For my 30th birthday my friends and I coordinated to go on a trip to New York City for a long weekend. The adventure that we went on over those four days is worthy of a novel unto itself. This story is just the tip of the iceberg and how things got kicked off — and how they almost went too far.
In a nut shell we started in the city where I lived at the time. My friends were due to come into town randomly throughout the evening as they got off work or finished whatever they were doing. I lived really close to more than a dozen bars so we decided that night one of the birthday events would be hitting them all. We were coordinating everything by text message as the crew arrived and I had also invited a bunch of other friends out to celebrate before we left the next day.
At its high-point about fifteen people showed up — some left early, some came late, two people came — left — then came back. Around midnight my favorite bar — also the one half-a-block from my house — shut down early and we all headed back to my place and went out on the deck to continue drinking and telling stories of our bravado. When it came to my turn I started to tell the tales of my former friend with benefits, Penny. Almost everyone there knew her — either through our time as fuck buddies, or from high school, or from just meeting her about town at random. It is strange how small the social circles of some cities are.
One of my friends who had hung out with Penny a few weeks before had no idea that she and I had been lovers and was blown away by my stories. So much so, that he didn’t believe me and drunkenly texted her to see if I was bullshitting or not. Penny confirmed that everything I was saying was true and asked why he was asking. He told her about my birthday and then, a moment later, I got a “Happy Birthday” text from a number I had long since deleted from my phone.
“Who dis?”
“Penny!”
“Thanks!” I replied and put my phone away. 5, 4, 3, 2, 1. “What are you up to tonight?”
“Drinking.” She replied. 5, 4, 3, 2, 1. “Why?”
“You should come over.” Oh shit, I sent that before I realized what I had typed.
“Oh yeah?”
“Yeah, we are all here talking about sex and I have been bragging about how good you are in bed.”
“I am the best.”
“Yes. Yes you are.”
“Do you really want me to come over? What are we going to do?”
“We are going to gangbang you.”
“LOL.”
“Really, come over and we will all fuck the shit out of you.”
“Okay. I’ll be there in fifteen minutes.”
I told the guys that Penny was coming over for a gangbang. Everyone but my old buddy Pete thought I was joking. One of the guys who I had just met a few days before decided that was the time to peace out and left for the night. Everyone else started to build up some level of awkward tension as they contemplated the chance to participate in a gangbang at 1 am on a Thursday night.
Fifteen minutes passed and there was no Penny. I called and she explained that she was riding her bicycle across town and was struggling because she was pretty drunk. We waited fifteen minutes more and we heard a knock at the front door. It was Penny; smiling, laughing nervously, sweating a bit, and had a beach-style bicycle with a banana seat in tow. I was in the kitchen having a scotch and talking shit. I heard the guys welcome her in, make sure she was okay, then escort her over to me — the birthday boy.
The kitchen was now full of five guys with one beautiful lady in the center of the room. The thirst was thick and everyone was waiting on edge to see if this was really going to happen. Penny had worked off her drunkenness, but was still pretty tipsy and talkative and being adorable. I have no idea what she was talking about — I didn’t care — I decided I wanted to start things so I put down my glass, reached out to her hips, pulled her forward into me, and kissed her hard.
I hadn’t seen Penny in six or seven months. The last I had heard she was in a serious relationship with someone, but apparently that had fallen through. Now I was making out with her surrounded by a bunch of guys — some friends and some just drinking buddies. I stripped off her jacket and purse and tossed them on the kitchen table. Then I reached in and pulled at her jeans to start to strip them off as well. I had her in her panties and her T-shirt before she realized that everyone was watching.
“Oh wow, oh, hi everyone.” She giggled away her shame.
The group of guys looked at me like I was casting a spell. They couldn’t believe that I had been serious about the gangbang and had the power to strip a woman in a kitchen within 60 seconds of her walking in the door.
“Come with me.” I grabbed Penny’s hand and lead her to my room. We stood in front of my bed and I stripped the rest of her clothes off and dropped them on the floor. We continued to make out as I discarded my clothes in turn and then lowered her onto the edge of the bed. I started to lick her pussy right away — no build up, no flirtation, no teasing, just tongue on slit and clit. She started to moan right away; she loved my tongue and I am sure she missed it as much as it missed her. I got her pussy sloppy wet, spit on it aggressively just to make sure, then moved to slap my cock onto her pussy lips a few times to get it lubricated before shoving it into her.
Clearly, I was making a series of bad decisions that night. I hadn’t fucked her in ages and knew she was sleeping around like crazy. Likewise, what the fuck was I doing inviting this girl to my house at 2 am to fuck all my friends on my birthday. Oh well, life gives you opportunities and you either take them or you fuck them up. Why not take an opportunity to fuck.
I was balls deep in Penny when I got the sense that I was being watched. I looked behind me and all of my friends had followed us into the room and were watching me as I fucked Penny. Her eyes were closed and she was just moaning louder and louder completely unaware of what was going on. The guys all looked at each other as if making a silent agreement that this was okay and was going to be a ‘NOHOMO’ situation for each other. I didn’t stop fucking her, but I did turn and give them all the nod of approval along with a drunken smile.
They all dropped their pants and reached into their underwear to stroke their cocks. One friend, I’ll call him Dave, whipped his out right away as he was already hard. I started to rub one of my thumbs on Penny’s clit as I slammed my cock in and out of her and she had her first orgasm of the night. It was then that Penny finally saw what she was in for. The guys had all gotten really close by, cocks in hand, and were getting on the bed to join us.
“Whoa, whoa, whoa, what the fuck?” She started to freak out a bit.
“What?” I asked as two additional guys whipped out their cocks for her to suck on.
“What the fuck is going on?”
“A gangbang.”
“No, no, no, no.” She was in a bit of a panic and was scrambling to get away.
“What? I told you it was going to be a gangbang.”
“I thought you were joking.”
I laughed a deep belly laugh. “Nooooo, not a joke. You’re going to get fucked tonight.”
“Nah uh, get the fuck out of here.” She looked actually afraid and I started to realize it. “I only want to fuck you.”
“Well, that is lame, but okay.” I shrugged. “Alright guys, get out of here. No gangbang.”
Pete continued to get closer to Penny and grabbed her head as he pointed his cock at her mouth. Dave took notice and started to do the same thing as Penny covered up and shook her head ‘no.’ The other guys backed off, one — my buddy Kurt — completely left right away.
“Hey, guys, come on. No gangbang.” Pete moved in closer again and shoved his cock into her face and then Dave did too. I got mad. “Hey, seriously. Fuck off. She said no.”
“She’ll be fine.” Dave said.
“No. Fuck off. It’s my birthday and I’m going to get laid. If she won’t fuck me because you guys are here I’m gonna be pissed. Get out of here.”
That seemed to be the only thing that slowed down Pete and Dave’s rapey vibe. Bros before hoes at its absolute worst. Fortunately, they did fuck off and Penny looked at me with wide eyes and a look on her face that seemed to scream ‘what the actual fuck, dude!?’
“I thought you wanted to get gangbanged.” I smiled like an idiot.
“Oh my god. You’re crazy.” She calmed down, smiled back at me then moved in to kiss me again. She wrapped her hand around my still insanely hard cock and started to jerk me off. I pushed her back on the bed almost immediately and started to eat her pussy again. She deserved a good cum after her surprise visit from all my friends. I probably took five minutes to build her up to orgasm and when she finally came it was tremendous. I had slipped two fingers into her and was working her G-spot aggressively. She had gotten incredibly wet and her orgasm was like a mild squirt all over my face and bed and she was not being quiet at all. When I looked up from Penny’s soaking wet pussy I saw that Dave was on the bed again with his cock out pointed at Penny’s face.
“Whoa. Hey.” I called out as Penny’s pussy juice dripped off my chin. “C’mon.”
“What, she wants it.” Dave replied innocently as he stroked his cock.
“No, no, no.” Penny shook her head.
“Dave, dude, you gotta go.” Dave was a big dude, black guy, probably 6’5”, and he had an intimidating presence when he wanted to. I wasn’t backing down though and stared him down until he finally tucked himself away and walked out of the room. I turned back to Penny when he was gone, “Sorry ‘bout that.”
“It’s okay, just fuck me.”
I felt like I fucked her for twenty or thirty minutes — max. The next morning after Penny left the guys told me that I fucked her for hours. They heard her moaning and calling out my name until at least 6 am. Regardless of how we remembered it, the sex was fantastic. It was a little rough, a little nasty, and very messy. I remember there were a few breaks where she took some long drags on her vape — which she had never done before — and we both chugged a lot of water. Probably the only reason we made it as long as we did given the amount of booze we had.
In the morning I woke up cuddling her and was really surprised that the whole thing hadn’t been a crazy dream. I could hear the guys getting ready to hop in the van coming to pick us up and Penny and I had a brief talk as I took a shower and got dressed. I thought that — maybe — things were finally at a good place between us and we could try to just be friends again, but she was still pissed off about something and brought it up again. We had a little fight and I told her I was done — I would never call her again. I needed this anger to be past us and continuing to hook up once in a while was not working.
She left that morning on her bicycle as my friends and I headed off to the airport. That was the last time I ever fucked Penny — I’m glad it was a memorable one — even if it didn’t turn out to be the gangbang she deserved.
Source: reddit.com/r/gonewildstories/comments/nedpj3/for_my_birthday_that_year_i_decided_it_was_time