Wife's interest in anal
 

My wife was always a hard no, until one night at the bar we wereplaying pool she was talking shit about how good she was so I said fine if I win I get anal. Long story short I ended up shooting the best game of my life and won, about two weeks later I got to cash in on the bet and to both of our surprise she got off from it. It’s still a negotiation but we both end up enjoying it, hopefully in the future it changes to where she asks for it but being smart I’m not pushing it.

Hard no is an understatement
 

My wife went from actually HITTING me once when I dared to do a quick lick of her pussy while getting ready to fuck her from behind to me recently using a vibrating butt plug on her. In my defense I really couldn’t pass up the opportunity. She was naked on all fours on the bed and was in a get-it-over-with mood. I was right there. I gave it a big lick. Now I ask her which hole she wants and she says for me to pick and just raises her legs up high exposing both. It was a very long process just getting her to suck my cock as well but she came around eventually.

For anal, I just decided one time to gently stick a finger up her ass while fingering her pussy. She didn’t complain but I couldn’t tell if she liked it or not. Each time after I would finger fuck both holes at the same time a little bit harder thinking at some point she would say she didn’t like it anymore. Then one time I was only fingering her pussy while licking her clit to get her to orgasm. She wasn’t getting there so I was going for a toy. Before I grabbed the toy she said, “I think you need to do the other thing.” She didn’t want to say the words but she wanted me to finger her ass. I did and she had an orgasm. I always made sure I had plenty of lube from then on. The next few times I started putting two fingers in her ass and then graduated to a small, well lubed toy. I left the toy in her ass, stuck my cock in her pussy and vibrated her clit to the point of her having an enormous orgasm after a while. The problem was the orgasm was so tight she actually squeezed my cock out of her pussy. The next time I changed to sliding my cock into her ass and then vibrating her to orgasm. That worked better because I didn’t get pushed out. After her big orgasm I asked if she was ok and she said she was so I slowly fucked her asshole and came inside for the first time. It feels amazing as long as it is well lubed. It is warm and tight. I also feel like I am getting away with something. I am pretty sure she tells her best friend about some of our sex experiences but I doubt she would ever tell her about taking it up the ass!

From that point forward, since she knows what to expect and relaxes, and as long as she is well lubed, I can fuck her asshole as hard as I fuck her pussy. Every time I cum in her ass I am still shocked that this was the lady who once said she would NEVER let me go down on her, said she would NEVER suck my cock while I ate her pussy and I am sure anal wasn’t even a remote consideration.

Slow and lots of lube worked for me. Good luck!

Unfulfilled quest
 

You guys give me some hope. My wife is a firm NO when it comes to anything anal; touching, licking, surely not penis.

She’s a great wife, and I’m lucky that after 30 years marriage she still has a strong sex drive. In fact, her sex drive has increased over the past 15 years. We have sex more now than earlier. Either hormones or having an empty nest. She loves oral and swallows every time she infinish in her mouth. She loves to roleplay having multiple partners (another hope, that it becomes more real), and getting more open with nudity. Even has hinted about bringing a woman to bed.

However, anal is always no, and shuts down any activity if I push it. Once, in a wild session, I slipped out and tried to re-enter with no hands. My head pushed against her anal opening and she freaked “wrong hole!!”.

I’ve sort of given up. I love the rest of our sex life, I don’t want her to shut down, but hoping something happens.

Only one...
 

Only one of my previous gf really loved anal sex. She si always in my heart....

we've tried a few times in the past...I couldn't get it in without her screaming in pain and begging me to stop (its not a brag on my part, i just don't think she handles it well). So we don't do it ... :(

For my wife it was always exit only. Then one day after I shaved her bare, front back, side to side, everywhere.....I licked her ass. She loved that. Then, as everyone has said, start slow. Tease it....massage it....and do it at the same time as her clit.

My go to move was two fingers inside on her G-spot, thumb or my tongue on her clit and then my ring finger massaging her ass...then eventually as I pump my fingers inside her the ring finger slides in....

Eventually she got used to toys, then my cock, then more and bigger toys in her ass. Eventually working our way up to a two man double penetration. Talk about a woman having an orgasm with that...holy shit.

Have patience, take your time, listen to her body responses and see how it goes. The wife that used to say exit only now loves taking it in the ass.

Backside
 

I had to get used to it. I wanted to learn to take a dick up my ass because I thought it would be great while I was having my period. It took a while to get comfortable with it but after all these years I now love it. I no longer let my husband fuck me but I have several black lovers with rather large dicks. You have to like it up your ass if you go black. I guess I've stretched some back there and now with a little lube I can take the biggest black dick up my ass, all the way to the root. Hubby enjoys watching me get fucked too. Too bad he never gets any ass anymore. I always like my lovers to come up in me. I like the warm feeling you get and they pound your ass hard. I can come very hard with a big dick up my ass. Here's a picture of me in my early learning days with a white dick coming up my ass.

Do you not know the difference between your vagina and your rectum? That picture is clearly not anal.

???
 

Thought the same thing but could not enlarge so I figured... meh...

Backside
 

I don't see another hole farther back, do you? It was anal with me leaning forward some. It's an old polaroid.