This is a long one. I apologive for the length.
My co-worker "George" and I like to knock off a few drinks after work, at least three times a week, sometimes five. George is a 35-year old divorced hunk who looks (and sounds) like George Clooney; I am two years older and resemble Jason Segel. George is a ladies' man, although not in an off-putting way. I am a fairly reserved gay man until you get a few Jagers into me, and even then, I'm pretty careful. George has been divorced for two years; I ended a four-year relationship a few months ago. George and I have never socialized on weekends. He is aware I'm attracted to him, but we have always kept things platonic. Until now. I think. This is why I'm writing to you.
Recently, George and I were drinking at one of our favorite watering holes and really tying one on. Like I said, I have always had an attraction for George, but it's always been a joking matter, as he's straight. We were drinking with one of our favorite bartenders "Michelle" that night and we ended up spending way too much money on computerized word games. One game, "Wordster", is a particular favorite of ours. George is always frustrated that he cannot beat my high score on this game. I routinely finish in the 130,000 range; George is lucky to break 100,000.
That night, quite toasted, I decided to spice up Wordster a bit. I suggested to George that we raise the stakes on the next game so that the guy with the lower score would have to do something absolutely humiliating in front of the other guy on a later date, something involving total nudity on the loser's part. I was way ahead of George in the game that night and had something particularly delicious in mind for him. George didn't blanch at the word "nudity"—in fact, he broke into a huge grin—so I drunkenly went on with what I thought would be leading a lamb to the slaughter.
Specifically, I said to George that the "loser" of the next game should be required to masturbate naked in front of the "winner," who would watch these proceedings fully clothed and be allowed to tell the naked guy exactly what to do to himself. The "loser" would have to jerk off for thirty minutes—at the "winner"'s apartment, after work.
If I hadn't had so much booze I would have never suggested this to George, but once the words were out of my mouth, it was too late. To my surprise, he enthusiastically endorsed this "wager." I was getting excited just thinking about how much fun it would be to humiliate him at my apartment. I had never seen him naked (and vice versa), but he fills out a suit quite nicely. I'm nice-looking and fit, but George is a hands-down head-turner. You've have to be a corpse not to acknowledge it. Thankfully, George is genuinely self-deprecating. Although he is always impeccably well-dressed, there doesn't appear to be a vain bone in his body. I've never been completely sure if he realizes how just how attractive he is.
Back to the Wordster bet. George even added to this wager by suggesting that the "loser" would have to do this self-abuse not once, but twice, and the second time, the "winner" could invite a "friend." I said yes to this without thinking, as I have several gay male friends who I know would kill to see George naked, let alone masturbate to a climax. Most of them have never actually met George, but I've described him more than once, in detail.
To my horror, George trashed me in the next Wordster game, getting amazingly good letters and forming all sorts of long words, which beefs up your score. George won the game (albeit by a fucking razor's edge)! He was hooting and hollering and suddenly coming up with all sorts of ground rules for the "performance" I was now going to have to deliver. He insisted that I'd have to do exactly what he said as I masturbated, there would be no "dim lighting" to soothe my embarrassment, etc. etc. He was quite loud about this, although no one in the bar was really paying attention to us, as it was a crowded Friday night and the music was turned up higher than usual. I was bamboozled by this turn of events and especially by George's fervor about the situation. I knew he had been in a fraternity and had enjoyed hazing rituals as the topic had come up at the bar—this was probably one reason I made this stupid bet—but he was really goofing on me at this point, playing with my tie and tickling me. "You're really gonna get it, dude!" he guffawed.
George scheduled the resolution of this wager for a Friday, a week away. So, after a "did-that-happen?" weekend, I worked in the office all week with this on my mind (and it was all I could think about when I got home). Because, beginning shortly after my arrival at the office on Monday, George began quietly, casually alluding to it in oblique ways, along the lines of "Boy, I'm really looking forward to SEEING YOU after work on Friday," "Are you thinking about Friday? I am," and "I just bought a new bottle of lube, just for you, dude"—things like that. I was both mortified and turned on at the same time. Never did I think I would be in this position. George had never beaten me at fucking Wordster. I really had thought the bet was a drunken slam-dunk.
I avoided the bar on Monday and Tuesday. But habit took over on Wednesday, and at the bar, George casually whispered to me, "Dude, don't masturbate until we get to my place on Friday. I want to see a big load." Then he requested another round as if he had just dictated a lunch order.
Out of some sense of warped loyalty, I refrained from masturbating as George requested, and simply tried to put all of this out of my mind for the next two days. It was a long two days on both scores.
Well, Friday rolled around, the workday unfortunately flew by (to me) and we went over to his place. He splurged for a cab, something he'd never done before under any circumstances. I'd never been to his apartment. It was immaculate, if a little surprisingly stark. Once at his apartment, George immediately assumed a personae of control. He informed me I was to masturbate in his living room. He told me to strip down and go take a shower while he made drinks ("I want everything squeaky clean"). He watched me undress in the living room, grinning from ear to ear. "You thought this would be me stripping down, didn't you?" George teased as he watched me. "Loser."
The apartment was on the sunny side of the street so he shouldn't have had to turn on many lights, but he did so anyway. I was ultra-embarrassed and undressed quickly, rushing into the bathroom while still clad in my briefs, which amused George who sang that I was "too shy" (Kajagoogoo). I took a prolonged and thorough shower, trying to decide how I would pull this off without completely degrading myself. I developed a semi-erection within seconds.
"Come out of the bathroom naked," he called from the kitchen (mock-sternly) as I dried off. I couldn't believe what I was hearing from him. I did as he requested. He whistled when I emerged from the bathroom, staring at my increasingly stiff penis and also my pecs. He handed me my favorite concoction—Malibu Rum and pineapple—not bothering to conceal his assessment of my naked body. "You have really big breasts," he smirked. (This is true, by nature more than anything else). My heart kind of sank and I felt myself go completely crimson. George was going to go all out with this.
George remained clad in his business suit, although he had loosened his tie. He told me to go over to the couch, where he had laid out a towel and a bottle of lube. I couldn't believe how prepared he was for this.
He had also sadistically positioned a full-length mirror close to the couch, where he wanted me to perform, "so you can see what I'm seeing, and know what I've seen." The mirror was at an angle where I could see myself completely and at the same time give George an unencumbered view.
Completely frazzled, I drank the drink, naked, increasingly hard, while he watched, then I decided to take the plunge and get this over with. George pointed to a clock and reminded me that I was required to perform for one half-hour. He requested I lie down on the couch facing him. I did. He sat in an easy chair.t leaning back. "Begin," he ordered. I began to stroke myself. George then slowly moved forward for a better look. Even though I was pretty much fully erect, my stomach was doing flip-flops, and I could see my face was flush. I was naked in front of my co-worker George, masturbating. I couldn't believe I was doing it.
Simply put, Dan, this experience was mind-blowing. George would be silently watching me then he would very clinically order me to do things like "play with your nipples, get them hard," "knead those tits," "pull on your scrotum," "rub your piss slit(!)," and shockingly, "spread your legs and finger yourself." This last one was requested in two positions, the first one facing him and then turning around and giving him a view of my entire backside "bent over like a bitch." Talk about out of the blue; I'd never heard him talk like this. Of course this was driving me crazy and I remained hard, not to mention increasingly wet. I kept glancing at the clock and it seemed like the digital numbers never moved. When George told me to turn back around and resume the original position on the couch, I asked him to take off his jacket, tie and shirt, as I was feeling mightly exposed and scrutizined. He refused, reminding me that this was supposed to be uncomfortable for me, "although your body doesn't look that uncomfortable. You look like you're ready to pop, dude." Then George told me to throw my left leg over the top of the couch and to put my right leg on the floor. You can imagine the sight. I was mortified.
During all this, when George wasn't giving me directions, there was dead silence in the apartment, except for the sound of the lube and the pre-cum which George classified as "glistening and cute(?)". I would glance at George, then close my eyes, then open them and look around, trying to stay focused. I avoided looking at the mirror, although this was pretty much not an option, given the way George had positioned it. Several times, George told me to look at him. When I did that, he would make intense eye contact, often expressionless, then move his eyes up and down my body, breaking into a sly smile and opening his eyes wide. I won't deny that this was hot, and I was having trouble not shooting a load until the thirty-minute time limit was up. In fact, I had to stop stroking several times, which prompted a chuckle or two from my "audience." At one point, to ease my tension, I called George a bastard, and he laughed uproariously. Then he told me, quietly, to watch myself in the mirror. I continued to masturbate.
Around the twenty-minute mark, George got up from his easy chair and walked over to the couch. I was spread open in the position he had requested about ten minutes previous. It was a medium-sized couch, and there was room for him to sit at the other end, which he did, smiling broadly. He was now unnervingly close to me; I could detect his cologne. "Watch yourself in the mirror," he said, "and I will tell you what I am looking at." He began a mantra of these words, over and over, with methodical ease: "male breasts," "erect nipples," "erect penis," "testicles," and "exposed asshole." Curiouser and curioser, but it was also completely turning me on. And he very clearly knew it.
That pretty much was the beginning of the end. Embarrassingly, I actually began to moan a little. George loved that. As he repeated his mantra, George would occasionally chuckle whenever a moan would emerge.
I came, volcanically. I shot quite a load and it went all over me. It was five minutes shy of the thirty-minute mark. George laughed out loud again, quite boisterously. "Loser!" he taunted, eyes again wide as saucers. I instantly moved to dry off and cover up but George told me to remain sprawled out on the couch, hands behind my head, until the thirty minutes were over and "your spunk has dried." Those five minutes seemed like an eternity as George recited his favorite moments of my "show". He particularly enjoyed regaling me with how he was amused by my fondling of my "male breasts" (now his new favorite phrase). As I said, I do have fairly substantial pecs and they are a little fleshy, and hearing George tease me made me blush like crazy, a fact not unnoted by George. The statement "I'm really keeping ABREAST of you, dude" has been George's new torture device to me at work (while playfully nudging my pecs when no one is around).
So I went through with Part One of the wager and was hoping George would just drop the whole thing. No such luck. He has informed me that he wants me to go through with the second show and this time he will be bringing along—of all people—Michelle from the bar!
Dan, I am not sure I am up for this. I have never masturbated in front of a woman, much less performed like a naked go-go boy on 42nd Street. And, when we made the bet and finalized the details, I just assumed the "friend" in the second half would be another guy.
George and Michelle are gently ribbing me at the bar and asking me when we're going to do this. I told George privately that I was having misgivings about "Part Two." George is a devoted fan of your column; I've seen your musical "The Kid," so we know who you are. George suggested I write to you and have you make the decision about whether or not I've fulfilled my obligation sufficiently. My defense is that no one stipulated a woman would be involved; George's is that no one stipulated a woman could NOT be involved. I can tell George is very keen on going through with this and thinks you will back him up. What I don't understand is the depth of his enthusiasm. He by all accounts is a 100% red-blooded heterosexual man, although I will concede that he does enjoy pranks and yes, wagers, so this isn't entirely out of character, I guess.
I have told no other friends about this situation and George and Michelle have assured me that they are keeping it private as well. I believe them.
What do you think I should do? We have all agreed to abide by your advice. I will have to work with George, and I don't want to avoid Michelle and my favorite bar, but the wager was my idea to begin with, so I think asking a third party to possibly mediate my dilemma is a reasonable and fair solution. Also, I am aware if I renege on this, I'll never be able to get George is a situation where the tables are turned, and I'd very much like to get my sweet revenge. But bottom line, the thought of doing this again in front of two people, one a female, is sweat-inducing, big time. George has informed me that, with Michelle, he has developed "one or two new ideas." Also, I would be required to do this at Michelle's apartment, which for some reason adds to my discomfort about the whole thing.
I realize this is a very long letter but (a) it was hard to stop once I started writing it, (b) I guess the more you know about this situation, the better. (George has read this and even added a few items—the graphic stuff is mostly all his).
What Have I Gotten Myself Into?
Allow me, Commenters: FAKE! FAKE! FAKE!
But nevertheless, and without a doubt, this absolutely epic letter is the "Savage Love" letter of the day. And on the outside chance that this letter isn't a fake—which it most definitely is (FAKE! FAKE! FAKE!)—I think you should honor the terms of your oh-so-humiliating bet, WHIGMI, and masturbate when and where George requires you to, and in front of whomever George selects, per the terms of your idiotic and almost certainly fictional "bet."
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