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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:

- Evil Thoughts and Deeds -
Straight Male / 19

Why I Stayed Close To Home

I stayed at my local JC then state school because of my neighbor. I’m 6 foot 4 now 225 lbs work out freak and black. While I don’t have a 12” cock I am a very thick solid 8 and a half inches. But thick. My neighbor is a white married mother of 2 Suzy home maker type. She is an English teacher and when I was 17 she and my mom decided to have her tutor me. She’s in her early forties short dirty blond hair b cups which she tries to make look bigger she has nice big nipples though big thick thighs and a nice round fat ass. Jeans short ass shorts she shows ass cheek. Especially now that she accepted the fact that she likes BBC. It started shortly after I turned 17 going into my senior year summer before. Mom asked her to tutor me. I’d go with her during the day when my parents were at work and she would work on writing and help me on what i needed. I always liked her and being hormonal and horny I wore no underwear and basketball shorts. I’d rub my self cock and watch her eyes. She was very sweet and never said anything. I’d start to rub my cock then I started putting my hands in her legs she tried to move them but I’d just put them back eventually letting rest them there. Soon enough i started sliding my hands up on those thick thighs never moved them after a few days of this I’d rub myself rub her thighs then put her hand on my cock she pulled it away and said not a good idea. I grabbed her hand and put it on my cock and held her hand there and said it feels good though. I’d then force her hand to jack it over my basketball shorts. This went on for a couple of days. This happened over the first 2 weeks of summer starting. Her kids where at camp for the summer her husband commuted. I’d ask if she liked how it felt and I’d ask until she would answer quickly and quietly yes. Finally I started to pull it out and put her hand on it. Her white hand looked small when she held my cock. She looked at it forgetting why I was there to start. Her fingers wouldn’t touch when she gripped the thickest part of my shaft. I pushed her head down and she had her lips to it. I could feel her warm breath on my tip then I felt the tip of her tongue on it then she opened wide and sucked it. She had a huge mouth and she got it in her mouth. I was sitting at her dining room table and she was sitting on her knees in front of me. I told her she was going to love how it felt going in. I stood her up in front of me spun her around and had her pull her jeans off. Tiny G string was left in and I had her get on all 4s ass in the air on the couch. I leaned in kissed her neck and slipped it in. A loud moan and a stop I didn’t listen and slid in slow and kept kissing her neck. Fuck fuck until I hit the bottom then pulled out fast and slammed into her over and over. This English teacher was using language she never thought she was ever going to use. After a solid 5 minutes she screamed some more legs shook and squirted all over us. I pulled out and went down ate her pussy and licked her ass. Still the dirty talking begged me to make it happen again. It was the start of a beautiful relationship. She gave me her virgin ass a 43 year old milf who had never had her ass cherry popped was now taking almost 9 inches of cock in her ass and having orgasms from rough anal. Her outfits went from mom outfits to cut off home made denim shorts that covered nothing she wore the seas often for me. Even when I took her out to eat during the day. We would go to the other side of town and she’d wear these booty shorts and a skin tight tank top showing off her ass and nipples along the way and topping the outfit off with red heels. I liked the look she turned heads walking hand in hand in a shady part of town she called herself my property. She lives 2 lives i stayed close to home because of this nice pieces of ass and it’s been very well worth it. She has no remorse as I fuck her into an orgasm she tells me over and over how much she loves me and I tell her it back. When she hears it from me she picks up the intensity. I won’t share her but I let my close friends watch videos of us fucking. Mostly just he on all 4s talking a mess while anal or I’m destroying her pussy. Big age difference but she’s completely convinced she can make it work one clip she tells me while I’m balls deep that she can hardly feel anything when her husband fucks her. 2 pump is what we call him lol

1
# 79890 - by Anonymous / June 20, 2025
- True Sex Confessions -
Straight Male / 59

Daughters Friend

Recently as drove up to a local pub where I'm the resident DJ, I noticed this woman standing at the door as I parked up, I noticed her more than I would normally, because she was wearing a short black dress ( an off the shoulder number ) and her legs were bare, and she was wearing high heels, and I thought to myself ' Hell yeah I wouldn't mind spending the night between the sheets with her, being a widower I don't see any harm in thinking things like this, when I see a woman I quite fancy.

She wasn't at the pub door when I went in, and I went to the DJ booth, once I was there though, I discovered that she was in plain sight diagonally across from the DJ booth, and I had unlimited viewing of her sexy legs, it was a wee bit unnerving, because she kept looking at me, this continued all night even when she was up dancing.

Towards the end of the night, she came up to the DJ booth and smiled and said to me ' you don't recognize me do you ? I looked at her but no I didn't recognize her at all, she said to me I went to school with Jill your daughter, don't you remember me ? would you believe I'm a grandmother ? I suddenly remembered her, I hadn't seen her for a good few years because she moved away with her mum and dad from the area. I was a bit red faced because the thoughts that were going through my head at the sight of this 41 year old woman were carnal to say the least.

She said to me do you like my legs, cos you've been looking at them most of the night, I just said ' guilty as charged ' and she laughed and just turned away. When the pub was closed at the end of the night, I went to my car, and there was Cath standing beside it, and I just said hello you, she replied I cant get a taxi, I found out later that this true and not a rouse, so I decided to give her a lift, and off we went to where she lives, on the way she told me that she was divorced, and that her ex ended up in the jail because of domestic violence perpetrated on her.

I said to her I hope he rots in there, she asked me if I had managed to settle down since my wife passed ? I said no and that I was still footloose and fancy free, this seemed to lift her a bit, when we got to hers, she just blurted out I know you fancy me, what you don't know is I've always had a thing for you even though your Jill's dad, in fact because you've been ' ogling me all night ' I'm really quite horny, so if your not in a rush.

I didn't need a second invitation, sure she was 18 years younger than me, but she was a mature woman, so we walked up to her house hand in hand, when we got in she just took me right upstairs to her room, where she just stripped off, I was naked in no time, dick hard as a rock, she just laid on the bed and parted her sexy thighs, said to me no foreplay needed as I'm soaking, so I mounted her, to be honest I nearly came when I first entered her, but I managed to hold back, but not for long, she said to me I'm on the ' rod ' ( the contraceptive implant ) so no need to withdraw, and I didn't I rode her hard and shot a very large load deep into her, I humped her another two times, and I ended up staying the night as I have no ties at home.

I've stayed over twice and she has stayed over at mine, all I know is that she is one sexy lass and she loves cock, where is this going ? To be honest I just don't know, but I'm not going to lose sleep over it, I'm just 'surfin the wave' as it seems at the moment.

1
# 79877 - by Tiger T / June 19, 2025
- Funny As Fuck -
Straight Male / 41

She Barely Made It Back

My neighbor and I have been getting together for almost a year. I’m in my 40s single In great shape semi retired. I started a business very young it did well so well that it was purchased form me for a hefty chin of change. I stayed on as an advisor so I work 7 days a month. Those 7 days I work with there marketing team and spend a few days in the large city a few hours away. 2 years ago a young couple moved in next door. They where in there late twenties. Mike and Kristina I was surprised that they could swing the price of the house. He is a firemen and she stays at home and is trying to find a career. When you ask Kristina it’s her way of saying she does not really want to work. She is very low key low maintenance which is good for him I guess. Kristina is a short thick brunette hair kind of curly to her shoulders round face nice lips she has a B cup and would like bigger tits but I tell her they would make her look frumpy unless she wore skinny tight clothes or walked around naked. What she does have that I like is a nice round ass some thick thighs a tiny waist. During Covid I had a fit no one was allowed in the gyms so I converted 2 empty rooms in my house into one big room and made a gym. When Mike and Kristina moved in they toured my home and saw what I had done and where amazed. I told them they could use anytime and she took me up on it. It took about 8 months after a lot of flirting and she finally caved one morning after she worked out with me. She went from a shy good wife to a pure slut in that time. After the first day it was on. She even has clothes here to change into in case anything ever happened. Most of the time she is topless and in a tiny skirt or panties. I like to expose her I’ve had a few deliveries made and I have had Kristina in the back yard sunbathing by the pool. She knows so she lays where she can be easily seen with her legs spread open small tits out. Shit like that which gets me off. I joked one time that I was going to let the next guy that came to the door taste her. She got a little nervous and said if I really wanted that she would be ok with it. I didn’t share her I told her I was joking but I did fuck the lights out of her that day. The one day I’m writing about happened a few weeks ago. Mike her husband works a few days then is off a few days. She had mentioned that the way they where able to purchase this home as because his grandfather has passed and had left him a chunk of change. They laid bills off and put down a rather large down payment. His grandfather would be visiting in a few weeks to see the house. Apparently they don’t talk because it was a day he was supposed to be working and we where in my back yard. To be honest Kristina was in a g string I was balls deep in her ass pounding away when Kristina said I heard his truck. I was almost done and she heard the truck pull up I shot my load half in her ass the other on her ass cheeks and thighs. It was a mess. She grabbed her shirt that was on the lounge and she squeezed through the fence where we had moved some boards. I heard a splash then I heard her get out of the pool and about a minute later she was in a robe drying off when I heard a voice ask what was she up to. I had locked my house up making it look as if i was not home. I sat there quietly and listened to how fast she came up with answers. She was doing her laps she was goin to shower. The house is always picked up she is a neat freak. He says that his grandmother should be there in about an hour. She said that’s right and they went in talking. A few hours later she came over telling me that the next few days she would have to sneak over since they have her there for a few days. I told her not to push it take it easy don’t want to get caught. Her response was but I need it. We fucked and I sent her home. The next few days where quickies I even met her down the street when she ran errands. Soon as she left she spent the day here and said her plan was to have a cock in her all day. It was damn close to all day as well. She has been acting funny lately and she said that she is late. Not sure if it’s mine or his. Il update later

0
# 79863 - by Gino / June 19, 2025
- My Spouse -
Straight Male / 47

So My Wife Likes Pussy

After almost 25 years of marriage, my wife revealed she is bisexual and wants to enjoy time with women. I was shocked and surprised, but not offended or hurt. We are pretty open and honest sexually about what we need. I just didn’t expect this.

She now gets together with two friends, once a week each. When she comes home and we kiss, her mouth smells like pussy and I can tell her pussy has been taking a dildo. But she’s happy and honestly our relationship is good.

She doesn’t need orgasms from me like she used to. And she is still open to my sexual advances. There are times when she comes home sexually satisfied but knows I need it and she just lays on the bed, opens her legs wide to reveal her red swollen pussy, and just says “Go for it”! And believe me I do. Sometimes she will drop to her knees and say “I was just eating pussy with this mouth” and proceed to blow me to completion.

So far I have not asked to join and she has not invited. Could be fun, but honestly we are both happy, so why mess with it.

4
# 79864 - by Beau / June 19, 2025
- If The Boss Only Knew -
Straight Male / 37

Getting Ahead From Behind

My sexy wife has been the company whore for a little over a year and between the sex and the bucks, it's a win win situation.
She's always been very into oral, giving even more than receiving. She just loves to suck cock. Loves feeling them get hard in her mouth. Loves being used and degraded. Makes her pussy gush to be treated like a fuck doll.
I have a very strong cuckold fetish and love to imagine my wife on her knees with a handful of randy throbbing juicy cocks waiting for her throat to take their loads. She always swallows too and it makes me so hot when she comes home and kisses me and tells me she's walking around with x number of loads in her tummy. Her cock scented kisses and her creampies are delicious and satisfying.
Her boss is hinting hard that he's going to fuck her ass, if in fact he hasn't already done it.
She told me that I'll never fuck her butt and that it belongs to her boss and his associates.
I'm hard right now thinking about soothing her raw red asshole with my tongue and drinking her chocolate milk shake.

3
# 79867 - by Charley / June 19, 2025
- True Sex Confessions -
Straight Female / 30

Hotel Bar Times Three

I had been on the road for weeks. Finally, no work tomorrow nor the next day. I headed to the hotel bar for dinner, a drink or two and maybe, just maybe a man to take back to my room.

Dinner - check

Two drinks - check check

A man to take back my room - check, check and check

Farley, Zeke and Lincoln sent me a drink. I sent them a few smiles. A few minutes later, knowing what I may be getting into, I wave them over. Small talk, then big talk, then an invitation to join them.

I wasn’t in the room two minutes and I was naked. Six hands all over my naked body. My drenched pussy boiling like mad. On my knees I went, with just a push on my shoulder. One, two and three dicks for me. Three get hard suckings and a drag to the couch. I rode one. I sucked another. The last one plowed my asshole. I was fucked like I needed to be fucked. Three dicks for three holes. When they were done with me for the night, we all took a shower together.

For the next two days I was a toy for these men. If they wanted it, they got it. They wanted everything. They got everything. I never knew I had this in me. I was naked for basically two days, on call for the next hard dick.

5
# 79876 - by Chelsea / June 19, 2025
- Anything Goes -
Straight Female / 41

Husband To Watch, Hopefully.

Second meeting today and he fucked my brains out.
I'm no longer interested in having relationships at my age, and I'm happy living with my impotent husband.
So I just need fucking a couple of times a week (More if I'm lucky).
Used to have a young guy (26) at work who'd fuck me during our lunch hours, or after work. Unfortunately, because he was a great fuck, he moved to Spain with his girlfriend.
A fortnight ago I met a guy at my local park when I was jogging. I caught him checking out my backside as I ran by and it turned me on.
Instead of carrying on past however, I stopped and said Hi. We chatted and he'd not long broke up with his wife.
Letting him know I found him attractive, he told me he thought I was gorgeous and had a really nice bum.
It was like Id known him for years as I eventually let on I loved anal.
Swapping numbers with the guy, I told my husband yesterday what I was doing, and that was meeting a younger guy hopefully for sex.
My husband response was to drive me to his flat earlier today and wait outside for over an hour as I had mouth pussy and arsehole well and truly fucked.
I told him my husband was outside waiting which freaked him a little at first, that was until I took his cock out and began giving him a blow job.
Once he'd gotten the message I really wanted sex with him and my husband was only outside to make sure I was ok, he really went to town tonguing my pussy and arsehole, then fucking me until I was literally all orgasmed out.
We've arranged to have sex again on Friday afternoon, only I've invited him to our home.
My husband said he'll go to the pub down the lane from our house. I was hoping he might like to watch. We'll see.

5
# 79857 - by Louise / June 18, 2025
- My Cheating Heart -
Straight Female / 39

Stepping Out On My Husband, With A Married Man And A Mistress

I'm a manager at a boutique CPA firm. I attended a conference as a speaker. A man in the audience thanked me for my presentation. Later that evening I ran into him at the bar before dinner. We talked shop and the subject came up of trying to find younger staff who wanted to work and not lead off with the quality of life question. He agreed with me and offered a female who had worked for him, she took off some time for maternity leave and wanted to get her career going.

He offered me dinner and we ended up splitting the sheets. I knew he was married and he knew I was married. In the afterglow he tells me this girl has his baby. So he cheated on his wife with a subordinate, cheated on his wife that night with me. He broke my resistance and had sex with me a second time and spent the night in my hotel room.

He had his girl call me, she was impressive. I interviewed her and hired her. I had to adjust the hours so she could work around child care. After I hired her he called to thank me, and I ended up at dinner with him. I lost my compass and ended up under him again at a nearby hotel room. I find out he's still having sex with her.

It's impossible because he told her he was having sex with me. That resulted in sharing our individual sexual experiences. Several months went by, he continued seeing me, and keeping her satisfied. We never discussed his wife and I never discussed my husband. I spent a lot of time with her, and met her baby. At one point she asked me if I was planning on getting pregnant for him.

Where we are now, I am still seeing him. She's asking permission to get pregnant again, as if it's my decision. I'm overly careful, the last thing I need is an unwanted pregnancy. I've slipped up already, mentioning him to my husband. I do not want to meet his wife, but he's more and more insistent. According to his baby mama, his wife knows all about her.

Getting back to the core issue, this girl is a very good worker, better than most. He trained her and it shows with her work ethic.

4
# 79855 - by Jill / June 18, 2025
- Fetishes and Kinky Sex -
Straight Male / 36

Taking Care Of Her

I had a summer intern 2 years ago that turned out to be quite the experience. Kendall is a dirty blond tall ex volleyball player. She’s 6 foot 1 long legs long hair kind of curvy maybe 140 lbs. small B cup tits and this round right ass. Very cute blue eyes that when looking at you have this begging for cock look. I was instantly enamored with her. She has a great personality manage to flirt and get business done. She had stared at the begging of summer watching her walk around in her skin tight jeans or very short skirts. Often wearing a thin loose top and very noticeable bra missing. Later I would learn that she did this because she likes the fabric to rub her nipples making her dripping wet. I learned a lot from that girl who was 22 at the time. At a company 4th of July picnic she put together I met her then BF. A goofy fucker that certainly didn’t deserve her. It was BYOB because out being a company sponsored event we did not supply booze. The employees could bring their own booze and did so. Plenty to go around I had a few beers and a couple of shots over the course of the event. Kendal did as well a little more then expected. Of course the guys feeding her the booze where shop guys who had other ideas on why to booze her up. I had her help me start to clean up it was my way of making sure I could keel an eye out for her. Her bf was just about passed out they had made friends with him earlier and he was done. Kendall was very flirty and chatty. She had on this summer dress that came down above the knee. If she bent over to far she was going to give a show. Most girls that wear a skirt this shirt often will wear legging under the dress. My ex did this often. Kendall leaned over to pick single bagged chips that had fell all over the place and she bet at the hips facing away from me. As she did so her dress lifted up and gave me a clear view of her thong. Nice baby blue thong. I couldn’t help that no one else was paying attention and I took some pics for myself. She stood up her hair was a was and I walked over and fixed it for her. It was the closest we had ever been to each other. She leaned in and I kissed her. Not a peck but a hard rough forced kiss. She kissed back and we did this i quickly pulled away she said don’t stop I had my hands up her skirt playing with her ass as we kissed. I took her by the hand over to the parking lot. It was away from the party and a few cars had left but most people where still at the picnic. I opened my trucks door that hid us as I was parked facing the park and behind my truck was dense trees. I spun Kendal around pulled her skirt up and slid into her snatch. It was warm wt and and tight very tight. She asked me to slow down so she could get used to the size I did not such thing and gave it to her harder. All she said was damn ok then and started making loud grunting noises. What I found I really like about Kendall was grabbing her waist and seeing her round heart shaped bubble butt slam into me. She was soft she smelled good and my hands gripping her waist and forcefully making her slam into me. She leaked her juices all over me a few times before I filled her up. She asked that I pull out but I again didn’t listen and made sure before I was done she orgasmed one more time for me. What got me going and put me over was she demanded that I fuck her firm behind she got up spun around lifted her dress over her ass rested her head on my driver’s seat and spread her legs. I took the opportunity to lick her pussy and ass. Very salty she let out a rather loud OH SHIT keep licking and I did. I went back in and as I pounded her i also fingered her ass. She told me her ass was a virgin. I took that from her later that evening. Her BF was left there at the picnic he drove them she left with me. We left the party I took her to my place and took her anal virginity. It was a mess she cried a bit but didn’t quit. It’s been 3 years since that event. Kendall gave birth to our baby boy she no longer works here she just stops by my office to let me relax and release stress. I really release stress into her lots of stress. As a matter of fact she came to my office yesterday in a very short skirt and let me out my hands around her waist and released about a gallon of stress. She now cleans my cock clean after releasing stress. We are working on baby number 2. Her libido was crazy high when we had the first baby. I have a fetish now for pregnant lactating women. When she comes she literally has a stream shoot out of her tits. So fucking hot

1
# 79845 - by Brent / June 18, 2025
- Embarrassing Moments -
Straight Female / 41

I’m Pretty Sure I Was Tricked

About three weeks ago I was home on a Saturday. My husband had gone golfing with his friends and my son was out of town. One of my son’s friends came by looking for my son and when he wasn’t here we started chatting. I’ve always thought he was very handsome and it became obvious he was flirting with me. I was flattered since he’s half my age so when he leaned over and kissed me I didn’t resist. He told me he had always had a crush on me and I fell for his advances. He came right out telling me he would love to have sex with me and that he had a condom. We ended up going to my bedroom having amazing sex and I kept reminding him not to lose the condom because I wasn’t on birth control. Now I’m thinking he may have done something to the condom because I’m almost a week late and no signs my period is coming.

3
# 79833 - by Aren / June 17, 2025
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