BoxerBriefs - Part 1

BoxerBriefs

Submitted by Chris

Part 1 of 2

I have always been obsessed with underwear, ever since I was 13 and had to wear my older brothers hand-me-downs. I would lay in bed wearing his boxerbriefs and run my hands over them massaging my cock in the process. Everyday I would take a pair and cover my face and stroke as fast as I could until I exploded all over my chest, my eyes watering and me breathing heavy. My obsession went on for years but really escalated when I was able to buy my own as i got older. I went from just the plain tighty whities to all sorts of colors and all brands, the more outlandish the better. By the time I was able to move out of my parents’ house I had close to 100 pairs and I jerked off with each one

I moved into my own place with a really good friend of mine. We had been friends since we were 6 and were very close. It was the first apartment for both of us so there were a few adjustments. it turns out my buddy loved to be almost naked when he was home, not that I would complain because I had a major crush on him for years. He said he was straight but every once in awhile when we were younger and drunk he would let me jerk him off. I tried to go farther but he never would let me. So he spent most of his time in just his boxerbriefs when it was just the 2 of us at home and he wasn’t shy when he would wake up sporting the biggest hard-on I’ve ever seen. 

About 6 months of living together my buddy managed to find himself a girlfriend so I didn’t see him that much. It gave me time to go through his underwear and abuse a few. One day he came home almost in tears. I asked what was wrong and he tells me that after 2 month his he caught his girlfriend cheating on him. He was devastated and all he wanted to do was get blind drunk. Since I didn’t want either of us to drive we stayed in and started drink beer after beer. After almost a case of beer he was hammered and could barely stand let alone walk. He heads into the bathroom to pee and a minute later i hear this huge crash. I rush into the bathroom to find him sprawled on the floor with his pants around his ankles and his huge cock hanging out. It was all I could to just bend down and take that beast in my mouth. I half carried him to his bedroom as he was telling me what a great friend I was. I dropped him on his bed and started taking his shoes and socks off when I noticed that there was a growing bulge in his pants. I was torn as what to do but I didn’t wanna screw up our friendship but it was so tempting. I couldn’t help myself, I leaned down to get a better look. His cock was amazing. I checked to see if he was passed out , he was, so I slowly pulled his boxerbriefs down and tucked them under his huge balls. Once down his cock sprang up and stood straight out, it looked to be about 8" big and very thick. I got close to hit, scared to touch it, but marveling at how perfect it was.

Suddenly I felt a hand on the back of my head pushing me towards the cock. I looked up and my roommate was awake. His hand rested on my head and kept pushing me towards his cock so I opened my mouth and slowly took it in. It filled my mouth. It was soft to the touch and I could feel the veins as it slide deeper into my mouth. Now my buddy had both hands on my head and started to fuck my face. I was gagging on the length of it but that didn’t stop him from ramming it deeper and deeper into my mouth. He was moving faster and faster. My eyes were watering and spit was flying everywhere. He battered my face with his monster cock for a few minutes until he grabbed my head and pulled me all the way down his shaft and held me there; a second later he erupted filling my mouth with rope after rope of sweet tasting cum. I couldn’t handle it all and some dripped down my chin but I did manage to swallow most of his load. When I was done I looked at him and he was fast asleep so I pulled his boxerbriefs up over his deflating cock and went to bed.

I was awaken the next morning to my buddy sitting on the edge of my bed. He asked me if what he thought happened really did happen. I couldn’t lie to him and told him yeah. He started to apologize but I stopped him and told him everything was cool. He asked me if I was gay since I sucked his cock and I told him yes I was. I didn’t want to tell him because I was afraid of losing him as a friend. He told me that would never happen. He kind of knew from the way I would stare at him and he admitted that he liked the attention and would show off for me to see what would happen. I asked him what happens now and that’s when he totally surprised me. He leaned down and kissed me gently on the lips. When our lips parted he asked if he could climb in bed with me. I slide over and he got next to me. He said that about a month into us living together that he started getting feelings for me but was scared since he always thought he was straight. I told him don’t worry about it and we embraced. We kissed deeply. Softly at first and then harder. My hands roamed over his body and made their way to his crotch and those amazing red boxer briefs.