This is part of a series detailing my experiences with my jerk buds! I would suggest reading the other parts for context, but it’s not a necessity
“Want to sesh tomorrow night?”
This text from my jerk off bud was stuck in my head all day and all night. I started getting ready half past 7 shaving, showering getting my clothes together. I had to stop myself from thinking about it in the shower or I wouldn’t be able to save myself for our first one on one sesh. He texted me to make sure we were still on for 9 and asked if I wanted any beers. “Hard liquor for me tonight” I texted back, followed by a picture of a half empty bottle of Deep eddy’s vodka. “Bet, see you soon”. He responded.
The drive there would’ve been anxiety inducing, if I hadn’t put on some music to listen to. The voice Kali Uchis rang through my head as I thought about the clothes I was wearing. I had on an oversized Band shirt from hot topic and the shortest pair of shorts I could find in my closet, but it was what I had on underneath that really pulled my attention. Silk panties that I got from our first session, the same pair that my bud frotted me in…
My focus shifted back to the road as I pulled into his apartment complex. It was going to be just me and him. He had roommates, but they were out of town for the weekend on a student organization retreat. His girlfriend wasn’t going to be there either. As he explained, she was out having a girls night, and we would have the house to ourselves. I hadn’t realized I had left my car until I was up the stairs and at his front door. In one hand I had the bottle of alcohol, in the other I held my overnight bag. It wasn’t uncommon for us to crash at the hosts place, so I always brought it. This time, along with all the sexy clothes they bought me, I had a dildo, wrapped up and neatly tucked away in my bag. I got the dildo over the summer and had been practicing on myself in hopes that one of our jerk sessions might turn into something more. I don’t know why I brought it, it’s not like I was planning on getting it out during our session or anything. I probably brought it with the hope that he may somehow find it and ask me about it.
With slight hesitation I knocked. A few seconds later, the door opens. Standing in the frame was my friend, who looked down at me and smiled.
I wasn’t the smallest dude in the world (about 5’9 and some change) but he was 6’2 and filled out his body frame which made me feel small.
“Hey” I said with a cute smile.
“Hey come in!” He stepped to the side and held the door behind me as I walked in. I felt his eyes on me as I walked into his living room.
I was nervous for the first a minute, but we pretty quickly fell into our old rhythm and things felt normal again. We drank and chatted about all the normal things: friend drama, school, work etc. After about 4 drinks we went outside and smoked a joint on his balcony. Music softly playing in the background we kept talking while we got high. At some point the conversation got to the topic of his girlfriend. I had been avoiding any mentions of her bc I didn’t want to make things awkward, even though he told the group not to worry about it.
We met her at the start of the semester and she seemed like a cool chick. Maybe out of his league but not by a big amount. He brought up how she was somewhat religious, and a bit of a prune. Well prune isn’t the right word. As he explained “she’s definitely a freak, but she just doesn’t want to do it as often as me”.
“How freaky?” I asked
He began to tell a bdsm fueled sex story about one of their nights. As he told the story I asked him questions about it, egging him on. Asking for him to go into further, dirtier details about the event. We both knew what we were doing. Talking about each others sexcapades always turned us on. Eventually both of our hands slipped down to our crotches… I snuck looks as he stroked his 7.75 inch member through his pants (yes we all measured with each other a while ago). As we stroked and talked about his hot girlfriend in bed, the joint turned into a roach. Seeing an opportunity, I stood up and walked slowly. Swinging my hips into my steps, taking my time crossing the small balcony to his trash can by the door. I listened to him slow down his speech as he watched me from behind. Stopping at the trash can, I put my foot on the thingy, opened the lid and dropped the roach over the opening. As the lid slowly shut, I put my hands on my hips and just as slowly shimmied my ass out of the tight shorts, showing off my ass to him. I left my shirt hiked up so he could see me as I walked back to my chair…