[Group] A Truth or Dare Memory Gone Good

I’ve been wanting to write down a few memorable stories for some time and I was finally able to complete this one. It’s my first attempt at writing erotica, though I do get some practice on /r/dirtypenpals now and again. This is a true story from almost 20 years ago. I’ve tagged it group, but the sexy parts are all paired off MF partners.

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“Dare,” I replied confidently, taking another risk in the slowly escalating game.

The girls put their heads together, giggling. They were a little drunk from the vodka, but not out of their minds. This was planned; maybe not the reason the game was suggested, but they didn’t take long to come up with their dare. “You two- kiss,” my girlfriend Jill said suggestively pointing at my best buddy who was sitting on the bed, bemused by the whole evening unfolding in front of him, at least up until this moment.

“Umm..” I replied, my face twisting. The girls burst out laughing, Rachel, Jill’s college roommate buried her face in my girlfriend’s shoulder. Matt’s face turned sour. My best buddy through our teens was here on the trip to ride 4th wheel with Rachel and catch up on old times. We’d been through a lot together, but our lips touching wasn’t something that had happened nor was it anything on the weekend’s bucket list.

“Come on, you have to, Drew. It’s how the game works!” Jill teased, putting her hands on my chest, and looking at me devilishly with her big brown eyes.

I wasn’t sold but the wheels in my head were turning. I looked at Matt and shrugged, “I mean, they can’t dare us this, and not expect what they’ll get in return, right?” He shrugged knowingly, which is why best friends are best friends. Within a 2 second look we imagined everything that could happen the rest of the evening, simply by putting our faces together. Little did we know at the time, we probably didn’t imagine enough.

As our lips touched and quickly broke apart, the girls giggled, but quickly called foul. “That was not a kiss. That was just your lips touching. Redo it!” Rachel emphasized. I rolled by eyes, but leaned back in, this time lingering for just a moment, so our lips took the other’s in. The girls were still not satisfied, but accepted our effort as Matt and I backed away, wiping our mouths and shaking our heads.

While the girls were still laughing, I turned to Jill quickly, too eager, really. “Ready for your dare?” She laughed playfully and shook her head insisting on a “truth” instead. “Pussy,” I muttered under my breath laughing at her reply. She’d pay for that.

The game progressed but eventually Rachel chose dare and it was clear what was coming. “You two kiss,” Matt and I say, almost in unison. The girls rolled their eyes at our horniness but leaned forward. It dawned on me later that it sure didn’t look like the first time they’d done this, though Jill insists it was. A quick peck this was not. The roommates locked lips. Their hands gripped each other’s bodies, pulling them in close. Rachel held Jill’s cheeks softly as their mouths explored – tongues intertwining. Matt and I watched in awe for a good 20 seconds as our girls french kissed passionately. Finally, Jill pulled away, flushed. It didn’t seem like Rachel was done, but the moment had to move on. I remember noticing Rachel’s hard nipples, poking through her t-shirt. “Fuck.” I commented, as the girls awkwardly giggled.

The next memorable dare was even more interesting, and again, suggested by the girls. The intentions of the weekend were clear- pairing off as couples. I had been dating Jill for quite some time, over 2 years at this point. Matt and Rachel on the other hand, had just met a few hours earlier. I had known Rachel for almost a year, but only really as “Jill’s roommate” so casual hellos and conversations here and there, but nothing more. Honestly, she seemed so quiet, reserved, and shy, but here she was driving this game further. “The dare is to swap partners for a kiss. Matt and Jill, Drew and me.”

This didn’t bring the game to a screeching halt but it did force a moment of reckoning and levity between myself and Jill. We looked at each other, sharing our own private conversion with a look. Can I kiss her roommate? Can she kiss my best friend? Will it be weird afterwards? Do we really want to watch that happen?

Jill shrugged, “Okay, but we do it in separate areas. Matt and I will step into the bathroom. You two here,” she said motioning to the bed area. “30 seconds.” We all looked around, and nodded, giggling. I guess it was on.

No, I don’t think Rachel had a secret thing for me. I think Rachel was just horny from the game, and the naughtiness of the situation, but damn, did she pounce. The second my girlfriend and Matt rounded the corner, she leaned into me, falling on top of me on the bed and our mouths connected.

Her lips were the softest lips I’ve ever kissed. The way she used her tongue was mind blowing. My cock went from excited by the whole situation to instantly full of blood, her slender sexy body I’d never really noticed before, grinding against it. My arms wrapped around her body and I pulled her in tight while we shared one of the greatest sexual 30 seconds of my life. She was an amazing kisser, there is no other way to say it and the whole buildup of the situation still ranks this as one of the top 5 kisses in my life, easily. If anything, it was a little too good, because what happened next broke up the game. Rachel and I certainly weren’t timing, but apparently our kiss was a little more intense than Jill and Matt’s kiss. They came out of the bathroom laughing awkwardly, to find Rachel and I still connected fully, her straddling me, grinding her hips against my erection while my right hand was cupping her small breast, teasing her hard nipple through the fabric of her t-shirt. Whoops.

The game of Truth or Dare dissipated quickly after this, but the drinking and sexual tension did not. The party rolled on into the evening as we shared drinks, laughs, and general silliness. Jill and I were able to share a quiet moment or two and it seemed no harm was done with the game. We had both enjoyed ourselves, we agreed, though she did joke that after sampling the room, Rachel was clearly the better kisser, and based on what she saw, it seemed I agreed.

The night finally started to wind down- at least the part of the night with lights on and group socialization, but the wildest part of the evening was still to come. We were sharing a room, with two queens, the joys of being poor college students, so bedtime meant pairing off as couples but sleeping just feet apart from each other. The thing though, there was a lot of alcohol, and a lot of sexual tension; sleep apparently was not on the menu.

As the lights turned off the room went silent, at least at first. Within minutes though the room started to fill with the soft clear sounds of lips touching, of tongues exploring. Jill rolled on top of me, laying flat against me, kissing me passionately, deeply, and drunkenly. I was wearing a t-shirt and gym shorts while my hands were all over her body above and beneath her shirt and thin cotton shorts. I groped at her ass and back as we smooched. I let my mouth move down to her neck and ears as she tried to hold in her moans while she slowly grinded her body against my erection poking against her stomach.

“Listen,” she whispered, stopping and laying still against me, letting her face rest against my neck and chest, our hearts beating in unison against each other. My ears perked and heard the sounds from 5-feet away, Matt and Rachel joining us in a late-evening activity. Like Jill, Rachel was on top, and we could hear their lips smacking, their tongues darting in and out of each other’s mouth as they furiously made out. The room was quite dark but it wasn’t hard to hear the rustling of the sheets and the slight struggle from Rachel as she wiggled out of her t-shirt, the end process emphasized by the sound of the fabric being tossed on the floor in the small space between us. “Holy fuck,” my girlfriend whispered as I reached for the bottom of her shirt and pulled it quickly over her head, getting her as topless as her friend beside us.

Now that it seemed our neighbors sharing a bed just to the left of us weren’t going to feel awkward and alienated by our horniness, the night continued, a strange and surreal escalation of auditory voyeurism and a strange can-you-top-this competition. More clothing was peeled off and tossed on the floor. Moans were less withheld and discretion was generally gone. Within minutes all four of us were mostly, if not fully naked, our hands were exploring freely, and while the room was very dark, our eyes adjusted and we could make out the shapes of what was happening in each bed.

While my focus was certainly on my girlfriend in bed naked with me, my mind was racing wondering how far Rachel and Matt would take things. Hardcore making out is great, but these two still really only met each other a few hours ago, though they were clearly hitting it of swimmingly. There were two factors I was considering which were both interesting to my drunken brain. The first is that while Matt wasn’t a virgin he also wasn’t the most experienced as far as I knew. To that point, I would’ve guessed Rachel was much more conservative as well, though she was proving that theory wrong. Secondly, and admittedly much more of my mind’s focus- I wondered how she’d handle his cock. I’d never seen him hard, but we grew up playing sports together and in locker rooms and other situations, well, there is no way around it- he is hung. Even if what I saw swinging just got stiff it’d be an adequate tool. Assuming some proportional growth, Rachel was going to have some work ahead of her. Based on how Jill was looking over, her head laying on my chest watching her roommate intently, it seemed her mind was on the same thing.

Jill laid flat and still on top of me, our naked body’s melting into each other’s and our breathing synced. My arms wrapped around her, slowly rubbing her neck, down her back and to the tight flesh of her ass. We laid like this for minutes, while our friends passionately hooked up and we watched their dark shadows pressed together and listened to their bodies connect. We saw Matt grab Rachel’s small frame and pull her up further to his body and listened to her moan as his mouth greedily attached to her nipple. Jill’s body shifted as she started grinding against mine looking for the slightest friction for her needy pussy. I could feel the heat radiating from her and my cockhead was wet from the inevitable precum I was leaking along with the fact that it was resting firmly against her opening. I caught my breath in my throat as Jill slowly twerked her hips into position and slowly and tantalizing lined my cock up fully. We tried to withhold our moans but failed in unison as my cock filled her pussy.

Jill slowly and rhythmically started moving her hips as she laid flat against my stomach, massaging my cock with her pussy as we watched Matt’s mouth all over Rachel. We watched him push her body around in his big hands, moving her to where his mouth wanted her. His lips and tongue smacked greedily as he sucked her tits, back and forth, a popping sound when he pulled his mouth off her nipple. A sigh from her followed by a quick moan as he reattached himself to her body almost instantaneously. The newness of them exploring each other seemed to make them oblivious to us, that we were watching and the show they were putting on for us. We could see Rachel wiggling her body against his as he kissed her; begging for friction and the touches needed to get off. A small moan squeezed from Jill as I flexed my cock inside her, a move she reciprocated with the tight grip of her kegel muscles on my dick. The heat forming between our naked bodies slowly fucking and being mashed together started to build, and i gripped the comforter pulled up over us, and shoved it down the bed, the coolness hitting us like a blast, now only a thin white sheet and darkness hid us from our roommates.

Rachel was in bliss but pushed herself away from Matt with a little grunt using his chest as leverage. We saw the silhouette of her breasts, hanging down, swinging gently, her nipples hard like little pebbles at the end of a perfect fleshy teardrop. Still, she didn’t look over at us, on a singular mission of pleasure, she started sliding down his body. She quickly reached his midsection, sliding under their bed’s sheet as she did so, though it slid down leaving Matt body exposed to his navel as well as her head. She gripped the sides of his boxer-briefs and pulled them hastily off. He helped her by shimmying his legs and helping her kick them off and the underwear was quickly discarded in the shared middle pile. In the franticness of getting him naked the sheet shifted and Matt’s cock was briefly revealed in the darkness at which point I literally felt Jill’s pussy spasm briefly, squeezing my dick, still buried inside of her in 3 or 4 mini love hugs. Rachel quickly slid back up to Matt cock, pulling the sheet up over her head, gripped the base of his cock, and attempted to put her mouth over the tip. A groan of pleasure escaped his mouth and as he started reveling in the pleasure his head turned to the right on his pillow and he noticed us watching.

He didn’t seem bothered by this, certainly not enough to stop getting a blowjob. Whether it had crossed his mind at any point up to now, I can’t say, but between being drunk and having a new mouth exploring his cock for the first time he just sighed content and enjoyed the pleasure. I really don’t know how much he could see in the light of the room but a quid pro quo seemed in order and Jill didn’t protest as I slid the sheet down her back to waist level, her body still pressed against mine. “Sit up, ride me,” I whispered, a little moan escaping her lips as she complied, pushing off my chest and exposed her nakedness to him. She used my chest as leverage as she slowly rocked, riding me slowly as my best friend watched.

Time started to lose meaning. I’m sure it was minutes but it felt longer. Jill riding me, while I played with her exposed tits. The sounds of rhythmic sucking as Rachel administered a blowjob Matt certainly seemed to be enjoying. Little grunts and moans here and there from all of us. My cock felt so good in my girlfriend but I wasn’t going to be the first person to cum. I reached down, gripping Jill’s hips and pulled her off me while shifting my body off my back and turning her over to hers. The sheet was momentarily ignored and in the shadows our naked bodies were briefly exposed. I hovered over her briefly sucking her breasts, nuzzling in her armpits, and giving her soft quick kisses down her flank. I kept shifting down the bed until I found my spot between her legs, pushing them apart for the access I desperately needed and greedily pushed my face into her just-fucked pussy.

She moaned. I moaned. I always love eating pussy but I don’t always get the rare treat of doing so this soon after a fuck. There was already so much of her cum, the way only a 20 year old can be and I could taste the unique rawness of the pH changes of her pussy post-cock. I pushed my tongue through her folds, my tongue broad and flat to make as much contact with her as possible. Each stroke of my tongue ended at her clit- not focusing on it but making sure it received the full brunt of pleasure. I pushed my tongue inside her, mashing my nose into her clit and reveling in the taste of her inflamed vaginal walls. She smelled and tasted amazing. My hands held her legs, holding them apart while I ate her pussy slowly. Little moans escaped her mouth when my tongue hit her clit just right. Jill’s right hand was in my hair, gripping tightly, guiding me around to the perfect places she needed my tongue, her left gently teasing and playing with her left nipple. The sheet was barely covering my head and I was able to look up and see her head turned on the pillow watching our bedroom partners. I’m sure Matt’s head was turned too, watching my girlfriend topless, while he was getting head.

I finally stopped teasing and transitioned my licks into a predictable rhythm allowing Jill’s orgasm to build. I was a little higher on her now, my tongue going through her folds and ending on her clit, and then back down. My nose was pushed into her well-groomed but hairy bush, a style which was not popular, but that I adored and requested. I could feel her body tensing followed by quick moments of relaxation. She was still trying to generally be quiet despite what was clearly happening on each bed in the room, but moans were softly humming from her lips. I could tell this was building to a monster orgasm and one I didn’t want her to hold back on. As I felt her body tense up, nearing what I knew to be the final seconds before cumming, I quickly took the index and middle fingers of my left hand and pushed them swiftly into her pussy, while focusing my tongue now entirely on her clit.

She exploded. “Ohhh Fuccccckkk!” she moaned loud enough for people on the other side of the walls to hear, unable to hold back. She gripped my hair tightly thrusting her hips into my face now as she rode my tongue through her orgasm. “Don’t stop,” she begged. Just as this was happening, Matt lost it beside us, a big grunt a clear signal that his cock was unloading semen into Rachel’s dutiful mouth. Matt and Jill had their orgasms together as Rachel and I slowed our oral assaults, letting them each finish.

Almost in unison, Rachel and I each slid up the bed back up beside our partners, and collapsed in our beds beside them. The room was now silent except for heavy breathing, for a few moments, before Jill broke the tension in the room with a simple, “Fuck.” We all giggled.

Now that the awkwardness dam was broken we continued the evening of fun. Over the course of the night each couple drifted in and out of sleep as well as in and out of sexual activity. Jill blew me for a little bit, though she much prefers to let her pussy do the work. My cock ended back up in her a few different times through the course of the night, cumming in her twice. Rachel and Matt continued to explore each other’s bodies. As Jill and I slept we were doing so with sounds of them kissing all over. Even with adjusted eyes we still only ever saw silhouettes and shadows of activity, which in retrospect to the evening actually makes it more fun. To this day, I don’t know if they fucked or not, but they certainly had fun. Matt definitely received another blow job, cumming again. At one point he performed oral on Rachel, but it didn’t seem to last long and she didn’t cum from it. We did hear her orgasm once but it was while she touched herself with my best friend’s cock in her mouth. Rachel clearly got off on giving, certainly an admirable quality trait in all aspects of life, and something I’ll always have tucked away about her.

The next morning and day were fairly normal. Not shameful per se, but the light of the day and the removal of drunkenness brought levity. Covers were pulled up. Towels were used. Privacy respected. Jill and I did take a shower together though it wasn’t filled with sexy time as much as a chance to be alone for a moment to wash, and just check up on each other to be sure what happened the previous evening was okay. We agreed it got pretty wild but nothing we could do about it now, and it happened with the right set of friends. Rachel and Matt showered separately, something he groaned over slightly, but he knew not to push his luck. We went about our day normally and had a fun time exploring a new city. Rachel and Matt held hands and playfully kissed through the day but it was clear this was a one-time hookup of happenstance. After that weekend I’m not sure they ever contacted each other again.

Jill and I have more adventures, many in fact. We eventually married and have been together for 20 years. Most of our wild days are behind us. This didn’t kick off some sharing kink or dipped toes into any sharing lifestyle. It’s just a wild event that happened when we were 20. I think she is still friends with Rachel on Facebook, though as far as I know they haven’t communicated directly in years. I see a post from her occasionally as well- still put together, now with a family and can’t help but look at her smiling lips knowingly.

Source: reddit.com/r/gonewildstories/comments/inoehp/group_a_truth_or_dare_memory_gone_good