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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 / 47

Widow

I have been a widow for 9 years with two grown sons.
At a party two years ago when I was 45 I met a handsome man who was 34 at the time.
We got drunk and he seduced me. We had sex. He impregnated me. On July 4 last year I had 8 lb baby boy
One night stand changed my life forever
Now here I am a 47 widow with toddler boy and changing diapers at my.age.

5
# 79829 - by Marlo / June 17, 2025
- My Cheating Heart -
Straight Female / 48

Kinda Cheating

My husband lets other men fuck me. I’m not saying I don’t enjoy getting fucked. It’s different sex. It’s a little risky and that makes it hot. My husband likes to watch men with larger cocks fuck me and I do two things with that. I pretend I can barely take the Bulls huge cock and I make fun of my husband for having a small cock. My husband’s kinky fantasy is for me to get pregnant by another man. Home hiv tests with 20 minute results has really made me just say “sure, fill that pussy up”.
I recently had sex with a black man for the first time. My husband was involved, he watches. He has begged me for at least 15 years to take the taboo, at least where and when I grew up, taboo BBC, but unlike the normal process of my husband setting me up from online dating sites or apps. This guy fell into my life. I flirted, seduced him, set the rules and ultimately got fucked by him.
My husband worked late last night and then went to drink a few with his friends. Yes, a few of his friends have fucked me.
I decided I needed another BBC. This time he was a reply from double list. He came over, I got on my knees but he asked if he could take a shower. Let’s just jump in the pool I suggested. The neighbors got a pretty good show, most have seen me topless many times. We have a pretty secluded area where the pool is located. The three story homes can get a decent view through the trees if they really try. We also have couches and a covered outdoor kitchen with a four top bar that is completely hidden. After we played in the pool we went over to that area. As he walked with his black horse dick hard on, I actually thought to myself, wtf have I gotten myself into. We kissed and I got on my knees, then he sat on the couch and I sucked him some more. As I slid up his body to sit on his dick he picked me up and put me on the bar. The smooth concrete bar top was cool on my big ass. His hands went under my legs and opened me up. He was really rough with his tongue as he flicked it around on my clit. It wasn’t bad, but I was way past ready for him to fuck me. So I told him fuck my married white pussy.

He bent me over the barstool his large hands took both my breasts. My skin is so white the difference in our two bodies looked like a black skirt with white top. He fucked me deep and hard until I came. We kissed as he took me missionary on the outdoor couch. I rode him begging for his cum, until he flipped me over doggy, and filled me until it dripped.

My husband came home late and I acted like I was mad. Normally I would not had a problem feeding him my pussy after a date, but I want to keep this memory all about me.

2
# 79814 - by Leigh Anna / June 17, 2025
- Evil Thoughts and Deeds -
Straight Male / 29

They Where Right

I had a few co workers tell me that the foreman and his wife were swingers. I always took it as a rumor and didn’t think anything until a few months back when after a long week he had us over for drinks. There property has a river run through it so we sat out there for a while having a few beers. He got a call and his wife was on her way home from work and he had her stop by and pick up a few pizza pies. My foreman is in his mid forties they wife showed up and she was a short blond very pretty and a fat ass in her skin tight jeans. With the foreman and his wife myself there were 4 others. We had beers some food and by 8 most the other guys had to get back home. I’m the only single one and was getting ready to leave when his wife Stacy pulled out a bottle of good tequila and opened it. Down by the river as the sun came down was a beautiful night. She lined up a few more shots and said she was going to go change. My foreman poured 2 more and shot them and lured me one more. I honestly lost count of how many he had before she came back. When Stacy came back she was in flip flops a pair of cut of jeans and a spaghetti strap tank top that covered hardly anything. I was so focused on her ass that i didn’t realize that her tits big like a D cups big. She lured me down by the river where there was a picnic table and sat me down. She sat on the table making her crotch level with my face. I was so close that I could see that she was a true blond some of her public hair was protruding from her shorts. She gave him one more shot and he said women im fucked up. He sat on his chair and she came back and sat on my lap I saw that he just watched her barley keeping his eyes open. I was rock hard she grabbed and tugged at my jeans and finally undid my pants and pulled my cock out. Sitting at the table she just kneeled in front of me and stoked and sucked away. My first shot was quick right down her throat. She did a great job kept her mouth shut and swallowed a few times licked her lips I stood her up yanked her shorts down no panties put her on all 4s on the table and ate her out by the river. I spent extra time shoving my tongue between her ass cheeks rimming her tiny chocolate star. She lulled her big ass apart for me so I could really eat it. I lined up to her meaty lips and pushed in. Damn she was loud grunting and bucking slapped her ass a bunch of times making it bright red right as she started to cum and leak fluid fluid down her legs I shoved my thumb in her ass and thumb fucked her ass while she came. She shook and cried out to not stop I pumped her a few more times hard and she shook again I pulled out lines it up to her ass and slid into her butt. It was so tight I had only had fucked a girl in the ass once before and she hated it. Stacy just relaxed and let it slide on in. I bottomed out and she took a deep breath she fucked me she pulled out then slid back started to pick up the pace and getting really loud. With her hands rubbing away she talked so sorry that I blasted my nut deep inside her ass. She squirts on the picnic table legs shaking she spins around licks the table grabs my coated dick locks it clean leads me to the house we shower fuck again she shows me the spare bedroom says she will be back she’s back in 5 clubs in top of me and rides me like I’m a horse. Woke up the next morning big ass sticking up I claimed up said good morning and shoved my cock in her ass only using spit as lube. It slid back in like nothing I got up a short time later showered again she came in showered and we went and had coffee by the river. We sat having coffee and she was topless and in a g string. She asked if I had anything going on today I asked where my boss was at she said he went fishing with a buddy and I could keep her company until he got back Sunday night. I spent the next 2 days emptying my balls over and over. Since then I hang out her a lot sometimes the boss is here sometimes he is gone. Doesn’t matter I’m her personal boy toy and we fuck a lot. I’m good with it she’s good with it he is happy she found a friend.

1
# 79817 - by Anonymous / June 17, 2025
- True Sex Confessions -
Straight Female / 48

Another Perfect Day

Hi, I'm Beth. I've posted here before about my husband and I and our 23 year old tenant , occasional partner.

Sunday, father's day and so happens, also my birthday. Started the day with a really nice fuck with my husband. We had planned nothing other than just hang around and relax all day. About 10 or so that morning, our tenant knocks on the door with a birthday card for me and a happy father's day wish for my husband. Says he's going golfing with his father and that he was on his way and would be there in half hour or so.

Husband was the one that said it, "maybe later on we could help Beth celebrate her birthday? " we all knew exactly what he meant and I was absolutely in but he said he was going to have dinner with his gf and her family. Bummer, I said.
He said maybe later in the night when he gets back? I looked down and could see his bulging cock in his pants, so without another word, right there in the kitchen, I dropped to my knees and put my face against his bulge. That's all it took. I unzipped him and had his gorgeous young cock in my throat. Hubby went over to the window to look out over the driveway. It didnt take him long. God, 23 yo cum is delicious! As soon as I was done with him, he and hubby switched places. He went to the window and hubby came over, cock in hand, and went to work on him. Mmm. 2 loads in my tummy. Yum.
As soon as he and his father left, I was on my back, legs in the air getting eaten dry by hubby.

Btw, he was back at 9 pm and was over. He and my husband fucked me into the headboard. Full of cum and exhausted, I had the greatest nights sleep I'd had in a while.

1
# 79819 - by Beth / June 17, 2025
- True Sex Confessions -
Straight Female / 36

Didn’t Know What I Was Missing

My late husband and I met in high school and got married not long after we graduated. Our marriage, including our sex life, was wonderful. My husband was the only man I’d ever been with. I never felt that I was missing anything or was unfulfilled.

But after my husband died unexpectedly 2 years ago after 15 years of marriage, I was alone. After a period of grieving, I needed to get out and be social again. My girlfriends were active setting me up with dates. It took a while for intimacy to be part of these relationships.

When I allowed men to be as sexually aggressive as they wanted to be, I learned something very quickly. I had no idea at the time but my late husband’s lovemaking was very sort of quick and I guess somewhat selfish. I don’t say that to be mean. In fairness I was the only woman my husband was with so he did not know any different either. I didn’t know any different at the time, and I still remember him and our lovemaking fondly.

But now I am dating and meeting men who place my sexual needs first. They want ME to have orgasms. They want ME to tremble and moan with pleasure. They treat my body as a temple to be worshipped, not simply an object to use for their pleasure.

My girlfriends now ask why I am not settling down with one man. I tell them, truthfully, because I’m having too much fun. I never knew I enjoyed sex so much because I never had sex like this. I’m enjoying men with big packages and men with expert oral skills and men with wild imaginations and appetites. And even sex partners who are not men (shhhh…my girlfriends don’t know about that). I still miss and love my husband deeply and wish I’d never lost him. But I also love my new sexual freedom and am glad I found it. I’m having so much fun and feel deeply fulfilled…at least sexually.

4
# 79821 - by Theresa / June 17, 2025
- Fetishes and Kinky Sex -
Straight Male / 28

First Orgy

At a party with two other couples we all got pretty high. We all knew each other well and would often flirt with each other. We got together regularly on weekends. This night we were in the living room lying on the carpet listening to music with the lights turned down very low. After an hour or so, I glanced over at my wife just as she held my friend's erection and guided it into her. She moaned as he pushed deep. While we all had made out a little with each other sometimes and had felt each other now and again, none of us had had sex with anyone other than our partners. The four of us watched as my wife and our friend fucked ever more uninhibitedly as the minutes went by. It was sexy to watch her. My wife had broken a barrier and soon the wife of guy with my wife was fucking the other guy. His wife moved to me took me in her mouth and then got on top of me and lowered her wet pussy around my very hard dick. Finally, I heard my wife ask our friend to cum in her and he did. Hearing her moaning with pleasure caused me to cum heavily. Before the night was up, each couple had traded with the other couples. It was incredibly hot and erotic. Amazingly, everybody got off on what had turned into an orgy.

The six of us get together about once a month at one of our homes for a night of fucking each other. We are all straight, so it is straight sex. One of the women always tends to start the evening by beginning with one of the men. Usually, we fuck one on one, until all of the women have fucked all of the guys. Since the women can handle more than the men, two women will sometimes will be with one guy if he is ready. We are all pretty young and have a lot of sexual energy. Sometimes it gets kinky. One night we tied up one of the women and each of the guys fucked her one after the other. The women watched and masturbated while their friend was being pounded. Although not on the same night, each of the women wanted their turn being tied up on subsequent occasions.

Things have further developed because we no longer wait for the group to get together. We are all friends with benefits. Not long ago, I came home to my wife fucking one of our friends. We all feel free to go to each other's homes. I have fucked both of the other wives at their homes. And, the wives have gone to the guys as well. I love watching my wife being fucked. Usually, at the end of the group night, I fuck her when she ifs filled with cum. It's a great feeling.

My wife and I have talked about this strange arrangement, but we both get off on it. So, far no relationships have been disturbed. It is intense casual sex with friends. I think it will stay that way as long as we all live in the same city. People are careful not to hurt any feelings. Usually, one of the guys will call to see if it's ok to come over. Moving for jobs will eventually change things.

1
# 79822 - by Kent / June 17, 2025
- My Spouse -
Straight Male / 43

Big Promotion Promise

My wife has been owned by her boss since way before we met and they were very straightforward and honest about how they would continue their relationship regardless.
In essence, she would be my wife but she would remain his cumslut and fuck toy.
It may be difficult for most folks to understand but she has always had a slutty streak and he's made her into his personal assistant and corporate whore.
He's told us that she's accompanying him on a 3 day overnight business trip next week and he's expecting to sign some major deals.
When he dropped my wife off at home last night he told me there was a very good possibility that my wife would be earning herself another promotion and a good sized pay raise if these deals come to pass.
He also said with a good dose of mockery that "Your wife will be sucking a lot of cock but it will all be worth it. Besides, you and I both know she can never get enough cock."
Embarrassing and true.
My dick does throb a little whenever he talks about my wife like that and when I kiss her I think about all the cock that's been in her mouth and I'm so lucky to have such a hot and nasty woman for my wife.
She has told me in confidence that sometimes in the heat of passion he's said he would like to have her wank him into my mouth so he will own both of us. He hasn't said or done anything yet and I think it was just dirty talk when he was randy.
I never had any gay feelings but I have fantasized about sucking his dick and tasting my wife on his meat stick. She tells me it's about seven inches and very thick.

4
# 79823 - by Charley / June 17, 2025
- My Spouse -
Straight Male / 60

Cum On My Wife's Breast.

Years ago, my wife and I looked into the swinger thing. It never really took off for us but there's one memory I've never been able to shake. We went to a few parties and pretty much just watched. One couple spoke with us about it. They noticed and said they started out just watching then just doing things together so others could watch. The girl talked my wife into blowing me while she blew her husband. We both came, the girls swallowed and it was a thrill because people did watch.

Met them a few more times and we moved on to the me and the husband eating our wives out then getting blown while people watched. It was fun but nothing crazy in that atmosphere. We started fucking in front of each other and other people. The biggest thing for my wife were the few times she masturbated and came while people watched.

We never did any real swapping but we got handy with each other. The guys feeling the wives and the wives feeling the guys. One night my wife was laying back while I ate her pussy. The other guy's wife and my wife were playing with the guy's dick. He lost it quick and shot a huge load across my wife's chest. Thick rope after thick rope. On long thick stream of cum landed right across my wife's right nipple.

After my wife came, I moved up to fuck her, slid in and pumped her while looking right at all that cum on her chest, most especially the thick stream splashed across her nipple. My wife has large, very round breasts with silver dollar nipples. The cum stood out on such a beautiful breast. I'm a breast guy and I love my wife's nipples so it was very exciting seeing this while I fucked her.

Now, almost twenty years later, whenever I move in to suck my wife's right breast, I think of that guy's cum splashed across her nipple, even as I'm sucking. Its like a photograph in my mind. It turns me on and makes me wish my wife had gotten over the hump into more serious swinging.

7
# 79824 - by Cape Gut / June 17, 2025
- My Spouse -
Straight Female / 47

Getting Back Into Giving Bjs

Not all to long ago I hated giving head. I just found it boring and hated the process of doing it. My husband just stopped asking for bjs eventually and just relied on sex or masturbation to get off

Then one day last year around thanksgiving I could see he was stressed so I got on my knees. Opened his pants. Pulled his dick out of his tighty whities and gave him a bj. He cummed quick. I swallowed

From then on I started to give him regular head.

He learned early on that boxers made it easier for me to give him head in certain situations but boxers or tighty whities I don’t care. I’ll get to that dick.

Having recently trimmed his bush it makes it so much better for bjs now

7
# 79809 - by Kayla / June 17, 2025
- Evil Thoughts and Deeds -
Straight Male / 34

This Was The Weekend For It

I’m having a fling with an older women form work. She’s 10 years older married with a pair of kids that are in there late teens. Husband ignores her but keeps her around for who knows what. They argue he accuses her of cheating even before we were hooking up. She’s a sweet good looking tiny framed women. She is the office mom who cares about everyone treats everyone nice and occasionally lets people walk all over her. I struck up a conversation one morning random we had worked for a couple of years and had said maybe 10 things to her.

She came in one Saturday morning in these baby blue leggings and sweatshirt bleach blonde hair in a pony tail. She only 5 foot tall with shoes and these blue leggings hugged her ass and she was sporting a massive camel toe. I mean her pussy lips were swallowing the thin material. Got me aged and I started chatting away. By noon we had made plans to grab lunch. Her husband had no clue where she was she would just text him telling him she was working OT. After a few drinks I had her bent over in the back seat with her blue leggings down below her ass and my face was buried in her rear. Yup I licked her pussy and ass and she got her ass licked for the first time ever. She said it tickled and felt really good. Before she could say to use protection she was grunting away. She had a very large G spot and came almost immediately. I had not come yet and she was 3 deep and working on a 4th. She was great at sex very caring and she kept telling me she could take pain. She spelled it out for me after me not understanding what she was trying to tell me. She looked me in the eyes and said stick it in my butt I did and it felt amazing. When we where done she cleaned up she was a mess she ruined my shirt cleaning up. She made me drive home shirtless but totally worth it. We did this for months lunch time before work after work. She would come late saying overtime. Husband got to accusing her of cheating and we had to slow it down. Never stopped juts slowed it down. Saturday mornings she would just come over instead of work and I’d work her. When she was MIA for hours and the check remained the same is when he caught on. He followed her to work he would show up at lunch. A couple of close calls scrambling to go in to work from the back door. Having to hike her skirt down run in leaving her panties in my car. I’d bring them in later to her. Most of the office knew what was going on just looked the other way. I’d take picture and videos of our encounters. Some where very graphic. I wanted her to come over last Saturday she was worried of getting caught I was tired of waiting she was freaking out thinking I was going to break it off. She started sending me nudes and short clips. She would send them and delete the text strand. I waited for a bit then responded it took a bit but she would respond. I purposely waited a while then text her to send me more. I then got a text back asking who this was. I though about it and responded the person who owns you. Nothing I then though about it some more and I sent her my favorite picture of her. She’s on all 4s I have my cock balls deep in her ass. Her tiny ass is stretched her hair in a pony tail completely naked she is looking back at me eyes looking direct into the camera and there is no hiding who it is. She has the face that she makes right before she cumms. It’s like pure lust clearly visible. The caption i sent with the pic was remember when you told me i own it now. Never responded I waited and waited. A few hours went by and nothing. I then hear the doorbell ring I hear keys in the door and she walks in tears in he eyes first thing she says is she was caught he has the phone and was going through it. She said all our messages except the ones I sent this morning where gone. He went nuts called her every name in the book and finally threw her out. I held her for a while gave her some kisses she wanted to cuddle so we did and soon after we were in bed rolling around and going at it. She ran by the house when she knew no one was home got some things came home fucked. We woke up this morning showered and fucked then drove to work together. She sent me an email to call her at her desk. Her husband wanted to get with her after work to give her phone back. She things he wants her back but her mind is already on moving past him and moving in with me. So it looks like I’m going to get what I wanted after all.

0
# 79798 - by Anonymous / June 16, 2025
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