Pegged for the First Time #1

Kate and Adrian have only just met, but Kate is about to fuck this 'virgin'

Free4All - A new storyline inspired by a Paid Subscriber xxx

Adrian felt the tip against his ass hole. Kate breathed in his ear one simple word, “Ready?”

He mumbled yes, and it was done. His first pegging began in earnest.

Kate and Adrian had known each other for months. Or, if you look at it a different way, they had only met an hour ago. Or if you want to be ‘Biblical’ about it they had only ‘known’ each other from the moment Adrian mumbled ‘yes’ and Kate mad love to him. Fucked him. Pegged him good and hard.

It was months ago they had met online. It was another trawl for both of them on ache and annoyance that is online chat. Who is real? Who is sincere? Who is a bot? And who is out to scam you? Will you find love? Will you find a friend? Will you find sex? Will you even manage to cum?

In Adrian’s case, he wasn’t sure what he wanted to find, but every time he felt a little lonely, a little in need of a thrill, and the chat rooms weren’t giving him much, then he’d type ‘pegging’ into porn hub, and soon he’d feel alive.

He’d not worried that this meant he should really be looking to talk to men online if he wanted fucking in the ass so badly because the curve of a woman, the eyes of a woman, the lips of a woman were all he craved.

Ok, there is probably not a man alive who doesn’t look at a muscular handsome man, or a really fine thick veiny cock and think, “Yeah, I’d like a suck on that one day, once. I wouldn’t mind seeing what a body like that feels like under my hands. I think I couldn’t say no if he wanted to fuck me hard.” But a relationship with a man sounded like a nightmare. How did women manage that?! And most men weren’t those adonis beauties, whilst most women had something about them he loved. Bi-sexual, maybe, but probably he wouldn’t even qualify for that.

But god did he want a woman to fuck him!

Seeing women fixing their temporary cocks to their waists, rubbing them up and down like they were jerking themselves off, ordering men to their knees, on hands and knees, placing the phallic object, often so much bigger than the average cock, between the ass cheeks of that man and…

And grabbing his hips with one hand and then pushing it in, forcing it into a place that may never have had anything pushed into before. Well, the men in those films were probably old hands at it. They had probably been fucked by dozens of women, yes, maybe by men too. And he did watch men gangbanged by women or taking a bi-sexual group sex fucking. Yes, he had mixed it up a bit when it came to his favourite pegging fantasies.

But what he loved most, whatever he was watching, was the women’s faces. They were either smiling with glee or determined and lust-filled. Were they acting? Did women not really enjoy this kind of thing? That might be logical, and when he wasn’t wanking himself off, he would consider this, and think about it properly. ‘What could a woman be getting out of it? It pushes against their clit a bit, but that’s not enough surely? They could have a two-way strap-on that goes inside them, but that wouldn’t be moving very much. Why do they do it? Just to please men?’

There were lots of answers to this, and this was what he would search for on chat, trying to find real women, real women who liked to fuck their men, or any man, to ram a ‘dick’ up inside them.

He struggled to find the answer there and wasn’t happy with what he googled but it seemed to him one of the reasons must be the control it gave them, the power to fuck rather than be fucked. The best sex is perhaps always more equal make love WITH, rather than make love TO. But he had read and enjoyed enough erotica, watched enough porn, had sex with enough women even, to know that a lot of sex was swapping power back and forth.

He had a friend in the kink scene who was what they call a ‘switch’. She could be a meek sub for one man and a tyrant dom to another.

He wondered in some ways if all of us aren’t a little like that, swapping back and forth, even in the same night of love making, even in the same half hour. One on top wrists pinned above the head, then she throws you off and climbs on top, using you like you’re not even there, her head flailing in the air, her eyes elsewhere, her mind elsewhere. Then you take her from behind and cum inside her like she’s been strapped onto a gym horse for your ease of use and probably many other men as well!

He had listened to her talk on a few occasions about it, although he had never admitted his keenness for this one particular thing, although he knew she did that to men. He was embarrassed and scared. He couldn’t take a thing like that up his ass! He had put small vibrators there, tried it out, but anything bigger would never go in. So why did he think about it all the time?

This was why he talked to women online, hoped they would be women, and sometimes wondered if he might meet one. Otherwise, he was going to have to ask his friend. They had known each other since school, and there was no way he could ever admit to anything with her, despite how wild and kinky she was!

This was how he met Kate.

Kate was not a dominatrix. Sometimes she tried to imagine being one and couldn’t quite get her head around it. She tried it online. She tried, but it didn’t really work for her. The men she spoke to loved it, but she wasn’t very good. She wasn’t a wild woman, she was quite meek, but something one of them said made her imagine other things.

Man: Hello Mistress. Are you looking for a sub.

Kate: Well spotted worm

Man: Thank you Mistress

Kate: You best still love me when I am whipping you

Man: I will Mistress. I am wearing panties and bra rn for you

Kate: sissy slut

Man: Yes i am Mistress

Kate: Poor thing. Poor poor thing. But I am afraid I am going to walk all over you. Literally

Man: With your heels on Mistress? It is gonna hurt

Kate: That is the idea you silly little gimp

Man: Oh please dont step on my clit

***

Man: you're gonna dominate me? ;)

Kate: Yes you little worm

Man: Try me. Tell me just how you're gonna make me kneel, cause I'm telling you now I never kneel 😏

Kate: You'll want to kneel for me or my long highheels are goign right up your sorry ass

Man: Big talk until you've got a cock down your pretty little asshole. I know you'll glare at me but deep down you'll know who's the one kneeling

Kate: You won't dare. My whip will see to that

Man: Your whip in my hand as I whip you, showing you your place? Yes your whip will certainly see to that

***

Man: Hello miss

Kate: Hello Mr

Man: How may I please you?

Kate: By licking my toes and working your way up

Man: Can I hump the floor as I'm licking your toes mistress? My cock is really hard

Kate: Leave that silly little worm alone

Man: Fuck... But mistress is throbbing.. It keeps pulsating I'm so desperate in sucking your toe Licking your feet and going up

Kate: My ankles. Don't touch that fucking nasty little penis

Man: Can I go up with the tongue or the feet is the limit I'm not touching. Sorry mistress I'm trying to please you

***

Man: yum

Kate: Knees

Man: so i should get out of doggy

Kate: No. That will do. Now take this heel up your ass

Man: i can take a toy if you want miss

Kate: Oh but I want to make your ass sore first boy

Man: yes mistress

***

A toy. She knew what he meant: a vibrator, a dildo. But wasn’t that only for gay men or lesbians who wanted something different on occasion? Or maybe it could be for women who didn’t have a partner at the time? Or women who did have a partner, but one that wasn’t very good at keeping her satisfied. She had known both of the last two problems, although she was single at that time.

She was single, and she was using a rabbit on herself, and it felt damned good. So nearly everyone used toys then, except for straight men. Unless those straight men were with women who were happy to use toys on them.

She imagined if that last man she spoke to was there. Could she put her highest, pointiest heels on and push them into his ass? Wouldn’t it make him bleed? But if he enjoyed it, what was wrong with doing it?

But really, it sounded like he wanted a dildo pushed up there. Would she do that? Some guys did love their asses played with. She had fingered a few guys and even licked one boyfriend there. He was delicious with joy when she did. Could she shove something bigger up?

She imagined then that she was doing it, that she was pushing a great big dildo up some man’s ass, so deep, without mercy. She imagined him groaning and begging for her to slow down but not stop, begging her to free him of the beautiful agony and also shouting to ignore his screams, ignore when he asked her to stop and for her to keep going, keep thrusting.

But all that was her standing there or lying there, her arm moving, but not much more inclusive than if she’d been giving a handjob.

There must be a better way to do it?

That was when Adrian came online, and their interests aligned.

Four months later, they finally met up in a café they both knew. And less than an hour after that they were in the café’s restrooms, too impatient to go home to do it, and Kate was whispering in Adrian’s ear, “Ready?”