This is a true story about my ex-girlfriend, who I call on here Anya. I was very sexually inexperienced when I first started dating Anya. She really helped me [learn what turned me on](https://www.reddit.com/r/gonewildstories/comments/nd1ewb/fucking_my_exgirlfriend_at_the_beach_house_while/), and [pushed my boundaries](https://www.reddit.com/r/gonewildstories/comments/ncsvb0/accidental_anal_with_my_exgirlfriend/). Ultimately the relationship was pretty [unhealthy](https://www.reddit.com/r/gonewildstories/comments/nde7np/i_tried_to_break_up_but_my_exgirlfriend_took_off/), but I always like looking back at our sexier times…
As always, I love it when readers comment! You can also send me a message or a chat if you really like the story and want to talk.
When Anya and I first started dating, I’d only had sex once. Anya was much more experienced, but she took her time with me, slowly introducing me to new things.
A few months into our relationship, Anya started asking me these odd questions. We’d be in the car, and she’d suddenly ask, “Is there anything new you want to try in bed?”
I’d turn beet red and my mind would go blank. “Uh… I don’t know. What about you?”
“Oh, I’m just wondering about you,” she’d say, giving me a coy smile.
My mind would start racing. What could Anya mean? She’d already taught me to fuck her mouth, which I found wild. She’d lay down on the bed and I’d straddle her face. I’d fuck her mouth while she fingered herself. She’d always climax like this, sucking hard on my cock and moaning.
But I had an idea of what Anya was hinting at. You see, when we were fucking, Anya really went crazy when I pulled her ass cheeks apart. If she was riding me, I’d grab her ass, spread her cheeks, and then start thrusting hard into her. She went wild, jamming her pussy against me and climaxing.
The next time Anya asked me if there was anything new I wanted to try, I said, “Well, I have been curious about… anal sex…”
Anya gave me a big, wicked grin. “I thought so!” she said. “I’ve really been fantasizing about it.”
“I’ve never done it before,” I admitted.
Anya winked. “I’ll teach you.”
I was really excited for the next night I spent with Anya. In her room, we made out, stripped, and started teasing each other. Anya was incredible at sucking cock, she was able to get me hard in no time. She then got onto all four on the bed. I got behind her. There was her ass and her asshole.
Anya told me to get my cock really wet. I spit on my hand and rubbed it all over the head of my cock. I kept staring at Anya’s asshole. “Are you ready for this?” I asked her.
I could tell Anya was very turned on. Her pussy lips were swollen and read. Still on all fours, she said, “Yes, I want to feel you in my ass.” Anya licked her hand and then spread saliva over her asshole.
I put the head of my cock against her asshole and started to push. It was so tight! I was used to sliding right into Anya’s wet pussy, but this was very different.
Anya started whispering, “Yes, yes, yes!”
I pushed harder, and suddenly the head of my cock pushed into her asshole. I started sliding just the head of my cock forward and back, a bare inch each way, getting a feel for it. Anya moaned. “Deeper,” she said.
I pushed further. This felt very different from fucking Anya’s pussy. I felt a tight pressure all over my dick. The taboo nature of this was really turning me on. I continued to fuck Anya’s asshole, going slow, gently pulling back and then thrusting in again. Slowly, slowly, I shoved more of my dick inside.
Meanwhile, Anya was groaning and grunting, gripping the bedsheets in clenched fists. I could tell this was giving her a mix of pleasure and pain.
I reached down and started rubbing Anya’s pussy. It was soaking wet! I slipped my fingers between her pussy lips and found her clit, started rubbing it wildly. Anya started bucking back against me, driving her ass cheeks against my crotch, getting me even deeper in her asshole.
I slid two fingers into Anya’s pussy and began fingering her. With my fingers in her pussy and my cock in her ass, I was so turned on I couldn’t hold back. “I’m going to cum,” I told Anya. She nodded, her eyes still closed tight, breathing hard. “Do you want me to cum in your ass?” I asked her. She nodded again. “Does it turn you on when I’m fucking your ass?” I kept fingering her. She moaned, beyond words. It was too much for me.
I felt my balls tightening and that wonderful feeling took over. I thrusted deep into Anya’s asshole, my cum just exploding into her.
When I pulled out, I could see some white cum dripping from Anya’s asshole. It was sexy as hell.
From then on, assplay became a big part of our sex lives. Anya loved it when I fucked her ass in the shower (and I liked it too because I could clean right up), and I could easily turn her on just by mentioning anal sex. She also liked it when I would pull out of her pussy and cum into her asshole.
Just thinking about all this is turning me on!
Oh Anya, I really wish our relationship had been healthier, because the sex was always amazing.
Source: reddit.com/r/gonewildstories/comments/nzqttc/after_weeks_of_teasing_my_exgirlffriend_finally
Arya from gears of war.