We Did It! – My First Time Getting Pegged

Image from Take it like a Man

So we finally did it. And it was awesome. Here’s the story to my first time getting pegged.

Friday night we stayed in. We had some dinner, had some drinks, had some sex. It was good. Then it was Saturday. We woke up, went for a bit of a walk and when we got back home we started getting into the motions that lead to sex, ie. getting naked. Well, usually it’s me getting her naked and we go from there.

So I was taking her clothes off amid touching and kissing and hugging. And the next thing I can remember from there is I am pouring silicone lubricant over her pussy and rubbing it in with my cock. Now that’s a little weird because normally we use water based lube but Friday night we had a bit of shower sex and used some silicone lube that we have had sitting around for a while and because of how awesome it was on Friday night, when I reached for the lube, I grabbed the silicone.

Now, though we usually use water based lube, I’d say about half the time we indulge in anal play, we use silicone lube. So pouring the lube over her pussy and seeing it drip down to her anus, I got cute and putting my cock by her asshole, then her pussy, asked her “In here, or in here?”

When I put it next to her anus, she said “You can try.” Wohoo! Anal time. So I grabbed a mini double ended dildo we have, one that I think is designed for anal play because each end is shaped a like a butt plug is that it goes from slim to wide to slim again. You put it in and it stays in until you pull it out.

I eased the slimmer end into my wife’s ass and pushed my cock into her pussy. After a little while, I took the dildo out, turned it around and slowly slid the fatter end into her and again left it there while we fucked for a few more minutes.

I stopped, took it out then went back into her pussy one last time. However, when I asked if she wanted to go ahead with anal, she said she didn’t feel like it. Fair enough. Some days it works, some days you think you’re ok but it doesn’t feel as good as you’d like it to. I know this from my own experience and the warm up had let her know today wasn’t a day for anal for her. Well, turns out that meant it was the day for me.

After asking her if she wanted me to fuck her ass and her saying no, I just asked her if she wanted to fuck my ass. The unhappy face that was telling me I couldn’t put my cock in her ass lit up in a smile and she said “Yes.”

She wanted to fuck my ass.

So I took a few seconds to remember where the strap on was, it being so long since I had put it away, unused. Well, today we were going to use it. (Here’s my review of that strap-on – the Red Rider.)

I got it out and put it on the bed. Then I grabbed my wife and threw her onto her back and slid inside her pussy for a little bit more fucking. It just feels so good and I wanted to be really ready to go before we proceeded with her pegging me.

That done, I grabbed the harness and dildo again and gave it to her. She stood up on the bed and got into it. I stood up with her and kissed her. She said to me “Why are you standing up?” and made to push me down onto the bed. So I got down onto my knees, face at her belly. She still wasn’t happy with that and the thrill of dominance coming over her, she gently pushed me again down onto my hands and knees.

I handed her the lube I had previously been pouring over her pussy and she started lubing me up. Feeling that it wasn’t enough, I told her she need more, that she needed to try pushing the lube into my ass rather that just trying to push her finger all the way in, in one go. She got the hang of it and was massaging the lube up my asshole.

I felt like I was ready enough and told her that was enough, let’s just do it. And we started. Her behind me, pegging me doggy style.

Her aim was a bit off so again I had to guide her. I have to admit, being the passive (or submissive, or receptive) partner, it’s not so easy to give instructions, but for everyone out there who gets fucked, I feel like I should say that it is very fucking important. Make sure it is working for you too.

Anyway, she got it in but again I had to ask for more lube. Once that was sorted it was ok. At this point, I am really getting pegged. My wife has a dildo strapped to her crotch and is fucking me (carefully) in the ass. And I can’t see anything that’s happening. A completely new experience in sex with a partner. At every other time, because of where my cock is, I can look down and see what is happening. Now I am all about feeling. And trusting. I can’t even see my wife, I’m just looking at the headboard.

And the feeling in my ass is kind of familiar but strange and new in that I am not controlling the movement. It’s ok, actually I can’t really remember how it was but probably somewhere between ok and pretty good. Anyway, we stopped and switched to missionary position.

And damn that was a good idea! Now I could see my wife, I could touch her breasts and could see her thrusting and best of all, the curve of the dildo started working how it was supposed to work. It was rubbing across my prostate. Then she grabbed my cock and started stroking it. I was goo-goo. My ability to talk was suddenly like that of a one-year old. All I could express was pleasure and pain and right then it was all pleasure. Overwhelming new pleasures of the anal kind I hadn’t been able to experience alone.

Then, encouraged by my groan-moaning, my wife starts really getting into it, fucking my ass and stroking my cock and urging me to cum. And I would have loved to. In fact, it kind of felt like I was cumming the whole time. But I didn’t. Instead, we stopped and I unstrapped the strap on from her and finished with me fucking her. In her pussy. And it was awesome. The whole experience was out of this world. The second time I got pegged was pretty good too!

23 thoughts on “We Did It! – My First Time Getting Pegged”

  1. My fiance wanted to years ago i wasnt to happy but i let her finger my ass while she blew me and then bam, i cam uncontrollably and she loves it and now here we are using dildos on myself

  2. We did it this weekend for the first time.. It was amazing, better than expected. As I lay on my belly feeing helpless, she was pumping away. My body was uncontrollable, kind of like going into convulsions. Why in the word did I wait this long to ask!!!!!!!

  3. Did it for the first time last night oh my goodness was awesome. I had tried it myself but could not get erect but last night when we did it together I got rock hard. She started off telling me to roll over and placed the 8 inch dildo up against my ass. I guided it into my ass a little.
    She was shy saying what do I do? “Just slide it in slowly.” I told her. After a few moments I was moaning, could not hold it in. She being encouraged by my sounds started to get unto it by pushing deeper, fast then slow. I was dripping big time and was starting to push against her thrusts.
    Then she slowed up and slowly withdrew it fully then would slide it back in all the way. This happened a few times and I could hear her laughing till I could hear myself begging her to push it back in 2 or 3 times and I finally exploded. As I lay there thinking how incredible it had been she hopped out of bed washed the dildo and started to fuck her pussy with it saying how good it felt to have 8 inches in her. As I lay there watching her fuck it for maybe ten minutes she took it out and told me to lick her pussy.
    She moaned as I went down on her as I licked her I grapped the dildo and pushed it up to her ass. Just a little is all it took for her to cum. The feeling of the dildo and my mouth was too much. What a night! It was more than I hoped for as a first pegging session.

    1. That’s really hot. I love that she came back and started fucking herself with the dildo then asked you to go down on her and finally it was the dildo going up her ass that got her off! Mutual anal! I’ve never tried that – it’s only been one of us at a time so far.
      Tom, thanks for sharing the story.

  4. Woman here, I always love it when an guy talks about cunnilingus and pegging. I love pegging, I love it when an guy lets me use his ass-but I feel like so many men are selfish and have no desire to make the girls feel good with pegging or cunnilingus. Or maybe its just me because my mix breed friend is able to get the guys to do whatever she wants. Even this blog is all about the Op’s pleasure. Right now I’m trying to search for blogs targeted for females and their pleasure for pegging but I’m literally not finding ANY. It’s very disappointing but it kind of makes me want to create one with videos, pictures, discussion and more. =D

    1. Hi Lynn! Thanks for your comment.

      I think for sure that sex, no matter what you are doing, should be something you can both enjoy. And oral sex is a wonderful way to enjoy sex.

      Whether women enjoying pegging is something I’ve wondered about and discussed before, but that was more to do with whether they liked the act itself. I’m sure, women could enjoy pegging a lot if it involves receiving more oral sex!

      One thing I don’t like about the way pegging is (not always but) often portrayed is that the woman’s pleasure comes from the domination or even humiliation of the man. I like your take where the pleasure comes simply from something that is physically pleasurable, like cunnilingus.

      If you do get that blog started, I’d love to check it out!

  5. Yeah it’s not about domination at all well not for me; it’s about finding it pleasurable. We had our 2nd session after our first session I didn’t want to press my wife for it again I knew it would happen when the time was right.
    One night I wanted to have sex but she said she was tired (which she was). It was no big deal I was just going to masturbate as I have done many times as she lay beside me. But this time she said do you want me to use the dildo on you as you masturbate. I replied that it was a huge turn on last time but if you’re tired it’s no big deal, she smiled and said I’m not too tired to hold a dildo.
    I got out of bed and got it from the dresser and climbed back in beside her. She took the lube and squirted it on her fingers, turned me around on the bed and applied it to my ass with her fingers, and then cuddled up behind me in a spoon fashion and with one hand gently spread my ass and placed the dildo into the right spot. This time I didn’t need to guide it in but she didn’t go straight in either. She moved it up and down between my ass cheeks and then gently pushed it up against my entrance but took a little longer to enter the tip.
    She was silent and didn’t say a word for a minute or two then with a gentle push I felt it enter me again I couldn’t help it and I let out a soft moan.
    All I heard her say then was “Are you hard?”
    I replied “Yes.” then she said “Touch it for me.” at which point I slid my hand down onto my cock
    She was pushing in the dildo at a nice slow pace and would withdraw almost fully then slide it back in again.
    Once again I found myself pushing back to meet her thrusting she was silent as she made those movements but I was moaning as it went in and I worked my hard cock.
    It seems over the years she has learned to understand how I react to things as I didn’t have to ask her to speed up as I became more excited but her thrusting of the dildo into my ass became faster I heard myself say “Yes, yes, that’s it.”
    The feelings were immense. She was still silent not saying a word but her thrusting had become hard and forceful. I asked for faster then harder. I was rocking back towards her then for the first time I felt her large breasts crushed up against my back. I don’t know why I hadn’t noticed it before or why I was only noticing it now but the thought of it was too much for me. I pushed hard back onto the dildo and I felt the warm cum drip onto my hand. She knew I’d cum but continued to push it in and out.
    The she spoke and whispered into my ear “You like this, don’t you?”
    I didn’t answer. I was a bit spent after cumming. I was expecting her to stop thrusting but she was still doing it. I said “I’ve cum.” She said “I know.” but continued.
    I moaned some more. I had gone soft but was still enjoying it. She said “Can you give me another cum?” as she slid it in and out. I said “No.” but she didn’t stop. In and out, nice and slow.
    I began moaning a little louder. I knew I wasn’t going to get hard again, not so soon, but none the less it was very exciting to have her to continue to do it even after I had cum. She finally stopped after a minute or two and said “I bet next time I get you to cum twice.” She handed me the dildo and said goodnight,

    1. Wow, that’s a really hot outcome to such a normal “Sorry, I’m too tired tonight.”

      I wonder if her instinctual speeding up of the dildo when she was fucking you with it was not only from knowing you but also from knowing what works for her too. I feel like (and this sounds obvious but) being fucked is completely different from fucking which is part of why women prefer to opt out of sex when they are tired, whereas for men, the horniness can often override tiredness. But one great thing about pegging is that it lets us understand that part of the difference between us – that being fucked is different from fucking.

      I’ve written about how peggging can help men understand what a request for anal sex might be like, and I think it’s helped me understand what a request for sex is like when you’re not completely in the mood (as mentioned in this post).

      For example, after you’d cum, she kept fucking your ass even though she knew and you’d said you’d already cum. Women often experience this and it’s something I think we men take for granted, not even questioning what it feels like for her to keep being fucked after orgasm until we cum. Not meaning to negatively criticize or anything, just putting the idea out there to be thought/talked about.

      Anyway, sounds like a nice memory and I hope you don’t object if I borrow that scenario on occasion for mental stimulation, putting myself in your place of course. And I especially like that she has put up the challenge of making you cum twice from getting fucked. If you ever manage it, I hope to hear the story!

  6. Hey, we started the blog. It’s me and three other girls right now. It’s called PeggingForHerPleasure.wordpress.com We hope to have an Youtube channel up as well within the next year. Nonetheless, the blog is for women and their pleasure when it comes to pegging, and/or men who care about the pleasure their women can get upon pegging. Thanks for allowing me to post it on here. =D

  7. Sean, we haven’t got around to another session.
    It’s something that’s been very exciting and I don’t want it to become the normal sexual routine, although she has asked when would I like it again.
    On a side note, I have noticed that she has become slightly more dominant in our normal sexual play.
    You can borrow it if it helps you to enjoy your experiences more, and would be excellent to hear yor feedback on it.

  8. @Tom
    I also prefer pegging to be a special occasion act. Also, for me, it’s something I only want when I’m very horny. And I’d never want my wife to do it if she wasn’t into it – that’s half the fun so it’s infrequent when the planets align, but it’s fun as heck!

    I don’t know if I noticed any increase in dominance from my wife during sex after we first tried pegging but I think it increased the trust and intimacy in the bedroom, so bringing up new ideas in the bedroom after that became much easier.

  9. Me and my boyfriend will be trying pegging for the first time on new year’s. I’ve been fingering his asshole while I blow him for a couple of Months now and he’s finally ready to get fucked . I’m excited but nervous at the same time.

    1. Good luck. I think you’ll both have a great time.

      I recommend starting with some oral for you, then some oral for him, then fuck him. If you’re both horny as heck when it comes time to peg, it’ll be super hot.

      I’m actually kind of envious of him having his first time – my first time was amazing just because it was a first time and every sensation was new and amazing but you can’t do that twice. Not that I don’t still enjoy it and it’s still overwhelming when my wife and I get the strap on out but the first time you try something new, well… there’s something magical about a first experience.

  10. Hi sorry to dig up an old post but thought after reading these comments it might be the best place to ask. Myself and a girl I’m seeing are talking about trying this for the first time.
    Do any of you have any advice for me (male) for my first time being pegged? I could look over the net for days looking but you guys have done it so have more experience in it.
    I’ve never done anything analy other than having a girl put a finger up me while blowing me. Was a shock at the time and we were both quite drunk at the time.
    Hopefully someone sees this comment and replays.
    Cheers John

    1. Personally, I knew I enjoyed anal play/stimulation so from my experience I’d recommend at least getting to know yourself and being sure you’ve got the potential to enjoy what’s coming. So yeah, do some solo anal play then when you’re comfortable there, bring in your partner.
      But I’m pretty sure it’s going to be awesome. Have fun!

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