My [f]irst time with a younger man | 2016

***Sorry it’s cheesy to refer to us as “Cougar” and “Cub” but I wanted to protect anonymity and I’m not very creative

***This was 3 years ago and I’ve fantasized about it thousands of times. It’s as true as I remember but I edited out any awkwardness that might make it seem less hot

I live in a major metropolitan area that has a local website, kind of like Craigslist, that I use all the time to find various degrees of companionship. Normally I’m trying to meet guys to date, but tonight I was looking to get fucked.

There was an ad that caught my eye: “22 year old man, seeking experienced woman to take my virginity”. I just turned 35 and I’ve never been attracted to younger guys, but I was horny and ready to get my cougar on. I don’t know if I believed or cared if he was really a virgin. I’ll spare the lengthy details, but we emailed back and forth and exchanged pictures. Even in clothes I could tell that he was his natural physique was solid. I’m 5’3” and about 160, and he was 6’ tall and thick from his pictures, and it turned me on to think about being able to dominate this really big guy.

He asked me to meet him for coffee at a coffee shop near my house. I chuckled to myself and suggested that he come over to my place for a glass of wine. I wish I could say that I put on some sexy dominatrix lingerie and answered the door holding a whip, but this is new territory for me too so I wore a black thong, black yoga shorts, and a loose cotton tee shirt that hung off one shoulder making it pretty obvious I wasn’t wearing a bra.

He rang my doorbell at 7:30 PM. I opened the door and drank him in. He said “Hi!” and his voice cracked, so he cleared his throat and said “hi” again much deeper. He seemed taller than 6 feet, but maybe because I was barefoot. He stood at my door smiling and held out his right hand, to shake mine. I ignored his extended hand and stepped into his arms, rising on my tiptoes to touch my lips to his softly. He didn’t move. I put my hands on either side of his face and licked his lips, then stepped back to let him in. I just now noticed he was holding a plastic grocery bag.

“Welcome,” I said. “Let’s go into the living room.”

“O..okay,” he stuttered just like I imagined he would.

“What’s in the bag?” He seemed like he wanted to answer me but couldn’t find the words, so he just passed me the bag. I peeked inside and had to control my laughter. There were a dozen different kinds of condoms, 3 kinds of lube and spermicide. I was about to fuck a boy scout. I threw the bag on the couch and grabbed the front of his shirt in both my fists and pulled him to me for real this time. I attacked his mouth. He matched my enthusiasm and after a few clashes of teeth, we developed a rhythm and he was really getting me hot. He still had his hands at his side while he eagerly plunged his tongue in and out of my mouth. I unclenched my fists from his shirt and grabbed his hands, slowly moving them to my breasts. He squeezed my breasts and I swear in my head I heard him say “honka honka!”, so I kept my hands over his and encouraged his fingers to massage slower and play with my nipples. After about thirty seconds he squeezes hard and stops kissing me, pushing his forehead firmly against mine and groaning. He came in his pants.

I hoped he wouldn’t realize I could tell, so I pulled away and said “I’ll go get us some drinks. Make yourself at home! The bathroom is through there if you need it.”

When I finally walked back to the living room balancing our drinks he was standing next to the couch. “You can sit down, you know”.

“Oh, oh yes. Oh. Yes.”

I gave him a glass of wine. We talked and finished the bottle of wine. Well, I finished the bottle of wine. He had most of that first glass I poured him, but it seemed to do the trick. He was loosening up, and seemed much less nervous. I asked him if he’d ever seen a naked woman.

“Not in person, but I watch a ton of porn.” As soon as the words were out of his mouth he looked like he wished he could take them back.

“Do you want to go to my bedroom where we can get a little more comfortable?” I asked.

“I want to taste you all over” he said back at me, staring me deep in the eyes. I was speechless. I nodded and took his hand and led him to my bedroom and we stood at the foot of the bed kissing for a while. I was running my hands all over his back and grabbing his ass, grinding against him. He steps back, pulls off my shirt and stares at my boobs with his mouth wide open for what seemed like a full minute. He pulls down my shorts so I’m standing there in nothing but a thong with my shorts still around my ankles. He brushes his hands over my pussy, barely even touching me where I needed him to. He moved around and grabbed my ass. Squeezing. He pulls down my thong and stares wide eyed at my shaved pussy. I walked backwards and laid down on the bed. He stared for another minute, then came and awkwardly laid half on top of me to kiss me again. I moved my hands to his waist and untucked his shirt from his pants, and put my hands underneath. His skin was warm, but he pulled back before I could get his shirt off. He stared at my tits for a second licking his lips like he was an animal stalking his next meal, and then he attacked. He sucked and licked both my tits like a fucking expert. He must have suckled me for about 15 minutes, making me cum once and he hadn’t even touched my pussy. He took a break from my breasts and laid beside me, kissing me again. I moved my hand to the front of his pants and felt a very impressive erection. I grabbed him through the thick material and rubbed. He came right then. There was nothing he could do to hide it.

“That’s okay” I comforted, but he didn’t seem embarrassed this time. He took a beat to recover from his second orgasm of the night, and then sat back on his heels to gaze at my pussy. He pushed my legs apart and ran his middle finger up and down my crease, not going any further than that for about 2 minutes. I was going insane. I was sopping wet and he was barely giving me anything. I was getting hotter by the second. He stopped and I opened my eyes. He took his middle finger and put it in his mouth, suck all of my juices off it it. “mmmmmm, I want more of that”, he said. I smiled and bent my knees, spreading my pussy wide for him. He didn’t need more of an invitation than that. He moved down and put his face right into my pussy, so close that I could feel his breath, and then gave me a kiss. The second his lips touch my clit I came. My legs jerked up and wrapped lightly around his neck pressing his mouth to me for a second. I looked down at him and he smiled confidently. He used his hands to part me began to gently but firmly lick my clit. Pausing to suck me into his mouth at times, using his fingers on me as well, but only externally. Up to this point, I’ve cum twice as has he, and he hasn’t penetrated me at all. He lapped me up and I came a third time before he finally plunged a finger deep inside me. He put in a second and turned his fingers upside down pushing up right into my g spot. Cub has been watching the right porn. He sucked my clit while he massaged my g spot for 20 minutes making me come twice more. My body hummed with satisfaction, but I also longed to have his cock deep inside me, and I told him so. I pushed him back and started to undress him. I don’t know if it was the hour of unimaginable pleasure he had just given me, the wine, or the truth, but in that moment I swear to you he had the most beautiful body I’ve ever seen in my life. His cock was about 8 inches and full hard. I dipped down and gave the tip a quick kiss.

“Soon I’m going to suck your cock dry and swallow every drop of your cum, but right now I need you to fuck me”. I don’t normally talk like that but I was so turned on and wanted him to know I fully intended to return the favor after I got fucked. He nodded and grabbed his bag. I helped him choose a condom and roll it down his dick. I pushed him onto his back and straddled him. I reached down and put the tip of his cock right at the entrance of my pussy. “This is it” I said, smiling down at him. He smiled back and I sank down on him, taking him in one fluid motion. His head came up off the bed and I could feel him jerking. I knew he was close to cumming. “Breathe deeply” I said, not moving. He relaxed, laid back on the bed, and put his hands on my hips. I bent over and kissed him. I could taste myself on his lips and it made me so hot. I sucked and lapped at his lips for a minute, until he pushed on my hips and set the pace for our fucking. I swiveled my hips until his cock hit my sweet spot and I screamed. The second I screamed out he came, shouting out and completely drowning out my scream. He yelled “OH FUCK!” and dug his hands into my hips. After a minute he moved his hands up and grabbed my face firmly between his hands and kissed me hard. We went through almost all of the condoms he brought, and by the end of our “date” I lost count of how many more times I came. I still don’t know if the virgin act was for real or role playing (the two times he came in his pants make me think he could be a virgin) but regardless, I thought I was going to be the dominant one; the one in charge, and I’ve never been so glad to be wrong in my life.