Jay Friday
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A Summer Obsession
🕑 Added 2025-03-10 18:04:58 +0000 UTCAuthor’s Note: Well, I was hoping to have Dungeon Mistress session 3 ready for you today. It's not quite there yet but should definitely be ready for next week -- it’s already at 10k words and will probably be at least as long as session 2!
Since it's not quite there yet, I’m posting a sponsored story from last month. This story was sponsored by roxas_duh. A big thank you for the support of my writing!
This story features Jason (from the Unexpected Summer series – this picks up after Ending B, to be precise) and Allie (from my stand-alone story Extra Credit). You’ll understand the story better if you’ve read those first, especially the Unexpected Summer series; there are references to that throughout. I’m still planning on writing another series involving Jason (and, duh, Summer) one day, as well as continuing Allie’s saga. This is a stand-alone interlude piece to explore a specific idea and bridge to what’s next!
—
“Fuck, Jason, yes, don’t stop…” She craned her neck around to look back at me.
I wasn’t planning on stopping. I was absolutely plowing her, both hands around her waist. She had a great ass – not too big, but round and firm. It had just enough give to bounce, hypnotically, each time I thrust into her, and I was absentmindedly watching it.
She was, by all objective standards, a great lay. Pretty face, nice body. Wet, responsive, vocal. The way she sounded as I railed her – submissive and out of control, totally overwhelmed – was undeniably hot. As I met her gaze, her eyes actually rolled back in her head a little.
But – admittedly – my mind was elsewhere.
For starters, I couldn’t remember her name, and was racking my brain for it. It began with a B, I thought. Brittany? Brianna? Bridgette? Something like that.
The first few after the breakup had been easy to remember. But after ten or fifteen – at the rate of two or three a week – it got a lot more difficult. And the most recent ones, well…there was just no way.
“Ungh, yeah, god, you’re pounding me so fucking hard,” she moaned.
I reached up and grabbed a fistful of her hair, right at the base of her neck. She let out a whimper, arching her back.
Brooke…no…Bailey, maybe?...was blonde. Almost the same shade as Jessica’s hair had been, really.
Jessica.
I pushed that thought away, guiltily.
After Jessica dumped me – and after I drove the long, fourteen-hour drive home from her family’s cabin, alone – I had moped for a week or so. She’d been my first and only serious relationship. Cheating on her, with her sister…well, it had ruined my life. Probably hers, too. It had left me in a funk.
Then I had realized that Jessica was coming home in a few days. My summer job was starting in a few days. I had to get my shit together.
I found someone looking for a roommate for the rest of summer on short notice, and moved out of the apartment I had shared with Jessica. I registered for a summer class at the university, too, figuring the more I had to keep my mind off her, the better.
That had turned out to be a good idea. I had made a few new friends through the class and the new job. I went out drinking with them. Had a drunken hookup. Then another. Then another.
I thought it’d help me get over the breakup. Over Jessica.
And – perhaps even more importantly – over Summer.
“Yeah, just use me with that big dick, it feels so good,” the young woman moaned. Barbara? She didn’t really seem like a Barbara, though...
“Yeah, you like that cock?” I grunted the words out. We had been going at it for a while. I knew – from experience, now – that much longer was probably going to start to get physically uncomfortable for her. Or she’d start to feel bad, like it was her fault she couldn’t get me off.
It wasn’t, of course. It was something wrong with me.
“Y-yessss – y-you’re such a fucking stud…” Her voice was aroused, urgent. She was panting. I could tell she was headed towards another orgasm; her third or fourth, maybe. I hadn’t kept track.
I should wrap up, I decided. I moved my hands from her waist to that round butt, one palm on each of her cheeks, and spread them, picking up the pace.
“Oh–fuck–yeah–ah–you’re gonna–ahhhh–” Her voice broke into a shriek as she started cumming, shaking hard against my legs. I held her up against the bed, hands on her ass, and fucked her through the orgasm.
But I wasn’t thinking about…Brynn? Bethany?...whatever her name was.
I was thinking about what it would be like to have Summer in front of me, in this position. Ass in my hands, cock filling her, losing control, legs shaking, incoherent after a few orgasms, totally submissive for me.
Like it always did, that thought sent me spiraling towards an orgasm in record time. It’d be so hot to have finally showed her, to have gotten Summer off. Over and over.
To have gotten even, and then some.
“Fuck yeah, Su…” I verbally stumbled over the words, almost making a mistake that this woman – whatever her name was – certainly didn’t deserve. “Y-you’re taking my cock so well…”
But she was in the throes of her own orgasm and evidently didn’t catch my near slip-up. She just let out a moaned, encouraging, “I-I love taking it…God, I want you to cum, fill me up with it, please…”
It was enough. My imagination took it and ran with it, thinking about Summer saying those words, cumming on my cock, encouraging me to cum in her.
I grunted, and thrusting hard, started cumming, visions of what it’d be like to do that with Summer filling my mind.
—
As I lay next to…well, whoever this was, contentedly curled up against me, I decided I had to acknowledge a fundamental truth.
I wasn’t getting over Summer. If the first ten hadn’t done it, and the second ten hadn’t done it, I doubted that thirty, forty, or fifty would be the magic number that somehow got her out of my head.
That just prompted the usual tidal wave of guilt. What the fuck was wrong with me? Why was I struggling to get over Summer, but not Jessica? Summer was the reason I’d broken up with Jessica. Instead of mourning the wreckage of my relationship with my girlfriend, the woman I’d imagined proposing to, building a life with…well, I was thinking about Summer’s big tits, her smirk, the way she’d always seemed to know just how to get me off…
I sighed. It was a very familiar spiral of thoughts at this point, and left me feeling guilty and humiliated at the end of it. I didn’t know how to escape it.
The woman in bed next to me misunderstood the sigh.
“Mmm, I know, right? Jason, for what I thought was just going to be a casual drunken hookup, I didn’t expect…” She trailed off, sighing too. Hers was a dreamy, satisfied, blissful sigh.
I winced. “Yeah, uh…you were amazing.” I wished I could remember her name.
She hesitated, and then, looking me in the eyes hopefully, said, “Would you ever want to…y’know…like…hang out, maybe? I’ve never…nobody’s ever…that was…well, it was really good.”
Shit. I could tell she was really putting herself out there – which always made letting them down harder.
“I mean, I didn’t, uh expect this either…I’d like to…think about it.” Then I had what, for me, passed as a minor stroke of brilliance. “But why don’t you put your number in my phone? I’ll text you.”
She looked crushed, but took my phone and put her name and number in, handing it back to me. I looked at the phone, glad to finally have some help with her name.
Sydney.
I hadn’t even been close.
“Thanks, Sydney. Look, this was incredible. But I’ve gotta run. I wasn’t expecting this either tonight y’know? And I’ve got a summer class early…look, I’ll text you!”
Sydney was disappointed. One more reason to feel guilty.
I dressed and left as quickly as I could.
—
Back at my apartment, I decided that the problem was this: none of the women I’d found were challenging enough.
The challenge of the chase was always fun – the flirting, the innuendo, the charged lines about what I’d do to them, their jokes about whether I could really deliver, what they’d do to me. But once I had them alone and we started getting physical – well, I don’t mean to brag, but I was a tall guy. I had Captain-America good looks. I was in increasingly good shape after the breakup; the gym was helping to keep the dark thoughts away. And I was well-endowed.
So invariably, once we were alone, the flirty banter and charged jokes subsided. The women were all intimidated, enthralled, or both. There was never any question about whether I’d deliver in their minds, anymore.
And I generally did deliver.
And I liked delivering. But I also liked feeling…challenged. Seduced. I wanted to try to resist. I wanted to fail to resist, to lose control of myself. I wanted someone who brought that out in me.
Someone like Summer.
This all felt too boring, too easy, compared to what Summer had put me through.
I sighed, and went to take a shower.
—
“C’mon, man, stop moping. It’s gonna be fun, as long as we get the ratio of men to women right and it’s not a sausagefest,” Blake said. “And you know lots of girls, so just get a few to show up.”
I rolled my eyes. “Blake, the only girls I know are Jessica’s friends – all of whom have blocked me – and girls I’ve hooked up with, who want to keep dating me. I don’t want to invite any of them to our party, let alone to put them all in the same room.”
Blake – my new roommate for the summer – had insisted we throw a party this upcoming weekend. It was, admittedly, a good idea; we both knew lots of people, the summer was halfway over at this point, and the pickings were slim if you wanted a good party.
Blake laughed. “Okay, you framed that in the douchiest way possible, but I get what you’re saying. Tell you what – invite one girl you’ve hooked up with, but don’t want to date. I’ll invite one girl I’ve hooked up with, but don’t want to date. That’s fair; whether they show up or not, at least we both tried.”
I liked Blake; I’d been lucky to get to room with him for the summer. He was at the school on a football scholarship, a friendly, easygoing jock. And – more importantly given how I was spending my summer – he wasn’t threatened or annoyed by my sexual escapades, the endless parade of girls I’d had in for one-night-stands and drunken hookups over the course of the summer. He had his own stream of women passing through his bedroom, too.
And his suggestion had some merits. I composed a text letting Sydney down easy – I had lots of variations on the same text: she’d been amazing and wonderful but I wasn’t really ready for a new relationship, my last relationship had just ended, I was caught up in my own head, but I didn’t want things to be weird between us and she was more than welcome to come to a party at my place on Friday night.
I pushed send, then held my phone up for Blake to read it as proof.
Blake read the message, shaking his head and laughing. “Man, you use way too many words. That’s totally getting screenshotted and sent to a girls’ group chat to be endlessly overanalyzed. There are only one of two outcomes: you get blocked, or you come home from class one day to find out she’s moved into your apartment because she’s decided you’re soulmates and she can fix you. You gotta go simpler.” He flipped his phone around to me.
His message was a lot simpler: Hey, I’m hosting a party on Friday night, you should come. You can meet my new roommate, I think you’d like him.
I blinked. It was to someone saved in his phone as Allie. “Are you trying to set me up with her?” I asked him, suspiciously.
He laughed, shaking his head. “Nah. I mean, you’re welcome to try. But if you asked me, I’d recommend against it. I know a couple guys who have tried dating her; it never ends well. But she likes meeting new people; I just thought it’d help get her to show. You think I’ve got a shot with Sydney?”
I considered, then shrugged. “Dunno. Happy to put in a good word for you if she comes, though, man.”
He clapped me on the shoulder. “That’s what I’m talkin’ about. C’mon, let’s go do the booze run so we’re stocked up.”
—
As it turned out, I didn’t hear from Sydney. And when I messaged her again, she had blocked me.
As Friday rolled around, Blake was only mildly disappointed. “Told you so. Too bad, ah well. Always more fish in the sea, buddy.”
I sighed. I wished I had Blake’s laissez faire attitude when it came to Summer.
—
Friday evening. All the booze was cold. One of Blake’s buddies had brought a sound system over to our place. Blake’s musical tastes and mine differed, to say the least, and the playlist he showed me, grinning, made that very apparent.
“...Can’t the playlist have something that’s not country on it?”
“Absolutely not.” Blake was emphatic. “Country music consists exclusively of songs sung by men about how they’re obsessed with women, and songs sung by women who are getting revenge on men. Chicks love both. It’s like catnip. It’s perfect for a party where the two of us are trying to get laid!”
I opened my mouth, not sure whether to argue with his characterization of country music or the idea that I was trying to get laid tonight. But I decided arguing with him on either point was a fool’s errand, closed my mouth, and shrugged. I cracked a beer, chatting with him over the next half-hour as people trickled in.
I’m not trying to get laid tonight, I told myself, firmly, thinking about Sydney. Getting laid wasn’t helping me get over Summer. Having sex with women when my head and heart weren’t in it just made me feel guilty for a whole different set of reasons.
I tried to focus on having a good time, talking with Blake and a few of our friends, cracking jokes and laughing.
At least the consensus about music seemed to be on my side. Blake’s firmly held beliefs about country music came up again almost immediately when someone asked if we could put on anything else. Blake was adamant.
“Blake, c’mon, all country music written by men isn’t about obsessing over a woman, that’s all I’m saying,” I said. There were several nods of agreement.
“It is,” Blake said, amiably but decisively.
“What about Friends in Low Places?” one of his friends protested. “It’s about friends!”
I winced. “I mean, that song’s about a guy crashing his ex’s wedding. ‘I showed up in boots and ruined your black tie affair?’ That one is in Blake’s favor.”
As we talked about it, Wagon Wheel – the Darius Rucker version – came on.
A girl in the group – one of his buddy’s girlfriends, I thought – chimed in. “Hey, what about Wagon Wheel? That one’s just about some guy hitchhiking.”
I shook my head ruefully. “It’s a guy hitchhiking across the east coast to see his girlfriend and have sex with her.” I paused, while the lyrics played. “C’mon, ‘rock me mama like a southbound train’? The mama in question is not his mother. The guy’s obsessed. You’re all just proving his point.”
Everybody laughed, and Blake clapped me on the shoulder. “See?”
“Look, it’s just a common theme, dude, not every song.” I said, in mock irritation. I was enjoying the conversation.
A woman’s voice – a little hesitant, from outside our little circle of conversation – said, “I mean, at the end of the day most people end up obsessed with somebody, don’t they? Like, the one that got away, or the one they couldn’t have, or…whatever.”
Blake glanced over at her and broke out into a friendly grin, stepping to the side to make room for her. “Hey, Allie. Good to see you.”
She looked a little hesitant, but joined the conversation. “Hi, Blake. Thanks for inviting me.” He gave her a little side hug.
She smiled around the group.
Allie was small, petite – shorter than me by more than foot, I’d guess. Pretty face, with long, dark-blonde hair. Olive skin.
Her height, slim frame, and delicate, feminine features combined to give her an almost elfin impression…except for her tits. They were big, especially on that small frame. She was wearing jeans and a tight scoop neck t-shirt that was doing its very best to contain them; her tits swelled against the fabric of the top, creating several inches of deep cleavage.
The contrast between her breasts and her frame was distracting. I was staring, I knew, but that had to be a reaction she was used to. She was hot as hell.
Although she wasn’t behaving like a young woman who knew she was hot. She looked anxious and uncomfortable, if I was honest. And it was a little curious: some of the other people in the group, men and women alike, avoided eye contact with her. There was obviously some dynamic I was missing. I’d have to ask Blake about it.
The reception she was getting reminded me, immediately, of how many of my and Jessica’s mutual friends had turned out to be exclusively Jessica’s friends, in the end.
I decided that I didn’t have any problems with Allie, and I was going to be friendly.
“Hi, I’m Jason.” I gave her a smile.
“Allie.” She shook my hand hesitantly, timidly. Was that a flicker of recognition at my name? I wasn’t sure.
“Well, to your point Allie, maybe I could agree with an amended version of Blake’s theory. Maybe the few country musicians who haven’t yet written a song about being obsessed with a woman just haven’t found the right woman yet.”
“Could be,” she said. She broke into a grateful smile. Blake nodded along, pleased to see some detente being reached.
The ice broken, the group chatter moved on to other topics, people getting progressively drunker. But I could see that Allie continued to get a bit of an icy reception, and my curiosity was piqued. At one point, Blake pulled away to grab another round of beers for people, and I joined him.
“What’s the deal with Allie?” I said, frankly, the moment we were out of earshot.
“Those tits, huh? Sexy, am I right?” This was now the three-beers-deep version of Blake: still perpetually jovial, but without any filter at all.
“Yeah, but that’s not what I’m asking about. Why are people giving her the cold shoulder?”
He shrugged. “Well, she’s got history with most of the guys – including me. And none of them worked out. And some of them were kind of, uh, spectacularly embarrassing hookups and breakups. It doesn’t bother me, but some of the other guys…”
I waited for him to elaborate.
He didn’t.
“...So why are the girls giving her the cold shoulder too?”
He shrugged. “Ah, y’know. I think they just don’t like that the guys they’re dating have been with a girl with tits like Allie’s. Here, you carry these.”
He handed me a few beers from out of the fridge and started making his way back towards his friends.
I felt a renewed pang of sympathy for Allie. Spectacularly embarrassing hookups and breakups described the situation I was going through with Summer and Jessica pretty well. And she was hot. I was intrigued.
But I definitely wasn’t trying to get laid, I told myself. Firmly.
I was trying to solve a mystery.
—
I didn’t get the chance to talk with Allie one-on-one for a while, but I pounced on the first opportunity I saw, catching her as she was grabbing another beer from the fridge.
“Hey. Having a good time?” I gave her my best smile.
She nodded. “I’m, uh, not really a party girl, but this has been okay, yeah.”
“So how do you know Blake?” I was curious how she’d present their relationship.
“Oh, me and him and some of the other guys here all had a class together last year,” she said, vaguely.
I nodded. She didn’t give away anything there. I decided to be more direct. “Y’know, earlier, when you were talking about how men always end up obsessed with one woman…were you speaking from personal experience or just general observations?”
She flushed a deep crimson. “N-no…well, I don’t know…I just feel like—” she stammered the words out.
I laughed, trying to keep it gentle. “Relax, Allie. Just curious.”
She smiled, looking up at me. “Some of my friends have talked about you, you know.”
I raised an eyebrow. “Oh? What have they said?” I had gotten this kind of response a few times over the course of the summer. The answer was invariably that I was a cheating piece of shit (if they were Jessica’s friends), or that I was great in bed (if they weren’t).
She hesitated as one of Blake’s friends walked past; the girlfriend of one of his buddies. She smiled politely at me, but gave Allie a withering glare as she walked past.
I decided not to let her answer. “...And what would Blake’s friends say, if I asked them about you?”
Allie winced. She was watching that other woman walk away. “Can we…talk someplace more private?”
Not trying to get laid, I mentally repeated, firmly.
But she looked good. And I was too curious not to.
—
I led Allie into my bedroom. Blake made significant eye contact with me, but I just shrugged. He gave me a thumbs-up back.
Most other people didn’t notice.
I shut the door, muting the sounds of the party outside. She sat down on the edge of my bed; I sat down in my desk chair, turning it to face her.
“So, c’mon, I’m curious. Things are obviously super weird between you and most of Blake’s friends. What’s up?”
She sighed. “Well, I’ve…hooked up with a bunch of the guys here.”
I shrugged. “So what? I mean, the girls I’ve hooked up with aren’t here. But there are a bunch of them, trust me. I’m sure Blake’s hooked up with a bunch of the ladies in the room, hasn’t he?”
She nodded, slowly. “Yeah, but…you don’t get it…it’s not the hookups, it’s, um…how they ended.”
I laughed. “How they ended? What, do you take a finger from each of them as a trophy or something?”
She giggled – a shy, musical sound. “No.”
“So what, then?”
“They…um…guys tend to…finish fast, with me. Like really fast. They’re always, y’know, a bit humiliated, I think. They avoid me, after.”
I froze. It was – I couldn’t help thinking it – exactly the kind of thing that Summer might say. She’d say it more confidently, of course, but…
The effect on me was instantaneous. It was like I was transported. My face reddened. I could feel the blood surging to my cock. My eyes were drawn to Allie’s cleavage, imagining why guys might finish fast. She was so petite, too; probably tight…
But Allie’s voice was embarrassed, not Summer’s confident, smirking tone. I tried to pull myself together. “Uh…how is that your problem? Or fault?”
Allie shrugged. “Well, I think they last a lot longer with other girls, so it must be me, right?” Her voice was a little bitter.
Comprehension dawned on me. “Ah. So that’s why the other girls here don’t like you, either?”
She nodded, glum. “Yeah, it started with just the guys talking to each other about me, but eventually, the girls found out, too. And I mean, I get it. Would you want to know that somebody else your partner hooked up with finished them off way faster? I wouldn’t. Especially if everyone else knew it, too.”
I flushed and looked away for a minute. That had been what had pissed off Jessica, more than anything, I knew. She hadn’t said it specifically, but I could tell that at the end of the day, that was the real dealbreaker: that Summer had been making me cum so much more easily than Jessica did.
I sat in silence for a minute. I could feel my cock straining against my jeans now, too. Allie was hot – but it was mostly the conversation, the way it reminded me of Summer.
And that reminded me of something else Allie had said. It wasn’t a change of subject exactly, but it was better than silence. “So. What are your friends saying about me?”
“Well…a few girls I know are talking about how you cheated on your girlfriend – ex-girlfriend, sorry – with her sister on a family vacation. They think it’s pretty fucked up.” Allie’s voice was matter-of-fact. “The rest are all saying that you’re incredible in bed, though.”
It was exactly what I had expected. But the stark description – cheated on your girlfriend with her sister on a family vacation – was the first time I’d heard anyone say it out loud, to my face. It felt like a slap.
I don’t know what my expression was, but it must’ve been bad, because she winced. “Sorry, sorry. You asked, but I can be too blunt. That was stupid. I don’t even know if that’s what actually happened.”
I blew out a breath. “It…it is what happened. And it’s fine, I just…didn’t think of myself as that kind of person. And then suddenly I was that kind of person. It…” I shrugged, uncomfortably. “It was really fucked up of me.”
She looked curious. “So…why’d you do it, then?”
I shifted uncomfortably. “I don’t really know. She…well, she got under my skin, at first. Teasing me, and stuff. And then after that, I just felt…totally out of control. Like I couldn’t stop.”
She mulled that over for a moment. “You asked me if my comment about how men always end up obsessed with one woman was from personal experience. Then you agreed with it…” she hesitated, and then leaned forward. “Do you think you were obsessed with her?”
“...I don’t know, maybe, I guess?” I tried to keep eye contact with her, but the way she was leaning forward, though, gave me an excellent view of her big tits. “Why are you asking this stuff, anyway?”
“Sorry if it’s too personal. I…don’t really talk about this stuff with anybody. I don’t have many close friends, really. Just…well. Guys who’ve blown their loads too quick, and girls who hate me because they think I was the best their boyfriend ever had. All of them are embarrassed by me, or resent me, or both.”
I felt a little sorry for her. “So it sounds like everybody is a little obsessed with you,” I said, teasingly.
She blushed, attractively. The blush traveled surprisingly far down her chest, and my gaze followed it.
“Well, the way the girls I know are talking, they’re all a little obsessed with you,” she fired back.
I laughed, and we were both silent for a moment – a companionable silence, this time. I finally broke the silence, curious. “So what’re they saying, exactly?”
She waved a hand. “The usual gossip between women, y’know. You’ve…” she giggled again, still blushing, “...that got a huge dick and you can last for hours.”
Her gaze wandered down to my jeans, and then locked on there. I was sure my erection was obviously visible.
“I mean, I dunno about hours,” I said.
And then I thought about Summer. How fast I’d been for her. “And it…depends on the girl, I guess,” I amended, feeling a little embarrassed.
“Mmm.” Allie was still staring, didn’t react to what I had said.
Not trying to get laid.
Screw it. I liked Allie. This had been one of the first real conversations, real connections I’d had with another person since…well, everything that had happened with Summer.
And she was undeniably hot.
I reached out, across the gap between us, and ran a knuckle up – from just above the swell of her breasts, up her neck, and to her chin, gently turning her head up, pulling her gaze up to mine.
“What if we did a little experiment?” My voice was barely a whisper. “Y’know, you can see if the girls were right about me…and I can tell you if you’re really better than them.”
She bit her lip, meeting my eyes.
Then she nodded. “I’d…yeah, let’s…”
But she trailed off into a soft sigh as I brought my hands to her tits, caressing them. The scoop neck left enough smooth, tanned bare skin across the tops of her breasts for my fingers to graze over, even as I palmed their full weight in my hands.
They were enormous – far more than a handful – and soft, full in my hands as I squeezed and fondled them.
Fuck. I pulled her into my lap in the chair, and put my mouth on her neck, kissing down towards her chest, my hands still roaming over her breasts.
After a moment, Allie let out a soft, shuddering breath. “God, that feels good,” she mumbled. I felt one of her hands cup the back of my head, as I kissed my way down past her clavicle. Her other hand snaked down between my thighs, palming my length. “Mmm,” she moaned.
I had arrived at her tits – I was squeezing them and kissing the tops of her breasts simultaneously, now. Although my kissing was devolving to just pressing my entire face against and between her tits.
I looked up at her, a wry smile on my face. “I believe I’ve identified the area where some guys may run into trouble. God damn, Allie.”
She giggled. “You had better take a closer look, then, huh?” She pulled her top off over her head, leaving just her bra.
I stared, openmouthed. She had a flawlessly even natural tan. The bra was woefully overmatched – I didn’t think it was intended to be a sexy push-up bra, but there was nowhere else for big tits like hers to go, besides up and together. Her cleavage was impossibly deep. I could see – just peeking out from under the cups of the bra – a hint of her aerolae, a darker brown against her tan skin.
“You can take a break if you want,” Allie said. She sounded…concerned, I realized.
“Terrible idea. I have never wanted anything less than that,” I responded, immediately. I kept squeezing her tits, thumbing over her nipples in the bra cups.
“Oh…okay…it’s just that, some guys, y’know…finish about now…” she sounded surprised, pleased.
Well, that was a nice shot in the arm for my ego. “Guess I’m not some guys.”
“Those girls certainly weren’t wrong about your size…” as she spoke, she palmed my length through my pants again.
“Lemme get you out,” she whispered. She slid down between my legs.
I leaned back in the chair as she undid my pants, slipping them down around my ankles, and then pausing at my boxers, biting her lip and staring at the enormous tent my erection was forming, tipped with a dark stain from the precum. “I like the way your bulge looks.” She said it like she was confessing a dirty secret. “It looks, y’know, really excited.”
The comment sent me reeling back into a very specific memory. There was something in the way she said the word excited, on her knees between my legs, that reminded me of the last titfuck I’d gotten – Summer, by the pool, my girlfriend inside with her parents…
My cock didn’t just twitch, it lurched at the memory. Allie pulled my boxers down and out of the way, staring at my dick.
She looked up at me. “Can I…”
I didn’t know what she was asking about, specifically. And I wasn’t sure I cared. I just nodded, enthusiastically.
“The guys pretty much all want this…so I’ve got lots of practice…” As she spoke, she lifted the band of her bra, so that my cock – slick with precum – slid up the smooth skin of her tits.
I was frozen, mouth agape.
It wasn’t just the sensation – which admittedly was incredible, intense. My cock, slick with precum, was under the band of her bra, sliding between her tits. The bra created tight, deep cleavage, applying even pressure on my length.
There was something else, though. Maybe it was how petite she looked, the contrast between her frame and the size of her breasts wrapped around my girth. Maybe it was the expression on her face, an odd cocktail of curiosity and arousal, or the way she was using her small hands to try to push her tits together even more. Whatever it was, the erotic sight made the sensation all the more powerful.
And on top of that, it was what she was saying, again. Lots of practice. Summer had said something very similar. I felt my cock twitch, again. I closed my eyes, trying to keep my breathing even. I felt a strange mix of helplessness, guilt, and…excitement.
That sensation of being out of control, a powerlessness – something I’d come to associate exclusively with Summer – was mounting. And I liked it.
"Fuck, you feel amazing," I groaned. I felt my cock twitch between her tits.
“Ever done this before?” Allie asked the question, curiosity in her voice as she looked down at my cock and rocked her cleavage down further on it. I felt her bra brush against the tops of my thighs.
God. Summer had asked the same thing. I just nodded, feeling the climax growing in my balls. “Not, uh…like this, though…” I moaned the words out, trying to get a handle on my arousal.
Even with most of my length totally enveloped between her breasts, the head of my cock was poking out from her cleavage. She stared at it.
“I like how big it is,” she whispered. “Most guys just kind of disappear between them, but you…” She watched as she started to move her tits up and down, rhythmically, the head of my cock thrusting in and out from between her tits.
She was better at this than Summer, even. The thought came with an accompanying sense of helplessness as her tits smoothly pumped along my thick shaft.
And I hadn’t lasted long for Summer.
“I-I guess I’m not most guys either, huh…” But there was less confidence in my voice now; it was the same line I had just used. Having my cock crushed between her breasts, the soft, slick feel of skin enveloping my length, was overwhelming. I tried to keep my breathing even.
Allie pulled her gaze off my cock, looked up at me. “Yeah, you really aren’t. Honestly, most guys have cum by now…”
I could see why. I groaned and closed my eyes. I wasn’t sure if she was doing it on purpose – Allie certainly looked guileless – but ultimately it didn’t matter. She was incredible at this. I could feel the control I usually had, that I’d had with every woman since Summer, just spiralling away.
I let out a moan. “I can–mmm–see why…”
She in turn, let out a little giggle. “God. The other girls really were right. I never get to do it for this for this long with anybody…”
Her comment didn’t boost my ego this time. I fought with myself, tried to resist the urge to cum.
But I must not have shown it on my face, because she looked slightly impressed. “Well, I’ll keep going, and we can see how long you can last…”
Summer had said almost the same thing.
And then she looked down at my cock again, watching as she slid her tits up and down its length. “Big dick like this, I bet you cum a lot, huh?” She was breathless – maybe from exertions of moving herself on my length, maybe from the excitement – but she kept her movements smooth, fast and even.
I didn’t think it was on purpose, but what she was saying, the sensations, my loss of control, it all reminded me so much of Summer.
Allie’s big tits felt incredible, were milking the cum out of me inexorably.
“So how long did you last with, um, your girlfriend’s sister?” She sounded curious.
I couldn’t handle it.
I managed to get out a strangled, “Allie – fuck –”
…And then the orgasm overwhelmed me.
I bucked my hips, thrusting my cock up between her cleavage one last time. The first gout of cum splashed up along her neck and chin. Rope after rope sprayed out, coating her neck all the way down to her tits.
She watched, silent and openmouthed, as I completely lost control all over her. For a moment, there was silence in the room.
Embarrassed, breathing hard, I said, “I, uh…that was…” I didn’t know what to say. I was reeling. “...You can, um clean up…in the bathroom, if you want,” I finished, lamely.
She nodded, and extricated my cock from under her bra. She grabbed her shirt and went into the bathroom. I sat, slowly pulling my pants up.
“Allie…that was…” I felt weird, out of place as I pulled my boxers and pants back up. A familiar sense of embarrassment; the way I’d always felt after Summer had made me lose control incredibly quickly.
Awkwardly, I picked up the phone to check the time.
I realized I had a few unread messages, from a new number; one that wasn’t saved in my phone. Moving automatically, I pulled the messages up, preparing to delete what I figured was probably just spam.
Then I froze.
Hey, Jason. Got your number out of my sister’s phone. It was easy to find: it’s the only number on her block list.
Anyway, I still think about you pretty often. I was wondering if you wanted to come visit me at college. We could have some fun.
After all, you owe me one. More than one, really.
My heart was suddenly pounding.
Allie poked her head back out of the bathroom. “That was hot. You really did last longer than guys usually do.”
“I, uh, thanks…” I said, distractedly. I was staring at the message, trying to decide what to say.
“...So would you want to do it again sometime?” Allie asked the question tentatively.
I glanced up at her, feeling guilty. A few texts from Summer and I was ignoring girls right in front of me. “I, uh…I would, Allie, yeah. I really would. I…I have to deal with this, though.” I gestured at the phone. “Sorry. Why don’t you head back out to the party and I’ll be out in a minute?”
Allie clearly read this as an excuse. She looked crestfallen, but nodded. She slipped back out of the bedroom door, closing it behind her.
I knew I was being abrupt. I felt bad. But the need to focus on this, to reply, was all-consuming.
I had a reply half-typed out, and then I realized something. How did I even know this was Summer? For all I knew, Jessica had given my number to one of her friends, and this was just an opportunity to fuck with me.
I deleted the reply, and typed in a very different, shorter one, asking who it was.
But after a moment’s hesitation, I deleted that one too.
Let’s say it really was Summer. Was I really going to respond to this?
This woman had ruined my relationship. Was still ruining my sex life.
I had just been with one of the hottest women I’d ever met, clearly had good rapport with her.
And Summer might as well have been in the room there with us, watching me orgasm with a smirk on her face. Making sure I couldn’t really connect with Allie.
I sighed, and put my phone down without sending anything. I lay on my bed, staring up at the ceiling, for a long time before I went back out to the party.
—
“I don’t mind driving you back.”
It was the wee hours of the morning. Only a handful of people were left, the stragglers, and Allie had just announced she was going to head out.
I wasn’t sure if she had been avoiding me or if she’d just decided to settle in to the group conversation, but either way, I hadn’t had a chance to talk to her, to apologize, and I definitely owed her an apology.
Blake gave me a knowing look. “You sure, dude? We can call her a ride instead.”
I nodded firmly. “Yeah, I’m good to drive, man. And I really don’t mind, it’s a nice night, and it’s super late, nobody should be walking home alone at this point.”
Allie looked surprised. “Hey, thanks Jason. That’d be great.”
We were quiet as we took the elevator down from our apartment to the parking garage. I held the door open for her, and she got inside. I handed her my phone and she put her address in to the mapping program. She was close by – only a few minutes away, driving.
As I started the engine, Allie mumbled, “You don’t have to do this, you know.”
“Do what?”
“Be so nice. I mean, I saw your face afterwards…you, um…looked embarrassed. And then you didn’t want to talk to me. Just like always happens.” She wasn’t making eye contact. “But I’m used to it, you don’t have to like…pretend, or whatever.”
I shifted in the seat, uncomfortably, as I turned out of the parking garage. “Sorry. It’s not you.”
That sounded lame without any further explanation, so after another moment of silence, I took a deep breath, and said, “Um…my ex-girlfriend’s sister…the one I cheated with…she texted me. That’s what I was looking at on my phone.”
Allie winced, sympathetically. “Oh. Wow. What’s her name?”
“Summer.” I could hear the frustration and confusion in my own voice.
She was silent for a moment, and then, “...So did you reply to Summer?”
I shook my head, and sighed. “I was going to, but I didn’t. I don’t know what to do. Talking to her doesn’t seem like a good idea. I don’t really want to see her, but…”
“But what?” Allie was curious.
“But…well. Remember how you asked me if I had been obsessed with her?”
Allie nodded.
“I think I still am. I think about her…well. Way too much.” I felt embarrassed, saying it out loud – but I also felt a sense of relief. It was nice to talk about it with someone.
Allie sat in silence for a while, mulling this over. I stole glances at her.
A few more turns and I pulled on to her street.
She glanced up at me. “So why do you think you haven’t gotten over Summer?”
I threw a hand up in exasperation. “I…I don’t know. She fucked up my life, but what we did was…hot.” I felt guilty, saying it, but it was true.
I stopped the car, parking outside her house, and looked over at her.
She was small, sitting there in the dim light. She somehow looked both forlorn and concerned. She looked up at me.
“...Jason, d’you want to come in? My roommates are both out of town until classes start again.”
I ran a hand through my hair. “I don’t know, Allie. I’m all fucked up.”
“I know you are. Me too.” Her voice was forlorn. “So I get it. See ya, Jason. Thanks for the ride.”
She got out of the car, started walking towards her front door.
I sat in the car, watching her.
Just like earlier, Summer might as well have been right there with me, sitting in the backseat of the car watching Allie walk away. I knew the smile she’d have on her face as I sat there, doing nothing.
Fuck that.
I opened the door, stood up, and started after Allie. She turned, surprised, at the sound.
“Changed my mind,” I said, forcing cheerfulness into my voice. “I’d love to come inside. After all – I feel like I owe you one from earlier.” The phrase – one Summer had used frequently – flew automatically off my tongue before I could stop myself.
Allie looked gratified, gave me a surprised smile. “I’d…I’d like that.” She fumbled with her keys, opened her front door, and we went inside.
I didn’t know whether I was bringing Summer in with me. I hoped she’d stayed in the car.
—
The next thirty seconds were a blur. Once the door was closed, she turned to face me, expectant – I pinned her against the wall, kissing her. She moaned into my mouth. I picked her up. She was light, delicate, almost insubstantial in my arms.
“Upstairs, on your right,” she whispered, breathlessly into my ear.
I carried her up the stairs, through a door, and dumped her onto what I hoped was her bed, because there was no stopping me now. I fell on top of her, and she made a pleased, half-gasp, half-grunt at my weight falling on her.
My hands were fondling her breasts again, kneading them as I kissed at her neck. She was panting, and her hands were everywhere – on my shoulders, sliding down my sides, scrabbling with my belt buckle.
“You have way too many clothes on,” Allie murmured.
I smiled at that. We both started frantically undressing. As I finished, pulling my boxers off, I looked down at her again – and froze, staring.
Her skin – all over – was that same smooth olive tone. Her naked tits were enormous – spilling out and to the sides, with her on her back – and topped with full, brown areola and slightly darker nipples. They were proudly erect, just begging to be played with.
“Fuck, Allie.” I stared, reverently.
Her eyes were still locked on my full, rock-hard erection.
“I want you in me.” The words were an urgent, needy, submissive whisper. Her hands were on my hips, trying to shift me into the right position.
I didn’t need to be told twice. I positioned myself between her thighs, lined myself up with her entrance, and slowly rubbed the head of my cock against her.
The view – my thick length contrasted against her petite waist
She whimpered. “Please.”
Slowly, I started pushing the head of my cock inside her, parting her folds. She was a small woman, and while she was wet, I could feel the tight grip of her body resisting my intrusion. “I, uh…I’m gonna go slow.”
“G-god–” she let out a moan, looking down at my thick length beginning to impale her. The way she felt, slick and hot around the head of my cock, was already incredible.
“Sorry…” I paused, trying to be patient. To be honest, I was grateful for the reprieve. She felt incredible, and I wanted to make this last.
“No, it…it feels great,” Allie said. I could hear the wanton arousal in her voice. “I want you to keep going.”
"Okay.” I took a deep breath, and, trying to be gentle, I worked my cock in further. It took real, thrusting effort; I could feel her body yielding around my girth, but only reluctantly. The sensation as I squeezed my thick length into her wet embrace was intense. “Fuck, you’re so tight,” I moaned.
Allie clenched her eyes shut, fingers digging into his shoulders. "A–ahh—you're so big," she whimpered.
I reached down, fondling one of her breasts, feeling its soft weight in my hand. She gasped as my palm grazed her nipple.
“You’re stretching me, i-it feels so good…” she was panting now. Her eyes met mine, desperate, out of control. “Don’t stop, please.”
I knew that look from having seen it on the faces of a dozen women over the course of the summer. She was getting close, I realized, with astonishment.
I looked down at her on the bed, halfway impaled down the length of my thick cock. I knew I was big, probably much bigger than average, but with me over her, my large frame dwarfing her petite body, my cock looked absolutely massive.
And she was getting close, even though I wasn't even all the way in her, yet.
It was the most dominant and powerful I’d felt in my entire life. I reveled in it. With a grunt, I scooped her up, moved her effortlessly to put her up against the wall.
And then, I let gravity do the rest. I supported most of her weight, but I could feel her slowly, inexorably, slipping down further and further onto my thick shaft.
She gasped, wrapping her legs around behind my waist.. “Oh, fuck, Jason, yes–”
The words dissolved into a low moan. I could feel her…not shaking, exactly, not yet, but her body was taut, trembling, like a bowstring pulled all the way back.
I wondered if she’d cum in a single stroke, just from having me all the way inside her. Just the way I had, with…
I tried to rerail the thought, but it was too late.
It was the position she was in. Her in my arms, pinned up against the wall – and the feel of her full breasts against my chest.
It all reminded me of Summer.
“Fuck, fuck, fuck,” I muttered. I froze, holding still, supporting her weight again, keeping her from sinking further down on my cock.
My own orgasm was suddenly right there. I was about to cum. Just like I had in the shower with Summer.
“Nnn…Keep going, I-I’m so close…” Allie moaned the words out.
She squirmed in my arms, trying to force herself down further on me, but I was much stronger than she was, and – even preoccupied with fending off the orgasm that was threatening to overwhelm me – I held her still.
“C’mon, Jason, fuck me.” There was a frustration in her voice, now, that I could hear.
The frustration reminded me of Summer, too, wanting to get off – but needing just a bit more than I could deliver.
“Fuck me the way you used to fuck Summer,” she whispered, in my ear.
It was too much. I couldn’t stop myself.
I started fucking her exactly the way I used to fuck Summer.
Which is to say that I moaned, crushing Allie up against the wall, thrust the rest of my thick length inside her, and started cumming.
As I lost control, Allie moaned as well. She was so tight around me that I had no doubt she could feel each pulse of my cock throbbing inside her as the orgasm swept over me. The moan was one of pleasure…but I could tell it wasn’t getting her off, and I wasn’t in control of myself anymore to do anything else. I just kept pumping the final few inches of my cock in and out of her as I orgasmed.
I stood there, panting, as the bliss faded, with her in my arms for another moment, before I moved us both back to the bed, collapsing next to her.
—
We lay there, quiet for a while, our breathing even.
Allie was nestled in the crook of my arm. “I could tell you were thinking about her.”
She didn’t sound offended, at least. I was glad I had been honest with her.
I just nodded, glumly.
“I wonder if the way you are with Summer is what it’s like for guys after they’re with me.” She sat up, and was silent for a moment.
Then: “Do you think you’ll text her?”
I sat up too, hesitating on the answer. Early today, I hadn’t been sure. But now…
Reluctantly, I nodded. “I…guess maybe I need closure. Or a chance to yell at her. Or to fuck her again. Or…I don’t know, something.”
Allie didn’t say anything, just gave me a sympathetic smile as she started pulling her clothes back on.
“I’m…sorry, Allie. And I’m sorry you didn’t get to, y’know…”
She shrugged. “I knew what this was. And I had fun, a lot more fun than I usually have.”
I sighed. “Well, I’m sorry I didn’t live up to the hype. I can confirm, though, you are better than other girls at…” I trailed off, helplessly.
Her smile turned sly. “Yeah? Better than Summer?”
I didn’t answer. I don’t know what expression I had on my face, but her smile faded.
“Sorry. You’re a good guy, Jason. I’d do it again, sometime.”
I didn’t feel like a good guy. I pulled my clothes on.
“You know,” I said, hesitantly. “I don’t think playing the field has helped me at all. It doesn’t sound like it’s helped you, either. Maybe you should just find one guy you like and, y’know…work on him lasting longer.”
She looked thoughtful. “I’ll consider that.” The thoughtful look twisted back into her sly smile. ”Are you offering?”
I could tell she was making a joke, but I shook my head sadly anyway. She just laughed, a little sadly.
“Thanks again, Allie. I…” I hesitated. “...just thanks.”
I headed for her door. She followed me down the stairs, watching me leave. I looked back at her in the doorway.
She gave me that sympathetic smile again. “Well, if you ever figure out whatever’s going on in your head, give me a call. After all, you owe me one, now.”
The hairs on the back of my neck stood up at those words as I pulled the door closed behind me.
I was already getting out my phone to reply to Summer as I walked back to my car.
Comments
Bob
I've thought about this for an upcoming story or two; I agree that it's a hot idea.
SunnyCelibacy
I think it would have been very hot if both of them lost control. Be premature for each other.
Benjamin J. Dover
Can't wait for more stories with Summer!
