Breaking new ground (a little m+m, a lot of m+f) | 2016

So I was talking with another guy on a different sub, and he was wondering if I had had any bi/groupsex esperience. I've done quite a few different things through all my phases, but this one was a bit of a challenge, and the following story is as close as I have to the request. (Also, this led to a lot of good memories, if you guys have any other questions or fantasies feel free to pm me or leave a request in the comments. Chances are I've done something close.)

Quick shout out to /u/mxxw for the request!

"Matt (me), this is Liz (2nd gen Pakistani immigrant), wanna head downtown tonight? I have some friends coming out" the text read. Liz and I met a few nights before at a house party. She caught me a little bleary eyed after I found out my girlfriend had another boyfriend. Don't worry, she's an ex now.

Aww fuck it, I thought, finishing off my second whiskey coke of the night, I have nothing else to do, better go out hard. "Yeah sure, where are we going?" She texted back the name of the place. I'd never been there before, thought I remembered something funky about it, but I figured I'd give it a shot. I throw on my nicest jeans (a little tight), a cream colored button down shirt, with a darker brown cashmere sweater over the top, and some nice boots. I have this thing about dressing to leave good impressions. I don't think I've ever given a physical description of me, so here goes. I'm about 5'9", and weigh 190. I have a weightlifter / boxer's physique. Very stocky, wide shoulders, long arms, short legs. I think my build is goofy but if you're into chest/arms/back then I'm your guy. I have short hair, about 1.5" long and it's spiked in the front. My beard is about an inch to an inch and a half, and very full (consistent, no patches, well maintained. I get told I look like Zach Galifinakis when I let it grow out). Pretty quickly, I was at the bar, and saw her and a few of her friends on the way in. "Drag show - Tonight" the marquis over the front door read. What did I get myself into.... at this point in my life, I had never been to a gay bar before.

I catch up with Liz and her friends, and she gives me the quick introduction. Between the drinks and shots at home, I was already a little buzzed. I offer to pay for some drinks for the folks around anyway, as a polite gesture (protip: it makes friends), but before I know it, a drink is in my hand and one of the guys is chatting me up. Role reversal is an odd thing, I've never been hit on at a bar before now, usually I was the one making moves.

"So, are you here with Liz?" He asked.

"She invited me out, I didn't have much better to do," I replied, adding a chuckle, "I've never been to a place quite like this." The crowd erupted as one of the queens took off her skirt on stage. I laughed a little uncomfortably.

"Wait... Don't tell me. You're not gay, are you?" He said. I was still in shock because of the environment, the openness, and now sexuality being brought up within five minutes of meeting someone.

"I'm not, well, I've never tried anything like it," I stick the drink in my mouth, not wanting to offend or anything like that.

"Oh just relax, I'm not gonna jump you," he said, and patted my shoulder. We went on to talking about other things, and Liz came by to make sure we were still doing okay. She had a coat on earlier, but now I could see she was in a strappy little blue tight dress. She is maybe 5'1 and comes right up to my chest.

"Why didn't you tell me Matt is gay?" he shouts, loudly to Liz, while smacking me on the ass. My eyes bulge and I try not to let my drink fly out of my mouth.

"Now wait one min-," I start -

"No he's not, I have a pretty strong feeling about this one." She winks at me, that type of wink that you want to read so much into, but figure it's just her fooling around. "Glad to see you're getting along," she says quickly, excited to see a new friend arriving.

I turn back around to the bar, and order another drink while finishing the one in my hand. We talk about Liz, her dress, how I know her, how he knows her, etc. Finally, we get back around to the topic of sex, how many partners (male/female) and we were both a little shocked at each others number.

"You know what I think? I just don't think you're comfortable enough with your sexuality to be with a guy." The challenge was laid out. I cringed a little, and had a feeling this was going to come up at some point or another.

"I'm actually very comfortable, and I know what I like..." I said, peering back at Liz. That dress probably wasn't long enough, but I didn't mind too much.

Maybe it was a combination of drinking too much before, the breakup, or just generally not caring, but I didn't bat his hand away when I felt it crawling up my leg. "Wow, you really aren't gay, are you?" he laughed as I was completely soft. A quick glance showed that he wasn't going to be standing up for a while, his erection VERY clear. "What did you expect? I'm not into guys." "Well, look at her, then!" he said quietly, but firmly. I turned back to look at Liz and caught her eyes, staring at me. He continued to pet my pants, and I slowly but surely got harder and harder until he could grip it. Liz was talking with another person, but clearly and obviously glancing at me every few seconds.

"I'm so mad you're not gay, I want your dick," he said. Liz finally caught a glimpse of his arm, and where it was going... I blushed and pushed his hand away very quickly. I paid for my drinks, thanked everyone and said it was nice meeting them, then started to head out.

"Hey wait, where are you going?" It was Liz. "You're not good to drive, let me drive you back." Seeing how I dropped my keys about three times on the way to the door, I figured it would be a good idea.

We get in the car, and a few seconds of awkward silence pass. "So, you and Brent...?" She inquires.

"Nononononono, he was just, uh... testing me." Awkward chuckles followed.

"I never had a chance to ask..." She started.

"Nope, I'm not gay. That was the first time a guy has ever touched me like that."

"So you'll like this...?" Her hand reached across the car, and started petting me. Almost instantly I was hard, and her hand was grasping it. She pulled the car over, and I had to help her undo my belt. Our hands were all over each other. Mine went from her legs to her waist to her chest, and she gasped when one hand was on her neck. She kissed down my body and wrapped her mouth around my cock. It was so warm and wet compared to the air outside. We struggled a little bit to get her jacket off, as it was quickly warming up inside the car. My hand pulled up her dress, just a little bit, as she was bending over the console. She kept going down further and further on me, pretty impressive for a small girl like her. I stuck my middle finger inside of her and she moaned, making my dick vibrate, and I loved it. My finger went further in, probing around inside. She was wet and sticky, and I could feel her running down my finger, just like some spit was running down my member. My ring finger entered her next, this time generating a louder moan. More movement, more moaning, this time from both me and her. Her hands started to get in the mix, wrapping around me, assisting her mouth in a job well done. Since the night had been all about experimenting, I decided to stick just the tip of my thumb into her ass. An immense amount of pressure was exerted on my fingers inside of her. Her head went down low, almost to the base of my cock. It had to be somewhere in her throat by now. She let out the loudest, most honest, sexy moan I've ever heard.

"We're going to my place. Now." She said, after a tiny gag on the way out.

She sped away, wiping the fog from the window in front of her - this could in no way be safe. Once she could see, her hand was back over, gripping me hard, pulling on me. I was getting close, and I thought she could tell. I zipped up as we pulled into her driveway. The car was barely off before she was running inside, forgetting her jacket and shoes in the car. She upstairs, and I stumbled around trying to find her, in the dark. She called me over, and I could see her figure in the moonlight. She was skinny, with almost no boobs to speak of, but a gorgeous face and a nose ring. Perfect silky smooth black hair, and a very fit body. We kissed, and I pushed her back onto the bed. She turned around and waved her ass around while I stripped down. I pressed against her, trying to enter. I could feel her dripping onto the head of my penis as we tried again, this time her fingers spreading her pussy lips for me. We had to try a few more times, with a couple minutes of fingering, before I could finally get inside her. When I was about halfway in, her left leg started shaking, and she gripped the sheets tight, moaning loudly (I'd learn the next day that we definitely woke up her roommate... whoops).

Between all the activity of the night, all the rubbing, the blowjob in the car, and how intense it was once we finally were in bed, I needed to cum, and fast. I pulled out of her, and she let out a moan of disappointment, but soon squealed as cum ropes lashed across her back, all the way up to her shoulder blades. I collapsed on the bed as she grabbed a towel and wiped herself off, followed by me. She laid down beside me as we drifted off to sleep.

sorry for cutting it a little short, more detail I wanted to add but reaching the character limit.