8. Friday Night – Group Anal Fun
Comments are appreciated.
Warning: contains some lesbian and bisexual content.
Disclaimer: This is a work of fiction. All characters involved in sexual activity are at least 18 years old. Any resemblance to real people is coincidental. Of course, if your name is Kyle or Juliet, please feel free to pretend this is about you.
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Juliet
Oooh, that Kyle. I love that boy’s body and his kinks. And. Well. His prick. Long. Hard. Thin. And it feels fantastic in my cunnie and my ass. If Alex lets me.
I was just spiraling up the slope to a huge bang of orgasm, fired by Big Pinkie buzzing in my cunny and Kyle’s thumb way up my ass. I was moving up his body, hoping to get his tongue there, too. That would have set me off. Fireworks!
But then, bitch Alex interrupted my “massage” session with Kyle, shoving me off his oiled body.
OK, if I was Alex, and Kyle was my boyfriend, I would be insanely jealous, and I would have shoved me off his hot body, too.
But, Alex is not that way.
“Get dressed,” she said. “Get out and warm up the person outside. Save your cum for later. Your turn for blue balls.”
You should know: Alex is not a jealous girlfriend. First, there is the fact of Alex and Kyle. Eye-rollingly committed lovers. Like epoxy glue, together. She is not jealous. Neither is he.
So, I started to look for clothes. I thought, why not hook some stuff from Kyle’s roommate, Dan? He was gone for the weekend. Hell, that’s why our little group was in his room. Dan’s chest of drawers had some gym shorts. I picked silver nylon.
Second, Alex really enjoys group stuff, group butt stuff, and she uses Kyle as bait to rope in new partners and to try out new ways to fuck.
I found a long T-shirt, too.
Third, Alex is diabolical. She loves fucking with your head, and especially, the parts of your head where there are kinks that you, yourself, don’t know about. She loves to uncover those… secrets… and use them.
Woah. Dan has some kind of whitish silk robe in his closet. I dropped the T, kept the silver shorts for modesty, and then wrapped the robe around me, nippy nip bra intact.
By the way, that’s how she conquered me in high school. Butt licking. Who knew I had that kink? And now, Alex and I are roommates in college!
I dropped my phone in the robe pocket and opened the door. Alex closed it behind me and locked it.
I was standing in the hall of the men’s dorm section, mostly naked under a borrowed silk robe. My cunny was still overheated and squirmy-liquidy from Kyle’s efforts. And, I was on a mission from Alex to seduce someone waiting out here for later inclusion in our butt-stuff big game tonight.
But. Who? I looked around and there were no suitable candidates.
Then, Dan walked out of Tim’s room. Aha! I thought: Alex has assigned me easy prey.
I lounged where I was at Dan and Kyle’s door, just undulating a bit as I telegraphed “cum fuck me” in my best body language. Dan and Tim both tripped down the hall.
“Hi, Dan,” I said. “Thought you were having to leave to go to your Dad’s place this weekend?”
Dan looked to Tim, “Umm, Tim invited me tonight. We were going to play Ensorcelled, but Jason decided to go on a pub crawl with the inter-mural baseball dinks. So, we didn’t have enough folks to play.”
Tim said, “Yeah, we had a special campaign and everything.”
“So, now what are you doing?”
“We were just… I dunno. Nothing, I guess.”
“Sounds boring,” I said. “Hmm. Well, I could play a game with you, but two conditions: 1) you have to teach me the rules and 2) I get to decide what the prizes are for winning.”
The two boys looked at each other. “Well, Ensorcelled is kinda complicated. It takes a long time to get all the rules, and stuff,” said Tim.
“Are you suggesting that I am too dumb to figure it out?” I asked. I knew that would stymie their little brains.
Dan quickly responded, “Of course not. It’s just that the game takes a long time to master. And, it wouldn’t be fair for you and me and Tim to play, since we would just win all the time.”
Dan, of course, like usual, did not know when to shut up. Suddenly realizing he had put his foot in his mouth, he stopped abruptly. At least he had the decency to blush.
“Ok, then, you bastards,” I said. “Let me pick the game. It will be a simple one. I think both of you could master it in seconds.”
They looked at each other, again stupidly. “Um, what game, then?”
“Let’s go in your room, Tim. And, um, is your roommate here?”
Dan looked a bit stricken. Tim quickly answered, “No, Charlie is almost never here and he is not here this weekend. So, no.”
“OK, then, let’s see your room, Tim.”
We traipsed back down the hallway, into Tim’s room. On the way, I glimpsed a familiar face just entering the far hallway. I think it was maybe Jocelyn. But, I dismissed that out of hand. Why would our floor’s biggest lesbo be hanging out in the men’s wing on Friday night? Nah.
Tim had a bunch of beanbags, almost like lazy theatre seating, arrayed in front of this gigantic flat-screen TV hung on the wall. I don’t know how he got permission from the housing authority to drill the holes and stuff. Maybe I would ask him later. It was playing some sports channel and I immediately thought, what a sad contrast. Tim’s body was about the full opposite of jock — tall, yes, but gangly, thin, a bit pale, and not very muscular.
Dan, by contrast, was a much more appetizing morsel, and I had been working on getting a few bites at his cherry over the past few weeks. Alex had introduced me to him — she said it was some kind of emergency, but with Alex, who knows? Anyway, we had gone out a couple times, but Dan was slow slow slow to recognize fairly obvious signals. Naive? Yup. But cute.
And although I had not yet seen his dick, I was hoping for something interesting and, um, hard. Soon.
I keyed Alex, “Starting on warm up. Dan and Tim. Tim’s room.”
“Dan? Tim?” she texted back.
“Give me a while,” I replied. I put the phone away.
The two boys had slunk into bean bags and were starting to go through their Ensorcelled cards. I needed to stop that shit in its tracks.
“Hey, Tim. Um, do you have any, um, interesting. No. Stimulating… substances to share?”
“I don’t smoke,” he said. Dan looked stricken by the idea of mind-altering substances.
“Edibles, then?”
He smiled sheepishly. “I’m an art major, right? Yeah, and I guess there is enough to share.” He went to his chest of drawers and extracted a small box of goodies.
“Dan, you too,” I said. “All of us are in this game together.”
We unwrapped the gummies, and each savored a sweet jell. I ate only a small part of mine and palmed the rest. Weird flavor, like blueberries? Tim had some unusual source, I guess. Yeah, art major.
I knew it would hit Dan hardest, he was probably a virgin on this, too. The boy needed to relax a bit. He was overly tense, particularly recently.
“Ok, what game, then?” asked Tim.
“Lock the door,” I said. I looked around meaningfully. “This is a game for us three. I want us to get to know each other well, so it is going to be simple questions. At each point, we will randomly select one person, and the last person that answered a question, will be able to ask the next person one question. OK? Everyone needs to tell the truth in answering. Some of the questions might be a bit, um, embarrassing, but,” I shrugged. “That is the point of the game. Do you agree?”
The two boys looked at each other. “Is this Truth or Dare?”
“No. It is just… Find. Out. About. FOA. For short.”
“What kind of dumb game is that?” asked Tim.
“Yeah, I never heard of it,” said Dan.
I rolled my eyes. “Are you guys telling me that you don’t understand the rules? I said I would make up a game that you would be able to figure out in seconds. Do you not understand the rules of the game?”
“Yeah, we get it. But what is the point? It doesn’t sound very fun,” said Tim.
“The point is to get to know each other better, like, friends and stuff. And, I will decide what the winners will get as prizes. OK?”
“Um, OK. What are the prizes?”
“I will have to decide on prizes later, OK? Right now, let’s do a show round of questions. OK?”
“But first, we need to set the mood. Tim, you have a candle or something? Just for lighting.” He rummaged and found some hideous stump of wax, and lit it. Cherry. Whew! I wanted to hold my nose. “Dan, will you open the window? It’s too stuffy in here.”
I got up and turned off the lights. “This will be better if we can do it in semi-dark, a bit more anonymous and less embarrassing maybe. I will start with a question. Dan and Tim, you guys pick a number, between 10 and 30.”
“12.”
“16.”
“Fine, I was thinking 18. So, closest is…” Yeah, I know that this is not random selection. We will see how it plays out.
“Dan,” said Tim.
“OK, Dan, what is your major and why did you pick it?”
–/–
It took a while, but the edibles helped, and the boys were discovering interesting things about their pasts. I had kept my answers relatively benign, for example, about my prior boyfriends and such without too many titillating details.
I also gradually took control of the questions.
–/–
Dan giggled. “Really, Tim? You stole that stuff from the drugstore?”
“Shhsh,” said Tim. “It was only a tube of lube.” He giggled, too.
“Hot jell lube,” giggled Dan again. “I bet that wasn’t the best for jacking off.”
Tim giggled again, “No. It was too hot to handle!” More laughter.
I asked, “Tim, where did you use the lube?”
“In my bedroom, at home.”
“No, where on your body, you bozo.”
“On my dick.” Both boys giggled.
“Was it slippy dippy?” asked Dan. It was clear the edible was having an impact.
Tim laughed.
I wanted to move this along. “Not on your butt? Tell the truth.”
Dan giggled. “On your butt? Tell the truth.”
“OK,” said Tim, “Just a little on my butt. But damn, that hot stuff was really hot.”
“Dan, answer the question. Have you ever put lube on your butt?”
Tim giggled, “Yeah, have you?”
“No, why would I?”
“Tell the truth.”
“Um, maybe once? I had to get an enema when I was little.”
“Ok, then, good answer.”
“Now, we are going to ask some more embarrassing questions, are you ready?”
Giggles. “Time for embarrassing!” said Tim.
“OK, Tim, when was the last time you jacked off?”
Dan giggled. “Tell the truth. Tell the truth.”
“Um, maybe five hours ago.”
“Where did you squirt your cum?”
“I put it in the Kleenex. It’s in the waste can over there.”
“OK, Dan, same question.”
He laughed, “Yesterday morning. In the can. I put the cum on the toilet roll.”
“Bozo!” said Tim. “In the can? Anybody could have come in there and seen you.”
“Oh, just fuck off Tim. You have a room to yourself. I have to find my own space, OK?”
I interrupted. “OK, boys, next question. Tim, what does your cum smell like?”
“Doh. It smells like cum.”
“Is it sweet? Sour? What?”
“I dunno. Not sour, not sweet. Just kind of… creamy? It tastes like cum.”
Giggles.
“Ok, new question, Dan, which of you has the longest dick?”
Tim asked, “Hard or soft? That makes a difference.”
“Let’s start with soft.”
Dan answered, “That’s not fair. Tim’s dick is always half chub hard.”
“So, Tim has the longer dick when it is chub? And you have never seen it soft?”
“Nope.”
“How about when it is hard?”
“I dunno. We never compared hard dicks.” Giggles and pointing between the two.
“OK, boys, here is a possible prize. I will give the winner of the contest a chance to feel my boobies, for 2 minutes. Are you interested?”
Dan perked up, “Sure!” Tim was a bit more subdued. “OK,” he said.
“Here is the question, then. Which of you two has the longest dick when it is hard?”
“How will we know?” asked Tim.
“You have to tell the truth, dummy,” said Dan. He was a bit inebriated, and perhaps a bit more stupid about this kind of thing than normal.
“Look, I will get started,” I said. “I am going to come over to you, between you. You can take one hand to touch my boobies. One hand each. You can use that to think about and to get hard. I will measure your dicks, OK?”
I sat between the two boys, propped on bean bags. I opened my robe and pulled a hand from each of the two into my chest. Once those hands were working, pulling at my nippy bra and weighing my breasts, I reached into their clothed crotches to feel their boners.
“Hey, take these off,” I said, pulling at the waistbands of their pants. “I need to see this, to make a good comparison.”
The hands disappeared from my tits to take off their shorts. Tim’s boner was a bit soft, not really paying attention. Dan’s boner was hard and curved a bit.
At last! I have his boner in my hand!
“OK, boys, it’s kind of difficult to get a good comparison. Stand up, and let’s put them side by side.”
The boys stood, face to face, and I held the two penises in my hand, over and under.
“Dan, push closer.”
Sure enough, the head of his dick touched Tim’s belly first. “Looks like Dan’s dick is longer.”
Interestingly, Tim’s dick grew noticeably harder while I was holding the two penises together.
“Wait a minute, let’s try that again. This time, Tim, you push,” I said.
“Looks like they are both almost exactly the same size,” I concluded. “So, here is the winner… I am going to give the first prize to Dan. You stand behind me, and you put your hands on my titties. You can do what you want.”
Dan was giggling, “I can do anything?”
“With my boobies. OK?”
He moved behind me, and somehow, in the process, the silk robe fell to the floor. His hard dick was bouncing on my back, my buttocks, not quite in my butt crack, but maybe hinting at it.
“Tim, you get a different prize, OK?”
“What?”
“Come here,” I said, and pulled him by his dick toward me. “Where is your lube, now?”
He pointed over to the chest of drawers.
“And your condoms?”
He pointed again.
“Good boy. Go get them. And the lube. And come back here.”
Dan was going to town on my titties, pulling at the nips, lifting and dragging my boobs, hands wandering up to my neck and down along my belly. The fluttery feel was starting to cause my cunny to get interested, and I could feel a bit of flush along the skin of my chest.
I reached behind me to grasp his hard dick. “Dan, your dick feels fantastic. Really good to me.”
He grunted back to me, “Thanks, thanks, no one has ever told me that before.”
Tim returned with lube and condoms. I took the lube. “Put a condom on.” I squirted lube onto my fingers.
Tim rolled a rubber down his dick. I pulled at the newly shrouded prick, bringing him close to me. I then reached around, and slipped my lubed fingers between his butt cheeks, in search of his hole.
He gasped as I penetrated the first knuckle of my pointer finger in his bunghole. “Found it,” I said.
Tim’s dick shot out, record hardness, with his dick pointed upward at about 70 degrees — nearly vertical.
“Now, Tim, put a condom on Dan,” I said.
Tim moved beside me to go to his friend. I reached into his butt crack as he passed, and inserted my finger further into his hole. “Wait, You need to pay the toll first before you go further.”
I jacked the lubed finger in and out of his bung several times, then I spanked the end of his dick, right on the rubber reservoir. He had backed his ass up onto my probing finger. This boy liked ass-play.
“OK, toll paid this time. No refunds.”
I stepped forward, away from the two, watching Tim eagerly reach for Dan’s dick, while Dan stood there a bit befuddled at the absence of my boobs and ass. It was clear he didn’t quite understand the task I had set to Tim.
I decided to take a big risk, given the responses from Tim so far, and the confusion of Dan.
“No, Tim. Put it on… with your mouth,” I commanded.
Lo and behold! Tim sucked in Dan’s dick, and Dan’s eyes closed in shock? Pleasure? Pain? Surely Tim wasn’t hitting him with teeth?
Tim rolled the condom fully down Dan’s dick with repeated strokes of his mouth.
Now that I had gotten Dan this far, I didn’t want to lose the whole scenario. I knew that Dan was really a mental virgin, and jeez, boys can be so so sensitive about the homo stuff, right?
But, really. This guy had seen Tim, naked, repeatedly with a chub. And didn’t think maybe maybe Tim was gay? Or at least bi? Gah. Idiot.
“Tim, good boy. You, lay down here. Face up.” Tim obeyed compliantly, his boner now standing straight up from his skinny belly and blonde pubes.
I slipped off the silver nylon shorts I had stolen from Dan, and stood over Tim’s face, facing toward Dan, with my legs spread with naked cunnie and hidden bunghole right over Tim’s nose.
Standing, I pulled Dan to me, and kissed him hard, pushing my tongue in his mouth. He responded ardently, flicking his tongue in my mouth, across my lips.
“Fuck Dan, you make me so hot! God, you are beautiful. I love your cock, I want your cock.”
He bent over to take my nipples in his mouth, tonguing around the little metal clips.
“Juliet, I’m a virgin,” he mumbled into my ear. “I… I don’t want to…”
I whispered back to him, “Your dick is so so beautiful. You make me hot.”
“I don’t want….”
I whispered back in his ear, “Should we stop? We can stop if you want. I will fuck Tim then, is that what you want? To watch me fuck Tim?”
“No, I don’t want to embarrass myself. You know… cum too early or something.”
“You won’t. If it happens fast that is no problem either. I love your dick. And your body. And I really like you. You’re cute. And I could eat you all up.”
Tim was fapping away at his dick, peeking around my legs to look at Dan’s boner.
“Hey Timmy. Get your hand off your dick. No cheating,” I ordered out loud.
I whispered in Dan’s ear, “Even if you cum fast, we have time. We can go again and again. OK? Ready?”
He nodded. “Fuck yeah. I want to fuck you tonight.”
“Good, I want your dick.”
–/–
Kyle
After Alex interrupted Juliet from her near-orgasm, I watched with bemusement as the girl wandered a bit aimlessly, searching for some kind of coverup to go outside into the hallway.
I laughed inwardly as Juliet rifled through Dan’s drawers and closet. Somehow, she had found a gay-looking white silk robe. Why in the hell did Dan have that thing in his closet? I rolled my eyes.
Alex was watching Juliet, too, hooded eyes carefully gauging her minion’s mindset and willingness to follow direction. Tonight was a bit complicated. And, Alex was leaving out a lot of information, so she was relying on Juliet to understand the heart of the directions, without having to micro-manage.
“Hey, love, come on down here,” I said to Alex. “Juliet has this under control. And, you look all tense and stuff. I think,” I motioned to the massage set up on the bed on the floor, “That you would benefit from a relaxation massage right about now. Just let Juliet do her thing.”
Alex opened the door, Juliet slipped out, and then Alex re-locked it.
As she stripped naked, my little head was doing leaps of excitement followed by tiny squirts of precum. “Fuck yeah, you are so hot, Alex. I want to just um. I dunno, Eat you up. Fuck your holes. Make you scream. Rock your orgasms.”
She giggled. “Aren’t you articulate tonight. And here I was expecting French poetry.”
I laughed in return, “I’ll show you French poetry.” I grabbed her around the naked waist, and turned her sideways, her long dark hair blllowing out and highlighting her olive skin as I twirled our two bodies in a circle.
“Put me down,” she commanded.
I ignored her request, twirling her another round.
“No, come on Kyle, don’t hit my head on the furniture. Idiot.”
“Sorry. But not sorry.”
I laid her gently, face-down on the massage sheet, arranged her limbs loosely with her arms at her side and her legs slightly spread. God, I wanted to find that pussy and asshole and go to town with my fingers and tongue and prick, but I knew that part of Alex’s plan this evening was to tease tease tease. So, I refrained from my little head’s urgent requests to fuck fuck fuck.