The Challenge [MFF] [oral] [long]

I was doing nothing – watching TV – in my dorm room. It was after a long day and a long week so I was happy just to have some quiet time, but someone was knocking on my door.

“Who is it?” I yelled without getting up.

“Tressa! Open the door.” Tressa and I had an English Writing class together and we weren’t friends really, she was best friends with my ex, Caitlynn, but things with the ex were amicable and so Tressa and I got along ok in class. But I had no idea why she would come to my dorm room. Despite not wanting visitors right then, 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 from our class, some mousy first-year who I only half recognized. “This is Riley,” Tressa said, “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 growing that wasn’t quite making it into a smile. She was up to something, was she flirting? But I didn’t know her well enough to want to guess, just to be disappointed later.

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, why would I turn that away?

“Hi Riley”, I said.

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

Unimpressed, I tried again. “Welcome, come on in,” I said, making some over-dramatic sweeping gesture. The dorm room wasn’t much, but what dorm room was? I just had a bed, a small, round dining 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, setting her bag down and sitting them down on the stools surrounding the tiny dining table. Tressa closed the door behind her, and as she walked past me, I took the opportunity to check her out. Like I said, I always thought she was cute, and a good part of that was her style, long, bright red hair, and fashionable outfits. Tonight, besides her standard choker around her neck, she was wearing a simple gray dress, and I’m a guy, and the dress was tight, so I couldn’t help but notice she didn’t seem to be wearing a bra. Two perky nipples were poking through the dress’s fabric, and my brain automatically assessed her tits: smaller, but well shaped, well-supported by an athletic frame.

“You going to join us?” Tressa was looking at me, amused, smirk now full, she’d noticed I was checking her out. *Oh shit, play it cool.* ”Uh, yeah, I’m just going to sit down in this chair.” *What the fuck am I saying?*

“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 joined them at the table, Tressa across from me and Riley between us.

“So like I said, Riley asked me to read her paper,” Tressa said, “and her writing was ok, but 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 to talk about,” Tressa said, “so I asked about boyfriends, and she told me she’s only ever had one boyfriend, and it wasn’t a very good relationship.” 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 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. This sexual turn in the conversation wakened some instinct deep in my animal brain, but I didn’t know where Tressa was going with this, so I told my animal brain to shut up.

“No, he just would 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 long distance now,” Riley said, “but he’s supposed to come visit next weekend. Tressa said I should 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 returned the dramatic gesture, raising 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 her deepest 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.

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 dirty or something.”

Tressa said, “Well I’ve certainly never felt that way. I’ve been jilling myself off every 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. I didn’t know Tressa all that well, and hearing her talk so frankly about sex was a surprise to me, a weirdly sexy surprise I totally wasn’t expecting. 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, guys are always getting themselves off every chance they get. Why should girls not get in on the fun? 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, if you weren’t already.”

“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.

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 looking as my first impression. 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 that word’s 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. 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 orgasms as good as the ones you gave her.” 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, no girl had ever been so frank about sex like this to me before. “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.”

I couldn’t believe I was hearing this. I didn’t think I was bad in bed – who does? – but no girl – and there haven’t been that 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 as I watched Riley stand up and take off the coat, my animal brain took control, and my objections never made it to my mouth.

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, that Riley was “mousy”, was way off, 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.

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 ending up 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.

Now inches from me, 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 her thighs, and I could feel the wet heat of her pussy on my leg.

She was rubbing and teasing my balls, then gave them a slight squeeze. I broken the kiss to mutter “oh fuck” and she gave me a doe-eyed look. “Is everything all right mister?” I head 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 knocked on my door 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 hard before, but I watched as my cock got even harder than I knew it could. 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 breath harder and harder.

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 rest that didn’t fit in.

A few moments 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, she looked at me, or rather we looked at each other, both seeing the warm flush of sex in each other’s expression. “Eat her out,” she instructed me, between breaths, “show us 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, “ohhhhhh”.

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 I instructed, pushing her panties down, but turned around and bent 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 both my hands from her belly down to each of her knees, then pushed her legs apart, wide, spreading her pussy in front of me.

Tressa came over, sitting down on the bed next to Riley, one hand caressing Riley’s inner thigh, the other still down her own panties, going strong. I leaned forward, in towards Riley’s pussy. Her 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 fucking her with three fingers, slowly 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 undulating underneath the fabric of her bra. Her expression was one of total ecstasy, lips parted as she breathed heavily, eyes half open and 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 clit swelling, 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.

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, cumming so many times.”

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 moan, “hhhhhrrrr…” 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 up to my palm, 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 clit 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 the bed, huge tits pulling the fabric in opposite directions, pert nipples denting the material, expression one of total contentment.

I looked over at Tressa, saw she was looking at me, and for a moment we just sat looking into each other’s eyes. 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 staring 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. One I used to start petting her pussy, teasing her opening. The other 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 as 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.”

“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. My cock eventually relaxed, 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 this, 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.

“Get your tongue back up on my ass,” was all Riley had for a response, as 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. A few minutes later 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 shit, I gotta go.”

“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 pulled herself 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 cognizant 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?”

*What an invitation!* 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 a pair of 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, the 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 only sounds our labored breathing, the squishy noise of fingers sliding through lube, with the tv show still playing, now long forgotten. I don’t know how long we sat there jerking each other off, Riley would change 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. With each additional pump of her hand, another load shot out, and soon Riley’s whole face was dripping with my semen. She kept on pumping, and the cum started to ooze out of my dick rather than spray, getting all over her hand, too. 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 shit, hrrrrrrrrrr…” Riley said, 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, tongue lapping at the cum dripping down her mouth. Finally she relaxed against me, pulling her hand from my cock, which was once again lying limp between my legs. She licked my cum off her hand and curled up, nuzzling her head against my chest.

I pulled my hand back from her pussy, draping my arm instead down her side and onto her hip. With my other hand 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 moment 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, but I did like the way she felt cuddled against me, and it wasn’t like I had anything else going on. Plus, 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 don’t have much experience doing this either. And even if I was jerk enough to kick a girl out after sex, you’re just too cute to do that to,” I said, and would you believe it, she blushed.

Riley did end up spending the night with me in my dorm, our naked bodies pressed against each other on my small dorm bed. We did end up fucking again, too, once in the middle of the night when we both realized we were awake, and then again in the morning. I have no idea how my dick survived that day, it was sore for a while afterwards.

Even though we hadn’t before know each other, Riley and I both enjoyed that night enough to keep meeting up regularly for sex, and I guess I’m a big softee, since it eventually developed into a real relationship. I was graduating that year and wasn’t planning on sticking around town after that, but there’s a lot to be said about a girl who so easily makes your dick so very hard, plus we did work together pretty well, so I rearranged my plans to be able to stay with her.

Tressa did end up coming by maybe a dozen more times that year, but always strictly for sex. Sometimes with Riley there, but usually without, Tressa called me her “good sex charm” and used me as a fuck-buddy, making sure I was there to get her off before she went out on dates, and once or twice just because she was horny and lonely. Riley was ok with it, but only because Tressa had gotten us together. And anyway once Tressa graduated that year, she did leave town, which made things simpler with Riley.

Riley and I are still together all these years later, and our favorite role play is recreating our first night together.

Source: reddit.com/r/sexystories/comments/f97eti/the_challenge_mff_oral_long