For those that haven’t read my other stories - I suggest you take a peak. I am a late 20s male from Chicago. I am bi, white, 6’1 with a muscular dad bod and a love of helping people get off.

This is a story about my best anal experience and something I wish I could recreate one of these days.

A year or so ago I met this woman from one of those online dating sites. We hit it off in the first couple messages and she was very sexual right away. I knew after that short talk that we were going to click. We exchanged numbers and got to talking. The topic of sex was quickly brought up and we both understood where this was going. It turns out that she was very very experienced and wanted to use some of that on me. We traded nudes, sexted a bit and then set a date to meet up.

Three days later it was finally time and boy was I excited. We haven’t really talk much since that night and I sent a text to make sure we were still on. She was coming over around 1pm that day and she said she was getting extra prepped. I wasn’t quite sure what that meant but it got me insanely horny. I hopped in the shower around 12:15 and was waiting for the text to get my address. Finally it came and she gave me the “7 minutes away”. My heart was racing. I heard the phone ring and I went to buzz her up. Two minutes later she was knocking at my door.

I let her in and she is just as cute as her photos. About 5’4, shorter hair and a bigger woman. She carries her weight well in her large breasts and plump ass. She was wearing a v cut tshirt and a nice pair of jean shorts. She had a little bead of sweat dripping down her chest as it was crazy humid outside.

We hugged and made some small talk as we walked to the bedroom. My heart still racing, I could feel my cock beginning to grow. When we got to the room I turned around and grabbed her. We kissed deeply and she wasted no time diving her tongue down my throat. I pulled her close and kissed her deeper. I let my hands work down to her plump ass and give it a squeeze as our tongues got to know one another. She tell I was nervous and let me know we can take it slow. She slipped my shirt off and I did the same for her. I unclipped her bra while our mouths were busy and made my way over to her neck as her bra dropped to the floor. I felt her breasts push against me as I kissed up and down her neck. Dragging my tongue lightly down her neck, I pulled back to get a look at her breasts. They hung perfectly off her chest and complimented her curves very well. I sat on the bed and pulled her close. I let my tongue trace between them before slowly working each nipple. Flicking it between my tongue, pulling it into my mouth and giving little playful bites. She let out soft moans and began dropping her shorts and panties. I brought my hand right to her pussy lips and could instantly feel how wet she was.

She pushed me back and yanked my shorts off. She left my boxers on and climb on top of me. She leaned back in to dive her tongue down my throat. Her hips began to thrust, grinding her wet pussy over my boxers onto my hard cock. The head brushing past the clit multiple times. Letting out soft moans into my mouth as she slowly moved, knowing exactly what she was doing and driving me wild.

She started kissing down my chest and finally pulled my boxers off. My hard cock sprung up right away. She smiled at me as she brushed her tits up and down my cock. Feeling it twitch knowing how badly I wanted her to play with it. Finally she dove in and took it to the back of her throat right away. She bobbed quickly up and down on my cock before pulling it out to lick my balls. She twisted the tip with her hand as her tongue explored my balls and the underside of my shaft. She took turns deepnthroating me and running her tongue up and down my shaft. All I could do was lay back and moan. She knew exactly how to work a cock.

She kissed back up my body and let me taste my cock on her lips. I flipped her over on the bed and let her know its my turn. I started making my way down her body. Dragging my tongue lightly down her neck, between her breasts, over her stomach and stopping just above the clit. I hovered over her clit for a second before giving it a light kiss. I continued kissing down her inner thigh lightly working my way down her leg and to her foot where I kissed it and started back up her leg and down the other. I could feel her anticipation and finally decided to let her have my tongue.

I began lightly flicking her clit and her moans grew loud quickly. I ran my tongue over her labia and circled her hole. She was dripping wet, soaking my face. I traced back up to her clit and focused my rythm. Flicking and flicking only to stop to suck on it. I wrapped my arms under her legs and pulled her as close into my mouth as I could. I flicked and nibbled her clit until her moans couldn’t stop and she finally had an organs. Her legs clentched my head tightly, pulling me close. Her breathed labored and she went silent. I pulled back and watched her pussy quiver.

We smiled at each other and I told her to flip over. She didn’t hesitate. I grabbed both ass cheeks in my hands and spread them apart. I wasted no time digging my tongue into her ass. Her moans came roaring back and I could tell she loved it. She reached back and grabbed my head, forcing me deeper into her ass. She tasted like a mix of her cum and sweat and it was wonderful. After a good 5-10 minutes she looked back and told me to fuck her ass. I paused a second and she begged for my cock in her tight hole.

I wasted no time grabbing lube and a condom. She looked at me and said she wanted a little lube on her hole and a lot on my cock. She wanted my cock right away and no fingers first. I didn’t question her and followed directions. She was on all fours as I began to slowly push the head of my cock in her ass. I slowly but surely pushed as her gasped and moaned until I was bottomed out. My thick cock in as deep as it could go. I began to slowly pump and her moans picked back up. She kept telling me how great my cock felt in her ass. I picked up pace and before long my balls were slapping her clit as I pounded her tight ass.

After a bit I pulled out and had her flip over. I pulled her close to the edge of the bed, put a pillow under her and slipped back into her ass. I was watching her eyes roll back in joy as she moans louder and louder. Watching her tits bounce with every thrust. Finally I became fixated on her glistening pussy and the sight kf my cock fucking her ass hard and deep. It turned me on so much that I really couldn’t hold back. I had one last deep stroke and had a strong orgasm, cumming while I was deep in her ass hole. I slowly pulled out and kissed her deeply. She smiled while we kissed and thanked me for the fun.

She cleaned up and we cuddled while we tried to stop sweating. We kissed a little more and she got dressed and left. Still chasing anal as good as that day.