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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 / 28

Bros Old Friends

Went to a Bbq Friday night at a buddies house from work. His neighbors where there guys firm work and their wives. I’m currently single and came solo. I can usually find some divorced women or unhappy wife that I can fuck around with at these places. I’m a good looking guy really good shape type. One of the couples there’s where this guy Mike and his wife Maria. They are in there early 40s. We start to talk and Maria by far is not the prettiest girl there but is super cute. We talk her husband and I then her throughout the evening. None of us are buzzed just sipping on a drink and getting along. Maria had light brown hair with a few blond streaks she had denim short shorts on and a shirt that fit snug. She has a soft midsection I would call her thick but in a good sexy way. Mike was almost bald and what hair that was left was white. The party’s were on the levee so we could see the fireworks. Problem was the party started at 4 and it was still daylight and most people were smashed. Out of nowhere Mike asked me if I was related to so and so and I said that yes he was my older brother who had passed away during Covid. They apologized and Mike went to grab us another drink. When he walked away Maria gave me a hug and it lingered it was starting to get dark and I gave her little ass a squeeze. She left my hand back there staying really close to me. Mike came back and saw us and just smiled and said ok I’m going to go on the levee. Il check on you in a bit. She smiled and let me in on there little secret. He is ok with her having a little fun and likes to you know. I told her I’d fuck her but wanted nothing to do with him. She laughed and said not watch juts watch. That was all I needed she pulled me over to there place and went upstairs to a room. There was a slider so we could watch the fireworks. It was great I got to fuck this little thick Latina while watching illegal fireworks explode. While hammering her on all 4s I slid my thumb in her ass and she kept going. I felt her shake and be loud as she got hit with a Big O. She let out a fuck that last one of the best fucks damn juts then I slid my dick right into her ass. Very large gasp and I didn’t last blew my load while i bottomed out in her ass. We laid in her bed watching the fireworks and went back at. We never went back to the party and fell asleep. Next morning was very awkward as I woke up to a bj and one more round. She put her number in my phone and mine in hers and said she would be calling me in the next few days. Mike was down stairs and said not one world to me as I was headed out. All I heard when I walked out was why did you lock the fucking bedroom door.Il update on that argument she text me last night that she was going to run errands Saturday morning while Mike golfed out of town. She sent me a pic of her chubby ass with a butt plug.

0
# 80321 - by TonyB / July 5, 2025
- My Cheating Heart -
Straight Female / 42

I Wanted It

I did something that if you knew me would not believe I did it.

I’m married stay at home mom of 3 good wife and mother. Husband makes plenty of money so I stay home nice house fancy SUV very happy but at times I feel like I’m stuck in a rut. It gets old I do fantasize about sex with other but never act on it. My husband is good in bed but besides my first time have never been with any one else. My husband has a few friends that make comments and if I let them would absolutely fuck me. While at times I think that would be fun it would destroy my husband and I could not do that. I’m into tennis but would never think about the club and hooking up. It happens all the time and everyone knows who banging who. I thought it was just a fantasy and never would do anything. That was until my husband was invited to a hallowed party that a friend of a friend is his throws and is kind of wild. He asked if I was interested in going he said the women dressed provocative but classy. I thought about it and figured I could dress slutty and get away from my boring life for a night. Why not so I said ok it might be fun maybe we can go for a little bit.

He dressed up as a football player jersey and pants and I went as a cheerleader. My top was fitted tight revealing a lot of cleavage. I’m a solid D cup 5 foot 4 140lbs curvy dirty blond hair naturally a brunette but dye it blond. When it’s close to having my hair done and the dark roots show my husband at times says it has a slutty look. I purposely postponed my appointment for a week after the party. My skirt was right firm the costume store so the bottom part of my ass cheeks where hanging out. It came with white huggers which are boy shorts but I took a chance and since I’m short and it was going to be dark I wore a white thong. Husband liked it he was ok with it so I said fuck it. Sitter came we head out tell the sitter we would be back late she was planning on spend the night so we are good. We arrived it was a big house party was in the front yard in the house upstairs in the huge backyard. My husband says let’s walk and checkout the house and party. He then says if we get split up and can’t find each other for more then 20 minutes we can meet up at the large statue in the front of the house. He had my phone as I had no place to put it.

Lots of women were half naked and my costume is tame compared to some these girls are wearing. I see all kinds of good looking guys and am squeezing through a path way when my husband ran into a few of his friends. They say hi and continue to talk. I did not know anyone there but told my husband I was going to grab a drink. He said ok.

I got back and he was gone. I couldn’t call him he had my phone so I went back to where we supposed to meet and waited. Sat down and had my drink. This really muscles on muscles Mexican guy dressed as Zorro came up and chatted me up. The way I was standing I didn’t realize was a straight shot up my skirt. I was leaning on the statue and my skirt was lifting. He got me another drink his friend brought us a drink. We sat and chatted for almost and hour and hubby was no where to be found. He flirted and I flirted we drank and he asked me to dance. Sure why not fuck it. Took me over to where there was an open spot and we danced. There were lots of people, the drinks were hitting hard and I could feel his hands on my bare ass a few times. It felt good to be honest still hubby no where to be found. I got his name out of him Ramiro or something like that. His shirt was unbuttoned looked like he was in his mid twenties and for days. Took me by the hand to check out the back yard. I mentioned over and over that I was looking for my husband. He said he would help me find him. Walked me around and around and we found ourselves outside with 2 of his friends. There was a large shop that looked like there was a race car in there. Before I knew it I was kissing him and out loud I kept saying while drunk that this was a fantasy of mine. Big mistake because while his friend looked out I was getting fucked bent over the race car. My tits where pulled out. I pushed back and let him hammer away. He filled me up then his friend switched spots and had me as well. I’m not sure how long we where back there but I know that each one came in my pussy and ass once. In the scuffle to fuck me my panties where torn so I had to go completely commando. I was wiped and they at least cleaned me up. I fixed my makeup and he asked for my phone but my husband had it. His friend walked out first and looked out while I made my way out. A few people saw me as I scurried off then Ramiro walked out. I went to the bathroom cleaned up more then went back to the damn statue. Finally my husband shows up and he is drunk. I got him and left. I thought about finding the 2 and exchange numbers but thought to myself ...just drive off Kelly, you got your fantasy fuck and it was amazing. Maybe again next year.

2
# 80322 - by Kellyfun / July 5, 2025
- My Cheating Heart -
Straight Female / 32

Cheating On My Friend With Her Husband

I went to a pool party off some friends. When I borrowed a room to change the husband walked in on me, and I took the towel to cover up. He closed the door and motioned for me to drop the towel. He had sex with me on the bed.

It was that easy to cheat on my friend with her husband.

2
# 80330 - by Karen / July 5, 2025
- True Sex Confessions -
Straight Male / 23

I Let My Girlfriend Lose Her Virginity To Someone Else

A while ago I started dating a girl who was a complete virgin. I was her first boyfriend. She was just discovering things with me. But there was a big problem: my dick is too small. She was always curious about having sex with me, but I was always reluctant because of my size. Time went by and she wanted to have her first time and I always tried to satisfy her with oral sex, which worked to a certain extent. She loved it when I sucked her pussy and played with her when we could get caught. But it wasn't enough anymore.

One time we ended up traveling to the beach and we had a mutual friend who she seemed to have a certain interest in. In the first few days she seemed to be more excited than usual, especially when she was around this friend of ours. At night we would have oral sex and she would tell me she wanted me to fuck her, but I could never go any further. She was unsatisfied, saying she wanted to have her first time. Deep down I was horny and ended up asking her if she would like a man like our friend to fuck her.

She was reluctant at first, but I could tell she was really turned on by the idea. I started jerking off while we were talking and she confessed that she would like to fuck him, if that was the case, after all, she was dying to have her first time. I told her that I would accept her having her first time with someone else, as long as she was satisfied with it. She was reluctant, but I insisted and told her to make plans for her to go to his room the next day and go after him, without confessing that we had made plans, while I would watch from behind the door.

The next day, we spent the day normally until it got dark and I was nervous. When it got close to dawn, she kissed me and said she was going to his room. I could tell she was in the mood, wearing a T-shirt, no bra underneath and leopard-print panties. I remember it very well. I waited in my room, anxious to see what was going on between the two of them. After 15 minutes I ended up going towards the room where he was, being careful not to make any noise. In the hallway, I could already hear the sound of the bed moving, and I felt a mix of jealousy and arousal. The door was half open and I started to watch them from afar.

I was surprised by the scene I was seeing. My girlfriend, so innocent, kissing another guy so intensely. He was shirtless, in his underwear while she was still dressed, sitting on top of him, kissing him while they rubbed against each other. It didn't take long for him to take off her shirt and suck her breasts. I could see her moaning from afar, crazy with desire. He laid her down next to him and started to take off his underwear and I soon saw that his dick was hard and big. My heart raced and I wondered if I should intervene before things happened. My girlfriend, lying next to him, started to grab his dick and jerk off, without any shame. Her firm hand, holding another dick, drove me crazy. At that moment I started jerking off too.

It wasn't long before I saw her sucking his cock, licking it as if she had never sucked a cock before, while he moaned with pleasure. She had barely sucked mine, I hardly ever let anyone be embarrassed. Seeing her like that made me cum and I ended up wiping my cum on my underwear. She got up and took off her panties, which were probably soaked. I couldn't believe she was really going to lose her virginity to another guy. She got on top of him, while he was lying down, and started to sit on his cock. Without any protection. At that moment I went crazy. I was watching my girlfriend, innocent and sweet, sitting on another guy's cock, who was taking advantage of the situation, fucking a virgin girl without knowing it was his first. I realized she was totally in ecstasy, moaning shamelessly, sitting on his cock with desire. My cock hardened again and I started to jerk off again. I had never seen her having so much pleasure as in that moment.

They changed positions and he got her on all fours, while he fucked her hard. She was moaning with pleasure and was probably having an orgasm. He was slapping her ass while he fucked her. He was completely dominating her. At that moment I came again and my underwear was completely wet. It wasn't long before he ended up cumming, I didn't see where, but probably in her ass. I ran back to the room where I was and waited for her to come back. I had just witnessed my girlfriend lose her virginity to another guy. Something indescribable that happened to me.

0
# 80264 - by Boyt2020 / July 2, 2025
- My Family -
Straight Male / 34

She's Now Happy Again.

I inherited a very small dick from my father who i learned also have a small piece based on a conversation i had with my mother. I figured my mom didn't have a problem with dad but i wish i could say the same thing about my wife who is not aware that i know it's my small dick that bothers her which lead to us arguing almost every day for the simplest of reasons.

She told me once that she hate having sex with me but she didn't gave me a reason why but i know it was my small dick that bothers her. Now let me be frank and say, it bothers me too. I am ashame of my small penis and i cannot do anything about it, especially to a point where it cannot satisfy my wife and now she's frustrated. One day she asked me if i'm into kinky sex and i asked her to explain what she meant ? She then showed me a picture of a very huge black dildo and i said 'no way'! But since that day i''ve been watching her.

Everything changed one weekend when a friend of mine stop by to sign some papers to close off a business deal for the company we work for. When he stop by i noticed my wife behavior have changed a bit from her usual self. She literally forced him to stay for dinner and before you know it we were all drinking red wine. He and i were very good friends before we started working together and i know him to be very flirtatious and here is my wife actually doing the same thing right in front of me. I wanted to end the evening by saying good bye to him but she kept pushing him to hang on a bit, then we all ended up in our pool. Her nipple got stiff instantly and her smiles were like never ending. My friend who just stop by to sign some papers are now spending the entire evening with us and is about to spend the night. Now that makes me very uncomfortable.

I started to see exactly where she was going with it but i didn't know to what extent. I then decided to watch her very closely. We then hit the shower one after the other where my friend was invited to go first and my wife went after. When i went in and came back out i nearly drop dead when i saw what my wife had on and my friend was right there. She didn't have on any panties and her night wear were a little to short for us to have a male visitor in our house.

We played a quick game of cards and started another round of drinking and that tipped the scale to a level i never dreamt of. My wife came and sat in my lap while we play cards and she started acting not only strange but horny. I then whispered in her ears and asked her what is it that she's up to?... then she asked to be excused and pull me inside the kitchen.

She told me she was just having fun and she didn't want the night to end. I blurted 'you want to fuck him do you '?..But she didn't answer. We argued a bit then we called it a night and went into our room. In bed, she twisted and turn like someone being tormented. I then slipped my finger inside her and were surprised how wet she were . I asked her the same question again but this time i took her silence as a consent . I did not know what to do next, so i said 'damn it! and got up and went for my friend in our guess room. He were a little hesitant to follow me when i told him what it was about but he came along. When we went in she had the pillow over her face and her legs were spread wide apart. I nod him to go for it and he went and started eating her out to some loud moaning. She must have known who had entered her from what i saw pushing inside her. His cock were 4 times the size of mine. He fucked my wife the entire night and into the wee hours of the morning. She didn't even look at me for a single moment that night until he had left the next day then she sucked my dick. From that day forward she were like the happiest woman alive. And incase you all are wondering, well 'yes' my friend have fucked my wife more than i did in a single year. She got addicted to his huge cock which even surprised me as to how can a cock be so damn big.

9
# 80266 - by George / July 2, 2025
- My Cheating Heart -
Bi-Sexual Female / 36

Anonymous On A Business Trip

I am a 36 year old married woman, 2 young kids. I have a great job that allows me to travel for work a couple times per year. I have a fantastic life, but a naughty secret. I am a slut. I always have been, but I’ve been unable to stop… maybe I don’t want to.

I went on a trip this past spring, and I had every intention to have some fun while I was away from home for the week. And that I did… a few people actually. But this is about one in particular.

I was on a popular kink site that I frequent.. browsing the local profiles. I got a message from a man and we began to chat a little bit. He was very direct in what he was looking for. He was much older, in his early 60’s. His profile had only a couple dick pics, and mine shows a few of my breasts and ass. Something about him piqued my interest, so I proposed an idea for some anonymous fun at my hotel. He was happy to oblige.

I gave him my hotel and told him to message when he got there. I cleaned up and got ready. He messaged when he arrived, and I gave him the room number. I left the door open on the security latch, turned out the lights aside from the bathroom light so that it wouldn’t be pitch black.. I was already naked, and I got on the bed on my knees with my ass in the air and I waited. I was facing away from the door so we wouldn’t see each others faces.

He came in the barely lit room and closed the door. He didn’t say a word as he came up behind me but I could hear him taking his clothes off. Then complete silence before a hard slap across my big ass. I screamed in surprise. His hands immediately went to work exploring my body. Groping and squeezing my ass, tits and thighs. Fingers probing my pussy and rubbing my clit. Within minutes I felt his hard cock rubbing on my pussy.. he thrust it in me while holding my hips. He pounded me while he spanked me, pulled my hair, and held my arms back so I’d arch my back while he filled me. His cock felt great. Good size.. and he was fucking me hard making me moan for him, despite neither of us saying a word to the other. He roughly fucked me before pulling out.. he grabbed my left hand and pulled it back towards him.. he then came all over my
Wedding rings as I collapsed to the bed. He got back behind me and rubbed his cock on my
Pussy and ass before stepping away. He didn’t rush.. but he got dressed and went for the door. The only words we finally exchanged was him saying “fucking slut” as he left.

4
# 80273 - by SecretSlutWife / July 3, 2025
- My Cheating Heart -
Bi-Sexual Female / 44

I Don't Want To Stop

my husband and i have always shared fantasies with each other. it started when we were dating and continues even today after 20 years of marriage.

i am bi, so when my husband told me of his fantasy of having a 3some, that was easily arranged. it's one i could easily get into and it's not like he's cheating on me, we both enjoy inviting one of my friends to join us. she's bi and enjoys an occasional fling too. this has gone on for about the past 3 years now.

my husband came up with a "new fantasy", about a year ago. he wanted me to be with another guy.

at first it was just some surprising pillow talk, then he started asking if i was interested in trying the "hot wife and cuckolding scene". i didn't.

i couldn't believe he started pushing that idea that it would be extremely exciting to have me with other men. he did though, and i finally agreed. i contacted an old BF that i always enjoyed before i was married. his wife had passed a few years earlier and was open to seeing me again. i told my husband that i had found someone interested and asked if i could meet him before hand. my husband agreed.

we agreed to meet at his apartment a couple days later. i no more than knocked on his door when all the memories of being with John raced back into my mind. i was well in to a wet panty situation before he made it to answer the door.

the door opened and there stood not the man of my memories, but a well chiseled, handsomely aged hunk. i leaned in to give him a hug and a kiss, but i was all over him, and he all over me. the sexy times we enjoyed from before, had smoldered and now ignited into a full on sexual craze. we had sex for the rest of the afternoon !!!

i arranged with my husband and John that we would do our first date a week and a half later. in the mean time, i saw John nearly every day.

the day came, we met. we went through the formality of drinks and idle chit-chat, the entire time my brain was screaming to feel John on me and in me. after what seemed like forever, we "adjourned", as my husband put it, to the bedroom where we had set a chair for my husband to watch John and i have sex.

my husband seemed to enjoy us stripping each other, we did it kind of sheepishly with him watching. we kissed and eased into the bed. it didn't take long at all, and we both forgot entirely about my husband watching.

i had his big cock, much bigger and thicker than my husband's, in my hand and stroking it, then i started kissing it, licking and sucking the head. John moaned and said he was about to cum. i let him slide into my mouth and down my throat. he instantly exploded and i eagerly gulped his cum. that was the start of the explosion of sexual frenzy that followed. it became painfully aware to my husband that i was enjoying John way too much for his liking. my husband tried to slow things down, but we couldn't be cooled off. at some point, he left me and John to "go for some air". we didn't stop until daylight was coming through the windows.

John left, and i found my husband passed out in a chair, obviously well intoxicated from the scotch he emptied from the bottle on the floor.

i was told, "we'll not do that again." that was the end of the discussion. the "hot wife and cuckold" fantasy was over and never mentioned again.

i love my husband, but i didn't stop seeing John. i have been with him every chance i get since. John and i don't make love, we have sex -- wild passionate sex. he bounces me from the bed with his thrusts, i stream in ecstasy when i feel him explode inside me. John is so much bigger than my husband, i barely feel my husband in me any more. i have never let my husband do anal with me. i tell him, "it's too uncomfortable." John takes me. whatever he wants, he just takes it from me--vigorous and carnal. we are animals mating.

yes, anal hurt with John the first several times. he enjoyed my screams. now, i still scream, but only for John because my back hole is stretched to fit him now. i still do not let my husband even think about anal.

i know i'm a cheating slut now, but it was my husband that got me hooked back on my ex, and i'm not giving him up a second time!

Liz

11
# 80276 - by Liz / July 3, 2025
- True Sex Confessions -
Bi-Sexual Female / 36

Car Wash

Often when I wash my car, I will get the automatic wash at the gas station and take the time for some solo fun in my car. Usually keep it pretty discreet, just leaning back a bit and fingering my pussy. There have been a few times that I’ve gotten my breasts out too. I’m sure there are cameras, and gas station customers not far away.. it’s a rush.

2
# 80280 - by SecretSlutWife / July 3, 2025
- True Sex Confessions -
Straight Female / 52

BBC Infatuation

I am 52 years married woman. My husband was my first and never been much sexually adventurous and never knew any black man. But around 10 years ago I saw bbc porn and I couldn't stop watching and fantasizing. And then around 6 years ago a black manager came in our office from USA and he seduced me. I am small petite woman with big breasts and he could easily pick me up and fuck me hard. I couldn't believe that I could take his 9 inch thick cock but I did and I orgasmed multiple times like I was being exorcised.

10
# 80284 - by BlackedWife / July 3, 2025
- True Sex Confessions -
Straight Male / 35

Neighbors Wife

Last week I fucked my neighbour. Ron and Eileen live next door. Eileen is chubby or more like fat and is 44 and Ron is 62. A big variation in age. Ron has ED and cannot perform adequately to satisfy Eileen's sexual needs.
The have two old sons in their early twenties
Ron was out of town on business. The sons are away for the summer working with their uncle on his dairy farm in Wyoming

On this particular evening Eileen was sitting outside on her deck enjoying a glass of wine
When she saw me get out of the car she said and wanted me to join her for a wine

We chatted all evening and I knew from her conversation and her flrtiness she like to get laid. We went inside and sat on couch
I took a big step and put my arms around her and kissed her. She never stopped me and soon I was feeling her big boobs, nibbling on her ear lobes, licking her neck and French kissing her.
We went to her bedroom. Like I said earlier. Eileen is a big woman.. 5 ft 1in and about 200 lb. Rolls of fat and a mommy pouch. I did not give a fuck about her size . She opened her fat thighs and I mounted her and inserted my hard cock. She moaned. I kissed and sucked her nipples inserted my tongue in he mouth and thrusted in and out like a piston on a motor. Only sounds were our moans, my balls slapping her c**t and the bed squeaking as I drove her ass into the bed with my thrusting..I pounded away for about 4 or 5 minutes and I felt my load churning in my balls.. We were sticking together with stick. My cock started to throb and I shot my load of baby batter in her wet c**t.
I rolled off her ..I was spent

3
# 80248 - by Tobias / July 2, 2025
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