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1.
To "bottom out" is when one is having sex and the penis reaches the cervix, or the top part of the vagina, and can go no deeper. This can be referred to as "bottoming out," or in the past tense as "bottomed out."

It can be either painful or pleasurable, depending on the girl and how extreme the bottoming out is.
Man, I was fucking this chick last night and she told me to stop cause my dick was so big I was bottoming out on her.
Por ponnor 26 de septiembre de 2012
 
2.
Bottoming out is a when ones rectum peeps outside of the boundaries of ones sphincter, usually taking place after too much anal intrusion.
Phoenix Marie is Bottoming Out 110%, all this anal sex is really taking its toll on her sphincter
Por MelvyntheMelt 29 de noviembre de 2010
 
3.
Having sex with a group of people then asking for them to knock you out by any method, preferable by a punch or punches to the face. After you are knocked out then the group proceeds to have sex with your unconscious body.
Aaron Romero enjoy's bottoming out in his free time. He often has bruises from bottoming out.
Por Bottoming out pro 28 de octubre de 2009