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:

I Have Been Having An Affair For About A Year Now

I started car pooling with a coworker almost three years ago when my husband and I bought a new house close by where he lives. I have just over an hour of a commute so it just made sense at the time, we were never having an affair up until then. We were heading into work one morning and I had been running way behind because of our daughter so I stuffed my nylons in my purse, grabbed my shoes and other work bag and headed out the door in my slippers.
I get into his vehicle and he is looking at me like I am a mess then sees my slippers and says Oh good you brought shoes. We are backing out of the driveway and I show him my nylons and say Yeah, have to put these on also, he looked over and told me he would try to keep his eyes on the road or something and I laughed saying Yeah, like I am much to look at and the flirting kept going from there.
Minutes after we get on the expressway, I turn right towards him with my feet in his lap and bring one up to start putting my nylons. He started massaging one of my feet with one hand and still driving with the other one, I just melted into the seat telling him that felt really good, he just kept going back and forth on them and I did not care at all. He began climbing my legs, calves, thighs and I gave him a look and spread my legs out best as I could and his fingers began massaging my underwear. I told him to hold on a second, put both feet on the center console, lifted up by butt and took them off then got back into position, his wasted no time getting his fingers on me.
He said we were about ten minutes from our work exit as I was still getting played with and had a few orgasms already just from his fingers playing with me, I was that sexually frustrated from a few years of nothing from my husband. I told him Okay and sat up probably looking like hell for sure as I brought the sun visor down looking in the mirror at myself. I finally got my nylons and shoes on, went to the bathroom as soon as I was in the building and touched up my make up and hair. I looked at myself for a few minutes in the mirror shaking my head then told myself he was getting a blow job on the way home because that was an amazing ride to work this morning.
We were not even a minute on the expressway going home and I leaned over the center console and started undoing his pants, he offered to help and I told him to slide the seat back if he could and keep his hands on the wheel and eyes on the road. He let out a nice moan when my lips sucked his cock out of his pants some more then I felt his hand on my bum caressing it thru my skirt, I swatted it off and told him to drive.
He came shortly after telling me sorry but this was all just very exciting for him, I told him me too and said this morning was just amazing, never did anything like this before and he asked if I wanted to go parking like we were two teens on a date. I asked him if he knew a good place that was private then he brought up phone tracking and asked me if my husband would look at something like that on me. I had not thought about it and told him Yeah, you are probably right, we better not until I find that out. He asked if he could play around with me again, we still had like half an hour for the drive before getting off the expressway, I pulled everything down to my knees and put my feet up on the center console while he ran his fingers down my legs and began caressing me again.
I walked in the house with my underwear clinging to me because of the wetness, hugged my daughter and went upstairs to change, decided a quick shower was probably a good idea and came back down to start dinner.
Turns out my husband had never turned on anything about tracking, took me a few google searches to figure out my phone and nothing was turned on for it. I did not ask him about it and told my coworker a few days later about wanting to stop by this mall and return something, he said he had time and when we pulled in there I told him to park somewhere far out but discreet, he looked at me smiling and asked if it was for what he thought it was. I told him yes and began undressing, he folded down the rear seats without even getting out of the SUV, we crawled back there like teens in heat and have been doing this a few times a month every since along with playing around on the drive to work. Yes I know, I am a bad wife so don't bother telling me about it.

Wife Is Out Of Town For Work

My wife is 42, curvy, very nice “enhanced” boobs. She is out of town this week and I challenged her to get as much strange cock as she can. Day 3 and she has been fucked 4 times. All pickups from the bar at the hotel. Today she might get fucked again, but I am skipping ahead. She called me this morning before she was heading out to meet with a coworker. She was telling me about the guy she fucked last night, it ended up being late before the were done, multiple rounds and he stayed in her room part of the night. I think there were plenty of shots thrown back before she put his cock in her mouth. So we are talking and there was a knock on the door. Hang on, I can hear her talking and laughing. “oh no this is great I have time if you do.” I hear her phone getting moved around. Then muffled voices and sounds. Then my wife, always making sure I am in the fun speaks up. “Mmmmm, am I doing a good job sucking your cock?” Oh my God yes was his reply. Your husband is a lucky man. Then my wife tells him “you think so, I’ll let him know you said that, but your cock is a lot bigger”. I few moments later she asks him to get behind her and fuck her. I heard my wife moaning and the bed bouncing. I heard her cumming. Then she says slightly louder than she needed…”in my mouth,” the response to him telling her he was about to cum. Hearing him groan as he shot his load and my wife letting out a “mmmmmmm, mmmmm wow, that was a lot.”

Some more talking that I didn’t really understand and then my wife telling him. Not at all, if was fun, of course, go. Maybe I’ll see you tonight.

My wife picks up the phone giggling.” I just got fucked, did you hear?” Yes I did was my response, what was that about, was that the guy from last night? “Sort of, this guy was going into his room down the hall as I came out of my room yesterday evening. We said a few words and went about our business. Not long after I saw him at the bar,I told him our deal” so what she told him is , that she can fuck people she finds attractive with permission and I am sure she said “Infind you attractive”. “ he said he was so tired, had been up for 24 hours and probably wouldn’t be too much fun. I joked and said if you get some rest, you know where my room is.” When I recognized him when I opened the door I opened my robe and he pulled out his cock”


Hopefully one more guy Tonight . I asked her to call me and put her phone on the nightstand so I can listen

How My Tuesday Night With My Husband And Girlfriends Went.

My husband has some major fetishes. I do everything I can to please him. His birthday was yesterday and as usual my two besties were more than willing to fulfill his birthday sex scenario to the letter. In the quiet of the bedroom, I, Tina, stand with my wrists bound above my head. My heart pounds in my chest as I look down at my feet, encased in tan pantyhose, and then up at Mike, my tall and handsome husband, his eyes gleaming with a mix of lust and admiration. I'm slightly curvy, my wavy brown hair cascading down my shoulders, and I'm dressed in a simple white blouse and blue jeans. I purposely resist at first, but I can feel the heat building between my legs, the anticipation of what's to come.

Elizabeth and Cathy, both clad in black pantyhose, stand on either side of me. Their hands begin to roam over my body, tracing the curves of my hips and the swell of my breasts. "You're going to love this," Elizabeth whispers in my ear, her breath hot and tantalizing. Cathy's fingers find the hem of my jeans, slowly unbuttoning them and sliding them down my legs, revealing more of my pantyhose. I shiver as the cool air hits my skin, my body already aching with need.

Cathy's hands are on my feet, rubbing and massaging, while Elizabeth's fingers trace the edges of my pantyhose-covered pussy. "You're so wet already," she murmurs, her voice husky with desire. I can't help but moan as they begin to lick and suck at my pussy through the thin fabric, the sensation driving me wild. I can feel the heat building, my body aching for more.

Mike steps closer, his cock already hard and pressing against his pants. He rubs it against my feet, the friction sending shocks of pleasure through me. "You like that, don't you?" he growls, his voice low and commanding. I nod, my breath coming in ragged gasps. He unties my wrists, and I stumble slightly as the blood rushes back to my arms. He guides me to the bed, his hands firm on my hips.

He lays me down gently, his eyes never leaving mine as he positions himself between my legs. He rubs his cock against my pantyhosed feet, the sensation of his hard length making me moan. He leans down, sucking on my toes through the pantyhose, his tongue flicking against the fabric. I can feel the wetness seeping through, the sensation driving me wild.

He moves up, his cock pressing against my pussy, the thin fabric of my pantyhose the only barrier between us. He rips them open and thrusts into me, the sensation of his cock filling me, stretching me, making me cry out in pleasure. He sucks on my toes, his tongue flicking against the fabric, the dual sensation of his cock in my pussy and his mouth on my feet driving me to the edge.

Elizabeth and Cathy, meanwhile, have moved to the side of the bed, their bodies entwined in a 69 position, their pantyhosed pussies grinding against each others mouths. Their moans fill the room, their bodies writhing in pleasure. The sight of them, combined with the sensation of Mike's cock in my pussy and his mouth on my feet, pushes me over the edge. I come hard, my pussy clenching around Mike's cock.

Mike pulls out of me, his cock glistening with my juices. He strokes himself, his eyes locked on my pantyhosed feet. He comes hard, his cum spraying onto my feet, the warm liquid seeping through the fabric. Elizabeth and Cathy, sensing the moment, move to my feet, their tongues licking and sucking at Mike's cum, their moans of pleasure filling the room.

Mike collapses onto the bed next to me, his body slick with sweat. "Fuck, that was amazing," he says, his voice breathless. I can't help but smile, my body still tingling with pleasure. "You're a dirty little slut," he whispers, his voice low and husky. "And I love it." I laugh, my body still shaking with the aftershocks of my orgasm. "I'm glad you do but you better get hard again because my besties need cock too.”

My Alone Time

This started about five years ago. I’ve been married for quite a long time but as I got older, his sexual drive decreased and mine increased. So I started using my vibrator more and then I noticed that if I watch porn that it will make me even more horny. I would just have long sessions in the shower or pleasure myself when he was at work throughout the day. But to make it a little more interesting I would change a few things up. I would start using my vibrator and walk in front of the windows. At night when he was not home yet, I would use the vibrator in the backyard.

One day, I was stuck in traffic for quite a long time and was looking at my phone and decided to look at a little bit of porn. I got so turned on. I put my hands under my dress and played with myself. There were men in trucks and vehicles all around me and the thought of them, made me so turned on.
Now I am totally hooked on playing with myself in the car. Some of my most intense orgasms have been in the car now. Every now and then I kind of think a man in another car knows what’s going on. I’ve never really thought much about being with another man throughout my marriage until recently.
Probably what was the hottest time that I’ve ever had is that I went by and got some fast food one day and went to the park and sat in my car and ate it. After I was done, I just sat there and enjoyed the park, but I noticed that there were some young men playing basketball a little ways away for me. (Yes they were young men). I actually drove a little closer and parked near where they were playing. Most of them were playing in just shorts. I couldn’t help myself, but I started playing with myself, and I had one of the biggest orgasms that I have ever had. I have gone back to the park several times.

College Friend Weekend

Here is my confession, just as it happened. I have always considered myself straight, but as I've gotten older I am now sure I am bi. Last holiday I went to visit my closest friend and her husband for a long weekend. I have know this lady since we roomed together in college which is nearly 20 years, and her husband for the past 10. We get together often, but I have never admitted this to my friend, but since college I have really been attracted to her. She is extremely smart but also so much fun to be around. Her husband is equally fun and one of the nicest people I have ever met. I've been through 2 marriages but my friend has been with her husband since they married years ago.
During this visit we had planned to visit a mountain hot spring.
None of them had been there but she had made a reservation for one of the cabins so we could enjoy an afternoon of the hot springs and stay without driving out of the mountains until the next afternoon. We arrived and were surprised to find that the entire resort was nudist if one wanted to be, most everyone was nude and not just in the hotsprings, and there were different areas that you could stay. There were camping spots, as well as car camping spots and 2 different size cabins you could rent for the night. Because of the popularity of this place all my friend could secure was the smallest cabin. We had two full sized beds but used our sleeping bags on top, We quickly unpacked and had a small dinner from the cooler we brought. The three of us then decided to try the medium spring and relax.
We got to the spring and my friend started to take off her clothes, she and her husband had read about things there and knew it was clothing optional. I had my bikini on under my shorts and t-shirt. I hadn't seen my beautiful friend nude since we were young college kids, but I think she looked even better than she did then. She has to follow a restrictive diet for health reasons so she was still thin, and still had her large breasts. I had always admired her small frame and large nipped breasts. I was trying not to stare but I watched her pull her top over her head revealing her full soft breasts stuffed into a pretty bra. She then slid her hiking shorts down showing a matching navy thong. Her skinny little butt was still a turn on for me. Finally she undid her bra and let her heavy breasts down, and looked so sexy as she bent down sliding off her thong revealing her jet black landing strip pussy. I was so turned on watching this that I hadn't hardly taken anything off myself. Doing as my friends did, I took off all my clothes, bikini included, and felt the cool mountain air on my body.
As we sat there chatting and watching the sun go down, my friend would occasionally get out of the water to sit on the edge of the hot spring to cool off. Each time she did so, I was eye level with her pussy and beautiful fat lips which would gap open as she would pull one knee to her chest. I was so turned on that I had to rub myself as I looked at her swollen pussy lips as she sat there. I also watched her in the moonlight when she sat on the edge, watching her nipples harden in the coolness and loving her large light colored areolas looked, and the way her nipples were so dark against them when they would get hard! I nearly had an orgasm right there watching her sexy body.
It eventually got dark and late so we retired to the small cabin. I laid on my bed just a few feet from my friend and husband. We were all pretty tired from a bit of a drive and the relaxing warm spring water. I quickly drifted off to sleep. I'm not sure how long I was out, but I woke up slightly, maybe because of the altitude, but as I laid there drifting back to sleep, I heard the sleeping bag that my friends were in quietly rustling. I could tell by the cadence of the rustling that they were having sex, and I listened to my sexy friend quietly moaning and panting as she was being ridden. This went on for a good ten minutes when I heard the moments getting faster and more loud, despite their efforts to be quiet. I looked through the darkness of the room and could see the form of my friend riding on top of her husband. She finally sat up and I could see she was completely nude again, and her nipples were totally erect as she rocked back and forth on her cute hubby. She became more frantic and suddenly collapsed and fell down against him, after an obvious orgasm.
I will remember this experience for a long long time. I was really turned on by both of them and especially by seeing my friend's orgasm. I have to confess, I so badly want to have a threesome with them but cant figure out how to ask without risking my good friendship with them

Amazing Weekend

My wifes weekend a month ago.

Saturday morning I woke up to my wife sucking on my cock.

She paused to let me know she was horny, but then when wasn't she.

Unfortunately as I was seriously enjoying the blow job, the food delivery van arrived.

An hour later I had to go out to collect some materials for a contract on Monday and dropped my wife off at the park.

She told me when I got back home, she'd met Pete on her run. They'd gone into the woods at the far end of the park and he'd fucked her after she'd sucked on his dick.

I wanted to indulge myself but my wife said she'd arranged to meet Mike that evening, so Id have to wait.

Mike's being fucking my wife for years, even before I met her, so once a week they meet up for sex. His cock is huge but he never lasts long, so I said Id drive her.

They fucked in the back of my car as it was raining. I watched with a raging hard on, desperate to have my fix, but again I was told to wait.

At home she had me lay on the rug then straddled my face and finally I got to enjoy her creamy cum filled c**t.

She knows its my fetish and makes sure I get my fix at least once a week.

She must have orgasmed half a dozen times before she lifted up and told me "Tomorrow night".

Sunday morning we both went river swimming. It's something we both love to do to keep fit. There's a club we've joined and the organiser John is someone my wife keeps happy by sucking him off. That Sunday morning however after everyone else had gone, he fucked her in his little shed by the river. I waited in my car but could hear them fucking.

Before our evening meal that Sunday we took a shower together and it was then after a whole weekend of her having other mens cocks in her, I got to fuck my wifes beautiful arsehole and cum deep inside of her.

Is This Really Cheating

So me and my husband has roleplayed all kinds of scenarios, out on my bike country lane, chain come off right by wooded secluded area, guy helps and I help him by showing my tits off, bending down showing my tiny knickers, or being taken to someone's house where my husband has previously arranged a Facebook Marketplace purchase only for a big cocked fucker to be their and my husband encourages me to suck the gentleman for a discount.

As I said we have played around with this and exhausted it to death, so something had to give and this is what happened.

We went away up North, rented a cottage not far from my sisters house, they have kids so it was great, lovely area to play lovely weather.

We over at my sisters house, when her husband who I grew up with and was one of the only locals who never shagged me, said that Ross was back at his mums, as his mum had a fall, and Ross and his brother Dale are doing the house up to sale as mum is moving in with him. Brother in law teased that I used to go out with Ross didn't I, I said "we just knocked around a bit, " is that what they call it those days.

Anyway I told Ross you were back up, and he said "if we want bring her over and we can put her to work, that girl had such energy and so generous "
I was mortified said I am going back in, and said they shouldn't believe everything they hear.

Shall I tell my husband after I go In case he tries to talk me out of it.

I Want My Best Friends Husband

Gossiping with my best friend I found I was always complaining about my husbands lack of sex drive, laziness, or just him being an asshole. I asked her why she never complained about her husband and she said she doesn't have anything to complain about. He's got the sex drive of a teenage boy, a big dick, knows how to pleasure a woman, takes care of her, works hard and stays in great shape. I was curious so asked how big his dick was and she showed me pictures of him. It was like an arm. At least 6-7 inches long and thicker than any dick I've ever seen. I've been joking with her that she should share him, maybe give him a threesome for his birthday, or for my birthday! Now every time I see him with his big muscular chest and arms I just dream of his big dick inside of me. If I ever got the chance I'd fuck him behind her back, but I think it'd be better if she just let me have some fun with them from time to time. I just wish I knew how to convince her that it would be fun to let her husband fuck my brains out.

I Let My Girlfriend Lose Her Virginity To Someone Else

A while ago I started dating a girl who was a complete virgin. I was her first boyfriend. She was just discovering things with me. But there was a big problem: my dick is too small. She was always curious about having sex with me, but I was always reluctant because of my size. Time went by and she wanted to have her first time and I always tried to satisfy her with oral sex, which worked to a certain extent. She loved it when I sucked her pussy and played with her when we could get caught. But it wasn't enough anymore.

One time we ended up traveling to the beach and we had a mutual friend who she seemed to have a certain interest in. In the first few days she seemed to be more excited than usual, especially when she was around this friend of ours. At night we would have oral sex and she would tell me she wanted me to fuck her, but I could never go any further. She was unsatisfied, saying she wanted to have her first time. Deep down I was horny and ended up asking her if she would like a man like our friend to fuck her.

She was reluctant at first, but I could tell she was really turned on by the idea. I started jerking off while we were talking and she confessed that she would like to fuck him, if that was the case, after all, she was dying to have her first time. I told her that I would accept her having her first time with someone else, as long as she was satisfied with it. She was reluctant, but I insisted and told her to make plans for her to go to his room the next day and go after him, without confessing that we had made plans, while I would watch from behind the door.

The next day, we spent the day normally until it got dark and I was nervous. When it got close to dawn, she kissed me and said she was going to his room. I could tell she was in the mood, wearing a T-shirt, no bra underneath and leopard-print panties. I remember it very well. I waited in my room, anxious to see what was going on between the two of them. After 15 minutes I ended up going towards the room where he was, being careful not to make any noise. In the hallway, I could already hear the sound of the bed moving, and I felt a mix of jealousy and arousal. The door was half open and I started to watch them from afar.

I was surprised by the scene I was seeing. My girlfriend, so innocent, kissing another guy so intensely. He was shirtless, in his underwear while she was still dressed, sitting on top of him, kissing him while they rubbed against each other. It didn't take long for him to take off her shirt and suck her breasts. I could see her moaning from afar, crazy with desire. He laid her down next to him and started to take off his underwear and I soon saw that his dick was hard and big. My heart raced and I wondered if I should intervene before things happened. My girlfriend, lying next to him, started to grab his dick and jerk off, without any shame. Her firm hand, holding another dick, drove me crazy. At that moment I started jerking off too.

It wasn't long before I saw her sucking his cock, licking it as if she had never sucked a cock before, while he moaned with pleasure. She had barely sucked mine, I hardly ever let anyone be embarrassed. Seeing her like that made me cum and I ended up wiping my cum on my underwear. She got up and took off her panties, which were probably soaked. I couldn't believe she was really going to lose her virginity to another guy. She got on top of him, while he was lying down, and started to sit on his cock. Without any protection. At that moment I went crazy. I was watching my girlfriend, innocent and sweet, sitting on another guy's cock, who was taking advantage of the situation, fucking a virgin girl without knowing it was his first. I realized she was totally in ecstasy, moaning shamelessly, sitting on his cock with desire. My cock hardened again and I started to jerk off again. I had never seen her having so much pleasure as in that moment.

They changed positions and he got her on all fours, while he fucked her hard. She was moaning with pleasure and was probably having an orgasm. He was slapping her ass while he fucked her. He was completely dominating her. At that moment I came again and my underwear was completely wet. It wasn't long before he ended up cumming, I didn't see where, but probably in her ass. I ran back to the room where I was and waited for her to come back. I had just witnessed my girlfriend lose her virginity to another guy. Something indescribable that happened to me.

Two Older Guys While In College

Most girls my age in college were waiting to experience guys our age or college sex parties if you were into that. But not me.

I was 200 miles from home when attending college. I turned 18 a week before moving into my dorm. For me that meant I was old enough to finally explore things.

I lost my virginity my first week in college to a guy my age who also was a virgin. The set was great. He was a great guy but I oddly had a thing for older guys.

A few months went by and I met a 66 year old one weekend. It took a month before I had him in bed in just his tighty whities as I was on top of him in my shirt and panties kissing him. I had only had sex once before and I told him I was nervous. I pulled his tighty whities off and he had a very nice hairy dick. I did my best to suck it .

He eventually has me lay down. He pulled my shirt off. Then my bra. He kissed my body down to my panties and pulled them off. My shaved pussy was exposed as he started to lick it. It was my first time receiving oral and it felt so amazing.

As he fucked me I had a mind blowing orgasm. He cummed in my pussy. Then only after he cummed did he think to ask if I was on the pill lol. I was and told him you’re fine. We had sex regular from then on. A few times a week. I loved every second of it. I was very turned on that he was 66. Then one day after sex as we are getting dressed he said I typically never would ask this but are you wanting more guys? I told him well I do want a college slut phase and I’m currently working on it obviously.

He proceeded to tell me his one friend who is 65 is single and lives alone too could use some sex I’m his life. So I said I’d gladly help him out.

A couple days later I’m at the 65 year olds house. We are both stripped to our underwear. Him in tighty whities and I was in black bikini panties. I can remember him pulling my panties off first and then he pulled his tighty whities off. A hairy dick like the other guy only his was thicker. I was pretty shocked but boy was I wet. I got on top and began to ride him. He told me he hasn’t been in pussy in years. And said he never had younger pussy.

I rode him until he cummed in me.

From then on I had sex with those too guys my whole time in college.