What is your dirtiest experience as a teenager which you want to share with everyone anonymously?

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Mudassir Ali 8 months 2 Answers 173 views

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  1. I used to have a Wattpad account for online roleplay. Usually I roleplayed as video game characters with others, in private chats incase it would get sexual. That’s what happened one day, someone PMed me and asked if I did DRP (dirty role play) and once I said yes we immediately started. This was pretty anonymous, with us both being female characters in roleplay (and our accounts), but a man and girl behind the accounts. I’m bisexual so either way gender wouldn’t have mattered, but I think it makes a bit of a difference in his situation.

    As well as age, I was 14 at the time and he had just turned 20 before he PMed me. Apparently he really liked my roleplay, and we continued this for about a month. We got pretty close and only had learned each others names and genders, we even decided to put each other in our descriptions as “RP friends”.

    It was really nice, I really liked him, maybe a bit too much. Regardless of our age, we’d both agreed we’d try roleplaying as each other together. We did and it was slightly awkward, but he said he liked it and would love if it could actually happen. I admit I did too, so I sent him a picture of my face. (Through another app because Wattpad sadly doesn’t support that.) He sent one back and we complimented each other a bunch, even being really insecure we kept sending them.

    Before meeting him, I’d gotten out of a hectic relationship with two girls and the reason I’d made the account was to find new friends, kind of just restarting a previous life. I was a little desperate to date a guy because I thought girls were too much drama. And I think he was desperate to date a girl since he was exploring his sexuality (through DRP mainly) and didn’t want to call himself gay.

    A little bit later he asked to call, so through the next app we were using for sending pictures, I nervously called him. He had his camera on and I saw him without a shirt, making me even more nervous. I kept my camera off and he kept asking “Turn it on, I want to see your pretty face, please?” He was very sweet about it but I was and still am too insecure and nervous, so I kept it off. As well as I was nervous about my nosy mother coming home and seeing me talk to someone online, someone who looked like an adult.

    At this point I was kind of realising he was older, so I asked his age and when he said 20, I froze. I muted myself and threw my phone as he had turned his camera off. For some reason I hadn’t expected this, he just seemed young the whole time we were talking!

    I vaguely remember what happened. “Why are you quiet? Did we lose connection?” When he said that, it gave me an opportunity to hang up and I did. As I did, I realised my mother had walked into the house too, so everything around me just left me paranoid.

    We’re getting closer to the naughty thing, I promise.

    I ignored my phone for a bit, trying to figure out what to do. I couldn’t fathom liking an older guy to be normal. I was this insecure 14 year old, who didn’t even like going outside and being with friends most of the time because I felt like I was too weird for anyone, but I liked this guy and he seemed to like me, and he’s 20!

    “I guess you don’t want to talk?” and, “Did you not want to do that?” He’s insecure too and thought I hung up and ignored him because he was ugly, which totally wasn’t it. He’s an insecure geeky guy, really adorable and attractive, I just wished he was my age.

    I quickly proved those questions wrong and told him my mom had come back. “You live with your mom? How old are you?”

    I was staring at this text for so long, wondering if I should lie or be honest and have him leave me forever.

    “I do. I’m 15.” It was only one number up, it wouldn’t have made a difference if I’d said 14.

    “Oh. And you like me? But I’m an old dude?” I rolled my eyes at those questions too, yes I liked him! I thought it was weird for me to like an adult too!

    “Yeah I really like you, I know it’s gross andweirdandIshouldjustgodiebecauseyouprobablyhatemenowbecauseInevertoldyoumyage!!!” and, “You’re not old tho! It’s just 20…” I was panicking and probably did write exactly like that at the time.

    “Well, I like you too. A lot. But IDK if we can do anything or be together…”

    “I know… I’m sorry.” We continued to comfort each other and try to figure what we were doing. Even after talking about laws (which I knew more about. Proves most millennials are ignorant, sorry not sorry…) and our age and distance, we decided to be in a relationship. I told him I didn’t want to send any pictures or do much, keep it strictly nothing sexual, and he respected it! He never asked for pictures or even drp, so I promise he’s not a creep.

    But… a few times he’d say he had to “brb” because he was horny, and the thought of him masturbating immediately went to my mind. It was almost a month later when I started masturbating to that thought too, and when I told him that, he brought up sexting again. My horny head gave in and we’d trade a couple pictures, I usually just showed my breasts while he showed his penis. (Yes. I know this is illegal, I knew it at the time too. As said, I knew more about laws than him.)

    He started sending videos of him jerking off and I would try being sexy in my videos, groping my breasts and rubbing my nipples. I actually like my breasts so that’s why I mainly sent them and didn’t feel terribly insecure. I’m a bit overweight too, and since he was overly excited to see me, it boosted my self esteem. That might be the one reason we really liked each other, was that we were super affectionate and loved each others appearance a lot, so our small egos grew and grew each day.

    It did get to full body videos, showing parts that no one else had seen. But it stopped for a bit because I was a teenager and started feeling heavily dysphoric at some point. I denied that I was insecure to him and said we were breaking rules and such, but he still doesn’t believe me.

    It’d been about four months later. a few weeks without each other’s bodies. For some reason this time gave us a lot of thinking, and a bit of drama. (I accidentally sent a nude to my guy friend at the same time I was sexting him and the guy friend and I started getting too sexual. It could talk more here but that’s for another time.)

    During an argument, he called me. I accepted it and tried being quiet since my mom was in the room right beside me, but he was really upset with me and was a bit loud, I couldn’t blame him though.

    I apologized and explained it was an accident quickly (It was an accident, but everything after wasn’t…im a terrible person.)… He forgave me and we somehow started talking about kinks and fetishes over the phone. I started talking about fantasies and wet dreams I had, and so did he. This got us both really turned on, so he again turned his camera on. I saw him naked and touching his hard on and that made me more willing. I turned on my camera and started undressing, and that led to us watching each other as we got off. I’m still surprised my mom never heard anything, even though I thought I was loud. It was great, even for being extremely risky, and our orgasms were extreme. I usually get tired after that though, so I fell asleep on the call and woke up to him looking at me with a big smile.

    That’s it, not the naughtiest thing on this page, but for me it is. It’s been a few years and now I’d be legal to be with him, but we decided we weren’t good for each other 10 months after that video call, the only video call we’d ever done, actually. I still talk with him some times because of the video game we still play, and the roleplay accounts we now share, and he plans on coming to my state some day. Maybe we’ll pick up that relationship again, when were both better mentally and can trust each other more. I’ll just have to stop dating so many people behind his back… (again, I know I’m a terrible person. I have commitment issues.)

    Sorry that was long! I’ve just always loved this man, wether sexual or romantic and friends, and I love talking about our relationship. It’s rocky but he’s my most favourite person ever, I love you, J!

  2. When I was sixteen, I injured myself in a high school sports practice and had to bow-out of the game. So every day after that I came home from school early. As a guy, this was a serious blow to my ego so I was a depressed a lot – I loved sports and while I could probably continue to play once I healed, I would not heal before I graduated. That really sucked.

    My next door neighbors were getting a divorce during those months. The shouts and screams, cops showing up several times a week. My parents told me the wife (Sarah) won the house and kids because the husband had cheated. Sarah was nice-looking but overweight from childbirths.

    Anyhow, one day this woman parks her car at Sarah’s house and steps out – and I thought she was an angel – i mean, perfect platinum hair, slender, tanned body, a nice rack, and legs that kept going. She wore a short dress and her legs were just outstanding. The muscle lines on her shoulders, thighs and calves, plus the veins around her calves, said she was a serious athlete in one way or another.

    It didn’t take long for me to realize this wasn’t any friend of Sarah’s – it was Sarah! She’d gone in for a makeover, had her extra fat stripped-off with lipo, and went into hard-core training to bring her body up to speed. And it was working for her!

    Every day she would arrive home from work and I would watch her walk the sidewalk, like a catwalk. Some days I filmed her and replayed them on my phone.

    One day she came to the house looking for my mom. She needed a babysitter for a couple of hours and wondered if my mom could help.

    “What’s it pay?” I said.

    She raised an eyebrow. “You’re not a pervert or anything, right?”

    “Not any more than the next guy.”

    She laughed. “You’re perfect. I’ll give you thirty bucks. The kids are asleep so you won’t have much to do. Come with me.”

    So I followed this goddess into her home and she showed me where everything was. Two hours passed quickly and she returned on time and gave me a pair of twenties.

    Every Tuesday and Thursday for several weeks, I watched the kids. They were very sweet and gave me no trouble. One day after she arrived home, a sedan showed up and it was her ex. It was his turn to take the kids for the weekend. She scooted the kids out the door and watched through the window, clearly holding back tears.

    I asked if there was anything I could do to help, and she said no. Then she changed her mind and said “Come here”. So I did, and she wrapped her arms around me. “Hold me” So I did.

    My cock came to attention in an instant. It’s big enough to notice, and she did.

    “Oh, goodness,did I do that? Come over here.”

    So she led me to the sofa and sat me down, and knelt between my legs. What happened next was mind-blowing. She pulled my member out of my pants and proceeded with the most fantastic blow-job I’ve received – ever. She knew exactly what she was doing. When I climaxed, she took care of all the mess. Spectacular.

    I went back home after this, walking on cloud nine. She came over when my parents were home and asked them if I could help her with some small projects in the house, since her kids were out. I rolled my eyes at her and feigned disinterest. I complained about having to go and then went anyway.

    “What was that all about?” she said. “Didn’t you have fun? Do I scare you?”

    “Not that – it was all a show. If I ran out the door she’d suspect something.”

    “Ohh, okay. I have to think in those terms. Got it.”

    We got inside and there was a plastic sheet on the carpet and two paint buckets with brushes. I wondered what she was up to.

    She stood me on the sheet and said the paint would ruin my clothes, so she helped me disrobe- everything. She took off all her clothes also, and my eyes popped. Her body was so rockin’ hot I couldn’t imagine her husband cheating on her- then I recalled how overweight she’d been. Oh well – none of that was here now

    She picked up a spray bottle and hit me with a burst. It was baby oil. She hosed me down and herself besides. We spent an hour slipping and sliding on the sheet, in and out of her, and all over her. She made it quite memorable. When we were done, I showered and used her soap that would scrub-out the oil.

    I went back every day to help her with “housework”, in the evenings when the kids had gone to bed. She was very creative in the “projects” she had for me, and we did it all over the house, in the wildest ways.

    One weekend when the kids were with dad, she took me on a shopping trip, she said – to a hardware store. We went instead to this really posh hotel on the other side of town. We spent all evening in sex, slept a while, had more sex, slept a while, and repeated this until check-out at noon the next day. We repeated this ritual at least once a month. Every so often, she took me to her fitness club and paid for my guest fee. This was late in the evening when nobody was around. She took me back to the sauna area and we did it in the sauna. The body oils, the salty sweat.

    She taught me a lot about sex, but also how to make a woman happy while having sex. I was a quick learner, and wanted to please her.

    This went on through my junior and senior years. It all ended when I went off to college. I kept trying to get back, like my whole body missed being with her.

    When I came back at the end of the semester, her house was for sale and was completely empty. Mom said she took a job in another state, but had left an envelope for me. It had a short note in it, thanking me for all my help around the house with her many projects, and a check for $10k.

    “She must have really liked your work,” Mom said.

    It never once occurred to me that what she was doing was against the law (I was a minor) or whether my parents would ultimately approve. They kept after me to get a girlfriend, but as I approached senior year, I could finally say I was going off to college and didn’t need to start a new relationship. Sarah gave me more than anything my friends were getting with their girlfriends. Who could ask for anything more?

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