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  • — Embarrassing Moments —
    Posted by Anonymous

    I was a junior in college and was assigned to a roommate who was a sophomore. He was a good looking kid, wore A&E and Hollister, etc. He got drunk several times and made huge messes in our room. He'd pass out on the puke-covered floor and pee his pants while passed out. He was cute and so I forgave him. He always wore boxers from A&E and freely walked around in them often. One day he asked me to borrow a pair of boxers, all his were dirty. I had seen he had a package of Fruit of the Loom white briefs in his drawer before, and I suggested he wear those. He replied that his mom had bought them and he hadn't wore those since 10th grade. I tried to stall because I wanted to see him in those briefs, but he went over and grabbed a pair of my jockey briefs.

    A couple months into school, his parents came to visit. He begged me to not tell them about his drinking. I agreed. His parents took him to a nearby water park and he had an accident. He fell down and broke one arm and the other wrist. He couldn't do anything for himself. He lived several states away, so his parents stayed several nights to help him recover. I gave him the lower bunk and helped him though the night when his parents were at the hotel. Each morning, his mom would help him stand up, and then change his shirt. Then she'd remove his pants and boxers with me in the room and redress him. He sat around and did little for several days, then his parents asked if I could care for him. I agreed again.

    The morning his parents were to leave, his mother changed him again. I was sitting in the corner having a conversation with him and his mother takes off his pants and boxers. He looked extremely embarrassed standing there with his penis hanging out with only a wifebeater on. We had individual showers, so I had never seen him naked from the front before. He stood there a while as his mom looked for underwear. He was out of boxers and she opened those briefs I mentioned earlier. He yelled at her ‘no!', but she continued. She pulled the briefs up and he turned red and kept persisting to take them off. He looked so good standing there in just his briefs and wifebeater. He was so embarrassed, however, and I got such a rush from this embarrassment. His mother finished dressing him and they soon took off.

    I couldn't stop thinking about seeing him embarrassed naked and in those briefs in front of me. I got such a rush from that. A friend of his came by and they went to class and I masterbated. Best I'd had in months.

    Later that night, he had to use the restroom. I took him into the stall and removed his pants and briefs. He sat there on the toilet extremely embarrassed, but he did talk to me. I had to wipe his beautiful behind, then pull up his briefs and pants. When it was time for bed, I removed both his shirts and pants. He told me to put some boxers on him. I said that his mom didn't want him to wear them because they were dirty. I told him ‘Go to bed," and he got an attitude. I pretended really upset at the way he was treating me, and said "if you are going to be a jerk, I'm telling your parents about the drinking." He laid down on the bed in his briefs...and only his briefs.

    The next morning, I woke up before him, but he still had covers over the briefs that I had put on the night before. I pulled them off as to wake him up. "I have to get to class, lets get going," I said. He stood up and I opened the door. He got an attitude again, yelling that he needed clothes before going to the bathroom. Ususally he walked down the hall in his boxers to the bathroom in the morning. I snapped back that I didn't have time and to remember that he had to cooperate through this or I was telling. You could tell he was pissed and walked quickly down the hall aside me in only his briefs. Several people passed and he was shaking. He thought briefs were the most embarrassing thing a guy could wear, and there he was in them only.

    We walked into the bathroom, and there were 4 guys at the sinks and 2 at the urinals. I thought he would walk into a stall, but he walked up to a urinal. Instead of just pulling them down far enough so he could get his penis out, I lowered the pair to several inches before his butt. There he is standing in a bathroom with 6 or so guys, with briefs on and his naked ass exposed. I was getting very excited. He peed all over the wall because he couldn't hold his junk. The whole room was laughing. I pulled up his briefs, washed my hands and helped him back to the room. He was royally pissed and embarrassed.

    Back in the room, I took off his briefs and he stood there naked. He still wasn't used to be naked in front of me and made an excuse that it was cold (and something was small because of it). I pulled out another pair of briefs and he started his screaming. I got angry again and he finally let me put them on him. He was dressed and I changed just down to my boxers.

    He hadn't had a shower in several days, so the next morning, I suggested it. His dad had apparently washed him the last time. He said it was a must, and after letting him crap again, I got his towel and soap. He had walked down the hall in briefs again and was standing alone in the bathroom waiting for me to get back. The bathroom is a square with a wide open area in the middle, sinks on one side, toilets on one, urinals on one, and showers on the other. The showers are individual and usually you'd get in, close the door and remove your underwear. I couldn't get in with him, so, with the door open, I pulled off his briefs and washed him. I didn't get near his private parts, as I'm not that brave. After a few minuets he wanted to "get the hell out" and so I stopped the shower. Another guy was waiting for the shower, so I took advantage of that. "Come out and let him use it," I said as I pulled on sholder. He was now butt naked in a bathroom with 8 other guys. I kind of moved him a little closer to the middle and started drying him off, starting with his head. The guys started laughing at this. Picture it, him standing there wet, helpless, and butt naked as I dry off his hair. The guys were actually watching and cracking jokes, and pretty soon a couple more came in or out of the shower. I had totally exposed him naked to about half the guys on our floor.

    Then, the best thing happened, he popped a boner. The minuet this happened, all eyes were on it. He started to run, and I held him back, pulling on his injured arm by mistake. With the pain, he stopped long enough that I could get his briefs started up. All the guys would now see him be dressed in briefs, what he was so embarrassed to wear.

    He was so pissed and depressed when we returned to the room, I felt bad that I had exposed him like that. Everyone on the floor would know that he had got a boner and wore briefs. I dressed him in a pair of my boxer briefs, and did his laundry that day. The rest of the time, I put him in boxers and tried not to let others see him naked. I had my fun and everyone made fun of him for that.

    The best part of the tale: it made him less embarrassed of nakedness or briefs. Once he was back in shape, he would get naked while changing in our room, and wore briefs from time to time.

    #1653 — Comments (1) — Feb 16, 2008 at 8:51 PM — That's Juicy! (2) Remove This.
  • 1
    after that did you both do anything more

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