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We Did It Again! – My Second Time Getting Pegged

This is pegging. Pegging is amazing.

This is pegging. Pegging is amazing.

And this time I blew up. She fucked me to orgasm. But let’s start at the beginning because this was a great night of sex, not just me getting pegged.

It started when I walked into the bedroom and there she was getting dressed in some sexy lingerie. I hadn’t seen her wearing lingerie for a while so I knew we were in for a good time.

As we had last time, we had been drinking that night and the easy going feeling was still with us. We’d had quite a few “Let’s do it.” moments then let it go without anything happening for my ass, so this time when she said “I’m going to fuck your ass.” I decided we had to do it this time.

But when she asked me, I had to tell her that I wasn’t ready yet. “Let’s fuck first.”

And it was some good fucking.

Lots of lube. A massager-vibrator in the mix. And orgasms.

Fucking in missionary, she held the massager under us and pressed it against my cock as it slid in and out of her juicy pussy. Somehow, it made my cock somewhat numb and I was so hard and fucking her so hard with no threat of busting.

Moving the massager to her clit, she came. “Can you cum again?”

With the massager back on her clit again and my cock that felt like it was on steroids stroking through her folds, she came again.

The massager-vibrator now on the sideline, I fucked her to one more orgasm. “Oh, fuck. I’m done.”

Orgasms seem to be quite physically exhausting for my wife and sometimes she just seems to keep cumming in one continuous roll but three distinct orgasms is something we’ve never done before. Anyway, as she said, she was done. Time to switch.

We got up, she strapped up and we lay back down.

I lay on my back and she kneeled between my knees. At first, she was having fun being rough and pushing my legs back hard like she was forcibly going to have her way with me. But when it comes down to it, she is very careful not to hurt me.

It took a little while to get the angle right – it’s best when she is standing on her knees rather than sitting so the dildo is angled down at first.

Once we got everything in the right place and in the right way, she was off. Last time, perhaps because she was playing with my cock the whole time, I was hard the whole time. This time, getting the dildo up my ass took a little bit longer and she seemed worried she would hurt me. Anyway, during that time my cock went untouched and was soft and floppy by the time I asked her to start stroking me.

But pretty soon my cock was back and again, with her fucking my ass and stroking my cock it felt really good. Not as overwhelming as the first time but it was still really good.

And this time, I came.

With her stroking my cock and fucking my ass, I came.

Unfortunately, at some point, and I do not remember, I said stop. I’m pretty sure I meant to stop fucking my ass but she stopped everything. After the first shot of cum went rocketing out of me, she stopped stroking. The rest of my orgasm pooled on my belly.

I also remember it felt like I squeezed the dildo out of my ass with the first contraction. And I don’t like it. I already knew that I don’t like cumming with anything up my ass from solo play but she wanted me to cum while she was fucking me last time so this time, when it came so easily, I thought I’d go along for the ride and try it out again. But no, I still don’t like it.

So my ideal pegging session would be me fucking her, her fucking me then ending with me fucking her or her sucking me.

Just Relax

Woman pegging man - just relax

“Just relax” she says

Until you are on the receiving end, you probably have no idea how difficult it can be to “Just relax” when someone want to put something up your bum. Even more so when that something is a cock or a strap on dildo (which is what I’ll talk about here).

It’s also very difficult to willingly put yourself into a position that gives your wife access to your ass. I’m a guy and it was and is difficult for me to take what I’ve known only to be the female position – lying on my back with my legs spread apart and in the air or kneeling in doggy position waiting for my wife to come up behind me with a dildo strapped to her crotch.

Part of what makes it so difficult is how sexy and feminine I find these positions – at least when I see my wife in these positions. So for me to get into these positions is difficult, mentally.

Back to relaxing. When your mental perceptions are being challenged; when you are in a position you are almost uncomfortable being in and your wife is approaching with a rubber dildo strapped to her, ready to fuck your ass, it’s not easy to relax. Despite wanting to let my wife fuck my ass, there is the paradox of not really wanting to “submit”.

Giving up control, relaxing, being the one to be penetrated is hard to do. It requires a confidence in yourself and huge trust in your wife.

If you can, though, the pleasure is amazing. Getting ass fucked by your wife while she jacks you off, your cock and balls covered in lube – the sensations are overwhelming.

No Pegging, but a Bathtub Blowjob is Good Too

We almost did it. I wanted to and so did she but we got ahead of ourselves. That in itself is kind of a sexy tale so I’ll tell it now.


I asked my wife if she wanted to use the strap on with me again. (We’ve had it for a while but sadly, so far she has fucked me with it only once.) After confirming that she was going to be putting it up my ass, she smiled and said that she indeed wanted to use it with me. “I like fucking your ass.”

It was morning when I asked her and we had some things to do that day but come the afternoon, we were free. We showered then got into the bath together. To tell you the truth, she got in the bath and I stood in front of the bath as she took me into her mouth. Quickly I grew, hardening in her mouth. She sucked me this way for a few minutes then, not wanting to be done then and there I pulled away and got into the bath with her.

How the bathtub blowjob startedImages from That is Hardcore and Amadise

After a little cuddling I asked her to sit on the side of the bath and show me her pussy. She did and with the intention of licking her sweet cunt, I tried to manouvered myself into a position that would allow said pussy licking but found it to be quite uncomfortable, almost impossible. (Try lying face down and bending your body to the shape of a bathtub and then craning your neck to the angle of a pussy hanging of the edge of the bath. It doesn’t work.)

After a few licks, it was obvious it wasn’t working for either of us so she got back into the bath. Then she had me stand up and starting sucking me again. With her fingers massaging the area under my balls and her following my instructions, (I like to tell her to slow down, go deep, lick it, suck it, suck my balls, etc.) I was definitely getting close. I had her focus on my balls for a while to avoid cumming but we had passed that point where this was just a quick “pre-fuck-suck”. This had turned into a blowjob proper.

The thing that I am recalling right now is the view of her face half hidden by my sack as she licked right under my balls and because of the arch in her back her ass was sticking right out and it looked phenomenal (quite like the picture above, which isn’t us, obviously). By now, I’d taken over jacking my cock so she was sucking on my thumb while still massaging my balls and suddenly I’m saying “You want my cum?” And she did.

After such a fantastic blowjob, I shot a little harder than expected and the first shot missed or sort of ricocheted off her lip and landed on her shoulder and breast. The rest filled her mouth. I pushed my cock back into her cum filled mouth and she slowly and very softly sucked me as I shuddered through the final death shocks of my orgasm.


And that’s why I didn’t get pegged. I think the idea of the pegging got us both a bit too worked up. We even fucked again that night after I made her cum on my tongue but pegging just didn’t come up and to be honest, after the blowjob I didn’t feel like getting fucked. For me, anal play is something I like when I’m very, very horny. Like “haven’t cum in days” horny. When I’ve just had fantastic head, pegging is out.

Pegging in the Movies

Perhaps one of the first instances of pegging in the mainstream cinema, here is a scene depicting a man getting pegged. It involves what seems to be a psycho nurse, a man who seems to be fresh out of jail and a lot of metaphoric imagery.

It’s pretty easy to see why this is movie from the 1970’s was rated one of the worst movies of all times. Have a laugh.

Does Getting Pegged Make You Feel Gay?

Pegging ArtImage from MIAOU

I’ve already written about my concerns about getting pegged which touched on my concerns about the physicalities of the act and also about how it would make me look to my wife. I also briefly mentioned that I was worried about taking the submissive role. And, it isn’t easy to admit but I was also a little worried that getting fucked in the ass might make me feel gay.

I was just about to say “In hindsight” but that feels too pun-ny. So let’s just say that after the fact, I can easily say that my worries on that point were silly. But first let me take you back in time.

When I was an adolescent and discovering my body, quite a while after I discovered the joy of the thing sticking up in the air right in front of me, I discovered the strange pleasure that could be found behind me. I think at first, I just innocently enjoyed the pleasure but after a while, I started wondering if I was gay. I don’t think it seriously bothered me, I was seeing a girl at the time and very much enjoyed our trysts but there was a small part of me that wondered if, because I enjoyed putting things up my bum, was I gay.

Like I said, I don’t think all this bothered me too much but it wasn’t till a few years later that I realised, how could I ever wonder if I was gay when I never wondered about guys. All I was doing was enjoying my own body.

But then, before I let my wife fuck my ass with a strap on dildo, I did have a little fear that maybe getting pegged would make me question my sexuality. Would letting my wife do me in the butt make me want to search out men to do me in the butt too?

Turns out, no. And again, I should have realised that my desire to explore this area of sex play was a desire to explore it with my wife and not with a guy.

I’ve had this post in my head for a few weeks now and have finally gotten it down. I hope this post helps anyone reading to realise that any fear you have of doing this and that it might make you “gay” is unfounded. I recommend trying this with your wife too because if you like anal play by yourself, letting her do you is a lot of fun, more pleasure than I’ve ever experienced by myself and (at least in my wife’s case) she found it a lot of fun being the “fucker”.

*Apologies if this post makes it sound like it being gay is something to be ashamed of or something bad. It isn’t. But for a straight man to question his own sexuality, it is a difficult thing. It makes me realise why “coming out” must be difficult when it really shouldn’t be.

Inside My Wife’s Behind

I just (last night) fucked my wife in the ass. I suppose I am supposed to be writing about her fucking me in the ass but it goes both ways. Last night it turned out to be her turn. Not that we take “turns”, that’s just the way it happened.

I like having anal sex with my wife. I’ve heard some men aren’t really into the idea of putting their cock in their wife’s behind but for me, it’s a pleasure. Physically and mentally, I love the taboo of it all. Licking her ass is something I also like to do whenever I’m down there. Why? Because it’s a little taboo. My wife makes it even more delicious by going a little quite when I do this. She doesn’t ask me to stop, and if ever there is something she doesn’t like she tells me, but she goes quiet like it’s naughty. Like she is surprised I would lick there.

My wife also fucks me in the ass with a strap on. I say “fucks” but in truth we have only done it once. So far. We both look forward to doing it again sometime soon. But you have to wait for the right time for things like this.

Anyway, last night my cock slid up my wife’s asshole and it all happened so quickly. Well, quickly for us, compared to how long we normally take about working up to anal sex. And I don’t mean just the warming up of her asshole; I also mean getting into the mood for it, etc. It takes a while. But last night it just sort of happened and I think her fucking my ass had something to do with it.

When she was pegging me, she was initially amazed at how tight I was when she was warming me up. Then when she was pushing the dildo (the one strapped to her crotch) up my ass, she was amazed at how far she could push it in and how quickly I could take it. I think this sort of convinced her that she could do it too and if that is what happened, last night she proved she could.

We were sitting at the table, talking about something that led to sex and then I said I wanted to cum in her ass. Then I slid the stuff that tends to accumulate on one’s table to the side and said, “Right here.” Well, without a word, she got up and bent over the table right then and there. I was a little surprised, unsure if she just wanted to play around or if she was really offering me her ass. Maybe she didn’t really know either. Well, I pushed her dress up, pushed her panties down and after unzipping, pushed my cock against her asshole.

Just resting there, I leaned forward to rest my chest against her back and kissed the side of her neck. Still nothing. I stood up and put a little saliva on my cock head and rubbed it against her anus. Still nothing. More saliva, more rubbing, still nothing. More saliva and I can’t remember if I slipped a finger in her ass at this point but it eventually got to where I was pushing against her, about to enter and finally I asked if she wanted my cock in her ass. “Yes.”

Slowly I went and she took most of me in her ass. Half way through I asked her to turn over. She did and I fucked her ass while she held her legs up. I asked if she was ok, did she want to stop. Normally, ass fucking for us (where I’m fucking her) doesn’t last very long (something like the picture only it’s not such a sad face) and it’s either just the end of a sex session or part of a sex session. Never before have we had anal sex unto itself. I asked her if she wanted to stop. She didn’t. She wanted me to cum in her ass. Ok!

I kept fucking her, the inside of her rectum soft against my cock head. It felt fucking good. We use condoms for vaginal sex to prevent conception but because we are monogamous and have both had blood tests, I feel we are both safe not using condoms for anal sex. However, I always wash with soap and water afterwards and try to pee as soon as possible. Back to the fucking… it felt really good. Also, it had been a couple days for me so I was ready to cum without too much hard work on her end. And I did. Cream-pie-ing her ass was awesome. And I’m wondering if all this was because I let her take her strap on dildo cock to my ass. If it was, well that’s like two birds with one stone, right there.

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.

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 awesome and I have a lot more to share but I’ll leave it for another post.


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