"I'll Never Wear Boxers Again"
Wibby posted a rather funny story that prompted me to remember a similar incident involving one of my good friends. So I thought I?d share it with my loyal readers. (maybe I should?ve said loyal reader, I don?t want to become to ambitious)
Anyway, during my late teens and early twenties, one of my best friends was also named Jason. We worked together and were known as the ?two Jason?s? or simply as ?Jason Squared?. After we both turned twenty-one, each Monday night we?d go out for our weekly pub crawl. This night was reserve for just the two of us, no friends, no girlfriends, and no problems.
It was during these weekly binges that I first told him I was gay. True to his devil may care attitude and laid back demeanor, he took this declaration in stride. Though looking back, I kind of wished he would have been more upset. This would?ve saved me tons of heartache. But I digress?yet again.
Jason and I were always comfortable around one another. It was common for us to sleep in the same bed, granted, we were passed out. But waking up snuggled together was something that happened often. Before I told him I was gay, we?d go double dating and the girls would often complain that we?d spend more time talking to each other than paying attention to them. Looking back, it was quite obvious that sooner or later we?d start fooling around.
The first time something happened between was after one of these pub crawls. We had stopped at a gas station to get cigarettes and sodas on the way home from the bar. Jason had to go to the bathroom, so I paid for the grocery?s and waited for him in the truck. After he climbed inside the truck, I noticed he had this weird look on his face and for the rest of the way home; he acted strangely, nervous and giggly at the same time. I chalked it up to a long night of beer.
Once back inside my apartment, he was flirtatious, in a way he had never been before. I was drunk and getting hornier the more he carried on. After about twenty minutes of this weird flirting, I informed him I was going to bed. It wasn?t that I was really that tired, but I really wanted to toss one off. He looked down at the floor and in this quiet voice, he asked if he could stay with me. He didn?t ask if he could crash, he didn?t ask if he could sleep over, he asked if he could stay with me. For a moment, because I really wanted to jack off, I almost said no. But I never could tell him no, even now, I can?t say no.
Anyway, and no that was not a digress. So there.
I took off my clothes, and slipped into a pair of shorts. He asked if he could borrow a pair of boxers to sleep in, something I thought was a really strange request. Jason did not then, nor does he now wear boxers, EVER. I gave him a pair and he went into the bathroom to change. Another thing that was strange.
I climbed into bed and turned off the lights, and waited. After a few minutes, I heard the bathroom door open and heard footsteps down the hall. The door to my room opened and in walked this?glowing cock. While he was in the bathroom at the gas station, he had bought a glow in the dark condom from the machine on the wall.
I was more than taken aback, yet intrigued at the same time. I said something along the line of ?nice cock?. To this, Jason laughed and flipped on the lights. It was not his cock that was in the condom, but three of his fingers. We laughed and once again he turned off the lights. I could see him slowly coming towards me, his pretend cock wagging before him leading the way to the bed. I admit I watched him walk towards me wishing that really was his cock.
Once he reached the bed, he started giggling again, and I watched the hand that had the condom on it move to his side. I saw the condom disappear and realized his fingers were inside the boxers. I realized he was pulling down his boxers when another glow in the dark condom suddenly appeared. Being that he was two feet away from me, this time I could tell that this one really was his cock.
He took another step, his crotch now inches from my face; I could smell him he was so close. The hand that hand the condom on it, moved from his side to grip his very hard cock. I heard him whisper, ?Do you like what you see?? I didn?t answer, I couldn?t. I didn?t want to risk destroying this moment. I reached out with my hand and touched his cock. He sighed loudly, my wish had come true. Needless to say, neither of us got much sleep that night.
A few years later, in the after glow, he would admit that for months he was racking his brain, trying to conceive a plan of attack to seduce me. But he wanted to make sure I was interested in something sexual before trying anything. After his admission, it was clear how thought out and methodical he had been. From the constant touching, the sleeping together, suggesting naked hot tubing, everything had been done with the purpose to get me into bed. I asked, why didn?t you just ask me? He replied that I had said shortly after I met him, that I would never have sex with a friend.
This caused me to laugh, because though he was in the room, it was the girl sitting next to him that I really wanted to hear me say that I would never have sex with my friends. She had been throwing herself at me and I had no desire to catch her. Lots of wasted time, I could?ve saved so much time if I would have just said, guys, I?m gay. Anyway, still not digressing.
So Jason and I were friends with benefits. To be honest, I was completely head over heels in love with him. And no matter what he says, I know for a time, he loved me as well. Shortly after this incident, he moved in with me and for the next two years, we were almost inseparable. But being gay was/is something he denies being. He?s told me, and I believe him, that I was the only guy he was ever attracted too. I was the best man in his wedding, and the night before he promised to forsake all others, he asked me to fuck him one last time. Okay, this might be digressing. Jesus, be patient already.
To get around to the point of this post, one night, during those two years that we lived together, we had gotten home after Monday?s pub crawl. Both of us were quite trashed. At the time, he was dating this chick that was away at college and I was trying really hard to catch this nerdy little boy I had been chatting up online. So once back from the bar, I immediately jumped on the computer to see if my boy was up for some dirty talk. He was, and for about an hour, I was content to do some chit and some chat.
DIGRESSION ALERT! Ever since that first night, whenever I saw Jason in boxers, usually a pair of mine, I knew that he was looking to fool around. If he was wearing briefs, then I was going to be tossing one off alone.
Like I said, I was chatting for about an hour, when I heard Jason open the door to his room. From where my desk was against the wall, I could turn my head and see Jason?s bed if the door was open. He walked out, wearing a pair of boxers, and headed into the kitchen where he got a drink. Walking back towards his room, he looked at me and smiled. I noticed right away he was rock hard.
Yet on the computer, my nerdy boy was almost ready to finally meet me in person. We were so close, I could feel it. I looked at the screen, I looked back to Jason, he was now lying on his bed, naked, slowly stroking his cock. I didn?t know what to do, I was horny, ten feet away was a willing boy, yet I kind of liked this nerdy boy as well. But Jason, jacking off while saying my name only a few feet away, and honestly the love of my life, won.
I walked into his room, he looked at me and smiled, his hand stopped. He pointed his cock in my direction, silently telling me to have my way with him. So I did.
It was just starting to get fun when suddenly he begun puking his guts out. I was sober enough to get out of the way, but he puked all over his bed, all over himself. It was quite the mood wrecker. Once he finished, he headed into the bathroom and jumped into the shower. Being the neat freak that I am, I cleaned up the mess and threw the sheets in the washer.
Figuring the night was over, I went back to the computer to see if nerdy boy was still online. He was, again we started chatting. A few minutes later, Jason comes out of the bathroom, freshly showered and still wet with a raging hard cock. He smiles at me, and heads into my room. Needless to say, I never did meet nerdy boy.
Jason and I had this weird relationship for years. When we were alone, late at night, we would fuck for hours. But it was something we?d never talk about during the day. We had dozens of unspoken rules that we both followed, silently and in secret for years. Never speaking about or acknowledging our lust filled nights.
Until the day I met his fianc? for the first time. We were talking over dinner, and Jason and I were reliving some of our wilder times. And he gets this smile on his face, and suddenly brings up the time he almost pukes on me. Of course she wants to know why we were in bed together in the first place. I was at a loss for words, but Jason smoothly told her a rated G version of the story.
Later, when she had gone to the bathroom, he started laughing, saying something about the look on my face. I didn?t think it was funny, remember, I was still in love with him and more than a bit jealous. He leaned in close and whispered, ?You give the best head I?ve ever received. And I know I can?t love you the way you want me too, but sex with you is something I?ll never forget, no matter who I marry.?
It was the first time he ever admitted to fucking me while sober. But it was the right thing to say, because that statement convinced me to agree to be his best man. Sadly, I?ve not seen him since the wedding. I hear he has a baby girl now, and I wish him the happiest of lives. And though our friendship has fallen away, I?ll always have the memories of that apartment and the time we spent together.
PS: During that night I met his fianc?, she brought up the fact that he refuses to wear boxers. Jason and I exchanged looks, and started laughing. He kissed her, then said, ?I love you, but I?ll never wear boxers. I used too for a time but I stopped.? The night before his wedding, he was wearing boxers.