A tale of two convention roommates (F/M/M) | 2016

In my last post, I mentioned how my encounter with a Tinder acquaintance I'd made previously came about thanks to him seeing his roommate at the convention talking to me on his phone, but didn't mention any more about that roommate. Well, after matching on the first day of the event we'd continued to talk on and off, but to be honest it seemed like nothing would come of it - he didn't seem like the flirty type or interested in me in "that" way, and our conversations were mostly simple ones about how the convention was going and seeing whether we just happened to be at any of the same panels.

On the convention's final day, he messaged me once again, and after waking up late following goings-on earlier that morning I replied and we chatted again a little. He indicated that he'd really like to meet me before the convention was over, and I ideally asked him what he had in mind, expecting him to suggest meeting at a panel or for a drink. Instead, I got this: "We could go back to my room and I could make you feel good?"

My first thought was that he'd heard what I'd been up to with the friend he was sharing a room with, but from my probing to both of them during the remainder of the day they both denied it vehemently. Not that it mattered really - my interest was piqued, and all of a sudden my conversation with this guy had ramped up a few notches and continued to do so over the intervening hours.

In the meantime, I'd managed to drag myself out of bed, into the shower and then into my cosplay - Misaki Ayuzama's maid outfit, which is pretty much your typical anime maid outfit in black and white with black stockings and boots. Finally out of my room, I hunted down and caught up with my friends, and the day was spent hanging out with them having a good time. All the while however, messages were being sent to and fro - now between me and the two friends/roommates who were sharing a room at the convention. As I sought to cement some plans for later, things took some unexpected turns, but nonetheless I was all set to meet both of them at the final party of the event weekend, a fact which left me buzzing with excitement and a little arousal for the rest of the day once I knew what was ahead.

So, the evening came, and me and all of my friends headed to the party... sticking together for a while then ultimately drifting off in various directions around the party. Making my own excuses to head away from them, I swapped some quick messages and then eventually slipped outside of the party - there, I found both roommates waiting for me and chatting. The younger of the two I already knew from early that morning, so my eyes mostly took in his friend - much taller, much older (in his mid-30s compared to his 19 year-old buddy - anime fandoms create some unusual friendships), and decidedly uniquely dressed.. specifically, he was wearing a full girl's gothic lolita getup. Somehow, in spite of his age and height he wore it surprisingly well (and had a great eye for fashion it seemed) - this also isn't a particularly eye-raising sight at an anime convention, and to be honest it was refreshing to meet someone sufficiently comfortable to dress like that, upstaging even my most daring cosplay in a sense.

Anyhow, after some introductions (and reintroductions) we talked for a while - it was the older of the two men who drove the conversation, and he who asked if I wanted to come back to their room. With butterflies in my stomach I agreed, and everyone seemed comfortable and happy to head off for the short walk through the mild evening to the room. The three of us exchanged a little banter here and there, but were mostly quiet as we headed across the event's location to a dorm room building, then in through the doors and up a couple of flights of stairs. We entered a room larger and a little more luxurious than the one I'd been inhabiting, with twin beds and exactly the kind of mess you'd expect from two guys sharing a room together for a weekend.

Throwing items off the bed to the floor, the older of the two men invited me to take a seat upon his bed, which I duly did. He sat himself next to me, while his younger friend cleared a space to sprawl out across from us on his own bed. A brief silence was soon broken... "I've wanted you all day, it's been hard to concentrate", to which I could only nod and agree that I'd been looking forward to this too. With that confirmed, his hand snaked out to touch my leg, and he leaned in to kiss me.

We kissed for a while as his hand rubbed my leg and thigh, before moving higher, rubbing my black lace French knickers for a while before fumbling to pull the crotch to one side to gain access to the growing wetness underneath. He moaned a little into my mouth as his fingers found that wetness, rubbing up and down my lips while we continued to kiss and I opened my legs to give him easier access. Hearing some shuffling in the room, I opened my eyes a little to see his younger roommate moving to get a better view up my skirt, watching intently as his friend slipped a finger inside me.

He gently explored, fingered and rubbed me for a while, before pulling away and gently pushing me to lay back on the bed. Now on my back, he pushed the skirt of my maid dress up to my waist, kissing my stomach for a while before moving those kisses down over my panties, around my thighs, and then finally a hand reached up to pull the crotch of my underwear to one side again. Immediately, his tongue began to massage and explore me, and his technique was hitting all of the right spots. As I opened my legs wider, he firmly and confidently ate my pussy, stimulating my clit and making me moan. Hearing more movement, I peeked to see his friend now standing over us - keeping some distance but watching intently at his roommate's tongue working against me. I didn't focus on that for too long however, my thoughts instead drifting to my own pleasure, and it felt like no time at all before I was pushing my hips forward as my moans grew into cries as I reached an orgasm.

Giving me a breather to recover by kissing and stroking my legs and stockings, the older man whispered to me "tell me when you want me inside you", before returning to explore my pussy once again. He continued to lick and tease me, and when he repeated the previous statement I realised he was actually waiting for my affirmative answer. In need of more now, I looked down at him and voiced my desire "I want you to fuck me right now". With a few more laps of my pussy he pulled away, smiling. Standing up, he kicked off his shoes and reached up under his skirt and pulled down some surprisingly dainty female underwear of his own, which now free an erection which was leaving a clear tent under that gothic lolita dress.

That dress was then bunched up to reveal his cock in full as he clambered onto the bed, moving himself between my legs and taking his penis in his hand to rub it up and down my entrance. Sighing as I did so, both myself and his younger friend leaned forward to watch as he erection slowly worked its way inside me, each forward movement slipping him a little deeper into my wetness until I could feel his cock filling me.

Now comfortably inside me, he shifted position to press his body against mine, pushing my legs apart and up into the air as he did so. After a few gentle thrusts he began to build up the pace, and I started to moan again as he began to fuck me. As his movements became faster and harder still, I glance over to see his roommate moving around behind us before he disappeared out of sight, and I realised he was watching his friend's cock moving in and out of me from close behind, wishing I could see how my pussy looked being fucked from that angle.

He'd warned me before that it had been a fair while since he'd last had sex, and this older man was clearly enjoying fucking me, losing himself in the sensation. He fucked me rapidly, and it was just minutes before I heard him groaning "Oh fuck... oh fuck" as he thrusted harder into me then moaned even more loudly as he pushed deep into me and I felt streams of cum flow into my pussy.

We both laid there, breathing heavily, but rather than feel him softening and pulling out there was no real sign of his erection subsiding. Soon, I felt him moving cautiously inside me, then more firmly, and within a minute or two he was fucking me again as I wrapped my legs around him. Looking up at me, he grinned: "Don't worry, I'm not spent yet" he told me, fucking me harder as if to make the point. Meanwhile his friend still seemed to be watching the action from behind us, and again I wondered how it looked while my now cum-filled pussy was increasingly noisily fucked.

After a while he stopped again. "Why don't you turn around?" he requested, while pulling away from me and pulling off his dress to leave him naked. I did as he asked, at which point he asked me to move so that I was facing the other direction on the bed, which brought me face to face with his now rosy-cheeked friend who continued to watch silently, somehow restraining himself from masturbating too. Now on all fours on the bed, my skirt was pushed up again, and my knickers were finally pulled from my soaked pussy, down over my knees and to my ankles.

I felt the older man's hands on me, then his cock slipping easily into me. Again, he soon built up a firm and fast rhythm inside me, his body slapping against me and our combined juices being stirred in me to noisily accompany our fucking. Although my eyes were closed much of the time as I focused on the feeling inside me, on several occasions I opened them to look at the younger man watching over us - to start he remained watching my facial expressions, before moving off to the side to watch me being penetrated and ultimately kneeling on the floor to watch him fucking me from another angle. In spite of his detached, silent manner of watching me fuck, the bulge in his trousers told me that he was enjoying the view well enough.

For my part, I was certainly enjoying being fucked from behind, and once his cock began to hit the right spots inside me I was quite to let him know. "Like that... right there... don't stop" I moaned breathlessly, which caused him to start to pound me harder. This continued relentlessly, as my climax slowly but steadily built from within until I was certain that I was going to cum any time soon. Again, I was quick to relay this information... "Don't stop... I'm gonna cum", which led to him fucking me harder still, telling me to cum for him and to cum all over his cock until, gripping the bed, I did exactly that, moaning loudly and pushing myself back on him to prolong my orgasm until sinking onto the bed.

Panting and still moaning softly while I recovered, he joined me on the bed, pulling me onto my side and kissing my neck as he lay behind me. HIs hands traced my arms and legs for a while until, satisfied that I'd recovered sufficiently, he lifted my stocking-clad left leg in the air, scooting closer behind me and taking his erection in hand, feeding it back into my wetness. He fucked me slowly like this for a spell, while his friend returned to sit on his own bed, leaning forward and again intently watching where me and his older buddy were joined as he moved within me.

Pulling out, he invited me to ride him, although feeling rather hot at this point I only did so after undoing and slipping out of my maid outfit and also dispensing with my black bra. Now naked but for stockings and boots, I straddled him and quickly sank onto him, immediately beginning to ride him vigorously. Leaning over him he reached up to grope and suck on my boobs. I saw his friend move behind me and felt pressure on the bed - I suspect he was watching me being penetrated again, at which point his friend grabbed my ass to stop me moving and began to thrust up against me, fucking me hard. I felt the urgency of these thrusts increase, and shortly after "I'm going to cum again" he warned - sure enough, I soon felt him throbbing and cumming inside my pussy for the second time.

This time, his erection did subside, and I clambered off him once his softening cock slipped out of me. I lay back, wiping sweat from my brow while some of his cum seeped out of me and onto his duvet. I hopped up, excused myself to go to the bathroom and clean up quickly - once done, I exited the bathroom to find the older man waiting for me. "I'm going to grab a quick shower then head back to the party" he stated, "you guys take your time though". He ran his hands across my body a final time on his way into the bathroom, shutting the door behind him.

Returning to the room proper, the younger of the pair was there waiting for me - still fully clothed, still with a bulging crotch. I asked him how he'd found watching, to which his response was "That was the hottest thing ever.. now I really want to fuck you though". My reply to that was simple: "Where do you want me?" Guiding me over to the desk in the room he bent me over, pulled a condom from his pocket, quickly dropped his pants and was inside me as soon as the condom was in place. This was a frantic, desperate fuck, punctuated by his moaning into my ear about what he'd enjoyed from watching me - seeing his friend's cock moving in and out of me, seeing my face when I came, getting up close and seeing just how wet I was. With those images still running through his head and his cock thrusting in me, it was mere minutes before he came into the condom, pulling out to discard it. and flopping down onto the bed where I joined him.

After some more conversation our initial plan was to sit and wait for the shower to be freed up, but his friend's quick shower was proving to be longer than anticipated and our discussion about the evening's events was only succeeding to arouse him again. By the time the older of the two men had finished showering and dressing, he left the bathroom to find me leaning over his friend, whose pants were still around his ankles as I sucked his hardening cock. With a smile and a reassertion that he'd leave us to it, he was out of the door after a final glance over his shoulder at the scene, which prompted the younger guy to finally dispense with his trousers and underwear entirely before pushing me back onto the bed. Fishing for another condom, he put it on, spread my legs and tested my wetness before sinking back into me. This turned out to be another quick fuck, as he kissed me and thrust hard and fast into me until he couldn't take any more, pulling out and whipping off the condom so that he could jerk off and cum over my stomach.

Apologising that he couldn't last long with visions of me being fucked by someone else in his head, we both went into the bathroom and squeezed awkwardly into the shower to clean off. There were plenty of gropes and touches - both deliberately and inadvertent - as we showered under the hot water, and those touches ended with him kneeling between my legs and trying to go down on me. Unable to find a comfortable way for both of us to do this, I found myself led back into the room, still dripping water everywhere as he sat me on the edge of the bed, plopped in front of me and went to work with both tongue and fingers on me. Feeling a little sore at this point I implored him to stick to using his tongue and he duly did just that, licking and sucking feverishly on my clit until my moans grew into another orgasm. He was almost erect again by this point, but unable to take any more, I suggested we call it a day and we towelled off and dressed before returning to the party (although only after I spent some time outside to cool off and reduce my flushed cheeks.

The party went on for several hours after our return - once or twice I bumped into the two friends, who tried their best to hide their grins as we knowingly glanced at one another on the darkened, noisy dance floor. Eventually crashing in my room late that night, I awoke the next morning to a message from the older of the two men: "What's the next convention that you're going to?"