First Time with a Group [GROUP]

My husband read another post here about first times and so we had a few long conversations about different first times. He had a long relationship with the same girl from like 16 – 22 so all of his first everythings were with her. I wasn’t so stable back then so all my firsts were with different people. He liked my first slutty group-ish sex story the best, so after we talked about it he asked me to write it up and share it here.

This is with Dan, my first kind of shitty boyfriend type of relationship. We met at a house party, he was kind of dumb, but very good looking and wealthy. I was a freshman in college and he was a senior.

I used to party at his dorm a lot, like way too much. I lived in the freshman dorms and hated my roommate, but he lived in student apartments and shared a pretty big place with three other guys, and they all had their own bedrooms but shared a living room, bathroom, and kitchen. They were the party guys in the dorm and so every saturday it was a big party there and the RA’s didn’t really care.

So one normal party night it was chill and it was the weekend before thanksgiving so only like six people were around and we were playing this truth or dare game that incorporated strip poker. It went a few rounds and we were all in our undies. I rarely wore a bra back then so I was in a way to small thong I didn’t expect to be seen in, but did eliminate panty lines, and one of Dan’s tank tops and the other girl, Susie, was in a sports bra and bikini briefs – we were friends from track. The four guys were in boxers.

We were pretty tipsy at this point and it was probably already 2am or so. The game was setup so if you lost the hand, you choose hi/lo cards and the loser has to do a punishment from the winner or could refuse and draw a card. I’d already made out with Susie as punishment, which wasn’t really punishment, and when she lost she turned down the punishment of putting in a butt plug only to draw a card that said she had to masturbate in front of us all for 90 seconds. She made a show of taking her undies off and sat on the floor against the wall, spread her legs and spent 90 seconds rubbing her shaved pussy while keeping her eyes tightly shut. The guys were pretty impressed and since the rules were once clothes come off, they stay off, she was the first to remain fully naked.

We went through a few more rounds and one of the guys drew a masturbation card after turning down Susie’s punishment of making out with another guy. He was the only black guy in our group of friends and he dropped his boxers to reveal a semi-hard almost 9 inch cock that got a few wows from us all. He sat next to Susie and proceeded to get himself fully hard and spit on his hands and stroke himself. We were both fixated on his dick. It was the first uncut one I’d seen, and by far the largest. I got soaked watching him jerk off. The egg timer dinged and he sat back, hard cock pointing straight in the air, and a huge smile on his face.

As the next round went, everyone wound up naked but me due to the luck of the draw of the cards. Dan lost and had to make out with Susie on a dare from his roommate, clearly designed to make me jealous, and it kind of worked. They had to make out for 90 seconds with tongue and he clearly got hard in the process, I got a little heated, but played it off since I was pretty tipsy.

Then my luck turned for the worse, and I had to do a strip tease for everyone. So, feeling bold and a bit sexy, I spent a few minutes dancing around and taking my top off, and giving some quick lap dances before pulling off my thong and tossing it across the room. I was very happy to have just gotten waxed a few days before and when I was done, I bowed and got a laughing bit of applause.

Then I lost again. I turned down the butt plug and the card I drew said perform oral on the person to my right, which was Susie. With zero hesitation, she leaned back on the couch and spread her legs and laughed. I had hooked up with another girl at that point, so I had some experience, but it was a drunken thing and fuzzy, not that this wasn’t. So, I played fair and the timer started and I went to town. I dove right in and licked straight up her smooth pussy lips which were already a bit wet. I immediately found her clit and used my hand to push her hood up a bit and gave long slow licks right across it. She arched her back and let out an Oh god, and I tried to ignore my ass and pussy straight up in the air for everyone to see. I ignored the time and just focused on trying as hard as I could to make her come. She was getting wetter and wetter and holding the back of my head and breathing heavily. I could feel her stomach clenching. The timer dinged and she said, no no no, and held my head in place. Somebody said, I’ll allow it! And so I kept going, it wasn’t long before she was cursing and clenching her thighs against my head. She arched her back hard as she came then immediately recoiled, panting heavily. All the guys gave a joking standing ovation and I wiped my face clean with her undies.

Dan looked a bit shocked and had his hand on his hard cock. I sat back next to him and he put his hand on my legs, and I whispered, feel how wet I am, and pushed his fingers between my legs. I was dripping.

Then I lost a third time and was suspecting cheating. But, unsure what the cards held – I looked through the hand made deck before and it gets raunchy in there, I took Charley, Dan’s best friend and roommate, up on the butt plug he had been pushing for the last hour. He was shocked, but I’ve never been shy with plugs and own two. This one was one I’d never tried before but always thought was cool. It was a medium size rubber plug with a foot long fluffy fox tail extending from it. Charley handed it over, and without thinking of where it had been before, I used the bottle of KY on the table and with Dan’s help slid it in slowly as the others gathered to watch. Charley said part of it was showing it off, so I followed orders and walked on my hands and knees down the hallway and back. I got back to the couch and had to lay on my side. Susie let me lay my legs across her and she sat and petted and stroked the tail, which felt really nice.

I lost a fourth time and protested, but everyone showed their cards and it was fair. I turned down the punishment of having to walk, naked, plug in, to the end of the hallway and back and drew a card that said I had to bend over the knee of each player and take my spankings. I told everyone to be gentle, and I started with Dan, he gave me a few playful slaps on my ass cheek and smiled at me. Charley was less nice and pulled the tail aside and gave me two solid whacks that left a red handprint. The other two guys were bit more bold, rubbing my ass slowly before smacking it sharply. Charley took a picture to show me the handprints all over my ass. When it was Susie’s turn, she patted her lap, so I made a show of deeply bending over, she lifted the tail, tugging it against my asshole until it almost came out. She rubbed circles around my ass and sliding her fingers against my pussy. I braced myself and she slapped my ass hard enough to make me yelp and grab her leg. She gave me four very solid spanks and I was dripping. She let the tail go, and I rolled off her lap onto the couch. She was laughing and everyone told her she was probably next.

But, then I lost a fifth time and called bullshit. Dan said it just happens sometimes and we had to play fair. I knew I was being conned somehow, but couldn’t figure out how. Greg, our black friend, decided I could choose to pee on Susie or draw a card. Susie refused flat out thankfully, and so he switched and said I had to draw straws and give one of the guys a handjob. I debated in my head, Dan looked interested, so I said sure. Straws were quickly made and Greg was very happy about winning. He leaned back and spread his legs with a huge smile.

I grabbed the KY and drizzled a line of it down his shaft. I was on my knees in front of him, eye level with his huge cock. With both hands I worked the KY up and down his dick. Dan was resting his hand on my shoulder for some reason. I stroked it up and down, and ran my hands around his hairy balls. I’d never been with a black guy before, so this was a new one. He told me to use one hand and go shorter and faster, he rested his hand over the top of mine and showed me. I looked back and everyone was wide-eyed. I leaned in a bit closer to get a better grip, resting myself on his thigh, then I moved around and sat beside him, leaning over his body, basically 69ing without throwing my leg over him. He was running his hands over my ass and it felt amazing. He let out a small oh god, leaned forward and lightly bit onto my ass, and came hard. As he pumped his cum all over my hand and down my arm, he was kissing and nibbling on my ass. I turned and smiled showing him my cum soaked hand. Charley was already waiting with paper towels and helped clean off my hand, then I went to the bathroom to wash up. When I came out everyone was just staring at me.

The sixth loss in a row proved they were just fucking with me, but there was nothing I could do about it at this point since I really didn’t feel like leaving and was too tipsy to drive anywhere. Susie had won and decided an appropriate punishment was for me sit on a random cock for a full round. I weighed the options of the cards, and decided to take my chances. The card I pulled said almost word for word what she’d suggested and I knew cheating was going on for sure. I told everyone when I win the next round they’re all in trouble. The straws were passed back out and Charley won.

I moved over to where Charley was, and he was rock hard in anticipation. Dan was looking a bit shocked, but also a bit excited too. Dan handed me one of our condoms and I slid it on Charley, who was a respectable 7ish. I moved to pull the plug out, and he said no no, so I turned and lowered myself, sliding him slowly into my soaking wet pussy, and felt insanely full with the plug in and his cock inside me. He started grinding a bit and I turned and told him, no, rules say I just sit here and I clenched my kegels hard against him. I shifted around a bit getting comfortable while looking at Dan, he was a bit shocked looking, I smiled. I said we should get the next round going and suddenly everyone decided it was time to get drinks. So, as I sat there, full, they made drinks and talked and Charley squirmed against me, his open mouth resting on my shoulder and his hands around my hips, his fingers were playfully touching me, and I put my hand on his and moved his fingers to my clit while squeezing down on him. He quickly rubbed against me and flicked his fingertip against my clit, which made me squirm. Everyone was watching from the kitchen and whispering to each other.

They returned and I was still sitting hard against Charley’s cock, trying to hold still. He was trying to bounce his hips a little. Greg took forever dealing cards, slapping down one at a time, smiling all the while. Charley has stopped playing with my clit when Dan came back, but I was squeezing and releasing my kegels as fast as I could. He had his hands draped over my thighs, squeezing them a bit. The position I was in put a lot of side pressure on the tail plug, and I could feel it pulling out a bit every time I moved and it felt amazing.

Greg said the rules clearly said I played my hand from where I was, so I stayed put. For the first time in a while I got a great hand. I managed to win out, and I feel like I picked up the wrong cards. I stood up and laid back down on the couch leaving Charley with a rock hard, condom covered cock and a sad look on his face. Since he was also the loser, I told him the punishment was he had to draw straws and jerk off on the belly of the guy who loses or draw a card. No one looked thrilled. He immediately went for it though, and I knew the cards were rigged.

As Charley took off the condom, Dan drew the losing straw. I was thrilled and laughing. I made Dan lay on his back on the floor and had Charley straddle him. I told Dan not to worry and I’d help. As Charley started stroking, I took Dan’s cock in my hand and I stroked him slowly. He closed his eyes tightly. Charley reached down and was running his hand over my ass while he jerked off on his roommate. I nibbled on his earlobe and told him how hot this was. Within a minute or so, Charley came, shooting a huge load across Dan’s stomach, chest, chest and his neck.

As I was cleaning Dan up with paper towels, the next round was dealt and Susie declared it was her last. Greg agreed and we realized it was crazy late and we were out of wine anyways. So, Susie handed out cards with a smile and leaned back. I was suspicious, and I of course was dealt a horrible hand. Susie won and seemed surprised though. She decided a fitting punishment would be taking it in the ass from Charley, who fistpumped at the idea and pushed Dan jokingly.

Dan seemed uncomfortable so I went for the cards, which didn’t help. It said all players choose straws, handcuff and blindfold the winner and make them cum in under five minutes, if you win, the loser has to make you cum. You must stop at five minutes. That seemed complicated, but Charley produced handcuffs and a blindfold and passed out straws. Greg won with a huge smile and announced there’s no way he’d be able to cum in five minutes since he just did.
Charley said I’d have to give it the old college try as he blindfolded him and laid him on the floor by the sofa. He then handcuffed his hands in front of him. Greg had a floppy, but already semi-hard dick, so I was a bit hopeful. I heard someone start the timer as I leaned over and kissed my way across Greg’s neck and down his chest. He put his cuffed hands on the back of my head. I kissed passed his dick, down to his feet, kissing his ankles and calf, then slowly back up. Then I took his half-hard cock into my hand and licked and nibbled the sides before licking the head. He made a groan and was getting a bit harder.

I used my spit to lube and stroke his shaft just the way he showed me and he got hard pretty quick. As I picked up the speed and tried to not gag on his cock, Susie called out that I had 60 seconds left. Greg was starting to squirm a bit but I was losing hope. I took him as deep as I could into my mouth without gagging. He was holding the back of my head firmly and thrusting his hips against my face, but no luck. The time dinged and Charley took off his blindfold. I was panting heavily and Greg looked a bit bummed. I had spit and precum all over my face.

Dan announced the game was over and we called it a night. Charley and I cleaned up, Dan went to his room and sulked. An hour later Dan broke up with me and said I was a slut, I was too drunk to drive, so I slept in Charley’s room. Charley and I ended up dating for a year after that and Dan was super shitty to me every time I saw him.

Source: reddit.com/r/gonewildstories/comments/a4uefh/first_time_with_a_group_group