Becoming TheDildoGuy

I wrote this as a way to process my sexual development, as well at to share my dirty secrets with like-minded people.

This will be deemed sexually devious, inappropriate and offensive to some people.


I’m a 33 year old guy, I’m in a hetro relationship and I’m straight.

I love sharing my sexual experiences on-line, particularly those from my teenage years. Sharing stories from my youth, and photos and videos of my more recent sexual pastimes is a very satisfying experience, and I love to see what others have to share as well.

Unlike my adult life, where I’ve had boring, regular sex with various woman, my youth was a ‘tour de f***e’ of sexual curiosity und unforeseen opportunities. My sexual development began at an early age. When I was about six some k**s at school found out what sex was and soon we all heard about it. I didn’t understand it of course, but I was very interested in it.

When I was 10 an innocent game of ‘Truth or Dare’ with a school friend and his s****r set me off on my bizarre exploration of sex. We were camping in their back yard and we’d moved in to the tent to play a game. In time the dares turned in to showing each other our genitals, until his s****r dared us to suck each other’s dicks. Fuck knows how she or either of us knew that that was a thing you could do, but we both had erections and sucked each other off without hesitation. Then we ‘dared’ her to suck us off and we got her to get naked so we could lick her vagina. It was a crazy introduction to the world of sex. I had many sexual experiences with my mate and his younger s****r from then until I was about 16. Within a year or so, we started spending less time as a ‘three-way’ and more time as a ‘cock-sucking duo’.

It’s dangerous having so much sexual power when you’re a 12 year old k**, and we became completely comfortable and open to lots of other dirty sex stuff. We found my parents porno collection at one point, which provided us with lots of ideas and further warped our fragile little minds! As well as sucking each other off and talking dirty, we also started to give each other rim-jobs, we tried lots of ‘simulated sex’, jerked-off on each other and in each other’s mouths and occasionally threw in some full-on kissing, which was really hot but always made us feel weird afterwards (licking each other’s assholes and cuming in each other’s mouth was perfectly fine though!). We also started doing it in our s****r’s and mother’s bedrooms when we were home alone.

His older s****r was hot and I wanted to fuck her badly. I had also developed lustrous feelings towards his mother, which I openly confessed to him. He was always happy to get naked with me in either of their beds. He soon confessed that he had similar feeling towards my s****r and my mother too, and somehow over time we admitted that in fact we were both inclined to want to fuck our own mother’s and s****r’s too. Once we had established that we both wanted to have sex with every female in our combined families, things got even hotter between us. From then on we always tried to use our mother’s or s****r’s bedrooms for our gay play sessions. Being naked and pleasuring each other in their beds made things even hornier.

It was at that point that we discovered the joys of dirty knickers, and the fact that they smelt like the vaginas of the girl who’d been wearing them. This meant that we could experience the smell and taste of the very pussies that we both were desperate to fuck. It became a great way to climax too, with either of our mum’s or s****r’s pussies effectively right on our faces as we sucked each other off.

It wasn’t just our mother’s or our s****r’s underwear that we used. Occasionally we’d get to use/borrow panties from the mothers and s****rs of our other friends from school, although in those circumstances we had to do it secretly and very carefully. But it was the knickers in my own home that appealed to me the most. It became a very fun and satisfying addiction to me. Almost every day after school, if my mate and I hadn’t arranged to ‘play’ together I found sexual gratification in the bedrooms of my mother and s****r. Often my s****r would be home at the same time, so I’d have to sneak in to our mum’s bedroom and take her knickers’ back to my room. My s****r’s bedroom was more easily accessible and her freshly undressed school uniform provided me with a reliable supply of the most freshly worn knickers I could get. Her scent was amazing, and the rush of being completely naked in her room, rummaging through her dirty underwear with a big stiffy between my legs, and knowing that she could have walked in and caught me was almost as thrilling as the wank session I’d have afterwards.

Jerking off with a pair of my s****r’s knickers wrapped around my face, and a pair of my mum’s panties wrapped around my cock, blowing my load in the pussy-stained crotch was purely awesome. Of course it was always more fun to get naked with my mate and have some real action, and we made each other cum hard almost every time, but using my mum’s and my s****r’s knickers became a very hot and very erotic ritual to me. The fantasy of fucking my little s****r of course made me hard, but masturbating over my mother made me cum harder than anything!

But it didn’t end there!

When I was home alone once at about 13 I found myself naked in my parent’s bedroom, as I’d done many times by then. Their ensuite bathroom was one of my favourite places to hang out. Mum always left her dirty clothes in there, so I had access to more than enough of her dirty underwear. I also enjoyed using their toilet for some reason, probably because I wasn’t even supposed to be in there, let alone being naked in there, sniffing and wanking in my mum’s underwear and pissing in their toilet!

My dad’s bottom draw was another hot spot for me. He had a nice collection of porno mags hidden in there, and in the space underneath the drawer he had a stash of porn movies. I don’t know what made me look there the first time, but he kept one ‘softcore’ porno, and about six ‘hardcore’ movies with anal sex, role-play i****t, peeing, group sex and transsexuals. That last one was the most shocking to see, and by far the most surprising one to find. My mate and I had watched them all many times by this point though, and had grown accustomed to the more ‘extreme themes’. His porn collection became a valuable part of my sex life.

As for my mother, who had slowly become an object of my desire, her unwashed knickers were like an amazing gift to me. I enjoyed taking my time gathering them up, smelling every pair as I played with my cock and walked around her bedroom. Mum also had a big underwear drawer and I liked looking at all of her knickers and bras. At the back was some sexy lingerie, like stockings, garter belts, lacy crotchless panties and matching bras.

My discoveries gave me a glimpse into the sex lives of my parents. I could see that they both had a sexual side and I was aroused to feel a common connection to them. Dad’s porn collection made me see him as someone with a very dirty mind, and perhaps some dirty secrets of his own. Mum’s sexy lingerie made me see her as a vary sexual woman who enjoyed fucking and liked to dress up.

This one day, I started looking through my mum’s bedside table. I’d looked in all three drawers many times before but they never held anything of interest to a horny 13 year old. I was incredibly aroused and felt a thrill as I rummaged through my mum’s private things. Without really thinking about it, I pulled the bottom drawer all the way out, and realised that if dad had hardcore porn hidden under his, then mum might have something hidden under hers.

And man, she did indeed. I have no idea why it took me so long to look there. Regular privacy breaches were my thing, but this one was massive!

I crouched down to look in the hole where the drawer was, and I see my mother’s glorious collection of vibrators and dildos. I recognised them straight away from my some of my dad’s porn. I knew what they were and I knew exactly where they’d been. It was a thrilling discovery and I didn’t hesitate to pick one up, give it a lick then take it in my mouth like a big dick, but a dick that I knew for sure had been shoved up the most ‘forbidden fruit’ I could imagine.

This was like the final straw for me. The reasonably modest view I had of my mum was shattered! I now saw her as a bit of a dirty whore who couldn’t get enough cock, and I liked it. She had like six 4” to 8” vibrators, from basic to advanced (she loved those rabbit vibrators) plus a couple of realistic cock dildos, vibrating eggs and what I think was an anal vibrator. One had lots of different attachments for it, and she had lube and condoms.

I hurried through the entire collection, licking and sucking everything I could find. The magnitude of how perverted and devious I had become hit me. Knowing that my parents were very sexual and shared a love of dirty sex helped me embrace my sexuality, for better or worse!

So at 13 years of age, before I’d even finished puberty I had about 6 people around me that I could rely on for some sort of sexual gratification, either directly or indirectly. My mate and I continued our always maturing boy-on-boy relationship, and his s****r would occasionally find herself naked with us, letting us eat her pussy and sucking our dicks (quite poorly mind you). We had no problem with her watching us pleasure each other either, and it felt even hotter having her there, looking me right in the eye as her b*****r sucked me off, or as I licked his asshole and jerked him off.

Aside from those two, I also had their mother’s and older s****r’s bedrooms to use, wanking in their beds, cuming in their panties (usually while sucking off or ass-licking their son/b*****r). And of course my mum’s and s****r’s bedrooms were always fun places to get naked. My s****r’s knickers smelt better than ever and my perverted plan to start secretly sharing my mum’s sex toys with her (properly) was underway. It didn’t take long before I was able to get her smaller vibrators up my ass, and of course it felt great to fuck the same toys that my mum fucked. The thrill of using them made me determine to get the bigger ones up there too, and over a few days I started to work through them. Finally, when I took my mums’ rabbit vibrator all the way up my ass, and was able to slowly ride it up and down, I felt like we were finally sharing an intimate connection. I liked to put them back without washing them, and I was hopeful that my mum wasn’t washing them either.

At some point, maybe around 14 or 15, I began trying to get in to my mate’s s****r’s pants again. He and I were still actively engaging in our regular sex fun, but he was no longer willing to let his s****r witness it or join in. I invited her over for a swim a couple of times, I began to feel a slight amount of sexual tension build up between us. A few accidental touches in the pool and seeing each other naked was enough to set the wheels in motion. The next time my s****r went to her friends after school, I sat next to my mate’s s****r on the bus home and invited her around for a swim. I convinced her to come straight over instead of going home for her bathers first. As soon as we got home my urges kicked in.

I took her in to my bedroom and casually suggested that we strip down to our underwear so we can go for a swim. I’m not sure what her expectations were, but seeing her in her underwear and knowing that we had a sexual history together drove me to get my dick out and walk straight over to her. It was easy getting her to grab it and give it a stroke, but she took some convincing before she would suck it. She was pretty bad at it anyway, but it was still a turn on. I helped her get naked and spent like an hour munching on her pussy and ass. We did this quite a few times, to different degrees and we even tried to fuck a few times. Every time my dick almost went inside her she had to stop me, but it was fun.

This new-found pussy action made me want more. My mother was my immediate choice, but I always saw her as being off-limits to me. Even though she clearly had a high sex-drive and a dirty mind I was pretty sure she’d never fuck me. I’d given her lots of signs that I was horny for her. I often put her vibrators back in the wrong spot so that she’d realise I’d been using them. Sometimes on weekends I deliberately left a pair of her dirty knickers in my bed, so she’d find them when she washed the sheets. Even a crotch full of cum in her expensive lingerie that I ‘accidentally’ left right on my pillow didn’t trigger a response.

It would have killed me if my dad ever found out about what I was doing, and I have to assume that she didn’t tell him because I’m sure I would have heard about it if he knew! But despite the risks, I wanted to make it clear to my mum, without actually spelling it out to her, that I was very much turned on by her and that I wanted to fuck her. My last ditch effort involved letting her see me naked a few times. When I was alone with her, I’d take a shower and walk out naked, semi-erect, just as I heard her walking past. She generally took it well, refusing to say or do anything that might give me an opportunity to turn it in to something it wasn’t.

The last time I tried it, I caught her looking at my cock, and she knew it. Once we both realised what had happened I’d become completely erect, and despite the obvious embarrassment, she laughed it off and told me to start using a towel. I tried to argue that I didn’t care if anyone saw me naked, but she didn’t except my argument. If we were ever going to cross the line, that was the time to do it.

So at that point I realised that after seeing my ridiculous effort to show her my dick, and after finding out that I was using her vibrators and masturbating in her panties, my mum still wasn’t willing to make the move, and neither was I.

So it had to be my s****r.

A few days after my realisation that I would never have sex with my mother, the school holidays started. I knew I was going to be home alone with my s****r for nine or 10 hours a day for 2 weeks, and I decided I’d see if she was interested in playing sex games with me. I’m not sure why I thought she would, but I’d been using her dirty knickers for years and I had always found her pussy scent to be by far my favourite. And I knew she’d be much more impressionable than my mother had been.

So Day 1 of the holidays started pretty normally. I had my s****r on my mind but I was too scared to make a move. While she watched TV I instead decided to take a few of our mum’s sex toys in to my bedroom for some fun. As I got hornier I became confident that I could have my way with my s****r. So I got dressed, put the toys away, and made my way to the lounge.

Any plans or tactics I’d considered were irrelevant at that point. I was horny, and after about a minute of pretending to watch the TV I stood up, and walked towards her. She noticed me walking over with a serious look on my face, and f***ed out a laugh despite the slightly worried look on her face. As I got closer I reached in to my pants and pulled out my erect cock, pulling my shorts down a bit to make room for my balls. I put it right in front of her and asked her if she’d seen a guys dick before. She said something like ‘not really’ and I encouraged her to have a look. It took a while to get her to touch it, but eventually she let me grab her arm and put her hand on it myself, and she was then happy to have a bit of a stroke and a squeeze.

When I asked her to ‘show me yours’ she got all embarrassed but agreed to let me be the one to expose her pussy. She stood up and I put my hand down the front of her pants, grabbed on to the top of her knickers and pulled everything out and slightly downwards, giving myself a sweet view of her tight little vagina. She was quick to pull her pants back up, but I persisted and eventually I just pulled her pants and knickers completely off her – in a very jovial, ‘no big deal’ kind of way as we both laughed like it was an innocent game. Once she was pantless I took off my clothes then asked her to take her shirt off. Again she resisted but was happy to let me take it off for her.

I asked her to sit and I knelt down between her feet. I immediately pushed my face in to her crotch and started licking her out. She went with it, and let me have a good long lick with minimal fuss. She was definitely uncomfortable, but there was also a sense of trust and understanding between us. When I lifted her legs up and licked her ass she was visibly disgusted by it! But I didn’t care, I was extremely attracted to both of her holes and I wasn’t afraid to show it.

When I stood up and put my dick near her face she looked worried. I don’t think she was at all surprised when I asked her to suck it, but she was still a bit freaked out. Regardless, she knew I was serious and opened her mouth and let me stick in the head of my cock in. She had no idea what she was doing (nor did I when I was going down on her) but it felt amazing to have my s****r naked in front of me with her lips around my cock. We went back and forth a few times, going down on each other and pretending that what we were doing wasn’t weird!

I taught her how to 69, and enjoyed long periods of licking her pussy and her butt while she licked and sucked my dick.

The next day, I got up early and suggested to my s****r that we watch one of our parent’s porn videos. I picked out the R Rated movie and made her promise to keep it a secret. About 5 minutes in I got naked and started pestering her to get naked too. She took a long time but eventually stripped off. I asked her to watch the women sucking cock, and got her to practice on me. She was getting better but in her defence I had a pretty big cock for a girl her age. We had a few short sessions throughout the day and I asked her if she’d be interested in doing it with my mate, who she knew well. She agreed and the next day he came over with his s****r. He knew I’d been doing it with her, but we kept it from his s****r. We paired off and had some naked fun together, although I would have preferred to be in there with them!

Later in the week, I asked my s****r to see if a friend of hers would be interested in joining us. It was a crazy thing to ask and could have exposed us, but luckily her friend was in to in, and the next day I had both of them naked in my bed, taking turns sucking me off and both laying there while I licked them out. It was an amazing situation and it was the first time we’d let anyone witness our i****tuous acts.

The next week the three of us plus my mate hung out at our house almost all week. He and I wouldn’t let them watch us suck each other off, but we both enjoyed watching each other get sucked off, and I had no problem openly licking out my s****r in front of them. Similarly I quite enjoyed having my s****r suck me off while they both watched. It was fucking epic.

This lasted about another 3 months, in various combinations. It kind of fizzled out but my mate and I continued to play for years after that. Once or twice I successfully cracked on to my s****r again for a sporadic session but the last year or two of my crazy sex life was just me and my mate.

One final twist and incredible experience was when I found a home-made sex tape in my parents’ bedroom. For the first time I didn’t have to imagine my mum having sex or using her vibrators, because it was all on tape! And it was dirty too. Seeing her masturbate, fuck herself with her vibrators and suck off and fuck my dad was unbelievable. But watching her pissing on the floor of the bathroom and letting my dad stick a small vibrator up her ass was a whole new level.

It was so hot I had to share it. I knew my mate would go crazy over it, so I showed him an edited version with as little of my dad as possible. I didn’t want to betray my dad by exposing his private life, but my mum was too hot to keep to myself. In the heat of the moment, I decided to show him my mum’s vibrator collection. We took great pleasure in licking and sucking her toys as we watched her fuck herself with them. It was beyond erotic and felt like the dirtiest thing we’d done. For the first time in years we were inclined to kiss each other like we were lovers. We licked, sucked, kissed and moaned like never before, and I showed him that I could fuck myself with her rabbit vibrator too. Once my ass was loose I let him stick his cock in me. I couldn’t take a pounding but it was nice to have him inside me. We must have made each other cum four or five times that day.

Obviously I’ve never been the same since those days. I’ve certainly calmed down a lot but I still enjoy the occasional panty raid and finding a woman’s vibrator still gives me thrills. I still fantasise about fucking my mum and the memory of playing sex games with my s****r turns me on greatly. These days my biggest release involves all night sessions alone, dressing up in my girlfriends clothes and my collection of other women’s underwear and clothing while watching dirty porn, including peeing, i****t, gay porn and tranny porn (thanks a lot, dad!).

100% (9/0)
Posted by thedildoguy
2 years ago    Views: 1,212
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1 year ago
wow great story... I cummed when you got to the part where you seduced your sis.
2 years ago
wonderful story.
2 years ago