My [27m] first relationship with a younger woman [18f]. – Short Sex Story

I’d mostly fooled around with older women when I was, well, “more of a young man”. It got to be enough of a thing where, while I sometimes admired young women, I mostly didn’t consider them from more of an intimate perspective.

That shifted when I was 27…

…I’d never been the best academic. I spent a LOT of time in College, and, while my grades were *really* good (college all the time came very easy for me), I slacked off a lot. The end result of this was that I was 27 and really only about halfway done. Partly due to not taking a lot of classes, withdrawing if I didn’t like the feel of a class, and changing my majors halfway through my school ‘career’. Also, well, taking a break for a bit to just try going straight into the workforce and the deciding naaah.

*When* I was 27, I was getting more serious though, taking “full loads” and taking them pretty seriously. Some of those classes were things that, honestly, I probably should have taken earlier but which I hadn’t. So, there were some younger folk in my class and I was pretty much– well,- “the old guy”.

Which is how the issue started.

The very first day of one of my core classes that I’d finally gotten around to doing, this girl– we’ll call her Jessica,- popped into my class, spotted me across the room, and plopped down next to me and introduced herself. Kind of one of those, ‘instantly wanting to be your friend’ kind of people. Which, well, wasn’t something that I was used to but was enjoyable enough. We were class friends at first, then just became friend-friends, and…

…well let’s not get ahead of ourselves here.

In the beginning, I was a bit of a safe spot for her, an emotional stress ball that she’d distribute her thoughts with. She’d tell me about her tricky relationships with her roommates, the boys she was interested in, and all that kind of stuff. I didn’t mind; I know girls treating guys like that is almost a joke but I’ve never really minded and have all the time very much appreciated my girl friends and made myself available for them. Honestly, it was even more comfortable with our 9-year age gap, since I really wasn’t picturing her as anything more than an exciting less-mature little distraction.

…not that I wasn’t attracted..

This girl, Jessica, she was… well, sort of a hot. One of those “girl next door” fall-in-love-with faces. She had long loooong brown hair when we first met, and dressed really nice, but changed it up to shoulder-length and “freshman-casual” later on. She had a good enough of a figure that she all the time looked nice tho, and, one of those voices that you can listen to basically forever.

Things weren’t onesided, either, she’d listen to me as well. I at leaset gave the impression of having my shit together, tho, but she was very supportive when I did need a friendly shoulder.

Oh, and I should mention– she was *very* affectionate,- like, hugs at all times. Leaning off my arm when we’d walk, leaning against me if we were on a couch together. She even sat on my lap once, but that was a… extenuating circumstance.. rather than something that she just did on her own. Heh.

I figured she had a bit of an attraction there, and was flattered, but I didn’t really take any of this too serious.

Especially since she’d sort of developed a kind of “…are these two dating? I’m not entirely sure. I never really went through this when I was that age, heh, mostly cause my girlfriend was in her 30s..”


Sometimes, when she needed a car, I’d help drive her around if I had time to do so. She would sometimes hang out at my apartment, when the drama at her dorm got too much, and when I first got a call from her at some ungodly hour and drove to pick up a drunk-off-her-ass 18 year old school girl so she could sleep it off on my couch? I figured we were pretty close.

…it DID kind of occur to me that I was *basically* dating her, just, without any real sort of intimacy..

I honestly didn’t think it had occurred to HER, tho, or rather I didn’t think she had any sort of interest in me that way. I was happy with that, too. The one time I spotted her hanging around my apartment in one of my T-shirts and some panties? I was like, “No, you go put on some pants.”

She teased me a bit, but seemed amused more than FLIRTY, and as for my part I didn’t want to take this ‘thing’ anywhere remotely in that direction–

–partly because, well, I really liked Jessica but she was such a teenager. I was happy to be there for her, and to be her friend, but actually being in a relationship with her just didn’t seem like something I wanted to deal with. Especially since my relationships to date had been, well, one girl my age and a smattering of women older than myself.

She was too young for me and just a friend.

Or, you know, so I wondered.

(the sex starts here)
The trouble started one night when she had been spending enough time in my apartment, regularly enough, that her asking if she could stay the night just… wasn’t a thing. I just rattled off a sure, intending to make the couch for her, and that was that.

We watched a movie, I played some video games. Cooked us some dinner and goofed around a bit more on my computer while she was doing some of her homework. I felt more like her dad than her boyfriend. n’ I didn’t realize just how much that particular dynamic works for me back then.

So, yeah.

Eventually, I’m getting ready to turn in soon, but I figured she’d be up for a bit longer. So, I figured it was time to turn down the couch for her and began working to do such.

When she protested–

“Do we have to put me in the couch? Your bed is so much more comfortable.”

She’d known that because she would, occasionally, take naps in my bed for what I’d assumed were innocent reasons and later learn was because my bed smelled like me.

I just gave her a look–

–she just, “If it’s too weird for you, I get it, but come on? What are you afraid is gonna happen? It’s a big bed!”

I didn’t really stop looking at her…

…but I finally just shrugged and put the couch stuff away. At which point she was like, “Excellent, thanks, do you mind if I catch a shower first?”

I let her,– I had said very little at this point, honestly,- kind of just moving into the bedroom… and, well, mussing about with the covers a bit (I do not make up my bed) and thinking about what she expected to be happening tonight and what I wondered about that.

Deciding that, after a bit of wondered, that *probably* nothing was gonna happen– she was just very comfortable around me and didn’t wanna sleep on the couch,- but that if something did happen that…








I hadn’t really noticed the shower turning off, but I definitely noticed her coming out of the bathroom wrapped in a towel and giving me a look that told me that she definitely wasn’t ‘just that comfortable with me’.

It was one of those, ‘Why didn’t you come join me’ looks.

Which, well, sparks of electricity running down my spine. It didn’t help that her hair was wet, plastered to her face, and her shoulders were bare. I have a thing for shoulders. She looked very very good in that towel, is what I’m getting at, and the prospect of taking that towel off of her was..

…way more tempting than I wondered it would be.

Reminded me a bit of when I’d found her in a t-shirt and some panties, except, I was not at all tempted to read her the riot act this time and I’m fairly sure she could tell. n’, well, was absolutely tickled pink that she was getting what she wanted. Fairly sure she wasn’t wearing any panties either.

“(the shower) is all yours,” she noted.

I just nodded, “…yeah.. Thanks.”

I lingered a bit, but eventually moved into the bathroom, half expecting that she’d be coming with me. She didn’t though, just sort of tossed a ‘don’t take too long’ back at me, giggling a bit, as I disappeared into the bathroom.

I took a very quick shower.

I was also, well, pretty fucking turned on and wondering what sort of idiot I’d been that I hadn’t already done everything I could possibly do with this very very attractive woman that- honest with myself,– I’d wanted for a long time. Who, well, was obviously pretty into me.

Just a moron, I finally decided.

Putting a towel on and heading back into the bedroom, where she was sort of laying there, mostly covered by a sheet. “Mostly” because, well, it was keeping the scene from being obscene but it was still very much ‘erotic’. I could even see most of a tit! And, well, Jessica had very very nice tits. She blushed a little, just from the way that I was looking at her.

“Get in the bed,”–

–I had a moment of doubt right then. Like, I wasn’t wearing anything under this towel. I usually wear some underwear to bed, at the very least, and honestly, I wasn’t as bad as when I was younger but I still had some body-image issues back then.

She’d never seen me naked before.

“Noetic. Drop the towel. Get in the bed.”

I did…

…she let out a release of breath, made a *very* enticing sound, as the towel hit the floor. Looking at me, who was very very much on display at this point, and it was very obvious that she wasn’t displeased with what she was looking at.


I grinned a bit, ego boistered a bit, and I was barely into the bed before she was pressed up against me. A hand on my cock, lips on mine. One of my hands finding a tit and squeezing it.

We kissed–

fuck did we kiss.

If I hadn’t known that this woman wanted me by this point, and I’d figured that out somehow, I sure as hell would have known by this point. This girl was NOT shy.

There was a quick, “You’ve been hiding this from me,” kind of tease.

…and then, well, she was taking me into her mouth..

I– let that go for a bit. I didn’t really do well with blowjobs, especially back then, and in that moment? That just wasn’t what I wanted. So, you know, pulled her off… kissed her.. pushed her back onto her back, hands all over her while she moaned and groaned and begged for exactly that. I was kissing her body, sucking on her tits,– spanked her ass, which she liked,-

When I started fingering her, though, she had a moment of her own kind of asking me to stop between whimpers.

I was tempted to keep going.

But, I stopped when she was like, “Please, please Noetic. We can do this again later and you can take all the time you want. You can feel how wet I am.”

I could; I said so. “I really really can.”

“I need it, so bad. Please.”

She was practically fucking begging me, and if the words weren’t bad enough the look in her eyes was even worse. So, well,- I’m a pleaser, at the end of the day,- I wanted to give her what she wanted and it wasn’t like I wasn’t ready. So, I slid ontop of her. She knew exactly how to move, spread her legs for me…

…I was a bit surprised just how TIGHT she was..

I mean, it wasn’t a enormous thing, and I knew enough about her school love-life to know that she wasn’t a blushing virgin or anything. She was *so goddamned tight*, tho, and honestly it didn’t really seem like she could even take me. I have, well, sort of a big dick? Thicker than it is long, but, long enough as well. And, like, I was going in fairly well with how wet she was but it was still quite the show… the way she was reacting..

The way her eyes rolled up in her face.

Just.. FUCK.

I was trying to be a little teasing, a bit easy on her, and she was NOT having that. At all. Just, “No, no no no. Don’t– stop being a nice fucking guy for 15 minutes and fucking RAIL ME! You won’t hurt me, I promise, please. I can take it. Give it to me!”

…like I said. I’m a pleaser..

I did what the woman asked.

I won’t say it was the best sex I’ve ever had, I’d had some fairly good sex at that point in my life, and she certainly wasn’t “better” than my older partners. The experience of being with this tight little school slut, however, was VERY different than any of them.

Especially just– how IN CHARGE I felt-

She wanted me to take control of her body, she wanted me to ruin her, and that was exactly what I did. I slammed into her, I fucked her like a little whore, and she was so goddamned into it. I choked her, slapped her a little. Teased her nipples. I filled her up and she’d just MOAN, nails dragging down my back, drawing blood as I’d later learn. I put her fucking legs up on my shoulder, railed her HARD and DEEP while she just kind of chanted about how deep I was getting and how big I was, and fuck, this girls eyes and the expressions on her face–

–the shit that came out of her mouth,-

Jessica was the girl that really taught me to enjoy, well, really FUCKING a woman. Just, tossing her around the bed, pushing her face down into the cover and having her stick her ass up in the air, fucking railing her and making her scream into that pillow that she’s biting down on.

Honestly, I fucked this little bitch the way that some of my previous lovers probably wish I’d fucked them, and the words that came out of my mouth felt like they were said by someone else because I didn’t talk to women like that.

But, she loved it.

I’d never, in my life, heard a woman tell me to fuck her little whore cunt but I did that night.

And, it felt SO fucking good. I wasn’t in any danger of cumming anytime soon, and she was, but god DAMN it felt so goddamned good to rail this girl that I’d silently wanted for so long. This girl that I’d been quietly taking care of for the past couple of months. Who I wondered of as almost a little sister.

n’, I was fucking her so good that she lost the ability to form coherent sentences and just kind of *broke* right there on my bed. She made SO MUCH goddamned noise when she came, and I kept right on fucking her for a bit, until she was just a shuddering whimpering little mess on my bed.

Then, I collapsed next to her..

…cock wet and covered in our juices as it lay against my stomach, still very much hard, even as she rolled into me and kissed me.

At least, until she REALIZED that my cock was still hard.

Then she looked at me with this look on her face, like I’d done something so fucking wrong, and was like, “You didn’t cum?” in this voice that actually had me feeling guilty.

We didn’t fight about it or anything.

She started blowing me again, and honestly, this time I was a bit more into it. Thought if, maybe, she’d be the first girl in my life to make me blow my load down her throat? I wanted to, she was SO FUCKING HOT blowing me, too. She obviously knew how to do it, and I wanted to talk to her about where she’d learned, but it was while she was playing with my balls that I finally was just–

–“I’m not going to cum like this, I need your pussy.”

She was right there with me, just nodding, “How do you want me?”

“I always cum the easiest when I’m being ridden,” I said.

She got this smirk on her face, nodding, climbing herself ontop of me and looking like she was well and truly in her zone now. “Mmmm, I’d like that. You’re in for a treat, baby. I really like to ride dick and you have a very very nice dick.”

And, well, she wasn’t bragging.

She was *so fucking tiny*, honestly, but god damn that girl could ride dick. It was captivating to watch, too, the way that her breasts bounced as she rode me. My hands on her hips, my own hips working against her. I tried to work her clit a little, too, but she stopped me. Kissing my hand.

“No, this is for you. I want you to cum for me. To cum inside of me, fill me up, mmmmm. Please please fill me up?”

…being pressured to cum is one of those things that doesn’t often work with me, but seriously, this girl hit parts of my brain that I didn’t really know existed.. I wanted to do it. I’d known that I wasn’t wearing a condom before this point, anyway, I wasn’t really that worried about it.

Partly because, well, I wanted it too.

Mostly because I have a very good pull out game.

I was right there with her, she was fucking riding me like a goddamned demon, just SO fucking good. The way that girl moved her hips, the way she moved her BODY. It wasn’t better than I’d ever experienced, per se, and looking back she could have learned a few tricks. But, it was SO FUCKING DIFFERENT, and she just… it felt incredible.. I was overwhelmed.

I had already been really close.

n’ once she started to sense weakness, I swear to god it was like that woman could just SMELL how lclose I was, and she showed absolutely no mercy. Just fucking riding me like she was possessed, until my grip on her hips tightened and I just started meeting each thrust with one of my own, until I just pushed into her and held her tight to me.

She said something, something like, “Yessss, that’s it,” and I fucking UNLEASHED. Just, a final overwhelming moan joining all of the other tortured needy little sounds that I’d been making as I bottomed and just drained my balls into this woman. It felt like so much, and sure enough, a lot of it was dripping out of her as she finally pulled off of me. I was fairly sure what she was gonna do next, but, I beat her to the punch.

I honestly think I broke her brain a little when I buried my face between her legs and started licking her clean. If not then, definitely when my tongue… went somewhere else.. earning a quick, ‘what, no,- st— don’ DON’T STOP! OH FUCK!’

I made that little bitch come for me with my mouth, heh, and I think she was a little mad at me after that but didn’t really hold it against me very long.


She was weird about kissing me for a bit, but that too passed and we ended up naked and sweaty in bed together, kissing. Until, well, she was asking if I was ready for round two and I found that you know what I sort of was.

She even gave ‘blowing me’ a good ole’ school try, after we talked about why I kept stopping her and then she got it in her mind that she HAD to be my first, only to eventually give in to giving me her pussy again and begin screaming loud enough that some of my neighbors were banging on the wall and telling us to go the fuck to sleep.

Which, well, we did.

After I filled her again.

Kissing gently, her cuddling my arm, both us ‘sated’ for the moment and just– well,- overwhelmed with each other.

She was finally like, “Was I your first teenager?”

In just this sweet teasing little voice. Looking up at me with these eyes that, if I hadn’t been so fully spent, might have inspired me to tell my neighbors to go fuck themselves because I wanted to fuck her one more time even if it was pretty late.

Instead, I just smirked and said, “Yeah.”

“Mmmm, you seemed to like it. I wasn’t sure if you were gonna go for this, you know, until I came out of the shower.”

“Neither was I,” I noted, grinning.

…and, well, we talked. For the first time in our relationship, no one would give me shit for listening to her talk about relationship shit, and honestly… I found it even more cute.. and thought why I’d ever worried about any of this.

Yeah, she was sort of silly and not secure in herself. She’d shown a LOT of confidence when she was *fucking my brain out*, but, most of that had boiled away in the quiet cuddling make-out session that tired as we let the energy drain from her body.

…and, well, I wasn’t annoyed..

It was sort of ‘oh god this girl is such a little kid’, sometimes, when she was talking about OTHER guys. But, when she was talking about me, it was sort of weirdly endearing. And, just, it’s a different experience when you still have the taste of her in your mouth while you listen to her go on and comfort her. When her naked smooth skin is under your hand.

When you’re *kissing* her.

So, yeah, as might be obvious by this point in the story that wasn’t my only time with Jessica. She assured me, a couple of times, that it’d be fine if it WAS. That she’d have regretted it if she hadn’t had done it, but, that it didn’t have to mean anything. But, it did mean something, to both of us.

n’, we both wanted more of it, and more of everything else too.

She didn’t exactly ‘move into my apartment’ or anything, but we were definitely dating, and the relationship was actually one of the longer ones in my life. Two years. A good chunk of 18-year-old her, all of her remaining time as a teenager, and then finally petering off not long after she’d turned 20.

…in, honestly, pretty messy fashion..

We didn’t adjust well to “me not in college” and “her still in college”, basically, since our relationship was VERY MUCH of a “college” relationship-style. Neither of us particularly wanted the relationship to end, we both cared for each other very much, and we were both very much addicted to the sex. Heh.

I certainly was, anyway.

But, at the end of the day, she was still a school girl and I was trying to establish myself as an adult. (Before THAT blew up in my face and life revealed her plans for me.) We were gradually growing aside, and try though we might, things just weren’t going that well.

It ended with sort of a whimper.

Just… her giving me back the key to my apartment, having already cleaned out most of her stuff over the past few weeks, apologizing for hooking up with that guy at that party, looking like she was gonna say more and just– not,-

I smiled, touched her cheek, said it was okay, and…

…watched her walk away..

I didn’t even really blame her. We should have STARTED our relationship months earlier than we did, and, we should have ENDED our relationship months earlier, but she ‘cheated’.

But, I needed what happened to admit to myself that she was something that I wanted.

n’, she needed what happened to admit to herself that our relationship wasn’t gonna work anymore.

And, that is that story.

NSFW: yes

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