Naughtiest thing you ever done?

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biggee
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Re: Naughtiest thing you ever done?

Post by biggee »

Fucked my at the time 28 year old step daughter
We never finished because she came over with guilt but every day i regret not even trying to talk her round
oliviaanne
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Re: Naughtiest thing you ever done?

Post by oliviaanne »

I'm not sure about naughty, but it's definitely the most voyeuristic thing I've ever done. About six months ago my boyfriend’s brother and sister in law invited us over for dinner. I'll call them Nick and Kristina. We had a lovely dinner with plenty of cocktails and a couple of bottles of wine. After Kristina and I finished cleaning up we joined the guys who were already in the hot tub.

Nick and Kristina were telling us about their honeymoon in Jamaica and how they had spent an afternoon on a nude beach. The guys started teasing and daring Kristina and I to take our tops off. Well, I guess I had just enough wine to make me say "fuck it, why not?" I untied my top and Kristina did the same. I was not at all expecting what happened next. Nick stood up and dropped his swimsuit exposing a raging hard on.

He stepped toward Kristina and she promptly took his cock in her mouth and started giving him head. Not to be out done my boyfriend did the same and the next thing I knew Kristina and I were side by side with the brothers cocks in our mouths. It all ended with Kristina and I bent over the edge of the hot tub getting fucked from behind. It was so hot looking at Kristina getting pounded. Her face was flushed from the heat of the hot tub and the hard pounding Nick was giving her.

It wasn't much longer until Nick pulled out and shot his load onto Kristina's lower back. Within just a few seconds of Nick cumming my boyfriend squeezed my hips and his cock pulsated inside me as he came. We ended up leaving the hot tub and all fucked again on their living room floor before going home. I'm sure the thought crossed everyone's mind to swap partners, but I'm glad we didn't.
dlihret
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Re: Naughtiest thing you ever done?

Post by dlihret »

Not sure if this is naughty or just daring.
In the mid-70’s, I was working in the Midwest as a traveling salesman. Without getting into all the details of how it started (maybe I’ll submit in stories), I was having an affair with my biggest client’s wife. If that wasn’t bad enough, one day I met with my client in the morning. After the meeting I met his wife at the home of his secretary. Yes, his secretary knew I was screwing her boss’ wife! There were other adventures with her that risky, but that was definitely the craziest.
jester73
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Re: Naughtiest thing you ever done?

Post by jester73 »

I recently had a night of fun with my son, his girlfriend, my girlfriend and myself of course. Started out drinking and playing cards against humanity. The more relaxed we got, the stronger the flirting. We took a break from the game and my GF came back first. She dropped to her knees with a grin and pulled my dick from my shorts and started sucking. When she heard the others coming back she tried to stop but I held her and said don't stop. When my son saw what we were doing he grabbed his girl and made her drop and start sucking him. After a couple of minutes I said "we need to move this party to the bedroom." Things started normally, the couple's staying together. But after fucking my GF a few minutes, I asked D if he wanted some of mine. He said yeah so he came over and I went to his girl. She was 15 when they started dating and I always thought she was cute with nice big tits. Now she was legal and I was going to fuck her like I always wanted. I got between her legs and licked her through a couple small orgasms, then climbed up and fed her my cock. She's good, but I wanted her pussy, so I pulled away, slid down and eased it in her. While all of that was going on, D had gotten down to business of eating my girl's pussy, making her moan and roll around. He stood up, pushed her knees back and pushed deeply in and started fucking her hard. After a couple minutes we both stopped for a moment, so I told the girls to play while we took a moment to catch our breath. They kissed and took turns licking each other's pussies. My son and I were ready again, so he grabbed my girl and she showed him how she was at sucking cock, do not to be out done, his gf started sucking mine, getting us both hard. An old fantasy of mine came to mind, and I asked her if she wanted to see me suck my son's cock. She said yes, so I told her go ask him if he wanted me to. He said yes and got comfortable and he fed me his hard dick. I had dreamed of doing it for years, since he was 14 or so. I tried to deep throat him, but I had drank to much and I couldn't handle it. We had all drank to much really, because none of us, with the exception of his gf, came that night, but we all had fun and some fantasies were lived out finally.
gavin1969
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Re: Naughtiest thing you ever done?

Post by gavin1969 »

My sister and mom introduced me to shaving cock/balls when I was 15! We were an open family and loved our bare bodies in front of each other! Mom shaved me first, and I returned the favor for her. There was no objection from dad, as he liked her smooth 2. I shaved my sister and vice versa...so hot! We all have weekly sessions 2gether...the best!
danman3625
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Re: Naughtiest thing you ever done?

Post by danman3625 »

naughtiest thing i have ever done is let my wife fuck a male coworker on the couch while i took video of them and jacked off all over both them as they were finishing up ... she ended up fucking him on a regular basis and i was ok with it because i ended up fucking her sister without her ever knowing
prowanker
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Re: Naughtiest thing you ever done?

Post by prowanker »

Well like many of us, one or two things come to mind but this stands out in my mind for sure. One of my best efforts I believe.

About 15 years ago my stepson was going out with his HS sweetheart and was very close with her family of single mom Sandy (mid 40s)and her two younger sisters. Ellen was 20 at this time, her next sister Haley was 17 and youngest Terry was 15. All cute kids and a sweet mom who adored Jim as the son and brother they didn't have. They did so much together and made Jim part of it all......Including family vacations.

At that time they were having a big family vacation in the Caribbean and were all going for a week. As we lived around the corner from them I volunteered to look after their pets and keep an eye on the house. I worked from home and could go over anytime I liked......I actually liked a lot.

In addition to being a dyed in the wool wanker, I am also a voyeur and nosy to boot. In addition, I enjoyed "borrowing" soiled panties for my stroking sessions. In this case I hit the motherload.

As I said, the girls were all cute and Ellen and Haley were really built. Both a little bit "solid" but not fat and both stacked. Little sis was a bit taller and skinnier but also developing a fine rack. Mom was the smallest of the lot, almost tiny at about 4.5 feet and light...maybe around 105 pounds, firm body , killer legs, arse and tits. They were definitely all easy on the eyes.

Since our boy was close to them we also became close and were invited to all their outings and parties...but we couldn't make this one. None the less we saw them alot. I could see why Jim was so close to them all......but I really didn't realise how close until this "project".

So as is my modus operendi , I started by checking on the animals, feeding and watering them before snooping the house. What a wanker's delight. Something in every bedroom and washroom, nickers, toys and diaries everywhere. I was in heaven with 7 days ahead of me. I couldn't decide where to start. Go youngest to oldest or the other way???? I finally decided on mom first.

I had always fancied Sandy, she was tiny but a ball of fire and hilarious. A brunette, she always looked stunning from a tee shirt and jeans to a cocktail dress, a knockout. One outfit she once wore almost caused me to cream my jeans right on the spot and I actually had to go stroke myself as she visited with my other half. Black leather miniskirt, white see through blouse with dark bra, black nylons with the elastic tops and 4" black stilettos with gold heels. I had to find that outfit for closer inspection. Finding it, I smelled every inch of it and held the bra, blouse and nylons to my face as I beat off. I came in seconds and shot a hell of a load.

A bit later I snooped around and found her toys and a diary, In the diary I found some snapshots of her in a black corset and the nylons and shoes............with no panties. Her lovely brunette bush on display. I just had to yank it again. This time I came in one of the shoes ( I might have a shoe fetish?) Unfortunately we did not have cellphones with cameras so I couldn't copy the pics for later. Bummer. I did clean my spunk mostly out of the shoe.

The writing in the diary were interesting but not boner inducing but I did come to a small notation that read that while she loves Jim like a son and would welcome him marrying Ellen..............sometimes he makes hers feel so horny and she would die to fuck his brains out. Good for you son.

I think the first day I spent about 2 almost 3 hours there so I didn't do much more other than pinch a pair of Sandy's dirty nickers for a later rub and tug.

The next days it was the other girls rooms and their treasures and I really hit paydirt with Ellen's room. Several pairs of nice dirty knickers to choose from but it was her diary that pushed me over the edge so to speak. Lots of young girl's affirmations of love and some in depth recording of first hand job, first blow job and first time he ate her pussy. Amazing to read but the kicker were a series of 10 or 12 polaroid pics. What blew my mind were not just the 6 or so of Ellen and Jim at it.......but two each for Haley and Terry. Each of them blowing Jim and he eating them. I later found a diary in Terry's room recording the event and her feelings. She said she was scared and super excited and then out of her mind when he ate her. She said she really liked sucking his dick but was surprised when he shot his load in her mouth. She said it tasted good and she'd hope to do it again. I wonder if they did?

I was flabbergasted or gobsmacked as the Brits say. But not too gobsmacked to toss off a couple of loads to those pics. Man I was in heaven.

I spent the rest of the week re-reading the diaries and checking the photos, smelling panties and tossing off all over the house leaving little momentos here and there.

When they came back I couldn't help smile at them all and I was always laughing and grinning at them for years thereafter. Jim and Ellen did get engaged but something happened and they parted ways quite soon there after. They both married different people and each now have kids. I haven't seen them in probably 6 or 7 years other than the odd post on Facebook. I have never asked Jim about any of it and I doubt he would tell me anyway. He was a lucky guy for sure.

Does that qualify as naughty?

cheers,
Pro
skinnywank
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Re: Naughtiest thing you ever done?

Post by skinnywank »

Throughout high school and parts of college I worked at a Country Club in the restaurant part. The same members would constantly eat there so it wasn't rare to know customers better than a normal restaurant. There was this one older couple (early 60s) that would eat there about once a month and were usually at all the member parties. They usually brought their daughter and her family with them, but they did occasionally come by themselves. I started busing tables at 16 and they immediately took interest in me. They always told me how much I looked like their nephew. Over the next couple years it was a pretty normal where we would chat when they came in.

When I turned 18, I could finally serve the tables, not bus them. They came in one day by themselves and we were chatting. I explained to them now that I turned 18, I could finally make real money. That sparked them up big time. I always looked younger for my age so I don't think they thought I was 18. During that night the conversation kept becoming flirty. I didn't mind it so I just played right back. So they were done with dinner and ordered desert to go. I brought the check and the desert and wished them a good night. When I picked up the check there was a note in there with their phone number pretty much inviting me to their house for a good time. At first I was like that's gross (they were decent looking, nothing good or bad), but as the night went on, it got me hornier thinking about it. I said what the heck and texted them. They gave me their address and after work I went there.

As soon as I walked in, it was on. They were already naked and he already had an erection (think he took something to get it up). They thanked me for coming and said that they were both bisexual. I pretty much said I am open to anything. They told me to get comfortable (which meant get naked) and they both undressed me. At first I was soft, but with both playing with me, it didn't take long. We were fooling around in their living room (pretty much did everything mmf do) and it was like something I never experienced in my life. Everything was going as normal as possible until I heard someone come through the door. Like I said, we were in the living room and I thought they lived alone so I was shocked when someone walked in. I quickly pulled out of her and tried to cover up with a blanket that was on the couch. For as shocked I was, they were the exact opposite. They say hi to their niece (who I guess lived with them) and chatted like it was a normal day. This chick used to come into the club with them and always thought she was a little strange. Like a little bit too much of a band geek. They introduced me to her and all I could muster up was a hi. They told her what I was doing there and encouraged her to get changed and come up if she was interested (she had a in law set up in basement). They looked at me for assurance that it was ok. I just shook my head like I was good with it. As soon as she walked out of room I asked how old she was and they said 19. They explained that the college she goes to is closer to their house so she asked to move in last year. They explained to her that they weren't going to alter their lifestyle so this is something she would need to be ok with. I asked them if she normally played too, and they said it depended on the guy. They were never anything done physically with each other (niece and grandparents), so she would have to be ok with the guy.

So about a minute later this girl comes up naked (actually was a lot better looking naked than I expected) and said she was going to warm up a little. She had this huge bush which is honestly what I kind of expected with someone of her type, but it was a huge turn on. She starts rubbing herself on the recliner while the three of us get back to mmf play. We were going at it about five minutes when the lady says for me to go to her niece. I pull it out of the lady and head to her niece and stick it in. She was way tighter, but I was nicely greased up from the grandma. We start going at it and they both come over. The grandma is rubbing my balls as I am in the niece and I can feel the grandpa's erection on my butt (didn't put it in, but had the head rubbing all over). This was going on for about 10 mins and it was getting close to both the niece and I to climax. I orgasm, as well as she does, inside her and it was just spectacular. As I pull out of her, I can tell the grandpa came on my back at the same time we did and the grandma must have fingered herself with her other hand to orgasm because she had that spent look on her face.

The grandma was the first to get up and she brought back towels to clean up with. We all cleaned up and it was pretty quiet. I got changed and said my goodbyes.

The next day I did end up texting them to see if the niece was on birth control. They told me I have nothing to worry about, she had that thing inserted in her when she was 18. I said thank god and they invited back whenever I wanted. I would get random texts from them on weekends telling me they having some fun that night inviting me. I sometimes would show up for a repeat. It got more normal as time went on and it was cool how open things were in that household, but it definitely was the naughtiest thing I ever did.
legions9999
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Re: Naughtiest thing you ever done?

Post by legions9999 »

I thinks its time for me to come clean. I have several stories and am getting old so I need to clear my chest. When i was a kid living in california i had just reached that age where you start feeling yourself, exploring. Right off the bat i noticed something. When we would run lapse my thing would rub but it felt good. Guys in the locker room would always call me sausage due to my size. Then the fateful day happened i will forever regret. I was watching a movie on my tv and my dick got hard. Mom didnt get home till 5 and i was curious so while in the den i pulled it out and started rubbing it..like it felt while running rubbing on my skin. Mom and dad always said i was a miracle child because dads sperm count was low evidently. So with my dick which is 6 inches thick and 10 inches long ..even as a boy..i began stroking it faster. Pulling my pants snd underwear completely off It felt so good. Then i hear a voice "Wow babe thats huge" My mind went blank and I fumbled around trying to pull up my underwear! I was shaking almost crying and there stood mom. Mom was a secretary for a law firm and was prettier than any woman on tv! She sat down beside me and said its time to have a talk. She said what i was doing was normal and I shouldnt be ashamed of it. She then told me to pull back down my underwear. My dick was stilk semi hard. She then told me to stroke it like i was. So nervously I began again. She then told me i was doing it wrong and ask me if i have been having pains down there. I said kinda pointing to my balls. She then took her hand and put on my shaft. She told me she loved me and all mothers do this. She started slowly stroking me then spit on my dick. At this point i was fully erect and my legs started going and was getting a weird sensation from down there. Then she told me it wouldnt work unless she done some more stuff. As i started quivering orgasming i know now, she pinched the end of my dick hard and base. I felt a pulse and my body started shaking but stopped as she pinched harder. She then told me to breath and she would do something special. She reached back and unzipped her skirt and it fell to the ground. Standing there in front of me was my naked mom. She then took off her blouse and bra. Young and first sight of a naked body i was curious. She then leaned forward and kissed me on my forhead. See josh i kiss you and i am your mom right? I replied yes as my dick was hard and lower balls hurt bad. She then told me to kiss and suck on her breast. She sat on my knees as i sucked her soft breasts. To this day i still remember the taste. She then pulled my head back and told me to relax. She sat facing me and i remember feeling something warm on my tip of my penis. She reassured me its natural and it might feel weird but she loves me. Then i felt a weird warm stretching thing start going down my shaft. She started breathing real hard saying "God your stretching me out son" Then she leaned forward and gasp as i felt the warm feeling engulf my dick fully but it would only go so far. As she went to stand up then sit down i felt friction and it felt good! I looked down and my dick was somehow inside her? She started really sitting on me and told me to suck her tits. Then she started yelling Oh god josh im coming then something tight like her hand pulsed on my dick and my legs shook!! My dick felt like i was peeing in spurts warm spurts. Everything started fading out as she moving on me. I felt the best feeling in the world!!!! as she grabbed me tight and started shaking. The hot kept pumping out and i could feel it running down my thighs. She made 1 last grunt and collapsed. My thighs were soaked with hot liquid. She then stood up and I felt her slide off. She told me she loved me and go take a shower before dad gets home. As she stood up i noticed a bunch of clear liquid running down her leg. She told me she needed to lay down before dad got home. I wish this day never would have happened. I went to the bathroom and wiped all the sticky off and the stuff coming out of my dick. We had dinner when dad got home and mom was walking like she hurt herself somehow. I dont know of the timeline but i am sure 2 months later mom and dad told me i was having a brother
goodniteswearer89
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Re: Naughtiest thing you ever done?

Post by goodniteswearer89 »

Naughtiest thing I have done is I have done a few I have jerked off my younger brother when we were younger and he was asleep. I have also used some of sisters underwear and swimsuits to jerk off with and also took some training pants from my aunt and wore them I also tried to get my younger brother to wear training pants and got him to.
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jonni650
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Re: Naughtiest thing you ever done?

Post by jonni650 »

Around 15, I snuck out of the house into the woods behind our house (and the neighborhood), stripped naked, and frotted with the trees and the dirt, fearful yet exhilarated that I might be seen.
Years later, in the Black Hills of South Dakota, I climbed to the top of a tree covered hill, got naked, and spent the afternoon jacking off and hoping a hiker would pass by and see me.
In the middle of the night, at a waterside parking lot, I let a guy facefuck me through my open car window.
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latinababii
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Re: Naughtiest thing you ever done?

Post by latinababii »

Once I let my little brothers friend watch me masturbate. Long story short he’s a little perve and was peaking through my door one night when he supposed be hanging out with my little brother. Anyway I was into myself pretty good laying on top of the bed legs spread furiously rubbing my clit when I saw the door crack open. There he was just staring at me pants down jerking off his little dick.. it kinda turned me on so I called him in told him to sit at the end of the bed. He rushed in shut the door and sat down. Then told him he can watch as long as he’s quiet. I continued to play with myself as he stared at my fucking myself but didn’t move. I stopped and said to him this is what you wanted right? So then jerk off while you watch I wanna see. He started to jerk his little dick as I played and after maybe 60 sec he’s started cumming and squired on my legs.. I was still goin but seeing him cum just about set me over the edge when he blurted out you saw my I wanna see you! So I closed my eyes though about him cumming on me and came so hard my body shook.. his jaw was wide open.. to be continued
wankel
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Re: Naughtiest thing you ever done?

Post by wankel »

Masturbate to parents having sex in the other room
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gerben80
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Re: Naughtiest thing you ever done?

Post by gerben80 »

Last year I was in a showerroom on a Campside.
I was very horny, so i got naked and startet to rub my hard cock.
I didn’t notised, there was a door to a sauna with a window in it.
In there were a couple of men.
When i discovered this, I started wanking in front of the window, it was so hot, because they had already seen me.
Next morning, some men were looking a bit weird at me....
nikkixsmooth
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Re: Naughtiest thing you ever done?

Post by nikkixsmooth »

Might be a tie.

1 - Worked at and got repeatedly fucked in a European brothel while backpacking across Europe.

2 - Several sexual favors for my then-boyfriend who was a dealer. Obviously a shitty one.
marcosb
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Re: Naughtiest thing you ever done?

Post by marcosb »

When I was 10 my 13 and 15 year old brothers and 3 of my guy cousins aged from 14 to 20 something decided that it was time I learned about sex. I was their shared bottom bitch from that point on. They werent mean about it, they were gentle and made sure I enjoyed myself. But apparently its a thing among all the unmarried guys in my moms family. We still have some wild nights of ass play and sometimes we bring a youngen in to the fold to enjoy themselves like we do. Crazy huh ;)
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txspeedfreak
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Re: Naughtiest thing you ever done?

Post by txspeedfreak »

I like to get naked when I'm at home and watch porn and stroke my cock. Well I like doing this when my daughter is here. Shes caught me several times. Always turns me on to see the look on her face when she catches me.
wachtruppe
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Re: Naughtiest thing you ever done?

Post by wachtruppe »

When I was 11 and my brother was 15 he would have me strip naked with him and have me wear a pair of moms worn panties and bra. I would jump up and down on the bed for him while he watched. My cock would rub against her lace panties and get hard. He would get really hard and rub his cock watching me. When he was close he would have me get on my hands and knees on the edge of the bed. He would slip his cock into the panties humping against my erection and humping my butt crack. When he was ready to cum he would cum all over my ass and let it run down my crack onto my balls. He would rub the cum soaked panties on my cock, balls, and ass.
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wonderdick
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Re: Naughtiest thing you ever done?

Post by wonderdick »

Wow that's amazing. Wish I had a brother like that!ci wonder how I would have felt. Did you like it?
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