Everyone remembers their first time. I tend to remember all of the first times, and when possible have documented and commemorated them too. The first time I had anal sex I was 22 and dating a 26 year old just coming out of a divorce. I was the first man she’d been with in over 5 years, and she was eager not only to please me but to share new experiences with me. She was at least as sexually open as I was, if not more. We spent a lot of time talking, in person, and on the phone, about our sexual experiences and desires.
The second time we had sex she came over with a bottle of mixed Jameson and Coke. I could smell it on her breath when she walked in the door, wrapping her arms around me. We kissed and she giggled, handing me the bottle. Before I knew it, I too, was mildly drunk. We headed to my room, whiskey in toe, and undressed each other before landing on the bed. She began sucking me off, taking me all the way down her throat and looking me in the eyes while she did it. She slid her mouth off my cock and took my hands, pulling herself to me and kissing me with her tongue, while simultaneously beginning to sit on my wet, hard cock.
"You don’t get to touch right now. Okay?" I nodded, and she interlocked her fingers with mine, riding me side to side, up and down. I watched her riding me while thrusting myself harder and deeper inside her. It was easy, how could I not fuck her harder with her pussy dripping all over my bare cock? She responded, grabbing my hands harder and moving her body closer to mine, rubbing her hard nipples against my chest as she began to pound my cock. Her moans became screams and within minutes she had cum all over my cock. Without hesitation she moved off me and began deepthroating me again. I had never met a woman who loved her taste so much. It was a point of pride, especially for a girl who kid that she had eaten more pussy than I had ever even seen. She probably wasn’t kidding.
I didn’t want to stop fucking her though. She was so tight and wanting. I told her that was enough, she needed to bend over. “Do you want my ass?” It caught me off guard. I knew she loved anal, she’d told me how she liked to finger fuck her own ass when we would masturbate on the phone together, but I had yet to play with it. “Yes, but I… I’m not sure…” She cut me off, smiling and grabbing my hand. “It’s okay. I’m going to show you how to make me cum from my ass.”
She moved up the bed and flipped over onto her back, and spread her legs. “You’re going to start by getting my ass ready for your hard dick. You don’t get to just slip it in with me. Rub my juices down into my ass, and fuck me with your middle finger. Fuck my pussy with your fingers too if you want. Just play with me.”
I began to finger her pussy and take all of the cum inside her and rub it into her ass. It was hard to resist just licking my fingers off though. She had the sweetest, most lovely pussy I had ever tasted. To this day it is her that I have to thank for enjoying pussy so much. Her taste is my standard still, years later, until someone tops it. But I did as she said, and began fingering it into her ass. I was surprised to feel that although her ass was tight, it took my finger with surprising ease. The more of her juices that I used, the easier it went. The louder she got. The faster I fucked her with my finger.
I stopped and looked at her, and reached over to the entertainment stand behind me, grabbing my phone (probably covering it in her cum), and reached back to her. She had a funny look on her face, but it didn’t last long as I slid my index finger into her pussy and gave her the shocker. I was proud. I could feel my cock growing beneath me even though I hadn’t been playing with it, almost as hard as it was when she was squeezing her vagina around it.
This went on for minutes more until I was fucking her pussy and ass in rhythm with my hand, unsure which one was tighter. I came to the conclusion they were equally tight, but equally accepting of my fingers. Was every girl’s ass like this? What had I been missing out on. I snapped out of it though as she grabbed me by my hair and said, “Thick, please… I want your dick now. This is great but I need it inside me.”
I had almost forgot that the point of this second half performance was to fuck her ass, not just finger it. She pushed herself up off the mattress, and flipped over, running a finger from her clit inside her ass. Then she tasted it. FUCK. FUCKING FUCK. I had only seen something like this in porn, and I was now in the middle of it. I had no choice, I had to fuck her ass hard. I grabbed my already nearly rock hard dick in my right hand, took her left hip in my other and pulled myself into her.
"Ahhhhh. Mmmm. Goddddd." I was inside her and she was in ecstasy. I grabbed both of her sides and began to pound her. "You fucking love it, don’t you? How’s it feel to get your ass pounded? You want it harder?" Her hands grabbed at the sheets with such intensity as she just screamed. It was primal, but undeniably feminine. I continued, until she said she wanted to watch me. I pulled out of her, rubbing her pussy with my cock before she flipped over again. I could see her outline in sweat on the bed as I wiped my brow and took a deep breath. Grabbing my cock and rubbing her clit again, I slid my tongue out and licked her stomach before sliding willfully easy back insid her warm, snug asshole. She bit her lip as she rubbed her clit more and more, her ass now in both of my hands as I brought her to my pelvis and back out again. With each alternating thrust my eyes shifted from her beautiful thin face overcome with raw lust, back to her asshole, full of my massive, rigid cock, covered with her sticky cum which was EVERYWHERE.
Our breathing began to sync and the rhythm overtook everything. It was like a tribe of Africans were drumming for us as we fucked deeper and faster. Up until that moment I hadn’t even thought of it: this was for me, this was mine. Her ass was mine now. She had already cum minutes in and this was for me. “Rub your clit, faster. You’re going to cum for me.” She looked down and began to watch me inside her ass more intently as she furiously rubbed her swollen clit with two fingers. I fucked her ass even deeper as she began to arch her back and then it came. In one wave I filled her ass with cum, in the next wave it began to drip out. A third wave came and my cum was all over my balls, dripping everywhere. “FUCK. YOU ANIMAL!!!”
"Give it back to me, there’s so much of it." She rose off her back and began to suck my cock as I arched my back and took the moment in. It was the biggest mess I’d ever made. She sucked and sucked, and it occurred to me I should taste it too. I slid my middle finger inside her ass and was amazed at how full of cum she still was. Mine, but definitely her own too. I sucked my finger off and she smiled, watching me taste her ass and pussy, as well as my own seed.
I collapsed back on the bed, an unescapable laugh that I wasn’t even sure was my own. Looking at her she said, “That was great. You can smell our sweat in the air right now, mixed together. And in a minute we’ll do my second favorite part of ass sex. The shower together.”
Ed. Note: That is indeed from the act, not a photo I found.