Like a friendly wedding DJ, I’m always happy to take requests. The most recent one came from a gentleman who emailed me to ask about thongs. Specifically he asked if I could write about them in-depth, presumably so that he could read the entry with one hand down his own pants and an eager smile on his face.

Problem is, I’m personally not that bothered about thongs. I discovered them when I was younger and – initially – I was a huge fan. I had exactly the kind of arse that looks brilliant in them, and to be honest a decent thong frames someone’s bum in a beautiful minimalist way – slim fabric tracing the line of their crack and curving round the top of each buttock like a ribbon decorating a present. Lovely.

Thongs as sex wear

Unfortunately, my ‘oh God thongs are so hot’ phase clashed horribly with my ‘wearing corduroy trousers that were always a size too big for me’ phase. This led to some deeply hot moments – a mate picking me up, throwing me over his shoulder and carrying me across a bowling alley while the then Love Of My Life looked on and bit his lip with poorly-disguised lust.

When we got home the first thing he did was shove both hands down the back of my trousers and gulp “I’ve been wanting to do that ever since. I just want to fucking bite you.”

But these hot moments were greatly outnumbered by the not-so-hot ones. Catty whispers from people nearby when they noticed the slim fabric line peeking out of the top of my trousers. Guys who thought they were breaking new comedy ground by slipping their fingers beneath the fabric and twanging it like giggling schoolchildren.

The guy who emailed me to ask about thongs made very specific mention of the fact that he thinks they’re especially hot on ‘corporate’ girls. By which I can only imagine he means ‘women who work in offices and generally dress in suits.’ Apparently the tantalising glimpse of thong fabric is especially good when it appears above smart trousers, ideally in a meeting of some sort.

Sadly I can’t really see the appeal in this. I struggle in an office environment anyway – the clothes are uncomfortable, and always coupled with a dread that I’m not quite professional enough – not polished enough. The idea of colleagues also spotting the line of my knickers poking out the top of my smart skirt sends shivers down my spine. I’ll put this down to the aforementioned childish knicker-twangers: selfish twats who’ve ruined thongs for me forever. Not to mention that a bit of the credit should go to men who leer openly at women they work with, as if their boners are as normal an addition to an office environment as photocopy paper or unnecessary spreadsheets.

The sexiest knickers

Still, the absence of thongs does not mean that I never put on a new pair of knickers and say ‘oh God that’s great’. Although I don’t have quite all the gorgeous knickers I want – I’d love a pair of caged-back ribbon knickers, in case anyone’s planning Christmas gifts this early and wants a massive hint. But I have got a fair few pairs that make me feel awesome as soon as I pull them up to my waist. Here are my top three.

French lace knickers

These give excellent bum coverage, while still being shaped nicely enough that they make my arse look excellent. Bought from Primark for about a quid, they’ve been jizzed on, shoved into my mouth, pushed to the side for easy-access quick-entry hard sex, why – they even featured in one of these blogposts a couple of years ago – I’ve definitely had my money’s worth.

Boy shorts

I don’t understand why underwear must be so gendered – I love wearing boxers designed for guys just as much as many guys I know love the silky feel of a pair of well-made knickers. But still – ‘boy shorts’ that are designed for girls do give an excellent level of comfort, and they also cover just enough that I can wear them around the house with just a t-shirt – tantalising the boy with occasional glimpses of the bottom of my arse cheeks without terrifying the neighbours into buying new blinds.

Burlesque ruffle pants

These are pants designed to make your bum look bigger, and they are so stunning that I often put them on just when I want to have a wank – bent over in front of a mirror so I can imagine someone coming all over the back of them. I have occasionally been known to change into them before a guy comes round, so that when I let him in I can just lie on the bed and wait for his inevitable ‘mmmm…’

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. 

One of the most difficult fears to overcome is the fear of being weird. That’s partly why I write this stuff – I want people to read it and say “Oh, she does that as well. Perhaps I’m not abnormal after all.” But far greater than that is my need for people to tell me that it’s OK. That I’m not odd. That they do this sometimes too. And by ‘this’ I mean ‘wanking on the train.’

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