Threesome at the Anime Convention
Introduction:
Hi, my name is Jay. This is the story of the first time I’d ever been with two women at once. It is 100% true, and happened at the San Japan anime convention here in San Antonio a few years back.
We hit it off pretty much right away, and it wasn’t long before our idle conversation turned into a playful banter, then a constant flirting back and forth. I wasn’t sure if it was going to go anywhere, or if it was just playful flirting. But I didn’t much care, because we were both having a good time.
After a couple hours of this flirty chat, I had to go off for the first shoot I’d scheduled in the day, and she off to change into her costume and walk around the con for a while before meeting back up to shoot together close to the end of the day at 5.
The day went by quickly, and before I knew it, our scheduled time rolled around. I hadn’t seen her costume, just knew that she was cosplaying as Harley Quinn. When she showed up, my jaw nearly hit the floor when I saw her. Tight red and black leather pants, stiletto length heels on her knee high boots, and a red and black leather corset that was so tight her tits were trying to escape. The tanned skin of her tight, toned mid drift glistened with sweat, in San Antonio’s August heat. She noticed my eyes lingering, and giggled, giving me a bit of a spin. The leather pants did a great job of showing off her perfect ass, which was being pushed out a bit by the heels.
“Whatcha think?” she asked, still a bit giggly.
“I think you’re the most beautiful Harley I’ve ever seen.”
She smiled at that, and popped up on her toes to give me a peck on the cheek. Even with the heels, she was a good 4 inches shorter than me. “Thank you.” While she was up there, she leaned into my ear and whispered, “You ever ride a Harley before?” She stepped back, devious grin on her face. Her bluntness was a bit of a shock considering how timid she was when we’d first met. But that accent of hers was such a turn on that I could feel a bit of blood rush down to my dick.
Not knowing how exactly to respond, I just smiled at her. “Umm… Shall we get started?” I asked, waving my camera around like an idiot. We handled the legal stuff, contract signing, verifying her age again, (she had just turned 18 about four months prior). She asked me to give her a rundown on how to pose, since she’d never done a shoot before. I did so, and even explained the flashes and other equipment when asked.
The shoot itself went well. Being the last shoot of the day, we ended up going over our half hour slot, and shot for about an hour and a half. At the end of it, as I was packing my gear into my camera bag, she said, “Are you going to the rave?” Every year, this con held a small rave each night. Something I’d always wanted to go to, but never had the chance.
“I can’t, I’m not staying downtown this year, so I have to head home while the buses are still running.”
“You can stay in my hotel room, if you want… I think it’d be really fun if you came.” I could see in her eye that she was planning something. I figured, why the hell not? Gotta live life while you’re still alive right? So I agreed.
We walked around the con for a while longer. The main halls were closed, but there was still stuff going on elsewhere. Eventually, we made our way up to her hotel room, on the 21st floor of the Hyatt, so she could change, and I could set my stuff up to charge my cameras batteries for the next day. As I was plugging them in, I realize that she’s stripped right there in front of me. I turn around, embarrassed, but she spoke up. “What, am I not pretty enough for you? You couldn’t take your eyes off of me earlier.”
“I’m a photographer, and you were posing for me. The shots would all be shit if I didn’t look at you.” I responded.
She laughed, “Don’t think I didn’t see you staring at my ass, or tits.” Her voice got louder as she approached, and I felt her hand on my shoulder. She turned me around, (though I didn’t make any effort to resist). I looked her up and down, smooth toned skin, her tits perfectly round, her thin waist forming an hour glass shape to her body. Her pussy was waxed smooth. She wasn’t even up to my shoulder, small, and perfect in every way.
On her tip toes, her hands grasped my cheeks, pulling me in to kiss the softest lips I’d ever felt. My arms wrapped around her, each hand gripping an ass cheek. After making out like that for a short time, she pulled back, and looked deep into my eyes, she said. “I’m horny, and I haven’t had a cock in a while.” I could feel my dick hardening, pressing against the inside of my pants while she spoke. Her hand crept its way down to the front of my bulge, and wrapped around as much of it as she could. “So I’m going to drain you empty with my mouth, and once you’ve recovered, you’re gonna fuck me so hard they hear my screams down in the lobby.”
With that, she dropped to her knees in front of me, unbuckling my belt as she did so, and pulled down my boxers and my jeans both in one swift motion. My dick, hard enough it could’ve cut diamonds, sprung out to attention so suddenly that it smacked her on the bottom of the chin. “Jesus fucking Christ!” she yelped out in surprise. She leaned back, gazing at it with wide eyes, and licked her lips.
Now, I’m not what I’d call huge, as I’ve certainly seen bigger in porn, and in real life. But I’m just a bit over 7 inches long, which from what I’ve read, is around average. But I am fairly thick. Thick enough that her small hands couldn’t wrap all the way around it.
She looked up at me, with her hands on my legs. “You’re gonna fucking split me in half with that thing.” The difference in her language now, versus the somewhat timid girl I’d met just that morning was a bit of a shock, but such a big turn on.
She leaned forward to lick the tip. I could feel my cock twitch at her touch. She moved her head past, licking her way down the shaft until she reached my balls. She glanced up at me, my cock resting across her beautiful face, her cheek skin felt soft as velvet. Without saying a word, and without breaking eye contact, she licked all the way back up my cock until she reached the head, allowing it to enter her mouth, and taking all 7+ inches down. At the base, she lingered, I could feel the pressure of her throat constricting around m cock. With a bit of maneuvering, she managed to fit my balls in her mouth as well. This is the point where she started to gag, but at no point did she let up. Her arms reached around my body, and I could feel her hands on my ass, pulling me forward, forcing her face further into my body.
Just as I thought she might suffocate, she released me with a gasp. A long string of saliva stretched from my cock to her chin, and her eye shadow had started to run a bit. She took her left hand, and started stroking me, my cock looked so much bigger in her small hand. Her right hand grabbed her phone from the night stand. Curious what she was going to do, I said nothing. She quickly took a selfie of her, with the tip of my dick in her mouth. I heard a the swoosh sound that indicated she sent the picture to someone, all this while continuing to stroke me.
Once the photo had been taken and sent, she tossed her phone, and with that hand, reached down to undo my shoes, and told me to kick them, as well as my pants, over to the side. I did as instructed. She went back to sucking me, not gagging herself quite as much, but humming to herself, the Pokemon theme song. I couldn’t help but laugh to myself, but god did it feel good. I took my shirt off, tossed it, and ran my fingers through her hair, eyes closed in pure ecstasy. After about ten minutes of the most amazing blow job I’d received up to that point, I started to feel like I was about to explode. Just as I was going to tell her to slow down, I heard another voice.
“Oh shit!”
I turned to see another girl, maybe a couple years older than Jess, (I later learned she was 21), short black hair, bright blue eyes, small C cup tits, long legs, thin figure. She stood there, dressed as cat woman, (comic books, not movies), whip and all, just staring me in the face, silent. Jess pulled my cock out of her mouth with a loud popping sound, and turned to see her friend. Cat woman’s eyes quickly drifted from me, to Jess, then to my cock, and just as I was about to try and cover up, I felt it, and let out a grunt. Jess turned her attention back to my cock, just in time for the first spray of my load to splash against her nose, and all over her left eye.
She let out a yelp, followed by a giddy squeal, as I pumped the biggest load of cum I’d ever produced, into her face. It lasted for what felt like forever, all the while I was as good as useless, having to brace myself on the wall, for fear of my legs giving out, and collapsing on Jess. Her friend stood in silence, watching.
As soon as my cock had released its last bit of the cum onto Jess, she leaned forward, sucking the last few drops out of the tip. She stood up with a huge smile, face covered in cum, a lot of which had dripped down onto her tits. Her eye still stuck shut from the cum. With her fingers, she wiped her face off, feeding it to herself. She turned to her friend, who had a hungry look in her eyes.
“Hi there Al! How’s your con been going so far?” Jess let out in a bubbly tone.
“Holy shit! It didn’t look quite as big in the picture.” Her friend, whose name I eventually learned was Alex, replied.
Jess slowly walked over to Alex, cum still dripping it’s way down her tits. “Well, I left a bit of that massive load for you, if you’re feeling hungry.”
At this point, I was sure my knees were going to give out. I just couldn’t believe it when her friend leaned in, and started licking Jess’s tits, sucking up what was left of my cum. Jess turned back to me with what I’d come to know as her signature grin. “Why don’t you have a seat on the bed. Take a breather, and enjoy the show.” I said nothing in response, for fear of waking up. I just nodded, and did as instructed, not taking my eyes off of what was happening in front of me.
Alex had finished cleaning off Jess’ chest, and turned to me with an approving expression. “Mmm, tastes so sweet. Glad you eat healthy.” She turned back to Jess. “Where’d you find this one?”
“Shut the fuck up and kiss me.” Jess responded, aggressively pressing her face into Alex’s.
The two stood there, making out in front of me. One buck ass naked blonde, and one black haired beauty in a leather cat suit. Jess’s hands roamed all over her friends body, and eventually located the zipper at the nape of the neck, and slowly, even sensually, pulled it down until a bra could be seen. She unclasped the bra, which came together in the front, and a perfect pair of tits popped out. Jess’s head wandered it’s way down Alex’s neck, and then to her tits.
Alex looked over at me, her friends face buried between her tits. Noticing I was already hard again, she said. “You just hold tight and stroke yourself to stay hard over there. We’ll be with you in a bit.”
I again, did as instructed, slowly stroking my cock without comment. It was still wet with Jess’s spit.
Jess slipped Alex’s catsuit and bra over her shoulders, and slowly down her body. As she reached Alex’s panties, she hooked her fingers over the lip of them, and pulled them down as well.
As Alex stepped out of it, and kicked it away, I saw she had a thin strip of black hair above her pussy. She was very fit, hints of a six pack forming, as well as muscle definition on her legs and arms. Obviously someone who worked out a lot.
Since she was already down there, Jess just buried her face into Alex’s pussy, shoving her tongue as far in as she could. At the time, Alex had her eyes trained on my cock, so she hopped up a bit in surprise at the feel of Jess’s lips, but quickly settled down, and let out a soft moan. She hung her right leg over Jess’s shoulder, and leaned back against the TV stand behind her, spreading her left leg out a bit to give Jess a better angle, and me a better view. They stayed in this position for a few minutes, and I slowed my strokes, not wanting to cum by my own hand with these two naked goddesses in the room.
Alex pulled herself off of Jess, and reached down to wrap her hands around Jess’s arms, pulling her to her feet. She brought her over to the bed, and threw her down on her back near the middle of the bed at my feet. Jess’s tits bounced, as she giggled happily, her legs hanging off the side of the bed. The look on Alex’s face as she stared down at Jess’s soaking pussy, is to this day the most pure lust and hunger that I’ve ever seen in my life.
She positioned herself between Jess’s legs, and burred her own face in that inviting, smooth pussy, licking up all the juices. On first contact, Jess let out a gasp loud enough that I’m sure if anyone was next door they haired it. Her eyes rolled back in ecstasy as she bit her lip, and gripped the bed sheets.
After a minute of this, she turned her head to me and commanded just four words I will remember till the day I die. “Come fuck my face!”
I didn’t have to be asked twice. I crawled over to her, my knees on either side of her head, my balls resting on her forehead. Before taking my cock back into her warm mouth she said, “Don’t you dare think about holding back. Fuck me with all you have, I’ll let you know if I need up for air.”
I looked to Alex, who returned my look and said, “You heard her… Deep throat fuck that pretty little face like we’re all going to die in the next five minutes.”
I looked back down to Jess, still unsure how hard she wanted me to go. I leaned forward, hands resting on the bed on either side of her hips, and slowly pushed my dick into her mouth until my balls were on her nose. The sizes of my shaft and the inside of her throat was so different that there was a noticeable dick shaped bulge nearly all the way to where her collar bones met. Alex had a massive grin on her face, Jess’s juices dripping off her chin, watching me.
I pulled back out to where jut the tip was in, and then back down to the base of the shaft, a bit more forceful this time. Jess let out a muffled moan of pleasure, and Alex nodded in approval before going back to the still soaked pussy in front of her. I pulled back, and thrust back down her throat, faster with each thrust. Her left hand gripped my wrist, and her right hand formed a thumbs up to let me know she was still alright, and enjoying it.
I started getting into it more and more, essentially force fucking her face. Hearing my balls slap against her nose, looking down to see her tits flopping about, hearing her moans.
Alex pulled back out of her meal, and made her way up, kissing me, thrusting her tongue into my mouth. I could taste Jess’s sweet nectar on her lips. She pulled back, and said. “Eat her pussy while you fuck her face.” She then proceeded to put her hand on the back of my head, and force my face down into Jess’s pussy. It was the sweetest thing I’d ever tasted. Alex circled around the end of the bead and started to smack my ass while I fucked her friends face.
Eventually, Alex now just sitting on the bed watching us while fingering herself, Jess started to convulse, and I felt her pussy tighten around my tongue. Her muffled moans got louder as she was cumming, and I knew that had my cock not been so deep in her throat, she’d have let out those screams for the lobby that she’d asked for earlier. I slowed my pace, and after a minute or two more, she tapped my arm. Taking that as a sign that she needed a break, I pulled back out of her mouth, and climbed off of her. She lay there gasping for air, massive grin still on her face. “That was amazing!” She let out, once she’d caught her breath. I collapsed, also out of breath, cock still rock hard. I’d been close to cumming when I pulled out, so the breather was appreciated.
Alex handed me a water, and Jess a towel. As I downed the whole bottle in one drink, Alex said, “Don’t get to comfortable, I want a taste of that juicy cock of yours. Just lay back and relax, I’ll be more gentle than Jess was.” I settled back, leaning on the headboard of the bed, pillow under my mid back for support.
Jess plopped down next to me, still smiling. She leaned up and gave me a soft, tender kiss, in shockingly high contrast to what had just transpired. She whispered, “Thank you.” and rested her head on my chest, and looked down at Alex, who was crawling up, spreading my legs apart.
As she lay on her belly between my legs, Alex wrapped her hand around the shaft of my cock. Her hands were bigger than Jess’s, but not by much, as her finger tips were still not able to touch her palm. She leaned in, and took just the tip of my cock’s head in between her lips, and sucked with enough force to siphon gas out of a car. I still, to this day, have felt nothing like it from anyone else. She slowly slid her mouth halfway down my cock, continuing the suction, while her left hand stroked the rest of the shaft, and her right hand played with my balls. A true master at multitasking.
She pulled my cock out of her mouth, and kissed the underside of the shaft, halfway down, sucking on it. She continued to do this to each ball individually, and every inch of my cock, paying special attention to the tip of the head. She took me back into her mouth to continue sucking. She went slow, and every time she felt a throb that might be a sign of me getting ready to cum, she would stop, letting me settle down a bit more, making it last as long as she could. After continuing to edge me for a long time, she looked up at Jess with a grin, who sat up, having sufficiently caught her breath.
“Is it time?” Jess asked.
“It is.” Alex responded.
Jess clapped, and bounced up and down, back to her perky, giddy self. “Who gets to do it?” she asked Alex, who had sat up on her knees, between my feet.
“You found him, you do the honor.” Alex said, as the two of them crawled to change places, pausing long enough to give each other a light kiss as they passed. “Scoot down.” Alex told me, as she reached her place next to my shoulder.
I once again, did as instructed, scooting down far enough for my feet to be just at the end of the bed, and my head resting on a pillow. Cock standing erect like a pole missing it’s flag. Jess leaned down, and kissed either side of the head, as though greeting it. With that done, she swung her leg over, and hovered just over my cock. Alex reached down, taking it up in her hand, to help guide Jess in for her landing.
The head of my cock pressed against the outside of Jess’s small pussy, until it was forced in by all 95 pounds of her weight pressing down against it, Alex holding it sturdy with her hand the whole while. She stopped just below the head, and let out a whimper. “Holy fuck, it’s to big!”
“You got this Jess, just breath, and power through it.” Alex said with the supporting tone that an Older sister might have. “It’ll only be painful for a short time, and then it’ll feel better than anything you’ve ever experienced.”
“It’s not the pain that I’m worried about, you know me, I love the pain. I’m worried that either something in me is going to rip, or I’m going to cut off the blood flow to his cock.”
Alex spit into her palm, and stroked my cock, wetting it. She turned her head to me and said. “Help her out. Make it quick.” Taking direction well, like I had before, I moved my feet, bending my knees for leverage, and thrust my pelvis upward, ramming the entirety of my cock deep into Jess’s tight pussy.
Jess threw her head back, and screamed, before leaning forward, hands on my chest, as I settled my ass back down onto the bed. She sat still for a time with me inside her, adjusting to the size, which I later learned was larger than anything she’d had in there before. I was proud of that.
After a time she slowly started to move around, allowing my cock to slide in and out. Hers was the tightest pussy I’ve ever fucked, and god did it feel great.
“That’s my girl, look at you go!” Alex said as Jess straightened up, riding me faster. Tits bouncing up and down, hair flinging about like a head banger in a mosh pit.
She started really getting into it, biting her lip, and grinding on my cock in small circular motions. “You like me riding your cock like that?” She asked me, looking deep into my eyes.
“Fucking love it.” Was all I managed to say in response. I rested my hands on her legs, rubbing them up and down, over her tight belly, and up to her tits, squeezing them, using them as leverage to her down onto me harder. I turned my head to see Alex watching, fingering herself with her right hand, playing with her tit with the left.
Realizing they were doing all the real work here, I decided to help them both out a bit, and sat up enough for Alex’s right tit to be just at face level, and took it in my mouth. She yelped in surprise, as I gently bit her erect nipple. My right hand slid its way down Jess’s belly enough for me to rub the top of her pussy with my thumb, pressing down. She apparently loved this, based on how much louder she got.
I continued sucking on Alex’s tit a bit before deciding that after taking direction this whole time, it was damn time I gave some. “Sit on my face so I can eat that pussy of yours while she rides me.” She looked down at me in what looked like surprise, but this didn’t last long before she turned to straddle me. “No.” I said stopping her. “Face her. You two are going to make out while you’re riding me.” I said it with force to impress the point that I wasn’t asking. This position was on my bucket list, and I was sure as shit going to cross it off.
She turned and smiled at Jess, who had slowed down a bit, watching this exchange. “I really like him, he should come back to Cali with us.” She turned back toward Jess, swung her leg over my head, and lowered herself down, hovering just over my face. She leaned forward and started sucking on Jess’s neck. At this point, Jess was no longer bouncing, but was simply sitting on me, balls deep, fully engrossed in the wonders Alex was working on her. I didn’t much mind, since I didn’t want to cum yet, and the brief pause was enough for me to settle down a bit.
I was impressed by how much heat was emanating from Alex’s pussy. It smelled sweet, like a tulip. My arms wrapped around her legs, my hands grabbing her ass cheeks, spreading them apart to give me a clear view of her surprisingly beautiful creamy white asshole. I pulled her down to greet her soaking wet pussy with my eager mouth. I could hear her let out a gasp as my tongue entered her. Her juices tasted as amazing as they smelled, and I was in heaven licking them up.
The three of us formed a perfect triangle, as Jess slowly started bouncing up and down on my cock again. All three of us moaning in the purest of ecstasy. We continued like this for another thirty minutes at least, before I heard both of them say in unison, “I’m about to cum!” I pulled my face out of Alex’s pussy long enough to confirm I was about to as well, and heard Alex respond through short raspy breaths, “I want you to cum in her pussy!”
I wasn’t able to form a thought, or even respond, as we all three reached climax together. Jess convulsing on my cock, which was pumping so much cum into her pussy that most of it was being pushed out all over my balls. Alex, straddling my head, began to shake as well, as she leaned forward to lick up a mixture of mine and Jess’s cum from around the base of my cock, as she released her sweet orgasmic juices onto my face. Our moans and screams formed an orchestra of pleasure.
Jess fell backward between my legs, my cock popping out of her pussy, flinging my cum through the air with enough force to splatter some on the ceiling above us, as well as plaster Alex’s face and hair. Alex slowly slumped to the side, freeing my head.
The three of us stayed there like that panting for the longest time, before I simply start laughing. “Holy shit, this has been the best convention I’ve ever been to!” I manage to say through the laughter.
Alex laughed as well, and sat up, looking like she’d just ran a marathon. “Hi, I’m Alex.” She said, extending her hand to shake mine.
“Jay.” I said, returning the handshake.
“Well Jay, the con’s not over yet, this was just day one. I assume you’re staying with us all weekend, right?”
“Stupid fucking question.” Jess said as she was sitting back up. “You saw how he fucks, of course he’s staying here all weekend.” She stood, stepping off the bed, hand cupped over her pussy to keep its contents from spilling out. “I’m gonna go clean up. You guys are coming to the rave with me right?”
I’d completely forgotten about the rave. I looked at the bedside clock to see it was nearly midnight by now, a few hours into the rave. Jess made her way to the bathroom, waddling with her hand between her legs. “I’m down. Might be fun to blow our friend here on the dance floor.” Alex said, patting her hand on my now flaccid cock. She gathered up what cum had pooled on my waste, and held it in her hand, looking me up and down. “But I think, we all need a shower first.”
“Already on it!” Jess called out from the bathroom, as Alex and I heard the spray of the shower start. “You two gonna come join me?”
Alex looked at me with a grin, and licked my cum up out of her hand. “I don’t think I’ll be able to handle a marathon like that again for a while.” I said, almost as if to myself.
“Don’t worry powerhouse, you can relax and wash us off while we make out in the water.” She said climbing over me, and taking my hand to lead me into the bathroom. She glanced back at the bed to see the mess we made. “Shit, house keeping is gonna be working over time to lean this up… Gonna have to leave them a big tip.” She said with a laugh.
The three of us showered together, thanks to the large bathroom in their suite, me washing them up, them washing me up. I got a quick blow job from the two of them at the same time, since my cock decided to perk up again at their touch. We eventually made it to the rave, for the last few hours it was happening, and I sure enough did get a quick blow job from Alex out on the dance floor. It was a thrill having people watch.
I spent the entire weekend with them, and save for the times I had to go handle photo shoots, we didn’t spend much time at the convention. Last year, they both came back for the con, bringing another friend with them, and we all shared a room again, and we’re planning the same for this year. And even though the sex with either or both of them is always amazing, nothing will ever be quite like that first time. Alex still calls me “powerhouse” sometimes. lol
While the situation with these two has become a yearly thing, it wasn’t my first ever random sexual encounter at a convention, and it certainly wasn’t my last… But those stories will have to wait for another time.
