An Older Woman Helped me Explore My Kinky Side

“Choke me,” she said.

Two words. This was the key that unlocked a door I’d never close again.

Preface:
This story is from my past. I’m 36 now, but all of this happened at a younger age.

At the age of 21, I was coming out of a four-year long term relationship. I was afraid of change. I was content at the time because it’s all I knew, forever afraid to step out of my comfort zone. She and I both set our lines in the sand and we never crossed them. I settled in and spent four years thinking she was the person I was going to spend my life with. This was not due to any magical connection or fiery chemistry, more so because we were too afraid to try anything new or attempt to face our clear lack of compatibility.

Our sex life was only explored on rare occasions. It felt like constantly waiting on the groundhog to pop out of the ground and tell us we were in for a good spring. Insecurities made me a bad partner, and her promiscuity led to fights that should have pulled us apart, yet I held myself in place. Whenever an opportunity for adventure would come up, we’d be so disconnected and my bids for connection would be turned down so harshly, that I felt I was at my lowest. The feeling of rejection stayed with me and I started to lose my own self esteem. I realized I wanted to feel desired, and I never felt that with her. Finally, I left.

Shortly after I ended that relationship, right around my 22nd birthday, I moved in with a friend of mine. His mom owned a large suburban house with six total tenants. I became the seventh. The rent was cheap, I had my own small room, and due to everyone on the top floor working overnight, I could play my music at 2:30 in the morning upstairs while nobody was around. I read books, I worked out, I kept to myself mostly. I agreed to do some of the chores to help out around the house, but I’d wait until everyone was at work to start my trek downstairs to the kitchen.

One night, walking downstairs with my headphones around my neck, I met one of the other roommates, a forty-two year old woman who had apparently known my friend’s mom for several decades. I’d find out later she had been married for the last 19 or so years and was still working through her divorce so she had moved in about a month before. We ended up talking for about two hours around the kitchen island – life, dating, relationships, movies… all of it. I poured her a drink and we continued sharing our stories.

A lot of our conversation revolved around how “stuck” she felt in her marriage, as if she had lost her sense of self. This resonated with me, albeit not on the same timeline as her story. She had been on a newly discovered path of self confidence, taking pole dancing classes, going out to bars and clubs to experience the nightlife, doing all the things she had never gotten to do as a younger adult. I listened intently and sipped my drink, nodding. Before I knew it, it was nearing 2 AM and we ended up hanging out on the edge of my bed in my room.

We were initially going our separate ways, since she was right across the hall from me, but the talking continued and we just kept getting closer to one another. I felt shy, but also intrigued by her – by the way she carried herself so confidently. She also looked like a woman way out of my league. I couldn’t fathom the possibility of this turning into anything, but the conversations were engaging and interesting. Let’s not disregard the fact that she looked stunning. Her hair was recently dyed an auburn brown color, roughly shoulder length. This particular evening she was coming back from a date (a bad one), so she had her makeup on and she looked and felt her best. Eventually I caught her staring at my lips as I talked and started to get a flirty vibe. I denied it as long as I could. I still felt horrible from my previous relationship experience, so I didn’t know that I was ready yet.

“I really want to explore and just go crazy, you know? I just want to get fucked the way I deserve,” The words poured out of her mouth heavily like concrete, slamming right into the conversation we were having. I didn’t say anything, I just looked down not knowing what to do, in shock. I might have let out a small, nervous chuckle. I’ll admit, back then I wasn’t the best at knowing when someone was flirting with me, but it became clear when she started rubbing and squeezing my thigh and saying these sorts of things.

When I looked up at her, she was looking right at me, not cutting eye contact. It was a stare wrapped in warmth, filled with desire. Slowly her eyes drifted back to my lips again. This was the first of many things I’d learn that evening – when someone is staring at your lips the way she did mine, they definitely want you. At the very least, seductive thoughts might be taking place.

“Do you want to fool around?” She asked, almost the same way you’d ask someone if they want to go to the store and grab a bite to eat. Casually flirty, but sharply to the point. My cock grew and she saw it pretty much immediately.

Fuck! What am I doing, I thought. I was just frozen in place, unsure of myself. I was afraid my lack of experience or self esteem would cause issues and didn’t know what to do. I’m pretty sure my voice broke a little bit when I tried to respond. Before I could get anything out she pulled herself closer to me and let out a slight giggle. I felt like I was prey in her web, but I liked it. I really did want to say yes.

She leaned in and switched over to a sexy, soft voice, whispering to me, “You’re okay right? I really like younger guys. Since you walked down those stairs I’ve been thinking about it. Maybe it’s the wine, but hey. We’re here. Nobody else is. And it’s not like I’m making out with my date tonight since that went badly. What’s the harm?”

A moment of silence. Finally I said, “What does that entail… exactly? Fooling around…”

Without hesitation, she gripped my cock through my jeans, “Well, I play with you and we see how things go from there?” Being a young lad without much experience, my jeans almost became cum-soaked just from her grabbing me.

I flinched downward and let out a murmur, which sounded like, “Holy SHIT! Yesss.”

Up to this point I hadn’t had sex outside of a relationship, so the whole experience would be new to me. I didn’t know what to do with my hands most of the time, but she had no problem grabbing my wrists and leading them where they needed to be. We slowly undressed and she kept her mouth to mine, her tongue swooping in and taking my lips the way she wanted. I felt the nibbles of her teeth against my bottom lip and all the sensations of sharing passion with her. Occasionally she’d grip my lip in between her teeth and chomp down as hard as she could, then laughing at me as I tried to regain my composure. I was in a state of anxiousness, yet more turned on than I ever had been before.

Most of the kissing I had done up to this point wasn’t like this. This felt different. This felt.. incredible. My cock was so swollen in my pants, it almost hurt to slide them down so that she could have full access to me. She placed my hands on her breasts and squeezed them, encouraging me to massage her while she kissed me.

Her scent was a bit overpowering, a wave of different perfumes and lotions, but it wasn’t so loud to my senses that I couldn’t continue the experience, or enjoy it. For the first time ever, I had felt a woman’s mouth all over my body. She worshiped me for a while, grazing my back, my hip bones, my chest with her fingers and lips, eventually leading to her pulling my pants all the way off and working her way up my feet and legs back to my cock. Before I knew it, she locked eyes and her mouth fully engulfed me.

I mentioned that I felt bad, not giving back to her as she did all these things to me. I wanted to make her feel good too.

“You should,” She retorted, almost in a demanding voice.

She grabbed my hand and moved it to feel her pussy through her panties – completely soaked, dripping down her inner thighs. I’d never experienced a woman so wet before. All I could think about was tasting her. (Eventually we’d have a second encounter where I did and that’s a whole other story)

She continued sucking my cock as I rubbed her clit through her lace underwear. I used my palm to cup her pussy so that I could make sure I gave her full sensation as she went to town on me. Having not much experience to this point, I was ready to cum about every ten seconds but kept holding back as best as I could. I tried my hardest not to explode in the back of her experienced throat, even though I wanted to so badly. At one point she swallowed my cock all the way down and stuck her tongue out at the base of my balls, lapping them up, her eyes looking up at me on the way back up, all watered. She grabbed my hand and forced it into her hair. I gripped the best I could, but she pulled herself back up and showed me.

“Right here, grab near the scalp, not the ends. Yes, just like that. By the way, I’ll say ‘red’ if things get too rough, so feel free to just do whatever,” she said.

I had no idea what this meant at first. I eventually recognized it as a safe word, but kept wondering, Why would we need those? She looked me dead in the eye and whispered, “I want you to make me your slut. I want to be a dirty slut, okay?”

What? My slut? I’m not sure if I want to date right now or have anyone be my…wait, I’m not sure what she means?, I thought to myself. I held her hair there, almost in shock. This woman was so out of my league and I was trying my hardest to keep it together. I didn’t know what I was doing, but I tried my best.

“When I have your entire cock in my throat, then I’m your slut…” She smiled at me and let out a laugh. I laughed nervously, still a bit uncomfortable, but edging up to saying something.

“You’re… my slut,” I said, softly – unsure of myself. Hilarious. How embarrassing. I wanted to die in that moment, because I could even hear how pathetic it was. She pulled my cock back out of her mouth, teasing the head of it with her tongue. It almost went soft with how embarrassed I was. A giggle came out of her and she said “I know you have it in you. Come on, you can do that way better. Grab my hair like this,” she solidified my grip on her hair with her hand and made me squeeze it so that I had full control of her entire head.

“There you go, now you can do whatever you want. So, FUCK. MY. FACE. You’re not going to hurt me. Fuck it the same way you’d fuck my pussy. And you can call me a SLUT. Yell it at me if you want.”

Holy shit. Holy shit. I couldn’t think straight. She looked up at me waiting. Her eyes were piercing through me at this point. I knew what was expected of me, but could I pull that off? I didn’t want… to hurt her. I would feel bad if I…

“Fuck my face, please, Do it. I want so badly for you to use my mouth. Use my throat and if you have to cum, just cum, I’ll be a good slut and swallow all of it,” she said, playfully bending over and shaking her ass opposite of me.

Her eyes still kept contact with mine. She was slowly tracing her lips around the head of my cock, just teasing me. It’s like she was waiting for my move in a game of chess. Almost in an “I dare you” sort of way. I remember feeling like she’s not the one blowing this, I am. Her light tongue movements felt amazing, but I knew what was expected of me. She smiled at me and raised her eyebrows before pulling them back down. At this point, I felt taunted, like she was guiding me into being the dominant one. It definitely felt like she was toying with me. While I had no experience in doing so, her eyes locking onto mine and her pussy dripping down her legs seemed to be enough to snap me into play.

I wound up a tuft of her hair at the scalp just like she showed me and I forced her head down onto my cock. She opened wide and took all of me inside the back of her throat. Her hands wrapped around me toward my back as she pulled herself into me further. Once my cock got in and I started using her mouth, she moved one hand into her panties where she rubbed her clit.

“Mmmm,” she moaned, taking my cock deeper.

“You’re my fucking slut, understand?” I said. A little better. It felt weird at first, so foreign to me. I had never talked to someone like this. She moaned louder after I started talking dirty. While I’m well aware that sex isn’t typically like a hardcore porn you’d see, there was something about this woman that felt very different from the sensual love making I was used to. She was empowered and strong in a way that taught me so much just by being there with me. She knew what she liked and wanted and she just… went after it. I admired that about her and admittedly wished I could be more like that.

“Your pussy looks so wet, you must enjoy having your face fucked by a nice young cock, huh?” I said, with much more confidence in my voice. Her eyes lit up at me and she sucked harder. The heavier my voice got, the more confidence I showed, the more she reacted. My cock was almost ready to burst.

“Yes, you take that young fucking cock,”

She leaned back briefly and with spit drooling from her chin said, “You should’ve seen the guys I fucked behind my husband’s back,” just before diving back down on my enlarged cock. I was so turned on by that for some reason, I almost shot my entire load right into her throat. (Little did I know that would later lead into certain cuckold/stag/hotwife kinks in my brain, but that’s for a later time too)

“Mmm, You’re such a proud slut aren’t you? Take it deeper, there you go.” Her fingers moved faster around her clit and she seemed to be getting nearer to her orgasm. Her mouth continued taking me, but by this point I had taken more control. I felt like the master in the scenario now. I was showing her that she needed my cock and she did nothing but beg for it from then on out.

“This face deserves to be fucked, I want to feel the back of your throat, you little slut.” I finally got my rhythm with her mouth on my cock and pulling her on and off of it, allowing her little bits of air as she’d come back up to the top. She didn’t mind staying down as deep as it could go, although occasionally she’d gag on it and I’d start to feel like I was hurting her. She’d assure me I wasn’t and if I slowed down on the facefucking, she’d pull me right back into her. She made a few more comments about being treated like a “depraved whore,” and how much it made her wet, so I kept up the act for a while.

Eventually I started to flinch, my cock started pulsating in her mouth, nearly cumming, when suddenly she yanked herself back to stop me.

“Don’t cum yet, I want it inside me!”

“What? I can’t…” I held it as best as I could. Oh my god, I was nearly bursting and it almost hurt to grip myself and not let it go. I could feel it wanting to just spray out all over the room. It had been built up for hours in just the conversations we had, all the connecting and transparency between us. I was ready and yet I had to stop myself.

“I want your cum inside me. Don’t worry, I got my tubes tied years ago, you can do it, it’s fine.”

She stroked my cock for a moment while she removed her panties. Pushing me aside, she almost shoved me off the bed so that she could get into a prone position and spread herself open for me to see everything. Her pussy looked so tasty and delightful. Cleanly waxed, well kept, pretty and pink. She had a little bit of an innie, where it was all hidden away in a tight cute little package, but once she spread herself open her labia fully started to show and unfold in front of me. It was so inviting.

“You like it?” She smirked.

“Yes, yes, I do,” I said, running my fingers through it. I massaged her lips and worked my way to her clit for a little while, slowly exploring it. The clitoral hood was lifted slightly revealing her little button underneath, I rubbed on top of it and pushed it a bit to see her different reactions. Her juices seeped out onto the blankets below as I slid my fingers in. I felt how warm and lovely it was inside of her mature pussy and my cock started growing again. She spread her ass cheeks for me so I could play with her for a while. I wanted to taste her but she wanted my cock inside of her.

“I had it waxed for the date, but might as well not let it go to waste right?” She joked, before continuing, “Please fuck me, please, please.” At this point she was much more submissive towards me, begging for me to push myself inside of her.

I chuckled about her date and wondered what that guy did to send her home disappointed. Either way, I was glad to be on the learning end of this experience.

“I’m your slut, please use me like one” She said as she started rubbing her clit again. “Please, I need it so bad. I haven’t had a good cock in so long. You can do whatever you want with me,” She said, her face turning slightly towards me so that her eyes could keep some sort of connection with me. She started shaking her ass and begging and pleading for my cock to enter her.

I knew that the moment I did I might burst inside her. I had to be careful. I straddled her from behind and started slowly rubbing my cock around her pussy lips. She was soaking wet and ready. With a quick thrust she pushed her ass back onto me and my cock slid right inside her. She was warm and my cock felt so engorged. She was slowly being stretched out over my cock as I pushed it in a little further with each thrust. I was trying hard not to cum, but she wanted more. She forced her body back onto mine and started fucking me herself. I took control and grabbed her hips and shoved her into the bed as hard as I could and yelled, “No, you will wait for me to take you how I want you!”

She let out a bratty whimper and tried pushing back again, so I quickly and playfully smacked her ass and pushed her back into the bed. She laughed at me and said “Fuck! There we go, Oh my god.” I planted my dick deep inside her and held her there with my body, slowly moving it around inside her.

“You’re a useless little slut here to please me aren’t you?”
“Oh my god, yes.”
“Say it,” I commanded.
“I’m your useless little slut,” she said between quick breaths.

Her fingers aggressively rubbed away at her clit and she blurted out “I’m going to cum soon, please fuck me as hard as you can…as hard as you want. Open me up, I need it.”

I listened. I leaned down with all of my body weight and started pounding her from behind, my hands traversing up and down her back. I admired her shoulders, all the cute little moles and blemishes on her skin. She was so beautiful. Her body was smooth and smelled sweet, but I know she had lathered herself in lotion earlier in the evening. Some sort of vanilla scent. I kissed her back and made my way around as I pounded myself inside her, filling her up as deeply as I could. She groaned each time I pushed her further into the mattress. My teeth grazed the back of her neck as I bit her and held her there in place.

“Mmm fuck! Fuuuuck, yes, hold me down and ruin me,” She yelled.

I admired her ears poking out of her disheveled sex hair and traced my fingers across them to fix it, then I messed it all up again as I gripped her by the hair and dug my cock in farther. I felt the warmth of her tight pussy take me all the way in and I knew I had to cum any moment now. She leaned upward so I could get a grip around her to her tits, squeezing her nipples in my hand and massaging them while she pushed herself all the way to orgasm.

“Fuck, i’m so close, yes,” She moaned.

Eventually I made my way up to her neck with my hands, grazing it beneath her jawline. Her neck looked so tiny like it could fit right in the palm of my hand, and just as I thought of that very idea, she pulled me down closer to her. My hand landed on the bed sheet in front of her and she said the words.

“Choke me. I want you to choke me.”
There it was.

My dominance kicked in and I did. I placed my hand carefully on her throat, and she guided me, “Here, not here. Squeeze here.” I followed her instructions and had my thumb and two fingers on either side of her neck and pressed into her, being careful not to press in on her esophagus. She moaned and held my wrist with one hand, her other steadily playing with her wet cunt beneath me. I could feel her arm under her body almost violently pushing downward from the force of her fingers rubbing her own clitoris.

“Oh my god, oh my god, please fuck me! FUCK ME! HOLY SHIT!”

I rocked into her back and forth, my cock stretching her pussy open as much as I could. I could feel her juices spilling out of her, drooling down the bottom of my shaft. Once I gripped her throat into my hand, her pussy opened the flood gates and she sunk right into me. That was the moment I took a chance. I leaned into her ear, “You’re going to cum for me, aren’t you? That’s what sluts do, don’t they? The get fucked just like you do. Just like when you cheated on your husband those times. Just like now! Giving away your used pussy for any young fucking cock that walks in the room and wants a taste of you. You’re such a FILTHY FUCKING SLUT.”

“OH MY GOD, YES, Yes, I’m such a slut. Holy fucking shit, yes. I want to be the filthiest most useless little slut for you,” She moaned and convulsed right in my hand, my grip tightening around her throat.
“OH MY GOD, I’M GOING TO CUM.”
“Yes, good, cum for me!”

I held her there and fucked her from behind as hard as I could until I exploded inside of her. My cum shot in her with the most power I had ever had in any orgasm. My balls were pulsing and pumping all of me inside of her. Her fingers kept rubbing her clit as my hot load filled her up. The firm grip around her throat held her in place – I had never, up to that point, ever felt so confident in my sexual abilities or myself.

“Oh my god, use my pussy, FUCK!” she screamed, as I continued pumping myself inside of her. Her legs quaked beneath me and her body forced me out of her just as quickly as she had pulled me in. She shook underneath me with force, and let out a powerful yell with her orgasm, “FUUUUUCK”

She sunk right into the bed, turning herself over into the fetal position as I wrapped myself around her. We cuddled for a bit and we took turns tracing one another’s skin with our fingers. We didn’t say much. We started to fall asleep but then heard my friend coming home from his overnight shift. He walked past the door and we had to wait for him to go take a shower before she could leave the room. Laughing and smiling at one another, she told me, “I really didn’t know you had it in you.” I felt embarrassed almost, but proud of myself with the outcome. After she went to sleep, I masturbated twice more at everything that had happened. Lo and behold, I discovered I did have a dominant side (and a submissive one too) and it’s been my main kink ever since.

Source: reddit.com/r/Erotica/comments/zwwu8t/an_older_woman_helped_me_explore_my_kinky_side