Honest first pegging stories

Sex Tips & Talk
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So yesterday me and my long-term boyfriend tried pegging for the first time! Below I’m going to talk about a lot, but for those who want to read a brutally honest first-time experience feel free. My bf and I are hoping this’ll help couples who are contemplating trying it

For the week leading up to the ‘big event’ we did a lot of talking about different things, especially how we were going to communicate during (we have a traffic light system – green = go, red = stop everything right now) and what we were going to be doing physically.

We decided on missionary because we felt it’ll be a bit more sensual, and it’ll help with keeping communication going. It was really key that the communication was there because a person can feel very vulnerable, and it was my priority that he felt comfortable. We decided to take ‘baby-steps’, which progressed from being in the position and me thrusting fully clothed, to the point where we were both naked and he had a plug in.

I had never given anal pleasure before, so a lot of this was breaking down my barriers as well as helping my partner live out a fantasy. Part of this was introducing finger play. He was very concerned about what I could encounter back there so he kept checking if he were clean (he had douched for me before each time); at that point I knew all I could do was assure he was okay. Lube was super key even at this point, so we used his favourite so that he was definitely comfortable. He thoroughly enjoyed the prostate massage, and watching his eyes roll back when I hit the right spot was amazing.

For the big event, we had plenty of foreplay so we would be definitely ready. After the foreplay, I blindfolded him so that I can put on the strap-on and there could be a big reveal. We got into position, and because we warmed up with finger play he was already well lubed up. He lubed me up and we were ready to go. It was difficult to find a good position for the toy where it went in best, but he kept guiding me. We started really slow, thrusting little by little and gradually getting deeper. By the time I was doing full thrusts we played around with my position (lying over him, sitting up and holding his legs – which he enjoyed thoroughly) and the depth and speed.

3 or 4 times he asked for me to put more lube on, which of course I did straight away. I did slip out a couple of times, but again he helped guide me back in. At points I pulled him up to rest on my legs a little, which helped me slip in and proves patience and trying different things are key. Once we had a good explore, he asked permission to play with himself (which I helped at one point, his eyes really rolled because I was still thrusting at that point) until he came, then we showered and cleaned everything up before talking through it all. We decided it’ll be something we could do again in the future, but only very occasionally. Turns out he enjoyed the finger play best, so shows you don’t know what you’ll like or not like until you try it! We then had ‘normal’/hetero sex a few hours later :wink:

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Glad to hear your exploration went well for you both and it was enjoyable for all involved

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@daisy0211 thanks for the awesome story.

What are your thoughts on your partner wanting to try pegging?

I guess it’s becoming more the norm as couples are more open to try things, my wife and I have done it and will do it again in the future, I’m just curious what women think about it, does it bring you both closer having the trust in such a vulnerable position? Do women think its NOT MANLY to enjoy anal play?

Sorry for all the questions, thanks again for sharing.

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@JS90 thank you so much for the questions. The reason I shared is so people could!
Honestly, when he told me I was very emotional (in a negative way), and if I’m completely honest it was because of the stigma that anal sex is considered gay. With a lot of talking with my partner (him explaining that he imagines me with a strap on, not a man doing it) and a lot of research on how common pegging is, the stigma quickly died.
I also found there was a stigma around anal sex that it could be quite ‘rough’ and couldn’t be intimate. Again through reading and research it became clear that it could also be slow, sensual and close. Another stigma dead.
My partner had made it clear for a while he enjoys anal play (he used to do it only in his ‘free time’, I can’t imagine that anymore) and we both like switching between being sub and dom, so I don’t think I was really surprised when the topic of conversation came up. I’ve also understood about prostate stimulation, and if wanting (what can be) a seriously intense orgasm is ‘not manly’ just because something is going up your butt, then grow up, do some reading and get with the times.
At the end of the day everyone gets a different sense of enjoyment from different experiences, and I’ve always accepted and understood that.
I loved looking after my partner in a way only I have and a way only I will (we are each other’s first in this sense). I also loved putting on my penis in front of the mirror (for myself) in my favourite lingerie! It made me feel unbelievably sexy and confident and powerful. I think all women should try wearing a penis, even for just shits and giggles but most importantly to help break down so many stigmas that hurt so many people

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@daisy0211 Thanks for answering all my questions.

I seem alot like your partner.

My wife and I have very high sex drives but were both very vanilla when we met, I’ve always been keen to try other things thanks to porn and adult educational podcasts.

Your partner is 100% right saying that imagining he will be pegged by his partner with a strap on and not think its another guy.

It’s hard to explain but I see the difference between gay and straight men is the attraction to members of the same sex and that sexual enjoyment shouldn’t label someone… hope that makes sense.

The connection between you and your partner after anal definitely brings you closer, sharing something so vulnerable

I hate that most porn today involving Strap on sex is Femdom and rough which doesn’t help that stigma, I think one couple (Mary cherry) have intimate videos involving pegging.

I’d love to send your post and reply to my wife and see her response… even if it means she spends 5 mins in lingerie and the strap on ha also look forward to seeing more thoughts from more men and women, hopefully this post will open the door for more couples.

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@daisy0211 your husband is a very lucky man. I’m still trying to convince my wife to do it to me.

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@JS90 please do show my story/replies to your wife (or anyone you know that is thinking about pegging for that matter), I hope she will find it useful! Or at least she will enjoy the read!
@KentCouple1990 he’s not my husband, but hopefully some point in the future he will be :wink:

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I think after last night he should be making plans to get a ring :rofl::rofl:

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A shame your first try wasn’t what you expected. We find missionary or any face to face position the most difficult to get comfortable. Might I suggest that you try cowgirl (cowboy?) with him on top. That way he can control the speed and depth of penetration as he wishes. That, and her bending me over a table, sink or worktop, is our favourite position for comfort and enjoyment.

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@rockstar neither of us had any expectations, and my bf made it very clear that he especially didn’t. Our only aim was to have fun and explore new things.
We are going to try and perfect it in the future, so thank you for the suggestions. Cowboy especially is one I want to try :slight_smile:

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I think this is a great thread and you’ve all been really open about your thoughts. I wish more people were as open minded and non-judgemental about it…

Personally, the idea of being with a guy just leaves me feeling cold and it’s a total passion killer. The idea of a woman dominating me (sensually and carefully) is an incredible turn on whatever the situation. It’s on the bucket list and I hope to tick it off this year!

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I have enjoyed solo anal play since I was (18)
so the first time my wife surprise me with a finger I already knew that it was something I could get in to she started with just running her finger a cross my butt .
and eventually inside and me being young and dumb
“I was like we should go buy some anal beads”
mind you we’re 20 ish just married and have never been with anyone else.
she may have a very basic vibrator at this point I don’t remember.
but to the point young just married and almost no toys.
and here I am bringing in anal toys.
and to her credit we try them.
she has no interest in anal so just on me.
It’s all going well until one day with zero discussion I bring home the cheapest strap on they made.
I will never forget that thing bright pink the underwear and dildo one piece both made out of rubber.
Needless to say she was taken back a few steps by that but we tried anyways.
It wasn’t until much later that the questions came out that should have been ask before it was even purchased but now their fuel by anger jealousy and fear.
to say I did everything wrong is a understatement and it left her and me questioning everything.
I’m so happy you guys did it right.
as for us we are better 20 years later but still working at it

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@Peggingand_fun you’re comments on my previous thread helped me and my partner so much leading up to the event, we cannot thank you enough :slight_smile:

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Editing title as “all the details” might encourage people to post comments which break the forum rules

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I am so glad you both had a good experience. I so want to try this with my man but he is strictly a no anal zone, so obviously I respect that. I would. Lov nothing more than to give him a prostate massage though as I honestly think it would blow his mind and I would feel so so so hot doing that for him.

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@daisy0211 edited by mod Glad you both enjoyed it! It’s certainly something I’m interested in trying! How big was the dildo on the strap on that you used? :grin:

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@SteelA1 I used the Lovehoney Perfect Partner Unisex Hollow Strap-On 6 Inch, so 6inch in length and circumference. In complete honesty I got it because it was on sale and I didn’t want to spend too much on something that we wouldn’t get much use of. I already knew what size dildo my bf used so I knew it wasn’t too big for him, which was the most important thing though

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@Bex212 do you know why it’s a ‘no anal zone’? Maybe have a chat with him but I know it’s easier said than done sometimes!
For me, the actual act of giving a prostate massage wasn’t what I enjoyed, but just watching my bf go from blushing to his eyes rolling back when I hit the right spot was what I loved. Telling my bf that he was blushing just to get his reaction was also amazing :heart_eyes:

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Sounds good! I bet you’ll be doing it more often from now on and I wonder if he asks to go bigger :grimacing:

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Hey bex,
We did both really enjoy it. It’s very difficult to approach a topic where it’s a no go zone.
Myself and daisy went through that for a period of nearly 2 years where we were on the same situation. All I can really say is that opinions can change. But we made it out of that no go zone through communicating.

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