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When was I nineteen I wanted to try everything. Sex was still new, and so exciting, and I wanted to experience all of it. I was eager to try anything I saw or heard about, so when my best friend Melissa told me her boyfriend wanted to try anal sex, I was intrigued.
Melissa said he wouldn’t stop talking about it, and that it was freaking her out. Melissa was scared it would hurt, and she just didn’t like the idea of it. But I was curious, naturally, and I thought I could help her. I told her I’d try anal with Tom, my boyfriend at the time, and that I’d let her know how it was, and if she should give it a go. What else are best friends for?
I thought Tom would be eager, but when I told him I wanted to try it, he was aghast. He said straight people didn’t really have anal sex in real life, that it was something you saw only in porn, like moustaches. He said it was disgusting and sordid, and that he’d never do it. He refused to have anal sex with me.
I agreed with him. I thought it was disgusting and sordid too, but that made it all the more alluring. I love to break the rules, to do naughty things I’m not supposed to, and the idea of him putting his cock in such a wicked place was super hot. It’s the sort of thing that’s so sexy and rude, religious people try to ban it. So it must be good, right? I’m also a stubborn contrarian by nature, and Tom telling me I couldn’t have bum sex was like a red rag to a bull. I’d never thought about anal before Melissa mentioned it, but suddenly I was keen for it.
And over the next few weeks I thought about it more and more. I couldn’t get the idea of Tom fucking me there out of my head. I asked him again if he’d give it a try, but he refused to even talk about it. He said he couldn’t understand why anyone would want to do something so dirty and depraved. I got so wet when he said that.
I was determined though. I read articles online about how to do it, I watched porn videos, the amateur ones where the guys use their fingers and tongues first, and go slow until the girl is warmed up, and it looked like fun. It got me even more desperate for it. I bought a tube of cherry flavoured lube from a sex shop in preparation.
I’m up for anything, but I also believe in careful preparation, so one night when I was in bed, I stuck a finger up my bum. I thought it would be sensible to start small and to try it by myself first.
I felt so tight I could barely get my fingertip in though, and I lost heart. I’d never be able to get a prick up there. It was madness. How did anyone manage it? I almost abandoned the whole idea.
But I’m determined. It’s one of my best qualities. I pressed my vibrator against myself, and I wiggled the finger around a bit, and I felt myself relaxing. I pulled my finger out and covered it in lube, and it went up much easier. Way easier. Lube people! Lube those backdoors! I eased my finger in deeper and it didn’t feel too bad.
I practised over the next few nights (I did say I was determined), and I managed to get three fingers up my bum. I used my vibrator as I did it, and I came much harder than usual. I think it was partly because it made me feel so naughty, but there was something physical too. It felt good. Being filled there heightened the pleasure from my vibrator. I really started to see the appeal of anal sex. I felt so proud too. Three fingers!
I got really into it. I wanted to see how far I could go. I managed three fingers and a thumb, and then I really pushed on. I actually got the lubed handle of one of my hairbrushes up my bum. It was a slender, smooth, tapered handle, so a good shape, but I got it really deep. I imagined it was Tom fucking me as I slid it in and out of my arse, and I came with such force I had to put a pillow in my mouth to muffle my screams and not wake the whole house up. I absolutely had to try it properly. I was ready and willing.
My parents went away the next weekend, they often did, and I was left home alone. I invited Tom over and I was giddy with excitement. I knew how to relax myself, and his cock was much bigger than my hairbrush handle, but I was confident I could take him. I was dying to try it and I wasn’t going to take no for an answer.
I danced around Tom and teased him with my body all Saturday afternoon. We kissed and groped each other, and it got heavy, but when I told him what I wanted him to do to me, he got annoyed. He said he was sick of hearing me talk about it. He crossed his arms and sulked.
So I begged. I was desperate. I’d been thinking about it so much, and all that practice, I couldn’t let it go to waste. I actually got down on my knees in front of Tom. I promised him I’d give him as many blowjobs as he wanted all weekend. I said he could come on my face. I kept on and on at him until Tom eventually said he’d do it just to shut me up. That we could try it once, but just once, and then I couldn’t ever mention it again.
He didn’t look very happy about it, and I did feel a bit guilty at that, but I was too excited to let it stop me. I told Tom I’d prepare myself first. That I needed to wank with my vibrator and finger my arse. He shook his head at me as if what I was saying was too bizarre to countenance, but he followed me upstairs to my bedroom.
Tom sat on the chair in the corner and I stripped for him. I gave him a real show, and he sat forwards and grinned at me. His eyes drank in my body as I exposed it to him, and it really turned me on having him study me so intently. I was going to kiss him a bit to get myself in the mood, but him looking at me like that, and the idea of what we were about to do was more than enough to heat me up.
I slipped out of my knickers, then I picked up my vibrator and I laid on my bed with my legs open. I’d masturbated in front of Tom before, but I’d felt too self-conscious to really enjoy it, but that evening I was so turned on I really got into it. I was soaking wet before I even touched myself, and when I pressed my buzzing vibrator against my cunt, I knew I was going to come quickly.
I tried to hold back though, at least until I was ready for his cock. I laid on my back as I started, but I squirted lube all over my free hand, and I rolled on my side as I rubbed it between my cheeks. I pointed my bum towards Tom and I opened myself up wide so he could see what I was doing. He tutted and he told me he found the whole thing disgusting, but I looked over my shoulder at him, and he was watching intently. I like being disgusting too.
I shivered and moaned as the first of my fingers slipped in easily up to the second knuckle. I twisted it as I slid it in and out, and I worked it in deeper as I relaxed around it. I moaned louder and writhed, partly for Tom, partly because it felt good, but also because it was so gloriously dirty to masturbate and finger my arse in front of him like that.
I rolled over onto my front, and I tucked my knees under myself to raise my arse up. I spread my thighs and I knew Tom could see everything, the vibrator pressed against my sopping pussy and the finger slipping in and out of my arsehole.
As I worked a second finger into my bum, I glanced over at Tom and the look on his face made my cunt and my arse clench. It was a magnificent mixture of revulsion and disbelief and fascination, and I lost my head a bit.
I managed to get a third finger up my bum, and I pushed them deep. I was so turned on I really went for it. I worked them in an out of me quickly, and I hadn’t planned to, but it was close at hand, so I took my fingers out and I lubed that hairbrush up too. I worked it into my arse and I fucked myself with it.
I peeped over at Tom again and his cock was in his hand and he looked wide-eyed and totally enthralled. I couldn’t stop myself from coming then. It was so naughty, and the look on his face, it was all too much. I came so hard I thrashed around and made lots of noise, and I pushed that hairbrush really deep. It would have been embarrassing if it hadn’t felt so good.
When I’d finished, Tom stood and came over to the bed. I got up and took his cock into my mouth, and that hairbrush was still up my bum.
I sucked Tom until he started moaning, then I got hold of the lube again. I sat back and covered Tom’s cock in it until it was dripping and glistening. I laid down on the bed and spread my legs. I slid a pillow under my bum, then I looked Tom in the eyes as I slowly pulled the hairbrush out of my bottom. I asked him politely if he’d like to fuck my arse.
After all that, Tom gave me a look like he was thinking about it, the absolute dickhead. He stood over me with his cock in his hand, and he didn’t move. I was more turned on than ever, and my arse was actually feeling empty, like it needed something up it, and I squirmed and whimpered for it. I begged him to put his cock up my bum, and Tom eventually yielded to my pleas. He told me that I was a lucky girl. That he was going to give me what I wanted. He was loving teasing me.
I got my hands behind my knees and I pulled my legs back and rolled my hips up to properly offer myself to him. Tom stepped forwards and pressed the head of his cock against my sphincter and I groaned at just the touch of him there.
But then he stopped. He grinned down at me and he told me I had to beg again. I was frantic by that point, and without shame. I’d just fucked my arse in front of him with a greased hairbrush handle, so I wasn’t feeling proud. I pleaded without a shred of dignity. I begged him in my whiniest voice to fuck my arse.
Just at the point where my need was becoming frustrated anger, Tom pressed the tip of his prick into my bum, and it silenced me. It was just the very end of him, but he stretched me, he felt huge, and I had a moment of panic. I was scared he’d be too big to take. But then I saw the look on his face. It was that mix of disgust and fascination from earlier, but there was pleasure now too, and I quivered and groaned. I felt myself relaxing around him and I wanted it more than ever.
I told Tom to keep going, but slow, and I took deep breaths and focussed on staying as relaxed as I could as he eased his prick into me. He felt impossibly huge and much longer than usual. He kept stopping, and each time I thought he was in me all the way, but then he started up again and more of him slid into me.
Tom kept coming and coming, but I took steady breaths to calm myself, and I managed to take all of him, what a champ! Sweet baby Jesus though, he stretched and filled me like I’d never been filled before. I was stuffed. I was panting and gasping, but it was so sexy too, to do something so bad, and to be so filled up. I watched his face as he did it, and it was screwed up in pleasure as if this felt better than anything, and maybe it did.
He asked me if I was OK, and I was, and much more, so I told him to fuck me. He eased out a little, then pushed home, and that feeling of being stuffed came on stronger. He eased out a little further, then came back into me all the way, and it was too much, suddenly he felt far too big, and the panic was back, and it was overwhelming me.
I told Tom to hold still, and I was the verge of totally freaking out, but then I remembered my vibrator. I found it next to me on the bed. I switched it on and held it against myself, and it gave me something else to focus on. I got my breathing back under control, and everything started to feel a little better. I pressed it against myself harder and that cock up my bum wasn’t so bad. It began to add to the sensations from my vibrator. I told my boyfriend to try fucking me again.
Tom did, but he screwed me so slowly and carefully and gently, bless him. He watched me to see how I was doing, but it looked like he was holding himself back, that it felt good, and he was struggling to control himself. He groaned louder than I’d ever heard him groan, and his eyes fell to the spot between my legs were his slick cock was sliding in and out of me, and he looked riveted. For all his prudish protestations, he was loving this, the hypocritical little filthbag.
And it felt good for me too. I rubbed my breasts and pulled my nipples, and I stroked my overly-sensitive clit with my vibrator, and it started to feel really quite good actually. It helped too that I was so turned on from my wicked display earlier, and that what we were doing was so naughty, and how much Tom was enjoying himself, and that he’d made me beg for it, and it just felt really fucking good too. Waves of pleasure rippled through me and joined those coming from my clit, and my thighs started trembling, and I started moaning and groaning like a rutting animal.
Tom started to lose himself to it was well. He moved faster, he slid out further with each stroke, and the look on his face became a sort of angry delight, like he was appalled that he was doing this, and even more so that he was enjoying it so much.
He groaned louder, and he moved faster and faster, and even after all that practise, I’d never have thought I’d be able to take it like this, but it got better and better. It slayed me to see him like that too, loving it, but revolted at the same time, it made what we were doing feel even more dirty and primal, and I realised I was going to come again. And then Tom asked me where he should finish, and it was all a bit overwhelming.
It’s such a delightfully wicked question, so full of naughty possibilities, and Tom knew full well how much I loved being asked it as he fucked me. I gasped, and visions flooded through my mind. I could take him in my mouth, and that would be so wonderfully filthy, to suck his cock after it had just come out of my bottom. I could tell him to finish over my face, that was the place Tom liked the most, and it would have been a treat he’d more than earned. I had an even naughtier idea though. I told Tom to come in my bum.
He looked even more disgusted, but he didn’t stop. He fucked my arse harder, his noises rose in pitch, he screwed his face up, and then he shuddered and groaned loud and he was coming. He pressed his cock deep and I felt it twitching inside me as he filled my arse with his come.
It was the straw that broke the camel’s back for me. How could it not be? It was by far the dirtiest thing I’d ever done, and I came hard over it. I screamed like a banshee and I pressed myself against Tom’s prick as it spurted up my bottom.
I told Melissa all about it, and how good it was if you prepared yourself, and used lube, and a vibrator for your clit, and took it slow, but she said it didn’t sound like her sort of thing. She never let her boyfriend fuck her arse, poor chap.
Tom did it again to me though. He did it frequently. He’d protest, and he’d say he didn’t want to, but we both knew it was part of the fun. He liked to pretend he was above such things, but really he loved to see me beg for it. And he never comes as hard as when he comes up my bum.
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If you've enjoyed this story, then we've recently published our second collection of erotic confessions on Amazon (it contains this one). The confessions include sex with strangers, sex with lovers, lesbian sex, oral sex, anal sex, voyeurism, and domination and spanking. Some are wild, some are even wilder. Explore more on the link below: