[M]y first anal, from the [f]riendliest stripper ever. | 2016

This all happened about five years ago. It was after my long-time girlfriend left me. We were in a new city, and she didn't have any friends or family there. I can see why she left now. But back then, I still needed to get her off my mind. Other than that, it was a pretty good year for me. My new job was going well. I had lost one hundred pounds at that point in the year. Going from fat to average was a great accomplishment for me. I still felt fat in my head though. Undesired. Lonely. This is a story of the woman who got me over that.

She was sitting in a Starbucks when I first saw her. She had long black hair that went down to the small of her back. Almost ivory skin. I didn't know what color her eyes were, but they were dark. Her face was held up by beautiful, full cheeks. She was wearing a t-shirt and sweatpants, almost like a Saturday morning at home, but at a Starbucks. She sat at a corner table listening to something on her phone and sipping her coffee. She had large tits that stretched out her t-shirt. Looking at her I could tell she was built for more comfort than speed. She wasn't fat, but, plush almost. With a nice ass, that I could tell was big even though she was sitting, supported by strong legs that held everything up in a perfect display Maybe the best way to describe her was…squeezable.

I saw as I passed to make my order that she was watching Archer. I love that show. Almost every line from it is quotable. I went up to the counter and ordered a scone and a coffee. I collected it. When I walked past her I did not notice where I was going. I lost my footing and dropped the coffee and the scone on the ground. She looked down at it and then up at me. I shrugged and said. “Do you want ants? Because that’s how you get ants”. She laughed at that, knowing what I was referring to. We both shared a moment and I cleaned it up and reordered. I went to my own table, looking up at her every once in a while. I didn't think I could get her. But I did.

One of the things I do to get over relationships is going to strip clubs. They used to calm my mind and made me feel somewhat desirable. I know it's all fake and paid for. But it's what did to get over people.

I drove to the local strip club. Got checked in. Scoped out the talent. Everyone was okay. Most were really thin. With the kind of bodies that only possible heroin addicts have. Nothing to grab onto, but, “hey they're naked”, so everyone loves them. That's really not for me. But as I was sitting there was a change in shifts. She walked in and got up on stage. Long black hair. Tits and ass. Perfect skin.

I walked up to the stage and sat down. Put a Twenty on it. She got up close and shoved her tits in my face, looked me dead in the eyes and said, “That's how you get ants.” I was surprised to see her again. It was a chance meeting. I don't know what the odds are of meeting a girl that you met at a Starbucks, dancing in a strip club. They have to be unfavorable. She got down off the stage and gave me a short lap dance in front of everyone. She shoved her tits in my face and rubbed her ass on my obvious erection. She got back up on stage and finished her dances. As she’s was getting off I asked for a private dance, because that seemed fun.

So she led me back to the booths were they gave lap dances (not the VIP). I paid the five buck entry fee. The music started up. I bought four songs for $100. I know that's a lot, but this is my recovery. So she started her dancing, rubbing her plump ass against my boner, shoving her tits in my face, making conversation. She asked me if I had a girlfriend or anything like that.

“No. My girlfriend left a few months back. We moved to the city and she didn't have any friends or any support besides me. She moved back home. We broke up.”

I don't know if the sympathy she gave me was real, but she brushed my hair down, saying, “Poor thing.”

She asked me what my fantasy was. “Never had anal before. That seems like it would be fun..”

She continued on dancing, not shocked at all. She used her ass a little bit more. Sometimes shoving it in my face. No complaints here, it was a lovely ass. She got down on the ground, and slithered up my body, gracefully grazing my cock with her hand as she came up.

“You kinda got a thick cock”

“It’s…okay, I guess.”

Maybe I was too humble. I never thought it was anything special compared to what I watched in porn.

After a lap dance, I gave her a big tip. I left the strip club. I had gotten what I wanted. I felt like it helped me recover something. Now I just needed to find someone I didn’t have to pay to rub against me. I still went to that Starbucks after, and occasionally I would see her. She would see me. We’d smile at each other. What do you say to a person at Starbucks who's had their tits in your face? I don't know.

One day she was there with her computer out, looking a little bit stressed. I sat in the corner with my coffee. She looked up at me and walked over. She asked me if knew anything about taxes. “I'm ok with them.” I said. “I mean I can figure out Turbo Tax.”

She led me back to her table and I helped her out. People tend to think I'm smart because I have glasses and own a Mac, but I'm fairly average, intelligence wise. Her taxes weren’t hard to figure out. I was a little shocked at her asking for help from a complete stranger on something so personal as taxes. After I was done, she thanked and hugged me, pushing up her breasts against my chest, kissed me on the cheek, and offered to buy me dinner as a thank you. I was a little dazed from the feeling of her tits, but I said yes. We agreed on a cajun place we both knew for the next day. I fantasized about fucking her that night, but I never thought I would get the chance.

We went to the cajun place. We talked. I Got to know her a little better. She was 20. Thinking about going to school but not sure of it. I told her not to take out any Student Loans she didn't have to. She agreed. That's why she was a stripper. She told me she’s had a few boyfriends in the past but nothing right now. They all wanted the novelty of dating a stripper, and she wasn’t looking to be the latest accessory to them. She wasn't looking to hook herself out. I respected that. She at least knew what she wanted.

We weren't drunk. She just had water. I was surprised when she asked me back to her place for a night-cap. I usually don't do one-night stands. If that was part of the payment for doing her taxes, I was overpaid. She was persuasive and I said, “Sure. Why not a night cap?”

She had a little apartment. Nothing fancy. One bedroom, bathroom, living room, and kitchen. Nothing to write home about. She got me a drink and then went to change into something more comfortable. I figured I was going to get laid. I just thought it was going to be regular sex, more novel because she was a stripper, and I needed to get over someone. I was still pretty nervous. I hadn’t had sex in three months. Never had sex with a stripper before. I didn't know if she had a disease or anything. I stopped caring about that when she walked out. She had one of those netted, bottomless body suits on. The kind has a hole where the pussy and ass are, and you can see everything through it. I worked my way over to her. I Laughed. Didn't even know what was happening. She took a sturdy wooden chair, put it up against the wall, and sat me down. She started giving me another lap dance, but this one was so much more intimate. She was nibbling on my ear and putting her nipples in my mouth. She did the splits on my lap while and rubbed her pussy against my lap. She gave me a wonderfully white smile. With her back turned she bent over. She shook her ass on my face, then slid it down my body. She reached around and grabbed it, splaying it open wide. She put the tip of her tongue up to the bottom of her nose and gave me a mischievous smile. When I looked down I saw a red, jeweled buttplug.

All the way up her butt hole.

I let out a laugh. I was kind of sweating. I didn't know what to do. She whispered in my ear that she wanted to fulfill my fantasy.

I wasn't going to say no. So she bent over and presented her ass to me. She wanted me to take the buttplug out. I grabbed the cheeks of her ass and, wanting to do something sexy myself, something I would never regularly do, I put my mouth into the crack of her ass, licking the rim where her butthole met the butt plug. She realized that I was doing she gave a little giggle. I slowly worked my teeth into the flared base, and slowly pulled it out of her with my mouth.

She turned around and I could see the lube leaking out of her butt, giving her ass this warm glimmer. She turned around and got on her knees, undid my belt and my pants. Grabbed my hard cock, and just licked it a little bit. On the bottom of the head. Stroking it very lightly. It was the briefest, but best blowjob I've ever received. She only put her mouth over the head once. And then slowly retreated her lips to the very tip of it.

She got up facing me. And then straddled me, putting her legs all the way around me. I ran my hands up her legs and felt her skin. She felt like one of those bicycle seats that you can't help but touch. And it's weird. But it feels like the best thing you've ever felt in your life. They should make beds out of that gel stuff. She felt like that.

She grabbed my cock, facing me. I felt the head be consumed by her butthole. I felt the warm lube run down my shaft. She slowly and expertly lowered herself to the base of my cock. She unwrapped her legs from around me, put her feet on the floor. She, so slowly, went up and down, almost counting to five for every time she went up on my cock, and every time she went down. Her insides felt warm and gushy, and tight, but also soft in a way that’s hard to describe.

My hands wandered around her for the time she was tenderly fucking my cock with her butt. She let me grab her tits and fondle her ass. I finally made my way to her clit and rubbed it. Just as slowly as she was pumping my cock.

“Are you trying to make me cum?” she said.

She put her hand on my chest. “Remeber to breathe.”

I breathe. Exhaling as she went down. Inhaling as she went up. As if she was pumping breath into my lungs through my cock. My hand rested on her groin. The padding of my thumb going over her clit. I tried to make it glide over her clit as slowly as she was my cock. The lights were low, but her skin gave off an almost incandescent glow, her white skin reflecting the light off of everything that she could get it from.

She looked me in the eye and kissed me on the mouth. It was the most enjoyable sex I had had at that point in my life. My breath was going so slow, but I was sweating bullets. Enjoying it as it went on, but wanting to cum to finish it.

After kissing me on the lips. She asked, “Do you want to cum yet?” I couldn't go on for much longer, so I slapped her ass and said “Yeah. Sure. Go for it.”

Almost exhausted from what she had been doing to me, she brought up her right leg, and crossed over, spinning her ass on my cock. With her back turned to me, she started going down with force. A lot quicker and harder than she had been going for the last twenty minutes. She pummeled her ass onto my cock. Pumping. The sound of her ass slapping my lap was one of the best sounds I've ever heard.

I grabbed at her. One hand her tits, and the other one holding her belly. Pulling her onto me, but not really doing any work. Just bracing myself. The last stroke her ass slammed into my lap. I came jets. I breathed. She sat and spun back around, looking at me. My softening cock still on her ass as she kissed my lips and whispered in my ear. “Good boy.”
I ate her out afterward. With lube and cum leaking out of her ass onto my fingers as I grabbed her ass and shoved my face into her pussy. While she stroked my hair and told me how she liked it.

We did stuff like that a few more times. The relationship was mainly based on sex. I think broke up, mainly, because we were both afraid of catching feelings. She didn't want me to self-destruct over her, and I didn't her to mature into anything other than “sexual plaything”. Other than sex, we weren’t really healthy for one another. Butt…its still the best sex story I have.