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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 -
Straight Male / 32

First Couple Swap

My wife and I responded to an ad from a married couple who were interested in swapping partners for a night. We agreed to meet at a restaurant to get acquainted and to see if things should go forward. We all had a nice time and found that wee were very compatible with one another. We were all about the same age, had some interests in common, and found the couple to be attractive both socially and physically.

I suggested a drive up into the local mountains and talk some more while enjoying the drive. The wife got in the front seat next to me and my wife got in the back with the husband. As we drove, after about twenty minutes, I heard my wife moan a bit which she did when I sucked on her nipples. I looked in the mirror and could see my wife naked from the waist up with the husband kissing and playing with her breasts. My wife was kissing his neck and pressing his hand to her breast.

The wife also saw what was going on and murmured that they should not have all of the fun. As I drove, she unzipped my pants and soon had taken my erection fully in her mouth and was sucking and moaning as she fucked me with her mouth.

We found a mostly empty campground and parked in a seclude spot. By this time, my wife was completely naked. I heard her moan as the husband starting fucking her. A few minutes later I was slowly fucking the wife. I heard my wife say she wanted him to cum in her and I could tell she had another orgasm as he shot into her. I asked the wife what she would like and she told me to cum in her when she had her next orgasm. We finally dressed. All of us had been fucked well and told the wives how good they were at fucking. They returned the compliments.

We drove back to the restaurant and dropped off our new friends. My wife and I went home and talked about how much sexual pleasure we had gotten. We then fucked each other silly. We did laugh about acting like teenagers out parking in the woods. Next time we will invite them to our home and comfortable beds. Actually, this was our first sex with another couple and it went well for both of us. My wife had been shared before with a friend which she had liked and that had led to us thinking about getting together with a couple.

3
# 80253 - by Dillon / July 2, 2025
- True Sex Confessions -
Straight Female / 31

My First Threesome

I divorced from my husband three years ago, we had been together since I was 18 so he was the only real man I had been with. Getting divorced meant I could now explore and find fun. I had a couple of dates and went with two guys on nights out but nothing really ever panned out from that. Then came October of that year. Our work had a conference in Birmingham and the plan was to have a night out on the Friday just before Halloween. We all started drinking about 1-2pm time so started quite early. By about 8pm most people were either heading back to the hotel or going for food. But myself, Jamie and Frank all decided to stay out and drink more then go into a nightclub. The three of us had shots and more drinks and even somehow got into the upstairs area of the club that was a it more swanky but none of us ever remember paying to get in.

It got late so left the club, all feeling quite drunk we opted to not get a taxi back to the hotel across town and split the bill to pay for a room at the Hilton hotel across the street from the club. We got in feeling quite drunk I flopped on the bed while the guys talked and joked around getting dressed. I can remember talking to Frank on the bed and then kissing and bit really remembering what we talked about but I know we was both in bed in just our underwear and hugging. Jamie was sat down on a chair and then he said he wanted to get in and I said ok, next thing Jamie is spooning me and both of them had their hands in my panties. Feeling the mood and feeling brave and drunk I returned the favour and felt outside both their boxers and jerked them feeling how hard they were.

After some kissing and touchy feely moments with each other i pulled my bra and panties off and the guys took off their boxers. Not thinking about it as both guys lay on the bed I took turns sucking them both and jerking the other while giving the other a blowjob and swapping back and forth. I can’t remember which guy did it first but one got up and got behind me and started licking me while sucking the other and then the next thing I know I’m feeling his cock go in me. That was officially my first spit roast while I was laying over the other guy. Soon I was laying there on all fours and both of them took turns fucking me and I did climax a couple of times. Jamie then told me to lay down so I did and he lay on top of me and fucked me again. They both had turns doing that with occasional moments of having one fucking me while looking up and sucking the other cock. My legs in the air or being pulled outward they both had their way and would go hard and fast and deep and slow. Both pulling out to take a break and let the other in. I remember Jamie cumming in my mouth and jerking himself over me and Frank partly cum in me but pulled out and cum over my belly. But officially that was my first honest threesome and would open the door to what I would go hunting for and still do today on a couple of different sites.

2
# 80209 - by DivMadisonLuvs3Sums / July 1, 2025
- Fetishes and Kinky Sex -
Straight Male / 45

When Her Exhibitionism Was No Longer Enough .

My wife likes me to watch her using sex toys and dildos . She likes to watch porn when she is doing it . My favourite toy is a rabbit vibrator with rotating plastic balls in the shaft . She has a stong orgasm when she uses it . She gives me a blow job to make me cum . She has used the rabbit vibrator in my butt . When she wanks me . She wanted people to see her doing things . We had to drive to a dogging site so that she could open the hatch on our car . Letting her undress and lay there using her toys . Where people could see her . I sat looking over the back of the seat at her . The first time a woman came over to lick my wifes pussy and make her cum . I wanked watching them . When a guy licked her and fucked her . I was cumming in my clothes without wanking . I wanted some of the action . I sat with my legs outside the car naked from the waist down . My first experience was a guy giving me a blow job . When a woman got on her knees to give me a blow job . I asked her to stop . I told her i wanted to fuck her . When she stood up i turned her to face the seat . I lifted her dress and pulled her panties down fucking her . My wife wanted to watch me fucking strangers .

3
# 80220 - by Carlo / July 1, 2025
- Lesbian Stories -
Bi-Sexual Female / 49

It’s Funny, When You Give Up On Something, It Finally Happens

I work with a woman in the cardiac care unit, I’m a tech, she’s a RN. We have been friends since she started at the hospital…. Fuck me, in 2011. My husband and I are swingers, she and her husband are not. We are couples friends and her husband definitely figured out our “deal” early on. I’m sure she and her husband talked about us. My hubby and I have attempted to cut her from the heard a few times. You know, cut the unicorn from the cows. She is curvy like my hubby likes, big tits and ass. I have fake tits, and zero ass. But here’s out itch to scratch. She’s hairy. Not crazy hairy, trimmed triangle, shaves her legs, but mmmmm, hairy pits. Love a hippy, my husband begs me to grow my pits out, I fucked up and had laser many years ago. Smooth kitty and pits, so what do men want, the opposite of what they have. What do I want, to make her cum and squirt like I know I can.

I gave up trying to get her naked 10 years ago, although when she finally broke down when we were out on our boat and couldn’t hide her hairy pits. Showed hubby and me her furry kitty, I thought we were back in the game, but she sobered up and snapped her legs shut after show me yours, I’ll show you mine turned into some touching. My husband’s big cock seemed to spark an interest, but it didn’t go any farther. During the miserable time that was Covid, I stayed with them several times. They lived close to the hospital so the endless shifts were better if I spent 10 minutes round trip to there place and not 45 minutes each way to mine. I almost gout her husband to fuck me, by that I mean, we talked about, we kissed, I took my tits out and I rubbed his, smaller than I like” cock, over his pants. He wouldn’t give in.

Two weeks ago my now best friend and I were having drinks after work, a bottle of wine in we went to her house. Her hubby was out of town. The empty next is hitting her hard. I called my husband and told him I was staying over, he simply said, you bitch. lol. Right, I think that would have happened by now if it was going to. I was wrong. Watching Yellowstone and drinking she said, I bet barrel racers are fun. I sat up from leaning on her hip as we lay together in her family room. I bet they are, at least the ones I’ve been with have been. You’re bad she said out loud for the millionth time since we’ve been friends. But this time she looked at me with the kiss me look. I did and we were naked together the entire night. Licking, kissing, I spent 30 minutes in her right arm pit as she fingered me into a squirting O. On the way back to work in the morning I called my hubby. Yep, I’m a bitch. No fucking way he said as he hit the rumbles on the interstate. Tell me, please. I’ll do better than that, you are going to fuck her with me tonight. We’ll see you there after work. I thought I made her cum. I honestly think my hubby’s cock is the biggest she’s ever had. So naive, she barebacked him like a slut.

0
# 80234 - by Tami / July 1, 2025
- My Cheating Heart -
Straight Female / 27

I Cheated

I am a mom with a 4-year old daughter and have been married for six years. I have a professional job which took me to a conference a few months ago. Some friends at the conference introduced me to an attractive married man. We hit it off and I did something I had never done before. I wound up in his room and we made out on the bed. He took off my top and bra and played with me, but we did not have sex. The next day I was back in his room and we both were naked. When I said I could not have sex with him, we decided to each masturbate until we came. I had a giant orgasm and watched as he pulled himself and came on my breasts. I had never masturbated before with a man watching me.

What we did broke through my boundaries. We moved together and he rubbed his penis across my clit until I held it and pushed it into me. I groaned as he went fully into me. I had multiple orgasms before he came in me. I took his penis in my mouth and sucked until he was hard again and then I fucked him one more time.

The conference ended the next afternoon and I flew home with terribly mixed feelings. I had very much liked the sex. It was passionate, it was exciting, it was uninhibited. But I also felt guilt for what I had done. I did not love my husband less, but sex with another man overwhelmed me. I wanted him in me. A lot. I have no intention of looking for more sex outside of my marriage. I am treating it as just a one off. I have not told my husband. But, I wonder if any other women have been n my situation. I wonder if they told their husbands? If so, I wonder how their husbands responded?

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# 80226 - by Kendall / July 1, 2025
- My Cheating Heart -
Straight Female / 21

Start Of A Fun Summer

After I finished my second year of uni last summer, I was back in my hometown staying with my parents and got a job in a local pub to earn some cash and stave off the boredom. It was run by a couple in their thirties. The woman, Sarah, handled the business and her husband Joe, managed the bar.

It quickly became clear that Joe fancied me. I didn’t mind as he was hot in a ruggedly handsome older guy kind of way. Plus he was Irish and Irish accents are just sexy. We would flirt whenever his wife was out of earshot. He’d compliment my outfits and tell me I made him wish he was single.

One weekend, Sarah went away to visit her parents. After a busy Saturday night, Joe and I found ourselves alone after close. I’d been planning on going out with a friend, but she’d bailed at the last moment so with nothing better to do, I agreed to have a drink with him.

As we chatted I could feel the sexual tension between us. He started gently stroking my arm as our faces grew closer. I knew he wanted it and so did I. When he pulled in for a kiss, I didn’t say no. We started making out passionately as he ran his hands all over my body.

We were both lost to the heat of the moment. He leant me over the bar and pulled down my shorts and thong before burying his tongue in my pussy. I was soaking wet as he ate me out like a pro, fingering my arsehole until I came right there and then on the bar.

I barely had time to catch my breath before he took me by the hand and led me upstairs to his and Sarah’s bedroom. We fell onto the bed and frantically tore off the rest of our clothes. My skin was on fire as he explored every inch of my body with his hands and mouth.

He absolutely worshipped my body; I don’t think he could believe his luck to have a naked 20 year old girl in his bed. I begged him to fuck me and he didn’t need asking twice. We got a condom from his draw and he slid into me, his magnificent dick completely filling me up.

We started with slow, deep, passionate missionary. As he looked into my eyes, he told me how tight my pussy felt. He gradually picked up the pace until he had me on the edge again and we rolled over so I was on top. I started riding him furiously while he played with my tits and told me to cum for him. I had another mind blowing orgasm, and collapsed onto the bed.

We lay there for a few moments, my body quivering as he traced my curves with his fingers and told me how beautiful I was. I was aware he hadn’t cum yet and asked him how he wanted me. He told me to get on my knees. Soon, he was inside me again, hands on my waist as he pounded me from behind.

The whole bed was shaking from the speed and intensity of his thrusts. I couldn’t help but notice the feel of his wedding ring against my skin. It made me feel so naughty. I could tell he was close and I egged him on, telling him to fuck me harder until he couldn’t take it anymore. I asked if I was better than his wife and it sent him over the edge. He cried out, “so much better,” as he came.

We caught our breath, talking about how amazing it was, and how much he’d fantasised about fucking me. I asked if I could take a shower. After a few minutes, he joined me and we caressed each other’s wet, naked bodies until we were having gentle standing sex, pressed against the wall.

I knew it was time to go home and he called me a cab as I got dressed. We agreed not to say anything and after making out one more time, I finally left. I slept so well that night and was in such a good mood for the next few days that my parents wondered what had gotten into me.

The next time I saw Sarah, she was completely normal and friendly and I knew she had no idea what had gone down between me and her husband. I wish I could say I felt guilty but I didn’t. Joe and I continued to see each other in secret for the rest of the summer. We only managed to actually have sex a few more times, but whenever we did we made the most of it.

By the time summer was out, we’d hooked up in his car, in a nearby field and all over my parents’ living room and kitchen. He’d fingered me with his wife in the next room and I’d sucked him off and swallowed his cum in the pub cellar in the middle of a shift. He turned up on my doorstep one night with a bottle of wine and lube, and fucked my arse while I was tied to the headboard of my single bed. I could barely walk the next day, but it was fucking great.

It was such a thrill sneaking around with him, knowing how much he wanted me, knowing he was prepared to risk everything just to have me. I loved having an older, experienced man satisfy me in ways guys my age rarely did. He loved having a sexy younger girl do all the things his wife wouldn’t in bed.

Neither of us caught feelings and we ended things amicably when I went back to uni. I’ve been thinking about him a lot recently as in a few weeks time, I’ll be heading back to my hometown again. I’m sorely tempted to hit him up.

5
# 80194 - by Throwaway809 / June 30, 2025
- True Sex Confessions -
Straight Female / 44

My Friend - The Set Up

A few weeks before it actually happened, while having a Friday night cocktail, I told my friend Danielle that I fantasized about black dick. It ended up being the topic of conversation the entire night. When I got home, I masturbated to interracial porn. I came and came and came until I fell asleep.

A few weeks later, same bar, Danielle introduces me to Grant. Grant is 56, 6’4 235 pounds, grayish beard, bald head and black. Ten minutes later Danielle says she is going home and to enjoy the evening. Grant and I had been set up. We decided to make a night of it. A couple of hours later Grant asked if I was interested in coming home with him. I was, so I followed him to his house. I called Danielle along the way and she said enjoy this g*ft I have set you up with. I am the best friend ever. As I got there, I noticed cars in the driveway. I asked Grant about it and he says Danielle must not have given you any information about tonight. I questioned what information. Grant told me he and his friends planned to gang bang me tonight. I called Danielle but she only responded with the devil emoticon. Grant felt bad and did not push. At this point, I was horny and excited for my first interracial experience. If I went inside, I was sure to get gang banged, not that it was bad thing. I asked Grant if I could sit in my car for a few minutes to think this through. He went inside. I immediately found a bbc vs white girl gang bang to watch. It would at least give me a bit of in medication of what it was look like. Ready, super turned on open to a new experience, I went to the door and knocked. Grant answered and asked what I had decided. I handed him car keys and told him to give them back after everyone had been fully satisfied. As I entered the house, I was faced with six middle aged black men, knowing all of them would be inside of me this evening.

It started with everyone getting naked. I was on my knees sucking each dick until it got hard. One guy eventually found my pussy. He found me covered with a silky coating of pussy juice and made sure everyone knew I was fully enjoying this. I was taken to the couch. I rode one guy, sucked on another and took another in my ass. This round robin of dick went on until they all started to cum. One by one they would pull out, rip off their condom and jerk off on me. All six coated my tits, stomach and face with their cum. Afterwords we called this break halftime.

During the break, I responded to a few texts from Danielle. She knew what had happened to me and encouraged me to keep going. I did not need any encouragement. I would allow anything at that point.

The second half was more of the same. Black dick in all of my holes. No boundaries were given except for the use of condoms during sex. I gave my entire body to this group of men the entire night. After overtime (a round in the morning), I was given my keys back. I went home gaped, worn out and fully used. I smelled like sex. I lost my panties and bra - I went home in stretch pants and my blouse. When I got home I immediately showered the filth away. As I hit my clit with the bar of soap, she woke up. I ended up masturbating in the shower. I finished and slept the day away.

1
# 80187 - by Regina / June 29, 2025
- Wet Stories -
Bi-Sexual Female / 30

This Started Everything

My husband and I have been married for 9 years

It was his 34th birthday I wanted to do something special for him so we went to a strip club. He had never been and I figured why the hell not

As we were at the bar this couple came up to us and said they were swingers who were looking for another couple. We had never thought about swinging but we were celebrating so I looked at him and gave him the nod of approval. The other couple brought us back to their place

Their house had a pool and a sauna built into the pool house. They asked if we wanted to chill in the pool and we said yes. The other couple started removing all their clothes until they were fully naked in front of my husband and I. They were both very fit he had a six pack that could deflect bullets and her boobs we’re so perfect I couldn’t take my eyes off them. So I started removing my clothes and my husband followed me. We all stood there naked admiring eachother. The other couple complemented both of our physiques. As we all slid into the pool the man motioned me to come sit next to him. So I did and his wife sat next to my husband. She began stroking my husbands cock under the water. I could see my husbands huge erection sticking out of the water with her hand stroking up and down. I was so horny watching this beautiful woman jerk my husband off.

Her husband reached down and grabbed my thigh he slowly traced his fingers up my thighs leading right to my pussy. His rough hands were so gentle as he placed his fingers on my clit and began to rub. I let out a soft moan and his wife giggled that’s when his finger went all the way inside me. I couldn’t handle it anymore I was so horny I told him to sit out of the water. As he sat on the concrete I took hold of his dick it was MASSIVE. I opened my mouth and began to suck his cock.

His wife enjoyed watching me suck her husband. She straddled my husband and began riding his dick I could hear her moan. She rode my husbands dick like there life depended on it. And with her husbands dick in my mouth it wasn’t long before I was swallowing his load.

We all got out of the pool and there was a bed in the pool house we all went in there and fucked like rabbits all night long.

My husband came inside her three times. Her husband came inside me then she ate his cum out of my pussy. They told me to lay under her so I layed my head under her pussy as my husband fucked her again right over my head as her husband fucked my pussy. she began to squirt on me and that made my husband cum again. As my husbands cum dripped out of her pussy onto my face l felt her husband cum inside my pussy again. I was covered in all of there cum. I felt like a dirty little whore

We fell asleep covered in cum and when I woke up the next morning her husband was cuddling me HARD AS A ROCK so I sucked his dick again.

We left and never even got their names

3
# 80176 - by Alice / June 29, 2025
- Anything Goes -
Straight Female / 42

Breaking In The New Guy

This guy got hired into the shop where I work. He’s younger, maybe 19, 20, 21 maybe. I’m not sure. Cute guy, tho. Tall, lanky, scruffy brown hair. He was put into my sector where there were now 5 of us. He was quiet at first, but he quickly started joking with us and fit right in.

One time, after a couple weeks, just the two of us were sitting in my car on lunch and he let slip that he and his gf hadn’t had sex since they moved into their apartment 4 months ago. He tried to explain it as tho she worked 2nd shift so they rarely saw each other. I was just like “oh ok that must be it.”

Last week we got hit with a heatwave and it was unbearable in the shop. I would brag about going home and sitting in my pool. It’s an above ground but there’s a deck around it. Everyone would moan about how jealous they were. When we were alone on break I told the new guy who should come over for a swim sometime. He laughed that his gf wouldn’t like it but I just asked, “You’re on different shifts, right?”

This past week he asked me privately if the offer was still on the table, because of the heatwave. We arranged for this past Friday. He ran home to shower and get his suit after the day. I wore what I thought was my best bikini. I’m short, 5’3, but curvy. Not fat, but big boobs, wide hips, round butt. Brown hair, and a trimmed pussy (just a small patch). We swam for about an hour. I flirted, teased, “accidentally” flashed cleavage and ass. I’d get a little too close, then break away quickly. I could tell it was working, even if he didn’t give in.

After I got in my “rinse-off shower”. It’s just a standing single shower with a curtain, but it’s outside the house by the basement sliding door, under the deck. I told him to join me. I was still wearing my suit, and after a little prodding he climbed in with me. It was a solo shower so it was cramped. My big breasts were pushed against his. My hand “accidentally” palmed his crotch and immediately sprung to action. I was surprised I could feel some real length to it, if a bit on the slender side. I said “ What do we have here?”

He tried telling me I was very attractive and he was obviously turned on but his gf and…. I cut him off asking if he jerks off. He said “What?” And I told him it’d be no different than if he jerked off to me. As I said this I slid my hand into his swim trunks. He had a bulbous head, and I traced it with my fingers before wrapping them around his shaft and started stroking him. I kissed him, biting his lip and sucking on his tongue. I could feel he was getting close to bursting so I pulled him from his trunks and started pumping him vigorously. He moaned as he released right against my belly button. As you’d imagine there was quite the mess, but he felt a lot better.

After we cleaned ourselves up he left. I told him to come for a swim again.

1
# 80178 - by Mallory / June 29, 2025
- True Sex Confessions -
Straight Female / 32

Business Trip Affair

Before I even get into this, I know this was wrong. It sort of just happened and quickly at that.

I am married with two kids. While on a business trip I slept with another man. It wasn’t planned. It was never a thing for me. It did happen and I allowed it.

After a long day on the convention floor saying hello to hundreds of people, a man appeared as we were breaking down the booth. Tall, fit, black, direct, sexy, well spoken, dressed sharp. His eyes - fuck those eyes woke up all of me.

Tony and I went to dinner that night. As I was getting ready my brain and my body were in turmoil. If I went, it would be cheating. If I went, what if I actually went home with this man. It was just dinner, right?

We meet in my hotel lobby and hit one of the hotel restaurants. It was about 7:00. Early enough for me to go to bed late and still get my late morning flight the next day. I had a sundress packed just in case a side meeting came up. He was in slacks and a golf shirt. Dinner was very good. The conversation was very good. He finally asked me about my wedding ring and family became the discussion. He asked me why I accepted his dinner invite. I told him it felt right. I asked him why he asked me. He told me I looked sexy, available and his type of woman. He apparently likes married white women. I told him I had not been with a black man. He assured me I would be satisfied.

As we sat in the booth his hand found my thigh. My pussy felt like a bolt of lightning hit her. I could feel my sundress moving and exposing more and more of my leg. I was horny and nervous. By the end of dinner he had felt my hairless pussy and had stimulated my clit a bit. There was no going back. As we ordered dessert he whispered may I join you in your room tonight? I smiled, blushed and said yes.

The next 20 minutes felt like an eternity. Dessert, paying the bill, the elevator ride. When we got into my room the gravity of the situation hit me. I would be fucking a black stranger in the next half an hour.

He was much taller than me. As we kissed, he pulled off my sundress. My white bra and panties were the only remaining barriers. Off came his slacks. His navy blue boxer briefs were his only remaining barrier between my willing hands and his bulging groin.

We walked to the bed kissing. I sat on the edge, pulled down his boxers and out popped the most amazing cock. Silky smooth, dark like the night, tight mushroom head, tight but big sack. ‘Fuck!’ Yeah, I was very embarrassed when I said it out loud. I tugged it a bit and then I took it into my mouth. For who knows how long, I worshipped that heavenly cock. He eventually laid me on the bed and devoured my pussy. He even licked my asshole…fuck that was hot.

He then dragged me to the side of the bed. He pulled out a sleeve of condoms and put one on. He tossed the others on the bed and said yes, I plan to use all of them. There I was: naked, on my back, knees up, legs open, with a hung black man in front of me putting on a condom. His cock has so big.

He pulled me close, found the hole and slowly entered me. Inch by inch he pushed, my pussy taking him deeper and deeper. The noises from my mouth were incoherent and vile. Out of nowhere I yelled just take it all! Without any hesitation, he drove balls deep into me. I saw stars. He proceeded to fuck me senseless through two cums. As he came the first time, he pulled out, pulled the condom off and came all over my boobs and belly. I watch as ropes of cum shot out of the flared open head. I stroked it; I had to feel it. He got me a towel and cleaned me up. While he was gone I tasted his cum.

He never went soft. He just fed me his cock. I sucked him hard and on went another condom. This time was a marathon. This time he had no regard for anything. He just fucked me until he had to cum again. He pulled out, hopped close to my face and pulled off the condom. I grabbed his ass and shoved his cock down my throat. I swallowed it all and made sure he was empty and clean.

We laid there naked touching each other for about an hour. He told me I could suck it again if I wanted. I so so so did. I even licked his asshole, much to his pleasure. He fucked me two more times that night, using all of his condoms. He left around 4:00 am. That was it. I fell to sleep naked.

8
# 80156 - by Nellie / June 29, 2025
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