Riley

I was doing nothing – watching TV – in my dorm room. It had been a long day at the end of a longer week, so I was happy just to have some quiet time, free of demands. I was just starting to really zone out when I heard knocking on my door. Great, someone wanting something from me.

“What is it?” I yelled, not bothering to get up.

“It’s Tressa. Open the door.” Tressa?

Tressa and me, we weren’t friends really. She was best friends with my ex, Caitlynn. Things with the ex (and by extension, her friends) weren’t hostile. This was good, since this is a small school and there’s no avoiding an entire circle of friends, and neither of us wanted any drama.

But why would Tressa be coming by? Things may not have been hostile, but they weren’t super warm either. Plus, I didn’t want visitors right then anyway.

However, let’s not forget that Tressa was cute. And even if it shouldn’t, that still counts for something, so I got up to open the door.

Tressa was standing in the hall with another girl, some mousy first-year who I only half recognized. “This is Riley,” Tressa said, “You know, from that English Writing class we’re in?”

“Oh, yeah,” I said, pretending to remember her, “Hey, Riley.”

“Hi,” she mumbled back, still studying the floor.

“Well,” Tressa continued, “She asked for me help with the paper due next week. She was over and we were talking about a problem she has and thought you might be able to help.” Tressa had a smirk behind every word, something that was always a half-beat away from an actual smile. She was up to something, who knows what, but her smirk was cute, gave her dimples.

Riley, on the other hand, looked more embarrassed than anything. Her gaze was fixed on the ground, and she was wearing some ridiculous frumpy overcoat three sizes too big. I didn’t know what to make of any of this, but two girls at my door? I’d have to be a real jerk not to invite them in, right?

“Welcome y’all, come on in,” I said, making some over-dramatic sweeping gesture.

My dorm room wasn’t much, but what dorm room was? I just had a bed, a round high-top table crammed against the wall, and a desk covered in papers and books and topped with my laptop, screen still glowing with my paused show.

Tressa led the way in, dragging Riley by her sleeve. As Tressa walked past me, I let my eyes drag over her long, bright red hair, the choker around her neck, and her simple gray dress. I’m a guy, and the dress was tight, so I noticed her lack of bra, nipples poking through the dress’s fabric, perky breasts well-supported by an athletic frame.

Tressa sat Riley down on one of the stools surrounding the tiny dining table, then took another for herself. “You going to join us?” Tressa was looking at me, amused, smiling. She’d noticed I was checking her out.

“Uh, yeah, I’m just going to sit down in this chair,” I rambled.

“Yeah, that’s what they’re for.” Tressa didn’t seem mad, and Riley still hadn’t broken eye contact with the floor, so I took the last stool and sat across from Tressa, Riley between us.

“So like I was saying,” Tressa said, “Riley asked me to read her paper, and her writing was… well, ok, but it was really… I just didn’t think her topic was strong enough. It was some childhood pet–”

“Fluffenstuff, my bunny,” Riley cut in, half under her breath.

“—and I thought there’s got to be something more interesting in her life than that,” Tressa continued, “So I asked about boyfriends. And you know what she told me? She told me she’s only ever had one boyfriend, and he sucked, not in the good way.”

We both looked over at Riley. She was still staring at the floor, but her cheeks were flush now with embarrassment. The embarrassment didn’t slow down Tressa any, “She told me there was a lot of things he didn’t do, never did, never bought her gifts, never took her on dates, never said he loved her,” Tressa drew this last one out, then dramatically lowered her voice for the final item, “He never even gave her an orgasm!”

Riley was fully flush with embarrassment now.

“Err, not even once?” I said, lamely. I was caught off guard. Tressa’s story suddenly got much more interesting. And it wakened some instinct deep in my animal brain, but I told my animal brain to shut up.

“No, he just would just, you know, like, cum and be done with me,” Riley said, in a very small voice, so quiet I could barely hear.

“You see? Terrible, won’t even get his girl off,” Tressa said, giving me some expression I didn’t dare guess the meaning of. “That’s why she’s going to dump him the next time they talk.”

“What? You’re still with the guy?” I asked.

“It’s, like, long distance or whatever now,” Riley said, “But he’s supposed to come visit next weekend. Tressa said I should, like, break things off before then, but I haven’t done it yet. I guess… that means we’re still together…”

Tressa put her hands down onto the table dramatically. “I haven’t even told you the worst part!”

I raised my hands expectantly.

“Riley has never had an orgasm in her entire life!” Tressa said this like she’s just announced a major accomplishment.

Now it was my turn to feel embarrassed. I was some guy Riley had just met and here her deepest darkest secrets were being laid bare before me. I felt my own cheeks flush on her behalf. To work through it, I tried to be mature, to keep the conversation going. “Uh, you’ve never, you know, uh, gotten yourself?” I asked.

Riley’s gaze still hadn’t left the floor, but she answered me. “No. I mean, I’ve tried I guess, it’s just never… worked, never felt right, never felt like I thought it should.” She paused, looked up, at the wall instead of either of us, but hey at least she looking up. “I never felt like it was something I should do, like it was, like, dirty or something.”

Tressa said, “Well I’ve certainly never felt that way. I’ve been jilling myself off twice a day since I was 14. I like to think I’m something of an expert in making myself cum.”

My mouth dropped open in shock. Tressa, little as I knew her, girlfriend’s friend, never said things like that to me before. It was a weirdly sexy surprise. I felt my dick twitch in my pants, the state of which I was suddenly very aware of, while my animal brain popped up again to record this moment in the ole spank bank.

Tressa continued, “Don’t look at me like that. You’re a guy, and you guys are always getting yourselves off every chance you get. Why should girls not get in on the fun? In fact, you were alone here in your dorm room at night when I knocked, you were probably about to start masturbating if we hadn’t stopped by, you were probably already doing it!”

“I… I wasn’t,” was the best I could manage. Fact was, I was planning on watching some porn after I finished with my show. I glanced nervously over at my laptop, the screen had gone dark, but Tressa saw my glance.

“You totally were! Your cheeks are red, you’re just as embarrassed as Riley, you can’t even admit it,” Tressa said, smiling widely, enjoying her victory.

I glanced over at Riley, she was looking at me now, studying my expression, my discomfort. I stammered, “I… I…” Getting my first good look at Riley, she wasn’t as frumpy mousy looking as my first take. Yeah, the oversize coat wasn’t doing her any favors, and her face was hidden behind big glasses and low-cut bangs, but she was cute in her own way.

“Anyway,” Tressa cut in, pulling our attention back to her, “When Riley told me of her ‘situation,’” Tressa emphasized the euphemism, “I empathized and knew I had to help her. And I was trying, but girls aren’t really my specialty.”

Did I understand that right? “You were… trying?”

Tressa made a show of being unfazed. “Yes, I was fingering her, or whatever you want to call it. But if you’re not going to do something well, I always say it isn’t worth doing at all, so I stopped.” Riley shifted on her chair, not saying anything. A mental picture of Riley with Tressa’s hand down her pants flashed into my mind. It was awkward. Tressa continued, “And that’s when I remembered you.”

“What? Me?”

“Caitlynn told me when you two broke up, that the thing she would miss the most was the sex. She was pretty drunk at the time, but she said you always got her off, and that she’s never had as many orgasms as her time with you.” Tressa winked at me. “It was enough to make a girl jealous.”

Again I felt my dick twitch, my animal brain was awake and paying attention now. I was having difficulty finding what to say, this wasn’t a compliment I’d had much experience accepting. “You want me to…”

“Yes you dum-dum, I want you get Riley off. I want you to give her the best orgasm – the only orgasm – she’s ever had. She’s nineteen –”

“Eighteen,” Riley interjected.

“Eighteen and she’s never cum, and you’re going to fix that.” Tressa turned to Riley. “Stand up. Take off that stupid jacket. This is too much talking, not enough orgasming.”

Was I really understanding this right? I didn’t think I was bad in bed – who does? – but no girl – not that there had been many – had ever before told me I was good in bed, certainly not Caitlynn. And Tressa thought I was just going to get intimate on command, with some freshman girl I just met? But my objection died as I watched Riley stand up and undress.

Riley opened the coat and underneath she was wearing nothing but a bra and matching panties, both sheer white and made from very thin material. And her tits were huge, squeezed together in the bra, with pink nipples clearly showing through the fabric. Looking down at her crotch, her pussy lips were on prominent display, glistening wet, her panties clinging to them. My first impression was way wrong, the fault of the ill-fitting and unflattering jacket. She turned to toss the jacket on my desk, and I stared, mesmerized by her tits pushing against against her bra, and her thin waist twisted to show off her supple butt. At this sight, I felt my body react, my dick swelling inside my boxers.

Tressa stood up and walked up behind Riley, draping herself over the younger girl, one hand sliding down Riley’s shoulders to slip under her bra to tease and flick her nipple, the other down Riley’s belly and into her panties, stopping at the top of her pussy to rub just above her clit. Riley’s lips parted slightly, and she let out a low moan. It was a lot less awkward than I’d been picturing a moment ago.

Tressa looked pleased with herself, and, looking at the bulge growing in the crotch of my pants, asked, “Do you think you’re up for the challenge?”

I was still at a loss for words, but this time I at least knew what to do. I stood up, and quickly stripped naked, the girls watching, their gazes both lingering on my half-chub cock. Riley watched my dick like she was studying some new just-discovered species, but Tressa had a devilish expression.

“Why don’t you see what we’re working with?” she said to Riley, removing her hands from inside Riley’s clothes and pushing her towards me.

Closing in, Riley stared into my eyes, her face all innocence, her lips moving towards mine, arm reaching around me to bring me in for a kiss. All that build-up for a kiss? It wasn’t what I was expecting, but almost immediately she slid her tongue into my mouth, and she pressed her chest against mine and simultaneously grabbed my cock, sliding her hand down until she was cupping my balls. I gasped into her mouth, pulled her into me, and with my other hand reached down to grab her ass. I pushed my leg up between hers, and I could feel the wet heat of her pussy on my thigh.

She was rubbing and teasing my balls, then gave them a slight squeeze. I broke the kiss and muttered, “Oh, fuck.”

She gave me a doe-eyed look. “Is everything all right mister?”

I heard Tressa giggle, and watched as Riley dropped down onto her knees, pausing only when my rock hard cock was just in front of her mouth. “I’ll kiss it and make it better,” she purred, a bead of pre-cum building at the tip of my dick. Any trace of mousiness in Riley was long gone, I never would have expected this out of the girl who was dragged to my room a few minutes before.

Her hand slipped from my balls back to the base of my cock, and she started pushing it around, swinging it onto her tits and bouncing it side to side. I thought I was fully erect before, but I watched as my cock got even harder. With it so stiff, Riley was having to push harder and harder on the base to make it move, and all this pushing on my prick was making me pant and gasp.

With one last, big yank, Riley made my dick swing down, then it promptly bounced back to straight ahead, but this time Riley’s mouth was there to catch it. She open-mouth kissed the tip, licked the pre-cum off, then slowly slid her lips down my shaft, staring me in the eye the whole while. I felt my dick hit the back of her throat, and she used her hand to jack off the base.

Some time of this – I have no idea how long, really, I was totally in the moment – and Tressa cut in, “Looks like the wrong one of you is about to cum. Riley, we’ll get back to that, but for now get up.”

Riley complied, pulling herself off my dick, and I looked up to see Tressa leaning back, dress hiked up to her waist, legs parted, hand down her panties, thumb on her clit, fingers sliding in and out of her pussy. Oh fuck yes. Not stopping or even slowing, we made eye contact, both seeing the warm flush of sex in each other’s expression. “Eat her out,” she instructed me, between breaths, “Show me what you’re good for.”

I needed no more encouragement than that, I love eating pussy, making girls cum. Of that Tressa was right, and as I guided Riley over to my bed, I used my other hand to run my fingers up Tressa’s thigh, from knee to crotch and then back down to her other knee. She responded by thrusting her crotch forward, digging her hand deeper into her own pussy, and letting out a long, low, moan.

I felt tugging on my dick, and looked over to see Riley pulling me towards the bed, not wanting to lose my attention. “Take your panties off and sit down,” I told her. She did as instructed, turning around and bending over at the waist, hips high, to push her panties all the way down, giving me a view of her ass. I grabbed it with both hands, squeezing and kneading, but pushed her down and sitting onto my bed, draping her legs over the side towards me. I knelt down in front of her, running my hands from her belly to her knees, then pushed her legs apart, wide, spreading her pussy in front of me.

Tressa joined us, caressing Riley’s inner thigh, while still working away in her own panties. Riley’s clit was full and pink, her pussy lips soft and glistening, her whole crotch was soaked wet. I pursed my lips and blew on her clit, watched as it twitched in anticipation, before backing off to tease her more, licking lines down her inner thighs in towards her pussy, making sure my tongue ran over Tressa’s caressing fingers. As I drew my tongue towards Riley’s pussy, I brushed it lightly across her lips the first time, then slightly harder the second time, and again, and again, each time pushing my tongue deeper into her pussy, each time Riley shuddering more and more.

A bit of this, and finally I wasn’t teasing anymore, now just licking up and down her pussy lips. On one lick, I reached my hand up, slipping my middle finger into her. She rolled her head back and gasped as I pulled it back out, then pushed in both my middle and index fingers, eliciting an even bigger gasp. Then my ring finger joined, and soon I was slowly, rhythmically sliding them in and out of her pussy. I moved my tongue up to her clit, gave it a quick lick and saw Riley have a body-wracking shudder for my efforts, before my tongue landed on the ridge just above her clit.

I glanced up, saw her chest heaving in and out, and was transfixed by her tits. They heaved underneath the fabric of her bra. Her expression was one of total ecstasy, lips parted as she breathed heavily, eyes half open with an unfocused gaze. I glanced over at Tressa, she was watching Riley’s excitement build up, and didn’t look far behind, fingers still going furiously in her own panties.

“Riley, how are you doing?” Tressa said between gasps.

“Keep… fucking… going!” Riley managed, pushing my face back down into her crotch. I was loving this, and eagerly resumed.

I pushed my tongue back onto her crotch, right onto her clit, licking building in intensity, timed with my fingers pushing their way into her. I could feel her heat building, feel my tongue sliding across her sex, giving it friction in just the right way.

“Oh god, oh god, oh god, right there, right there, right there,” Riley was moaning. I could feel her nearly there, her whole body shaking as she entered orgasm for the first time in her life. She pushed down on the back of my head, shoving me deeper into her crotch, and squeezed my head between her thighs to hold it there. But I knew better than to change anything, and kept doing exactly what I was doing to bring on this response. I felt her pussy start to spasm around my fingers as her juices flowed, dripping down my wrist and arm.

Wave after wave I felt pass through her, my fingers and tongue never slowing, as she released years of pent-up sexual frustration onto my face.

Finally calming, Riley’s hands relaxed from my head and her thighs stopped squeezing my head quite so hard, and I glanced up. Tressa was pinching and teasing Riley’s nipples, which all three of us seemed to enjoy, the ecstasy still plain on Riley’s face.

So I kept going. I don’t stop eating after just one orgasm, even an orgasm as intense as the one Riley just had. I kept my fingers fucking Riley’s pussy, kept my tongue caressing her clit, and sure enough, after a few moments could feel her building up again. Her body tensed as another wave of orgasm passed through it, her pussy again spasming around my fingers, again her moaning with each breath, “Oh fuck, oh fuck, oh fuck, oh fuck.”

Almost under her breath, Tressa said, “Lucky girl, damn.”

And again I kept at it, I wasn’t going to stop until I knew she was fulfilled, and the way Riley was pushing her crotch onto my face, I knew we weren’t there yet. Happy to oblige, my ministrations soon brought her to a third orgasm, this one culminating in a long wordless groan.

After, as her body finally relaxed, she collapsed down into the bedding. Still I kept licking, but slower now, and I stopped my fingers too, leaving them inside, enjoying the feeling of Riley’s pussy and wetness on my hand. My licking was still eliciting gasps, but each was smaller, and I could feel her heat lose its swell.

I pulled my fingers out of her, gave her pussy one final lick from top to bottom, and rolled back onto my heels, giving Riley a good look. She lay back, slack on my bed, head against the wall. I was distracted by her huge tits, pulling the fabric of her bra in opposite directions, pert nipples denting the material. Her expression was one of total contentment.

I looked over at Tressa, and for a moment we held eye contact. The hand I had used to finger Riley was still soaked in her juices, so I pulled it to my mouth and licked my fingers clean. Tressa had at some point stopped fingering herself, so when I was done with my hand I reached for hers and started licking her fingers clean, too. Tressa’s pussy juice tasted different than Riley’s, sweeter, softer. We were still gazing into each other’s eyes. She had an expectant expression, one I understood perfectly.

“Take off your dress and panties,” I told her. Wordlessly, she slipped her (nearly entirely soaked) panties down her leg, and then began peeling her tight dress up and over her belly and chest. When her perky tits sprung free from the cloth, Tressa’s arms were over her head, showing off the taut athleticism of her body, but the dress momentarily blocked her view. I reached up to her breasts, rang my fingers in circles around her nipples. She paused and drew in a sharp breath. I was careful just to tease her nipples, until I sprang, and suddenly pinched both of them at the same time, playful at first, then just a touch harder, making her cry out, half yelp, half gasp.

She freed her head from the dress, and gave me a surprised look, she wasn’t expecting something like that from me. But here I had my ex’s cute friend naked on my bed, I wasn’t going to let her forget it. I dropped my head level to her crotch, grabbed each of her legs behind the knees and pushed them up to her chest, presenting myself with the second tight, young pussy for the day. Not bad, I thought, and dived in.

Tressa had a piercing on her clit – a ring – and she’d been flicking it for a while now, so when I saw her whole pussy still wet and swollen, I skipped the preamble and started tonguing her clit directly. Tressa immediately gasped, so I figured I made the right decision, and started licking it more forcefully, earning deeper gasps.

Then I sucked her entire clit, hood, and ridge into my mouth, pulling the skin in and letting it slowly slide back out between my tongue and teeth.

“Oh my … fuck … do that again,” Tressa said, so I did, and felt her body start to tense with orgasm. Her legs kicked, but I held them tight flat against her chest as I kept licking her pussy.

“Hold your legs here,” I instructed, and as she complied, I dropped my hands down to her crotch. I petted her pussy, teasing her opening. I dropped lower, my thumb sliding to rest on her asshole, teasing her other opening. I felt Tressa lose control, the orgasm washing over her, her body becoming mine to control. My tongue and fingers brought her to the peak of ecstasy. Her pussy and ass spasmed around my thumbs over and over again, before finally, for the second time tonight, I felt a girl go completely limp underneath me.

“This is the best idea I’ve had in months…” Tressa said.

I stood up, cock swollen and hard, its head deep purple and ready to burst. I started climbing onto Tressa, fully intending to fuck her face.

“No, I have a better idea,” Tressa said.

I was disappointed, I was really looking forward to cumming. “This idea better involve my dick,” I said.

“Don’t worry,” Tressa said, and ran one finger down the bottom the length of my cock. I nearly almost came right then, I was so ready to go. “Riley, get up.” Then Tressa said to me, “Lie down on your bed.” I did. “Now, Riley, get on top, 69 him.” We both perked up at this suggestion, and Riley moved to sit down on my face, I watched as she rested her pussy lips once again on my tongue, and as her plump, gorgeous ass settled right in my face. I felt her lean down, mouth approaching my long-neglected cock, and I dug my tongue into her pussy lips in anticipation.

Finally, I felt Riley’s lips return to my dick, slide down the shaft. But I also felt something else, a warmth on balls. Someone was sucking on my balls! Tressa, I realized, this is a better idea. I spread my legs wider to give her easier access, and was rewarded with my balls being fully sucked into Tressa’s mouth, her tongue running up and down each side as her lips tugged on them gently.

Meanwhile on my cock, Riley was making effort to take it in deeper, pushing it down her throat to make it fit. Now was my turn for total ecstasy, and I knew I’d not be able to last much longer. I reached up, grabbing, squeezing, caressing Riley’s ass one more time. I slipped one hand down, pushing my thumb into her ass, hearing a muffled squeal escape her mouth, and then I came.

I felt my cock tense up even firmer, and Tressa responded by tugging even firmer on my balls, as I loosed spurt after spurt of cum down Riley’s throat. The waves of orgasm kept coming, I felt my balls tense over and over, and the girls kept sucking. Only after some time did my cock relax, and I felt the girls lift themselves off. Riley stood up off me, and I looked over to see a huge load of cum dripping from her chin.

As she grabbed some napkins to clean herself up, Tressa sat down between my legs on the bed, grabbing the base of my cock again between in her hand, swinging it back and forth like Riley had done earlier. My dick, spent as it was, was again at half-chub, although I wasn’t sure if this was just a leftover from before.

“I bet you’ve never cum like that before,” Tressa said to me. “Riley just had her first orgasms, but there’s lots of other firsts happening here tonight.” And as Tressa swung my cock down towards her pussy, I noticed it definitely was getting harder.

“Oh oh oh, what’s this?” Tressa said. Riley come back over to watch. “I think he’s ready for some more. This night isn’t over yet!” She pushed my cock up against my belly, her other hand massaging my balls. Riley’s hand had found its way down to her own crotch, and she was starting to stroke her pussy in time to Tressa’s hands on me.

My cock was now fully hard again, I couldn’t believe it, I had never recovered this quick before.

Tressa’s hands felt great, but I was transfixed by Riley’s actions on her own pussy, so I said, “Riley, why don’t you take a seat on my lap.”

She was happy enough to oblige, and I watched as she straddled my cock, Tressa’s hands guiding it into Riley’s eager pussy. Riley slid herself all the way down to my hilt, and we gasped in unison, before she started pumping herself up and down on my dick, pleasuring herself on my erection.

Tressa got up from the bed and shuffled through her bag, pulling out a phone. Before I had time to really consider what she was doing, she said, “Riley, I think this is a good time for you to break up with your boyfriend.”

Riley froze. “What what?” But I kept thrusting into her, not letting our rhythm break.

Tressa continued, unabated, “Now you know what you’re missing, what he doesn’t give you, there’s no point in keeping him around. Here, it’s connecting now.” Tressa handed the phone to Riley, and I grinned, getting more enthusiastic in my thrusts.

Riley looked mortified as we heard a guy’s voice come on the line. Right as she started to talk, I gave her a extra deep thrust. “Ahhh uh, hi Richard. You’re … uh … still coming this, err, weekend?” The guy, Richard I guess, must have been saying something, but Riley started making a long moan, “ohhhhhhhhh.” I looked down, Tressa had her face up Riley’s ass, she must have been rimming her. Holy fuck, so hot.

“Oh, uh… that was just… my roommate… she’s sick, I guess…” Riley was managing to stammer, although she was breathing pretty heavily again, and had mindlessly started meeting my thrusts again with her own. “Listen… maybe… you shouldn’t come this weekend…”

We heard angry yelling from the phone, and Tressa pulled back to say, “Tell him,” then dived right back into Riley’s ass. I reached up to pinch Riley’s nipples.

“You shouldn’t come this weekend… ohhhhhhhhhhh… or ever… again… just… uhhhhhhhh … we’re done… ohhhh,” Riley managed. We heard lots of yelling from the phone now, but she just hung up and tossed the phone to the floor.

“Doesn’t that feel freeing?” Tressa asked.

But Riley ignored the question, instead instructing Tressa, “Get your tongue back up on my ass.” She resumed fucking with enthusiasm, pumping her pussy onto my cock. I felt Tressa’s tongue sometimes slip down and tease my shaft as Riley’s pumping got more and more wild. Soon, Riley was cumming, and as the orgasm washed through her she went limp on top of me.

I hadn’t myself cum yet, so I pushed her off me and onto her hands and knees, pulling myself up behind her.

“Wait,” Tressa said, and she crawled down beneath us, head right under our crotches. “Fuck her ass,” Tressa commanded me, before shooting her tongue up into Riley’s pussy.

So again I grabbed Riley’s ass, spreading her cheeks with my hands, resting the tip of my cock right at her asshole. I started by just pushing the tip of my cock into Riley’s ass. She was very tight, very tense. But I eased her into it, pushing only slightly farther in with each thrust, and I felt Riley relax. Soon I was sliding my cock all the way in, tip to base, my hands on Riley’s hips, pushing her beautiful ass onto my hips.

I was already losing myself in this, feeling myself come close to orgasm, when again Tressa took my balls into her mouth. Feeling her again sucking on my sac, licking up and down, this time while fucking Riley’s ass, I just completely lost any resistance, cumming hard, pumping my load into Riley’s asshole.

I dismounted and leaned back against the wall, totally spent, cock lying limp between my legs, semen dribbling out. I watched as the girls rearranged themselves into a proper 69 on my bed next to me, and kept eating each other out.

After a few minutes of licking and moaning and panting, Tressa suddenly popped her head up. “Oh, fuck, I gotta go.”

“What? Where?” I asked.

“I’ve got a date,” she said.

“You’re fucking kidding me.”

“I totally am not.” Tressa pulled herself off Riley, giving her a sad look. Riley and I watched as she started pulling her dress back on. “I told this guy I was going to meet him. He wants to take me to a club, I think he wants to get into my panties.” Tressa winked at us.

Riley crawled over to me, nestled up against me, going doe-eyed and asking “Can I stay? I’ll do … anything.”

Spent as I was, the idea of yet more sex lodged itself into my brain, and I wrapped my arm around Riley, pulling her nearly naked body against mine.

Tressa had slid back into her tight dress, tits once again poking through the fabric. She turned to us and pulled up the front of the dress, showing us her still-wet pussy, naked. “Little does he know I won’t be wearing any,” and she giggled.

Seeing Riley and me cuddled up, she said, “Aww, look at you two. You make a sweet couple.” Tressa fished through her bag, set a pile of clothes on the table. “Riley, here’s your things, I’ll catch up with you later.” Then she tossed something on the bed in front of us. “And here’s my favorite lube, just in case.” Tressa winked again, and with that left my dorm room, closing the door behind her.

“Fuck, she’s sexy,” Riley said. “I never thought I could be into girls, but Tressa really turns me on.” Riley looked up at me. “Don’t be jealous though, I’m still into boys, too.” With that, she rested her hand on my knee, fingertips ever so slightly starting to make their way up my thigh.

At the same time, she casually reached her toe over to my laptop, hitting the space bar to wake and unpause the show I’d had on before the girls came over. “What were you watching anyway?”

The tv show began to play, but I could only half pay attention. Riley’s hand now on my inner thigh kept distracting me, and I was very aware of my arm wrapped around her, how my bicep was brushing against her tits, my hand gently petting her belly. When had I started doing that? I glanced down at the lube Tressa had left us, and, incredibly, felt my dick twitch. Would I really be able to go again?

Riley apparently noticed the swelling starting again in my cock, and gave me her most innocent, sexiest smile yet. “I didn’t finish draining your balls last time?” She moved her hand from my thigh to my balls, and started teasing them with the tips of her fingers and thumb. Caressing my balls from their base to just below my cock, and back, my dick started swelling again, lifting itself up from its spent, limp state.

All on its own, my hand had slipped up under Riley’s thin bra and was squeezing and kneading her tits, I hadn’t even noticed.

Riley said, “When Tressa decided we were coming over to see you, she made me put on this lingerie. I think it was hers, that’s why this top is so tight. But it looks better on a girl like me, don’t you think?”

I turned my full attention towards her tits, seeing the way they pushed against the tight fabric. And as my hand squeezed and groped one tit, I watched the other tit’s hard nipple tent the bra, pink skin visible through the sheer material. I could worship tits like that.

Riley lifted her hand from my balls, gave my cock a gentle slap. It had swollen up stiff as a board, I was somehow fully erect again. “You naughty boy, you get hard so easily!” Riley slapped my dick again, watched it quickly spring back up. She said, “I just can’t get rid of this thing, it keeps following me around!” all the while batting at my dick, pre-cum dribbling down from the tip. “That just won’t do,” she said, and with her other hand reached for the lube.

She pulled my hand out of her bra and squeezed out some lube into my palm, then guided my hand down to her crotch. My hand knew what to do, rubbed the lube into her pussy, and I started running my fingers up and down her pussy lips and flicking her clit. I heard Riley sharply take in a breath, but she didn’t stop what she was doing, and putting some lube on her own palm, began to rub it into my dick in long, slow strokes.

We sat there, pressed up against each other, masturbating each other. The tv show still playing, now long forgotten, drowned out by the sounds of our gasps an moans. I don’t know how long we sat there jerking each other off. Riley was changing her tactic back and forth between vigorously whole-fist pumping my cock, and two finger teasing the underside, edging me along, reapplying lube every few minutes, a steady stream of pre-cum mixed in. My fingers were doing the same to her, alternately teasing and fucking her pussy.

We writhed and moaned together in mutual bliss for some time before I told her, “I’m can’t hold back any more… I’m gonna cum.” Riley was an angel, and changed her grip to the sensitive forward tip of my cock, firmly stroking me with eagerness, and leaned forward, putting her face over my crotch.

I could only take a few seconds of that before my dick sprayed out a load, shooting cum on Riley’s face, coating her glasses. She pumped again, and a third time, and another load shot out. Riley’s face was dripping with my semen. She kept on pumping, and the cum dribbling out, running down her hand. She looked up at me, semen dripping from her hair, her glasses, her nose, running down her cheek, sliding into her mouth and down her chin. “How do you have so much cum?” How do you even answer that? But her hand was still pumping my cock, so I didn’t say anything, just relaxed and let her keep draining my balls.

Riley sat back down next to me, making sure my hand returned to her pussy. “It just keeps coming!” she said, and I looked down. Sure enough my cock was somehow still semi-hard and managing to issue semen with each stroke of her hand. We both watched, amazed, as the cum didn’t stop, and it flowed down her hand and onto my chest and balls.

“Holy fuck, hoooo…” Riley groaned, the sight of my cumming cock sending her over the edge into yet another orgasm. My fingers knew the drill, and lubed up as they were, were able to apply more pressure without rubbing her raw. She convulsed against me, eyes rolling back into her head. Finally she relaxed, pulling her hand from my limp cock, curling up, nuzzling her head against my chest.

I draped my arm instead down her side and onto her hip. I stroked her head, enjoying the post-coital affection.

By some mutual, unspoken agreement were were both well and truly spent, so I grabbed some spare towels to clean up best as we could. While doing that, though, I kept stealing glances at her, I mean, I still had a hot naked girl in my dorm room.

She looked strangely nervous, though. It took me a bit to figure it out, but when I did, I told her, “You can spend the night, if you want.” Maybe I had just met her, and maybe it was the afterglow speaking, but the way she felt cuddled against me, it felt right. And who knows, maybe morning sex tomorrow!

Riley at least looked visibly relieved. “I, uh, I’ve never done this before, I don’t know what I’m supposed to after the sex. It’s really ok if I stay?”

“Look, I’m not… I don’t… that was fucking incredible,” I said, “There’s nothing we’re supposed to do now that we don’t want to do. And even if I was jerk enough to kick a girl out after sex, you’re just too cute for that.” And would you believe it, she blushed.

I guess I’m just a big softee.

4 thoughts on “Riley

  1. Hopefully I have found your first story. You certainly have developed your skills but you sure started from a very gifted base. Thank you 💋

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    1. This was the first I posted online, yep. I’d stumbled through writing a smattering of un-posted things before this over the years but never “finished” them or shared them out before this. And at the time I wrote this, I had no idea I would writing more and more stories like it.

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      1. I have always been interested in sexuality. 10 years ago I was doing my MA on sexuality Australian Aboriginal s. One thing this did for me it lifted my understanding and appreciation of good writing. I did my Honours on Nabokov “writer of Lollita”. I am dyslexic so your writing is amazing and completely unattainable to me. Please continue your writing it is so beautiful to read.

        John

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