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. 

Yesterday I promised I would take questions from anyone and then answer all of them. This was initially a bit scary as, given my lack of any other redeeming features, I use my mystery as a way to cultivate a vague sense of allure. So I am aware that any question about love, emotion, or things other than my cunt will rip away just a tiny bit of that mystery and make me a more relatable, yet inevitably less exciting person.

Still, I was delighted by the sheer variety of what was asked: from strap-ons to sexy comic books, the hottest places in London and how to make your submissive gag, the sex blog questions you all submitted were incredibly diverse and very fun to answer. In no particular order, here’s the full Q&A. If there’s anything else you’d like to ask, or if you’ve got a better answer than mine, please do leave a comment – you can comment anonymously if you like.

How much effect does sex have on love, rather than vice versa?

I love this question, because it’s usually asked the other way around: “is sex better if you’re in love?” Here it seems like you’re asking whether I’m more or less likely to fall in love with someone if they are amazing in bed. To which the answer is: “oh holy God yes.” In fact, if you are stunning in bed, I am likely to fall in love with you even if you are a total arsehole.

This has got me into scrapes in the past when my rational mind has accepted that a particular guy is basically a bit of a tedious wanker, but he has done something so filthy-hot that I can’t keep my mind off him. If you’ve read my book, you might know which guy I mean.

I think we’re often sold a massive lie about sex and love, which is that love conquers all, matters more than sex, and that if we’re in love sex itself fades into the background and becomes meaningless and unimportant. This might well be true for some people, but it is not true for me at all. Sex enhances, drives, and impacts on my love in a very significant way: if I can’t fuck someone I will struggle to love them. If I fuck someone and it works perfectly, I will be convinced I’m in love with them.

This makes it very difficult if I have a relationship problem that’s primarily sexual (for instance, if I’m with a guy whose sex drive isn’t as high as mine) because I feel like I’m being unreasonable for making sex a primary issue, and I feel that I’m a bit wrong in the head for caring so much about it. My rational mind knows this is wrong – we are who we are, and we all have different priorities. So these days I am likely to throw a bit of a shitfit if someone tells me I should suck up my sexual frustration and just enjoy the cuddles.

Are there any missed opportunities that you regret?

Yes, a million. But only one that really stands out. Before I lost my virginity I was in love with my best friend. I lusted and ached after him for years, but he didn’t show any interest at all. I’d almost put all my feelings to bed when one day, out of the blue, he propositioned me. After a day of teenaged flirting he told me he was horny, and that I’d made him that way, and used a cheesy line to ask me: “what are you going to do about it?”

Adult me would leap upon that opportunity and hump it until its eyes rolled back. Teenage me had no idea what to do. She stuttered, and ummed and aahhed, and eventually suggested that we head back to the house to watch a film. I probably could have had sex with him if I’d played that right, but instead I settled for sitting agonisingly close to him while we watched some crap B movie about monkeys, and I swear to God he could probably hear the thudding of regretful lust in my cunt.

I’d love to see a blog on what you think of guys in bands. Just curious.

I think two things about guys in bands. Firstly, people who play musical instruments are badass-sexy, because they have a skill that I don’t, and I can watch their beautiful hands manipulating instruments in a way that I never could. If they can sing, my heart will crack and I will be in love with them for every single second they are on stage.

Secondly, people who are in bands are often music twats. And I use ‘twat’ here in the a very specific way to mean ‘someone who knows more than I do about something I couldn’t care less about.’ I know nothing about what I am going to patronisingly scare-quote “popular” music or “indie” music, or any genre of music, and if you ask me what I think of a particular band I will probably say “who?” then wander off and turn on Radio 4. I like a tune, and I like good lyrics, but if you try and recommend music to me my eyes will glaze over and I will nod along until I can reach for a gin to take the pain away.

So in conclusion: guys in bands are super-hot, and in fact anyone who can play a musical instrument gets a double-thumbs-up from me, but if you try to talk to me about music we will both be disappointed.

What would win in a fight between a wolverine and a honey badger?

Honey badgers always win, don’t they? I thought that was basically the point of them.

Filthiest, kinkiest, most depraved porn you’ve ever masturbated over?

I’m torn here – if I say something deeply depraved you’ll all think me an awful person, and if I say something relatively tame you’ll go ‘huh, but you’re a sex blogger – you must be the filthiest porn-watcher in the world!’ Such are the rocks and hard places of sex blogging.

I suspect that my porn tastes are relatively tame compared to many – I tend to focus on the sounds and the faces people make rather than the specific scenarios, just because I am a fan of any scenario that could be described as ‘pretty rough sex that all participants are demonstrably enjoying.’

But here are a couple of examples of slightly odder things:

• Sections of the children’s book Heidi – when I was younger any scene that involved corporal punishment in a school set me off.
• A video of a guy jerking off while wearing a nappy. I rubbed one out to that a few times. To be honest, the nappy didn’t do much for me (although it clearly did for him), the reason this video featured so highly on my ‘to wank’ list was because when he came he made an absurdly delicious grunting noise. Unngh.
• The most excellent milk video (link at the bottom of this post), which is still – to my mind – the best bit of porn on the internet.

Natural smell of a man or something out of a bottle?

Oh both – definitely both. The combination of hot man-sweat-smell and bottled uniqueness makes my head spin and my knees go weak. Initially I wanted to answer ‘sexy man sweat’ but then I remembered I’d once followed a guy round a shopping centre for about half an hour because he smelled of teenage sex and I couldn’t work out why. The answer, it turns out, was that he was wearing Joop. For similar reasons, a man wearing Hugo Boss will make me feel angsty and sad about University days, and have a desperate urge to shag some doe-eyed Uni student with a strap-on.

What is the best native mustelid?

Otters. They’re cute.

When I scratch it it bleeds, when I don’t scratch it it tells me to burn things. Should I continue to scratch it?

God no, just make sure you have lots of firewood to hand. Or some flash paper. Flash paper is fun.

Do you like to be the big spoon or the little spoon?

Little spoon. Can’t get enough of those late-night and early-morning boners poking into my arse.

Your thoughts on Sex Criminals (it’s a comic book btw, I wasn’t referring to actual people)

I have never read it, but having read the synopsis on Wikipedia, I might have to start.

I don’t have much confidence when it comes to sex, verbally/emotionally abusive boyfriends in my past left me unsure and afraid to ask/suggest what I want. How do I become more confident about asking for what I want (like spanking or being tied up or tying him up)?  How do I make it clear without making a guy feel like whatever else he was doing was no good?

Right, firstly, sorry you’ve had such horrible experiences in the past – although I firmly believe most humans are generally nice people who are doing their best, there are a number of total arseholes out there and it sounds like you’ve run a fairly harrowing gauntlet of them.

To answer your question – I think everyone responds to these things a bit differently, and I’d broach this topic differently with any partner just depending on how they tend to react to things and their overall character. But as a general rule, I find the best way to communicate about sex is always to emphasise the positive – make the absolute most of things you love, and make sure to tell him ‘holy fuck that’s hot’ whenever he does something ace. That way, you can give him a boost with loads of enthusiasm, and when you venture forth with ‘could you do this a bit differently?’ he’s unlikely to take it too badly, or feel like he’s doing everything wrong, because he has all the evidence of your ‘hell yes’ responses to other things he does.

Once you’re in that zone, it tends to feel a bit more natural to chat about the stuff you love. You don’t have to come straight out with ‘can I tie you to a radiator?’ if you’re nervous, but you can definitely start a more general chat: ‘what do you like most about what we do? Is there anything you’d like to do more of?’ and that can lead fairly neatly on to ‘I love this too – would be ace if we could try it a bit more like this.’ Having a more general discussion, and encouraging him to talk about this stuff, should help you build your confidence a bit. Does that help? If anyone else has suggestions, please leave them in the comments!

How do you get over someone who was really good in bed?

Ouch. That’s a tricky one. There’s one guy who I will never fully get over, partly because we were so sexually compatible that just thinking about him now gives me fuck-flashbacks. Again if you’ve read my book, you’ll probably know which one I’m talking about.

I can’t answer for everyone, but for me the answer was time – although we were (and still are) good friends, I can’t spend too much time with him, and ‘getting over’ him consisted of having the willpower and sheer bloody-mindedness to avoid seeing him while I got my head together, used my awesome cunt-powers on other hot guys, and getting myself to a point where I could comfortably sit in the same room as him without dribbling down my shirt.

Ways not to get over someone who’s really good in bed include: trying to find someone who is good in bed in exactly the same way. I gave this a bit of a go, by looking for guys who were bi-curious like he was, had similar body types, etc, and trying to persuade them to do similar things with me. This was a total disaster, because everyone has their own sexual style, and what’s hot is discovering the things they actually enjoy doing rather than encouraging them to do the exact things my ex did.

Do strapless strap-ons actually work properly?

That very much depends on what you mean by ‘properly’ – they work differently. I’ve tried one before that was a bit like this. I can get the bit at my end in, and I can hold it there, and I can sort of thrust in and out. But as far as I’m aware they’re supposed to be providing pleasure to me as well as the person I’m fucking with them, and my sweaty panic that it’s about to fall out coupled with the wobbly nature of the thing itself that means I can’t ram quite as hard as I (or he) would like, so I’m not personally a fan. In looking for that link, though, I have spotted this, which comes with an anal bit as well – I imagine that works as a kind of double-anchor that should make it a bit easier to keep in, so if you’re wedded to the idea of a strapless one, that might work quite nicely.

However, so that I don’t end up sounding down on strap-ons in general (I fucking love them, and I should do a full post about this at some point) I would recommend a strapped strap-on that also has a going-insidey bit (sorry to bombard you with technical terms) or a strap-on that doesn’t have anything at all that goes inside my cunt (I have something like this, but with a black harness, because it’s sturdy and the harness makes my arse look spectacular). To be honest if I’m fucking a guy with a strap-on it’s a fairly dominant thing, and I’d rather not be too distracted by my own desire to get frigged.

How can I make my sub gag without using my dick?

OK, so I would never presume to tell you what someone else would find hot – these are all just things I’ve enjoyed in the past. So if you are looking to follow any of this advice, I’d recommend discussing these with your sub beforehand, showing him/her this list, and working out which (if any) would hit their sweet spot.

As with all hot and violent BDSM, consent and communication is key. It depresses me that if I don’t explicitly say that I get comments from people saying “but you didn’t tell people they need consent!”, because I’d assume that all rational, decent humans would just fucking know. Anyway. Here are some ways I like to do gagging stuff, that might appeal to you too.

– fingers. This is a classic one, and basically just consists of ‘stick your fingers down their throat’. I have previously had guys do this to me while their dick is in me, because they enjoy the twitching of my cunt around their dick as I retch. But if you don’t have a dick, it still works for the gagging.

– dildo. Another classic, and one of the reasons why it’s always helpful to have a dildo on hand. The first time someone did this to me I didn’t understand the point of it: why am I going to suck off a cock that isn’t attached to a human who can feel it? Then he told me: “suck this right down into the back of your throat and hold it there while I beat you.” And I got the point pretty quickly.

– strap-on. See my above recommendations for strap-ons, and remember that they are not just for ladies. I know you’re a Dom, mystery questioner, but if you have any submissive tendencies at all, I can thoroughly recommend being made to wear a strap-on over your actual dick, and being forced to screw someone with it. I did this a few times with a guy I used to know, and his miserable lack of stimulation coupled with my grinding, gushing arousal had him borderline weeping with the sheer submissive joy of it. What were we talking about again? Oh yes, gagging. It works for that too. And I suspect is also a bit more humiliating for your sub (if they are into that sort of thing) purely because they’re not even giving you pleasure, just doing it because you’re making them.

– cake. No one has ever done this to me, despite all the hints I have dropped about how much I fucking love cake. But I was told by a friend that she once had a guy shove cake into her mouth while he was fucking her from behind, and she gagged on the sticky chocolate overload while twitching with cringing humiliation at how much food was smeared over her face. I repeat: I have never done this, and I would urge extreme caution (choking hazard etc), but I would very much like someone to do this to me. Not with lemon drizzle cake, though: we have to keep some things sacred.

– water. “I’m off for a shower,” I told him, to which he replied “I’ll come with you.” What followed was a truly delicious hour or so in which he used almost everything in the bathroom to humiliate, abuse, and generally defile me. He pushed me into the bath and pissed on me, making me look into his eyes and thank him while he did. He pushed a shower head up against my cunt until I was squirming with a desperate need to come, and then – the bit you’ve probably been waiting for – he filled the sink, bent me over, pushed my face under the water while he fucked me. I tapped out regularly, and he’d let me up to breathe, before pushing me back down again until I was dripping wet, defeated, and gasping. Then he let me come. 

Sexiest place in London?

There are a couple of alleys I’ve fucked in, and there’s a strip club I used to go to that has a seedy and delightful air of desperate men. Either of these places would probably be near to the top of my list, but I can’t tell you where they are in case I want to frequent them again. There’s also a pub which I associate with threesomes, a pub which I associate with the first time I fucked my current boy, and a pub which I associate with the illicit thrill of shagging a guy I shouldn’t have.

Given enough time, I could create a Google Map of all the places in London that turn me on, but they’re all hot because of the association rather than the place itself. So instead I’ll give you the top three places I’d love to fuck in:

• In the ‘oh so many satellites’ room at the Science Museum. It’s just my favourite bit of the Science Museum. Failing that, under the massive dinosaur in the entrance to the Natural History museum.
• Behind the Big Ben clock – I took a tour around it once, and you have to wear earplugs when the bell tolls because it’s so loud. I liked the idea of ‘hiding’ just behind the clock face, and fucking to try and come just before the bell starts to toll.
• Somewhere on the banks of one of the many London canals. Ideally near The Palm Tree pub, so we can have a pint afterwards.

Unsexiest place in London?

Shoreditch. And that’s not just because it’s fun to slag off Shoreditch, it’s because it is one of the few places I go where people who think they are cooler, more awesome, and more beautiful than I am will pass judgement upon me.

Sexiest/unsexiest place in England/ Britain in general?

Sexiest: Bristol. Again because of the personal associations I have with it. Bristol was the place I was introduced to BDSM, strap-on sex, getting fucked with the neck of a wine bottle, watching a hot guy get called “pup” before being heartily beaten by a dominant who let me take pictures, and much more besides. It’s the place I had my first (and best) guy/guy/girl threesome – every single moment of which is burned into my mind and labelled ‘best day ever’.

Unsexiest? Probably anywhere I have never been, because it would never have any of those associations. Confession: despite a desperate urge to go to the Edinburgh Festival, I have never been to Scotland. To ensure it doesn’t get relegated to ‘unsexiest place’ I should go there soon, and have sex on one of its many beautiful hills.

How do you deal with jealousy in an open relationship? Especially if one partner is getting more than the other?

Christ on horseback, I have no idea how to answer this. I know some people can, and do, deal very well with these kinds of issues, and manage to have successful open relationships. I’m not one of them, though. I’ve been in open, or open-ish, relationships in the past and have been torn between wanting to cry with happiness and wanting to tear the world apart. Usually in an open relationship I get more than he does, probably because I seek it with more determination, and maybe partly because I have a fair few male friends who I’ve slept with before who I can easily call on if I’m horny and fancy something a bit different.

So here’s how it usually goes down:

– Oh my God I can shag whoever I like! Awesome! *texts loads of guys and arranges dates*

– Current partner gets a bit sad: “Why aren’t you spending more time with me?”

– I panic, spend more time with current partner. Get stressed because life is too busy.

– I encourage partner to go and date or shag someone else.

– He dates or shags someone else.

– I LOSE MY FUCKING SHIT, cry, tremble, worry that I will die alone, beat myself up with guilt about my emotional hypocrisy.

– He says “OK, I won’t shag anyone else.”

– I stop shagging other people, because I feel bad about the discrepancy.

– I stare wistfully at men on trains, wondering what their dicks look like.

So in answer to your question: “how do you deal with jealousy in open relationships?” the answer is: I don’t. I don’t deal with it at all, and that is why I have never had a successful open relationship. But fuck it, I have had some spectacularly fun relationships, even if they are punctuated by whirlpools of fucked-up angsty panic. Perhaps someone who does deal well with this would like to contribute an answer in the comments?

What are your thoughts on cuckoldry, cuckqueaning and chastity (male and female)?

See above answer for my thoughts on cuckqueaning: a guy I love fucking other people is not a turn-on for me at all, although I can see how it would be for some people. A guy I love fucking other guys while I watch? Hell yes. A guy I love fucking other guys then telling me hot stories about it later? Probably. But anything other than that and I’m liable to cry and stamp my feet like a spoilt child yelling “but it’s MINE and I don’t want to SHARE it!”

Cuckoldry is… OK, yes, this is super-hot. A guy getting turned on by me fucking other dudes? Yes. And, in fact, I know a gentleman who did have a bit of a thing for this. In fact, he introduced me to the idea that it could be super-hot, by describing in detail an angry, shoulder-shaking crywank that he had shortly after he found out I was sleeping with someone new. The idea of him being simultaneously heartbroken and painfully aroused gave me slick knickers and a mental image I couldn’t shake for a week. Subsequently he did fun things such as drive me to other guys’ houses so they could spank me, while he waited outside in the car, throbbing and hard with pain and desperate to hear all about my filthy escapades.

Chastity, again, is hot when it’s done to guys. Mainly because I love how hard a dick can get when it’s not used for a while, and the aching, beautiful agony of submissive guys begging to come. When you tease a guy to the point of climax, then hold off, then do it again, and again, and then make him wait until tomorrow… his dick leaks. It leaks a delicious ambrosia of fucklust. Mmm.

Any more sex blog questions?

I’ve got a bit of time tomorrow, so if you have anything else just drop it in the comments below. I realise this blog is a bit self-indulgent and meta, but I get lots of questions via email and I don’t always have time to answer them all, so doing it this way means I am now publicly accountable and therefore compelled to answer things. It’ll give me a kick up the arse, and means if there are any topics you want me to cover on the blog in future, you can plant the sexy seeds of thought into my mind now, and it might prompt me to remember a hot story, like the bathroom-sink fucking, or the nappy wank video.