In Ibiza my wife went out without any underwear a few times. Mostly also plugged. She loved it and I loved it more 
For her there’s an extra risk because menopause fucked up her blatter control. If it wasn’t for that, she would go out without thong a lot more.
I’ve read some of your posts Abbi and you’re definitely more daring than me!
Oh man, talk about daring. I definitely felt the pressure on my bladder a bit while running, but I haven’t had bladder control issues. I hope your wife didn’t have any accidents.
No, she was relaxed and everything went fine.
Hey Jennanymph !
How are you ? How is it going with your anal training ? 
Just wanna make sure that everything is going well. Do not hesitate to ask questions or help on some stuffs if needed
See yoo !
So sweet of you to check in! I haven’t been able to get a new plug yet, so I’m focusing on just the fingers and things are coming along well. I’m regularly doing four fingers and have started to get a bit more of a thumb in. I’m still working out what angles work best for my body and flexibility.
My partner is also visiting later today, so I’m prepping for the big conversation about introducing anal play in the bedroom together, so fingers crossed that goes well also.
Fingers crossed over here as well!
Excited for you. Hope you had fun
Hey there !
Very good to hear that you are slowly managing to get your fifth finger in ! I am super happy for you
Let us know how the talk went !
Hey all, thanks for the well wishes.
The conversation went about as well as I could have hoped. He had never really thought about anal before and was a little hesitant, but said he’d be willing to give it a shot. We decided to go slow, starting with just him fingering me and using my plug until he’s a little more comfortable with the idea, and then we’ll try his penis later.
Let me tell you, though, last night when he went down on me and stuck that first finger in my ass, it was bliss. Top five orgasms of all time for me! And it’s kept me on track for my “only cumming with something in my butt” challenge for September. I’m super excited to see where this goes.
So nice !
Just to understand, how old are you both ?
I am very optimist for the two of you honestly. If he wanna try and see you love it as you described, I guess he will be quite into it. As a man, pleasing the woman with whom we are is a very important thing (and a turn on tho)
Enjoy !
We’re both in college, but at different schools, so we’re having to do the distance thing right now. 
No worries. Long distance relationships do work if it is true love !
Happy new year, all! I thought I might give an update on my personal journey. I’ve been making really good progress, I’m up to 5 fingers. I wouldn’t say I’m fisting, but my thumb can definitely slip in now! Eep!
But more exciting: I finally had honest to goodness penis-in-butt anal sex! It happened when I was home for Thanksgiving, my partner and I finally got a night alone in his parent’s basement.
I was super proud of myself, after all the training I’ve done, the actual night I wasn’t even that nervous. We did our normal stuff, lots of foreplay, and I was already super turned on. I told him I was ready, and we used so. much. lube. We should have bought stock in KY! He went so, so slow. Like, glacially slow. And I worked really hard to breathe and relax instead of tensing up. That was important, since I don’t have as much control over the speed of his dick as I do with my own hand.
The initial entry was still intense. It was different from my toys, like a totally different universe. My plug is just static. But he was warm and alive, you know? And he’s got this… perfect firm-but-soft thing going on that the toys just don’t have. It made the whole thing feel less like an “insertion” and more like he was just fitting into a space that was ready and meant for him. I don’t know how to describe it.
As he pressed himself into me, the stretch got really intense and I had this like… endorphin rush or something. Like this feeling of euphoria and I got light headed… but in a good way.
Once he was all the way in, we just stayed still for a second, and it hit me. It was this deep, full pressure that felt amazing. He started rubbing my clit, and every slow movement sent these insane waves of pleasure through me. With my toys, it was just about the stretch, the feeling of being full. Well, maybe that and a bit of naughtiness. But with him moving, it was like he was hitting this one spot, way deep inside, that just sent this zingy, electric pleasure straight up my spine. It wasn’t a sharp feeling, it was this deep, rolling wave of “oh my god, don’t stop.” It was so intense and so much more intimate than I ever thought it could be. Like, I was trusting him with a part of my body I’d worked so hard on preparing, and he was being so gentle and attentive.
Honestly, it was one of the best sexual experiences I’ve ever had. I really feel like it’s taken our relationship to the next level. Best decision ever, 11/10.
Over the recent holiday break, we were able to do it twice more, at his parent’s place again and at a house party for NYE last night. Three times the charm, I think I can confidently say that I’m fully in an anal relationship now. I get butterflies just thinking about it! I’m so bummed to have to head back to school next week, back to FaceTimes and plugs only. 
Anyways, thanks for letting me share!
Well done and welcome to the “I love anal club”! Hope you had an anal orgasm. It’s the reason for the anal season.
Anal requires such a deep and intimate connection it becomes an addiction. Have fun as you both develop your anal skills.
Thank you, it’s an honor to join the club.
Anal orgasms are my Roman Empire, but unfortunately it hasn’t happened yet. I mean, I came really hard, but it felt more like the anal was a multiplier for my usual orgasm, rather than the deep full bodied experience I’ve heard other women describe. Any tips on how I can get there?
My wife experienced two real anal orgasms and they were too Intense for her. So she preffers to orgasm with the combination of my cock up her ass and clitplay, or me licking her while I dildofuck her asshole.
So seems not everyone will experience true anal orgasms as the best.
As you both learn and gain experience, he can try different penetration angles. In missionary, if he angles his cock up toward your pussy, he can stimulate your G-spot through your rectum.
My wife’s strongest anal orgasms occur when I take her from behind and angle my cock away from her vagina. This hits deeper and closer to her A-spot and pudendal nerve.
You’ll know because is is a whole body experience and quite powerful. Take your time. As you adjust and he develops confidence, it gets better. You might even start gushing during anal penetration. That will blow his mind! Enjoy the journey!
I have anal orgasms in a similar situation (if I understood your description correctly). They really are very intense and a whole body experience. Feels so good how they build up almost kind of like a pressure build up and for me they come in waves, after I have the first if my wife continues to fuck I have some more (2 or 3 more, it varies) until they vanish.
I’m actually a little worried about this. I sometimes get overstimulated during sex and I have to tap my partner to give me a break. It would be a shame if I did all this work to get an anal orgasm and I couldn’t handle it! On the other hand, overstimulation for me usually happens because my partner is a little over enthusiastic with my clit. So if @Colt1911 is right about hitting the g-spot, it could have the makings for a very good time for me! Fingers crossed!