Naughtiest thing you ever done?

[marston]

Lost my virginity to my older cousin.
I'll probably post the full story at some later date.
Basically her and my aunt were staying with us for a few months and the short version is she climbed on top of me and rode me until I shot my load inside of her.

[chris91]

House sitting for a friend and I decided to snoop, found her dildos and went through her panty drawer, went back again the next day and took them out and wanked to them but didn't cum in them, was going to steal a pair but they were all clean and was worried she'd find out

[remember94]

I masturbated to orgasm one bed away from my dad in a hotel room when I was 16. The lights were out and he might have been asleep…might. I was soothing myself to sleep by slowly masturbating my mostly soft little penis through the fly of my boxers…and then I was hard…and then I was stroking my thin teenage erection as urgently as I could without moving the covers too much.

My penis was already its full adult length (a scant 5 inches) when erect, but my 16-year-old hardons were still much thinner than they are now. All these years later, it still really turns me on to remember that I still just barely had a boy's penis the one time I kind of got to masturbate with my dad.

The easiest way to not move the covers too much was to lie on my side. By luck of the draw, being right handed meant turning towards my father, maybe 6 feet away, as my orgasm approached. I got close, got cold feet as he turned toward me (I think) in his sleep and made an anguished decision to just edge a while and go to sleep. The edge and the excitement of finally getting to rub my penis this close to my dad just felt better and better, though, and as 16-year-old boys are wont to do, I went over. It was one of those orgasms you try to hold off, but then just through caution to the wind and stroke for all you're worth once you realize it's happening. Ejaculating right onto the bed, my little penis squirting right towards my dad, near enough his own son's cum might have hit him if not for the covers, was one of the most intense, most wonderful experiences of my young life. Even for 16, I ejaculated sooo much too. I honestly wonder just how much young cum I might have been able to squirt through my slender penis with lights on, covers off and my dad awake and openly watching me masturbate like I'd secretly wanted for 6 years by that point.

He never clearly reacted or said anything, and I assumed at the time he was asleep, but after reading a number of stories here about parents discretely watching their teens masturbate, I'd like to think my dad secretly watched me. It's fun to imagine him hardening with pride at hearing the 5 or 6 quiet spurts of his son's ejaculation hiting the sheets, waiting til I was asleep and stroking his bigger, thicker cock to its own orgasm. So yes, I love to imagine my father ejaculating while thinking about my small, young penis.

Hmm. I wonder if maybe he did know? Now that I think of it, my dad must have smelled my cum when I kicked the covers off and walked barefoot to the bathroom (trying to hide my skinny, urgent morning wood) the next morning. I think there was even still a damp spot on my bed. As innocent as I managed to be then for a boy who was about to be sitting on the toilet, relishing the brazenness of letting his semen fall where it would on the floor and in warm drops on his feet, I doubt I would have noticed the scent of a man's cum mixing with the scent of a boy's…

[seemslikeaniceplace]

Playing dare with my sister and her friend. Her friend jerked me as my sister watched. Both had taken off underwear which helped:) Sister wouldn't copy her friend. Not that time anyway...

[ruthborn]

Ah, geez. I've done so many naughty things as a kid but I think the top two have got to be....

When I was 13-14 and I nearly drowned myself masturbating underwater in the ocean. Long story short I was feeding the fish my newly produced cum and was receiving the biggest orgasms I had ever experienced in the process as I was running out of air. Nearly died but it felt incredible. Definitely the most stupidest thing I've done.

My other most naughtiest thing I've done is willingly letting a guy take me into the public park toilets when I was 14-15 and letting him suck me until I gave him my cum twice.

Of course I've done other naughty stuff as well but I think these two are my most naughtiest.

[phileld]

Huh. Covers a lot of ground.

Most recent that comes to mind: both in our 30’s, my sister who lives out of state came to visit my parents and stayed at my house. I purposely tried to get caught jerking off with her panties. Mission successful. After getting caught she just smiled and said “just put them back in my suitcase when you’ve had your fun.” Then with a grin she added “don’t wash them”

[donexposed]

I always enjoyed masturbating in my kids' beds as they were growing up. I loved getting the house to myself so I could take off all my clothes and go into their bedrooms and masturbate, usually while lying on their beds. To this day when I think about it I need to masturbate!

[bjob13]

I always enjoyed masturbating in my kids' beds as they were growing up. I loved getting the house to myself so I could take off all my clothes and go into their bedrooms and masturbate, usually while lying on their beds. To this day when I think about it I need to masturbate!

i have jerked in all the rooms of my house, kids rooms also. Love to get naked and stroke around the house.

[ross1957]

At 15, one of the naughtiest things I have done was masturbate for my friend and his sister, who was in the year bellow us at school. We were playing a game of true, dare, kiss. We had got to the part where we take our pants off. She had gone first and was now sat cross legged opposite me. I was dare to remove my pants and I’m sat there with an erect penis, my friend is the same. He dares me to masturbate, which I did, looking at his sisters open legs.

[justpeekin]

I guess the naughtiest thing I ever did was to masturbate in class at school. I was bored and had one of those random adolescent erections, so as the boy I shared a desk with was away, I gave it a squeeze under the desk through my trousers. I had just discovered edging, although I didn't know what it was called, and basically started doing that. Felt good, and this went on for quite a while (double English!). Finally, at about the 10th edge, I went too far and came in my pants. Quite a mess!

[jennam]

Hmm, there are quite a few but one of things I have to say is at school once (must have been about 15ish), 3 other girls and me were talking about our pussies.

We were on a table just us 4 and all wearing our skirts and decided to all show each other ours. Mine was nicely shaved by this point but I remember of the girls had a full on bush. It turned me on so so much, I still remember pulling my pants to one side so the girls could see.

We then all decided to touch each other, we couldnt do this for that long cos the teacher would see but I still remember my fingers touching my friends pussy. I rememebr that day after school coming back and finger fucking the hell out of myself.

[tava19]

When I was in my teens I used to peek at my mom and sister.. would always go jerk off after. Felt guilty but also found it so erotic. On one hot summer night. When I was 17 and sister was 19 I went by her room she was in bed in a short nightgown and No panties. I couldn’t resist, I went in to get a better look but her musk drew me to her. I just started licking…. She woke up. In stead of being mad she told me to close her door. Let me eat her out… happened many times after

[firecrotch55]

Jerked off for and with my younger brother and sister in our post pubescent years. Also progressed to some touching and dry humping.

[lexington]

While edging I started taking pictures of myself and even videos. Moving outside it was the naughtiest feeling to set my camera up and check the results.

[wheelboy2]

I masturbated in front of a female co-worker at work on two occasions. I knew she was horny as we had fooled around in a woods months earlier and had done everything possible except fuck. She even had a finger up my bum and she sucked me off. Anyway, at work I dropped my pants, knelt down in front of her and masturbated. She was fully clothed.

[lexington]

I have never had such a relationship, maybe because I believed girls were all prim and proper. Huge mistake.

[grayuk58]

i`ve done a few dirty things in the past.

my oldest sister called around my flat just as i`d got out the bath. it was an unexpected visit from her. id been wanking in the bath a kind of a tease wank. i`d been feeling really horny all day. when my sister turned up i immediately thought about carrying on in my bedroom and hoping she`d voyeur on me or even better come in and join me. so i left my bedroom door open a good bit and took my towel off and got on my bed. if she watched me she`d have been able to see me from the chest down without me seeing her. i was naked, legs parted, leaking pre cum wanking myself off very slowly and sensually as well as gyrating my body, occasionally slowly thrusting my hips, low level groaning just enough for her to hear even if she was in the other room but not making it obvious. i`d occasionally stop rubbing and just hold the base of my erection so she could have a good look if she was watching. i was so turned on and excited i was pretty much edging it trying to make it last. i`d leaked a lot of pre cum too so my cock was extremely slippery and making those naughty wet sounds as i wanked it. occasionally i diverted my eyes to my bedroom door without turning my head and really dont know if she was there watching but knowing my sister i`d say she definately watched. i managed to last half hour! i had the most intense explosive orgasm ever and i was covered in spunk. seeing it squirting out like that was a huge turn on too. when i rejoined my sister in the next room she looked very flushed in the face and i could tell she`d watched but i acted as if i had no idea. i was 40 when that happened and my sister is almost 12 years older. that was actually pretty much the best wanking session i`ve ever had solo that is lol.

another really kinky thing happened to me too in 2012. i started chatting to a married woman online. we chatted a lot. the conversations with her got naughtier and naughtier as time went on and we started having wanking sessions together. my oldest brother was moving abroad with his wife and family and some stuff he had he gave away. he gave me a motorcycle jacket pretty much unused so i had idea`s to sell it. when i mentioned it on the chatroom i was in the married woman said her eldest son was after a motorcycle jack. i gave her my mobile number and she called me next day to make arrangements for her and her son to come around to try it on for size. even though that was the very first time id chatted to her on the phone, after talking about the jacket and arranging a visit, our conversation soon got around to sex and we both ended up getting really horny and both started wanking and we both orgasmed. i remember it being the early part of the week and she arranged to come around with her son on the saturday so i had 4 or 5 days to wait. she messaged me on the saturday to say they were on their way. it took them about an hour to travel to me. i actually felt really nervous as i was about to meet the woman id been having wanking sessions with online and on the phone for the last month or 2. when we met she smiled and gave me a knowing wink as we greeted. her son was right behind her and so was her hubby lol. i wasnt expecting to meet him! must admit i felt mortified lol. i offered them a tea or coffee and went to my kitchen to make it. her hubby came out and joined me! he whispered to me he knew what i was getting up to with her lol to say i was shocked was an understatement lol but then he just smiled and told me he didn`t mind! i was still lost for words though lol. anyway to cut the story down a bit they were happy with the jacket and bought it off me. i spoke to her a couple of days after meeting them and told her that her hubby knows about what we get up to and she said she knew and told me her hubby didnt mind lol. a couple of days after that she phoned me. we had a good wank on the phone and afterwards she asked if i fancied visiting her and staying the weekend. i really wasnt expecting that! after quite a conversation i accepted her offer. she told me to bring some porn as we could watch it together as her hubby was working from 8 in the morning till midday. so anyway i made my way over to their place on the friday evening and arranged to stay till sunday evening. soon as i got there we had dinner shortly after then sat drinking coffee. her hubby was a nice guy very mild mannered. after about half hour he asked me a bit of a random question i wasn`t expecting. he asked if i`d ever smoked a joint lol i told him yes many a time then he asked if i fancied one and of course i said yes. he told me we`d have to roll it and smoke it in their bedroom because of the smell lol. the 3 of us went into the bedroom and all 3 of us sat on the bed and he started rolling it. he actually rolled 2. he lit one up and the 3 of us sat there casually chatting and getting stoned then he lit the second one up. i gotta say it was good stuff lol. anyway half way through the second joint the subject got on to nudity somehow. he said he loves being naked when he`s stoned and she said she likes stripping off too. i kind of felt anxious and a little bit nervy i didnt really know where it was all heading although it was obvious. he asked if id mind if he took his clothes off so i just said to him go for it. she said she fancied stripping off too and they both said i was welcome to take my clothes off too so i did lol. it felt amazing the 3 of us nude. he was sat next to her and i couldnt see all of him and i had to lean right forward to pass him the joint and when i did i could see she was wanking his cock and a very nice cock he had too. all i said was naughty naughty with a smile. he seemed a little nervous too and his voice quivered a little as he said they didn`t mind if i had a wank watching them so i did. he looked really excited and so turned on looking at my cock and watching me rubbing it. all 3 of us were very excited! he then asked if i`d brought any porn along so we put a film on. it was a schoolgirl roleplay film mmm lots of upskirt knicker views and really horny fucking and had one mmf 3some scene in it which excited the 3 of us. it has to be said all 3 of us didn`t last that long and it was me that started cumming first which set her hubby off and then her and what a session that was and the start of a very special friendship that lasted about a year which leads me to my next really kinky experience!

i visited and stayed with them 3 weekends in that first month. very very naughty meets. there was a morning where her hubby was working the half day on the saturday again so when he was out i was chatting to his wife. she was a very kinky dirty and fairly forward kind of woman. our conversation was a pretty naughty one that turned very dirty! she asked me if i had any dirty secrets! well i do but i wasn`t sure if i was ready to tell her just yet. i told her i did have secrets . she could see i was a little backwards in coming forwards so she just said to me she had a few very dirty secrets that she said would probably shock me lol this sounded good!!! i asked her what they were so she smiled, cleared her throat with a little cough then told me she wanked one of her dads mates off while he was talking to her dad through a serving hatch in her house so her dad had no idea. then she told me she seduced her sons friend once while her son was out at football practice. she got him so worked up he fucked the arse off her twice!!! and then her next confession was the best of all!!! she told me she loves teasing her brother. god when she told me that i then confessed about my sister too to her. she told me she thinks about him a lot and i told her i think about my sister. so dirty sharing your dirtiest secrets. the sex we had was nothing short of incredible. she told me her hubby knows all about her secrets and doesnt mind but it`s not really his kind of thing which is fair enough but it did open up a new avenue for me and her to explore and all with his permission. amazing times with both of them. i also lost my anal virginty to him and he lost his to me. for that year i think it was the horniest of our lives

[lexington]

Wow. I had a boring life compared to that!

[jlamoe]

In my childhood, we use condom to play as a balloon. It seems to be so naughty!

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[strokerace42]

Me and my friend were fucking my slutty gf and we must of got caught up in the heat. Right after I came deep inside her he pulled his dick out of her mouth and start slurping up my cum that was leaking out of her pussy. After he had a cummy mess running down his chin he plunged his cock in her and started fucking her hard. She asked him to pull it out and put on a condom. I was spent so I grabbed a few condoms out of the drawer and started to hand him one but he didn't stop. He gave her a few more hard pumps which quickly made her forget about the unprotected sex and within a few minutes he pulled his big cock out and I watched him shoot ropes of cum on her tits and stomach.

I was in awe, blood rushed to my cock and I was at full attention. My gf was laying there exhausted, covered in his jizz. I got between her legs while I was on my knees and easily slid into her wet pussy. We started fucking again and she sat up, wrapped her arms around me and pulled me on top of her. Our bodies were greased by my friends cum as I had another orgasam and filled her up again.