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:

Like Mother Like Daughter

I am a single, 27 year old woman who enjoys sex. Apparently, I get this trait from my mother who, after a recent discussion, enjoys sex too.

I have been known as easy or slutty for much of my sexual years. I was always open to sex and very rarely said no to advances of boys. As the years went on, I found my mom to be exhibiting the sexual behavior as me. She and my dad had gotten divorced and she was always going on dates. It did not take much to figure out that she was a slut like me.

So, over coffee, I actually asked her about it. After some initial push back, she acknowledged that since her separation from my dad, she has gone back to her slutty ways. She had the same experiences as me. The same justifications. The same desires.

Wow…just wow!

Swipe Right

I am on a few dating apps as I am now single again. The other night I am going through who has liked me and one guy is my sons best friend. How on earth did this really happen?

I liked him back so we could safely chat on the app. Turns out he has always liked me. When he saw my profile, he decided to do something about it.

We go on a date. It is fun. Food is good. But now what…how do I kiss this guy? He is my sons friend. I tell him all of this and he literally grabs my head and kisses me. I was shaking from the embarrassment of this. It did not take long for his hands find every part of me. My hands tried to keep up, but he had found my pussy and I had lost. This man, who is half my age, fingered me in the dark parking lot of the restaurant until I came. He held me up and told me to follow him where he drove. I did and we ended up at a motel.

As soon as we got in the room, we both stripped naked and fucked like crazy. We spent two hours in the room and then went our separate ways.

The next day, my son screams at me ‘mom, why did you fuck Darren?’ Knowing not to lie, I said because we met on a dating app…blah blah blah.

But mom, I have pictures of you and a video of you getting fucked doggie style.

…..I did not know he had filmed me.

So fucking embarrassing!

I Want My Best Friend To Sleep With My Wife

For many years now, I've shared nude pics and vids of my wife with my best friend. He loves her body and is very turned on by her. I desperately want to watch the two of them have sex together but I don't think my wife would be into having sex outside of our marriage. Just needed to get this off my chest!

Breast Feeding Got Us Started

Me Tami and my husband Tony got married during our young 20’s. My sister Lori is 2 years older and married to Keith. They got married her senior year due to pregnancy. They had their second son two years later. They are fixed so no more babies. After Tony and I were married several months we decided to start our family. My sister and I have always been special close as also our spouses. We had a daughter and we’re so proud.
Loti and Keith were over one evening. Their sons were with grandparents so the three of them were drinking beer, I couldn’t because I was breast feeding. My daughter got full and went asleep and Lori was holding her. I mentioned I was going to go pump breast to relieve the pressure. Lori said let Keith do it, he loves breast milk. I laughed and said when Tony tried it he thru up all over the bed room. Not Keith she assured he loves it. I called her bluff and pulled my breast out. Keith asked Tony if he was ok with this and Tony said go for it. My breast aren’t as big as my sister’s so he got the easy fast milk quick. Lori gave me our daughter back and took Keith by the hand and said we are going home so she could drain him now. Tony and I-went to bed and had one of the most erotic sex events we ever had.
This started a different approach to our sex life. We lived side by side on family property. Keith came over almost daily to suck my breast. We always shared this with our spouses and they weren’t offended. One day when Keith came over my daughter was napping. I sat on the couch and unbuttoned both side of maternity bra and Keith started his thing. Only this time he put his hand between my legs. He skillfully frigged me. I was almost to orgasm when I asked him to stop. I asked him to stop again but he didn’t. He then stopped and pulled off his shorts and briefs. He told me to sit on his lap and hunch on him while he sucked my breast. And no time I had him inside me. We were full scale fing now. We both finished and had to rest. I felt very quilty. I asked Lori to come over after her work which she did. I told her what had happened. She told me Keith had called and told her. She came over and gave me a hug and said she hoped I enjoy fing Keith as much as she does. Tony was troubled some when I told him. He said he didn’t want me to get pregnant by him. I hadn’t considered that. He then asked if Lori and him wanted to have sex would it be ok and I agreed. I didn’t get pregnant by Keith and was relieved.
Keith and I didn’t have unprotected sex until Tony got me pregnant again. I had Keith going with breast feeding again. Keith isn’t as endowed as my husband but is a good experience. I have tubes tied now so no more babies. By our late 40’s Keith was getting overweight and us didn’t crave sex as much. Now Tony and Lori are still active. Lori gets sex with Tony probably 2 time to my one. My husband is very good looking and very fit physically. It is like he keeps Lori and I sexually satisfied. My husband has sex with one of us at least every day. I have slight concerns at times but I know I’m number one to Tony and he enjoys my body. Our children are out of the house now. We go on mini vacations together. Thanks to the blue pill we can get Keith going good at times. As far as anyone knows we are a normal loving sibling families. I can tell my sister only wants sex with Tony but is very loving to Keith when he can crank up. My husband has used the blue pill some but doesn’t need it to get erect. I wake up early to drain Tony before he goes to work. Then I go to work later. Not every morning but enjoy being at work after sex that morning. Tony goes to their house late night after Keith goes asleep and they have sex in there guest room. This arrangement has worked so far but has had some issues from time to time. Keith feels inadequate now but we all hold his ego up.

Caught My Girlfriend And Her Mom With Her Brothers Friend

My girlfriend and I have been dating for 5 years. We are both 24 and have had a great relationship and sex life. I never suspected her of cheating until I caught her this past Saturday night.

I was supposed to meet her at like 8 pm to go out to dinner but I ended up getting off at 6 so decided to surprise her by coming over early. She still lives with her parents as do I. So I go over to her parents house and let myself in. Her dad and brother I knew were away camping for the weekend.

I go up the stairs and don’t see anyone in the kitchen. That’s when I hear noises coming from her parents bedroom
And they were def sexual noises. I was confused as I knew her dad wasn’t home so I was like no way is her mom fucking someone else

I look outside and don’t see anyone either so I slowly go back to the bedroom and the door is halfway open. I look in and I’m totally stunned at what I see.
3 people are totally butt naked. My girlfriend her mom and her brothers black friend who lives down the street. I met him a few times. His name is Mike and he played football with her brother. Well built linebacker type guy who has been a friend of her family for many years. I guess way more friendly than I ever imagined.

My girlfriend is bouncing up and down on his big dick hard and fast riding him. Her mom is sitting on his face and getting her pussy eaten out. It definitely looked like this wasn’t the first time and may have been a regular thing for them. I’m sure her brother and dad have absolutely no clue or they would lose their shit.

I watch for a few mins. My girlfriend rides him until she cums and then her mom and her switch places. She bounces on his bbc and my girlfriend has him eat her out as she grinds her pussy into his face. I of course have seen my girlfriend naked many times so I was pretty focused on the mom and her hot body. She is 48 and still looks great. Her mom rides him until she cums and then makes him cum in her pussy. Just crazy shit.

I get out of there before they see me and am still trying to figure out what to do.

Will My Online Print Ever Fade.

I am older and wiser and a mom onf 2 kids now with a baby daddy. But when I was young like 19-23 I did a pile of Webcaming and even tried escorting a bit.
I don't regret it because I had fun and made money but when Google right I noticed pics and vids of me are still out there despite me canceling all my accounts years ago. You have to dig hard to find me but I am worried they will never go away.
I don't want my kids to ever see me like that or be bullied if other find them. There are still nudes of me and clips of me doing sexual acts both with toys and people. There is even an really old ad of me as an escort from years ago when I was 19 and I can't get itubfsssw down because the site seems abandoned.
I am frustrated and honestly embarrassed. What to you think the odds of being found out are?

I Used A Vibrator While Driving

I had a 5 hour drive home after spending the weekend with family. Usually I just put on a podcast or listen to music on the way back, but I got bored of both by this point. I had made several drives in the past month I was just tired of the same stuff. I let my mind wander and I thought about how exciting it might be to use a vibrator while driving. It was risky, but so tempting.

I eventually pulled over by a gas station to look up where the nearest sex store was. There were none around but there was a supermarket relatively close that had a vibrator. Of course I drove my horny ass there and bought it. I was nervous at first, given that I was driving, but I did it anyways.

It was so exciting, I was grinding my hips in my seat with the vibrator rubbing on my clit in my underwear. I thought about how I should have bought something else to go inside me. But the vibrator was enough. I won't lie, my driving got a little... questionable. It felt so dirty but in a good way, driving by big semis knowing they might see me squirming. And trust me, nothing is more exciting than cumming while going 80mph. Definitely was a fun drive home LMAO

Blowing My Hot Neighbor With My Two Friends

This happened the middle of last week. Somehow me and my two friends. All mid -late 30s moms didn’t have to deal with our kids on the same day. My husband was at work and my kids were with my parents for the day going down to the city. It was great and we all texted each other and I invited them to my pool as it was a very hot day. We were all just giddy to have free time and started to drink and chat about our kids and husbands while we sunbathed in our bikinis.

I’d say about two hours later my new neighbor comes out of his house and sees us all in the pool. He is a mid 20s single guy. Average face but super muscular guy. He isn’t ripped but looks like a power lifter. Huge arms shoulders chest and even his lower body legs and butt are all incredibly muscular.
He is also a flirt and of course came over to flirt with us. We were all pretty tipsy and my one friend asked why I didn’t mention my new young stud neighbor. I giggled.

So he came over and asked if he could take a dip with us in the pool. I said sure and he removed his shirt and shorts. He was just wearing some tight boxer briefs and you could see what he was packing. His dick most definitely matched the rest of his large frame. We were all checking him out and he knew it. I then asked him if he was going to be swimming in his boxers and he said no he likes to go nude and he slipped them off and paraded around the pool deck butt ass naked. His cock soft was larger than all our husbands large. He knew what he was doing and then jumped into the water.

He played around with us for a bit. Splashing us and picking us up and throwing us in the water. We played back and jumped on him etc etc. he had incredible strength and you could feel it when grabbing him. His dick also ACCIDENTALLY touched us a few times. It was hard to avoid anyway haha.

after a bit I told him he would need to leave as my husband was due to be home in like 40 mins. He kinda pouted and got up on the edge of the pool and sat there with his dick hanging down. We all were just staring and he flat out asked if any of us had seen one so big. We of course said no and he laughed and said you should see it hard. He started to masturbate in front of us and we didn’t protest just mesmerized by how big he grew.

We totally knew what he was doing but none of us married moms told him to stop. He then got back in the water with his hard on sticking out and said it was free to be touched. He kinda laughed but also looked serious.

My one friend def had more alcohol than me and she just reached out to stroke him. She laughed and said we should give it a try. So I reached down and stroked him for a minute and then my other friend did too. We all were like little school girls giggling the whole time and telling him how huge it was. He then said we were all so sexy and being teases and that he needed to cum being around such hot older ladies.

My drunk friend told him to go sit on the pool edge and she went over with him and started to blow him right in front of us. We were stunned and watched for a minute. She was struggling though and told us he was so much bigger than her husband that she needed some help. I guess it was the alcohol the peer pressure and his hot body but we both went over and started to work on his dick with her.

My friends alternated sucking and licking his shaft and head while I mostly paid attention to his balls before switching to suck his head. I was surprised he lasted as long as he did and he removed all of our tops to expose our tits to him. He played with each of our tits for a bit before he started to breathe heavily. I could feel his shaft start to spasm before I pull off his cock head and he sprayed our tits with a very large load of cum. He had 4-5 really large spurts that covered my tits in a glaze. My friends didn’t get as much as he focused his load on me. It was super hot and def an afternoon for us to remember.

Now I’m not going to lie and say that was the only time I met with him since last week. My friends said I should make him my boy toy next door and on Sunday while my husband took the kids to his parents I went over to see if he was home. He was and I asked him if he had thought about his time with me and my friends. He of course said yes and I got on my knees to suck him hard. It was def a challenge doing it by myself but I got him hard and then he fucked the shit out of me for 2 hours all over his house. I’m only 5ft 3 and 115 so he had no problem picking me up and using my how he wanted. I’ll def share that experience in detail another day

Cucked Husband

For at least five years my husband (Andy) has asked me to cuck him. For five years there was never a chance of me allowing this to happen.

Two weeks ago we went out with some friends. As the night wore on, my husband kept pestering me about this being a good night to cuck him. He said he had the perfect guy. Enter Mark.

Mark joins us. He is a coworker of Andy and is built like a Mack truck. 6’3, fit like nobody’s business, a smile to die for and a voice of a drill sergeant. The problem…he was black. This would be VERY new to me if this were the guy.

From the moment he started talking to me, I knew he only had one thing on his mind - to fuck me tonight. He was flirty, sexy, convincing and that voice - I felt like I needed to listen to him or something bad would happen.

I pulled Andy aside, told him my thoughts and he lit up like a kid a candy store. I asked him multiple times if he really wanted this. He told me over and over that he has waited for this. We returned to Mark and we decided to find a hotel room.

I rode with Mark to the hotel and his hand was in my pants the entire time. By the time we got to the hotel, I was soaked. As Andy paid for the room, Mark was kissing and touching me like he and I were the couple. It was odd feeling but I was so horny.

In the elevator, Mark tells Andy that he is going to fuck me like never before. His hand still in my pants…my sloppy pussy in heat, I look for Andy to approve this and he nods.

Mark fireman carried me to the room, tosses me on the bed and pounces on me. Within seconds, he was in my pants. Within a minute, he had fed me his black dick. It barely fit in my mouth but I wanted all of it. After some head, he spins me around and slams his tongue on my clit and I started to cum. Immediately! Hard! Deep!

‘Yeah, now you are ready! Get on my dick and show your husband how you act when in the presence of a hard black dick.’ I climbed on, dropped my hips, let out a distinctly erotic moan and started to bounce. Marks dick plundered my white pussy with each movement. He encouraged more from me. Faster, bounce harder, go deeper. That voice!!! Fucking voice!!!

He basically fucked me for two hours. He came twice and I came (a hundred times I think!) We went our separate ways at the end of of the night.

Mark wants more. Andy wants more. I am finally recovered from the intense fucking from two weeks ago. I want more but I am afraid of this being a thing and not just living out a fantasy for Andy. Such a dilemma.

Hooked And Suspended

A few weeks ago, I was getting fucked senseless by my Bull when he lifts me up, hooks me on his fat black cock and proceeds to fucked me while I am hanging on to him. This was a first for me as I am a curvy girl. Not huge, but not small either. He literally had his cock in my pussy and my legs hooked on his arms and he plowed me. My boyfriend, who was being cucked at the time, was speechless. This has occurred a few times now and each time I feel like I am going to squirt and or he will cum inside of me. I am nervous but it makes my pussy burn like crazy!