As the title implies, this story will eventually
involve cheating. Yes, I’m aware that I’m a bad person. If it makes you feel better you’re welcome to tell me yourself, but trust me, I already know. With that out of the way, this story takes place back when I was around 22 and a senior in college. I had been dating my then girlfriend, Sasha, for about a year, and up until this point had always been faithful to her and my previous exes.
We were pretty serious at the time, but there was an unspoken feeling between us that we weren’t going to immediately base our post-college lives around each other if it didn’t work out. We had also made a pre-graduation bucket list going into our final year together one night after a date, and one of the last items on the list was a threesome. Back when we were writing everything down, I wasn’t sure how serious she was when she added it to the list, both of us laughing when she wrote it down.
We were a pretty kinky couple, me a little more so than her, and while I had obviously always fantasized about a threesome it wasn’t something I felt like I absolutely had to do. We didn’t talk about it for a few weeks after we made the list, but one night at a party her and her roommates were hosting the topic came back up. Throughout the party, Sasha and I kept ending up talking to and playing drinking games with Emma, a classmate of one of her roommates. We had hung out with Emma in passing, but this was really the first time that we had any sort of meaningful conversations with her.
As the night wore on, there was a very flirty and fun vibe between the three of us. I could tell that Sasha and Emma were feeling it too, noticing some lingering touches and frequent compliments passing back and forth between them. I remember one specific moment when they were teamed up in beer pong, and after Emma hit a winning throw the two of them dramatically laughed and hugged, Sasha kissing Emma on the cheek. I was across the room talking to another friend, but I could see Emma's hands were wrapped low around my girlfriend's waist, and before they pulled away Emma playfully reached down and squeezed her firm little butt a few times.
At one point a little later in the night I accompanied Sasha upstairs to one of the bathrooms as she had to pee. As tipsy, horny college kids, we also made a pit stop by her bedroom right next door, frantically making out as soon as the door closed. Sasha was insanely turned on, grinding onto my thigh as we made out and whimpering in between kisses. I had my back pressed against her door and spun her around, pulling her back against my chest, her ass pressing into me. While I kissed her neck I slid my hands down across her breasts, groping them over her top, then further down to quickly undo the button and zipper of her jeans.
Just as I slipped my fingers under her very damp and wet panties, I whispered in her ear, asking her if she liked feeling Emma’s hands grabbing her ass. She giggled a little, responding in a playful tone “I didn’t know if you saw that … did it make you jealous?”.
I started massaging her clit, causing her to buckle into me a little as I said “not at all … I bet she’d love to feel what I’m feeling right now”, my fingers sliding lower and curling up inside of her. I continued to finger Sasha for another minute, and just as I felt her breath start to change and her body start to get flush and warm, I pulled my fingers out of her and quickly zipped up her pants. Just as she started to protest, I slipped my fingers into her mouth as she instinctively sucked on them, shutting her up and cleaning them off for me.
I whispered into her ear “good girl … now lets go back downstairs before anyone comes looking for you”. Her face was flush and the outline of my erection was probably visible through my jeans, but I didn’t have a care in the world at the time. With almost comedic timing, at the bottom of the stairs we turned into the kitchen to grab another drink and almost bumped directly into Emma, having the same idea.
She smiled when she saw us, doing a double take at Sasha’s flushed face and slightly messy hair. With a slight laugh she said “I was wondering where you snuck off too … you guys are quick”. I could tell Sasha was a little embarrassed by the comment, but I just laughed it off and said “no need to be jealous”, stepping past her with a wink to grab us all beer from the fridge.
A little later in the night when there were just 10 or so people left, we naturally ended up playing a drinking version of “never have I ever”. As everyone remaining was pretty tipsy to begin with, we skipped over the timid rounds and jumped straight into the more raucous and sexual themes. One of Sasha’s roommates started with an obviously very targeted statement, looking right at the guy she had recently started dating, saying “never have I ever gone down on a girl”. When he was the only guy at the table who didn’t drink, the girls erupted in a fit of laughs and boos. While all the attention was directed on him, I noticed Emma was the only girl to take a drink, doing so subtly.
A few rounds later it was Emma’s turn, and she went with “never have I ever cheated on someone”. At first no one reached for their drink, everyone pensively looking around the table, until another one of Sasha’s roommates spoke up and said “ugh fine you guys are lame I did once”, reaching for her drink to a chorus of laughter and questions.
Sasha was standing to my right, and when it came round to her turn she looked across at one of her friends and confidently said in a drunken voice “never have I ever had sex in a classroom on campus”. I immediately turned to look at her and started to mumble out an “uhhh are you sure about that?”, recalling a memory from just a few weeks ago when Sasha and I were working late in our school’s 24-hour library. We were downstairs in a private study room and I distinctly remember us having a very hot quickie … Anyways, story for another time.
Before I could even finish my sentence Sasha quickly cut me off, putting a hand on my chest and saying loudly “that technically wasn’t a classroom”, causing everyone at the table to burst out laughing. The friend Sasha obviously targeted the question at took her drink, along with one other couple playing along. After the laughter and chaos died down, Emma spoke up and asked “well where was it if it technically wasn’t a classroom?”. I looked down at Sasha just as she turned to look up at me, and when we both shrugged in unison I responded, saying “library study room”, causing even more laughter amongst the group.
I was up next, and feeling a little bold held eye contact with Emma as I said “never have I ever had a threesome”, a slight grin spreading on her face as I said it. Unfortunately no one reached for their drinks, which per our house rules meant I had to take a shot. Amidst some drunken cheers, I took a shot of the cheapest vodka a college budget can afford, and when it tasted like water I knew I was going to be in for a rough morning.
We went around a few more times until one of Sasha’s roommates eventually lost, but all I can really remember was more and more drinking. Eventually once the game ended everyone was pretty done for, and the remaining few folks at the party called it a night. I was fully ready to head up to Sasha’s room and pass out, but as folks started trickling out and saying goodbyes it came up that Emma lived on the complete opposite side of campus as everyone else, a good 20 or so minute walk away. I would have offered anyway, but Sasha was quick to volunteer me so she wouldn’t have to walk alone.
Emma very softly and politely declined at first, but after reassuring her I wouldn’t mind a walk she happily accepted. I gave Sasha a quick kiss and told her I’d come back, but to not wait up for me, then set off with Emma. The fresh air was a welcome change, sobering both of us up just a little, and as we walked we were bantering back and forth about the party.
At some point she brought up the game we all played, saying how wild it was that Sasha’s roommate called her date out for having not gone down on her, or anyone. We laughed about it again and I brought up how she had taken a drink to that one. She confessed that she had done some “experimenting” throughout college and while she had never truly dated another woman she did enjoy hooking up with them. I remember making some humorous comment about how great minds think alike, and we ended up talking about how much we both enjoy eating a woman out.
It was very obvious how horny we both were, the tipsiness giving both of us the confidence to openly acknowledge it. During the next lull, I told her about my theory that most of the time when someone says something they haven’t done in “never have I ever”, it’s something they’ve secretly thought and fantasized about doing.
Emma feigned offense at this, stopping momentarily to playfully hit my arm and say “what, so you think I secretly fantasize about cheating?”. I backpedaled a little on my statement, reemphasizing the “most of the time” part of my theory, but teased a little, adding “but I wouldn’t necessarily be surprised”.
Thankfully she just laughed, then said “well I mean you obviously fantasize about having a threesome, and apparently Sasha wants to get fucked in a classroom”. I confessed that she caught us red handed, and she quickly asked “So wait, what happened in the study room?”.
I told her in fairly explicit detail how we had been studying late in one of the basement study rooms. We had been playfully teasing each other and joking around, but when the automatic motion lights turned off in the basement we realized that it really was just us down there in the study room. I told her how there was a really hot tension in the air when we both had the same idea, knowing the lights would turn back on if someone came down the stairs, and we both just went for it.
Emma was very quietly walking beside me while I told her all of this, and when I finished my story by telling her how she had dropped to her knees and finished me in her mouth after fucking her on the table, there was a moment of silence where the only sound was our footsteps crunching some fallen leaves. Emma broke the silence first, letting out a small nervous laugh, then saying “fuck that sounds like so much fun”.
After agreeing with her, she then asked “So have you guys talked about it? Is she into it?”. I didn’t understand her question at first, asking her what she meant, and she clarified “like does Sasha also want to have a threesome?”.
The building she lived in was in sight now so I knew our conversation wouldn’t last much longer, but I quickly told her about our “bucket list”, explaining how Sasha had been the one to propose it. I told her I wasn’t really sure how serious she was about it, and contemplated telling her about our brief rendezvous in her bedroom earlier where Sasha had been insanely turned on when I teased her about Emma’s hands on her ass. I decided to hold back that information, instead asking her “I mean doesn’t everyone fantasize about a threesome though? Do you think you’d want to have one?”
All she said in response was “Yeah, I’d love to”, both of us taking a moment to turn and look at each other as we walked up the final path to her building, a very flirty and sensual air between us. We lingered out front of her building for a moment, both of us saying how fun the night was and how tired we were getting.
There was a slight pause, then Emma asked “think Sasha will still be up when you get back?”. I responded saying “with how much of a heavy sleeper she is, she was probably snoring by the time we got to the sidewalk … Why do you ask?”
With a nervous giggle, she said “maybe TMI but all this talk and this whole night has me worked up and I think I have to get off before I can sleep … I was just wondering if she’d be up waiting for you or something”.
In the moment I just assumed she was fantasizing a little about Sasha and I given our extensive sexual conversation on the walk, but with hindsight realized this was probably a very subtle invitation. I just responded by saying something like “I wish, probably in the morning though”, trying to tease a little still. With that, Emma thanked me again for walking her back to her building, then went in for a hug. The hug lasted just a moment too long to be an innocent thank you / goodbye, but at the time, not having the confidence to go further I pulled away first and went on my way.
As predicted, when I got back to Sasha’s about 15 minutes later, the house was dead quiet. I crept silently upstairs to her room, and at first was excited as there was a faint glow from her dim bedside lamp coming from under the door. As I opened it though, I could hear Sasha’s characteristic heavy sleeping breath. I wasn’t too let down though, as Sasha had fallen asleep completely nude on top of the sheets, her small pink vibrator clearly used and laying on the bed next to her.
I got naked and crawled into bed next to her, and when I reached across her to turn her light off she woke slightly, turning to kiss me and mumbling out a half conscious “sorry fell asleep … tried to stay up”. I was crazy horny, but also crazy tired, so after a quick kiss she rolled to her side and I pulled her into me, her warm body pressing against mine as we both instantly fell asleep.
______
I remember it being one of those sleeps that felt instant, as if I had just blinked and suddenly a very soft morning light was starting to fill the room. Sasha and I were still in the same position, her warm body pressed up snug into me. I first noticed how thirsty I was, my mouth painfully dry. As I gently reached across Sasha to grab her water bottle she kept on her nightstand, I next noticed just how hard I was, my morning wood resting perfectly between the backs of her thighs and butt.
I felt her stir ever so slightly as I quenched my thirst, both of us readjusting as I set the bottle down and settled back in behind her. I draped my right arm over top of her, my hand naturally finding the curve of her breast, palming it and squeezing slightly as I pulled her in as close as possible.
She nuzzled back into me and let out a soft sleepy sigh. We were both in that sleepy early morning dreamlike state, unsure if we were truly awake or falling back asleep. I placed a gentle kiss along the back of her exposed neck, her morning hair somewhat messily strewn across the side of her face. She let out another faint sigh, slightly rubbing her hips and butt back into me. I continued to softly kiss the back of her neck, savoring the feeling of her body moving against me. The more I kissed, the more she wiggled her hips, both of us slowly waking up more and more, my erection pressing harder and harder against her.
My hand started to knead her breast, her hardening nipple rolling between my fingers. Each time I flicked across it she pressed harder back into me, her soft moans growing a little louder. I continued kissing her neck, working up to her ears a few times, and massaging her breasts for a few minutes, eventually letting my hand drift up and down her toned stomach.
I started teasing my fingers down lower, tracing the v-line of her soft abdomen, running my finger tips through her trimmed bush, then back up to her breasts. After a few more minutes, all the while Sasha gyrating her hips against my cock, I began pinching her nipples softly, kissing harder and gently biting her neck. Neither of us had spoken yet, our deepening breaths and soft moans saying everything that needed to be said.
I swear I could feel heat radiating from between her thighs, and on the next pass of my hand down her abdomen her thighs parted ever so slightly, giving me enough clearance to slip my fingers between her lips, finding a soaked, warm pussy eagerly awaiting my touch. My fingertips rubbed soft, small circles around her clit, eliciting a slightly louder moan from Sasha. She continued gyrating her hips, grinding into my fingers, and with a slight adjustment from both our hips my erection slipped from pressing against her ass to resting between her thighs. The tip of my cock seemed to naturally find her opening, her warm lips pulling me closer.
We continued grinding against each other, one of my hands pinching and teasing her nipples, the other rubbing her clit, occasionally bumping against the tip of my cock as it slid up and down between her lips. I could feel her wetness coating my shaft, a tingling sensation running up my spine at the sensation as I kissed her neck harder. Once I noticed her breathing get deeper and faster, I slid my hand from her breast up her chest. Tracing my fingers along each side of her neck, I gave it a gentle squeeze to pull her head back, then slipped my pointer and middle finger into her mouth.
Just as she desperately sucked onto my fingers, I adjusted my hips ever so slightly, and on the next rock of her hips back into me my cock effortlessly slipped inside of her. She bit down on my fingers and let out an almost guttural moan as I bottomed out inside of her. I could feel her squeezing around me as my fingers kept a steady pace rubbing circles around her clit. Her right hand gripped against my forearm, her left reaching behind her to grab my hair and pull my head back into her neck.
I sucked hard against her neck, leaving a visible mark, and as I did I felt her body tense and her grip around my forearm tighten. I rocked slightly into her, my cock mostly bottomed out inside of her, sliding in and out maybe an inch. She moaned into my fingers as her tongue swirled around them, her pussy contracting around me as an orgasm washed over her. My fingers slipped out of her mouth as she moaned through it, then the first words of the day were spoken as she let out a low “fuck … fuck me baby please”.
Just as her orgasm subsided I pressed into her shoulder, rolling her facedown on the bed. I slipped out of her briefly, but quickly rolled on top of her, her hips rising slightly to meet my cock as it penetrated her again. I didn’t hold back this time, knowing how much she loved to be roughly fucked laying prone like this. As I began to thrust into her, letting her feel the full length of my cock sliding in and out, my free hand pressed the back of her neck and head into her pillow, stifling her moans.
I’m always horniest in the mornings, and coupled with all of the pent up sexual energy from the previous night, I knew I wasn’t going to last long. As I roughly fucked her, I leaned down and whispered to her, my first words of the day, telling her how good she felt, asking if she liked starting her day getting fucked face down like this.
She wordlessly moaned in response, loud enough that if any of her roommates were up they probably would have heard. I slipped my hand from the back of her neck to her mouth, clamping down around it to quiet her. She bit down on the side of my palm, and feeling her warm and wet mouth on my fingers quickly brought me to the edge of orgasm. I whispered out a soft “fuck baby I’m close”.
As much as she could in her pinned position, Sasha moaned out an “mmhmm” and nodded her head, lifting her hips slightly giving me a better angle to thrust into her. Finally I couldn’t take it any longer, letting my orgasm crash over me, bottoming out inside of her as I filled her with my cum. I could tell that it was quite a large orgasm, my cock spasming for what felt like twenty or thirty seconds.
After my orgasm subsided, I collapsed on top of her, letting my cock soften while kissing her neck and the side of her face, her hair a little sweaty and matted to the side of her head. Once both of our breaths returned to normal, she stirred a little and I rolled off of her. I reached to her bedside table and grabbed a handful of tissues, helping her clean up the large amount of cum sliding out of her.
_________
We kissed gently for a few minutes, neither of us wanting to get out of bed yet, but after a minute Sasha sighed and said “fuck okay let me go clean up, don’t go anywhere”. I laid back and closed my eyes as she wrapped up in a towel and slipped out of the room, letting my mind sleepily wander. I started replaying little moments from the previous night, recalling how fun and flirty Emma was … thinking about the game we all played … about our sexual conversation on the walk back … pretty much thinking solely about Emma.
As I drifted back to the edge of sleep, my fantasies became more dreamlike and more sexual, Emma being the star of each little sexual flash of imagery. Even though I had cum just minutes before, I could feel a little sexual energy building and my cock stiffening ever so slightly. Just as I felt the darkness of sleep starting to wash over me and my dreamy fantasies becoming more vivid, I heard the door softly open and close.
As Sasha crawled back into bed beside me, she slid her hand along my body, her fingertips drifting over my balls and shaft, giving it a little squeeze and tug as she said “mmm getting hard again … I turn you on that much?”.
Obviously not going to share the truth, I just nodded and groaned out a “of course baby”, pulling her bare chest onto mine as her leg draped over mine. We kissed a few times, her face slightly damp and smelling like her fancy face wash. After kissing for a moment longer she rested her head on my chest, both of our hands lightly touching the other’s body.
After some soft pillow talk, she asked me how the walk home went the night before. At first I just told her it was fine and mostly uneventful, but then I confessed how I told her the full story of our library quickie. Sasha asked “Oh, what did she say?”.
I truthfully responded, “She said it sounded really hot. I think she’s into you … she said she’s hooked up with girls before and seemed very interested in hearing about me eating you out.”
Sasha blushed a little, and in a tone somewhere between playful and upset said “Sounds like she might be more into you considering all you guys talked about was sex.”
If it weren’t for Sasha’s hands still lightly stroking around my abdomen, drifitng a little lower, I would have been worried I overstepped. Pushing back a little, I said “well to be fair that game of never have I ever was exclusively sexual, so it seemed to be the relevant topic”. When I continued with “she also said she wants to eventually have a threesome”, I felt Sasha’s fingers drift a little lower, now tracing the outline of my cock stiffening once again.
She asked hesitantly “like with us?”, a slight blush of embarrassment on her face. I told her that we didn’t explicitly discuss it, both of us just agreeing it sounded fun in theory, but added that based on how flirty she was with both of us it felt somewhat implied.
Feeling bold with Sasha’s fingers now stroking up and down my shaft, I asked her “I think I know the answer but would you be interested in that?”. She somewhat nervously and slowly nodded her head, her fingers wrapping around the base of my now hard-again cock. I told her “I want to hear you say it”, a grin spreading across my face.
She blushed again, and when she hesitated I rolled her onto her back, causing her to let go of me. I laid by her side, my cock pressed against her hip, and as my hands drifted to her breasts and traced circles around her nipples I reiterated “Are you fantasizing about a threesome with Emma right now?”.
She breathed deep, her breasts rising to meet my fingers, but when she stayed silent I slipped my hands lower and continued “close your eyes … are you imagining Emma’s fingers touching you right now … wishing she was kissing down your body … teasing your beautiful little pussy”.
She moaned and nodded in response as my fingers slipped between her still damp lips, rubbing small circles around her clit again. Her eyes were shut tightly as I continued touching her and asking her about her threesome fantasy, which judging from her bodies reaction she seemed to be loving. I sat up on my knees beside her, reaching to her nightstand to grab her eye mask she sometimes wore to sleep.
I slipped it over her eyes as I said “I need to hear you say it … tell me how much you’re fantasizing about Emma slipping between your thighs and tasting you”.
When she started to respond, telling me about how she wants to get eaten out while I suck on her nipples I leaned down and swirled my tongue around one. Her moans interrupted her sentence so I pulled back, telling her softly “Keep going”.
As she continued telling me about her fantasy, I gently sucked on her nipples and kissed her breasts. I reached across her body and grabbed the small pink vibrator that was still laying on the side of her bed. When I clicked it on and suddenly held it to her clit, Sasha moaned out loudly.
Wanting to stifle her moans, I sat back up on my knees and scooted towards her head. I grabbed her chin and tilted it towards me, leaning down to kiss her deeply, then whispered in her ear “I think it would be so fucking hot to watch you get eaten out while I use your mouth”.
She nodded and sighed, and when she took the vibrator from my hand and started using it on herself I kissed her again, then sat up and set the tip of my cock against her lips. Considering it had been inside of her less than fifteen minutes ago, when she swirled her tongue around it, I asked her “do you like tasting Emma’s pussy on my cock?”
She moaned an “mmhmm” in response, and when she parted her lips I pushed in slowly. She took my cock fairly deep down her throat before I found any resistance, and as I started facefucking her I continued fantasizing out loud to her, talking her through the fantasy of Emma eating her out, of being fucked doggystyle while she makes out with her, of eating Emma out after I cum inside of her.
That last fantasy sent her over the edge as she came again, this time shorter and sharper than her first. Seeing her body shake and watching my cock slide in and out of her throat made my orgasm start to build, and after another minute or two of facefucking her she reached her hands up and started playing gently with my balls. The sensation sent me over the edge, and I ended up cumming in her mouth, Sasha happily swallowing all of it and licking me clean as I slipped the face mask off her.
Both of our faces were a little flush, and as we both came down from the rather intense fantasy we kissed gently. I spoke first, telling her how hot I thought that all was. She agreed, and after sharing a few more deep kisses she spoke up “It was really hot to imagine you fucking someone else …” hesitating for a moment, “but if like we ever actually do have a threesome I think at first I wouldn’t want you to have sex with them, just like oral and hands till I see if I get jealous or not”.
I hid the small bit of disappointment I felt and told her I understood, reassuring her that we’d be smart about it and talk about ground rules if it ever came to that. After a little more pillow talk we figured we’d laid in bed long enough, and after I went to the bathroom and cleaned up Sasha headed to the bathroom to shower. Once I found my clothes on the floor and threw them on, I checked my phone for the first time that morning.
I had a text message from an unsaved number about an hour prior that read “Hey Ben, this is Emma. Just wanted to thank you again for walking me back last night and for such a fun night! Hope you and Sasha are having a good morning <3”.
I couldn’t remember if I had given her my number or not the previous night, and debated for a moment on how to respond. Replaying our conversation from the prior night in my head and remembering how flirty she had been, I decided to tease just a little and see if her drunk words were sober thoughts. I texted back “No problem, was great getting to know you better last night. Sasha and I had a very fun morning, no hangover and just now getting a late start to the day ;)”
I felt like it was ambiguous enough but could be read into, but also didn’t know how Sasha would feel about a text like that. I hesitated for a moment, but eventually thought “fuck it” and hit send.
I finished getting dressed just as Sasha came back from the shower and also got dressed. I had a lot of papers to grade for a class I TA’d, so after a few more goodbye kisses I headed back to my apartment to get my day started, not telling her about the text. Just as I stepped out of Sasha’s house to begin the walk back, my phone buzzed with a new text from Emma.
————
Okay this was getting long, so I’ll leave it there for now. I already have the rest drafted up and will post soon if there’s interest. Hope you enjoyed!