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:

Birthday Cruise And Discovering Our Naughty Side

I thought I'd share an experience from ten years ago. My wife was turning fifty and more than anything she wanted to go on a cruise. For me it was quite a reach saving over two years and keeping the savings from her. We caught a cruise on the Mediterranean, ten days from Barcelona, Sicily, Italy, Malta and back stopping at Ibiza. We caught a flight out of London to Barcelona, took a day to see the Cathedral, and boarded our ship. We got a nice entry level suite with a balcony.

Once we set out to sea we went around to discover the ship. We found a bar with live musicians and we took our seats for a birthday drink and live music. Two women came up and asked if they could sit beside us, half a couch and the empty chair. We became on board buddies, they were experienced cruisers, both divorced from rich men.

We had dinner in the dining room with them, by the time the desert was served we felt like long time friends. Now here is where it got interesting, they asked my wife if they could borrow me. For an after dinner orgy. Three women intent on bringing a man to his knees. To my surprise my wife agreed, and since we had the suite and king size bed we retired up there.

All three women became teenagers with one old man to 'service' them. I got more than one dose of play p!lls, and three women getting nasty. It was playful, women naked, whole one was serviced the other two played lesbian. My wife took it all in stride, her first orgy. By the time the moon was high over the Mediterranean one old man was dead, snd three ladies telling tall tales of days gone by.

Ten days, ten days. I admit I was stretched beyond my libido, but three naked women playing hide the weenie, and one lone man providing servicing got me going after a day of cruising, or walking the towns we visited. I'm not complaining, and certainly not bragging.

Back in our cottage we've lived in for a quarter century we have pictures, some private, and a basketful of memories. My wife, she keeps in touch and makes arrangements for sharing holidays. We've been on another cruise, as soon as we can save up for it, two suites, side by side, so we can enjoy the company.

It Started When She Needed My Help, Now It's Our Thing

This happened several years ago. My best friend gave birth and asked me to come sit with her and help with the housework while she tended to her baby. A week after her baby came home she asked if I didn't mind taking care of H's needs. Like? Well, like giving him some nooky.

A friend is a friend in need. He wasn't asking, but he wasn't refusing. He was nice enough, a little to mechanical. I complained and asked my friend to suggest to him to get his shit together when he 'fucks' me. I need 'relief' too.

It took many tries, some with the help of my friend. Hold his dick in her hand and guide it in and out of my vagina. Rub my clit with baby oil, while he fucks me. If, and we were long past a discussion, if he's going to make me, then 'just do it'.

As I say it's been several years and he makes sure I stay satisfied and happy. We keep his attention with variety, and that may or may not include some long wet kisses, tweaking nipples, and baby oil clit loving. After all, we are best friends and we need to share affections.

Halloween Party

My wife and I were invited to a Halloween Party with a Cowboys and Cowgirls theme. It was through a work friend of hers that knew the person throwing the party and my wife really wanted to go. I really didn’t want to go because I didn’t know anyone who would be there. So we got dressed up my wife looking sexy as hell short Jean skirt no panties on cowboy boots and her top was her shirt tied up with the buttons open showing cleavage and her stomach she definitely looked good and her cowboy hat. We get there the party has at least 75-100 people there music going a mechanical bull setup in the backyard. We grab some drinks walking around then my wife sees her work friend talking to some guys and tells me she’s going to go say hello to her friend she’ll be back. So my wife goes over and starts talking with them, I’m pretty much left alone so I walk over to where the bull is to get a better view to watch the people ride it. At least half an hour goes by still no wife and lost site of her, so I go get another drink walk around a little then head back towards the bull to watch mostly the women riding it. About half an hour later I see my wife going to get on and she’s looking a little buzzed climbs on her skirt rides up and she’s showing her pussy from behind as the bull leans forward the guy operating it isn’t really trying to throw her off and a bunch of the guys around are all hollering loving the view. After a couple of minutes she falls off and laying on her back her knees up legs wide open before getting up. I’m completely on the other side so when she leaves the bull area I lose sight of her again. I go get another drink I’m pretty bored and again don’t know anyone there so I walk out front of the house and down the block to where we parked and get in our car just sitting there listening to some music.

About an hour later I go back in not the party looking for my wife don’t see her anywhere outside or downstairs in the house. So I didn’t know if I should go upstairs since I don’t know the owner of the house but as I’m by the stairs I see two guys coming down laughing talking about how hot that slut is. So I go up walk down the hallway and there’s at least 10 guys in the room some watching some with their cocks out waiting there turn and others getting sucked fucked or hand job by my willing wife who’s covered in cum. She loving every minute of it. I definitely didn’t want to make a scene because most of these guys knew each other because they were all talking calling each other by their names talking about my wife being a slut whore, So I just hung out in the background and watched her get gangbanged by all of them a few leaving after they came a few more came in and some with way bigger dicks then me.

After about two hours she was done passed out on her back legs spread her pussy swollen cum running out of it cum on her face her tits. At that point I picked her up and tried to carry her but needed help so I went downstairs and asked one of the guys for help when we got upstairs he was asking me if I knew who she was and she had some good pussy so I told him she was my wife. He just started laughing saying Damn. We get her down the stairs and he helps me get her to the car he’s doing more of the carrying and groping because I’m holding her clothes. As we’re getting her to the car I let go of her to unlock and open the passenger door but when I run around he has her laying down in the grass and is pulling out his bigger then mine hard cock, he tells me he wants her pussy one more time and slides into her starts pumping her she’s moaning lightly and pushing her hips back into him after a few minutes he’s got her legs up holding thrusting hard cums deep into her pussy. He gets up thanks me and leaves going back to the party. I’m hard and horny so I pick her up she’s sloppy drunk in and out of it throw her into the back seat get in the back lock the doors and the windows are tinted so hard to see in. I open her legs and start eating her used pussy she starts moaning and grinding her pussy on my face then she tells me Don’t stop and climaxes. I keep eating her out the amount of cum from all those guys is just flowing out into my mouth, I bring her to another three orgasms over the n cut thirty minutes of eating her out. Then I finally climb on her and slide my cock into her I can’t believe how good her pussy feels with all that cum in it. After maybe five strokes I cum hard into her adding to what’s left that I didn’t eat out of her. I pull up my jeans and get in the drivers seat then drive home.

She Was A Slut

When I let my wife let’s just say she was in a compromising position. She was a pretty party girl that drank to much and then let guys one night stands one on one or groups have fun with her. I met her at a party out in the middle of no where that friends of friends where throwing. Myself and some guy I had never met other and banged the shit out of her literally. She was dirty and I dug it. After we plastered her face that night the guy took off and i stayed and chatted her up. Don’t know why but i did. We exchanged numbers and on a few occasions would text or call and hook up. We were close to finishing school and she told me that she would be moving back home. Before graduation we would see each other and she started hanging out with me a little more and more. She was a good looking girl. Short Red Head with a nice rack and some thick thighs and a great ass. The people we knew and hung out with came and went so her and I where the only ones that knew that she was a real slut. A few months after we met we were stuck at the hip or better yet my cock was stuck in her rear or pussy. Literally sexual until it wasn’t. We where at a party we where drinking and a few guys had hit on her. They didn’t know her or how easy she typically was. I had gone to get us drinks and came back to one guy chatting her up. As blitzed as she was I walked up to her mumbling I have a bf asshole fuck off. I squeezed her ass as I walked up she spun around was going to smack me and ended up kissing me once she realized who it was. A few months later we left school after graduating. We did not take it slow. We ended up moving back to my town where I went to work in the family business. My parents set me up to succeed. Being the good parents they are they adored my gf at the time now my wife. She slowly started to tell me that she dealt with some issues and low self esteem. She said that she remembers when myself and Rando guy fucked her and as soon as he was done using her he left like all the others but I didn’t. I stuck around and talked to her as she was a human being. It made me sad that she felt that way to be honest. We dated for a bit and soon enough we where expecting. 2 great sons and almost 20 years married. Yes she was a slut and yes now she is my slut. I’m definitely not the jealous type because some guys would not have stuck around. She keeps telling me that my love for her ass made me do it. She is probably right lol.

Girlfriend Shared

It was summer when we were home from college. A close friend, Bob, had a secluded cabin in the local mountains. My girlfriend Margie and I spent every weekend with Bob at the cabin. We made some great meals, got high, and generally had a good time together. One Saturday night, we were in the living room and I was making out with my girlfriend. Nothing that Bob hadn't seen before. Occasionally Margie would make out aa little bit with Bob, but it never went beyond kissing. But this night, I had Margie lie on the carpet. After we had been kissing for awhile I began to unbutton her top. She pushed my hands away, but when I said to her it was all good, she became very calm and she let me undress her completely. I continued to kiss her and feel her until she was wet. Bob was watching all of this and was stroking himself. I looked into Margie's eyes and told her that Bob was going to fuck her now. When she looked at me I said Bob was our very good friend and she should let him make love with her. I motioned to Bob and he got between Margie's legs and started fucking her. As he continued, Margie began to moan and thrust back. I could tell she was about to have an orgasm. As she did, Bob emptied into her. When he finished, I pushed into Margie and fucked her hard. It had been very erotic to watch her fucking Bob. She was so lubricated, that I came quickly. We each had Margie again that night. When we were alone, I asked Margie how she felt about being shared. She told me that once I had told her it was okay, she was fine with being fucked by Bob. For the next month and a half, before we returned to college, we shared Margie every weekend. Margie and I went to the same college and shared an apartment. When we got back, she asked me to set it up so she could have threesomes. My best friend and I took turns with Margie at least once a week during our senior year. Margie loved having two men to fuck her.

Granddaughter At The Swing Club

The wife and I have done at least one monthly visit to the local swinger club since we were 18. This past visit, we entered the room that usually hosts orgies or gangbangs. There was a GB going on and by the sounds of it, she was getting it good and thoroughly enjoying herself. The wife and I sat back catching only glimpses of her getting spitroasted, DP'd, or airtight.

The wife sucked a few cocks that either recently finished in her or didn't want to wait their turn. A couple of the wife's sucked my cock. While one was riding me I was sucked her husband.

One thing led to another and...low & behold...the gangbang girl was my freshly 18yearold granddaughter. She not only witnessed me and her grandma getting it on with other men & women, but we were witness to her taking more cocks and loads in all her holes than I could count.

We showered then sat in the restaurant and talked. We were joined by my wife's sister, who had brought her for her first time.

After a lengthy and indepth conversation about the last 36 years of our sexlives, and the last 3hours of her new lifestyle, we hugged and went on our way for the next few hours.

Next weekends monthly family dinner will have a new element. Looks like it's now 4 generations of our family that have been in the lifestyle...3 current.

Late To The Game

I’m in Vegas for an annual baseball tournament that my son’s travel ball team plays in every year. My husband could not come so it was my son and I traveling with the rest of the team. We get along with everyone so it makes it fun. First day we hitched a ride with another one of the parents we had a team bonding event then all the patients met there kids go to the arcade while the parents hit the bar. Drinks were flowing I always considered myself average looking blond with big tits and a bubble butt. I’m proud of my body and like to show it off. Drinks where flowing we stayed out late my son came and found me and we went back to the room. I was being chatted up by one of the dads. Heavy flirting and drinks made it fun. The next I dove and the dad I was flirting with hitched a ride with me. We got to the park dropped the kids off at the entrance an hour before the game and I went and parked our car. As soon as we parked he leaned in and kissed me I let him kiss me I kissed back he felt on my tits he was aggressive I like a guy that takes charge it gets me off. He grabbed the back of my head by my hair and shove my Gabe into his crotch. Dick came out and I gladly took into my mouth and begging to give him head. He stopped me told me to get in then back seat of my Tahoe. I did as I did he gave me ass a smack and lifted up my dress that I had on. Dress comes off bra is off ass is out and tits are getting groped sucked licked. Fingered me for a bit before I felt his cock split my ass cheeks. All he let saying was I have wanted to fuck this ass since the first day I ever saw it. He fucked me bareback. Pushing into one hole then another. He fucked me for over an hour when we realized the game had already started. I came hard as he fucked me into my back seat. When we finished my pussy and ass where a mess my makeup was a mess. I looked just like I had been thoroughly fucked. He made me go with out a bra so my nipples where sticking out. I was a leaky mess. That was Friday and I have been fucked my him and another dad about a dozen times in there room and my room while the kids are in the arcade. I discovered that I like and can take a DP. What happens in Vegas stays in Vegas hopefully.

So I Think I'm A Cuck...

So about 5 years into our marriage I was sleeping on the couch downstairs. I woke up and quickly realized my husband was jerking off to porn on our computer. I pretended to be asleep, getting wetter by the second, and watched as he finished. It was insanely hot to watch him jerk off to freshly shaved pussies and he came EVERYWHERE.
I didn't really know what to do with these feelings, I was slightly ashamed and felt kind of weird about it. Eventually I convinced him to let me watch him. I was looking at pictures of girls, and would take note of when he'd stroke himself a little more vigorously. Turned out he really loved upskirts, and wet panties. I got super turned on when I asked him what he'd do if he saw this in person, and when he was worked up enough he asked for my permission to cum to this sweet, innie pussy in white, wet panties. I still think about this when I masturbate. Watching him stroke himself really hard and shoot ropes of cum to this other woman was a really weird, extremely sexy feeling.

One Day Refresher Course

I am 36 in decent shape and like to show off a bit. I do like the attention but this time I took it a little to far. I have to do this refresher course every year most of the people there are guys some young some old myself and another women where the only 2 women I’m a class of 40. I was late so I ended up at the back of the class and was leaning against a high desk. Every one else was sitting except myself and 2 older gentleman. I wore a dress about to my knees nothing super sexy just a snug fit. The lights went off and this class is a lot of 20-30 minute movies and some explanation of what happened and what could be avoided. Being in the back in the dark made it really easy to go with out being seeing. I noticed the younger of the 2 guys next to me kept looking at my ass. I made sure he got a good view and made sure to lean forward on the high table desk we where at. Figured I’d show off a little and give him something to look at. It was quite and dark when I though I felt a hand graze my ass. Didn’t say anything or move then I felt it again. This time a firm squeeze thy made me jump a bit. I was about to look over when I felt a hand up my dress and he had good aim and hit the dead center of my slit. He rubbed fast through the fabric and I did everything I could to stay quiet. I then heard him right next to my ear telling me what a good little slut I was. Shocked wet and horny I didn’t say anything kept my mouth closed and eyes shut. He slid 2 fingers in me and went slow. I should have moved but I did not. Then fingers came out and his middle finger went straight into my ass. He hit his knuckle it hurt a little but again I kept quiet. 2 hours into the class i had been finger fucked and my ass fingered. We took a break nothings a said I went to the restroom and rubbed my self to a shaking orgasm. Went back after 20 minutes and again was finger fucked this time I had removed my panties. Long story short at lunch I was fucked in his truck for close to an hour. Fingered until the end of the day. Was supposed to meet my husband for dinner. Told him i was going to be late because the class ran late. I was a little over an hour late got to the restaurant leaking cum form my ass and pussy. To make things worse the guy stold my panties so I was a sticky mess. I had to go shower and wash up. I’m hoping that next year I can do this again. Made the class tolerant

Submissive Wife

In college, my wife and I rented a three bedroom house with two other students, a man and a woman. My wife, Gina, was beautiful with a great body. She was also introverted and somewhat submissive. Regardless, she really liked sex and was very responsive when we were in bed. For some time, I had a fantasy about another guy sleeping with Gina, After a few weeks with our new housemates, I told Gina one night that I wanted her to sleep with Bill, our male housemate. As I made love with Gina, I asked her to imagine that it was Bill in her, but she was hesitant. A few days later I talked with Bill and let him know I wanted him to seduce Gina. He was excited by the prospect, but wondered if Gina would be willing. Later that day I told Gina that Bill was going to fuck her and she was to let him. When she again seemed uncertain, I simply told her it was going to happen.

Bill and I talked several days later and he told me he had slept with Gina. While I was in class one morning, he came up behind her in the kitchen, hugged her, kissed her, and felt her. He said Gina went along and he took her to his bedroom, undressed her and after playing with her, entered her and fucked her. I asked him if Gina had been responsive and he told me she had been a bit passive, but had an orgasm. That night I asked Gina if she had enjoyed Bill and she said she had done what I wanted. I told her that she would gradually like it more and I wanted her to continue to let Bill have her.

Several weeks went by without talking with Gina about sleeping with Bill. I finally asked her and she seemed embarrassed. When I asked again, the story came out bit by bit. Bill had pulled Gina into bed with him every morning I had been in class since their first time. Gina told me he had slept with him and he had come in her at least twice every time they had been in bed. I asked Gina if she liked sex with Bill and she admitted she did. In talking with Bill, he told me that after a couple of weeks Gina became more and more responsive. He said Gina had started coming to him rather than him making the moves.

Hearing Gina and Bill describe their sex together made me really hot and Gina and I spent hours in bed. The more she revealed about sleeping with Bill, the more I wanted her. Initially, she had fucked Bill because I told her to. Now she wanted another man's penis in her. For the rest of the academic year, Gina fucked Bill regularly. Bill and I finally got Gina into some threesomes and she loved four hands on her body and two men giving her orgasms. Gina is still submissive in some ways, but really has opened up about sex.

When college was finished, we moved away to another city for jobs. When I asked Gina if she missed having another guy to sleep with, she admitted she had gotten off on having another man want her. Eventually we made some good friends in our new city. We met another couple and became great friends with them. That friendship , over time, resulted in us swapping partners a couple of weekends each month at each other's homes. Gina loves the arrangement and we have all remained tight friends. About once a year Bill will visit and spend a couple of nights sleeping with Gina. She always has fun making love with him on those rare occasions.