Category: All Sex

My Boyfriend and I tried anal play and now he feels disgusting.

I’m a 20 year old female and my boyfriend is 21.  We decided to try something new and it started off with me eating his ass, which he liked.  I then put my finger in and he loved it.  When I tried to put two fingers in, he orgasmed.  This was the first time he has finished so quickly.  He usually takes between 30-60 minutes even with penetrative sex to orgasm and he never orgasms just from head.  But this time, he jerked off as I played with his ass and he came within just a few minutes!

After he was done he had a weird look on his face, got up immediately and went to the bathroom.  When he came back he wouldn’t even look at me. I tried to get him to open up and he said that he liked it but he’s angry and feels disgusting for liking it. I told him I won’t bring it up again unless he wants to try it again at some point and he replied saying he would do it again in an instant, he just feels so disgusting and emasculated for liking it.

I tried telling him that our bodies are weird and why should we limit ourselves when there is so much pleasure to be found everywhere. Plus every first time is an emotional experience but he wouldn’t even look at me or say anything.  After about 30 mins he told me he needs to go and went back to his place.

I think this may be stemming from his upbringing (we are both from very strict Asian backgrounds) and it sucks seeing him feel so disgusted with himself when it’s something he just found out he enjoys. I want him to be happy and feel good and I’ve never seen him feel this way about himself, especially when it comes to sexual things

How do I handle this without making the situation worse ?

Venice’s response to boyfriend anal play

Personally, as an Asian woman, I do not think Asian culture is any different than masculine men culture, it’s universally embarrassing for most straight men to first come out about enjoying fingers in your ass.  Even now, in a lot of urban, more masculine cultures in America, some men won’t even admit to masturbating.  It’s a sign of weakness.  Why masturbate when I can get pussy?   And a lot of men, especially the immature ones in their early teens to late 20s, still get embarrassed at the thought of eating pussy.   

Say what?!  Whether it be gross, emasculating, or a sign of being a cuck…why would they eat the hole other men have fucked?  And of course, all of these reasons are immature and dumb as fuck!  Excuse my French.

With that said, I believe this has changed a lot in recent years.  Because now it seems men are open about not only eating pussy, but have no issues admitting they love to dive face first into a woman’s ass.  I believe social media has helped open up men from all walks of life, to admit what they enjoy, because social media still has a bit of anonymity to it.  And the truth is, men have always loved to dive in and “accidentally” lick our asses, low key.  And a lot of them didn’t mind a wandering finger during a blow job.

Before I get into answering your question, let me make sure you understand my perspective.  I am the Asian girl who wrote “A Total ‘How To’ Woman’s Guide To Licking Your Man’s Ass.”

In other words, I am all for anal play, ass play, pegging, or whatever else a couple can do with each other’s bodies. However, this doesn’t happen over night.  Most men, especially after trying something some people consider “gay” for the first time, will show some sort of embarrassment. He isn’t going to take it up the ass and be proud afterwards.  He has to be careful, he wants to know you understand he isn’t gay.  He also possibly feels he has to overreact to ensure you understand, this isn’t something he would “normally” do.   And what’s also interesting, he may have the same reaction with all the other women he dates in the future.  For whatever reason, even in an open minded relationship, men can’t just come out and say they love ass play.  It’s a gradual admission.

Just be patient, accepting, and make sure you keep letting him know that you don’t consider anything the two of you can do to each others’ bodies gay, or even a sign of gayness.  Nor should he be emasculated.  Give him time.  Eventually you will find yourself diving down to his ass, kissing him afterwards, and enjoying what a couple can do with each other, without the shame that comes along with it.  It’s a sexual maturation process we all go through.  And I mean ALL OF US.

Ryan’s response to boyfriend anal play

Just to start this off, I’d like to link to one of the most masculine guy in the world, who openly admits he prefers transwomen to non transwomen.   I can’t go into each video or find the exact moments, but his name is Big Lenny and he is extremely open with his sexuality.  He does not say he is gay, but he keeps it no secret that he likes butt play, likes beautiful women with penises, and would tear your head off if you questioned his masculinity.

The Delray Misfits – YouTube

Obviously your boyfriend is embarrassed.  Most men do not just throw the legs up and let a woman dive in unless it’s something they thought about privately at some point.  I am sure if you discussed something new and found his ass up in the air enough for you to lick it, he knew exactly what he wanted to try.  Sometimes when we expose ourselves to our kinks and leave ourselves extremely vulnerable.  Yes, depending on the kink, we get overwhelmed with embarrassment as soon as we orgasm.  The first time I orgasmed in front of Nessa, I cried.  I just felt so weird, so exposed, so wrong (wtf), that crying just felt right for me.  It was something I had only done by myself up until that moment so I felt super vulnerable and didn’t know how she’d think of me.

We are taught to do anything sexual alone and keep our kinks hidden.  When exposed, we feel vulnerable and exposed.  Sometimes the kinks we enjoy, aren’t perceived as masculine, so it’s also emasculating.   It isn’t uncommon for us to put on a show, to make sure the person knows, “This isn’t the normal me.  I am so much more manly and tough, I’d never cum to a finger in my ass and be proud!!!!   Roar!  I am a man, hear me roar!”

So we put on a little “show.” Acting upset, shocked, or just letting the other person know how disgusted we are, may be some authentic emotion, but it is also to save face.  And we’ll save face until we feel comfortable that you didn’t judge us, you accepted our kink, and it’s okay to enjoy what we enjoy.  So far, you have done everything right!  You said all the right things.  You were patient.  You have now went through all the obstacles you think he is going through, from being embarrassed or emasculated, and are starting to understand, he isn’t gay.  He just likes anal play.  Now, imagine all the women that first play with their man’s asses and question his sexuality.  This happens all the time!  And good for you,  you didn’t do that.  But just know, he has his own process he has to go through to ensure you understand him.  Give him time.  His kink is exposed.  He obviously really enjoyed it.  It will only get better from here, as long as you keep an open mind.