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.
80 Comments
I love this post!
I’ve been asked a few times, the subject has been broached – but I’ve never done it.
The idea has alwasy turned me on but I think it really has to be a super willing partner and someone who’s into it.
It wouldn’t turn me on if they didn’t want it.
And I’m glad to hear it doesn’t always work out…. I’m less scared now. I think if I was rubbish at it I’d be devastated!
Thanks GOTN – once again some absolute aspirations for me x
If only I had met someone like you before I got married! Never approached the subject with my wife, too worried about it being a huge turn off for her…..
Hey I’m half Italian it’s my heritage I never tried it but if you really into it and really enjoy it and totally get into the experience and no strings attached if you really want to do this but please don’t judge me for wanting to try my heritage at least one time I promise I’ll let you have it and I’ll let you shove your bare feet in my mouth eat your ass I really really good pretty much time deeply I can In-N-Out
U can do it to me x
I’m blaming you when the current girly gets begged to peg me when I see her next. That first story is so hot… might have made a mess just thinking about it.
Yum and thanks!
A great range of experiences, each of which I can relate to (although, for obvious reasons, not all of them were the first time!). As noted elsewhere, it’s still a major taboo for a lot of straight men (certainly in terms of the way we discuss sex with each other – I don’t have any idea how that translates to actual bedroom activities, and I suspect that many of the straight men either reading this site or who people reading this site have been with will be a self-selecting open-minded group) and I think that enthusiasm from a partner goes a long way to removing that taboo. It certainly did with me. I always enjoyed solo anal play but it was only after a while that I discussed it with my other half, and seeing her eyes light up when I said that I wanted her to fuck me made me want it even more, because it became about more than just my pleasure.
We’ve had times where it’s felt uncomfortable, as in your second story, but more often than not it’s either the first or, most frequently, the third.
I’m very impressed with anyone who has nailed the technique with a strapon, by the way! It’s difficult enough for us when we first start having sex to get techniques right, and our cock is attached to the front of our hips and has nerve endings!
Just a quick question.. my hubs just asked me to do this. We went and bought everything we needed for it. But now I’m scared. Is this really things straight men think of? Wheno he first asked me my responds was,”I will try it as long as I know you won’t leave me for a guy later..” he honestly wasn’t shocked I said that. Then I made him feel bad. The thought of this turns me on. It just scares me.
He wants to get fucked in the ass, by YOU. :) Sex between a man and a woman, no matter what kind of sex it is, is by its very definition ~heterosexual~ sex. I’m a man that loves anal sex, giving and receiving, and I have absolutely no attraction whatsoever to guys. My beautiful wife though, wearing some sexy lingerie and her big strapon girl-cock bobbing up and down in front of her is a sight that drives me wild. We don’t peg very often, maybe once every month or two, but it’s always a HOT experience we both get off on.
Know the experience….my hubby also is into CD…..totally sexual for him and I….
I think I can speak for your man in this situation, I to would love my other half to strap on a big cock and fuck my ass. It’s not a gay thing for me and I don’t believe it to be for him. I have always been uninhibited sexually and I absolutely love my girl to tongue lick and finger me but she is reticent about the toys in my ass for exactly the same reason as you, I’ve never even entertained the idea of having another guy in me, it just doesn’t do anything for me. But the thought of a woman fucking me and enjoying it as much or more than me, now that is a major turn on
Relax……engage in foreplay…video or two and let nAture do the rest
I’m male. I like aggressive, strong, dominating women. The psychology of the woman in such a ‘power’ position is appealing but the idea of anal sex, not appealing.
It doesn’t appeal to me to give it to a woman and less than just unappealing receiving it. Unnatural in an unnatural way, not sexy, erotic fetishy; more latent gay inclination. When it has been talked about almost every time it turns out the guy (generally ex husband or bf) has ‘discovered’ eventually that he’s homosexual.
I imagine that’s why pegging has zero appeal to me as a guy.
Listen up, dude: you don’t have to do this stuff if you don’t want to. I’m certainly not going to make you. It doesn’t make you gay, though, any more than me getting my cunt eaten makes me a lesbian. Sexual acts are only a tiny part of what makes up someone’s sexuality, and frankly it’s tragic that you believe there’s some kind of gay button up the bum which, if pressed, will switch your sexuality. Your assertion that ‘when it has been talked about almost every time it turns out the guy… has ‘discovered’ he’s homosexual’ is complete bollocks. I have known many many dudes who have enjoyed anal play and I cannot think of a single one for whom me putting fingers/a butt plug/a dildo up their arse has caused material change to their sexuality – most were straight, a couple have been bi or bi-curious, none has turned round and gone ‘well that was so life-changing I have reevaluated the whole core of my sexuality.’ It’s just a bit of butt sex, chill out.
I’m quite sick of guys popping up on posts about pegging to go ‘but it’s gay though!’ because
a) that’s just not true.
b) there’s an undertone in your message that there’s something inherently wrong with being gay, which there isn’t.
c) you very clearly do not understand the topic, having a self-confessed disgust towards the whole thing. You don’t need to have tried pegging in order to discuss it, but if you want to be taken seriously in any discussion, at the very least you need to not approach it from a platform of proud ignorance.
d) you’re generalising wildly about men, based on your own personal experience, which also erodes any credibility you’re trying to lay claim to. It would be like me saying ‘well, no woman would ever dream of fucking L Ismor, because he is profoundly ignorant and also probably a homophobe.’ Maybe *I* wouldn’t sleep with you because of this, but I assume someone has, in order for you to get a feel for the kind of sex acts you do and don’t like.
And while we’re at it, please drop the ‘unnatural’ – humans have been bumming for millennia, certainly far longer than we’ve been sending messages via the INTERNET. If it’s ‘natural’ you’re concerned with, you probably shouldn’t be here.
Mmmmmm! Hot!
This is excellent, thanks! Lately, I’ve been wondering what it would be like to take on the more dominant role, although it’s rather intimidating. One of those things on my sex to-do list.
Do it to me
Happy to lend my back side ;P first time for everything.
I’d love it… it’s my number 1 fantasy to be fucked vigorously by a beautiful woman.
I just recently took my husband’s virginity. Seems only fair since he took mine way back when.
I still don’t have the hang of it down – can’t get used to not actually feeling anything and I think my husband forgets that too on occasion. Like he was stroking the strapped on cock and expecting me to feel something. I had to remind him that he actually needs to touch ME.
Any pointers to make things go more smoothly would be greatly appreciated. Oh, and do you know of any strap-ons that aren’t so complicated to get on that they completely kill the mood?
Heya – good question! I think the key with strapons is to make sure that when you put them away they’re done in an easy way so that when you bring them out again they’re not all tangled + stuff. I prefer ones with a solid harness with straps that go around and under the arse as well as just round the waist (you can get some that go round the waist and through the crotch, but I find these trickier). Halfway down this page is one with a harness like mine: http://www.girlonthenet.com/sex-toys/
I think in terms of making things go smoothly, the main thing is practise (I know that’s a really boring answer!). Also I find that it can be better often to get it partly in/just the tip then tell him to push back/down into it. That way he can ease it in at the right angle. The hardest thing for me is not being able to feel it, so I don’t always know that it’s going in right. Ooh, also I *love* strapon sex with him on top. i.e. a guy sitting on my dick. Makes me feel powerful and badass. If you haven’t tried it, I thoroughly recommend it – guy-on-top pegging gets five stars from me.
We love the Endless Swan. Just saying.
Wow hot story!
I have found the joy of pegging with my partner. She loves using the strapless one, with an internal dildo for her pleasure. Coupled with a Wee vibe, this gives us both the most intense orgasm when She wants me to ride her.
I don’t care to tell you the last part of your story here has me rock hard waiting for my first time when she force me to sit down on her and i have to look her in the eyes as she hers me moan controlling me,forcing me to take her. My ex wife snuck her dildo into me 1 day,i couldnt back up,she held me down,pinned me ,told me thats it baby you can do it,she had me moaning,wimpering at her mercy,im afraid what someone skilled with a strapon will do to me. Now excuse me,i think i have something causing a problem now…
My girl wants to have anal sex with me she went out to buy a strap on so she pulled it out and i got so horny but it is my first time and i loved it. Is that a bad thing
No, if you loved it it’s definitely a good thing. Have fun!
First time was with a friend’s girlfriend. While he watched. She made me take 9 inches hard. He grabbed my head and shoved his cock down my throat. Until he came down my throat. It was a fun night.
Try double ended strapless strap on dildo. Whit vibrations.
I’m 40.. In triple digits w/lovely ladies.. Not cocky.. Point to that statement is, I have NEVET experienced anything like w/my past. I felt uncomfortable @ first, only a few times, now, WOW.. If most were/are honest w/them selves, TRY! Your not homosexual, believe me..! To talk if w/my wife is a turn on all together.. She loves it, so do I! It’s a MIND BLOWING EXPERIENCE!! No bullshit, saved my relationship. It’s trust, comfort & love.
Try the double sided strap on. Pleasurable for both. My wife loves it and so do i
Fantastic article! Makes me want to try pegging.. I think I’d be addicted, especially being tied up and told what to do!
I am a horny individual and have recently got my g/f to finger me, but wud love her to wear a strap-on and give me a right good pegging making me squirt all over her gorgeous breasts, dunno if she wud do it though :(
What an excellent post. As a longtime pegging aficionado, one interesting thing about the activity is that – although the first time is certainly memorable, at least mine very much was – the experience, like all good sexual experiences, keeps on growing. Having for years had this as an occasional enjoyable subset of my sexual experience, I’ve recently fallen into the hands of a determined dominant partner whose mission is to totally destroy my ass, and she’s very capable of it too. Unlike a male partner, her advantage is that she’s able to trade up to bigger sizes once she determines I’m ready for it. So my next few months are going to be a voyage of discovery. A very, very stimulating one.
The first couple times were experimental for us both. On about our third or fourth different toy (large and intimidating) with a more sturdy harness things went %150 beyond what I could ever have imagined! She put me on my stomache and spread my legs with her own as if I was trapped without restraints. I was feeling very vulnerable and could feel my heart beating out oft chest, especially as I peaked back at the massive purple toy that was my lovers new cock. “Do you want any lube” she said as I fumbled around with my left hand at the night stand still cemented into place on my chest. I handed the lube back to her as she then greased up the instrument sliding it between my cheeks as if she were fucking a pair of breasts. “You need to relax” she said aggressively, as I knew that was an possible command! I gripped the sheets and bit the pillow as she slowly pressed beyond my resistance. “Ah! Gentle” I said. Though I was yelling it was as if my words went unheard as she railed deeper and faster into me. As I was moaning and my muscles still fighting I decided it was already happening I muse we’ll embrace it. I let loose of any resistance I has a relaxed and floated on clouds that were our sheets. After laying there submitting to my aggressive thrusting I relieved my self screaming out “oh god! I’m done, you can stop. Oh god!” She again continued until I lie there speechless, shaking, and fully draind. Every muscle in my body was now jello and unable to move. After she released the new burden from my back side she laid on her back and unfastened one side of her strap grabbing me by my hair sunk my face deep within her. She has said that was the most intense cunninglus I had ever performed, and by god she deserved it! Strap up ladies, and show us men a hell of a ride.
I love it… especially with a double dildo strapon so the girl has a chance to work on a orgasm for herself….that’s the hottest thing i ever experienced, a girl having a orgasm whilst fucking me
Wow!!! This was a GREAT read! I have yet to actually try anything more than fingering my ass. I get a bit scared because so many people say it hurts really bad. Honestly I do want to try some anal play beyond a little fingering but don’t know where to start.
When I was 19 a girl stuck her finger in and massaged my prostate and it was an awesome orgasm. Since then I’ve known I wanted to explore that aspect more. While I was married my wife would lick the area between my anus and balls occasionally while giving me a blow job, that felt nice also, she even gave me a rim job once or twice. Once she approached me from behind, reached around and stroked my dick while simultaneously thrusting her pubic bone against my ass, that was awesome. So one night I suggested we take it a step further and her penetrate me, she wasn’t very receptive to the idea but a few years later she finally did with one of her small dildos. She wasn’t in to it and was obviously doing only because she knew I was interested, I got off but it was not a mind blowing experience and that was the end of that. After 23 years of marriage we divorced. Fast forward three years to a new relationship. My new girlfriend absolutely loves performing oral sex on me including rim jobs, then she took it a step further one night to prostate stimulation via her finger then two fingers. After the prostate stimulation that led to future conversations about anal sex and she eventually revealed that she had actually used a strap on on a previous boyfriend. That was the opening I was looking for and we had several discussions about giving it a try. We went to several adult toy stores and websites, we eventually found what we were looking for on a website. The anticipation mounted as we waited for the order to arrive. Once it got there we went on a date, nice dinner and a couple of drinks then returned home anxious to give it a try. I’m not sure who was more excited. The fact that she had done this before did give me a sense of reassurance that it would go good. The set we ordered came with two dildos, different sizes. I was chest down ass up as she prepared me with a generous amount of lube and some finger play. Now it was time and she started with the smaller one first, it felt good but kind of anti-climactic since the small one was a small diameter and only 4.5 inches long. The larger one came next, oh my my what a feeling, my butt was full but not too much, my prostate was being stimulated but most of all I was allowing someone, a girl to screw me in the ass, and I was liking it, (The great thing about it were all the conversations we had had before the act, about this not being a gay act but an act of exploration of my sexuality and my trust in her to share this experience with me.) , I was able to openly express my satisfaction while she screwing me even to the extent of moaning and saying things like speed up, slow down, harder, deeper; and when I finally came it was the best orgasm ever and I mean ever. She and are still together and 1.5 years post my opening we’re enjoying it even more as an addition to our sexual repertoire. As we’ve honed this experience we’ve tried all kinds of different positions, purchased newer and bigger toys and butt plugs that we sometimes use as a precursor to an event, even as far as wearing one of the smaller plugs out on a date, she has, I have and on one date we both did, and we have a small vibrator that she has worn out on a date, that was fun watching her writhe as I played with the control. To this day I have no desire nor have I ever been attracted to a mans ass or any other sexual act with a man, this is strictly between me and my girl and I have never felt more open or liberated than now. Doing this someone I trust has made even more rewarding.
In retrospect I wish I had been able to experience this much earlier in life. To all the guys out there who have the slightest desire or curiosity about this, find someone you can trust and try it, don’t waste the bulk of your life wondering, if it is for you then you have a lot of years ahead of you that you can have fun with it, if it is not for you then you can add that to the “I’ve tried it, didn’t like it, move on the next experience” category.
Just want to say thanks for sharing your story.
Well said..!
penus
Only gay or bi men would accept to be penetrated by a plastic penis aka dildo, ayy lmao.
You seem to be under the mistaken impression that straight guys don’t have prostates. I can assure you that countless millions do.
They can totally be counted. They’d be about 3500 millions.
You seem to be under the mistaken impression that you understand men’s relationship with their own bodies.
Well, men all have different relationships with their bodies. Some will enjoy the pleasure that having a prostate can bring to anal play, others won’t, others would rather not try it, some don’t have prostates at all. Generally I learn about men’s bodies by… talking to them about what they like, listening to what they say, and experimenting within their comfort zone. It’s honestly not rocket science.
If you say so mate. I’m as straight as an arrow but it’s something I would openly try no problems. Nothing wrong with exploring your own body
This guys a douche bag thats not comfortable at all with his sexuality. I let my girl finger my ass lick it and fuck me with her dildo and it makes her pussy so wet it runs down her legs. She loves doing and it feels amazing i fuck her in the ass everytime we have sex. With that said not one time have i ever thought about a guy doing that to me or will i ever im the farthest thing from gay so with that said Thats the least i can do for her. After 2 and a half years we have the most amazing sex life we fuck every single day sometimes 2 or 3 times a day. I bet you dont have that or never will. So you might wanna take a look at yourself before you talk shit about other people and what we do
This has been great to read (except Str8 man but we’ll ignore that). We’ve just bought our 1st strap on although my wife has used them b4. Used it once but the jelly dildo it came with was just too big 1st time. I could tell she was itching to really show me how fast and hard you can go so think I just became too tense. Bought some smaller items to try instead and spent time alone with plugs, beaded wands and a suction cup dildo so hopefully I am less tense and more used to bigger objects. I wanna say that sterotypefreed made some insightful comments and whilst a newbie I already feel I wished I had done this years ago.
I’m 40.. In triple digits w/lovely ladies.. Not cocky.. Point to that statement is, I have NEVET experienced anything like w/my past. I felt uncomfortable @ first, only a few times, now, WOW.. If most were/are honest w/them selves, TRY! Your not homosexual, believe me..! To talk if w/my wife is a turn on all together.. She loves it, so do I! It’s a MIND BLOWING EXPERIENCE!! No bullshit, saved my relationship. It’s trust, comfort & love.
I agree w/you.. Ignorant statement. I’ll bet this person is alpha male like my self but, not comfortable with.., personal.. W/your wife, girlfriend, don’t think of male in that way, it’s an orgasm.. I don’t care what’s said, F•••••• AMAZING..!
I gave my husband his first adult bare bottom spanking on his 30th birthday. I really gave it to him so hard he had handprints all over his ass. I didn’t stop at 30 he got at least almost 100 whacks. In the late 70s there was no access to dildos so I used my fingers on him and also taught him how to eat my ass. When we split up I knew he was anal aware and if I would’ve had access to a dildo I would’ve certainly fucked his ass. I was disappointed when I met him in the late 80s finding out he was playing with dominant women who had already taken his anal virginity with strapons. He actually bragged that he had his own harness and dildo at his house so the first time over his place my X was face over the bed getting fucked by me. Truthfully I preferred whipping his ass rather fucking it. When he begged me to take him back he was going to have to pay for lost time so I took it out of his ass whipping him as hard as I could. I taught him how to suck cock with a strapon and now he can Deep Throat a 9 inch dildo without choking. It’s actually turn on to watch him sucking my cock rather than fucking his ass. We have a suction dildo that we use in the shower so I can impale him on and torture his body in other ways. I pinch his entire body with close pins while he is busy fucking himself on the dildo. I’d rather just stand there and smoke cigarettes while he fucks himself making him do all the work.
Would love to have a session with butch she can whip my arse always
Girl on the net. Never mind the links at the bottom to buy a strap on! Come and take me like you talked about with the 3rd story. Really got me going reading that. Thank you for sharing :) :)
Butch, you’re the definition of a perfect dominant woman.
My girl’s had her cock on her mind for ages and ages while she was married to some feckless gorm for 18 years. She brought it up not long after we’d began seeing each other. Me, I don’t care how we fuck as long as there’s strong emotion and desire so she bought an expensive very life-like 8 inch cock and strap and first time, I straddled her, reverse cowgirl so she could see the ass she was fucking. It was great, really hot and beautiful cuz I love the hell out of her and she just gagged for it, soaked her strap and came all down her legs, soaking my balls too. It was one most erotic experiences of my life, pure pleasure and connection.
She got me flipped over and really let me have it, totally free now to express herself, no judgement, no coyness, no asking. It was the best thing exactly cuz she didn’t ask, just took what she wanted. Finally, a woman who wasn’t passive. What a fucking relief. I’ve had to train so many women to step outside their little girl conditioning and just do what they really want. So sometimes I want to be the girl? So fucking what? I don’t need to be all girly, just like to have my girl give me her maleness as I give her my femaleness and back again. What’s so hard to figure about that?
Just as much as fucking me, she loves to see me suck her cock. I feel her convulse and cum when I have her cock down my throat. I smell the thick salt of her cum. The trick is to put the cock in her for a while first, get it all wet with her cunt and then it’s so hot to suck on and swallow.
My girl loves expressing her maleness and admitted for years she felt like a freak for wanting to fuck guys in the ass, see them suck her cock. But she doesn’t want to be male. She’s enjoys being a very hot, very smart, very switched on female. Has had a couple kids and still has the tightest little pussy.
And I love fucking her tight ass, enjoy the same sights as her as she squirms down my hard-on disappearing up her beautiful ass, our rhythm joined and easy. We’ve been together now some years and we’re both pretty highly sexed so it’s a good match. We fuck a lot, in a lot of different ways. It’s about our fun. She puts a leash on me that locks my balls up into my abdomen and kinda strangles my cock then wraps it round the back and pulls my ass cheeks apart. It’s like a bridle. So when we’re wandering in the parks and laneways at night, she can push me up against a wall or fence, pull my pants down just enough to grab hold of my leash and fuck the ass off me, just pound me. Since my balls are jammed up high in my abdomen and my urethra so choked off, I can’t cum. She gets to decide when I cum and giving that up is huge freedom for me. When she wants me to cum, she’ll unhook my leash, my balls drop into my empty scrotum and I fire very hard, my ass slamming back onto her as she whispers filth into my neck, still hanging onto my leash bridle.
Same way I sometimes grab her by the hair for kicks, shove her down and face fuck her hard, make her puke on my cock. She swoons, says it hits the nerve in the back of her throat and makes her piss cum as she squats beneath me and sucks on my balls as i jerk off and cum all over her. The trick is we don’t need anyone else. She’d spent too many years married to some asshole who called her frigid when she was actually burning up with fire. I’d wasted decades on stupid middle class cunts who couldn’t suck the foam off a beer cuz they lacked that lust for life that’s not only about sex but is about everything, how you see the world.
So we’re lucky to have met, which was a total fluke. I was in Malaysia for work and had met her for 2 minutes at a dull affair at a beach bar, somebody’s birthday. We spoke for a few moments and she told me to meet her next day at a coffee shop.
When I got there next day, no small talk, no nervous bullshit, no nicey nice. She stood up, kinda flushed, and just laid a hot kiss on me and said, “You gotta place we can go?” She got on the back of my bike and we took off for my pad and that was a few years ago now. She dumped the gorm husband, the fucking moron. He’s still wondering what he did wrong. Stupid hetero guys are so useless.
So now we do our thing every which way, including some very hot pegging because we both live by the notion that there’s more to fucking than just fucking…
wow! Sensational shares…………..
That was hot, pegging is awesome
for those who to try there’s some great sites like: strapondates.com & peggingdates.com ;-)
U can dress me up as a schoolgirl or maid then put me across your knee spanked to tears then put me ass up to peg my virgin ass
I loved every comment made on your page. I have anticipated my first experience of getting pegged for quite some time, I was married to a woman for 42 years. She passed away in 2012.
I have been trying to locate someone with whom I can hook up with, to experience some of the Sexual experiences which I have day dreamed about over the years. I think that every man should have a Pegging Experience. I think that it would open their eyes to many of the Sexual joys which they have been missing all their lives. I have worked my Dildo’s quite vigerously, but they lack in reality to a real life experience.
Hi William – thanks! Really glad you’re enjoying it, and I hope you do manage to fulfil some of your pegging fantasies. Just a quick thing, though – I’ve edited your comment as the original contained your full address. Please don’t post details like this on my blog. I appreciate that there may be reasons you want people to get in touch with you, but I can’t take responsibility for personal details posted publicly here, as I can never know if that’s your real address, and I also can’t guarantee that you wouldn’t get any nefarious people using it for devious ends. If you’re interested in meeting people who are up for sharing your fantasies, there are lots of dating and kink sites that I’d recommend you check out!
I absolutely love to get pegged by a hot chick. I often wonder why men are sometimes flaccid when they are getting pegged. It never happens to me, but in the limited porn I have seen on the subject it looks like they are having a hard time maintain a stiff erection. Thank goodness I don’t have that problem. I blast my cum against the wall when I am getting pegged. I love it.
I can’t remember how many followers you have but at least some of them will be experienced medics. I think what the rest of us would love to know is whether there is any long term risk involved. Could anyone enlighten us?
No more than with anal sex, although of course the pegger often has to be more careful/gentle/slow because they don’t have the immediate sensation/feedback that someone with a flesh cock would have, so there’s slightly more risk of you slipping out and shagging the wrong place, or going in too quickly. But with lots of lube, a sensible pace, and a comfortably-sized cock, you should be OK. Here’s the NHS website on anal sex risks: http://www.nhs.uk/chq/Pages/3050.aspx?CategoryID=118
Thanks very much for the link.
The NHS link doesn’t mention any physical risk. Hemorrhoids? Damage to Prostrate? The STD risks are a given.
OK, well if you’re not happy with the info I’ve given you maybe you could Google your own? As far as I’m aware though, anal sex doesn’t give you haemmorhoids or damage your prostate if you do it slowly and easily. If it did, I suspect it would be mentioned on that page.
I love a great size strap on in my ass gets me so wet and your cock and your own personal working of your hips just fucking feel great deep in my ass getting so hot and bothered I might get the wife to fuck me to night and I will ride it deep in my ass fucked by my own wife is the way to take control of this ass of mine
How can j make this happen with my wife
My wife and I have been married for 3 years now and we’re hitting a bumpy patch in the road . The sense of not feeling comfortable 100% is starting to enter like I’m loosing trust or something and she’s pretty prude I will say she only likes to have sex until she gets her nut then I have to hurry up and get mine and she hates it in the butt as well ( only done it one or twice ) but me I love a dildo in my ass absolutely love it makes me moan and groan like no other buisness and I really really fantasize about being pegged by my woman . Seeing her sexy ass naked with a strap on on is so hot to me but I kno she wouldn’t do it cause I’ve hinted to her about a year ago that I wanted fucked with a dildo and she replied with ew no that’s nasty and she thinks it’ll turn me gay but she probably didn’t think I was being serious but I was 100% serious . Does anyone have any advice on how to approach there woman and talk about this subject ? And am i the only one scared to death to bring it up to her ( even thought were in a dry spell from sex ) I read some of these stories and it’s everything I want ! Some help me !!!!
I’ve done it 4 times the first time was with some friends. Lost a bet and I let his wife do me. He keep telling her harder. Came real hard. The second time was at a party took a 12″ from 7 women. Everyone was cheering them on. 4 guys shoved there cocks down my throat. Swallowed every drop. 3rd time was a friend she really went hard on me. She told me she whished she had a bigger one. So did I. The fourth time was at a bar. Started with a birthday spanking. Ended up getting fucked by every girl that worked there. Nothing under 14 inches. Plus every guy throat fucked me. Came down my throat. Or on my face had cum in my eyes. Couldn’t wipe my eyes. Next time I want to see if I can go bigger and more people.
Won’t lie I’m a virgin to a STRAPON, it the thought of a woman dominating me,hearing me moan and beg and just totally under her control turns me on a lot.
I’m divorced though,hard to know what sites are legit to meet someone in your area,and which ones are just a credit card and such scam.
I’m really scared, but interested in meeting someone to try it with who would be patient,kind,and gentle to start,and recomendations,much appreciated,thank you.
There’s some info and advice in this piece here: https://www.girlonthenet.com/2013/12/04/on-making-your-sexualfantasy-come-true/ Best thing to do is get on dating sites or look up professionals in your area who specialise in strapon play!
Sorry so long to reply back. Where I am here is a very small town,,not really anything at all in this area, I will try the link you sent me,but if not,just keep my email, who knows maybe 1 day you’ll find somebody heading toward my small town…lol way it’s going I’ll prob die also virgin lmao thanks again
My wife and I first began pegging about 3 years ago at my urging. At first it was awkward and clumsy, but now it is simply awesome. Initially, my wife just played along but now she gets a mischievous smile on her face and asks me if there is something I want. We don’t do it all the time, maybe once or twice a month, about the same frequency as anal for her. We have a nice toy collection, vibrators, dildos, strapon harnesses, etc. My advice is to start slow, use plenty of lube, relax physically and mentally (dont be so uptight) have fun, and always make sure that the lady is taken care of, before, during or after. If it isn’t your collective thing, then try something else. Finally, try/do it enough so that you and your partner can move beyond the awkward/clumsy stage.
Unfortunately I’m the number 2 guy.
It’s just really uncomfortable and hurts too much for me to enjoy, even with enough lube.
I have nothing against it though, if people wanna do it and enjoy it more power to them.
Just read article and posts. My wife and I are in our 50s. We have been married over 25 years. We are very sexual. We recently tried it and absolutely love it. Pegging has made us closer. It is extremely intimate. She was upset that I could take it all so we went out and bought a thick ten incher. She loves opening me up and so do I. Being vulnerable, needy, trusting is all new to me and it is wonderful. I had never done any butt stuff before other than to her. She took my anal virginity with enthusiasm. Recently she took the dildos away from me so I can’t use them by myself…so I would be tight for her when she wants it…that is sexy. The other night she walked into the living room with the harness on and ten inches hanging down and says to me “get your ass in the bedroom I want some butt”. That is sexy. Also new is being used as a sex object. Everyone should try it. About the gay thing – that is silly. A sex act does not indicate you are gay, straight or bisexual; it is who you do the act with. My wife is really a natural with penetrating and I soooo happy she is.
I LOVE this message, thank you so much for joining in. Delighted that you and your wife are having fun exploring this! <3
Every night I lay nude in my bed dreaming about a girl that straponfucks me I wanna be her bitch my ass her pussy to fuck
I really want to get pegged! My perineum and anal area is very sensitive and aches for attention when I get aroused; especially when my wife plays with my nipples! Once she agreed to it but now is adamant to not do it. Oh how I wish…..
Just re-read this one, and the rather enjoyable comments, after it was linked again recently.
I’m afraid I was guy number 2… but it was still pretty awesome, even if it wasn’t actually pleasurable. And I’m sure it would only become better with more practice.
Like the third case was my first time.