Intimacy: Today, my boyfriend and I decided to try anal sex. When he was...

By Picaresque - 26/02/2009 17:57 - United States

Today, my boyfriend and I decided to try anal sex. When he was done, I turned around to see him holding a strap-on with a smile on his face and said 'Now, do me'. FML

I agree, your life sucks 286 071

You deserved it 68 246

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Same thing different taste

By Anonymous - 19/04/2010 20:36 - United States

Today, my boyfriend told me he loved me for the first time. He followed it with, "Want to try anal?" FML

I agree, your life sucks 41 689

You deserved it 9 748

What what?

By Anonymous - 12/04/2022 16:00

Today, my boyfriend stuck his finger in my butt and I liked it, but I can’t ever tell him that or he’ll get that smug look on his face like, “I told you so, let’s have anal now.” FML

I agree, your life sucks 518

You deserved it 1 498

By Anonymous - 23/02/2013 18:27 - Denmark - Copenhagen

Today, after months of a very healthy sex life with my boyfriend, he asked me to let him try anal. I'm dead-set against it, so I tried to let him down easy by jokingly saying that I would, but only if he let me try it on him first. He said, "Sure." Fuck. FML

I agree, your life sucks 29 325

You deserved it 48 698

Experiment!

By anal-retentive - 23/06/2016 20:00 - United States

Today, in an attempt to spice things up a bit, my boyfriend and I discovered he takes it in the butt better than I do. FML

I agree, your life sucks 15 348

You deserved it 4 338

Instructions

By Anonymous - 31/03/2009 05:40 - United States

Today, my boyfriend and I had sex for the first time. After what seemed like an eternity of waiting, he finally entered me, then paused and asked me, "What do I do now?" FML

I agree, your life sucks 143 632

You deserved it 16 457

By Anonymous - 29/12/2010 11:25 - United States

Today, my boyfriend told me he loved me for the very first time in three years. Apparently, all it took was anal. FML

I agree, your life sucks 37 698

You deserved it 13 305

You're welcome

By Anonymous - 04/06/2025 13:00 - United States - Lincoln

Today, after having sex with my boyfriend, he pulled up his pants and said, "There you go." FML

I agree, your life sucks 328

You deserved it 125

Nice try, chief

By Anonymous - 04/04/2011 01:46 - United States

Today, while discussing having sex for the first time with my boyfriend, I asked what method of birth control we should use. He replied, "Anal." FML

I agree, your life sucks 53 013

You deserved it 15 202

The best method!

By Anonymous - 04/01/2020 18:00

Today, while discussing having sex for the first time with my boyfriend, I asked what method of birth control we should use. He replied, "Anal." FML

I agree, your life sucks 3 013

You deserved it 967

Preparation

By Anonymous - 18/08/2022 12:00

Today, I agreed to anal with my boyfriend, but when I told him anal takes prep, like stretching and lubing, and you can’t just jam a knob up there like in a porno, he lost all interest, asked for a blowjob, and when I said no, he started sulking. I struggle to remember why I’m with him. FML

I agree, your life sucks 1 652

You deserved it 490

jSOPURE 3

Thursday 26 February 2009 23:10

Do unto others...

SweetPotato 0

Thursday 26 February 2009 23:03

Go him! Prostate stimulation is great for guys! Did he like it???

Comments

rmeyer6 0

Thursday 9 June 2011 1:10

that's weird that he had a strap on....

ilovepaco 0

Saturday 11 June 2011 21:31

eww please tell me you didnt do it....

payableondeath 0

Wednesday 15 June 2011 5:31

gay gay gay

jinxy2012 5

Friday 23 February 2018 9:38

Aunt nothing wrong with a little or pegging lol

Paul B. Gyurcsanszky 14

Friday 25 May 2018 6:32

He just watched Deadpool, didn’t he?

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Keywords

Miscellaneous Stalker My ex Coworkers Love Internet Relatable AITA Pokémon Awkward Work Parenting Kids Annoying Shopping Underwear Jealousy Parents Thief Suspicious Sex Intimacy Family NSFW Birthday Gifts I need your advice Accident Abuse Moving home

The Top

Today, I drove to a job interview. I had to sneeze, but because I was driving on the highway, I didn't let go of the wheel to cover my mouth. I didn't know the sneeze was a "productive" one until I was sitting in the interview, looked down at my new blouse, and saw the giant lugie sitting there. FML

I agree, your life sucks 37 420

You deserved it 8 944

Today, a man was struggling up some slippery steps with a pram, when his sunglasses fell from his head. I hurried to pick them up for him, as he had no free hands, but instead accidentally stood on them, snapping them in half. FML

I agree, your life sucks 24 390

You deserved it 16 932

Today, I went to the restroom at school and when I finished my business, I noticed there was no toilet paper. I then began to wait, hoping that a janitor would come by with extra toilet paper. It wasn't until an hour later that I then realized there was four extra rolls hidden behind the toilet. FML

I agree, your life sucks 10 932

You deserved it 53 986

Today, my fiancé nervously sat me down for a "serious chat". The chat wound up with him asking if we could postpone our wedding, because his World of Warcraft guild had a raid scheduled for the same day. FML

I agree, your life sucks 56 956

You deserved it 10 781

Today, the landlord of our building constructed a bathroom in the space under the stairs, outside my office, on the other side of a thin wall. He must have some kind of bowel disorder, because now I get to hear the sounds of his loud, wet and gassy pooping several times per day. FML

I agree, your life sucks 30 078

You deserved it 2 600

Today, I am still finding glitter in my ass crack after a concert last night that had a confetti cannon. Thanks Marilyn Manson, I feel so metal now. FML

I agree, your life sucks 30 752

You deserved it 6 388