Exploring anal with cheating gf I met on AFF [MF]

I dont know about you all, but from time to time I shut off the porn and dig into the ol’ spank bank for some hot memory action.  Since I’m just barely on the otherside of divorce, you can imagine there’s been a bit of ‘me’ time.  There are my absolute favorites but every once in a while, I stumble into the memory of a long forgotton encounter.  I decided that I dont want to forget the hottest encounters with the women I’ve been with over the years.  I’ve posted a few stories with throwaways and one other account.  I’d just like to have all of them together from now on.  If you see a repost, there’s your disclaimer. Also everyone in the story is over 18 and names have been changed.

Like many guys growing up in the glorious age of internet porn, I always wanted to experience the feeling of a tight asshole gripping my cock.  I was told by my first few girlfriends that my size made it out of the question. I never considered myself huge by any means but Ive always known I’m above average in length but more notably girth.

My only attempt had been with my ex and despite our best efforts, she couldn’t handle more than the tip before she had enough. It was essentially breakup sex and needs its own story. A few years later, I met Jen on AFF.

Jen was a bartender and ‘single’ mom.  She got a steady boyfriend shortly after we hooked up for the first time but it wasn’t long before we were hooking up again. Jen was thrilled by the risk and naughty feeling of infidelity. She had a slutty past and never hid it from her boyfriend but he was as vanilla as it comes. Jen always held out hope that she could bring her boyfriend into the Lifestyle.

We chatted briefly and within a day or so we were talking about schedules, where and how to meet. She always hosted. She had her own home on the family farm in the valley. The first time we met, we voice verified and she gave me directions to her place with a text that read, “doors open, I’ll be ready”.  I walked up to the door and knocked gently as I pushed it open.

Jen was splayed out on the living room floor on a blanket. Her legs were wide open, a hand squeezing her breast while the other furiously worked a vibrator in and out of her slit.  I wasted no time and was on the floor with her. Can’t remember if I had even shut the door. We said almost nothing. I might have made a comment about being naughty and starting without me.

Jen was definitely more dominant than any other women I’d been with. Rolling around passionately kissing she pulled my clothes off. Her hand massaged my balls and stroked my already rock hard cock.  She sucked me but was eager to fuck. Before I knew it, she guided my bare cock inside her. It wasn’t long before I couldn’t hold back. I warned her but she kept riding saying, “just cum! It’s OK, just cum baby!”

We lied together after basking in that just fucked glow. She said next time she wanted to try anal with me. I was surprised to say the least but I think she picked up on my attitude of “yeah, thats what they all say but can’t follow through.” She promised she meant it and has plenty of experience with her sizeable ex.  We didn’t have time for a second round but made a date the following week

Again, I arrived to an unlocked door with Jen inside, spread eagle on a blanket. She had a strip of condoms and a bottle of lube with her this time. I stripped while she toyed herself before lying down on the floor with her. I took over toying her and licked her clit.  Her legs quivered and she arched her back as she came with a long satisfying moan.

She sat up and pushed me back and began sucking me. God, her mouth was amazing. Everything about her was amazing. I pulled her hair as she bobbed on my cock.  When she was ready, she sat up and tore a condom from its wrapper. I was confused since last time she fucked me raw. She was worried about an oops with anyone other than her boyfriend.  I agreed and she rolled it down my shaft.

Jen loved being on top. This girl could ride… And she did. She rode me so fucking hard she squirted. She pulled me up and we caught our breath, still inside her, straddling each other. After a few moments, she popped off me, pulling the condom off.  She stoked me hard and looked into my eyes and said,

“I want you to fuck my ass.”

Now on her back and all the while, gripping my cock, she lubed me and her asshole. Her legs high on my shoulders, she guided me to her ass.

“Gentle baby.. Slow, slow, slowly…”

She gasped as my head slowly disappears into her asshole. I let her pull and push as she took every inch.

I was finally balls deep. Holding still for a moment to let her acclimate, we kissed intensely. I drew my cock back and slowly began to develop a gentle rhythm. Before long, she was begging me to pound her asshole. Given my unsuccessful history, I was hesitant to go hard. She grabbed my hips and began thrusting me into her giving me a better idea of her limits.

We were dripping in sweat and each other’s juices when she came again. Every muscle in her body tensed up. Her ass squeezed me so tightly I couldnt hold back and flooded it with cum.

A few days later, I’m back at Jen’s. Again, she’d been pregaming while I was in transit. This time she had something different in mind. After she rode me, she took the condom off and again wanted her asshole fucked. I was happy to oblige. But as things heated up, I could feel her reaching back and exploring my ass. It was an entirely new sensation for me. I was comfortable with Jen and had matured sexually to be confident in myself and rolled with it.

I slowed my pace giving her better access. That of course meant being extremely deep in her ass but allowing for a passionate grind as she fingered mine. I could feel her fingers massaging my asshole. She could totally tell I was into it and without a word, she slipped a finger in. That was it.  That sent me steaming over the edge, blasting what felt like a bucket of cum deep into her ass.

We giggled and caressed each other in ecstasy. She asked if that was my first time with anal play.  I said yes.

“Well it won’t be your last, I love anal play!”

True to her word, we had tons of anal play together. Nothing beyond a finger for me but damn was she great it.

Source: reddit.com/r/gonewildstories/comments/az3w8g/exploring_anal_with_cheating_gf_i_met_on_aff_mf