Chapter 1: The Naked Bike Ride
I'd been dating Moriah for 6 months when this whole thing started. Moriah isn't a voluptuously curvy girl by any means but she's a pretty attractive girlfriend with red hair, a petite body, cute perky tits and a tight little ass. She's fun to be around and I feel like she's in my league and that's all I need to make me happy.
Throughout the first few months of dating, we would talk about our various friends, wanting to meet each other's friends to get a better sense of one another. I had met a decent number of her friends off and on up to this point but one of her friends, Brendan, was someone I had yet to meet. Apparently they met in a college course and were friends in university, then they lost touch but had recently gotten back in touch and would hang out socially. According to Moriah, Brendan was extremely social and usually wanted to meet up spur of the moment through invitations to events and parties with large groups of his other friends. Hence, coordinating a hangout to meet him was difficult to plan.
I live in Seattle, and every year we have a "world naked bike ride". Moriah was someone who was adventurous and mentioned that it would be fun to try as neither of us had done it. I'm not super confident in my body and manhood but I agreed it would be an experience to try so we decided to do it. When the day of the event rolled up, I was working on fixing my long-neglected bike (the seat got stolen) while she was browsing her phone on the couch.
"So it looks like Brendan is also doing the naked bike ride with his friends", she mentioned. She must've gotten a text from him.
"Oh really?" I replied. I really didn't want to meet him at the naked bike ride. I had no idea what he looked like, and I didn't really want to meet one of Moriah's male friends for the first time casually naked (and Moriah being naked). In any case, I played it off.
"Yeah, we don't have to meet up with him though. I know that would be weird" she said. It's like she read my mind.
Eventually the late afternoon came and we rode our bikes down to the starting spot in a local park. There were TONS of naked people all about. Bodies of all shapes and colors, old and young. it was an interesting sight. When we parked our bikes along the edge of the park, Moriah quickly stripped down to nothing and I slowly followed suit. A couple other people started chatting us up who also were doing it for the first time. One of them had extra body paint so we drew on each other's backs. After chatting for awhile, Moriah suggested we do a walk around the park perimeter to get comfortable and see all the crazy sights and setups.
As we were about 3/4 of the way around the loop, Moriah quickly jolted back, spinning around to look directly at me, a smirk on her face.
"So... I see Brendan and his friends. Do you want to go say hi?" she said.
I really didn't want to, but I could tell she wanted to, so I felt like I had no choice but to play along. "Sure, let's do it" I said.
As she led the way through the swathes of naked people, we finally arrived as I heard someone yell "Moriah!" nearby. There he was, standing with his friends. The first thing I noticed was, Brendan was black. There aren't loads of black people in downtown Seattle so for better or worse that's what I noticed first. Second, he was taller than me and he obviously worked out. Third, and I couldn't help but notice, his dick was flaccid and was about the size of my dick fully erect (note - I was NOT erect at the park lol). This sent my mind tumbling into a spiral of inadequacy and anxiety from the get go. Brendan was with no other dudes, but rather 4 equally attractive women, all naked. While this was a sight to behold, my mind was focused on Moriah and Brendan seeing each other naked and that I'm sure Moriah was obviously curious what Brendan looked like under the covers, getting her first look at her guy friend naked.
What made matters worse was that Brendan was charming and friendly. We exchanged a handshake and all of us small-talked for a bit about how crazy this ride seemed.
"You guys want to join our group on the ride?" Brendan finally asked.
Moriah looked over at me, "what do you think?"
I nodded in approval. What was I to do? I wasn't gonna be the party pooper. Later during the ride she knew something was off and pulled me aside to ask if I was ok to which I ensured her that I was. The bike ride was actually fun but throughout the ride, Moriah would ride next to Brendan a lot and sometimes right in front of him. Riding behind her I noticed her taking more than a few glances at him, peeking down at his manhood, not realizing I was observing her from behind.
The ride was actually a lot of fun. The ride finished at another park where a dance party was going to start until the wee hours of the morning. Brendan asked if we were going but Moriah and I decided to call it. Neither of us were late night people. We exchanged pleasantries and both went our separate ways.
Later on after we got home from the ride, we unpacked the event a bit. "Did you have fun tonight?" she asked.
"Of course!" I said. "Granted I wouldn't say it was exactly comfortable being naked around your friend meeting him for the first time."
"What about it bothered you? Brendan wasn't weird about it." Moriah was trying to get to the root of the problem. I wasn't going to let on so easily.
"I mean...you guys haven't seen each other naked, right? So I'm sure that was a sight for you..." I said, slightly passive aggressively.
She smirked. "Yes, I saw Brendan naked. He's fit and he has a big dick. Whoop-de-doo. He saw me naked. I'm sure he noticed things. Whoop-de-doo. The point was just to be naked and have fun!"
I was taken aback at how she just went on and bloated out her observations so nonchalantly.
"Yeah, well comparing dick sizes as a first meet and greet is just a weird way to meet someone is all I'm saying."
Now she started talking playfully trying to take the edge off the conversation, pushing me towards the couch. "D'awww is my boyfwen upset his pee-pee isn't the biggest pee-pee in the world?" She pushed me down on the couch and straddled me. "Does he feel like he has a tiny weiner??" She flicked my balls and started to kiss my neck, moving to my chin and then up to my lips, making out with me.
I chucked. "Oh stop it", I retorted between kisses.
She started pulling off her clothes and pulling down my pants. I was completely hard as she grinned against my dick until she slipped it in and started riding me. Slowly the dirty talk came back, this time more sexual.
"Is your tiny dick hard babe?" she asked as she rode me on the couch, hands on my chest. I didn't reply, pulling her hips against me with each thrust. "Your dick is much smaller than Brendan's dick isn't it babe?" She whispered in my ear, riding me harder and faster. I let out a small moan. "Brendan could probably fuck me much deeper than you could couldn't you babe?" She started moaning, bouncing rapidly on top of me. "You're no match against his huge cock are you!" she moaned.
I was so turned on at this point, I could barely hold it. "I want your tiny little cock to cum in me" she exclaimed with her head tilted back. "Do it!" She yelled. I held her down and spurted my cum into her as we both moaned in pleasure, eventually collapsing next to each other on the couch.
After a bit of cuddling and the euphoria wore off, Moriah said, "damn babe, I didn't know you got off to that stuff" she giggled as she hopped up playfully to go clean up in the bathroom. She turned back, "and for the record, your cock is just fine", she said with a smile as she walked away.
Chapter 2: The Halloween Party
As the months went on, we still hadn't hung out with Brendan in a normal setting since the naked bike ride. A couple times Moriah would mention she was going over to his place to hang out with him and his kid (he had a kid with an ex) to play board games. He was pretty private with his kid she said. Since they had a previous relationship, I didn't think anything of it. Granted, I did confront her in these initial months about him during a car ride we had, talking about our friends.
"Soooo, I just wanted to make sure, you and Brendan never dated did you?" I asked, when he was naturally brought up in conversation.
"Brendan? Oh God no. He's definitely not my type" she replied.
"Why is that?"
"He's not monogamous. He's a self-described consensual non-monogamist. I can't ever keep track of who he's dating". This didn't really surprise me since most of what I heard about him and witnessed with him was that he had a vibrant social life and never seemed to want to do any low-key hangouts.
Halloween was coming up and we were deciding what we wanted to do. Moriah mentioned that there was a costume dance party hosted at one of the convention centers in town. Brendan and his squad was going and Moriah, being the socialite herself (and with pent up social energy during covid) wanted to go.
"Do you want to go to this halloween dance party with me?" she asked. If you haven't guessed by now, Moriah was more often the one to set our social calendar. "Brendan has a new girlfriend he's going to bring". Aside from the prospect of it being fun, I also wanted to ensure Moriah that I was always down for a good time. I wasn't going to let her go have fun with Brendan at a party without me showcasing that I could party too. I happily accepted going to the party. Now I just needed a costume.