Fun Getting My Lover to Do Anal
Copyright© 2025 by bryan5151
Chapter 1
True Story Sex Story: Chapter 1 - I had got my new lover to take a finger in her arse, now it was time to fuck her arse
Caution: This True Story Sex Story contains strong sexual content, including Consensual BiSexual True Story Group Sex Anal Sex Cream Pie Enema Fisting Oral Sex Sex Toys
Last week turned out a lot better than I would have have expected with my girl friend, she had tricked me into going to a swingers club with her, and by the end of the night had been fucked by 4 guys, all dropping their cum in her pussy, more than once too.
But what really surprised me was her wanting to see me being fucked by another guy, and even with her fisting me as the night wore on.
I had set up a douche in her house, and showed her how to use it, and to try it during the week and get used to the feeling of cleaning her anus.
When I phoned her Thursday, she said it felt weird, but also nice, once she had used it a couple of times, I told her to make sure Friday night she was well clean as Lyn was heading out again, and for her to come over.
6.30 pm friday, Lyn was ready, her DD cup boobs hanging free as her dress clung to her body, kissing me as she walked out to meet her boyfriend for more fun, both saying to one another to have a good time.
7 pm Jackie arrived, looking shy, I laughed and said, “I hope your ready, I’m going to rip you a new one tonight”. as my mouth closed in to kiss her hello.
I took my time, building her sexual excitement up, making sure she was well and trully horny before trying any thing new, I slipped my finger in her anus as I was fucking her, and she began to groan louder, that was a good sign, so I turned her over doggy, and slipped my cock back in her pussy, this time, the small thin didlo slipped slowly into her butt as I fucked her.
Jackie jumped as it went in, but soon pushed back, her orgasm’s told me so far so good, as inch by inch I gave her more, her arse now took it all, with the end of the 8 inch dildo against my pubes, my cock sunk deep in her pussy, her orgasm now took hold as she pushed back and forced me to fuck her deeper.
The toys were all laying on the bed, so the next size vibe took the place of the dildo, soon it too was fuly home, and Jackie was going well, my cock wanted to fill her pussy with cum, so I slowed, holding of, and began to concentrate on giving her more anal stimulation.
I pulled my cock out, and grabbed the good 10 inch vibe, with a little bit of spit it began its journey in, she struggled to take the first bit, but once that went in, the rest followed easy, and soon her first anal only orgasm hit her, making her shake wildly and her breathing erratic, she was pushing back hard onto the vibe now too, showing me she was more than comfortable with just anal sex.
I knew she was hooked now, any one who has had a purely anal orgasm like that wants more, so I fucked her butt hard with the vibe, more and more orgasm’s shook her, my cock ready to take over eased nearer to her inviting anus.
I pulled the vibe out, my cock now touching her brown eye, Jackie looked back at me and said “please fuck my arse” that was all I needed, my cock was the fist male flesh to enter this virgin hole.
I hadn’t even got all the way in, and her orgasm hit home, squeezing my cock hard, nearly making me cum, then I pushed all the way in, my balls now slapping her butt, I set about making sure she enjoyed her first cock cum in her arse.
I fucked her steady at first, then as I reailised she was taking me ok, began to pound her harder, her orgasms now running wild, one after another, that was it, my balls just had to let loose, I gripped her waist, my cock plunged fully home, unloaded its first, of hopefully many, sperm seeds into her bowels.
Jackie pushed back hard, her orgasm took control of her body, knowing she was now taking my cum deep in her arse set her of bigger than any orgasm I have given her, it was so nice to feel her gripping my cock in her arse, as her orgasm subsided, my dream had come true, she was now my anal slut too.
I let her rest, then she took to my arse with the toys and fisting me, the night was a blast, I got her to fuck her own butt with the 12 inch vibe, as she sat slowly down onto it her orgasm again told me she was more than happy. When I saw her riding the 12 inch vibe and having orgasms I knew she was a anal convert now, so once more with cock in hand, I bent her over, my cock this time going right in first push as she jumped back forcing me in deeper still.
I use poppers to heighten my anal pleasure’s, so I told Jackie to try it, she trusted me and took a sniff, after awhile she said her head felt light, and her anus felt relaxed, I told her that was what it was meant to do, relax the anal muscles, she took another good sniff and bent forward for me to use her once more.