Matched with Mom? Ch. 01

My head was spinning with lust as I looked through the thumbnails, the raw, sexual images slowly driving me crazy. I watched a few, pretending through the POV that I was fucking them all. A tall blonde, a petite redhead, a voluptuous, dark-haired Latina with great tits. They were all so goddamn hot. It was a fantasy world, a paradise of MILF pussy. I picked one, a guy laying on the bed while a brunette 30-something rode his hard cock with wild abandon. The woman moaned, bouncing her pelvis on him, her pendulous tits flopping with each rise and fall.

I groaned and stroked faster. My breathing quickened and I felt my cock swell with pleasure. As I jacked off, I suddenly narrowed my eyes as I noticed the woman cradling the subtle swell of her belly as she arched her back and thrust her hips forward. Oh shit, was she...pregnant? My eyes widened. Her belly was still mostly flat, but with the slightly pushed-out navel and rounded swell, it was clear that she was knocked up. A real mommy-to-be.

It somehow really turned me on.

"Fuck," I gasped. I'd never really considered the idea of having sex with a pregnant woman. Before this, the notion felt like putting gas into a totaled car, but now that I was on this older woman kick, the thought was a new turn-on. I kept jacking, looking at her little belly as it heaved during the rough sex. I mean, wasn't that the natural progression though? The idea of getting an older woman, a mother, knocked up with my own baby was so damn hot. Making her mine. A young stud totally invading her soccer mom life to replace her husband as a superior mate. I paused the video and went back to the search page, selecting a video of a MILF with a massive baby bump riding a 20-something guy, her 9-month stomach rippling with the motion.

Holy shit. The video was a close-up, focused on her bare, round, heavily pregnant belly, swollen tits resting on its shelf. I started to pump harder, gritting my teeth as I watched the video, imagining that my cock was inside her. The woman moaned in absolute, feral pleasure as she fucked the guy, her rounded bump rocking and undulating with the thrusts, hands cradling her abdomen.

I couldn't take it anymore and came. I gasped as I spurted hard, thick streams of cum all over my fist, stomach, and chest, the force of it taking me by surprise. My eyes rolled back and my whole body tensed as the orgasm swept through me, wave after wave. I shuddered, groaning with relief as it subsided and suffused me with afterglow.

Fuck, that was intense. I lay back and savored the warm, pleasant buzz from the weed and the post-nut bliss as I stared at my ceiling again. My cum glistened and dripped down my chest and onto my abs, my cock soft and shiny with my own lubricant. I took a deep breath and reached over to grab my increasingly used jerk-off towel from its place under my bed and wiped the thick, sticky seed clean.

I'd really came a lot. Shit. The videos had excited me way more than I'd expected with such a huge load. It was almost like the porn was a new, unexplored fetish or something.

I pulled up my jeans and chucked my sex towel into my hamper. Maybe I'd gotten a little carried away, but the thought of being with a sexy, older woman and breeding her was hot as hell. Maybe not an immediate thing, but eventually, if it ever got that far.

I got changed to go to the UMich fitness center closest to me, pulling on a sleeveless black Nike hoodie, gym shorts, and a pair of running shoes. I mixed up some C4 pre-workout powder and chugged the strange blue concoction from a plastic water bottle, chalky, gritty, and tasting vaguely of artificial orange. It gave me a serious boost though, enough to get me through my usual 3-hour workout. I grabbed my empty Wolverine Nalgene, student ID lanyard, and put in my Bose Sports earbuds to start my workout playlist.

'Take me back, to a place

Where I felt at home

Take me back, to a day

When we weren't alone

Take me back, to an age

When the world felt small

Way back beforeweblewitall...'

As I made my way through campus, head down, hood up, I started thinking about the end of the semester, about returning to my parent's place. Things with Mom and Dad were different now. I was an actual adult, off on my own. I'd kept my distance even though they just lived across town in Eberwhite, the beautiful suburb I grew up in with my sister. It'd been a good childhood with lots of love, but Chloe and I weren't all that close growing up even though we were just a year apart. I didn't have all the details, but knew my mother wanted a bigger family as she'd had us so young, but after me, that was it.

Mom and Dad were still married and seemed to be doing alright, but I wasn't as close with them as I used to be either. They didn't understand how hard college was for me, even if it wasn't a big deal academically.

The last time we'd been together was for two days on Christmas break, and that was awkward as hell. I'd made the mistake of bringing Emily over as Chloe wasn't coming. I could tell Mom didn't like Em. She kept her polite smile on the whole time, but her eyes were cold. When I was alone, she encouraged me to keep dating, and reminded me not-so-subtly that college was a time to experiment and meet new people. Emily had cut my homecoming short, insistent that my parents hated her. I'd resented it at the time, but Mom was right. As usual.

My mother was always the one I was closest to. I had a lot of her mannerisms, her expressions, and quirks. She was smart, funny, and very pretty. Mom and I were able to talk about almost everything, but I hadn't opened up to her since graduation. They had their lives and I was stepping into mine.

Mom was a specialist pediatric nurse at the Children's Hospital in Detroit. Dad was a simple, generous guy, a pharmacist. He loved sports -- a diehard Wolverine -- and he was the one who'd pushed me into football and soccer when I was younger. I hadn't been bad at either, but I'd lost interest as I got older.

Chloe was the black sheep of the family, a ballerina tween-turned-hardcore punker who played lead guitar in some band and had a dozen piercings. Mom had a hard time relating to her and tried too hard, while Dad was happy as long as his kids were happy. Chloe'd fucked off to Parson's in New York to study Fashion or something and I hadn't seen her or really talked to her for 2 years.

But whatever. It was a nice day, the sky bright blue and cloudless, the sun warm. I passed campus buildings, the library, and the grassy quad. A lot of UMich students were out enjoying the nice weather, sprawled on the grass, hanging out, and sitting in clusters. I was just one person in the crowd, a peer but still a stranger.

'...I wanna feel again

I need a couple friends

I never really understood just how the story ends

But I can feel it's tense

Don't know the consequence

The volatility of life my only confidence...'

I hit the gym hard. Deadlifts, bicep curls, shoulder press, lat pull downs, and core work. I finished the whole circuit and headed over to the weights rack. I set up the bench press, warming up and then getting serious. There were some other regulars there, like Luke and Sebastian, but we mostly kept to ourselves unless we needed a spot.

It was a great way to clear my head, honing my body and feeling the burn in my muscles. I did another circuit, then a savage round of diamond pushups, then crunches. It was a brutal routine, but the payoff was worth it. I decided to do my cardio outside with a long-distance jog around the university to enjoy the beautiful spring weather some more.

I ran the whole 3.3-mile circumference of the campus, passing the U-M hospital, the art museum, the Rackham building, and the Diag. It was a gorgeous place, with the old buildings, the sprawling campus grounds, and the green lawns. I'd run this route so many times that the path was familiar and I could let my mind wander, legs on autopilot. The temperature was perfect, and soon I'd worked up a good sweat. I took a break halfway to hydrate and catch my breath, enjoying the beauty of Ann Arbor's spring. Magnolias, cherry trees, and dogwoods, all blooming and blanketing the sides of the road in a riot of blossoming colors. The crisp air smelled amazing. The only time that might've been more beautiful in Michigan was fall.

Yeah, it wasn't all about the in-state tuition; I had a lot of good memories in my hometown. I could have chosen UCLA or Chicago University, but I just didn't want to leave. Maybe subconsciously I wanted the familiarity, the proximity to home. I was almost pulled from school back in 11th grade due to severe clinical depression; through a combination of counseling, Paxil, and a lot of understanding and love from my parents, I'd come out of it at the start of my senior year. Still, scars from that time remained, and I often had to check myself to ensure I wasn't falling back into that dark place without a bottom.

Sometimes I felt like the meds had fucked with my personality; like I wasn't as fun as I used to be or something, and at the worst, like, maybe I was the problem in all my relationships. Like my game had to be re-learned after a socio-emotional stroke or something. Being in familiar surroundings for such a big life shift kept me grounded, just like working out did. And damn, it was hard to feel down on a day like this.

The chiming of the Burton Tower carillon nudged me back and I started off with an easy jog again. By the time I was finished, I was soaked, breathing hard, and had a solid runner's high.

***

On the way back to South Hall, my phone buzzed. Tinder notifications. I checked with a suddenly elevated heartrate, but felt let down that none of them were SensualSiren -- just a few lesser pumas that'd had swiped right on me. I flirted with them but disappointingly, none of the convos went anywhere.

My day, which had started out with such crazy promise, settled back into tedious normalcy. Later that afternoon I sat through Communication 240: Introduction to Media Studies, another lecture course, but way less hellish than English 102. After hanging out with friends, I found myself right back in my room again, late, listening to music in a tank top and boxers. I was hunched up at my desk, trying to rework the topic for my upcoming Thompson paper so it sounded enough like me and less like ChatGPT to pass scrutiny. Printed notes from the required readings on Freud were strewn around my laptop, highlighted in orange. I hadn't gotten far.

"Oedipus: A Literal Motherfucker" obviously didn't fly. Neither did "The Psychoanalytic Undertones of Literary Freudianism" or "Why Freud is Full of Shit: How Freud Got Everything Wrong" or "How Freud Went Full-on Narcissistic Rage with His Mother and Father". I was stuck.

'...I'm so high at the moment

I'm so caught up in this

Yeah, we're just young, dumb and broke

But we still got love to give

While we're young dumb

Young, young dumb and broke...'

"Fuck," I grumbled, tossing my mechanical pencil aside and stretching out my hand. My brain felt fried.

My phone vibrated and the Tinder notification bell chimed.

It's a Match! You and SensualSiren have liked each other.

Oh shit, this was it. The fuckin' summa cum laude of MILFs! Okay. Okay... I'd make the first move. I steadied myself and swiped open the app to click 'Send a Message'.

[Aaron: Hey there, gorgeous.]

5 minutes later, she messaged me back.

[SensualSiren: Hi handsome.]

[Aaron: Your profile's super hot, babe.]

[SensualSiren: So is yours, stud. You're so sexy. I love your body, and that smile? I can't stop thinking about you.]

[Aaron: Glad I have an effect on you ;)]

[SensualSiren: I bet. When do I get to see the rest of that cute face of yours?]

[Aaron: When you show me yours, baby.]

[SensualSiren: Touche. Let's just take that part slow, shall we?]

[Aaron: Yeah, sure thing, I feel the same way.]

[SensualSiren: That's very sweet of you.]

[Aaron: No problem, baby. Can't wait to get to know you better.]

I took the phone back to my bed and reclined against the headboard. I was already hard just talking to her.

[SensualSiren: I look forward to it. So, what's your major, handsome? Tell me a bit about yourself.]

[Aaron: I'm at UM. Undecided, but I'm thinking about Journalism or maybe Marketing.]

[SensualSiren: What a coincidence. My son goes to UM.]

I paused, and my heartbeat picked up.

[Aaron: Does that make this weird?]

[SensualSiren: Of course not, honey. I just think it's so cute and hot. The idea of a young, handsome, athletic college guy, just like my son.]

I grinned. Damn she was one horny, filthy-minded slut.

[Aaron: You mustve had him young tho]

[SensualSiren: 19]

[Aaron: Wow, you must be super fit and have great skin if you had a kid at 19.]

[SensualSiren: 2 actually. But let's not talk about them.]

[Aaron: Sure. I can't believe you're so fit. You're crazy gorgeous. what's your secret]

[SensualSiren: Yoga, pilates, some weights here and there. Oh, and I'm a jogger now.]

My desires were starting to take over and I decided to be a little more forward.

[Aaron: Sure. truth be told I've been fantasizing about you all day]

[SensualSiren: Ohhh... Do tell. What do you think about when you touch yourself, Aaron?]

Oh fuuck. I grabbed my cock and gave it a good squeeze for relief as I started to painfully chafe against my boxers. This was getting real, fast.

[Aaron: Your beautiful mouth and tongue sucking my big dick.]

[SensualSiren: Hmmm... Interesting choice. And you have a big dick?]

[Aaron: Well I can't see your boobs or your pussy in your photos, so...]

[Aaron: and yea I do. its about 9 inches..]

She didn't reply for a couple of minutes as I began to harden even more.

[Aaron: you wanna see it?]

Her silence lasted several more minutes this time. The suspense was exhilarating, excruciating.

[SensualSiren: Yes.]

[Aaron: Okay. You're making me really hard right now.]

[SensualSiren: Mm I don't normally do this, but I really want to see.]

[Aaron: You got an email address?]

[SensualSiren: I don't think so. I don't like giving out my personal details to strangers online. It's a risk.]

[Aaron: Don't worry. Just make a new one on gmail or yahoo or something. Just for us. I can't send anything on Tindr]

Another long pause.

[SensualSiren: OK I can try. It might be a little while, though.]

[Aaron: That's ok, I need to make one too]

I made a dummy account while I waited, I felt such a secretive rush at what we were doing. I'd never fucked around like this on the Internet before, but the anonymity had made me really bold, much more than usual. We were just two consenting adults, male and female -- nothing but mammals, right? The age difference didn't matter. We were moving fast, but I didn't care. My dick was in control and I wanted to see where it'd take us.

10 minutes later, she finally replied.

[SensualSiren: Here. ]

[SensualSiren: Now show me that cock.]

[Aaron: Give me a sec.]

I sent her a photo of my fully erect, thick, veiny cock, and another shot from below, showing my muscular chest and abs.

[Aaron: That's me.]

[SensualSiren: Goodness, I wish I had that cock inside me right now. You're so beautiful, baby.]

I grinned and started slowly stroking my length.

[Aaron: Thank you, ma'am. Me too.]

[SensualSiren: You have such a nice cock, Aaron. How old are you, again?]

[Aaron: 19 almost 20]

[SensualSiren: That is SO young, honey. Your cock is so big and perfect, and you're just gorgeous. How's a woman supposed to resist?]

I started stroking myself again, and took a short video of my cock throbbing and pulsing, precum glistening as I started jacking it. I sent it to her inbox with a bite of my lip.

[Aaron: Fuck you're making me really hard. Check your email]

A minute or so later, she responded.

[SensualSiren: Ohhh wow. Is that all for me?]

[Aaron: Hell yes. All for you.]

[Aaron: I wanna see your tits babe. Your pussy. Something. Please.]

The pause was even longer now.

[Aaron: It's okay, this is all anonymous, and for what its worth I would never share it. you already have my dick lol]

[SensualSiren: Ok. Just be patient.]

I started pumping myself faster, watching her typing.

[SensualSiren: Here goes nothing.]

A few seconds later, I got an email notification. I opened it, and my breath caught in my throat.

The image showed her large, perfect teardrop breasts, taut and supple, capped with hard, puffy pink eraser-like nipples. Siren's pale flesh was very slightly veiny and looked so full. God, her tits were fucking beautiful. I could only imagine the feeling of them in my hands, the softness and the weight. My cock lurched at the sight. As I slowly pumped my shaft, my thoughts turned even more lewd. I wanted our future babies to feed at this woman's ripe, mature breasts. The photo was cropped at Siren's neck, though I could see her dark hair cascading down the front of her shoulders. She had a very fine dusting of freckles over her collarbones and upper chest that was somehow endearing.

[Aaron: Jesus your boobs are gorgeous]

[Aaron: You are so sexy]

[SensualSiren: Mmm, glad you like them.]

[Aaron: I fucking LOVE them]

[You're so sweet.]

[Aaron: can you send the full version pls ;)]

[Aaron: If not thats okay, I just want to see as much as I can]

Siren took another minute or so, then I heard the email notification.

The picture was a mirror selfie of Siren, naked, facing away, looking over her shoulder and smiling seductively at the camera, her hand in her hair, her toned, lithe feminine back, great ass, and long legs all visible. With her small waist and flared hips, SensualSiren had the perfect hourglass figure. Her dark wavy hair hung down the side of her back, and I could see a few more freckles kissing the tops of her shoulders. Her face was vexingly obscured by the phone in the selfie again, leaving just her smoky, mascara-ringed eyes.

"You've gotta be kidding me," I muttered. I couldn't believe she'd actually sent a full-body pic. Siren was so. Fucking. Hot. Her legs were slender and smooth, and her ass was tight and round. Couldn't see any cellulite. Whatever she was doing was working.

[Aaron: FUUCK you're so hot. What a body]

[SensualSiren: You're quite the flatterer, aren't you?]

[Aaron: I'm not lying. I'm so hard..Your body is incredible, you're so fucking sexy. I can't wait to have you]

[SensualSiren: My, my, aren't we impatient?]

[Aaron: Yeah well youre the hottest thing I've ever seen. I just can't help myself,, Im dying for you..]

[SensualSiren: Are you touching yourself?]

[Aaron: you wanna watch me?]

[SensualSiren: Please.]

[Aaron: OK]

I stripped and put the phone down on the bedside table, angled to the side to film just below my chin. I gripped my big cock and started pumping it hard, showing the length and the thickness like I was some kind of tribal hopeful trying to attract a mate. Displaying my strong young body, offering her a glimpse of my potency, my maleness; my promise as a lover and stud. My mostly hairless body was covered in a light sheen of sweat and I grunted through my teeth, putting on a show as I felt the tension mounting in my groin.

I kept thinking about the photo Siren'd sent of her tits and the one of her back, ass, beautiful curves and the promise of her sex. I couldn't wait to see her fully, to be with her, to feel her hot, womanly pussy enveloping my dick. My strokes got faster as my hips arched, my right hand moving down to cup my full, heavy balls. I wanted to give Siren a show.

I stifled a groan as my cock swelled even bigger. I couldn't believe this was happening, that such an incredible MILF had fallen for me and was letting me do this. Siren would be watching, fucking herself to me. The fact that I was probably her son's age and she liked that pushed me even closer to the edge. She was such a fucking wanton slut. I wanted to claim her in the most primal, bestial way. I started moaning, my breaths short, fast, ragged.