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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:

- Funny As Fuck -
Straight Male / 24

Thursday Night Football

I have been seeing this older lady who lives down the street. Yes she’s married no kids yet. Not sure what her and her husband have going on but they argue constantly and of course since we have been booking up it’s gotten worse. I have friends over for Thursday night so she is usually gone by the time the game starts. I get home from work around 3 so we have a couple of hours to go at it. Stacy is a good looking blond pale skin nice ass big rack big hair type. Her attitude is blah but she can fuck and she looks great naked. She is definitely not the kind you marry but sure is the kind you keep around for fun. A few Thursdays ago I asked her to stay for the game. Typically when she comes over she dresses very provocative for me. This day was no different she was in a tight shirt no bra and a skirt that is supposed to be worn with shorts underneath or leggings. She had only worn a g string so she paraded for me with that thin piece of material splitting her meaty pussy lips. Meaty to say the least Stacy has wings that you can stretch out pussy always feels good and has received anal more and more as she hangs out. We had started to mess around in the living room so by the time we got back into my room she was just in her g string. Her skirt and shirt where left there. My 2 friends showed up and as always let them self in and sat down. While snapping a few pics and videos I sent a pic of Stacy on all 4s taking it up the rear to my buddy and said will be here for a bit help yourself to a beer. An hour later Stacy came out in her g string and grabbed her skirt and shirt said hello and came back to my room. 30 minutes later I blasted her face cum covered it and sent her back out had her ask if they wanted some. She had cum on her chin both declined and she came back in. I told her to joke around with them and she did. First time she had a good laugh and saw an attitude change. Haven’t shared her but we have talked about it maybe one of these Thursdays I told her we can try that DP we always watch. Nervously she tells me she would try it. Il update when it happens if it happens not sure I’m into that but I guess if I’m going to let it happen might as well be with someone I’m not attached to

0
# 82959 - by Bart / October 2, 2025
- Obsessions -
Bi-Sexual Female / 45

I Love Being A Shared Wife

I've aways been a slut. Even before my now husband of 25 years and I met. While we were dating in highschool he shared me. My husband is no joke with his cock. He can go for hours, is multi orgasmic, and knows how to use it! I just can never get enough, so he tries his bet to make sure I get all I can. He suplies me with all the toys and devices I want. I'm shared every weekend with his friends, family, coworkers...mostly male but also female... and many times during the week. We attend many swinger events throughout the region we live in, so I get plenty of veriety. We are members of 'organizations' that, among other activities, include various gangbangs and BDSM...both indoors and out.

Any and every way I and or my husband can imagine, he makes it happen and I do it...and I enjoy it!



Just thought I'd share.

4
# 82962 - by Jenny / October 2, 2025
- Evil Thoughts and Deeds -
Straight Female / 39

I Said No …, But

Recently I was out of town for a company meeting. The evening before it started a co-worker and I were preparing for a presentation we were to present the next day.
We were sitting next to each other on the sofa in my hotel room going over our strategy for the meeting when he put his hand on my leg. I put my hand on his reminding him I was married then he leaned over and kissed me.
We kissed a few times then he started his hand up my skirt. I said No !! but he was quickly to where he was headed. My “No” then changed to “Oh my god” when he had gotten me very aroused easing me down on the sofa and getting himself out.
I immediately told him not without a condom because I wasn’t on birth control but again he wasted no time this time penetrating me with what became an incredible love making tool.
The extended experience was amazing with him causing me to have not one but two extremely intense orgasms.
I just knew I was going to be in trouble since I had enjoyed it so much but luckily my period arrived right on time a couple of weeks later.
I was very thankful for that because had I gotten pregnant I would not have known if it was his or my husband’s.

3
# 82965 - by Anna / October 2, 2025
- My Spouse -
Straight Male / 37

I Never Knew

For our 10th wedding anniversary I took my wife on a weeks vacation at a Jamaican resort. We are not uptight with each other. Our second day there we ventured down the beach to a fully nude area. And yes we went all buff. We were both enjoying the sights. Lots of women to look at and my wife got to check out some men. There were 2 specific men that stood out. Both black Jamaican men walking the beach near us. And O-M-G they were definitely proud. I don't think their penis could fit inside a small pair of swim wear. My wife took major notice and when I joked about it, my wife dropped a bomb. She told me she used to be into black men. I never had a clue. Of course I couldn't help but follow up. She explained in college she "sorta" dated a few black guys. Basically it was sex. She couldn't really date the men openly because her family would definitely not approve. I was so turned on thinking about her tiny white self having sex with a black man. I imagined one of the men we saw on the beach trying to fit his enormous cock inside her pussy. I was so horny thinking about it I nearly ripped her clothes off when we got back to the hotel room. The next day I got her back to the nude beach ASAP. It went great, she even let me touch and finger her on the open beach and again the sex was great when we got back to the room. That went on for a couple of days.
Day 5 we were on the beach when three, young black guys walked by, They were maybe 20. Again I saw my wifes reaction. A few minutes later I joked telling her she should have talked to them. Without batting an eye she got up and said "be back in a few". She walked down the beach in the direction of the boys. About 30 minutes later I nearly fainted. She came walking up the beach holding the arm of one of the boys. They walked right past me without even giving a glance. About 10 minutes later she came back alone and sat down. She looked at me with a huge grin on her face. I kept asking what happened and she just kept saying "nothing" and giving me no details. She tortured me for at least 30 minutes when I looked up and the young boy was standing beside us. My wife stood up and again took his arm as she said "meet you back at the room in an hour". I couldn't believe it. I was a horny nervous wreck till there was a knock at the room door. I forgot she was naked and I had the room keys. She walked in still grinning. As the door closed she put her arms around my shoulders and gave me an amazing kiss. She kept teasing me, when I asked what happened, she replied with "what do you think happened". She led me over to the bed, as she stood in front of me she slipped her fingers into her pussy, brought them up and seductively licked them. She laid down on the bed, spread her legs, looked up at me and told me to "taste it and find out". I was so hot I buried my face in her wet pussy. Just for reference I have gone down on her before after sex so I do have an idea of the taste. YES I could taste the cum in her pussy! I had my cock out and inside her in seconds! She made it even better by describing how they went into a the shower stalls on the side of the beach and she braced against the wall as he reamed her pussy with his black cock. I didn't last 2 minutes!!!
Thats just the beginning!

2
# 82904 - by Husband / September 30, 2025
- My Cheating Heart -
Straight Female / 22

Slept With A Married Actor

I work for a large live arts venue in London. Earlier this summer, we premiered a new show and I really hit it off with one of the actors in the company. He's not super famous or anything so you probably won't have heard of him unless you really know your theatre and TV in the UK. Anyway he's in his early thirties, tall and muscular with broad shoulders. Not to mention very charming. In short, I fancied the pants off him, and I could tell he was interested in me too. I soon found out he was married, so I didn't think anything was going to happen. Not that it would've stopped me, and at the opening night party, it turned out it wasn't going to stop him either. I met his wife for the first time. She was lovely. I spent a lot of the night chatting with her, trying not to let on that I had the biggest crush on her husband. When the free booze ran out at the bar, I went up to our offices to sneak a couple of bottles of wine for us so we could carry on drinking. He offered to come with me to "give me a hand." We were chatting and laughing as usual, but once we were alone in the office, now several drinks in, things took a turn. One second, we were looking into each other's eyes, the next, he'd grabbed my waist and pulled me into him. We made out passionately as his ran his hands all over me, and told me how sexy I was. I think he'd have fucked me there and then, but I reminded him that someone could walk in at any moment. We reluctantly broke apart and went back downstairs. I felt so naughty as I handed his wife a fresh glass of wine, knowing that her husband had just had his tongue down my throat. An hour or so later and things started to wind down. Some of the cast were going onto an after party but I could see that she was ready to head home. He said he was going to join them for a bit, but that he'd book an Uber for her. Smooth. As soon as she'd left, he discreetly put his hand on my arse and asked if I wanted to get out of there. Pretty soon we were bailing on the after party and heading back to my place on the tube. The sex was phenomenal. He was great in bed, and explored every inch of my body with his hands, mouth and tongue until I was soaking wet and ready for him to take me. I lost count of the amount of times I came in the two hours we spent ravishing each other. It was such a turn on, knowing that this hot, older married guy had lied to his wife, just so he could shag me. I was utterly spent and blissed out by the time he snuck off home. I don't think either of us felt particularly guilty. I know it was a bad thing to do, but it was also a lot of fun. Plus it was just a one-off and his wife has no idea, so as far as I'm concerned, there was no real harm done. If I've learnt anything in life, it's that when it comes to sex, humans just aren't wired for monogamy.

6
# 82913 - by 3lish4 / September 30, 2025
- My Spouse -
Straight Male / 26

My Friends Dick Pic

My wife liked to look at my friends dick pic while I go down on her. It's a lot bigger than mine and she gets off quickly. Now it's progressed, she has me almost fisting her as she gets off.
Now she wants the real thing.

1
# 82848 - by Gill / September 28, 2025
- Embarrassing Moments -
Straight Female / 35

Not The Vacuum Cleaner

Many years ago I was still in college and made a little money on the side by house sitting or pet sitting. It was usually for one of my professors and their spouse while on vacation. I was pretty responsible and didn’t have parties or anything so I got other house-sitting opportunities too.

One time while house-sitting I had accidentally knocked over a small cactus house plant and there was sand everywhere on the carpet. I searched for the vacuum which was not where I expected but instead in an upstairs utility closet near the master bedroom. I cleaned up the sand and when I went to return the vacuum to the closet I noticed something with a blanket dr**ed iver it. Curiosity got the better of me so I peeked under the blanked and was surprised to see what I’ll simply call a sex machine. It was a motorized box with a steel rod stickibg out and a dildo at the end of it.

I’ll admit I was very curious. I’m not a snooper and never looked around their private spaces, but this cat was sort of out of the bag. I put it on the floor in the hallway, plugged it in, and flipped the switch. Sure enough it started very slowly moving back and forth. A dial controlled the speed.

Honestly I had never seen anything like this before and I was intrigued and kind of turned on. I decided what the hell. I pulled down my jeans and panties, got down on all fours, wetted the dildo and myself with some saliva, and flipped the switch. I backed up a bit and the dildo very slowly moved in and out of my pussy and felt very very good. I increased the speed bit by bit and before long found myself moaning with pleasure and extremely wet. It didn’t take long before I got off with a nice orgasm.

I probably used that machine 2-3 times a day for 4 more days till they got home. Honestly, I loved it and couldn’t get enough. Naturally I cleaned it up and put it back as I found it. They returned home as scheduled and I asked about their trip and they asked about the house. Naturally I told them everything was fine and mentioned the cactus since it was obviously missing a fair amout of sand. They said no worries and asked if I found the vacuum in the garage. I hesitated then lied “yes” and they paid me and we said our goodbyes.

Maybe 4 months later they asked me to housesit again when they went away for the weekend. Of course I said yes and was excited. When I arrived they were ready to leave and as they headed out the door the wife (my professor) popped her head back in and whispered without her husband hearing and said “Oh sweetie, by the way, I left the machine in your guest room set on high the way you apparently like it. Have fun”. Then she winked, closed the door and they left. I was so embarrassed!

But naturally I used the machine all weekend and when they came home it was incredibly awkward and embarrassing, but I realized he didn’t know, only she did. From that day forward, she would occasionally invite me over for what she called “fun night”if her husband was out. Fun night meant wine and the sex machine, but she also became the one and only lesbian lover I ever had..….for the rest of my senior year.

1
# 82872 - by Chrissy / September 29, 2025
- My Spouse -
Bi-Sexual Female / 40

Cuckold, Hotwifing, Open Marriage

I'm lucky, in my opinion, my husband is very open minded. He allows me to be very.... free, sexually. It is a trade off, maybe partnership is a better description. I enjoy the romantic, call it fantasy of finding or experiencing that euphoria of a first date, first connection and first kiss. And who am i kidding the first time i get a hold of a stranger's cock. Mmmmm. If i had it my way, I would be free to go on a couple dates with anyone i choose and fuck them and even spend the night. I love passionate morning sex after getting pounded the night before.

My husband prefers we meet one or two guys, he doesn't care if they come to our hotel room and find me naked ready to pull out their cocks. He wants new guys each time. Black guys are at the top of his list. He cares about the size of their dicks much more than I do. I'm most excited when i find an Attractive, young guy, an older businessman wearing a suit with his cock online clearly in view and sometimes a buff guy with tats. Maybe due to black guys being the most common when my hubby picks. That's not really an attribute I seek out. If I see a black guy that turns me on, of course. My husband will often put BBC as the primary search.

That was a lot, much more than I anticipated in just the back story. I was going to use this as a complaint session with hopes of feedback from women with similar experiences.

Where I end up is being very..... slutty to fulfill my husband's needs as a cuckold. And then hoping the trade off is, I get to enjoy the things that i truly like fun time to time. To backup just a bit. I love getting fucked, i prefer really kinky with one guy and my hubby, but I love DP getting flipped over missionary and getting my ass pounded after two guys have used my body. Orgazmic inducing squirt fest for me. Dirty girl cum whore has its place as well. But I really like the power of fucking my friend's husbands, using sex as a power move with married co-workers and the ultimate thing I enjoy is just meeting someone, strike up a physical relationship. One day or a few months. Example, I met an Uber driver. I might have put on a show for him in the back seat. I was like "Oh my gosh, no is an exceptable answer. Would you mind if i change my top in the backseat?" He said yes, and I i fumbled around topless his eyes locked on my beasts as I tried to remove the tags from my blouse. We stopped for lunch, I kissed him and got in the front seat. I asked for One more detour through the park and i sucked his cock as we drove. He dropped me off at my house. I mean he had the address anyway. I told him "I'm a cheater, please don't judge or show up un-announced." We met 2 more times and it was over, for now. Some guys go away for a while and then reach out when they need to. For the most part, the sex I choose is more romantic, I don't share details or in the case of the Uber driver, I didn't tell hubby.
When hubby picks his cock is locked up, he might have a buttplug in. Wearing panties and we are laughing at him and the size of his "tiny" cock.

An I a one off or are other couples like us?

2
# 82876 - by Lee / September 29, 2025
- Women Only -
Straight Female / 45

Our Visit To A Close Friend

I'm not sure where to correctly post this, however it is something that I experienced so I will post in Women, even though it could go to other topics. Just this past weekend, my husband and I flew to visit a longtime friend at her home. She is widowed and hasn't been with anyone since her longtime husband passed away nearly 5 years ago. I grew up with her, and husband has known her for more than 20 years. We all know each other well.

The first day of the visit we were out to a nice dinner, and somehow the topic of her social life came up. She said that she was still so busy with a career that she hasn't been with anyone really since her husband passed away. She was always really popular in college and is still really attractive, I told her so, and we continued to enjoy dinner. Afterward we were at a small bar down the street from her place, which we were staying at with her, and one more cocktail than I needed she said something complimentary regrading my husband when he went to the restroom. I jokingly said maybe I should share him with you! We are not like that and have never done anything like that in our entire relationship. I'm not sure if it was the drinks or me feeling her loneliness, that made me say that, but I did? I thought she would laugh like we always do, and that would be it. Surprisingly she said, "you would do that?" I thought deeply and said, yes if she meant just playing around, but no sex. She smiled and said whatever I was comfortable with.

Husband came back none the wiser and we headed home. It was pretty late at this point, and we retired to our rooms. I told husband what had transpired and knowing what I thought men would say, was a little surprised when he said he wasn't sure, and it could cause problems. I told him I would talk to her about it in depth in the morning. To make a long story short after discussing it with her over coffee in the am, I felt comfortable, and we made plans to do it after dinner that evening. I am not bisexual or anything like that and I'm pretty sure my friend M is the same but that evening we joined her in her large room, and all removed our clothes. She did have a very nice body, for someone our age, and we all were on her bed talking and she was rubbing her hands over my husband's body as we sat and laid there. I watched her hand rubbing closer and closer to Hubbys semi hard shaft and I leaned over to kiss him while she slowly began to stroke him.

I'm not a super possessive person but I figured I might have a huge issue with this, but watching her nipples grow erect as she was touching him, I was actually aroused at this sight? This went on for a short time, and at one point he was licking me while my friend continued to stroke him while kissing him below his navel. She looked at me as she moved to his now swollen penis somewhat asking is this still ok. I smiled and so did she as she slipped him into her mouth. The most interesting part was still to come. I will continue shortly.

2
# 82880 - by Laura / September 29, 2025
- Embarrassing Moments -
Straight Female / 42

This Is Very Embarrassing

Over Labor Day weekend we took a trip to the beach with another family. Both of us have older children who are friends so they were all with us too.
One morning everyone had gone down to the beach while I stayed behind to clean up from breakfast. When their son who is 19 returned to get his sunglasses he had forgotten we struck up a conversation.
I had just changed into my bikini and it was obvious he was flirting.
I was standing behind the sofa watching the news on tv when he walked up behind me real close kissing me on the neck. I started to move but he pinned me to the back of the sofa.
I had actually been attracted to him so when he kissed me on the neck again I didn’t say anything. Then he ran his hand between my legs and I told him it needed to stop.
Instead I could tell he was getting himself out then he pulled my bikini crotch aside bent me forward and went inside me.
I just said oh my god and relaxed telling him it was ok but asking him to not cum in me because I wasn’t on birth control.
I’d be lying if I said I wasn’t enjoying it but then he shoved deep stopping and I yelled no no no but he finished inside me.
Once he had finished I ran to the bathroom and cleaned up best I could.
I asked him if he would go to a store and get me a plan b. He said he would later when the others wouldn’t suspect anything. That never happened and I didn’t have a chance either.
My period was due on the 17th so I was 12 days late as of yesterday. After my husband went to work this morning I got a pregnancy test which confirmed what I already knew that I’m knocked up.
My husband and I use condoms for birth control so I can’t be one hundred percent certain who the father is but odds are it’s their son’s.
I’ll just have to keep it a secret and hope that nothing happens to expose my infidelity.

4
# 82881 - by Jamie / September 29, 2025
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