Generally speaking, if I bring up double penetration, you probably think of some cheesy poolside 80s porn. A woman with bleached and permed hair, straddling one man, his cock inside her pussy, and other kneeling behind her, his cock in her ass. The synth disco is playing, and the sapphire water of the pool is lapping at the edges as the sun beats down on their perfectly tanned and oiled bodies.
There is likely no shortage of discarded silver and pink spandex strewn about the deck, and that’s only what the boys had on!
That is legitimately a double penetration, but the double pen can be so many more things than just that. Any time two objects enter at the same time, it is technically a double penetration. I also think there has to be three people involved for it to be a legit double pen, but maybe others would disagree.
Dildos, fingers, vegetables—these all count!
If you do decide to go for it the old fashioned way, here are a few ideas.
One man under and the other doggie style is going to work the best, but figure out what works for you and take it slow.
Order of insertion is a consideration. The walls in the rectum are more fragile than in the vaginal, so it might make sense to insert into the anus first and the vagina second. Also, if you haven’t tried this before, you might want to go gentle on the ass and not pound it while the vag is also full. Just saying that a pleasant experience will make for repeat customers.
Think about who goes where when. Ass to vag, and ass to mouth, or two cocks switching between ass and vag can carry all sorts of nasties. Even if both dudes have condoms on, the woman can still have troubles on her plate with all that switcherooing.
People in 80s porn were used to having eighteen-wheelers driven up their ass three times a week, so the gold standard for what those asses could take should NOT be your metric.
If there’s going to be a double penetration going on during a threesome, it makes sense to let the woman know about it in advance. If you just spring it on her in the middle, there’s a possibility that things may come to a screeching halt. Boundaries should always be broached ahead of time. Remember, she’s the one who is getting two objects shoved in her, so it makes sense to let her control the pace.
As always, condoms and safe words are your best friends. Lube is a great friend too!
Tell us what you think