I love a good first time. Not just first time sex, but the first time I do anything that’s fun: driving on the motorway, eating halloumi and wondering where it’s been all my life, swimming topless in the sea, etc. There’s a lot to love about that initial kick of novelty.

This post isn’t about my own first times, though, it’s about those of other people. Because, although I have only ever had one guy’s virginity (which was very willingly given), when it comes to anal sex I’ve taken a few more.

Not naturally dominant, strapping on a dick and holding a guy’s legs up to his chest while I fuck him is something of a nervewracking experience. What if I’m not the kind of awe-inspiring dick-wielder I dream of being? What if he decides he doesn’t like it, and his memory of me is forever tainted by the disappointment when his prostate didn’t thrill with joy? Well, via the medium of Three Stories About First Time Pegging, let’s see, shall we?

The enthusiastic

This section is an extract from my book – if you’ve read it just skip to the next subhead. 

He lay on his back on the bed, naked from the waist down, and I could see how much he was looking forward to this. His cock stood straight up in the air, solid and thick and glistening at the tip. I pushed his knees up towards his shoulders, knelt on the bed between his splayed legs, then wet the tips of my fingers and traced them around and around the head of his cock.

‘Do you want me to fuck you?’

He nodded.

‘Tell me. Tell me you want me to fuck you.’

‘I want you to fuck me.’

‘Say please.’ I reached for the lube as he babbled, desperately.

‘Please fuck me. Oh please fuck me. I just want to feel you in me, I need to come.’

I had one hand on his dick while my other hand squeezed the best part of half a tube of lube onto my own.

Although it wasn’t something I’d fantasised about, something intangible about this situation made me tingle with arousal. There was no pain, no spanking. I wasn’t being submissive. I was just kneeling between the boy’s legs, pressing the tip of my fake dick right up against his ass, and yet something was giving me that lustful kick.

‘Touch your dick.’

He obeyed immediately. Quivering with lust and nervous about being fucked for the first time, he stroked himself slowly, not wanting to come before I’d had him. He was close enough to coming just from the anticipation of what we were doing, so when I slid first one then two fingers inside him he tensed up.

‘Ah, no, please.’

I stroked his prostate, very gently, and felt every muscle in his body tense as he tried not to come. I’d never been so powerful. ‘You’re going to come when I fuck you.’

‘Yeah.’ He nodded a few times, more a reflex twitch than a nod of agreement. He stared at me with wide eyes and bit his lip, as I used my lubed-up hand to guide my dick into him. He groaned.

‘Does it hurt?’

‘Yes. But it’s good.’

‘How good?’ I tentatively slid it back out, then in again, a bit further this time. Another groan. A twitch.

‘Good.’

And I knelt up, put a hand on each of his raised knees, and pushed them backwards, opening him up and pushing him back, as I slid in and out of him. His face was tight in an expression of both pain and ecstasy, knit with concentration in an effort not to come. But I wanted him to come. I knew that the build up and the nervousness and the panic and the joy of being fucked in a whole new way would lead to an orgasm that shot from deep inside him, spraying mouthfuls of spunk over and across his whole body.

I fucked him harder, and I grabbed his dick, and it happened exactly as I’d hoped: he shot ropes of spunk that hit not just his chest and face but the wall beyond his head. He moaned and cried out, his stomach tensing as he did and he raised himself up slightly towards me. I felt a slight movement on my dick as his ass tensed with the impact of the orgasm, and his own cock jerked violently in my hand.

The disappointed

“It’s… ow. Fuck.” He furrowed his brow. “It’s harder than I thought it would be.”

I knelt over him, red straps at my waist and frustratingly unfeeling cock about an inch deep inside him.

“Perhaps a different angle?” I suggested, shifting slightly. I don’t know why I cared so much but I really wanted him to like it. After helping the first guy reach the kind of orgasm he’d never had before, I wanted this next guy’s reaction to be the same. A wide-eyed ‘oh God it hurts but please don’t stop’ building to a shuddering, twitching, frowning climax and spunk plastered liberally over the head of the bed.

“I’m not sure.” He twisted again, trying to get it in further at a different angle. I pushed it in.

“No. Fuck. Argh.” I pulled out. He clamped his legs together reflexively. “I don’t think I like it.”

I held his dick, massaging lube from the base to the head. He moaned softly, and his frown faded.

“Maybe we should try again?” I shook my head. The fucking itself was pretty hot – feeling the power of being above him, on top of him, controlling his pleasure with every inch of my fake cock. But that feeling only worked if there really was pleasure. I wanted to fuck him into that kick of joyful novelty, to give him something new and filthy, not to tease and encourage him into it the way you would persuade a fussy eater into broccoli.

I didn’t want his face to tell me ‘ow. I hate it. It hurts’ – I wanted ‘that’s it. More. Please.’ So I grabbed his dick with my hands and made that face happen instead.

The best response to first time pegging

You know what the best one is, right? The best is a guy that takes that enthusiasm – that desperate horny lust – and begs for more of it until I can fuck him with power and force and the kind of all-out brace-yourself energy that he’ll aim for when he’s fucking me.

And that’s exactly what happened.

With the third guy, I knew he’d been wanting it for a while. Playful conversations about me fucking him had led not to giggles or ‘maybe’s but to a very open, certain ‘yes please.’ A bold declaration that he knew this would be good. And it was.

He was blindfolded, strapped by the wrists and ankles to the bed frame. I’d lubed up his cock, with the aim of testing some new wanking sheaths and seeing if I could do the kind of teasing denial-play that he’d spectacularly fail at if he weren’t restrained. Lacking imagination, and basing most of my proactive sexual moves on the things that appeal to me, I thought he might enjoy being bound and filled to stretching point with cock.

I put a plug in him and instructed him to push down onto it. He squirmed, bucking slightly, enjoying exactly that ‘filled’ sensation while I put on a harness and cock. I unstrapped his ankles from the bed, lifting his legs up and back. I pulled the plug out and he moaned.

“Are you getting ready to fuck me?” No fear, no apprehension, just raw excitement.

“Yes. Do you want me to?”

“God yes.”

I slipped into him slowly. My memories of the second guy had made me cautious, wanting to give him time to adjust and relax as I fucked him with very slow strokes. Instead of wincing, however, he urged me on – more, harder, deeper. He shifted position, pulling his knees closer to his chest so I could get my dick further into him.

“Do you like that?”

He answered with a nod and a guttural moan, then twisted around to part his legs further. Nothing tentative about it – he wanted something no one else ever had: a first time pegging that was full-throttle. Power and speed rather than a gentle introduction. My hands gripping his hips and him bucking and writhing onto me. The full length of my fake dick and my lubed-up hands on his. The ache and pain and lust as I slammed it with force deep inside him: a first time pegging that felt like a practised fuck.

Want to buy a strap on so you can do this too? If you buy sex toys through the affiliate links included in this post, I make a bit of ££ to support this blog. 

When I first started getting into sex – and I mean really into sex, past the initial ‘oh bloody hell this is awesome’ stage and into the ‘I wonder what it would be like if I did this unusual thing’ phase – I gave butt plugs a fairly wide berth. Hitting implements: fine. Vibrators: no problem. Role play: as long as it wasn’t too funny. But butt plugs seemed like a strange and unusual thing.

I love anal sex, but the main reason I love it is because of the whole atmosphere – his grunting, delicious desperation as well as the feeling of his dick meeting tight resistance. Butt plugs seemed a bit pointless: I don’t have a prostate, so why would I want one there? What’s more, I felt a teeny bit nervous about using one on a guy. Worried that I might do it badly and it’d either be totally underwhelming or – worse – hurt.

As with many things, I was spectacularly wrong.

Sit

We talked about it first. He told me that he liked it: that feeling of being full. My head was full of pictures: him lying on the bed, naked from the waist down, reaching to push something firmly into himself. Him: sitting at his computer, with a plug snugly inside him and braced against the seat of the chair, frowning in concentration as he rubbed himself to climax.

I wanted to see that first hand.

“Are you going to use that on me?” he asked. I waited for a while, putting on the kind of face that covered my nervousness with controlled indecision.

“Nope.” I put it on the chair. “You’re going to use it on yourself.”

Stay

Watching him lube up the plug then wince with concentration as he slid it into himself was just the start. As he sat down slowly onto the wooden chair, his face displayed a beautiful tortured dilemma: ‘I like this. It feels good. But I feel so dirty.’

“How do you feel?”

“Dirty.”

“Touch yourself.”

He gripped his cock firmly and started sliding his hand up and down. He twitched and trembled with a combination or nervousness and arousal. I could see the tension in his neck, and the taut effort in his thighs as he tried not to rest with too much pressure. He didn’t want it in too deep straight away – he wanted to take it slowly. He swallowed, rubbed harder, relaxed a tiny bit. Let the plug slip slightly deeper into him.

“How do you feel?”

“Still…” he rubbed harder “…dirty.”

I sat on the edge of the bed getting hot at the sight of him. It was his face, mostly. The flickers of competing expressions and emotions as he stroked himself towards a climax that he was both desperate for and ashamed of. I couldn’t believe there could be such a difference between watching him wank and watching him wank like this: with a plug holding him firmly in a place where he was conflicted about his joy.

I had rarely wanted him more.

Good boy

I stood over him and pulled the crotch of my knickers to one side. He looked up at me and I gave him the kind of grin I’d usually save for afterwards: gleeful, ecstatic, overjoyed by this intensely new thing. I loved that this boy was so utterly on edge – aching from the plug and tingling through his dick and desperate to come right in front of me.

I straddled his legs, wrapped my arms around his neck, and lowered myself onto his cock. Gently, for the first few strokes, I slid up and down him – my cunt getting wetter and hotter at the sounds of his plaintive moans.

“Please.”

“Please what?”

“Please… harder.”

“Fuck you harder?”

“Yes.”

“You want to feel me fuck you hard so this plug is pushed deeper into you?”

“I… yes.”

“Say it.”

“Please fuck me harder. I want to feel it inside me. Deep inside m… Oh God. Fuck. That deep inside me.”

So I fucked him harder – much harder. I rode his dick in a swift, jerking rhythm, grinding his arse into the chair and the butt plug deeper inside him. I rocked back and forth so he could feel it pushing against the inside of him from all angles. I gripped the back of the chair and pulled on his hair as he cried out. I felt the tension in him every time I slammed down to the base of his cock – the solid, hard strokes that drummed the base of the plug against the chair, and the tip of it into the boy.

There are other stories to tell about butt plugs – when they’re used on me, or other ways I’ve used them to make guys whimper. But this was one of the first introductions I had to butt plugs. From this point on, the main thing I associate them with (and the reason I always keep a couple of different types in my sex toy drawer) isn’t the play itself – the specific acts or moments or even the feeling as one is slipped inside – it’s the expressions. The looks of lust mixed with uncertainty and a heavy dollop of need. It’s filthy not just because he likes it but because of the way he likes it.

Finally, too quickly, before my thighs could even think about aching, he came. One final grunt of satisfaction and anguish and lust, and his cock twitched hard inside me. He buried his face in my chest and offered a wholly unnecessary “thank you.”

As with any toys mentioned here, you’d be helping to support my site by buying butt plugs from my affiliates using any of the links on this sex toys page. If you’d like a specific butt plug recommendation, my favourites at the moment are these Doxy butt plugs – buy direct from Doxy using my affiliate link and you’ll get 15% off and free shipping if you use the code GOTN15. 

In a fit of rashness, I recently wrote about how anal sex isn’t just hot because of the purely physical sensations. Most sex is – to my mind – enjoyably filthy because of how you do it. Exactly what you do matters less than the dominant, eager way in which you do it. You can wank me off in a way that both of us find tedious and uninspiring, or with the addition of a few dirty words whispered in my ear and one arm gripping me tightly around the chest, you can rub me off in a way that feels close and filthy.

But, in explaining how sex isn’t just about physical reductionism, I missed a key opportunity to talk about how some very specific physical things make me tense with swooning lust. Today I’m going to talk about feeling full.

Three dudes at once, obviously

The dream, of course, is to have three men at once. Something which, despite my very best efforts, hasn’t happened yet. To have one guy filling my cunt while another pushes deep into my arse, and a final man pushing his dick so deep in my throat that I can barely choke new oxygen down to my lungs.

While I’m enjoying being gagged by one guy, the other two can feel not only the aching throb of my cunt and arse, but the taut force of each other’s dicks, sliding together through my own skin. They fill me so I cry out, and push back onto them – wanting to experience the full length of each of them, as deep as they can possibly go. They fill me so I can’t remember what it felt like to be empty. Until I can’t believe anything else will fit. And then, as one, they come inside me. Vigorously pumping spunk into anywhere it will go, proving that I was ever so slightly easier to fill than I thought.

Sadly, this dream of feeling full of cock will have to be put to one side for now: the logistics of finding three willing men, all of whom I fancy and all of whom fancy both me and each other is a challenge that I am yet to conquer. Besides, double penetration looks easy in porn when all the actors are lithe and athletic and don’t seem to mind one dick slipping out every now and then. In my fantasy this can work exactly how I want it to, with none of those pesky physical limitations to get in the way.

“I can come like this”

In the meantime there’s always option two: the late-night lazy fuck that sees me lying on my stomach, being fucked hard from behind. I can grip the iron bars at the headboard and push back to feel his thick cock stretching me open. I can hear the squirt of lube as he covers his fingers, and feel achingly full as he pushes them into me.

A long time ago a guy did this, during the very last fuck we ever had. He pushed two fingers deep into my ass and groaned as he felt the solid length of his cock through my own skin. His fingertips rubbed the inside of me, simultaneously pressing onto the ridges around the head of his dick. Back and forth, faster and wetter and slicker, as I moaned at the feeling of being full. As he moved faster and faster, rubbing at both me and himself, he grunted, and exclaimed with delight: “I can come like this. Just like this.” A few more back-and-forth movements, the twitch of him deep in my cunt, and I felt all the excitement pour out of him and into me.

I still regret that it was the only time he got to do it. I’d have loved to have more fucking stories that involve him revelling in this new trick, testing new and different ways to jerk himself off through my ass, as I writhed in fullness and squealed delight into the pillow. If you’d like to try doing this but you don’t know anyone to try it with, I’m told there are double-holed masturbators that you can penetrate with both your dick and either your fingers/another object of your choice that will allow you similar sensations.

Filling fucks between just two people

The fingers are hot because he can control the sensation – other things are hot because I can control them myself. The feeling of being full doesn’t always require a stable of willing men or a guy who knows how to use his fingers in just the right way. This is one of the places where a well-made and perfectly shaped sex toy has not just a place in my bedroom but pride of place nestled deep inside me.

Sitting dead still on someone’s cock is fun – the moaning, twitching, desperate need for movement and sensation gives me a feeling of total power and control. I could grind slowly, I could clench all the muscles inside my cunt and watch his eyes grow wide as he feels the whole of me squeezing – hugging – his dick. Even more fun, then, to hold him tight in that position, gripping him with force and power, then slowly push something deep into my ass. Something long and slim, that I can control easily. Something that buzzes and vibrates against the length of him. He can feel what I’m doing as I push it deeper, as I angle it so it shivers down the full length of his cock. And as I do it, I squeeze harder – the better to revel in that full-up sensation.

But having the power is a rare delight – something that’s only fun for me because it happens so infrequently. Far more enjoyable, I think, to have him on top of me – bearing down. The fullness is better when someone else is controlling it, and I’m begging for more of it. His dick in my cunt anchors me in place – I squirm and wriggle on it as he pushes something slim inside my ass. Then something bigger. Then, with a growling whisper, he asks me if I can take more. If he can swap it out for the third most filling item in the trio. Despite knowing that it won’t fit, I’ll always say yes. Please. Do it. Try it. I’ll fail, yet again, but the temptation of finding something that stretches me out to the point I know I can’t feel fuller is just too much to resist.

When I fail at the largest one, we’ll step it down again, and I’ll enjoy knowing that I very nearly made it.

Can you come from ‘filling’ sex?

Does it make me come, though? This specific, hot, physical sensation? Of course. Although there’s nothing biologically that says ‘this will thrill the nerve endings in just the right way’, the feeling of being stretched and full adds to all the other things that are going on – the sensation of his dick pushing against the inside of me, the sound of him breathing heavily, telling me I’m so good for taking it. The gentle slaps on my arse, sucking bites at my nipples, rough hands gripping my hips to pull me further back onto him. All of these build, one wave on top of another, eventually pushing me over the edge of arousal and into that rushing, twitching, gagging choke of orgasm.

My final, and favourite trick is the one that brings me there most quickly: crouched on my knees, with my face pushed hard into the bedsheets, his dick dripping with lube and deep inside me, and my hands working busily to push something hard into my cunt. A rabbit vibrator, usually. Despite it’s often twee connotations, it has exactly what I’m after: length and girth to fill me up, and the added bonus of a vigorous buzz directly against my aching clit. I’ll hold it there, right up to the hilt, a still and solid anchor to clench down on, while he fucks up hard against it until he comes. 

This post uses affiliate links, which means if you buy things from the shops you visit, I get a small cut which helps me keep this site running.