This is permanent spank bank material for me. Anal was always a hard limit for my SO (we’ll call her Chloe). For context she has very pale skin, D cups, brown hair, freckles and medium height. We talked about fantasies and such and it was something I was open to but Chloe was not at all interested. We compromised with a small plug. She didn’t love the sensation though it did make her orgasms more intense. We had some friends that we spoke very openly with who admitted they tried anal and hated it because they stupidly used zero lube. Chloe and I were talking later and she couldn’t understand the appeal if anal was so painful. I told her they were doing it 100% wrong and it’s never supposed to hurt and explained that the pleasure comes from all the sensitive nerve endings down there. I think that got her curious. The topic didn’t come up again for some time.
One night we were having a particularly steamy fuck session with candles and rose petals and all. Chloe was on her back on the bed while I was standing and slowly thrusting my cock in and out of her pussy. Her legs were wrapped around my back holding me close which always drives me crazy. I pulled my eyes away from her beautiful tits to see a wild look in her eyes. “Can you get one of our toys?” Chloe asked me. I inquired which one (we have the typical dildo, wand, nipple clamps, handcuffs, etc). She hesitated a bit before saying “.. ummm.. get my plug”. To this point she had never asked for the butt plug, it was always my idea. Since we got the plug, anal had become more and more of a fantasy for me so I quickly got it out of our sex stash.
She knelt up on the bed in doggy style and presented her ass at me. I warmed the small metal plug up with one hand while slowly applying lube to her tight little hole with my other. I pushed my finger in knuckle deep before removing it and slowly pushed the plug in her ass. I could tell Chloe was enjoying it as her breathing got deeper. I was hard as a rock at this point so I joined her on the bed and pushed myself in her pussy. She was so wet that I had no problem speeding up until I was pounding her into the mattress. As mentioned, she cums the hardest with her plug in and her pussy contracting brought me to the edge as well.
We moved around to cuddle while my cum leaked out of her pussy and I asked what brought her to ask for the plug. Chloe replied that she wanted to get a little kinkier. My personal rule is to respect boundaries she had set so I didn’t ask if she was reconsidering anal but I did suggest one of those online sex quizes. We went through it while still naked on the bed and as I guessed we both answered affirmative to anal sex. Chloe was understandably nervous but she said we could work up to that someday. We were hot and bothered from exploring our fantasies so she bent over the bed.
I got to work on her pussy again and fucked her hard as she grabbed the sheets. “play with my ass” chloe moaned. I slowed down and boldly asked her if she’d prefer I just fuck her ass instead. She hesitated but said yes, just go slow. I probably didn’t need lube with her pussy wetness all over my cock but I applied a generous amount just in case. I slowly pushed the head in her ass which was tight but warmed up enough from the plug. After checking that she was okay I pushed the rest of my way in her ass. “OH my godddddddddddd” Chloe moaned. Her words contained more simultaneous surprise and pleasure than I had ever heard from her. Her ass was so tight and a much smoother texture than her pussy. She wanted it faster. I obliged. Chloe was already an anal pro and the faster and harder I got the more hysterical she became. We added a wand vibrator to her clit and she came so hard she pushed my cock out of her ass with the clenching. I got back inside and pounded away until I shot my cum deep in Chloe’s ass for the first time. Afterwards we talked about how it was. She said there was a bit of discomfort and “pooping feeling’ but it was mostly really pleasurable so it probably wouldn’t be an every-time thing but she’s opening to doing it again.
The next day we were at our respective jobs when Chloe texted me. She had been thinking about the night before. We started talking about our ass fucking adventures and she texted 4 words that drive me wild “my panties are soaked”. We sexted the rest of the day and met up to refuel her car (she forgot her purse that day). We were both horny enough that if it wasn’t such a busy area we would have fucked in the parking lot. When we got home, I don’t even think we closed the car doors in such a hurry to get to the bedroom. Chloe wrapped her arms around my neck and stuck her tongue down my throat before turning around and pulling her jeans down. It was a bad day for her to wear lace up boots so they stayed on and just had her pants around her knees. “Fuck. My. Ass.” she demanded. Her pussy was dripping. After applying some lube I got to work. As mentioned, she takes it like a champ and I can fuck her ass at full force after a few seconds to adjust. That part about anal being an occasional thing? Total bullshit. We do anal probably 80% of the time and fucking her ass is the most reliable way to get her to cum within less than 2 minutes. Chloe is my little anal slut now.
Source: reddit.com/r/gonewildstories/comments/gus7sk/when_mym_sof_decided_she_loves_anal
Hot. More paragraphs though, please.
The butt plug loosened her sphincter and she naturally looked for more. Wonderful. Best to both of you. Love it when they ask for it like that. Treat her well,I see that you do
It just goes to show you how good anal can be if done right.
Beautifully written
Damn good. Do share more.
Excellent work sir! The world needs more men like you, so you can make more women like her.
Super hot! We just tried it for the first time this weekend; I’m looking forward to being able to adjust that quickly and get pounded right away.
Just wow…hot as hell. Lucky dude