Training a Anal Virgin
Copyright© 2025 by bryan5151
Chapter 1
True Story Sex Story: Chapter 1 - it's always fun to get a new lady into anal sex
Caution: This True Story Sex Story contains strong sexual content, including BiSexual True Story Anal Sex Cream Pie
Some years ago, we were lucky to meet a nice couple on a swingers site, Joe and Sandy, although not as kinky as us, they were good fun and we met them as friend’s too, it was nice when Sandy rang to arrange a meeting for Saturday night, and asked about our website, saying she had seen we liked anal sex.
I told her we both did, this shocked her a bit, and she asked more questions, then said she had wanted to try anal, but Joe wasn’t into it, and that was as far as she had got, I told her if she wanted to try anal Saturday night, to just go with what we did, and let us work it out for her.
They arrived around 4 pm Saturday, Lyn and Sandy went to try on some dress’s, that’s what we told Joe, Lyn was showing Sandy how to use our douche, every now and then they came out to show us a dress or two to keep Joe happy.
We had a bbq then got into the spa, it didn’t take Lyn long, she had Joe sitting on the edge and was sucking his cock, I took Sandy into the bedroom and started working on her, licking and then fucking her pussy, then asked was she ready to try anal, a sly smile was all I needed.
I got her worked up, fucking her pussy harder, building her up with a good few orgasms, then with a bit of lube, slid a finger in her ass, she held firm, her orgasm got stronger, then a second and third finger went in her ass, she loved it, pushing back firmly onto my finger’s, her orgasm louder than normal, so it was time to try her ass with my cock, with a bit of spit, I eased the head into her virgin hole.
Sandy jumped a bit but then pushed back, my cock slid in easy, now with slow easy strokes I was fucking her ass for the first time, each thrust more of my cock went in, then with one good push I sunk the full length of my meat in her ass.
I gave Sandy the amyl telling her to try it, she wasn’t sure, but trusted me, sniffing it I felt her ass relax, so I fucked her harder now, then I told her to take more amyl, forcing more cock into her receptive ass, the first of her anal orgasm hit her in a big way.
Each orgasm got stronger and louder than before, every now and then she let out a low scream as her body shook, I knew the other’s would have heard this too, I didn’t give her any mercy, pounding her ass so hard she would be sore for days.
When I heard the air pump go on in the spa, I told Sandy, Lyn would be introducing Joe to anal sex now, she looked at me, I said she’s going to slide his cock in her ass this time, a smile came on her face, she got into the amyl more, her anus relaxing nicely, my cock tried to destroy her ass, every inch going in and more, as a finger slipped in next to my cock.
I fucked her for ages, she was loving my cock in her ass but I held back, keeping my cum for later, when I heard the air pump go off, I told her to turn over and lay on her back, I pulled her legs up my chest and returned my cock to her ass.
She had a few more orgasms, then Joe and Lyn walked in, he looked at Sandy, then looked again, it took awhile before he realised I was fucking her ass, his face went strange, but his growing cock told me he was turned on. Lyn got on the bed, and sat over Sandy’s face, swatting over her face she pulled her ass cheeks open, Joe’s cum began to run freely from her asshole, Joe saw this and of course realised where his cock and cum had been, his cock now grew to full size, and he was stroking it.
My balls couldn’t hold back any longer, unloading my cum deep in Sandy’s bowels, flooding her for her first anal cum load, as I did, I leant forward and licked Lyn’s ass, then as she got of Sandy I began to lick Joe’s cum from Sandy’s face, Joe let out a moaning noise, he had never seen me do any bi stuff before. When my cock slipped out, Lyn went down licking Sandy’s ass, I told Sandy to sit on my face, she did, and I ate my own cum from her, poor Joe didn’t know what to do, but he was still stroking his hard cock.
As we rested, Lyn told Joe how she had sat on his cock in the spa, and slipped it in her ass, he said it had felt tighter, and that was why he hadn’t lasted as long as normal.
We told him how we had got Sandy to clean herself, ready for her anal fun too, he told us that was why he hadn’t wanted to try anal, because it was messy, but now he was keen to try more.
Soon we started to play again, this time Joe fucked Sandy, quickly pushing his cock in her ass, fucking her hard, I fucked Lyn’s ass, as we both built up speed, I turned to Joe and said, want to try something different?, he looked puzzled but said after this lot, why not, I said right, you’re going to have to fuck all four holes, then pick one, and fuck it until you cum, then tell us who and what hole you have just fucked.
He looked amused but said ok, Lyn put a eye mask on him, and I indicated to Sandy to kneel on the bed, with two fingers Lyn eased his cock into her pussy, he fucked her for a minute or two, then I said ok, next hole.