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:

Trying Something New

Our usual swinging couple invited us over and the wife told me she wanted to have us over and try something new we hadn't done before. We could only guess what it was. After the usual conversations about life and current goings on, I finally asked what their plan was. The wife smiled and pulled out a strap on and smiled. I asked if she was wanting to go to our usual room and she giggled and said it wasn't for me. She went and sat by my wife and started rubbing her leg and kissing her neck. Before I could even respond I felt her husbands hand on my crotch and his other rubbing my neck. It wasn't long before he was going down on my and I was watching my wife and his blowing the strap on to tease us. Before long I saw what they wanted. My wife was riding the strap on while she played with herself and watched me get a blowjob. It always turned her on to watch me get pleased and she must have said it was very hot to watch another man do it to me. I knew what would make her even more turned on and before I came I told him I wanted his. We traded oral for a bit, the whole time watching my wife get fucked by his wife.

Before we finished I moved us over to where his wife was fucking mine and watched her take a dildo in her pussy while she went between our cocks with her mouth and hands. She was in heaven. Before long she had us both cumming on her face and tits before getting her own orgasm. Not wanting to be rude she then put it on and fucked his wife to an orgasm while she sucked her husband and I to another cum shot.

My Wife Surprised Me With Her Friends

So the wife and I were having a fucking weekend...no holes barred...wife wearing a strap-on...both naked...anytime, anywhere, any way...

She had just got done plowing my ass in the back yard and I was starting to plow hers. We heard our gate latch and both looked over our shoulders. 2 friends of hers were walking towards us, undressing, and putting on their own strap-ons. Before the first was done with my ass I blew in my wife. The 2nd took my place in her ass, then they switched.

One of my wifes coworkers and his wife showed up about the time we all moved inside. He took to sucking me as his wife pegged my ass. The wife got spitroasted by her friends. Before the weekend was over, there were 10 of the wifes friends, coworkers, and her sister with her husband that had joined us...3 men and 7 women in total...all the women with varying sizes and colors of strap-ons.

The wife admitted to planning it all to give me the fucking of a lifetime over 2 days. She also appologized because 3 guys and 2 gals didn't show up. I told her I was glad because my ass and throat wouldn't have survived.

I LOVE MY WIFE!

Paid Off A Debt

I never expected to confess, but here goes.

Im a reasonably happily married man who, I guess you can call it cheating but, I don't.

Theresa is a coworker, a few years younger than me, and is following me up the corporate ladder at the plant. Smart, great personality and has the " one of the boys" sense of humor. We constantly double entendre everything, to the extent that if you don't hear " That's what she said" or " have you tried lubing it?" you wonder if she even heard you. One of the threats she has always made to me after I help her out of a jam is " One of these days, I'm gonna pay you back with a blowjob", I laugh and tell her, "Sure you will".

Well, a few weeks ago, I received a promotion, and started grooming Theresa to take my position. Then, one of the floor employees filled a harassment suit against me, saying I repeatedly insulted and hindered his promotional possibilities because he was gay.
Needless to say, my promotion was held back, I was suspended for 3 days and a hearing was scheduled regarding termination.

Luckily for me, Theresa was outside having a smoke, when the gentleman was bragging to his friends that he was going to get me fired, and would then get a promotion. She recorded it on her phone, pretending to be texting and turned it in to HR. 2 days later, I received my promotion, my pay and the incident was expunged from my file.

The next Saturday, during inventory ( mandatory overtime) I saw Theresa and knew I had to thank her. I pulled her into the ladies lounge, locked the door and told her it was blowjob time. I didn't give her a chance to do anything, I just reached under her sundress and grabbed her panties and started yanking them down. Verbally, she protested, but she spread her legs a bit and moved her hips to help get them off. I sat her on the couch, pulled her dress up and started kissing the insides of her thighs until she spread them wide enough for me to see my target.

Because Theresa is a single mom, I was surprised how well trimmed she was, her reddish hair was thin and neat. I started kissing closer and closer to her mound, and she kept telling me I didn't have to do this, but I did. The first few licks of her outer lips had her gasp, and as I started to lick from the bottom up towards her clit, she took her fingers and spread them for me. I spent my time trying my damdest to have her enjoy this. Switched up from licks, to inserting my tongue as deep as I could. Then she started getting into it. Hips moving, I saw her reaching and squeezing her tit, I knew she was getting close, so I did something that always got my wife over the edge, I sucked her clit like it was a nipple then after a bit, sucked it between my lips and ran my tongue back and forth over it at the same time.

Theresa started talking, " please fuck me", "put it in, NOW!" , and I almost laughed when she said " you're killing me Smalls". That's when she went over the edge. I saw her biting her arm trying to be quiet. Her body went stiff for a few seconds and then she kind of went limp, mumbling " you suck, I fucking hate you!" I moved away and couldn't believe how red her face was. You couldn't even see her freckles. I walked over and washed my face in the sink. When I came back, I picked up her panties, stuck my hand out and helped her off the couch. I tried to help her put them back on but said, she needed to air it out first. I snuck out the door and told her to wait a few before returning to work.

That Monday, there was a typewritten note in my inbox saying " It's on like Donkey Kong" with a red lipstick kiss on the paper with a hand drawn dick headed in!

While He Was Away

While he was away, my husband gave me a pass to sleep with other guys as long as I told him about it. After two weeks, a guy I had known from high school days came into town and stayed with me for nearly a week. We had not had sex in high school, but we made up for it while he was with me. My friend was attractive and very fit. We didn't really discuss sex, but just went to bed. He fucked me really well and I was lost in my orgasms with him. The first day, he had me six times. Before his visit ended, he had come in me more times than I can remember. I loved sucking his dick and then fucking him. Twice I let him fuck me in the ass because my pussy was sore. I was his slut in several ways.

I told my husband thank I had fucked my friend. I did not tell him my friend had fucked me over six days and had cum in my ass. I thought he would think that was a bit over the line. However, my husband got off knowing I had been fucked and he fucked me hard when I told him how it happened. He liked that I had been a slut. I really enjoyed the excitement and eroticism of my friend fucking me so much. A different penis in me was very exciting. And while I look forward to being fucked again by another guy, my heart is with my husband. Having his okay to share myself with other guys is a g*ft.

Shared My Wife For The First Time

Rick is my best friend and we have known each other for years. Over the past two years he has also become friends with my wife Janel. Janel is five years younger than me. She is very pretty with a trim body. She likes sex and she likes sucking my erection and moans while she is sucking. Lately I had thought about sharing her with Rick. I mentioned it to Rick.

We invited Rick over for dinner a couple of weeks ago. After dinner we drank more wine and were all pretty high. We were on the couch together and I told Janel that Rick was going to fuck her while I held her. At first she was hesitant, but I without asking I undressed her and she sat naked in my lap with her back against my chest and Rick went down on his knees between her legs. He sucked and licked her clit and fingered her. Before long Janel was moaning and I told Rick to fuck her. He pushed into Janel and she gasped. I held her while he fucked her for a long time. Janel would shudder in my arms as she had orgasms. I asked Janel if she wanted Rick to fill her and she said yes. Moments later, Rick emptied into her and she had another orgasm and moaned loudly. When they were through, I fucked a very wet Janel and came in her as well. After a bit Rick went home.

Janel and I talked about what we had done. I asked her if she would like to have Rick now and again. During the past two weeks, Janel shared herself again and then on Saturday, she had Rick by herself in our guest room and she fucked him twice. I love fucking her after Rick. If Janel's up for it I hope we can continue the sharing for a while.

First Wife Sharing

Finally convinced my sexy wife to have an adventure. I’m not a cuck, in that I don’t go for humiliation and I’m a very good lover. I do however believe that after many years together, we can have some fun with other people and not damage our relationship. I suppose I’m more of a stag. Anyway, a guy had been reaching out to my wife in social media DMs. She’s very attractive and men always hit on her. It’s something I enjoy. It turns me on that everyone wants her. This guy was especially persistent. He is a very handsome black bodybuilder. My wife looks very young, so she attracts young guys. He was no exception at 26 years old to her 45. People never believe her actual age. She always shows me the messages she gets from guys and we usually laugh. Something about this guy was different. He was very literate and seductive, without being creepy. So, after decades of having sex with only me, I suggested that she g*ft herself to him, for a fun little adventure. I’m good in bed, but I’m not a 26 year old black bodybuilder, so I thought it would be a treat for her. I didn’t tell her, but I reached out to him myself and, to his surprise, I gave him my blessing to go for it. I even provided a six hour window on a specific day when I’d be playing golf and she’d be home alone. He was very excited. When the day came, I left for golf and told my wife that, if she wanted to invite him over, I was fine with it. She laughed, said no that she was too shy, and I left. While I was away, my security cameras picked him up at my door. He took the initiative to be bold and came to the door. He was rewarded. Watching her go from shy to a dirty little slut was awesome. The sex they had was athletic, sexy and very pornograhic. He’s truly a sexual specimen and gave her a porno star experience. (Cameras are a nice luxury). For three hours, they had some awesome and wet sex. He did things I can’t physically do to her and he made her spray, which I’ve never done to her. I loved seeing them like that. He was fucking her standing up at some point, holding her little body up like it was nothing, when he pulled out and I saw the actual size of him. Insane! He sprayed cum all over her stomach, then pushed his huge cum covered cock back inside of her and fucked her for twenty more minutes. She made sounds that still echoe in my brain when I think about it. Finally, with her naked on her knees, he finished one last time in her mouth. Once he left, she called me, full of excitement and begged me to hurry home. I rushed home and she jumped me wanting me to reclaim her. I’ll be honest, but the first time you kiss your wife and taste another man’s cum on her lips, when your wife’s pussy is sloppy and stretched by another guy, it’s surreal. Truthfully, I really enjoyed the taste and smell of him on her. It was very erotic and taboo. I have a nice cock, but this guy has the biggest uncut monster. There’s something primal about it and how it felt. Sadly, she said that, while she loved how dirty she felt, she did not love how big he was and prefers me. She was in pain for a week for his ravaging and, although he asks her every week for more fun, she has refused to see him again for over six months. She says it was probably a one-and-done. I wouldn’t mind doing it again Lol! If this is something you’re thinking about - go for it. It’s better than you imagine. Our sex has never been better and the dirty talk is next level.

Moms Friend Took My Virginity

I was 19 years old and it was my first summer break of college. I was back home all summer and my parents had a cruise planned in the beginning of July so I would be home alone for two weeks

It was hot out and the central air went out and I had to call someone to fix it. There was a 2 day wait. So I bought a ac just for a bedroom and decided to walk around in my underwear since no one else was there

I’m laying on the couch in the living room in just my tighty whities with the sliding glass doors open when my friends mom shows up.

She saw me hard in my briefs and I quickly apologized saying let me get pants. She insisted I was fine and it was okay I was in just underwear. But I still put shorts on.

We were in my room where I had a window ac. I pulled a love seat in there so I could basically live in my room until the central air was fixed. My mom’s friend and I were sitting in there and she was asking me about my first year of college.

She got on the topic of sex and I kinda hesitated but admitted I was a virgin. Told her I was too shy to be hitting on random girls for dorm room sex. She was surprised and insisted I was a good looking guy and said I obviously saw your filling up your briefs well

She was teaching me how to kiss at first and I got hard. She said get on the bed.

She pulled my shorts off and I was in just my tighty whities. I was rock hard. She took off her shirt and then her pants. She was just wearing a bra and a thong. There I was about to have sex with my mom’s friend who was 49.

She gets in bed with me and has me take her bra off. She then pulls my tighty whities off and my shaved dick is exposed. She grabs it. Comments on me being shaved then starts to suck me. The bj alone was really nice. I warned her I was gonna cum and she stopped to make sure I wouldn’t.

Then she says I’m assuming a guy your age has a few condoms ready. I looked at her and said no I’ve never had one. She was surprised I’ve never had one but said we can go without one but told me to make sure I wear a rubber at college

She got on top and sat on my dick with her wet pussy. The feeling of a warm pussy riding my dick was really hot. Then I suggested we do missionary. But before that I decided to try and eat pussy. So I dove head first into her shaved pussy. She guided me to the right spots and I ate her out until she was very satisfied

Then I fucked her in missionary. I didn’t last long before I felt my cum coming. I warned her I was gonna cum and she never told me to pull out so I cummed in her pussy. Really intense orgasm.

As we laid there naked and her telling me I can’t tell a soul about her taking my virginity I got hard again. This time she gave me a bj until I cummed in her mouth.

By that point I was drained and felt great. She was getting dressed. As she was standing in her thong putting her shirt back on she told me to go wash my dick then get dressed and she’d take me out to get some food. And she said I’m gonna get you a box of rubbers too.

BF's Sister

I've known this woman for just over 25 years and played hockey with her husband for the last 8 years. She is my best friends sister who I've always wanted to fuck, but she revealed to me recently her brother would never allow her to date me when we were in our teens. We have come close several times and there is always sexual tension when we are together, but still nothing. For the last few years while showering after games, I have noticed him glancing at my cock too many times in the shower for it to be normal. A little weirded out by it to be honest, but maybe he was just measuring himself up versus other men.

Well they held a Christmas party and a few guests were staying over due to distance (like me), but most due to alcohol consumption. I don't drink and maybe had 2 or 3 during the netire night so I was my normal self. I guess the alcohol loosened up her inhibitions though and to strangers it would have looked like we were the couple. She would grind my cock at every chance and let her tits hang in front of my face through the unbuttoned top.

When things were wrapping up she told me she had gotten the okay from hubby to fuck me, but he had to be present. Hubby had told her in his words I had a very nice cock, but she knew this already from my the outline in my swimming shorts. We head off to the room and I strip down, layback in a chair when she starts giving me head. The husband looks like he enjoys watching and so I close my eyes as to not be weirded out by him. About 5 minutes or so goes by and she pauses briefly to clear her throat and resumes.

Minutes later I'm about to cum and open my eyes to find hubby sucking my cock. I'm pissed off, jump up in a panic and start swearing. She tells me to relax and what difference does it make as long as the end result is me blowing my load. I calm down, sit down again while both begin working my cock and balls. I blow a couple of streams in to his mouth and pull out to blow the remainder on his face. To add insult I smack him several times with my cock off his forehead and cheeks. His wife laughs at him.

Later that night I get to fuck her several times while he watches. Since Christmas I still fuck her and yes the hubby still enjoys sucking my cock along with her.

I don't think of myself being gay or bi for having that happen to me.,,but I will not be sucking his or any others. As I sit here typing this I can feel the precum flowing and my cock looks like a candle with melted wax running down the side. I have often thought about tasting my own cum, but can't bring myself to do so. Shot many loads in a coffee mug, but nope.

It Just Happened

My wife is a year older then me she has a sister that’s a couple of years older then her. My wife was a senior in high school when we met she was dating a senior I knew it she lived in the same neighborhood and our parents knew each other. Il leave out the names and use initials I’m sure they would be mad if they read this since nobody knows what goes on in our house. Not even my close friends. Her older sister had always been wild. I never dated her I just started fucking her. L &N looked a lot alike they could have passed for twins L had a birth mark right on her ass cheek that was the only thing that when baked could tell them apart. Same size tits same short petites body frame. L was more adventurous then N but could get her to do just about anything. When N graduated her bf at the time had in listed to join the military. Back then notebooks where big and she would write down notes and what happened and what she wanted to happen. L being wild spent some time bouncing form house to house Il sure getting fucked along the way ones sad mostly because my personal fuck doll had moved or so I thought. Before she left we had gone to through her sisters notebook and had read how she was still a virgin and her bf at the time wanted her to have sex with him before he left for boot camp. He’d be gone for weeks and she had agreed but it never happened they never had the time with graduations and parties her mother probably kept her busy on purpose knowing what her intentions where by also reading her notes. He left he had his party i was not invited of course but her parents where and they kept her close by. After he left I made it a purpose to hang out with her and her being lonely gladly lies the attention. Her mother was especially excited because I came form a great family and it was known being the only son I was going into the family business. My father owns a bunch of properties and ranches so I always worked farming or developing land by running heavy equipment. I could drive a loader before I could drive a car. In a few weeks N and I where inseparable she often came to visit me on my lunch break since it was summer. Her soon to be ex was supposed to come back in late August from boot camp. It all happened so fast that when he came back he came back to N being a few weeks pregnant. He begged her to go with him she told him she had grown a lot since he left and had met someone and that someone had gotten her pregnant. I finished my senior year like a normal senior except I was expecting a baby boy. As planned I went to work for my dad and easily supported my wife and new baby. N needed not to worry or work. She was a very good wife to be and mother. Motherhood fit her she is a greets women. When my son was ready to turn 1 she returned L came back and her and her sister where close very close and of course she asked if she could stay with us for bit. Bad idea first day she was there sucking me off in my pickup truck begging me to fuck her. It was obvious that she was screwing me and my soon to be wife had a good idea. I married N and was fucking L. Married to N we had a small gathering N told me she knew about myself and her sister. She went on to tell me that her sister had always asked her to help her with her bfs and she would ignore her. I wanted a better explanation she flat out said that her sister always begged her to fuck her boyfriend’s with her. She said she never did it and she had asked her if she would fuck me with her. She asked me if I wanted that. I wasn’t going to lie and said who wouldn’t. She said ok and nothing else was said. A few weeks after the wedding I’m thinking she decided against it and I wasn’t going to bring it up. I came home from work the baby was at my parents my beautiful wife had made arrangements prior to. I walked in my wife N in a thong she knows what I like her sister also in a thong bent over thing to the side and my wife is ramming her fingers in her. Best night of my life I was sucked fucked licked and sprayed then with cum. It took a while to figure things out I built a bigger home I have guest house now. That happened 20 or so years ago N and I have 2 kids L and I have 1 son. My parents had no idea we share one room one bed my wife and second wife have given me every thing I ever wanted and more. I know I have the best life when I sit down on a Friday night kids asleep we go to our basement apartment and I watch my 2 wives go at each other. 2 sisters giving me a bj and fucking me and each other. Some would call it gross or won’t believe me but I’m the one with 2 true sister wives.

It So Satisfying

This is me getting back at my POS neighbor from across the street. I moved in a few years ago and the neighbor across the street was always complaining about my car then my truck then to many people then my gf at the time was parking in the street. I get it at first I did have a few get togethers and I invited everyone including him and his wife and they didn’t come. His wife Cedes is close to my age a few years younger then him she is a runner. Keeps in shape absolutely flat chested no boobs just big hard nipples. But what she doesn’t have up top she has on the bottom. She has a very nice ass big slim waist type. I’m n running shorts they cover very little and i started flirting with her once I saw her in her shorts. I have a small alley way that separates my house for my neighbors next to me. She can literally run out her house straight across from her house to the small alley that ends up at the park. From there you can run around the work and back to my or her house and it’s exactly 2 and half miles. I have a large window that looks directly to their yard. I have a semi tinted window to make it harder to see inside. I sit in the front look directly into there yard I see Cedes walk out close the door behind her I see him in there kitchen I drink my coffee i then see his garage door open he spends time in there tinkering with his old jeep. I hear my back door open she walks into my living room comes over gives me a kiss sits on my lap she undresses drops to her knees takes me in her mouth and blows me while I watch her husband tinker around with his jeep. After I cum she sits on my table and i enjoy eating her out putting her on all 4s facing her husband I tongue her ass and pussy suck on her clit. I first fuck her pussy blast in her mouth spin her back have her sit directly on my cock splitting her giant ass with my dick. She can also see her husband she stands then slams back down on my cock I run her clit and a short time later she’s crying and squirting hard. This last for a few hours then I send her home full and relaxed. She often leave’s with wobbly legs. Her routine is to take a bath after and then take a nap. She is mostly a morning fuck but sometimes she will come over in the afternoon if he does golfing or out with his friends or family. I have tons of pictures and videos. She likes to watch herself getting railed it gets her going. I always have her home movies on when she’s over. Or when she’s home and i have friends over. I almost have her convinced to try a DP with me and my cousin. Il post when that happens or maybe that’s the first video I pat of her. I’d loved to send it to her ass of a husband.