I moved to my current state as a young man/boy (23-24). I had had some fun sexual experiences before in my home town, but they were few and mild compared to what I started after I moved. New state fresh start so to speak. I wanted sex. I did not want a relationship, I did not want anyone to have any expectations, I just wanted sex. It was the start of an extreme ho phase, what can I say…
I joined a site called Fling. This was right before the explosion of the iPhone and apps etc, so Fling was the easiest way I could find to get what I wanted. At first, of course it was difficult to find a match, as I imagine it is for a lot of men on dating sites/apps. But after a while I hit my stride… A girl around my age going into the Navy, one a few years older that was looking for adventure, another that just wanted to fuck.. and then I met her. All these years later, I don’t remember her actual name, so I’ll call her Leann.
Leann was an older woman, I would estimate in her late thirties, maybe very early 40s. She wasn’t a crazy bombshell but she was attractive. She had a thicker body, wide hips and she had extremely large breasts.. although I don’t remember her real name, I remember her profile id had the words “40f” in it, which back then I assumed was her breast size (I’m only just now realizing it might have meant “40 female” as it does here in Reddit, but her tits were very big so I went with that).
I started to talk to Leann and learned all about her. She was married and had 3 kids, one of which I remember was just starting high school, she had been married since she got out of high school, and she was an extremely sexual/sensual giving person, and she was bored with her sex life. Also.. she was a submissive. I was just getting more into the sexual aspect of my life, so I didn’t really understand the dynamics of a Dom/sub relationship so she explained it all to me. She liked to be told what to do, when to do it, she liked to be used. It sounded new and hot, so of course why not?
We talked for a week or so before I tried setting something up for us to meet. But everytime I asked, she was unavailable. She had errands to run, kids to take care of, going out with husband, etc etc. Typical adult responsibilities. Of course, I was still a young boy with no responsibilities of my own besides work, so while I couldn’t relate, I understood. But after trying to set something up for a good couple weeks with no results, I was admittedly getting impatient. Eventually, I remembered: She’s a sub. So… I changed tactics.
The night of, I remember being nervous as I had zero experience with this sort of thing, but I messaged her on Fling and asked if she was free that night to meet. Surprise surprise she was not, she had whatever to do with her husband. I gathered my nerves and straight up told, not asked but TOLD her that she was going to get whatever she needed done done, and that she was going to meet up with me tonight, I was not asking. I fully expected it to blow up in my face.. But to my surprise she sent back “Ok”. Ok?? Holy shit, did that just work? So I continued. I told her to give me the address of somewhere near her place we could meet up. She gave me some restaurant parking lot and I told her the time that I expected her to be there. Is this really working?
That night I left to the restaurant, it was maybe a twenty minute drive away I got there around 8 or so. I pulled into the parking lot pretty much right on time and texted her I was here. No response. I waited a bit, then sent another text telling her where I was. No response. After about 15 minutes hearing nothing I figured I got played. But sure enough, right as I was thinking I should probably leave, I get a message that she’s going to be pulling up soon. Oh boy here we go.
She tells me what car she’s in and I pull up next to her. I get out of my car and she walks over to me and I was… Well, I was pleasantly surprised. She looked even better in person than on her page. It was like a reverse catfish. She was wearing a low cut v-neck that allowed ample cleavage to be shown and hugged her body, tight jeans, and a pretty smile plastered on her face. I could tell she was probably just as nervous as I was. I had been psyching myself up the whole drive over to be this “dominant” person, something I had never been up to this point, so I told myself I just had to go for it full on. We hug, exchange pleasantries and small talk for a few minutes until I tell her to get in my car. Inside, I have her tell me where the nearest hotel was (literally right across the street) and we head over.
I get the room and we head upstairs, us touching each other here and there and me going over how I’m going to do this, and honestly kind of freaking out. I don’t remember if she was my first older woman, but she was definitely one of the first few, and add on this dominant/submissive thing? Yeah I was nervous as hell. But we went inside the room, and I basically told my nerves to steel up.
Inside the room, Leann sets her purse down and sits on the couch. I looked at the room for a second and made my way over to her. She sat there with her hands on her lap looking so cute and innocent.. I didn’t say anything as I stood in front of her, I just leaned over and put my lips on hers and she reciprocated. It was as though that one kiss just freed me from all my doubts and concerns and anxiety, I was in it now, and I got bold.
I pulled away from her and told her to take my cock out. She did as she was told. I was already hard and Leann just stroked me for a while. She looked up at me but saying anything for a bit and.. Oh yeah!! She likes to be told what to do. I told her I wanted her to put her mouth on it. She sat there, taking my whole cock in her mouth, pushing it to the back of her throat. My hands were on her head, grabbing her hair, slowly thrusting my hips back and forth into her mouth. I could tell when she started to get really into it, she let out little moans here and there, she started to pick up the pace, I could see spit dribbling down her chin onto her chest (which go figure, would become a huge turn on for me in life).
After a while of sucking, I stopped her and pulled her up off the couch and towards the bed. I told her to take off her clothes, and I took mine off as she did. By the time I was naked, I just had to pull her jeans off her feet. Her tits were incredible.. Just huge but also had a good bit of firmness, not saggy like I expected them to be. The thing that got me were her legs though.. they were silky smooth and fit, her calves were extremely sexy. Maybe she was a soccer player or a swimmer or power lifter in the past.. they were incredible.
I put a condom on and got on top of her and started to kiss her. She was a woman of extreme passion and lust. The way she wrapped her lips around mine and the way I felt her body grinding into mine, her leg wrapped around my midsection.. she just oozed sensuality. I reached down and slid my fingers inside of her. So so wet. Admittedly, I barely spent any time fingering her, I just pulled my fingers out and replaced them with my cock.
I thrusted inside of her at a solid pace. I could hear my cock sliding in and out of her, she was so wet. I love that sound. The more a lady is enjoying herself, the more turned on I get and the more I want to pleasure her. I stood at the side of the bed sliding into her when I hear her breathe “harder…” in between moans. I was fully in my role at this point. I responded with something about her not telling me what to do, she needs to ask permission, something snarky.. and she responded with “harder, please”.
Maybe it was the newness of it all, maybe her saying please, who knows… But I started to cum already. Way to early, way too fast. We had only been going at it MAYBE 5 minutes. But I couldn’t hold it, and I just blew. I pulled myself out and just laid on the bed. I apologized a couples times, kept giving some excuses “you’re so wet, I haven’t came in a while, etc etc…”. She just cuddled up next to me saying it’s ok it’s fine, no worries, etc. Good on her. We cuddled for a little while, her leg across my body and me rubbing her leg up and down. She told me she wants me to dominate her, she wants me to make her beg, etc. That did it… Within minutes, I could feel my cock throbbing underneath her thigh.
I turned and started to kiss her madly. I pulled her on top of me feeling her smooth skin all over me and I told her to put my cock back in her. When she grabbed me I felt the condom that I still had on and, in the heat of the moment, told her to take it off. She did as she was told and threw it off the side of the bed, and put me right back in her. It felt a million times better. I had some errant “you idiot, wear a condom, your pants are right over there, grab one!” thoughts, but I was too into the lust of the situation, so I ignored it.
We went much longer this time. She rode me exactly how I told her I wanted to, she bent over and spread her cheeks like I told her to, I tried putting my cock in her ass and almost got the tip in a bit. She liked to be choked, so I had my hand around her throat while I was slamming into her from behind, hearing her gasping for breath. I would cover her mouth as she moaned. She started saying yes sir, no sir. Pure raw sexual bliss. I ended up back on top of her in missionary going slow and kissing her passionately before I started to feel the cum again. I told her I was gonna cum and where she wanted me to. She told me I could cum anywhere I wanted. So of course.. stupidly, I wanted to cum inside her (cumming inside a woman is the greatest feeling on earth, fight me 🤣). So I did. I pushed myself as deep in her ass I could and I had a proper nut all inside her pussy. I kept sliding in her, more and more, getting every last drop of cum I could out.
I remember basically collapsing on top of her, both of us breathing heavily. We laid back cuddling getting our breath back. We laid there talking for a bit when suddenly… I woke up. What the hell, when did I fall asleep? As I stirred, she woke up next to me saying the same thing, how did we pass out? We just laughed a bit until I grabbed my phone and we saw the time… It was after midnight. Of course it was nothing to me but she almost flies into a panic. She grabs her phone and says something about missed texts and calls. She starts to get up but I tell her to hold on.. I was too into it, power drunk off the domination and everything I had her do the whole night. She was saying something but I just said “put your phone down..”… And she did.
I wanted more before we left. Just one more round. I was intoxicated. I rolled over on top of her and put my lips to hers. We kissed for a while, but I knew we had to go. So we got up, got dressed, and went to check out of the hotel. We walked hand in hand to my car, all sense of urgency on her part had disappeared.. well ok then. We got back to the restaurant parking lot, and I walked her to her truck door where we stood making eyes at each other. I wanted more more MORE, and she didn’t seem in as big a rush anymore. I opened her back seat door and just let myself inside. She made a joke about me wanting to go home with her but I told her to climb in. She did and I had her straddle me. She kissed me full force again, her lips were perfection on mine. I ran my hands up her shirt on her back and grabbed her ass. I started to kiss her neck and down her chest towards her cleavage, she started breathing heavy again. I pulled at her pants wanting her to ride me again. We shimmied them off and she climbed on top of me again. I told her she can’t leave until I cum again.. and she rose to the challenge, grinding my cock inside of her until I had no choice but to cum. It wasn’t as powerful as the last time of course, but it was still amazing.
We got our pants back on and hopped out the back seat. I looked at my phone and it was damn near one in the morning, almost a whole hour after she was supposed to have been gone. I gave her another quick kiss so we wouldn’t get stuck again, and we went out separate ways.
We met up again a couple times after that. Once we went to a movie, and I remember it was a Liam neeson movie I think one where he was on a train or a plane or something, in the middle of the afternoon, and we went right up to the top being the only two people in the theater and we fooled around in there. I also went to her house to pick her up once, and when I dropped her off back home her family was there, and I wanted to push my luck, and we went to a dark space on the side of her house and hooked up for a few minutes.
Leann and I fizzled out soon afterwards. Just one of those things. She definitely helped me get more comfortable in the dominant role. I never looked her up or tried to get in contact with her after we stopped talking so I have no idea what’s going on with her. But I’ll always be grateful for her being one of the ones to broaden my sexual horizons a bit.
Source: reddit.com/r/gonewildstories/comments/ubnu0d/my_first_domsub_experience_mf