My wife (31F) and I (35M) had been discussing anal and finally took the plunge.
First time happened when I was railing her hard from behind on the bathroom counter. It was a pretty hot and heavy session with spanking and lots of dirty talk. Her (amazing btw) ass was way up so I decided to start massaging her butthole and asked if it was okay if I stuck a finger in. She gave me the go ahead and moaned much louder when the finger went in. We then moved to two fingers. I gently fucked her ass with two fingers for a couple of minutes before she softly pants, “want to try it”?
Of course I did! We spent a few more minutes with two fingers in before I put my head up against her ass. I don’t have a huge dick but it’s quite girthy when I’m very hard (and I was lol) so I was a little worried. I incrementally worked the head in letting her dictate the pace. Suddenly I felt her ass close over my head as we both cried out ‘oh fuck.’ She came right then and there as I held on trying not to also.
Very slowly I’d pull back then go a little farther in. She was loving it. Very vocal “oh my gods” and rubbing her clit. The first stroke that I buried the whole thing made her cum again and likewise me too. We both looked at each other in delightful shock.
The second time was great too. I lasted longer and actually pounded her for a bit. That time she also fucked herself with a toy while I fucked her ass for the first time.
Third time was the best though. She was riding me downstairs in the living room and I was manhandling her ass rather forcefully. She got off and told me to come upstairs.
She goes and gets the lube and a toy and immediately bends over the bed with her ass up. I began massaging her pussy and clit from behind while also fingering her ass with the other hand. She’s already moaning so hard and teasing me with “You want to fuck this tight ass?” and wiggling it around. Next I grabbed a toy and rubbed it around her ass until she whispered for me “put that in and fuck me now.” Yes ma’am! I worked the toy in then slid myself into her soaked pussy. I pushed her head down and asked her how it felt, she moaned “so full.” It felt great for me too as the toy made her even tighter. Some well timed spanks and I felt her pussy grip down on my cock as she came.
For the next few minutes I pounded her hard while fucking her ass with the toy until I could tell she was about to cum again. I slid out and she immediately said, “fuck my ass, now!”
Even with the foreplay her little asshole was still tight against my cock. With a bit more lube I was in, with her now fucking her pussy with a different toy. This was the first time I really railed her ass hard. She was practically screaming as I grabbed her hair and told her how good of a little slut she was being for me to which she responded with “Yeah? You like fucking this tight ass? And “Ohmygod your cock feels so good.” She came twice in about a 5 minute span.
She then got on her back. This was the first time for us to do anal in something different than doggy.
I pushed her legs back with mine and nestled my cock deep in her ass and got to work while she played with her pussy with her hand. I now had the position advantage to suck on her nipples too. Didn’t take her long for her to cum again and this one got me too.
The sight of her on her back with my cock in her ass, her wet pussy, her cock drunk face locking eyes with me and asking me to pound her harder, and everything else made me explode all over her. I was kneeling between her legs but the cum reached her neck. We were both glowing for like 2 days after that and both agreed it had to be in our top 5 of the thousands of times we’ve done it. For reference she normally cums about 1-2 times during ‘traditional’ sex.
Needless to say we love anal and will be mixing it in with out usual sexcapades.
Source: reddit.com/r/gonewildstories/comments/12y344y/fm_wholesome_1st_time_anal_with_wife
Same here (funny same age as you guys) but I’ve yet to use a toy for double penetration tho it’s in the plan
Well told. Thx for sharing! Love anal!
Loved this story, and you guys sound super fun.
missed opportunity: Holesome.
gratz on the sexcapades!
Damn, that was hot!
Greetings and welcome to the pleasure world of Anal……
I used to hate anal when my partner initiated . Now I love it once we tried again 6 months ago. My most strongest orgasms are from anal penetration in prone bone after 2 positon switches in PIV.
Try it with your wife, you penetrating her ass from behind in pronebone. She’ll get anal stimulation , the balls will hit her clit and her soaked pussy will be able to feel you through her perineum wall. She’ll be a rainstorm of cum.
Even in this position, she’ll be able to grind onto your cock , rock her hips side to side and then pulse her cheeks together – feels phenomenal 🤯
You’re welcome and enjoy ☺️…..
Good story. My wife and I are a little older and wanting to try! Thanks for sharing!
I tried it with my boyfriend and it was the best thing I ever did
Love hearing stories of successful anal sex. Most do not understand how hot it is and how great it feels. If you learn how to do it, you will love it.
For the ones that just jam it in, say it hurts, then dont ever do it again….your missing out
I dont get the shares thing. What’s everyone sharing this to?