This question is one of the most frequent and most popular that I get sent in from women. I received this question a few days ago and it asked pretty much all of the questions I had myself about double penetration before trying it out I thought that now would be the perfect time to answer it publicly so that anyone with the same worries about DP could find the answers they were looking for.
I’ve also decided to bring my partner (Jack) in to answer this question from the male perspective, so you can get an unbiased opinion from both the male and female perspectives of double penetration.
Question: What Does Double Penetration Feel Like?
A curious female reader of cuckin who wants to remain anonymous, she has been given the green light to play with other men by her boyfriend, she loved it but now she’s curious about dp and what that feels like. The original email can be seen here with full consent to share from the sender.
I really want to know what it would be like to take two guys at the same time.
I just can’t imagine it.
I’ll give you a quick rundown of my situation. Basically, my boyfriend gave me the okay to play with other men, I finally took him up on his fantasy and did it solo with just me and another guy.
It was a lot of fun and I’ve been quite active with this one guy since.
Despite the fun, I’ve still not had a threesome or had two dicks in me at the same time and I’ve been really opening up to the idea of it. When I asked my boyfriend what he thought, he seemed really excited about the idea of me trying it out for real and that urged me to want to try it even more.
I just have some questions.
How does it feel to have two guys inside you at once, there’s not a lot separating your ass and pussy, how does it feel, can you feel both of them?
Does it hurt?
Is it easy once they are both in?
Should I try a dick in pussy and one in my mouth too?
How will it feel for my boyfriend?
How do they both fit inside, do they cross over one another, and will there be a lot of dick touching dick?
I know I have a lot of questions, I just really want to know if it’s a good idea or something my kinky brain is telling me to try that will actually suck.
If it helps you answer, I’ve done anal a lot and really enjoy it and I’m going to try it with the guy I’ve been playing with as he is super hung.
Too long; Didn’t Read: I want to know what it’s like to actually have double penetration sex, I know I am ready for it but I need to know how it works and what it’s going to feel like for me from somebody who has tried it, specifically with hung guys.
Answer From Sarah (What double penetration feels like from a woman’s perspective)
Part owner of Cuckin.com and a devoted hotwife to Jack. I’ve been in loads of threesomes and have been lucky enough to have experienced double penetration multiple times with all kinds of different cocks, ranging from big to small.
The last time I talked about double penetration publicly was in this article where Jack and I were playing around with the idea of trying double penetration.
The other kind where a guy is in your mouth and the other is in your pussy, that happened in my first threesome and the sensation is pretty easy to imagine, but it’s easily one of my favorite ways to be fucked and much easier than double ass and pussy penetration.
The experience was arousing and I felt like a total slut but it was a good sensation, I felt so so satisfied. Feeling a hard, throbbing cock down your throat and deep inside of your pussy is just magical and like a dream come true if you’re a size queen like me.
The kind of dp where both your ass and your pussy are filled at the same time, I finally did try it and it was really fun.
First I tried it with toys, then with Jack and toys, and finally, I tried the real thing with two men fighting for space in my tight holes. It’s way too intimate and explicit to share publically and so, I have shared the whole experience inside our membership.
In my experience using butt plugs, sex machines, and dildos, can be a really good way for getting used to the sensation, but it’s the difference between tickling yourself and having someone else do it, the heat and energy are different and the way the body reacts makes the sensations so much greater. However, for stretching and practice, I highly recommend using sex toys.
Now, the feeling of two men having their way with you, it’s incomparable to anything else.
It can be a little awkward at times, especially when you’re first getting into it and the two guys are trying to squeeze in, however, it does happen eventually and it is tremendous.
Enjoying pussy and ass double penetration has to be one of the hottest moments of my entire life along with the best orgasm of my life too. There’s so much sexual energy and it feels primal to be between two guys who are using your holes and making themselves and you feel so good.
It isn’t the easiest task to undertake but once you do it, the payoff is incredible. It’s hot and heavy, there’s lots of sweat and moaning, everybody is touching everybody and when you get both cocks deep inside of you, it’s like reaching a goal.
The only downside is it can be a little painful if your holes aren’t aroused enough or if you’re in the wrong position and positioning is something most people struggle with and feel daunted by.
When you’re looking for the best positions to try double penetration in these are what you should be attempting (remember to test them all out with your partner and a sex toy to see what feels best for you):
- Reverse cowgirl: She straddles one penis (anal penetration is best for the laying penis) and from the front, she is penetrated by the next penis.
- Missionary and doggy at the same time: Have one lay on his back, the female straddles his penis and leans forwards whilst the second guy gets behind on his knees and penetrates her ass.
- Standing: For this position, one of the guys must lift the female so that she’s secure around his waist and with his penis inside of her, and then standing from behind the other guy comes and penetrates her ass.
- DVP (double vaginal penetration): The female must kneel over one of the penises at the edge of the bed, whilst the other stands behind and enters that way.
- Spooning DP: Laying all together and with the female sandwiched between both guys and laying on one side, both penises can easily glide between her legs.
- Missionary double: Laying on her back with her ankles by her head, one guy slips in from standing and the other crouched over her body slips in from a kneeling position.
These positions will work depending on cock size, height and comfortability so be sure to try them all out with your partner and sex toys beforehand.
Make sure to also use plenty of lube and I mean plenty. There is nothing worse than dryness when being double penetrated and it’ll help ease the cocks inside of you.
With lube or a really wet pussy you also have the problem of dicks slipping out and touching one another and sliding into the same hole, this can hurt so be cautious of this and make sure you’re very aroused before playing with two cocks down there.
I also want to point out that it should never be painful, double penetration is a ‘full’ feeling, there’s a bit of stretching and a rhythm that the two dicks must get into but there should be no pain or forced entry, take your time, take things slow and practice with sex toys to appreciate the sensation and learn what feels right or wrong.
Finally, once they’re done and you’re done, the feeling of being stretched out and used up is totally worth it. It’s a feeling no other has and one that can only be experienced by going through with it.
Breakdown of my (Sarah’s) whole answer: I really enjoy double penetration. The servicing of two men, the way you have two cocks to please, the fact that it then switches and you have two guys focusing on you. How the build-up feels, the moment they both try to get inside you, the sensation, the feeling after it when all your holes are stretched out and you feel like an accomplished naughty slut.
Answer From Jack (What does DP feel like from a man’s perspective)
Part owner of Cuckin.com and a guy who enjoys sharing his partner. I’ve had many threesomes with Sarah and experienced being inside Sarah with another man inside her at the same time on multiple occasions.
It’s Jack here, I wanted to comment on the male perspective of double penetration. I would probably say DP is one of my favorite things to do with Sarah. It’s pretty intense and a deep bonding experience, especially when you do it with a third that you both trust.
I am not worried about my penis touching another penis during sex, it’s just sex and fun after all but I know some people worry about that kind of stuff. Double penetration is up close and personal, you have to be comfortable with yourself and not be grossed out by two dicks touching. Your cocks can accidentally slip, you can feel it through the thin wall between ass and pussy, and of course, cum and all of the other things that come with being hard and aroused are going to happen.
Keeping rhythm can also be a challenge but it’s not too hard if you communicate and keep in sync, I find this also helps me to not cum so quickly by having to concentrate on my thrusts. You must keep the rhythm for her pleasure and to prevent slippage.
I find Sarah gets so wet when she is being double penetrated, she is a size queen but being stretched out by two of us turns her into an animal. We do use lots of lube but her pussy alone could provide enough natural lube for the whole room!
One last thing I wanted to point out is that it gets sweaty, it can be awkward at first and you do have to be prepared for dicks to touch accidentally or otherwise but it feels amazing, the vaginal/anal and cock stimulation brings so much pleasure to you and once you do it, you will never look back.
Key Takeaways About Double Penetration During Threesomes:
- It feels good but it can be awkward finding the right position and rhythm for three people.
- Be prepared for cocks to touch.
- It should never hurt!
- Feeling like a used-up slut is the best feeling.
- Practice with sex toys beforehand.
- Use lots of lube.
What was your experience with DP?
Leave it in the comments and any advice you may have for anyone thinking about trying out double penetration.
If you want to ask a cuckold, threesome, swinging, or hotwife-related questions or get some advice you can send in your question here.
Jack & Sarah
