Fairness in everything has always mattered to me very much, so when my GF let me use her ass as I pleased, I felt it was only fair that I fulfilled her pegging desires and let her use my ass as well, but we’ll get to that, first let’s start with her…
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My 28M GF /u/upnovagal1111 (28F) has an incredible mind, body and soul. She’s a truly beautiful compact succubus at 5’4” with rich 32D tits and a delicious plump ass. Even better still, her ability to cum from solely nipple, clitoral, vaginal or anal stimulation consistently amazes me. She is by far the most sexually open and adventurous person I’ve ever met, and I love her in every way imaginable.
When I discovered she was interested in anal, I was extremely intrigued. With previous women in the past I felt like anal was something they did just because they knew men liked it, not because it was something they truly enjoyed. But with /u/upnovagal1111 things are very different, she truly *loves* anal and can orgasm consistently from anal penetration alone – something I’ve never experienced before.
We quickly tried anal late one night, but rushed into it and the lack of preparation led to some discomfort for her, so we abandoned things with the promise of trying again soon.
About a week later on a Sunday evening one thing led to another and while fucking in prone bone, she said “do you want to try it in my ass again?”. Of course no gentleman could refuse such a request, so I lubed up a small plug and slipped it in while she was face down on the bed. Seeing the widest part of the plug stretch her ass is always a beautiful sight, but she was comfortable with it and was far more relaxed than before.
After handing her my magic wand vibrator which she placed on her clit, I fucked her pussy in prone bone for a while. The extra sensation of the butt plug was clearly working for her, as she came beautifully on my cock soon after. The extra pressure of her plugged ass combined with her pussy gripping my cock as she orgasmed felt truly divine for me. After another orgasm I knew she was ready to try my cock in her ass once again. I gently removed the plug and liberally soaked my cock in silicone lube before pouring some over her asshole, rubbing it in with my thumb. “Are you ready?” I said, a muffled voice from the pillow said “yes, do it”.
I held my cock tightly and slowly pushed my way into her ass, feeling resistance at first but then a soft release as her ass gave way and let my cock inside. She was so hot and tight, it felt wonderful. After an inch or so I paused and waited for her to relax and get used to the sensation. A few moments later she said “fuck me” and I started moving, gently at first, leaning over to kiss the back of her neck as I slowly opened up her ass. The sensation of warmth and the wonderful grip of her asshole was a beautiful feeling.
Not long later I was fucking her well lubed ass hard, pushing her down into the pillow while she pressed the magic wand vibrator against her clit the entire time. She orgasmed a few times like this, but unlike her “normal” orgasms from vaginal sex, I could tell she was not fully in control when she came from anal. Her anal orgasms were deep and powerful, with full body spasms and her losing all ability to function – it was incredibly hot to watch her lose control like that.
After her third or fourth orgasm she lifted her head from the pillow and asked (almost begged) “are you going to fill my ass up?” which of course I simply could not refuse. After she said that it didn’t take long for me to get close, I whispered into her ear “you’re going to get it baby, a hot load pumped into your ass” which caused her to moan wonderfully. A few strokes later I pressed her back hard into the pillow and started to cum. Clearly she could feel my cock pulsing as she instantly started to cum as well, but this time her orgasm was like nothing I’ve ever experienced. As I pumped my load deep into her ass she had the hardest orgasm of her life, her moans and facial expressions like nothing I’ve ever heard or seen – she completely lost control of her body. Her asshole spasmed and gripped my cock while I kept pumping cum deep inside her – her brain completely reset, her entire body shaking as I gave her every drop I had.
After her massive orgasm I laid there on top of her in prone bone for some time, both of us trying to understand what just happened. I wouldn’t find out until later that I had just experienced the biggest orgasm of her life. I pulled out and saw my cum dripping from her ass (a beautiful sight) before kissing her deeply and holding her tight for the rest of the night.
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A few days later, /u/upnovagal1111 and I were discussing our sexual fantasies in bed. During our conversation she hesitated, like she wanted to say something to me, but couldn’t quite find the words to say it. She looked embarrassed, so I assured her that any fantasy she had involving me would be tried at least once, no questions asked. I know she would do the same for me, so it was only fair.
It took a few moments but eventually she told me about her pegging kink and how much she fantasized about pegging a guy… I guessed that meant me! While I honestly hadn’t put pegging anywhere near the top of my list of fantasies, I want to fulfill all her dreams so agreed to let her do it to me whenever she wanted to. She is so generous with her ass, it would not be fair if I wasn’t generous with mine too. Besides, I knew about the male prostate and the potential for incredible hands-free orgasms, so I was intrigued to see how it felt as well. I remembered her incredible anal orgasm a few days earlier and, well, I was jealous and wanted my own one too.
About a week after that conversation she came over to my place with some new toys: a strap-on harness and a small dildo. The dildo was smaller than my cock, but knowing that it was going in my ass made it strangely intimidating, despite its diminutive size. However, I knew my caring GF would look after me well, so we got started and she put the strap-on harness on and got everything ready. We decided the best way to start was with me fucking her while wearing a butt plug. She lubed a small plug up, handed it to me and let me slip it in which happened quite easily. The feeling of fucking her pussy with a plug in my ass was really great, I’d strongly recommend this to any man out there – it’s wonderful fun. After a few minutes of me being in control and using her pussy, she told me to take the plug out and lie down on the bed, it was her time to be in charge.
As a straight man who never had anyone touch his asshole before, having my GF lay me down on the bed, hold my legs up and lube up my ass was a totally bizarre feeling. Seeing my gorgeous GF over the top of me in missionary with a dildo between her legs was so odd, yet strangely hot. I loved how she looked – so powerful and in control of me, she was more beautiful and stronger than ever before right then. I felt quite vulnerable and nervous, but strangely excited to experience this at the same time. After 28 years of being the one doing the fucking, it was my turn to get fucked for the first time. I could tell from the look in her eyes that she was incredibly excited, this was something she’d dreamt about for a long time.
She lined the well-lubed dildo up with my asshole and pressed her way in. The sensation was very odd at first, really not good or bad, just weird. After a few seconds of relaxing, she started gently fucking me which started to feel good. The feeling of being stretched out was nice, and looking at my GF’s beautiful face and tits while she fucked me was incredibly hot. There was a point where the tip of the dildo started rubbing against my prostate which felt really amazing, at that point I suddenly knew what all this was about and why so many men enjoyed it so much. Touching the prostate made my cock rock hard, I could definitely cum if she kept doing that. I looked up and saw that she was about to cum herself – incredible given that I was not touching her and the strap on harness was only very lightly pressing on her clit. She was so mentally turned on, I’d never seen anything quite like it.
She flipped me over into prone bone and started to take my ass from behind – this definitely felt more intense for me and I found myself moaning softly into the pillow as she fucked me. The dildo was definitely hitting the right spots here although I found it quite intense. My entire face and jaw started to feel numb as she pushed me into the pillow and kissed the back of my neck as she fucked me – she was really getting into it. She asked whether I wanted to try going on top, and I said “why not” so we flipped over. I climbed on top of her “cowboy” (?) style and I slipped the strap-on in. This position really hit a nice spot and everything started to feel amazing soon after. I jacked off my cock with one hand while massaging her breast with the other, all while slowly riding her cock. This was getting too much for me and I told her I was going to cum to which she greedily encouraged. I sped up the pace, the dildo rubbing against my prostate until I couldn’t hold it any longer and busted a huge load straight onto her chest and tits, the dildo still inside me as I came. I would have liked to have pulled out and came on her beautiful face, but it felt too good inside to pull out like that :)
Afterwards we cleaned each other up and cuddled on the bed together, her aftercare was the best as you can imagine. She told me how well I did and how proud she was of me, it felt wonderful and I couldn’t wait to do it again (spoiler: we did it again about 2 weeks later!).
Source: reddit.com/r/gonewildstories/comments/xy6bum/my_gf_had_the_strongest_anal_orgasm_of_her_life
Welcome to a new world of pleasure!