Fantasy Football Fun

One of my fantasy football leagues consisted of a group of coworkers from a past company I worked at. Actually the majority of people no longer worked for the company, but it was a good way to keep in touch and hang out with friends. The league consisted of 10 people. We had 5 guys and 5 girls and no one took it too seriously, it was all in fun. For our draft, we rented a conference room at a hotel and at the end of the season we all met at someone's house and had a party. We invited others we worked with in the past as well and the party often went well into the night. This was the sixth year of our league and consequently our sixth end of the season party. After this season though, I'm not sure the league will ever be the same.

It was nearing midnight and the party had been going on for 12 hours now. Only the die-hards remained and we had all had plenty to drink. We had an even number of guys and girls and we were standing around in the kitchen, still sipping on our drinks and nibbling on the leftovers. I was talking to Jack, Kevin was talking to Jenni, and Samantha (who goes by Sam) was chatting with Mandi.

All of a sudden Sam yelled, "Oh my God, go get it!" Everyone turned to find out what the commotion was and Sam said, "Mandi is selling sex toys!" It seems that Mandi had started having those parties similar to Tupperware parties but where the women instead buy sex toys. After some prodding from Sam, Mandi went to her car and brought in a case of her items. She asked us what we wanted to see first. Jenni said, "What's the biggest dildo you have in there?"

Mandi reached in her bag and pulled out this large black rubber dildo. It was realistic looking with a circumcised head and balls to match. She set it on the table and it wobbled as she set it down. The thing looked huge. She told us it was 9 inches long but I have to say it looked about a foot and a half to me. I never considered myself a small guy but I was nowhere near the size of that thing neither in length nor girth.

Apparently, I was not alone. While Sam and Jenni fawned over the large fake cock on the counter, Kevin finally said, "I'm not sure how realistic that is." Sam laughed, "Are you kidding? This is average. Are you saying you don't measure up?"

Kevin laughed and said, "I think I do just fine, but I don't think that's a realistic expectation is all I'm just saying." Jenni giggled and said, "I think Kevin is intimidated, he's not used to seeing such a magnificent specimen."

I had to speak up at this point; I couldn't leave Kevin out to dry against this onslaught. "Come on guys, it's obvious that it isn't average. It's oversized to make a point." I shouldn't have said a thing. Sam turned towards me and said, "Apparently we have another one who just doesn't measure up. " I immediately felt my face blushing.

Mandi, then joining in on the momentum said, "We should have a contest. Let's see how everyone measures up." The looks on the faces of Sam & Jenni showed they thought this was the greatest idea they had ever heard.

Jack asked, "What's the contest entail?"

The girls huddled up for a couple of minutes as Jack, Kevin & I waited. They came back and Sam announced "We are going to measure you three and see who stacks up to this guy (as she picked up the fake dildo). We'll measure for length, girth and (with a devilish grin) which one feels the best...in our mouths."

Obviously this was starting to sound like a great idea. Jack asked, "What are the stakes?"

This time Jenni spoke up, "The winner, he gets to finish in whoever's mouth he wants. Obviously, if we're impressed enough, it may be more. Whoever is last, Mandi has a paddle in her bag of goodies; let's say that we get to use that on him tonight. That sound good?"

Jack immediately said he was game but Kevin paused. It was clear he wasn't sure. I felt this would help my chances. After all, there had to be a reason he wasn't confident. All three girls gave him a hard time before he finally relented. When it came to me, I said that I would play along, as I figured I would be able to at least hold my own versus Kevin.

Sam suggested that we all do a shot to help everyone's confidence. Jack laughed and said, "You guys should do a blowjob shot since that's what you three will be doing soon. Give us some inspiration." The shots were poured; all the guys took one before watching the gals do their blowjob shots. Everyone did one more round and then Mandi said, "All right boys, let's strip down."

Kevin, Jack & I all slowly stripped down until we were all in our boxers. Jack then suggested to up the stakes a little more. "Let's say the winner gets his choice of how he wants to finish." The implication clearly that he wanted to fuck one if not more of the girls. Sam said that's fine, but what's in it for us? Finally Mandi said, "how about the loser has to do whatever us girls tell him the rest of the night? To be our slave!" The shots clearly had gotten to all of us and we all agreed.

Sam then said, "Ok one at a time, let's see what you boys are packing. Jack you're first."

Jack put his thumbs in his waistband and lowered his boxers. He revealed a cock that was easily the same size as the one on the counter. I couldn't believe it. It was not even erect and I was in shock. Mandi spoke first, "Well, looks like this game is about to get interesting."

Kevin was next and I knew that I'd not in any way be able to beat Jack, but I held out hopes that I would be able to beat Kevin in at least one of the categories. "Let's see what you have Kevin," Sam teased.

Kevin then lowered his boxers as well and while he wasn't the size of Jack and the dildo on the counter, he was easily bigger than I was. I was in trouble and there was no way out of this contest. Another thing I noticed was that I was clean shaven and neither Kevin nor Jack was. I had always enjoyed the look and feel of being shaven but in this situation it seemed like it was only going to put me more on display.

When it was my turn, I tried to stall but Sam was having none of it. She walked up to me my balls through my boxers. "Come on Brian, let's see what you got." With that she lowered my boxers revealing my shaven cock.

There was not the same excitement for me as when Jack and Kevin had exposed their cocks. Finally, it was Jenni who spoke, "Well, it seems we know who will be filling the slave role tonight. Guess this is going to be a two man contest."

The next 10 minutes consisted of the girls measuring both Kevin and Jack with Jack winning on length and Kevin winning on girth. I had to watch as each of the girls knelt down in front of Kevin & Jack as they took their cocks in their mouths and started bobbing up and down. Mandi, Sam and Jenni all started with Kevin and then went on to Jack. When they got to me, Mandi said, "Sorry Brian, you've already been eliminated, it really isn't worth my time to even try." Sam cupped my balls again and squeezed them, and said, "It's not really a man's cock. A little boy's maybe." And Jenni just giggled and said, "Its ok Brian, or should I say Brianna,we'll find some use for you tonight, though I doubt that little cock will be in much demand."

Eventually it was ruled a tie between Kevin and Jack and it was determined they'd both be able to cum anyway they pleased. While I was clearly humiliated I was hoping that Kevin and Jack would finish quickly and the night would be over. That wasn't meant to be.

Sam said, "Ok before the winners get to claim their prizes, we first have to administer the paddle to the loser. Brianna, why don't you and your tiny cock come over here by the couch and bend over it."

I slowly walked across the room and bent over the couch, my humiliation growing with each second.

Jenni said, "10 swats each sound about right?" and everyone quickly agreed (except for me).

Mandi went first and she proceeded to give me 10 solid slaps with the paddle, I could feel my ass growing warmer with each swat. Jenni then said, "Look at that, his little cock continues to get hard as he's paddled!" Sure enough, the combination of being exposed like that along and having my ass paddled had made my cock grow as hard as could be.

I proceeded to take the remaining 20 swats from the paddle with minimal taunting although everyone was impressed with how red my ass was afterwards. As soon as I turned around though, the teasing started again when Sam said, "Look at that little thing, so pathetic."

It was then decided that since there were three women and only "2 real men" that I would have to please one of them with my tongue. I wasn't opposed to this at all, as I had long hoped to be between the legs of any of these women.

Sam took me by the back of my neck and led me to the couch and said, "Kneel here pussy boy" as she started to disrobe. Soon enough Sam had stripped down, revealing her fabulous breasts which I had long lusted after. She sat down in the couch and said, "Ok start licking me slut" as she pulled my face forcibly between her legs. My tongue dove deep into her as she wrapped her legs tightly around my head.

I could hear both Mandi and Jenni moaning in the background as I assumed Jack and Kevin were filling both of them up with their large cocks. Before long, I could feel Sam's body tense up and her legs wrap even tighter around my face and I knew she was cumming. Sam pushed me back and said, "Oh I wish you had a real cock on you instead of that little pathetic thing."

At that point, Mandi and Jack had just finished. Mandi sat down next to Sam and pulled me between her legs. "Lick me clean," Mandi said as she buried my face into her pussy, "taste what a real man can do." I had no choice but to lick her. I could taste Jack's cum as I licked her pussy clean. I continued licking both her juices and Jack's until Mandi was brought to another orgasm.

As she came she allowed me to sit back and catch my breath. My face was covered in her juices and Sam and Mandi both giggled as Sam said, "Face covered in cum, that seems natural for a guy with such a tiny cock. Thankfully his tongue is worth something."

Jenni and Kevin walked into the room, clearly both having just orgasmed themselves. Mandi said, "Brianna, looks like there's one more bit of cleaning up for you to do" as she pointed towards Jenni. As I kneeled on the floor, my cock leaking precum non-stop, I looked up at Jenni and admired her body. She sat down on the love seat across from the other two women and spread her legs.

"Come on over here tiny, come lick the cum out of my pussy, drink it all up, you know you want it," Jenni mocked. As I crawled over to Jenni, I heard Sam and Mandi talking about what else Mandi had in her bag of goodies. I heard Sam say "Oh yes, let's do that!" right as Jenni pulled my face into her pussy.

If I thought Mandi's pussy was full of cum, that was nothing. Kevin had deposited quite a load and she was making sure I was licking it all up and wasn't going to miss a drop. "Lick me clean you little slut, since your cock isn't worth anything, your tongue is going to have to make up for it."

At that point I heard Sam say, "Ready Jenni?"

I was confused but kept licking; soon Jenni was cumming all over my face. She pulled my face in and held me there. When she was done, she leaned forward and said, "Now you're going to feel what a real cock is." And she pulled my head back to her pussy.

I felt a cool liquid substance on my ass and before I knew it, I felt something trying to be pushed into my ass. Then I heard Jenni say, "Oh yes Sam fuck him with it." I thought I was going to be split in two but Sam kept pushing the dildo into my ass. Each time she pushed a little more, I'd gasp and Jenni would pull me into her pussy smothering me.

Soon the dildo was fully in my ass and Sam started thrusting. Jenni was moaning out as each thrust pushed me into her pussy more. I could occasionally hear Jack, Kevin and Mandi all cheering Sam on. "Fuck his ass." "Deeper, pound him hard." "Take it all Brianna!"

While I wanted to hide more than ever, I couldn't believe I was getting fucked by a plastic dildo in front of three of the hottest women I had ever met and two guys with monstrous cocks but I was starting to enjoy it. I could feel my cock getting harder and harder.

It was confirmed when I heard Mandi exclaim, "Look that little cock is getting hard, he likes being fucked up the ass!"

That caused Sam to thrust harder and deeper and before long my cock started to spurt, I couldn't hold it back. This caused everyone in the room to laugh.

Jenni leaned back and let me breath easily again and Sam stopped her thrusting. She slowly pulled the huge cock out of my ass and slapped me hard on my sore ass. Sam then leaned in and said, "That's what happens to pussy boys with tiny cocks who could never fucking satisfy a woman. They end up getting ass-fucked like a little whore. Get used to it Brianna."

Jenni then pointed down at the puddle of cum on the floor from where I came. "Lick it up; maybe eating enough cum would turn you into a real man." I slowly bent down and began to lick up my own cum as everyone laughed at me doing so.

The night ended shortly thereafter with everyone basically falling asleep on the couches in the next 15 minutes. I slept by myself in a chair away from everyone else. I woke up early in the morning and attempted to sneak out of the house. I had hoped that everyone had as much to drink as I had and hopefully wouldn't remember anything that happened. At the very least, I hoped it would never be brought up again.

I was halfway home when my cell phone went off. At a stoplight I looked at it and it was from Sam. It read, "If you think I'm waiting until next year's party to fuck your ass again, think twice Brianna."