Flashback – Glory Hole Roulette

I fixed myself a cup of tea then pulled up a seat at the kitchen table. Everyone was still very silent and in their own deep thought.

I sat there with a bit of guilt in my heart. I wasn't always the angel that Mom always thought me to be. If she knew the things I did in my high school and college years, she would have died of shame. As I sat there in silence with the others, my mind drifted back to a specific moment that involved David from back when I was in college.

FLASHBACK TO OCTOBER, 2000:

I was in my first semester of my graduate studies at Duquesne University. I was dating a guy named Darren, who was in his second year of a graduate law program. Darren took his studies very serious, but he also liked to party as often as he could. Me and most of the girls in my dorm also took our studies very serious, so none of us really had time for a job.

Several girls in my dorm took lead from gossip that girls at many colleges around the country were having secret sex parties to raise money. The rumors were that thousands of dollars were being collected each night for events ranging from strip shows, to sex games, to all out orgies. The girls in my dorm were very innovative. They came up with a sex game called Glory Hole Roulette. The game gained its name from the idea of Russian Roulette and a recent craze of what was known as glory hole sex.

Each event would typically raise $4000, which was divided equally among the 10 girls that participated. To keep things consistent and under control, there was a set number of participants, 40 guys and 10 girls. Each guy would pay $100 to participate. A designated dorm room would be divided in two by a retractable wall made out of several pieces plasterboard. There were four appropriately spaced out glory holes cut into the plasterboard, each labeled with a different sexual act…hand job, blow job, pussy sex and anal sex.

For the guys it was simple, pay your $100 and you are guaranteed some action. But for the girls, it was actually like work. Each girl would work hard to earn her $400.

Here is my best explanation of how the game was played:

There were 10 rounds to each event. The basic object of the game was that once the 4 guys in each round placed their dicks through the glory hole, the girl on the other side had 15 minutes to make that guy cum by means of the sexual act drawn (hand job, blow job, vaginal or anal). The penalties for failure to cum after the 15 minutes were: the girl was guaranteed a harsher sexual act in the next round, while the guy just paid $100 for blue balls.

The 40 guys would all gather in a common room, separate from the glory hole room.

Each round, every guy that remained would draw a chip out of a satin Crown Royal bag. If he drew a blank chip, he had to wait until the next round to draw again. If the chip had a marking, it meant that he got to participate in that round. The marking on the chip determined what sexual act would be performed through his glory hole. ('hj' hand job, 'bj' blow job, 'ps' pussy sex, or 'as' anal sex). Once a guy participated in a round, his night was over. After each round, 4 blank chips would be removed from the bag, representing the 4 guys who had their turn and were now out of the game. There were no second chances, no do-overs, no other turns and absolutely no refunds.

The 10 girls would all gather in the room where the glory hole wall was set up. Each round, all 10 girls would draw a chip out of a satin Crown Royal bag. All ten chips in the bag were marked because all 10 girls had to participate in all 10 rounds to earn her $400. The marking on the chip determined her task for that round.

'M' stood for Moderator, which meant she collected the money from the 4 guys for that round; handled the chip drawing for the guys; handed out condoms; kept the time clock; upheld the rules of the game and recorded any violations.

'R' stood for Referee, which meant that she upheld the rules of the game and reported any violations to the moderator for review. The most important rule was neither side was allowed to talk, to keep the element of mystery and anonymity. Also, at no point was the guy allowed to remove the condom. It had to be removed by the actress or a clean-up girl. Violation of the rules resulted in a harsher sex act in the next round for the girls, and a suspension from the next event for the guys.

'C-U' stood for Clean-Up, which meant she cleaned up after the round; disposed of the condoms and washed and sanitized around each glory hole. There were 2 clean up girls drawn for each round.

'F/R' stood for Fluffer or Rouser, which meant that her job was to make sure that the 4 guys participating in that round were completely hard and ready to go before they stepped up to the glory hole. She would do so by any means possible, whether it be stripping, lap dancing, physical contact or even oral. There were 2 fluffers drawn for each round.

'HJ' stood for Hand Job, which meant she would be the first position at the wall. She had 15 minutes to make the guy cum by giving a hand job. It was at the girl's discretion whether the guy had to wear a condom or not. If the guy failed to cum after 15 minutes, that girl was guaranteed the Blow Job position in the next round.

'BJ' stood for Blow Job, which meant she would be the second position at the wall. She had 15 minutes to make the guy cum by giving a blow job. Again, it was at the girl's discretion whether the guy had to wear a condom or not, however, no matter where the load was blown, you had to show proof that he came. If the guy failed to cum after 15 minutes, that girl was guaranteed the Pussy Sex position in the next round.

'PS' stood for Pussy Sex, which meant she would be the third position at the wall. She had 15 minutes to make a guy cum by way of vaginal sex. Condoms where mandatory for this act, no exemptions. This was probably the most difficult act to succeed at because it was difficult to position and maneuver comfortably. If the guy failed to cum after 15 minutes, that girl was guaranteed the Anal Sex position in the next round.

'AS' stood for Anal Sex, which meant she would be the forth position of the wall. She had 15 minutes to make a guy cum by way of anal sex. Again, condoms where mandatory for this act, no exemptions. The use of lubes was allowed, and quite common for this act. If the guy failed to cum after 15 minutes, that girl was guaranteed the Anal Sex position again in the next round.

I knew of Glory Hole Roulette since the day it was invented, however, I almost opted to not partake in the events because I had a boyfriend. It turned out that when Darren found out about it, he urged me to participate, as long as he got to join in too. My Christian upbringing and guilty conscience still had me second guess whether or not I should participate, until I realized that my savings account was down to a zero balance. The $400 for one night of work was too good to be true. During the first few times the event was held, there was a lot of nervousness and confusion which resulted in mistakes and mishaps. By the third and fourth time, everything became routine for all of us.

It was mid-October of 2000, and my brother David was having trouble meeting new friends at his college of choice, Robert Morris College. So one weekend, Darren invited him to come party with us. I told Darren there was no way I was going to let David participate in Glory Hole Roulette.

Darren reminded me that in the 5 events that had been held to that point, not once did the two of us end up drawing the same hole. We knew this because we both knew each other's bodies very well, specifically Darren's extra thick cock. One time I drew the Hand Job chip and had to sit there and watch one of my best friends blow Darren's fat cock while I jerked off some guy's small dick. It was torture, but I then I would just think about the money and I would get over it.

Anyway, on this particular weekend, the event wasn't being held until Sunday night, so I figured I was in the clear. David had shown up Friday and partied very hard with us all through the weekend. He saw his big sis do things that he probably never thought he would see. He saw me do beer bongs, smoke weed and even do a few lines of coke. Both nights he passed out in my friend Shannon's room, but I am sure he overheard me and Darren having sex. I'm sure that the entire floor of the dormitory heard us. We didn't hold back from making noise, especially when we were stoned or drunk.

When Sunday came around, David started asking us about this glory hole sex game at the dorms that costs $100 and guarantees him to have sex. I told him that it was bad news and he shouldn't think twice about it. That afternoon, we parted ways, and I figured that David went back home. The evening came and I prepared myself for the night's event.

For the first three rounds of the game I drew the Blow Job chip. I cared about protection, so I always opted for the guy to put on a flavored condom during the blow job. Most guys hated it because it made them less sensitive, but I still always made them cum. That is until the guy in the third round.

As it got closer and closer to the fifteen minute mark, I sucked and stroked as fast as I could, but he just wouldn't cum. The time limit ended, and I knew the guy was upset. I heard him punch the wall and yell something about it being bullshit that I made him wear a condom. His loss, the two guys before him didn't have any problem. But I was upset too. This was the first guy I was unsuccessful with. Now, it meant next round, it was mandatory that I had to do vaginal sex.

As I approached the wall for the next round, sticking through of the 'Blow Job' hole, I noticed that unique, massive monster that was Darren's cock. I was so upset, because I knew for sure that it was Darren and I was going to have to sit here and watch another girl blow my boyfriend again, while some stranger fucked me.

As a swollen prick finally poked through my 'Pussy Sex' hole, I noticed that it quite larger than most that we see. It wasn't comparable to Darren's in girth, but it was certainly longer and well proportioned. Because of his good length, I knew I would be able to position myself better than usual and take him on from different angles if necessary.

As the bell rang to indicate the start of the round, I grabbed hold of the dick and quickly worked it into my slightly moist pussy. I would not fail this time. I did not want to get bumped to the anal sex hole for the next round. As I slid this massive pole in and out of me at a quicker rate, I felt my juices begin to flow. Then I could hear faint conversation coming from the other side of the wall. I could tell it was Darren.

"Dude. How are you enjoying it?"

Usually the 'Referee' would warn the participants for talking, but Darren was well liked by all the girls and could typically get away with it.

"Oh my god, she feels amazing. Her pussy is getting so wet." The other voice whispered. I was slightly flattered.

Then I heard Darren say, "Dave. I know the one sucking me right now is definitely Colleen. I know that mouth like the palm of my hand."

Reality set in and I started to freak.

David replied a little louder, "What? Colleen does this. You mean Colleen is over there right now. She can see me?"

Darren interrupted, "Shhh. Keep it down...Don't worry man, she doesn't know it's you."

I knew now. Holy shit! It was my brother's dick buried deep inside me.

In a panic, I almost pulled away, but I was aware of the consequences if I did. I couldn't risk losing my $400 pay. I must have become a dead fish for a minute or two as I battled my conscience. I finally convinced myself that there was no way he would ever find out. Besides, it did feel amazing.

Every muscle in my body tensed. I pressed my ass against the wall, getting my pussy as close to the hole as possible. David took lead and started pumping in and out of me from the other side of the wall. I could feel and hear my fluids splashing out of me with each push. Then my entire body chilled over right before an eruption of heat in my pussy blasted an orgasm throughout my entire body. The spasm of my muscles around David's cock must have been too much for him. I felt him stiffen behind me, give a few more quick pumps, then unleash his load into the tip of the condom. I let him remain inside me for a few moments until he softened a bit and fell out of my drenched cunt.

I turned around, removed the condom, verified the cum with the moderator, then dropped to my knees and took the softening cock into my mouth. It wasn't typical to do anything after you made a guy cum, but you were free to do what you wanted with the remainder of the 15 minutes. I don't know what possessed me to do so, but I wanted to taste my brother. I licked and sucked the swollen head of his dick until his shaft was completely stiff again. I took as much of his length into my throat as I could handle. I bobbed up and down on his cock for at least 3 minutes straight without taking a breath. The suction and throat noises were loud and obnoxious. I know everyone in the room could hear. Then I felt him tense up in my mouth as he began to unload stream after stream of cum into the back of my throat. I gulped down every last drop, then pulled away to get cleaned up.

Darren and I never would talk about things that would happen during Glory Hole Roulette as to not jeopardize our relationship. I never discussed that night with anyone, not Darren, not my girlfriends and especially not David. Some things you just have to keep a secret forever. I never participated in another Glory Hole Roulette again after that night.

RETURN TO PRESENT (NOW DECEMBER 23, APPROXIMATELY 1:30AM)

I snapped back to reality, stood up from my chair and noticed that beneath my robe, my tank top and panties had become completely soaked again. I looked around the table to realize that Dad was passed out in his chair snoring, Darren had gotten up and left the kitchen, and Mom was staring into space with that same look of disgust on her face. A sense of guilt overcame me as I leaned over Mom, gave her a hug and a kiss, and walked off to bed.