Derwood_lolly

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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:

First Date

The first date I had with the woman who would later become my wife was filled with hints of things to come. I invited her to my home and made dinner. Within a couple of hours she sucked my dick and fucked me. She spent the night. She ws very open to sex. She fucked me for the next seven months. And, she knew I was also fucking another woman regularly, but it did not matter to her.

She very much enjoyed sex, but had not experimented much. The early hints about what she might do came to fruition when I set her up to fuck my friend and she agreed. There was no resistance. She let him fuck her. After, she thanked me and said she had loved the experience. I found myself with an erection as she described my friend cumming in her.

It was not long before we were married. During the past year, I have arranged for four different guys to fuck her. Rather than continuing with other guys, I told her to choose one. The guy now has a friend with benefits in my wife. I get off when I fuck her filled with his cum. This has gone on for the past nine months.

I Forgot What I Was Missing

Quick backstory, my husband had 1000 times the sexual experiences than I had when we met. Before we ever got married he convinced me to have more adventures, with men. My first ever threesome, of all flavors as they say. Every mix of letters that includes at least one female. You know mfm,mff, fff. I check women off my sexual list quickly, I did fuck a couple several times, she licked me, but I did it for the dick.

Heading into 2020 I was having sex with other men regularly. I had 2 regular guys that my husband joined in with. One of them filled the Bull role in our cuckold play. My hubby likes pies. You know what I mean. The other was a hot wife kinda thing, hubby and a friend fucked me in all holes, every combination. And then I had Anthony, former professional athlete, a couple years older than me, a wonderful cock. He was my fuck date guy. Although initially we met him and had a threesome, then my hubby just watched me fuck until it turned into, like I said fuck dates. We had dinner, a couple drinks, listened to live music had a slow dance from time to time. He made me feel wanted, hard cock pressing into my body kinda guy. Immune from work, bills, family emergency shit. We would make out in his car, I sucked his cock in our Uber, with permission from a very interested driver BTW.. oh, oh. The driver ended up giving me his number and I fucked him as my husband watched. Anthony was married but he had an unusual job, I’ll leave those details out. He came to a city close to where we live several times a month and he had a hotel room.

I guess I should go back and change “quick” back story. My husband is my best friend. We make love, have passion for each other and we enjoy long lovemaking sessions. Anthony came close, we did kiss, we had sex then would lay naked, have a round 2 or more if I was spending the night. The rest, all the other people I fucked was only sex, sometimes rough, sometimes kinky, sometimes really kinky… lol. Sport fucking.

I’m a RN, we know what happened in 2020. The pause in our society just so happened to take Anthony’s visits away. I met one guy after a 12 hour shift, I met him at his office I sucked his cock and before he fucked me he came. The effort became more than the reward. I settled into lovemaking sessions with my husband. When things got back to normal my husband asked me if I wanted to add another guy to our weekend, I told him not this weekend but maybe next. “Next” weekend turned into 4 years.

Funny how what feels normal, given some time turns into something else. My hubby and I added a few other hobbies coming out of the shutdown. We bought a RV, no upside down pineapple for our doormat. Kayaks e-bikes and other filled our lives instead of extra cocks filling me.

Over the last 18 months or so we talked about adding another guy into the bed. We just never went through with it. Last summer I returned to my home town for my high school reunion. Hubby went with me but he wasn’t bursting with excitement to join the celebration. So after the classmates only social on Friday night, no spouses; he wasn’t too upset when I proposed going to the Saturday night reunion by myself.why the change, I bumped into my HS crush. His wife didn’t come to town and I lied saying I wasn’t sure if my husband would be making it either. We kissed and talked about me staying the night at his hotel room. I was so nervous, so excited, have you ever built something up so much it was setting the stage for a let down? Well, David, my crush drank too much and with all my efforts, he fell asleep on the bed as I stroked and shamelessly took his limp cock in my mouth. Lucky for me, our room was in the same hotel. My walk of shame was two partial hallways and a ride in the elevator.

That kinda what brings me to today, Monday evening. I met a new guy this weekend, like we started this fun my hubby was with me. Designed driver, he set up the guy, the place, the hotel and ran security. It almost didn’t work out, like a lot of times the first guy backed out with 3 hours left before we were to meet at the local casino for a drink. Hubby texted backup guy and he was able to make it, but was going to be a few hours later. I texted him while we were waiting, I went from should I do this to, mmm your cock looks fuckable. After drinks and a few songs from the band we end up in the room. I didn’t wear much, an animal print silk nighty , tucked into blue jeans like a shirt, no bra, no panties. In the room we kissed off came my jeans and my body was his. We were on the couch at this point. I leaned over and sucked his cock, almost forgetting to make eye contact with my husband as Steve’s cock slid past my lips. It came rushing back to me. I sat on his cock and came almost immediately. I asked him to get behind me, he fucked me like he paid for the pussy. We finished missionary kissing and looking into his eyes asking him to fill my married pussy.

This Weekend

I found out five years ago my husband liked the idea of other men fucking me.

After a while I agreed to give it a go, enjoyed it and we have done so ever since. Not all the time but every couple of months as I’m not into having a regular boyfriend or bull as he calls them.

Friday night I had arranged to meet a guy and husband helped me get ready which we both enjoyed.

I met the guy in a nice restaurant but knew he had a hotel room for after. It was fun but the guy was being almost romantic which at first I found funny but then started to get frustrated. I suggested we went back to his room where we had sex.

It was ok but again it felt like he was trying to gently make love to me rather than just have sex.

At home husband was excited to hear how it had gone but because of the guy I didn’t get into telling him with my usual enthusiasm. Husband kissed me and said “you just needed a fuck baby and he didn’t give you that. Will you let me make that right tomorrow?”

Having agreed he told me the following morning to get ready for the afternoon as he had a surprise. He dressed me in black stockings and heels, a tiny red g string and matching semi-bra that showed off my breasts but nothing else. Then he sent a text and told me to go answer the door.

This six foot blonde guy was there and as he stepped in I saw a second dark haired guy behind him, both with big hungry smiles on their faces.

We walked down the hall, with me feeling their eyes on my bare ass, into the lounge where my husband thanked them for coming, asked if they wanted a drink and then said to me “darling these guys will fuck you so hard just as you wanted”.

As he left to get drinks they stepped in, taking turns kiss me and explore my body with their hands. One stepped behind and kissed my neck, reaching around to push my breasts up and out of the bra before rubbing each nipple between his fingers. I heard myself moan as the second pushed his tongue against mine and his finger ran over the outside of my g string and over my rapidly wetting pussy lips.

We stood for a minute until the guy behind gently pushed me down to my knees where I quickly undid the belt of the man in front, pulling his trousers down to free his now rock hard cock which I quickly took into my mouth.

The one behind came to the side, his cock already out and I took it in one hand to wank him whilst I went deeper on the first shaft. At that point husband returned and said “looks like everyone is acquainted” to which I stopped to laughingly say “I don’t actually know your names yet” to the two guys.

The next two hours passed in a blur of sucking, licking, fucking and multiple orgasms. They took me in turns on the sofa, kneeling on the floor and even bending over the dining table.

Husband sat watching but often came to be next to me either holding my hand or moving my hair back from my face.

We did take a five minute break at one point but I was in heaven and quickly started again by sucking both cocks before inviting the first one to fuck me anally. We ended with my riding one guy as the second took me from behind and as I orgasmed all three of us came together before collapsing in a heap across the sofa where husband stood over me to come a second time, his cum shooting across my breasts.

He was right, I really did need a good fucking this weekend.

Husband And My Friend

I sent my husband over to my friends place to help her, I knew she wanted to fuck him but I didn’t mind as long as he was going to do me that same night.
As he started fucking me I said imagine you’re fucking my friend, well his dick was so hard it didn’t take long for him to fill me.
Two weeks later I sent him back to her house to help her, an hour later I turned up nice and quiet and seen him riding her, I took out my phone and recorded it before leaving without being seen.
Later that night as usual I had him on top of me and telling him to fuck her.
As usual he filled me then we went to sleep, two days later I sent the video to my friend and asked did you enjoy it? She didn’t realize I had actually watched them fuck she didn’t know what to say.
When we met I said I don’t mind but you have to get me someone? She said she knew just the right person so the following weekend as he went to help her she sent me my surprise.
He was a younger man quite big and I was hoping he was well endowed, I wasn’t disappointed he was the biggest I’d ever seen and couldn’t wait for him to make love to me.
His name was Ken and had nearly 8 inches which I enjoyed for nearly the whole day until I knew my husband would be home anytime soon.
I arranged to meet him again but not to tell my friend, she asked me how was he I didn’t give anything away saying we went out for some lunch and that was all.
She said I think you need a weekend away so I booked a room in a quiet place and invited my friend. We couldn’t get enough of each other and at some point during the weekend we were going at like rabbits without any protection, in the end he ended up filling me 4 times and I knew exactly what might happen and sure enough I wasn’t disappointed pregnant.
I let my husband fuck me as much as he could so he thought the baby was his.
The biggest twist was that my husband had impregnated her and my lover was her younger brother.
I couldn’t believe how silly I’d been but I couldn’t get enough of him even after I knew I was pregnant.
My husband still doesn’t know he’s not the father, I still send him to my friends house to help her out while I let my friends brother and his friends take me when ever they can.

Julie

Never Forget His Face When I Told Him

We were about five months into our marriage when my husband said he had a question for me but did not want to offend me. I thought he was going to ask about snoring or farting maybe then he asked me about why there was no blood the first time we made love when I told him I was a virgin. I laughed some and answered his question with I was a virgin in the sense of a man having sex with me, told him he was the first man I did anything with, not even second base with anyone. What I did do was a lot of self pleasure and most of the phallic objects around me were not safe, even the top of the bed post on my old foot board was inside me. The look on his face was one of amazement and wonder, he smiled somewhat and asked me what was the largest thing I ever used on myself. I told him next time we were at my mothers house I would show it to him, she had this ceramic sculpture that weighed like twenty pounds and I think it was solid. I told him it was at least a foot tall and no idea how big around but it stretched me out pretty good.

We are at her house like two weeks later and he is looking around the living room then looked back at me pointing to it over on the end table. I slowly nodded up and down, he could not stop thinking about it, told me later on that thing was more than a foot tall and had to be four to five inches thick. He just looked at me and asked if i had the whole thing inside me and I told him I would put it on the floor then squat on it and after several minutes could feel my butt hitting the carpet.

How are you so tight still? he laughed.

Mom’s BF

I’ve had a thing for my mother’s best friend since I was 12. I fantasized about her regularly and masturbated to those fantasies. She was staying with us while major renovations were taking place in her home. She’s a 5’5” 135 lb babe with a C+ cups overflow. My plan was to seduce the woman. I walked around for morning coffees in loose fitting pj bottoms no top. My dick semi hard so she could clearly see its movement as I walked into the kitchen. Oh she noticed. She loves to tan and I loved watching her tan, her even letting me apply lotion to her back. Mom wasn’t around on a couple of occasions and I was lucky enough to crack a boner while covering her back. She saw it clearly pitching a tent, I apologized and she said she was flattered. I told her straight out how much I wanted to lick her pussy. She was shocked at how straight forward I was but after an uncomfortable silence she said, “And if you weren’t your mother’s son, I would let you.” There she was laying on her back and I applied lotion on her upper thighs. She said, “This isn’t right Brad.” I said, “It isn’t wrong” and kept on. I moved her bikini bottoms over exposing her shaved pussy and then put my mouth to her c**t lips. She moaned and said, “This is trouble!” I just kept eating now getting a full face of her after removing her bikini bottoms. It took awhile but I got her having a powerful orgasm. She told me to fill her, to put it in. I did and dropped my load immediately. She’s back home now but I visit often and have regularly fucked and face fucked her to both of our delights. Lucky me. A fantasy cum true.

My Stripper Dreams..

A few years after i became sexually active i started fantasizing about making a living from having sex with strangers. In the beginning i thought it was just a phase, and that it would pass. Today several years later i still have the same fantasy, and it has only gotten stronger.
I think i would make a good sex worker or a stripper, but i have always been too afraid of what my family or friends would think if i ever took the plunge.

When i masturbate by myself i like to record it. I enjoy using dildos and different objects and seeing my own excitement afterward on the recordings..
I would love recording myself getting fucked, but i have never done that. I have not discussed any of this with my bf..

This Is Getting Addictive

If you have read any of my other stories, you will know that I have been married for a long time, but sex had become nonexistent and so I looked to porn and sex ads to fulfill my sexual needs. I finally actually met someone in a vehicle and he fingered me And I have to admit that it felt amazing.
I was a little surprised that I went through with it, but I have to admit that as soon as I got home, I wanted to go do it again. Even though I had crossed the line and let someone finger me. I am still nervous about meeting someone. I talked back-and-forth with quite a few men, but a couple of days ago since I had some time to myself, I decided to meet someone. This time was a little different. The man was about my age and told me that he was going fishing at a friends pond just outside of town. It wasn’t that far out of town, but it was fairly secluded. Obviously, I was nervous about meeting a stranger, but my sexual appetite overruled my nervousness.

I followed the directions and even went through a cattle gate and eventually parked next to a pick up truck by a very pretty pond.

The man, I was meeting, talked a big game and told me that when he was done with me that I would be screaming. To be honest, I thought he was just talking big. I showed up in a sundress with no panties. When I stepped out of my car, he walked up to me and was actually very pleasant and introduced himself. He was probably about 10 years younger than me. We had small talk for about two minutes and finally I just asked him if he wanted to get started. He told me yes and told me that before we get started that I needed to get naked for him. Even though we were in the middle of nowhere, I was a little nervous about that, but I went ahead and took my sundress off. I have to say that standing outside, totally naked, in front of a total stranger really turned me on. And then this nice man and pretty attractive, suddenly became pretty aggressive And demanded that I get on my knees and suck him.

I was obedient, and as soon as I got on my knees, he pulled his pants and underwear down and dangling in front of me was a rather large uncut dick. I had never been with someone with an uncut dick. But as I began to lick and suck him, it grew, and I really struggled with the girth. I was surprised by how aggressive he was, especially in the way that he talked. Even though I was struggling, he seemed to not care and kept pushing my head and making me take more and more of his dick than I thought was possible. I always thought that I did not like that kind of talk, but I found myself getting very turned on. I’m not sure how big he was, but I was surprised by how much of him I could get in my mouth even though I could not get all of him Then he told me to stand up and to face away from him and to put my hands on the tailgate of his truck. I felt him reach behind me and he stuck two fingers inside of me and he commented that I was such a slut to be so wet, and naked in front of a man that I didn’t even know. When I tell you that he fucked my brains out, I am not kidding. He grabbed my hips and immediately stuck that big dick inside of me and it felt amazing immediately. With one hand, he grabbed my shoulder and with his other hand, he began playing with my clits while he was fucking me. I orgasm immediately. But then he slowed down and told me that I needed to brace myself. He said that he was going to fuck me as hard as he could. I already thought that he was fucking me super hard. But he grabbed my hips and fucked me so hard. I promise I almost passed out. It was a little sore and then it felt absolutely amazing and dammit if he wasn’t right, for the first time, I believe I truly screamed.

He pulled out and came on my ass and then told me that I could get dressed.

He pulled his pants back up and I put my dress back on. I walked over to get in my car and before I did, he told me to wait. I turned around and he gave me a huge kiss and we ended up kissing deeply for a few minutes. Then he reached under my address and fingered me extremely hard and yet again I was screaming. He stuck two of his fingers in my mouth so that I could taste myself on him. Then I left.

This kind of thing is getting addictive.

Seconds

This might sound wierd but I love sloppy seconds. Early in our marriage my wife had a fb, a single buddy of mine I have written about before. I worked alot and they had my permission to do what they wanted. Sometimes they had sex at our house when I was asleep but she woke me up after he left and seconds with her pussy full of cum was great. Sometimes she would come home after being with him which was good but not as fresh. We moved on to threesomes with another buddy and going second after watching him unload inside her was even better. One weekend she was with me on a business trip and we hung out that night with a young guy that was working with me, I went to bed but they stayed at the bar. One thing led to another and she went back to his room. She came in a few hours later, climbed in bed and confessed she fucked our young friend twice, he had a big cock and came buckets. I was hard instantly, slid in her stretched pussy full of cum and unloaded in her in no time.

Listening To My Wife Moan

We were still unmarried when my wife was first shared with my best friend. After the first time, he fucked her several times and I gave them privacy to enjoy each other. Not long ago our friend came to visit after we had moved to another city. We had a terrific evening catching up together and then we decided to go to bed. In our bedroom I told my wife she should feel free join our friend in the guest bedroom. I undressed her and she went to him.

She left the door open and it was not long before I could hear her moaning with each thrust into her. She cried out when she came and loudly moaned some more. Her moaning and cries as she was being fucked and having orgasms were absolutely erotic. I would rather hear her enjoying the intense physical pleasure of being fucked by our friend than actually watching her fuck. Hearing her moaning and crying out gives me an a tremendous erection.