First Anal [FM] From the Cougar Chronicles

Sorry if this is long, first time sharing something like this.

My friends tend to wonder why I date younger guys. You would think me being the older one, I would have more adventures under my belt. Truth is, I was a very late bloomer (we just won’t go into that). But I’m not sure that is the reason for dating younger guys. That may never be answered. But one experience with a younger guy stands out (ok there may be more than one). My introduction to anal came from a younger guy. I was 38 and he was 25. I met K through a dating site. He was the gym rat type, between work and school (he wanted to be an EMT), all his free time was spent in a gym. So, I was surprised he took an interest in me. Even though I go to the gym, I am definitely not the gym body type. I go to the gym so I can survive a disaster movie and eat Nutella. Turned out we did have a great love of movies in common. I would say after a couple weeks of texting, our texts became more and more less PG. There are probably some fun photos of me circulating out there somewhere, if I find out they are making money, I need my cut.  So, one text leads to another, a couple of phone calls too. I even got lectured for leaving plastic water bottles in my car and still drinking from the bottle.

 I would say after a few months, the time had come to either meet up or just drift away. I am not very comfortable with instant hook ups, I need to know something about the person, feel a small sexual spark you know. Otherwise, I would be the most awkward person you ever met for a hook up.  I want to be comfortable and enjoy everything. So, I took a chance decided to hang out with him. I met at his place (I did send one of my best friends the address to come look for me if I go missing since they didn’t live to far from him). We sat on his couch, I had a glass of Moscato, and he had a beer. I think we were both a little nervous. We were watching a movie, to this day, I cannot remember what movie it was. He asked if he could kiss me. I said yes. That’s all it took was one hot kiss and the squeeze of my tits and I was good to go from that kiss. It was a good kiss after all. We continued to make out, his hand up my shirt cupping a breast. He begins to play with my nipple between his finger and thumb. Add a little pressure then release, just enough to drive me insane and wet. He then lifted my shirt over my head. So, there I am, shirt off, my breast about to be exposed. Feeling a little self-conscious.  But surprisingly he continues to kiss me and work my bra off. His mouth finds his way down to my nipples. His tongue teases my erect nipples, he lightly bites at them. By this time, I’m pretty sure my panties are soaked. He begins to undo my pants and unzips them. He kisses me hard and I feel his hand slide down my pants into my panties. I feel his fingers rubbing me. He whispers in my ear “someone is enjoying this”. I moan as he starts to rub my clit. He then slides two fingers in my pussy. The kisses are intense as he finger fucks me. He asks me if I ready to try something. I nod yes, he has me feeling so good and relaxed, I would do anything he wanted. I feel one of his fingers poke around my ass. He whispers for me to relax as he gently slides his finger in my ass. I was so surprised about how much I loved it. Before I knew it, I had a finger in my ass and another in my pussy working in and out. He worked faster and faster, I came so hard all over his fingers. I never felt anything like that before. He stood up and grabbed my hand and lead me to his bedroom. He pushed me down on his bed and told me he wasn’t finished. He took my pants and panties off, got on his knees in front of me spread my legs. I felt his mouth kissing up my thigh. His lips made it to my now dripping wet pussy. His tongue began to probe and tease me. His tongue found its way to my clit. I gasped from the pleasure. He rolled his tongue around my clit and sucked. I almost instantly exploded in his mouth. Why did I wait so long to meet him! The way he ate my pussy made me mad at myself for not doing this sooner. I was losing control. I moaned louder and felt my whole body tighten up before a wave of extreme pleasure went through my body. He came up to kiss me and tasted myself all over his lips. I reached down and felt his hard cock trying to escape his jeans. I struggled to unbutton his pants, he had to help. He pulled his pants and boxers down. His beautiful hard cock waiting for me. I got down on my knees as he stood over me. I slowly started stroking his cock. I put his cock to my lips and teased the head with my tongue. I wrapped my lips around his hard cock. Looking up at him, I can tell he was enjoying this. I started sucking his cock. Working his cock down my throat, I heard him moaning and I got off on it. I took all his cock down my throat and held it. I released his cock from my throat. Wrapped my lips tight around the head and looked up at him. I teased the head of his cock with my tongue. Then worked my tongue down to his balls. I licked and sucked on his balls while I stroked his cock. My mouth made its way back to his cock. I could tell from his moans that he liked the way I sucked his cock. It got to the point he couldn’t take it anymore and pulled me up. He said, “I want to fuck you so bad” He laid me on his bed, grabbed a condom, positioned himself between my legs and slowly slid his cock in. He groaned as he slid in, “God, you are so tight”, the way he fucked me felt so amazing. He worked the pace up and fucked me till he came. 

We had to rest for a bit, and I threw on my shirt and panties. I was thirsty after that, so I went to the kitchen to get some water. He followed me and stood behind me and started kissing on my neck. He pulled me closer to his body and held me tight. I felt his hard cock on my backside. He put his arms around me, and he began to cup and squeeze my breast. From our texting, he knew what made me wet. He was ready for another round. He guided me to his kitchen table and bent me over the table. He pulled my panties off and started rubbing my ass. He began to spank my ass, a little harder each time. A spank then a rub. I could feel that my ass was red and hot. Each slap made me gasp and moan. I was getting wet from being spanked and he knew it. He leaned in and whispered in my ear, “I’m going to fuck you so hard”. I heard the wrapper of the second condom being ripped open. He slid his cock in my wet pussy. Each thrust grew harder. His hand on my back holding me down on his table. His table rocked with each thrust. It felt like walking after this was going to be a difficult task. 

After round two, I was sure were done. We were back on the couch watching TV, just relaxing. I was thinking to myself, “it’s getting late, I wonder if he wants me to leave?” I was wrong. He started kissing me again. We made our way back to the bedroom. This time he had me get on the bed face down and ass up. He then put his hands on my ass and spread my cheeks. His tongue began to work the rim of my asshole. This felt so amazing! I felt his fingers slide into my pussy getting me so wet. His fingers became soaked from my pussy. He took one wet finger and gently pushed into my ass. Working it in and out to loosen me up for another finger. He had two fingers in my ass, and I was loving it. He asked if I was ok and I nodded yes. He increased the pace of his fingers. He leaned over to the side of his bed for something. It was a little bottle of lube. He applied some and stroked his cock. I remained in the position. I felt the head of his cock slowly penetrate my ass. I tried to relax, it hurt the more I tensed up, once he got his cock halfway in, I was able to relax a little more. He then worked all his cock in my ass and slowly began to pump. At first, I was nervous and all in my head about this, once I let go, it felt really good. I don’t think I can put into words how good anal can feel once you relax and let go. His pace got a little faster, not much faster. He started grunting and moaning with each thrust. Before I knew it, I felt his hot cum explode in my ass. This sent me over the edge. He gently pulled out his cock. He got up and got a towel for both of us. He laid down beside me and held me for a bit.  I realized it was so late and said I better go home since he had to get up go to work. He told me I could stay but if I did, he was going to fuck me all me all night. I wasn’t sure if I could take anymore, my body was exhausted. It was so tempting to stay. Looking back now and thinking about how great that night was, I should have stayed. We did hang out a few more times but eventually drifted apart. I think about him every now and then. So glad my first anal turned out to be an amazing experience, otherwise I’m sure I would have been turned off it forever.  

Source: reddit.com/r/gonewildstories/comments/egkf9y/first_anal_fm_from_the_cougar_chronicles