been together for about a year and a half when he set up a threesome with a friend after I agreed to fuck Andrew and his friend when he persistently asked me to try it. I wondered what Andrew would think watching another guy cum in me. The guys alternated fucking me one night. After that, Andrew liked watching. I fucked the friend a dozen more times after Andrew urged me to continue sleeping with him for a while.

Andrew and I are married now. Over the past six years I have been shared with four guys. Andrew still gets off on knowing someone has fucked me. I love having a strong and loving relationship with Andrew. He is not threatened by me having another man's penis in me. He knows, although I have fucked other guys dozens of times since we've been married, that I am in love with him without any reservations. Andrew is wonderful to let me enjoy sex with others. As for me, I see it as very pleasurable and I love having orgasms with a variety of men, but to me they are just with friends with benefits and are no threat to Andrew.

9
# 78841 - by Jillian / May 5, 2025
- My Cheating Heart -
Straight Female / 37

Meet From Swinging Website

I'm 37 and have been married for 14 years. We have two children.
A friend at work introduced me to a swinging website a couple of years ago. I only used it to chat with men for a little excitement.
Recently I have been chatting with a man who has been pushing to meet me. I've had this before and never given in, but this man was insistent and had interesting messages.
I don't do much without my husband, so it would be suspicious for me to go out on an evening on my own, so that's always been my excuse not to meet.
This man told me to make the excuse to go to the shops for some milk, and he would meet me close by with some milk so we could have sex in the time I would have gone to the shops.
I didn't have an excuse so said yes. I was excited to meet him.
He had parked his car near a park that is very close to my home. He wasn't messing about and was waiting with the milk.
He already had the passenger seat fully reclined and he got straight to touching me every where and we had unprotected sex. Thankfully it was quiet as I was very worried that we'd be noticed.
He was a lot older than me, in his late 50s, but something about him just made me give in. He knew what he wanted and I found that exciting and flattering.
I do feel guilty. I don't want to be too risky but I do think about meeting him again.

3
# 78811 - by LaraL / May 4, 2025
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