How to make anal sex less awkward

shaneawi

Tool-Bearing Hominid
Tool-Bearing Hominid
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I want to do anal sex with my girlfriend. She only did it with her ex boyfriend and had bad experiences. She said it hurt and he never prepped her. She said he was only concerned about his own pleasure. I asked her about her thoughts on it and she said I could do it with her.

I can tell she’s not thrilled though. How do I make it not as awkward with her? Anal takes preparation. I want to massage her, finger her, use lube and relax her so she will at least not hate the experience. But I feel awkward doing it because I know she’s just doing it for my satisfaction and has no interest in it. She’s just sitting there silent while I’m prepping her. It feels awkward.

how do I make anal sex fun for her instead of her just laying there not saying a word and possibly not enjoying it.
 

PalmaSailor

Space Monkey
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I want to do anal sex with my girlfriend. She only did it with her ex boyfriend and had bad experiences. She said it hurt and he never prepped her. She said he was only concerned about his own pleasure. I asked her about her thoughts on it and she said I could do it with her.

I can tell she’s not thrilled though. How do I make it not as awkward with her? Anal takes preparation. I want to massage her, finger her, use lube and relax her so she will at least not hate the experience. But I feel awkward doing it because I know she’s just doing it for my satisfaction and has no interest in it. She’s just sitting there silent while I’m prepping her. It feels awkward.

how do I make anal sex fun for her instead of her just laying there not saying a word and possibly not enjoying it.
If you can tell she really doesn’t want it then don’t do it.

if she’s super anxious about it (which it looks like she is) then it won’t end well.

if you want to do it then get another girlfriend that’s into it.

you’d be surprised how many women are
 

shaneawi

Tool-Bearing Hominid
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I understand what you’re saying. In feel like if her ex did it with her so many times and I haven’t done it at all then he’s more dominant than me in her eyes for at least having the balls to go for it
 

Skills

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I want to do anal sex with my girlfriend. She only did it with her ex boyfriend and had bad experiences. She said it hurt and he never prepped her. She said he was only concerned about his own pleasure. I asked her about her thoughts on it and she said I could do it with her.

I can tell she’s not thrilled though. How do I make it not as awkward with her? Anal takes preparation. I want to massage her, finger her, use lube and relax her so she will at least not hate the experience. But I feel awkward doing it because I know she’s just doing it for my satisfaction and has no interest in it. She’s just sitting there silent while I’m prepping her. It feels awkward.

how do I make anal sex fun for her instead of her just laying there not saying a word and possibly not enjoying it.

you need to understand that she is traumatized (as a lot of girls) cause the ex jamed his dick inproperly and cause her pain.... You need to sell her SLOWLY, on annal, without pressure as casual convo....

Tell her most women can get orgasms anally and is a much more intense orgams, and how the girls that worked with you had the similar experienced to her but after doing ANNAL WITH YOU, they could not get enough of it and wanted it all the time...

start by as you are in missionary playing with the deep spot a bit, gentle.... (the little tiere between as and vagina) see how she reacts to that...

then after ^ couple of days doing this and earning her trust baby step it to playing with your WET tip of finger in circular motion with her ass as you are penetrating your dick in missionary no finger penetration yet just the outside.......

then insert a tiny tiny bit of your finger (see how she reacts) make sure you have some type of anti bacterial next to you in the bed cause touching ass to vagina could cause vacterial infection... Hopefully she likes this...

Then go to a sex story or online by the smallest pausible vagina plug fuck her while she is using that for a while to see how she likes it,

then bigger one,

then bigger one,

then time to instert bigger one, when ready your dick, as you instert your dick inside her ass and you are about to cum yell really loud "skills is the name of the mothefuckign game"
 

PalmaSailor

Space Monkey
space monkey
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I understand what you’re saying. In feel like if her ex did it with her so many times and I haven’t done it at all then he’s more dominant than me in her eyes for at least having the balls to go for it
Don’t get hung up on her ex.

@Skills has given you directions below on how to get into it, it needs to be done slow with loads of lube. If you do it wrong she’ll tense up and you’ll hurt her.

you need lots of lube.. I would not bother with the anti bacterial next to the bed, it’s too formal, just don’t put the same finger you put in her arse anywhere else until you’ve washed it.

of you finger her arse when fucking does she enjoy it, or does she pull your hand away?
 

shaneawi

Tool-Bearing Hominid
Tool-Bearing Hominid
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Messages
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I’ve fingered her gently in the butt during sex and oral and she lets me do it and doesn’t say anything. She doesn’t moan or anything either.

last night I gave her a back massage and used some lube to finger her in the ass very lightly just to get her used to it. She just sat there and watched tv. She didn’t say anything. It was really tight though so I need to do it more. I’m just afraid if I mess this up it will turn her off of doing it with me
 

PalmaSailor

Space Monkey
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I’ve fingered her gently in the butt during sex and oral and she lets me do it and doesn’t say anything. She doesn’t moan or anything either.

last night I gave her a back massage and used some lube to finger her in the ass very lightly just to get her used to it. She just sat there and watched tv. She didn’t say anything. It was really tight though so I need to do it more. I’m just afraid if I mess this up it will turn her off of doing it with me
Sounds like she has no interest whatsoever in what’s going down.
Honestly I suggest you move on you’re on dangerous ground
 

Skills

Tribal Elder
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Don’t get hung up on her ex.

@Skills has given you directions below on how to get into it, it needs to be done slow with loads of lube. If you do it wrong she’ll tense up and you’ll hurt her.

you need lots of lube.. I would not bother with the anti bacterial next to the bed, it’s too formal, just don’t put the same finger you put in her arse anywhere else until you’ve washed it.

of you finger her arse when fucking does she enjoy it, or does she pull your hand away?
well the problem is if you go from dick to ass or finger in ass to vagina could cause a vacterial infection to her vagina, everything else i kind of agree on...
 

Skills

Tribal Elder
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I’ve fingered her gently in the butt during sex and oral and she lets me do it and doesn’t say anything. She doesn’t moan or anything either.

last night I gave her a back massage and used some lube to finger her in the ass very lightly just to get her used to it. She just sat there and watched tv. She didn’t say anything. It was really tight though so I need to do it more. I’m just afraid if I mess this up it will turn her off of doing it with me
you know is ok to talk to her, "baby how does it feel" "do you like it" get feedback bro...
 

shaneawi

Tool-Bearing Hominid
Tool-Bearing Hominid
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Messages
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I definitely get feedback and as I’m prepping her she says she’s fine. She’s fine with me using a buttplug too. I think I’ll try that as well.

any recommendations on best beginner positions for anal?
 

PalmaSailor

Space Monkey
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I definitely get feedback and as I’m prepping her she says she’s fine. She’s fine with me using a buttplug too. I think I’ll try that as well.

any recommendations on best beginner positions for anal?
Look man she’s sat there watching TV while you’re fingering her and you’re getting no input whatsoever from her.
Honestly, this is not the way to go, the TV shouldn’t be on. You’re getting no make out, she’s not sucking your dick, the message here is she’s not interested at all.
I don’t even know why she’s there.
It’s a dangerous position to be in because she’s simply not 8nterested.
Do yourself a favour and dump her and get one that’s actually interested in you, I can assure you, this one isn’t, and if you persist with her it could get nasty.
A woman that’s interested should be doing some leading, and this one isn’t.
 

shaneawi

Tool-Bearing Hominid
Tool-Bearing Hominid
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Messages
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I told her to put the tv on while I gave her a massage on her back and fingered her ass. She’s not interested in anal, that doesn’t mean she’s not interested in me. This morning she climbed on top of me naked when I was sleeping, gave me a blowjob and we had sex. The other day she texted me at work and told me to come home because she wanted to have sex.

If her ex jams a penis up her ass for 4 years, she’s probably not gonna be super into anal, that doesn’t mean she’s not interested in me. Almost every other day she brings up having kids with me out of the blue. My goal is to get her comfortable with anal. She’s already said she’s okay with me doing it. Some girls just aren’t as into it as others
 

PalmaSailor

Space Monkey
space monkey
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I told her to put the tv on while I gave her a massage on her back and fingered her ass. She’s not interested in anal, that doesn’t mean she’s not interested in me. This morning she climbed on top of me naked when I was sleeping, gave me a blowjob and we had sex. The other day she texted me at work and told me to come home because she wanted to have sex.

If her ex jams a penis up her ass for 4 years, she’s probably not gonna be super into anal, that doesn’t mean she’s not interested in me. Almost every other day she brings up having kids with me out of the blue. My goal is to get her comfortable with anal. She’s already said she’s okay with me doing it. Some girls just aren’t as into it as others
You told her to put the tv on?
I give up.
 

Will_V

Chieftan
Staff member
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I told her to put the tv on while I gave her a massage on her back and fingered her ass. She’s not interested in anal, that doesn’t mean she’s not interested in me. This morning she climbed on top of me naked when I was sleeping, gave me a blowjob and we had sex. The other day she texted me at work and told me to come home because she wanted to have sex.

If her ex jams a penis up her ass for 4 years, she’s probably not gonna be super into anal, that doesn’t mean she’s not interested in me. Almost every other day she brings up having kids with me out of the blue. My goal is to get her comfortable with anal. She’s already said she’s okay with me doing it. Some girls just aren’t as into it as others
Dude you need to connect with her as you do it, not distract her like she's a dog at the vet about to get the jab.

Ask her what she wants you to do with her ass, talk to her like 'I know you'd love it if I fucked your ass the way you like it' etc. Get her talking, fantasizing etc. Compliment her butt, tell her how much you'd love to see your cock between her buttocks etc.

Sex is an erotic thing not just digging a hole, you need to get her all hot first.

Also, remember the tightness is tension, not the actual size. When she relaxes her ass it can easily take a cock. Your job is to relax her and warm her up so she lets you right in.
 

PalmaSailor

Space Monkey
space monkey
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“not distract her like she's a dog at the vet about to get the jab.”

Hilarious- made my day.. lolllz
 
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