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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:

- My Spouse -
Bi-Sexual Male / 56

Old Friends

My wife came home from work last Thursday and said she ran I to an old friend at a coffee shop downtown. She said his name is Ray and they went to high school together. I said I don't remember you ever mentioning him. She said she had told me all about him but never used his name.
My wife has always been open about her sex life before we met. As a freshman in high school she was involved with a group of older black kids. At first it was just hanging out then it took a turn . It became a very sexual. She has shared some of the stories and they never failed to get me off.
She told me Ray was the guy who started the sex stuff with her. She liked him. He brought a couple of friends over to were she was babysitting and ended up jerking all 3 guys off. Ray returned a week later by himself and gave her her first real fucking. After that she spent the next 3years doing anything and anyone Ray asked her to do. It got crazy.

She asked me if it would be ok to goto Ray's hotel room for a little fun. As long as she tells me all about it, I'm all for a good story

She went Friday night and told me she would call and let me know she was ok.
She got there and knocked on the door. When Ray opened it she saw there was a group of guys. Some she knew from school some she had never seen before.
They brought her in and introduced her to everyone. There was 6 guys there. They immediately took off her clothes and started touching her.Ray said it was going to be an all nighter. She called me at 3 am and told me she would be staying the night.
She got home at noon on Sunday. This is what she said. They used her every way possible. All holes filled. Over and over.
Sometime Saturday a few of them left but within the hour there was a whole new group ready to go. She told me Ray had done this to her may time before. She thinks he charged the guys to come use her. It was non stop the whole time. Someone was always in her. They came in and on her. When she was so covered they would take her to the shower and clean her up. A few of the guys gave her some golden shower which she loves. Then back to the bed for more.
When Ray dropped her off he came in and thanked me for letting her relive the good old school days. I think she needs to fill me in on who she really was in school.
All true. I write more as she tells me more.

3
# 65126 - by Watcherone / April 18, 2023
- Fetishes and Kinky Sex -
Straight Female / 32

Did It For Him, And I Liked It

I have been married for 8 years, have a girl and a boy. My husband is 2 years younger than I. We both stay in good shape, I am still 5ft. 6in, and 120lbs, measurements are the same as when I was married except after two kids, my hips are at 36" now instead of 35". I try to do things my husband wants sexually, I'm pretty open to things he wants. For the last four years he has been trying to get me to go with other men, or other women, and has even admitted his real fantasy is watching me let a group of guys bang me.

I on the other hand have not agreed to the group thing, swapping, or cucking, though I really do like it when other men look at me, and I'd be very satisfied to know several other men have seen me naked. I guess I have a bit of an exhibitionist slant. So I compromised, he wanted me to do a group bukake night. He got 7 guys plus himself, all tested, even though they wouldn't be allowed sex with me, plus himself. As the guys came in, they had drinks and snacks and when all were ready my husband brought me out naked and put me on the tarp in the middle of the living room. The kids were at my mothers so we had the night. It started with an explained BJ to my husband, all others knew it was their hands or sometimes mine only. He pulled out and came a big load on my face that also shot on my neck and chest.

Then the guys all were naked, and all had hard cocks and gathered around me. I used my hand on each guy for a while but not to finish. Then I laid back and let the cum fly. I had 8 pretty large loads on my body. Some came on my pussy, some on my belly and boobs, others on my face with it splashing into my hair. I stayed covered in cum and naked as the evening went on and guys were taking seconds, most of those were one at a time and I used my hand a lot. At the end I was covered in cum and using my hand had cum three times during it.

Now I've always been one who really didn't like mens cum. I only swallowed with my husband because he's my husband, only two other guys before him and those only a couple of times each. I don't like the taste I don't like the consistency, I don't like the smell of it. But with it all over me, knowing it was seeing me naked by total strangers that got them off, I was wet as can be. When all were gone, my husband laid me down and got on top of me and we had incredible sex. Then in the shower, he didn't want me to go in with him, instead he wanted me to clean the cum off him, then do me.

As someone who did not like mens cum, I loved it. I didn't have to swallow any, my husband came on my face, when he made it with me after he pulled out and came on my pussy. I was a cum covered mess, which pleased him, it was sort of like a messy gangbang which again, pleased him, I got to be seen by 7 men who'd never seen me naked or clothed before. I felt like a total slut and whore and I really liked being cum covered.

New things, who would have guessed?

5
# 65166 - by Kylie / April 20, 2023
- True Sex Confessions -
Straight Male / 26

Cuckold Client

Working in a clients home, the guy who hired us said he had to nip out.
Within minutes of him driving away, my colleague and I both heard moaning coming from upstairs.
I went up to find the clients wife naked on the landing carpet using a dildo to fuck herself.
It was an obvious come on, and even being in her late forties she was a very horny looking woman. So opening my trousers I asked her if she wanted to suck my dick.
Telling me we didn't have long, I removed my trousers and boxers, got between her legs as she pulled the dildo out and slid my cock into her. Just as I began fucking the clients wife, my colleague walked upstairs.
He said I was crazy and if I knew who the client was, I'd stop. But I was enjoying myself too much by then and besides she practically begged me to carry on.
With him watching, I fucked her even harder as she pulled me down to kiss her. And I was still banging away when my colleague shouted "Shit, he's back".
I quickly pulled out, got myself together as the clients wife walked into their bedroom.
My colleague was back downstairs and I pretended to use the bathroom, when the client walked back in.
We'd all but finished the job by five o'clock, so only one of us had to go back the following day. Before we left however telling the client one of us would be back in the morning,
he spoke to me and said "I'd like you to return tomorrow".
I now know they clients had spoken together. That's because not only did I fuck his wife twice the following day, he watched me fucking her.
It's their thing and each time I fucked her, she made him go down on her.
He's definitely not someone you'd want to mess with, but each time I visit, and I have done many times since we worked in their home, its him who is the cuckold.

1
# 65209 - by Jono / April 23, 2023
- My Cheating Heart -
Straight Female / 39

Getting Wild

I've been having an affair with Julian for eight months. We met when he helped coach my son's soccer team last summer. He's only 26, but so hot with model looks and a lean 6-foot-4 body. I never planned on cheating with a guy so young, but he was bold and confident and worked me really hard despite the fact that I'm married.

I know that part turns him on. I have never been fucked like I have by him. He's incredibly athletic without an ounce of body fat and as a long, thick uncircumcised cock that is always rock-hard. The second time we had sex, we did it five times in his hot little apartment. We were covered in sweat and exhausted but we couldn't stop making each other come.

Our affair cooled down a bit over the winter but I've found myself becoming more carefree and uninhibited since it began. And what happened last weekend made me feel like I was in my early 20s again.

My husband was away. Julian messaged me to invite me to go and watch his band play at a bar downtown. We live in a big enough city that the odds of somebody who knew me seeing me there were slim. I got my parents to watch our kids and went.

It was warm so I dressed sexy with jeans and a tight polo crop top. The place was pretty busy, but I managed to get a seat at the bar. Julian was playing guitar and doing vocals, and he looked hot as ever wearing a deep-V henley that exposed his inked-up body almost down to his waist. In fact, he was turning me on more than he did when I watched him play soccer.

Their set went on for a while, so I had a couple of drinks. When he was done, he greeted me with a kiss on the cheek. We chatted, and then he suggested he give me a "tour" of the bar.

Knowing there wasn't much else to see, I had an idea what he was thinking. He led me through the back hallway to a staircase that went into the basement. The noise of the bar faded into the background as he opened the door to the office. It was small and cramped, with a leather couch, a desk, and a bunch of beer kegs.

I slammed the door closed behind us and we went at each other right away. He pinned me against the door and engaged me in a deep kiss as he undid my belt. At the same time I managed to pull his pants down, springing free his hard cock which snapped upwards off his belly button. I licked my fingers and grabbed it, pumping it for all I could. When he got my jeans off, he lifted me up and slid inside me from below. I wrapped my legs around him as he fucked me against the door, suspending me in mid-air. As he thrusted to the bass beat of the music upstairs, I came quickly.

We still needed more though, so I got down and bent over the desk. He stripped off the rest of his clothes and entered me doggy-style. Now he was fucking me like a jackhammer while one hand worked my clit and the other rubbed my nipple through my top. I couldn't help but moan loud, hoping the noise upstairs was enough to drown it out. I kept twisting my head to look back and see his hot body, and he grabbed a handful of my hair in his hand - not too rough, but just right. The music wasn't enough to drown out the loud sounds of his torso slapping against my ass, and it was soon clapping at a breakneck pace.

I was being pounded into ecstasy and I could feel a massive orgasm building. I could tell Julian was close to coming too, but right at that moment the door opened behind him and bumped into his back. It was one of the employees with empty bottles.

For a split second I was terrified, but Julian didn't stop.

"Get the fuck out of here man!" he called out, elbowing the door closed. All I heard behind it was a crash of bottles. With a final few thrusts, I came hard and so did he. I bucked my ass hard up into him to feel every inch as we both groaned loudly, almost oblivious to the fact that there was somebody outside. He came inside me and both our juices poured down my legs, which were suddenly so weak I didn't want to stand on them.

I turned around and sat on the desk as Julian laughed and fell into a kiss with me. We knew it was going to be awkward leaving that room, but after we dressed and opened the door, the guy was gone. Instead, a couple of broken bottles were on the floor. Later on, Julian said the guy meekly apologized to him.

6
# 65271 - by Naomi / April 27, 2023
- My Spouse -
Straight Female / 56

Wanting More And To Try New Things

As I’ve aged I’ve seemed to get way more horny for whatever odd reason. It even surprises my husband who claims he’s always horny

As of last year out youngest child moved out to go to college so we’ve been having the house to ourselves a lot of the times. Perfect time to have more sex if you ask me and do it wherever we want! We’ve fucked on the living room couch more then a few times now lol

Recently I’ve been wanting to try anal again. Last time my husband and I tried anal was back in 1996 when I was 29! Been a long time! My husband’s 60th birthday is coming up and i want to have him fuck my ass. I have been craving it

My husband has a pretty big dick. Little over 7 inches. Thick and uncut. It’s truly a nice dick and I want to feel it stretch my ass open again.

I’m just wondering what he’ll think when I mention I want anal. I’ve really stepped up my bj game over the last year so asking him to fuck my ass shouldn’t be an issue

4
# 65245 - by Paula / April 26, 2023
- Fetishes and Kinky Sex -
Straight Male / 51

We Were Not Those People Until We Were

We are not "those people". I am a successful businessman, My wife is an elementary school teacher. My friend Matt is also a businessman and his wife is also an elemntary teacher in a nearby state (we live very close to the state line).

My wife and I have been married for 11 Years . Last year I convinced her to go topless on a beach, and then to go completely nude in Jamiaca. It seemed to give her confidence that I wouldn't be judgemental of her character (she's always be a very good girl with very strong morals). But I've known another side of her in the bedroom and the way she gets with dirty talk, toys, and kinky sex (iike bondage). She's also beautiful, standing 5'8", 140 lbs with 34 DD breasts (she's had a boob job but they are the most natural ooking I've ever seen). One of the things I would talk dirty about was showing my friend Matt some photos of her nude. She would always get extremely turned on and wet when I mention it. One day I showed him a few photos, and he obviously got turned on, so I created a reality out of one of the things I would talk about when we had sex. I confessed to her that he had ACTUALLY seen her, and what he actually said. That led to her sending my selfies or me taking photos. Some she would approve of me showing him but she never wanted HIM to know she knew he was looking at them. She preferred that he thought I was doing it on the sly.

About a year passed she she became to trust Matt would not tell anyone and became comfortable with him seeing her completely nude top to bottom. Our sex began to include a real feel dildo attached to the headboard while she gave me a blowjob. My dirty talk would include asking her admit she fantasized about a threesome and liked a c* ** from behind while giving me head. Once night when I had heavy poured her 3 margaritas, she admitted she fantasized about being in a 3 some, and even admiited that she would only consider doing it ONE time and ONLY with Matt. Of course I was sharing this information with Matt, and he was willing to participate if I could set it up.

One day I had my wife about as intoxicated as possible while we were hanging out by the pool. It was Fall, but warm enough to be outside, but too cold to swim. Matt's wife was out of town on a girls trip so I saw my chance. I invited him down to hang out and drink. When her arrived we started talking openly about things we'd never done. At some point my wife said she'd never cold plundged, so we all agreed to do it. She mentioned changing into her bikini, and I said, "Oh hell no. We are skinny dipping if we do it." Matt smiled, and said "I'm game!" My wife said, "Men first!" Matt and I stripped off. I watched my wife staring at Matt as he undressed. She never took her eyes off him. When we was naked, we jumped in. My wife stripped to her panties, exposing her tits as if Matt was not even there. I pushed her against the pool wall and started kissing her and playing with her tits. I asked Matt if he thought she had nice tits, and he said they were the best looking tits he had ever seen. I told him that she'd had a boob job but that looked and felt real. I told him to feel of them. My wife never objected. As he felt her tits, he began to pinch her nipples, which she LOVES. I started pinching the other one then ran my hand down to her panties. I was suprised to find Matt's had, and her panties off. He was fingering her as I was kissing her. The pool light was on, and I look and noticed my wife had his c**k in her hand stroking it. She was getting so excited, and I felt it was time to mention a 3-some, which none of us had ever done. I grabbed her by the hand and led her out of out of the pool. We made it as far as the sofa in our poolhouse. I sat down on the sofa and she sat beside me. Matt sat on the other side of her. She grabbed my cock and then leaned over and started giving me a blowjob. Matt slid over and reached down to pull her legs up on the sofa and turn her so her ass was turned toward him. She pulled herself up to her knees, giving him to opportunity to enter her doggie style. She grabber her by the hips and I saw him guide his c*** inside her. I heard her let out a groan of approval. He was nailing her so hard, she was gagging on my c***. When we bothed finished (and she'd come twice), had got dressed and left and we went to sleep. She and I talked about it the next day and many times since. She loved it, but said she only wanted to experience it once, and would not want to do that again. To this day, we've told nobody and it remains a secret between us 3. Matt and of often talk about it also.

3
# 65200 - by ToddS / April 23, 2023
- True Sex Confessions -
Straight Male / 47

Corrupting A Housewife

I met a housewife online in a sex chat room. Her husband had put her up to it, as he’d wanted to watch. She was a goody two shoe type who’d never strayed from her role as wife and mother.
I took it upon myself to degrade her. For about a year, we’d have cybersex or phone sex when her husband wasn’t around.
I got her to the point where she was sending me any nudes I asked for. I even asked for one of her with slut written across her breasts and she did it.
We finally met up in person and she looked like a soccer mom. We shared deep wet tongue kisses in the back of my car. I got her to take her top and bra off and sucked the nipples on her huge tits. She stroked my cock, which she knew I loved and I fingered her. She was so wet.
We met up again later in a hotel room and she undressed and bent over and let me s***mize her. We were both talking filthy and I kept telling her how slutty she was for having anal with me before anything else.
We still meet up. I love that I’ve corrupted this nice little woman to the point that she has to go home and be a mother after I’ve degraded her. I hope I ruin her.

4
# 65205 - by Jack / April 23, 2023
- Fetishes and Kinky Sex -
Straight Female / 19

Married Young

I have been married for 5 years, which gives you an idea of when I got caught with an older boy who was 19 at the time. We were having sex and my parents, father is a deputy in our county, made my boyfriend marry me. We had a baby within 10 months of getting married, and another a year after. I went on BC. He is good to me, sex is good for him, I've let him do it whenever and wherever he wants. He loves to make it in my butt. But in about 5 and a half years or so of having sex, I've never experienced an orgasm from sex.

My husband had 3 girlfriends before me and he says all of them did it, and loved it, said he was the best. He says it's all me and until I can get into it and get my own orgasms he's doing all he can. I know he has cheated on me with at least 4 other girls. I don't care honestly, it's less I have to take care of him. As it is, I still get sex at least 10 times a week if not more. I know he didn't want to marry me, I'm pretty chubby, was big back then too and he likes tall thin blonde girls best.

He's the only one that has ever had sex with me, I don't know what I'm doing wrong, but after two kids and over 5 years of sex very often. I want to orgasm.

7
# 65045 - by Tamm / April 12, 2023
- True Sex Confessions -
Straight Female / 36

My Bold Night

Through my husband's suggestions and my own needs, we started swinging. I was very reluctant not because of the sex, I love sex. I was worried people would find out, my husband would lose respect for me, I'd be violating my values and my vows. It took a long time and some fits and starts but eventually we swapped with another couple, then another, then a threesome with a guy, then a few more swaps and each time it got easier but not all that fulfilling.

My husband brought up watch me with a single guy. After I agreed, he changed it to watching me with a black guy. I started out thinking, yeah it would be fun then started thinking more and more and was getting so it the idea I was horny all the time.

My husband met a young guy on line who was interested. He was 24 and hung and looked cute but a little scary. He had a look that screamed aggressive and I was nervous what he would do to me with his big dick.

We met him at a bar-restaurant. He was inside. We couldn't find a parking spot. I was nervous but feeling bold and asked him to drop me off and meet up later. I took a dep breath, went in and boldly walked right up to the guy and gave him a nice kiss on the lips and a little hug and he ordered drinks.

Before my husband showed up we had hit if off and we practically sitting on op of each other. He was very young and surprisingly I ended up being the aggressive one. I was touching him, squeezing his cock under the table, pressing my tits against him, encouraging him to touch me. He was very nervous about my husband and I was left wondering if he'd even fuck me if he could. He was attracted to me, his cock was hard the whole time we were sitting together.

My husband texted said he was headed in, I told him to wait at the bar. I asked the guy where he was parked. He was in a lot behind a supermarket across the street. I said lets go. he paid, we walked. I never saw my husband. I texted that I would me him at the car later.

We got onto his front seat. He wanted to talk. I found out he was a lawyer just starting out. I didn't really care. I rubbed his dick and unzipped him and pulled out a beautiful stiff dick. he was uncut. My husband is uncut so I was an expert. He was in mid-sentence when I devoured his cock. He was squirmy and nervous but I yanked his pants off, massaged and sucked his balls and he finally shut up and relaxed while I did my best to pleasure him without letting him cum too soon.

he did have a beautiful dick, about 8 inches and thick but not too thick to take deep all the way. I made love to his dick with my mouth and when I was ready I sucked him slow and steady with a firm wet grip and soon he was ready to cum. He warned me a few times he was getting close, I kept going until he dick throbbed and he came. I savored his cum before swallowing. He was relaxed and said that no one had ever swallowed his cum before.

I exchanged numbers with him, texted my husband to see where he was and had my new friend drive me over. He dropped me off, I gave him a deep sensual kiss, and walked over to my husband with a bit of a proud strut. I was actually very proud of how bold I'd been. I met the guy on my own, got him hot, into his car and pleasured him with no help from my husband. I wished that the guy had been as aggressive as I feared he would be but he was just a kid and nervous.

I met him once at a hotel. Spent the night just me and him. I asked my husband to let me go solo. It was nice but he was just as nervous and even more timid about the sex. I got us both naked and lay him on the bed and spent an hour sucking his cock before making him cum and swallowing it again. Then we rested and soon I was using my hand and mouth to get him hard again. He never took command though. He did suck my tits, and played with my pussy but never took over. I ended up riding him until I came then rolled him over and encouraged him to fuck me missionary which he did. I liked it, his dick felt great inside me and I came again and he finished inside me after i told him too.

I decided not to meet with him again because I need a man to take charge of me in the bedroom. I've had much more success with that since this first guy but I still feel a burst a pride when I think of how bold I was that night and how much it's impacted me since. I can do just about anything sexually now and I truely enjoy my life.

2
# 64963 - by Kayla / April 7, 2023
- Fetishes and Kinky Sex -
Straight Male / 42

Wife Has Fetishes I Never Knew About

I’m 42 years old, my wife Stephanie is 36. She’s blonde, 5’5” tall, about 120 lbs, small breasts, and beautiful blue eyes which are the sexiest thing about her….even sexier than her perfect ass. About 2 years ago I learned something about her I had not known in our 7 years of marriage, she is an exhibitionist and she has a submissive nature when it comes to sex. I found this out by accident when she and I were on vacation in Mexico. We were lying on the bed in a cabana on the beach and I had been snoozing. I woke up and saw her adjusting her bikini bottoms so that her pussy would show to anyone walking by. Once she had it properly positioned, she lay down as if she was sleeping. Guys would walk by and stop to peek and even a few girls as well.

After a bit, she propped herself up, still exposed, and guys would stop and say hello. She carried on conversations with them knowing her shaved pussy was visible. She soon loosened her top so that her nipples could be seen if someone stood in the right spot. This went on for a couple of hours. I finally sat up and told her she needed to adjust her swimsuit and that I would see her in the room. I left and she followed me a few minutes later. I asked her about why she did it and she explained she loves to expose her body to people and has been doing it for a long time. We talked a long time and began discussing other turn ons. That’s when she told me she liked for a man to be dominate with her and wanted me to try it. I gave it a try, but it’s just not my nature and I could tell it wasn’t what she was looking for. Still, I’d tell her when we were on the beach to remove her top, or loosen the ties on her bottoms, or to flash someone and she seemed to love this.

We were at a bar a few weeks later, it was crowded and the only seats were at the bar that was filled primarily with men. She and I were talking and she kept asking me to tell her what to do. I knew people could hear and I was embarrassed but I finally told her to go to the restroom and remove her bra and panties and come back out with her shirt unbuttoned except for the bottom 3 buttons. She got up and went to the restroom. 2 black guys sitting on the other side of where she was sitting were laughing and looking at her as she walked away. One of them asked me if we were “players”. I wasn’t sure what he meant, but told him no. He then said my wife was hot and he couldn’t help overhearing our conversation. He said I needed to be firm and demanding with her, make her step outside her comfort zone because that’s what she wanted. I just smiled and turned away. I ordered another round and then went to the men’s room passing my wife as I did. I told her I’d ordered another round and would be right back. I noticed her shirt was unbuttoned even further than I asked and she smiled showing me the tiny g-string in her purse as she walked away. Her skirt was very short and she was intentionally swing her hips as she walked causing her skirt to flip up in the back giving everyone a glimpse of her ass.

I walked out a few minutes later and back to my seat at the bar. Stephanie was turned sideways now talking to the black man who had been giving me advice a few minutes before. I sat down and took a sip of my drink and listened as they talked. I heard the guy, name was Shawn, tell her that he and his friend, Tee, wanted to dance with her. She laughed and said maybe later but he then said “No, not later NOW. Get your sexy white ass up and dance with us.” With that, he stood and grabbed her wrist and led her to the dance floor with Tee following close behind. She looked back at me and shrugged then turned back toward Shawn and walked out to dance. Tee and Shawn had her sandwiched between them. The floor was crowded but Shawn had made sure they were in a spot where I could see. Both were grinding against her and running their hands all over her sides and hips and ass. He leaned over and said something to her so she turned to me and opened her blouse flashing her small titties.

A couple of songs later and they came back to the bar. When they sat down Shawn closed his tab and told her “We’ll be at my car out the door and to the right. Tell your guy where you’re going and join us in a couple of minutes.” She started to speak and he said “Damnit! Don’t keep me waiting. Tell him and get your ass out there. He can come too if he wants, but you get that ass of yours outside fast.” With that, he and Tee walked out the front door. I looked at Stephanie and she said “Baby, I can’t help it. I’m SOOO fucking turned on right now. Do you want to come with me, or wait in here?” I told her I’d come too and closed out the tab. I headed out the door and saw her already with Shawn making out at his car. When I walked up he told her where they were going and for us to meet them there. To be continued…

1
# 64555 - by Mike / March 17, 2023
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