penetration 

Penetration is the medical term for the penis entering into the vagina. It's a good way term for talking about sex if one wants to seem mature. Even if you're a dirty little pervert, you'll sound like sex is more than just an emotionless action caused by hormones if you call it 'penetration' rather than 'fucking around,' 'doing it,' etc.

Dude 1: Did you fucked your girlfriend last night?

Dude 2: Penetration occured and I depostited my semen inside of her vagina.

Dude 1: What the fuck? You're a frat boy, you don't talk like that.

Dude 2: I know, but I sure sound mature, don't I?

penetration by Tit For Twat January 31, 2007

One-Eyed, One-Horned, Flying Purple Penetrating Fist Pumping Midget Guido Roofie Slipping Panty Bandit 

A mystical midget Guido that enjoys fist pumping girls that have been roofied in the ass. This often causes tell-tell bruises on the butt cheeks at midget height. His magical one horn allows him to remove women’s panties with out there knowledge. His keen perpetrating skills allow him to steal random item of interest. This can include: Credit cards, iPods and women’s virginity. He is also an Ace with the Mexican Air force.

Rob: Once again my fiancé was perpetrated by a One-Eyed, One-Horned, Flying Purple Penetrating Fist Pumping Midget Guido Roofie Slipping Panty Bandit in Atlantic City.

Jack: Just look on the bright side, its better then cleaning her up after good time’s with good friend’s and some hot lunche's!

Rob: Ya, your right... I'll just Shot! Shot! Shot, Shot Shot! her other but cheek, what a hotmess!

One-Eyed, One-Horned, Flying Purple Penetrating Fist Pumping Midget Guido Roofie Slipping Panty Bandit by bboy domo.... January 18, 2010

Triple Penetration 

This is where a woman is penetrated by three men with the penises in different combinations in the anus or vagina eg 2 in the vagina and 1 in the anus. Hence, quadrouple penetration would be relatively simple by stationing another penis in front of the woman's mouth.
The term is often confused with an "airtight seal" which is where all three orifices are filled with a penis.
Many are skeptical about this as not many women are able to accomodate such a volume plus the restrictions in space make it difficult, plus many men aiming to penetrate a woman would not enjoy the concept of grinding their penis against another man's. However, it has been seen in a small volume of porn films and in the Annabel Chong sex marathon.

That girl was a real dirty loose whore last night, we managed triple penetration!

Triple Penetration by Abrar Ahmed June 4, 2006

Penestration 

To become frustrated from the inability to penetrate or be penetrated sexually.

Despite copius amounts of lubricant, Carl's fat, girthy cock was simply to big to cram into Dana's tight bung hole. After an hour of trying, they both gave up feeling nothing but penestration.

Penestration by Eaton Holgoode November 18, 2015

Double Anal Penetration 

The act of having two peni rammed into ones asshole.

Mrs. Presland (from Lawrence High School) loves double anal penetration; especially with black men!

Double Anal Penetration by Bobby Mcprescott February 5, 2004

Penetration Pendulum 

Entering a man from behind while he is already balls deep in another man, then proceeding to thrust. Thus creating a testicular penetration pendulum.

I love orgies, but the real highlight is kyles balls hitting mine during the penetration pendulum.

Penetration Pendulum by TotalistOfTitans May 12, 2021

testicular penetration 

The true meaning of "Balls Deep"
IT WENT SO DEEP, THE BALLS PENETRATED THE ASS AND EXPLODED EVERYWHERE INSIDE. Can also refer to vaginas as well.

Jayce : Are you ready for some testicular penetration baby?
Ezreal: Oh yes, I'm always ready

testicular penetration by TheMountMaster November 15, 2014