Tag : virginity

ok so i’m terrified of trying penetration. i’m sure i’ll like it when i do try, but i’m scared it will hurt. i’m also too scared to use tampons for the same reason. any tips ????

Get informed, get horny, get relaxed, give it a go.

Get informed by making sure you understand how your body works, reading up on your hymen on here and elsewhere for example  http://edging.space/tagged/hymen.

Then get yourself really horny by edging a lot, thinking about fucking watching porn of it, aching to have something inside you.

Then get really comfortable, a warm bath or cosy in bed. Somewhere you have privacy and time to do this.

And then begin to explore, just with fingers first, nails cut so they don’t scratch. Spread your legs wide, edge at the same time, so rub your clit with one hand and finger yourself with the other. Just get curious, and feel sexy as you do it. It’s your body, get to know it.

Slip a finger in, keep edging hard and while fingering might hurt a little, that will be negated by the pleasure so it’s a great combination.

If you can get any a bit of lube, or KY jelly or even unperfumed lotion on your fingers will again make it feel even better.

Once you can comfortably fuck with one finger work up to a couple of them.

Fingering like this rarely feels THAT good because for most women the real pleasure point inside you is your g-spot and that’s a bit too deep in to reach by yourself with your own fingers. Which is why you want to work up to using a slim dildo or a DIY equivalent http://edging.space/tagged/diy-sex-toys

You’ll know you’ve got to your g-spot because it’ll feel odd at first, and you might feel a little urge to pee but do NOT back off, keep at that and soon it will start to feel amazing, it’s kinda like your clit but inside and can be treated more roughly (it’s designed for a cock to be pounded back and forth over it…).

But that’s for later, for now, take it slowly, have fun, get really horny before you do anything, don’t worry about it hurting too much, when you’re on the edge, it all feels good.

Let us know how you get on!


I’m having sex for the first time new week because I’m ready emotionally and physically but want some advice on how I should go about trying to fit my boyfriend’s díck in my pussy when I can’t even get 2 fingers in their myself even after trying for so many years. HOW DO I GO ABOUT THIS?

Okay, I’m very glad you asked about this!

So look, not to get too personal but a lot depends on how big his cock is. The average cock size is about 6 inches. And if he’s around average size then as long as you take things slowly, get really excited first, and USE LUBE it’s going to be fine.

Lube makes your cherry pop so much sweeter

No really, just your wetness, or god forbid, spit, is NOT ENOUGH. Especially when you’re doing it for the first few times but honestly, lube always makes sex better (and is always essential for anal sex, ALWAYS).

Your pussy is designed for cock, if you’re relaxed, lubed and horny it’s going to be good. 

But let’s step away from the denial blog here, and get reading my tips on how to make the first time AWESOME

Follow those tips, and you can’t go far wrong. If your hymen is still intact there might be a little sharp moment of pain where that’s streched more, and even a little blood, from both that and just your vagina isn’t used to being fucked, yet… but that’s completely normal and your pussy, like your mouth, heals super fast and is literally designed for this, so go slow, have fun, and you’ll do great.

Unless, he has a monster cock. If he’s really well endowed then we just need to add a bit more to think about. Basically, it’s going to hurt. Hopefully not a lot, and hopefully, if you’ve done all the above, in that ‘good kinda hurt’ way. Some women actually totally love that feeling of being stretched, but you’re new to it so the big thing is to use EXTRA lube and go EXTRA slow. I mean, crazy good self control by him needed here not to just wham it in, In fact the best tip is just as I’d suggest with anal for anyone, you go on top for that first time. Lower yourself onto him as slowly as you want, and take it little by little, stretching and edging yourself as you go. If it hurts too much then just go for getting the head in and then give him a blow job for being so patient and try again another day.

If he is big btw, make sure to read my guide on blow jobs for big cocks

Two notes, if it continues to hurt, go see a doctor! It shouldn’t and doctors literally train to help you with this stuff. So be brave and don’t suffer, get it sorted.

Secondly, all this assumes you’re both being smart with both birth control (don’t be in this situation, ever) and safe sex. If you’re not, then you might be emotionally ready but you ain’t physically ready, so get it sorted first and make sure it’s a hot, fun and sexy first time.

Oh and tell us all about how it goes cos’ we’re all pervs here and we love hearing about it.

Oh and I’d be remiss if I didn’t add edging into the mix. Edging for a few days up to it would never be a bad thing, it’ll help you be at peak arousal when it’s all happening, which you’ll both enjoy.


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Is it really shitty that I’ve not lost my virginity yet? Im 18 and i feel like the biggest loser and like im never gonna find anyone that thinks im anything special.

No you muppet. It’s not shitty at all, it’s great! 

You’re holding out to do it with someone who cares about you. NEVER feel bad about this. It means you have standards and self-control, what are you whining about?

Most people who lose their virginity younger than you (and you’re only just at the average age for the US anyway) tend, in my experience, to have had a pretty crap time of it. A few are lucky enough to have a great time, but mostly it’s a few awkward thrusts, a moan and a ‘was that it?


You see the biggest problem having sex as a teenage girl, is that you tend to have to do it with teenage guys… (from my own research with friends I’d tend to say lesbians have a better time of it (you might actually get to cum!), and gay guys the worst in terms of first time experiences, but it’s rarely good for anyone).

Teenage guys are really, really bad at sex. They’ve grown up educated by porn, and think that all you need to see is a bare chest and a hard dick to be ready to fuck. They have no idea how to make you cum, or even the concept that you should be cumming long before they even get their penis near your vagina.

You’re lucky if you get this much foreplay…

Now the best thing to redeem that is the two of you are in love, because then it has all the lovely romantic first time shit going on and it turns that few awkward thrusts and a moan into, well loving, awkward thrusts and a moan, which is a bit better.

Meanwhile  studies show that having a good first time experience leads to a better sex life later on in life (no shit) as you aren’t having to undo the negative associations in your head each time you get intimate.

Look, I’m really old fashioned when it comes to this stuff, despite all the fantasies on the blog, I’m a big believer that any sex, especially full on intercourse, is best enjoyed in a committed, loving relationship.

Good sex, making love, is so much more than just fucking (whether that’s cocks in you or a girl’s fingers/strap on or even just cumming together, pick whatever definition is appropriate).

Now please don’t think I’m being a downer on sex outside of that context. I totally get the thrill of it, and the pleasure it can bring. I’m just saying I think the best and most fulfilling sex is found with someone you love.

So do not short change yourself just because you feel some nonsense social pressure to lose your cherry, it’s madness. Plus most of the others are lying about it.

My very first experiences denying someone else was with my wife-to-be, when we kind of accidentally stumbled onto teasing and denying each other. We decided it’d be hot to wait till our wedding night to have full intercourse, so we had 18 amazing months driving each other crazy, in the best possible ways.

She went from cute little vanilla English rose to full-blown kinky slut, and I got mad skills in the finger and oral departments. But even more, I got good at getting in her head and turning her on with my words and actions more than just fucking could ever do (and you my dear followers now read the benefit of that…)

It taught us amazing self-control, but beyond that we spent months discovering all the other ways we could give each other pleasure beyond just sticking my dick in her pussy. And it left room for a lot of romance which seems to be so often lacking in early relationships now. 

Protip guys, a poem beats a dick pic, every, single, time.

So dear anon, you are anything but a loser, so stop indulging the self-pity. Instead, work on loving yourself some more, accomplishing things you’re proud of, and using edging and denial to do as much as you can to turn yourself into a superstar lover in waiting.

That special someone is out there, be patient, use your time positively, and get out and find ways to meet new people. Virgin or not, love yourself, and you’ll find that special someone is very attracted to that. Then you can be the little fuck monkey you dream about and it’ll be all the better for it.


Always happy to have questions like this, and hear in the notes other people’s opinions!

Let me add the usual warning that safe sex is non-negotiable – contraception and a condom is best. Also, your situation is going to vary. If you had a great first experience, I’m so delighted (tell us about it, it’s always fascinating), if you had a bad one, don’t worry about it, it’s just not that important, it’s mostly some silly social construct perpetuated by the patriarchy anyway, right (feel free to tell us about it too). If you had a horrible first experience(s), and many do, and carry the scars of being forced for example, then again, that does not define you, and you do not have to let it stop you from having great sex in the future. However, it’s going to be harder path for you, and one you’ll need someone to help you with in my experience. So consider googling for a helpine or talk to someone you trust, because your past does not have to define your future. Love, James

Would you be interested in training a virgin by using orgasm denial?

It’s always a special privilege and delight to help someone explore denial when they’re a virgin. I just can’t think of a better, more fun or sexier way for someone to learn more about their sexual responses, and what their amazing mind and body are capable of. And to do it before you’ve even had sex, well it’s the perfect preparation for getting super sex positive and much more self confident when it comes to sex and your self image.

I was totally into denial before I had sex, and got my wife to be into it before we got married. So yes, it’s wonderful.

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I lost my virginity today, we had 2 rounds and he thought I came twice, but I didn’t

I’m not sure if you’re saying this is a good thing or not…

Congratulations either way. You just had the same experience as most women unintentionally do. 

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Hi James ! I’m ashamed of being a virgin. I cannot deny myself with vaginal stimulation. I want to try a dildo but I am afraid it hurts too much. Can you give me an advice, please? Can you show me a dildo I could start with? they all seem sooo big ! Thank you so much.

Woah there. Let’s deal with that first one shall we sweetie.

No one should be ashamed of being a virgin. Being a virgin is great, and beautiful. All it means is you haven’t found the right person that you love enough to give your body to in that most intimate of ways. 

There is huge pressure now to lose your virginity way too early, and it almost always leads to hugely disappointing experiences that most people regret and have to work to forget. 

I waited a long time to find the right person, and have no regrets about it whatsoever. I’m still married to her! And that’s despite getting into kinky shit from a very early age.

It sounds to me like you are doing what is important, which is exploring your body and your sexuality so that when you do meet that right person, it’s going to be, literally, fucking awesome. That’s something to be proud of, not ashamed of.

As for penetration, make sure you’re reading up on the hymen, it can hurt a bit but it shouldn’t be awful. If it really really hurts, go to the doctor and say it hurts when you try a tampon and they’ll check it’s nothing else.

Assuming it’s more ouchey than serious pain, then rere’s a picture of your first dildo:

FINGERS, first one, then a couple like this. Cut your nails short. Use some lube. KY Jelly will do, but some water based lubes like these will do even better.

RUB YOUR CLIT AT THE SAME TIME – get horny first, be really horny as you keep doing it. Pain turns to pleasure for most people once you get horny enough, and you’ll relax too. For it to feel really nice you need a bit more than a finger length, so this is just good practise for exploring and getting ready for a dildo.

As for the dildo to get, I recommend one on my toys advice page, which looks like this.

I still haven’t found better, everyone I play with ends up getting one. It sticks amazingly well so you can use it with no hands, it’s incredibly smooth and lovely to touch, and it’s the perfect width to start off with, as well as use as you get more into it.

Anything thinner gets a bit ‘pokey’, so even if it seems a bit wide, it’s not, get it, trust me. And if you get it from Lovehoney you get a year to return it anyway, so give it a go – just get lube at the same time as suggested.

Read more on it here:


Once you get it, again, go slow, use some lube (it doesn’t matter how wet you are, lube makes it better), get really horny and slowly start playing with the tip. tease yourself, over your pussy, just the tip, little strokes. Then a little deeper, make yourself want it before you let yourself have it, slowly deeper, rubbing your clit harder and harder. 

And when you slide it all the way in, and yes, you can… you can cum.

Good girl.

Let us know how you get on

What’s life like for Denial Academy girls whose masters have requested that their virginity be preserved? I’d imagine that they’d have to do tons of anal training, but what about the girls who were designated anal virgins as well??

Well on the whole while virginity can be preserved, penetration is required as part of the classes at the denial academy, as you can read about here:


and here


Virginity, of course, is not related to whether you have penetrated your vagina or your hymen is intact, but is purely related to whether you’ve had penetrative sex with another person (lesbian definitions vary but that does it for me).

Occasionally we get students who have been put on no touch for extended periods, or had their labia closed with piercings, or perhaps even infibulated to enforce anal only status. They will not be spared anal penetration, in fact their anuses are treated just as pussies, and all masturbation and training is simply done to that hole.

The other girls are pretty mean about it though, at least that’s what we hear. They tell them all the time how good it feels to fuck their pussies and make them watch when they do their homework edges before laughing at them just doing it to their ass in return. It’s not easy for an anal only girl, but it does build character.

There’s an anal only club that they can go and seek solace in, and share their unique frustration with the other girls who are anal only, by choice or otherwise. They share such things as anal edging tips, nipple masturbation and the practicalities of having a never ending craving to be filled.

Dear Sir I was wondering if you know of the best way to take your own virginity. I read about hairbrushes and wanted to try to do it but I’m nervous. Do you know of any way to minimize the pain other than tons of lube? Thank you

Well, technically you can’t take your own virginity. Virginity isn’t a medical definition, it’s a concept. For most it means, have you had sex with someone else, simple as that.

So, you could literally sit on a flagpole, break your hymen and orgasm. But you’d still be a virgin.

Now what you may mean is what’s the best way to deal with your hymen, which is the very thin membrane most women have at the entrance of their vagina as they grow up. The hymen doesn’t break, it stretches and kind of gets worn away over time.


Also you may just be curious to explore how it feels to have things in your pussy.

In which case the simple answer is to start with your fingers. Get aroused playing with your clit, and play with one finger in your pussy then see if you can manage two. If you learn that feels nice then yes, a clean hairbrush handle is a good thing to try next. There’s nothing to be nervous about, just go slowly, enjoy rubbing your clit and let your fingers or the brush penetrate you slowly.

You might get a little bit of blood at first because your hymen is being stretched a little, but that should barely hurt and it’ll only be a few drops at most.

So try it out, going slow and being aroused is much more important than lube. 


I know this is likely not the way you meant it, but your definition of no longer being a virgin only once you have a penis in your vagina doesn’t really allow for the loss of virginity in same sex couples. I personally think you’re no longer a virgin once you’ve had a mutually consensual and satisfying sexual experience with someone else. But I think that virginity is something that you have to define for yourself since there’s so much debate about what does or doesn’t qualify as losing it

Did… did you actually read the rest of the post before you sent me this? The bit where I explicitly stated I wasn’t sure what counted for lesbian couples? And then where I posted to other resources that define it pretty much exactly as you did, ‘whatever you decide it means for you’? I like your definition though.

But you’re right, I should have included ‘in your ass’ for gay guys, as that definitely counts. 

The whole debate about ‘does anal lose your virginity’ for hetro couples though is a totally fascinating debate. I start to think about it then get too amused at the thought of good girls taking it in the ass to preserve their ‘chastity’ to be able to come to a conclusion. (If this is you, please, write and tell me about it).

I do love feedback but at least read the rest of the post before you send me stuff… The question was specifically about penetration, and the worry that virginity could be lost by fingering or using toys. The point was, it can’t, it’s conceptual, not physical, and has to be a sexual act with someone else.

So just to be clear, there is nothing you can do to yourself when masturbating that would cause you to lose your virginity. So edge away my little virgin denial sluts, your innocence is safe with me…

When I finger myself im gonna be unvirgin or?

No, virginity isn’t a physical thing, it’s a concept – you technically only lose it when a penis enters your vagina. Nothing else does it, Not a finger, not a hairbrush handle, not a tampon, not panties, not a dildo, not even if you stuck a hand in there (although what’s lesbian etiquette, does a strap on count, someone tell me).

The physical part of virginity is related to the hymen, a thin membrane that most but not all women have a little way into their vagina, but this is more of a frill than a covering, a common misconception. If you don’t know about the hymen you NEED TO WATCH THIS VIDEO. 

Read this too and feel free to come back with any more questions – I love sex ed!


Send me your sex-ed queries, no such thing as a stupid question.