"Gambling Isn't My Strong Suit" by Guest Author, mnmstr
It was a chance meeting in the airport. Home for the holiday I was headed from the terminal to the bus stop when heard someone shout my name. It was Andrew. Andrew Foster. We sorta knew each other from school. Not friends, not even Facebook friends, just knew each other. He was at the airport dropping the family off. Every year they went to whatever place rich people go for Thanksgiving. This year his trip ended curbside. "I have stuff to do." was his only explanation. What did it care? It saved me from taking the bus.
"We should get together for a beer" I said as he dropped me off. A statement made more out of courtesy rather than an actual invitation. I had no expectations of hearing form him again.
That made Saturday night a welcome surprise. Home with parents lost its novelty. I was a little antsy, looking for a reason to get out of the house. Andrew's call provided the diversion I was looking for. "I got the house to myself, come over for a couple of beers." I was so bored a club soda would have gotten me grabbing for the car keys.
We kicked back, grew tired of TV, started playing cards. Playing? Andrew may have been playing. I was losing. I think we were two beers into our second six pack when my cash ran out. I was just drunk enough to agree when Andrew suggested I wager my clothes to stay in the game. Strip poker? It was a bad idea, an exceptionally bad idea, given the way my luck was running that night. Then what did it matter if I lost? Losing didn't seem that bad compared with the chance that I might see Andrew naked. Several girls had told me he was blessed with more than good looks. Here was rare opportunity for confirmation.
My plan was "Andrew naked". My cards left him sockless and me naked. If I had been smart I would have called it quits. He proposed one more hand, all in, with my ante "no cumming for a year". Hah, that was a joke. Sure, I agree to that. What was he going to do? Put a camera in my room? Struggling to contain my laugh I signed the "IOU" Andrew produced to insure my bet. I wagered and lost. It was no big deal. I killed the last beer before asking for my clothes back.
He playfully refused to return my clothes. "Don't you feel more comfortable naked?"
"What is the rush? Why do you stay for awhile?" We joked about it. Was he hitting on me? The idea that made me embarrassingly hard which, for some reason, made him want to measure my package. Thinking things were starting to go somewhere I let him take his measurements. Nothing happened, all he actually wanted to do was measure my junk. Turned out he liked me naked, just not naked in bed.
That was the last I heard of Andrew until Christmas. "Stop by, I got something for you." I showed up determined to keep my clothes on this time. Same as before we chatted, drank, watched some TV. He produced the "gift", The small, neatly wrapped box provided no clue to the contents. Opening the box did not help either. My confused “Thank you” told Andrew I had not idea what the small, metal cage was for. "It's a chastity device. This is going to help make sure you keep up you side of the deal."
"Put it on see if it fits."
For the second time I stood naked in front of Andrew, this time only to have him stuff my cock into a metal cage. My plan was to claim the device did not fit then take the device and sell it on the Internet. It looked kind of expensive. Problem was it did fit. It actually did not feel bad at all. Andrew squashed my planned defense before I even had a chance to present it. "Fits perfectly. Be back for my New Years Eve party.'”
He took it off and that was it. I dressed and headed home. For the next three days I stoked myself wildly. No way was I going to be locked up but the idea was kind of hot so I got as much mileage out of the idea as I could.
New Years Eve and everyone was headed to Andrew’s. There was no way I was going to miss the party. It was my last chance to mingle before everyone headed back to school. I arrived late to a full house. The crowd was big enough that it was easy to avoid Andrew. It was harder to avoid the alcohol. One beer became two plus a shot. I lost track of time somewhere in my second game of quarters. Midnight ... I think I remember midnight.
Normally I am not the kind of guy who wakes up naked in a strange bed with a hangover. Actually I never have before that’s why I will always wonder how I happened that I wake up in Andrew's bed that morning. Boy did I have a headache.
"A little hung over is my guess." Andrew sipped coffee in a nearby chair. "You were really putting them away last night."
"I guess." I muttered. "I should be getting home. Where are my clothes?"
"Around here somewhere I am sure. Why hurry, it is a holiday so relax a little. Get up we'll have some coffee."
"Well get me my clothes and I will." Andrew was unmoved by my request.
"Don't worry, you don't need clothes, it is not like I will see anything that I haven’t seen before."
Knowing this was going nowhere I glared at Andrew as I rolled out of bed.
"What the fuck?" I stared down at steel cage that now enclosed my cock.
"Oh, you mean the shave. Yea I took the liberty, you may find it easier going if you keep yourself shaved."
"The shave, fuck the shave, I talking about the god damn cage you asshole. The keys now!"
Andrew faked surprise. "The cage? What do you mean the cage? Today is the first day of the year. You owe me a year without cumming." Andrew waved the IOU in the air.
"You got to be fucking kidding me, that paper was a joke and we both know that."
"Not the way I see it. I won the bet so you owe me. If I lost and did not pay you be pissed at me. It works both ways."
I just stared angrily back at him more pissed at myself then at Andrew. I was foolish enough to make the bet then was dumb enough to fall asleep at his house.
"My clothes please."
"As I said you have no need for clothes. There is nothing that I have not seen before. Now lets go get you some coffee."
Angry, ashamed, humiliated, locked I followed Andrew out of the room.
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