Spreading Christmas Cheer Pt. 04

After lunch with David, I returned to my room for a nap. My body was tired and asking for mercy. Being much more successful this year then the prior two years of competition, my body could tell the difference. I'm only 29 years old. I shouldn't be this out of shape for sex. I wondered how bad it would be next year. We were booked at a resort in Palm Springs, CA.

I heard the phone ring. It was 5:15 and I'd napped for two hours. Not enough. The caller identified himself as Shaquan, the dude from yesterday.

I said, "Hey Shaquan. What's up?"

"Jackie, I have a challenge for you if you can handle it. I have six brothers lined up for tonight if you can take them on. I can cancel some of them if that's too many."

"Wow, that's a lot. Do you know how big their cocks are?"

"I've seen only two of them in action with my baby mammas and they're not as big as me. Let me dial in Travis. I think he knows the other four better than I do."

In just a moment, Travis joined the call. "Hey Jackie, Shaquan just told me your question. Another three played basketball with me and we showed together many times. Their cocks are nothing special, probably six to eight inches when fully inflated. The old fable about all blacks having big dicks is not true. Now the other guy, I've only seen once. He was busy fucking a big momma that I know for sure has a huge pussy." He laughed and added, "She's had so many kids that her pussy must be a big as a throughway tunnel, and probably as busy. He was long but not that big around. I'd say twelve to thirteen inches. That thick black momma could probably handle three of him at a time."

I replied, "I'm willing to try it. Get them over here at 8:00 and I'll lay out the rules when they come." I knew that, if successful, this would secure the win and give me bragging rights for a year. The longest train I'd pulled during my sorority parties was five men. Another sister pulled six that same night. Alex was in another sorority but hung out with me. Her sorority was famous for pulling longer trains. It was possible Alex had one organized for the final night. Deb was not known for taking more than two men at a time, so I didn't worry too much about her.

I took another shower at 7:30 and stacked up fresh towels for the guys to use. The bathroom was going to be very busy if my plan came together. The key was to keep the train moving and not let anyone pound me for five minutes or longer. I thought carefully about how to do that.

When the six arrived, they were an impressive group. All were black but many shades of black were represented. I had them take a seat on the sofa or the floor as I explained the rules.

"Guys, I'm glad you could help me out tonight. As you probably know, I'm competing with two to other women these last two days to see how many sexual encounters we can tally in 48 hours. I'm currently ahead, I think, but with your help tonight, I should be able to win.

"Now here's the rules. If you can't live with them, then leave after I explain them. I think you'll find them fair and fun. First, I want you all to undress and masturbate while I show you my body and pussy. I want to see how big your erect cock is. I will then choose the order in which you can fuck me. There will be no cutting in line. To help you keep your erection while I'm being fucked, I'll suck off as many of you as I can. Now, because I'm pulling a big train tonight, I can't handle you each fucking me for fifteen minutes at a time. I'm sore already. So, to encourage you to cum quickly, I will give $5000 to the guy who can cum the quickest after entering my pussy. Second fastest will win $3000 and third will win $2000."

One guy said, "Damn girl. I've never been paid to fuck a woman."

Another added, "Well, you ain't been paid yet. Just hold my beer."

I continued, "So we can accurately time you, pull your cock out and shoot onto my stomach. That will stop the clock and record your time. If you shoot inside my pussy, we'll not be able to determine your time.

"Before we begin, strip and let's see what size equipment you carry. To give you encouragement, I'll lay over on the bed and show you my equipment. Look but don't touch."

Everyone stripped while bragging, joking and laughing filled the room. On the bed, I spread my legs to show a hairless treasure box. By pulling aside the outer labia, the guys could easily see all the pink interior and the opening to the treasure cave. The masturbation began. It took a good while, but all finally declared they were fully erect.

By quickly walking around and assessing the sizes, I put the guys in order from smallest to largest cock. Like Travis had said, one of the guys was huge, easily twelve to fourteen inches long. I would try him last.

When everyone knew their position, I asked them to choose a timekeeper. The guy with the giant dick was chosen since he was last in line. I handed him my iPhone that had a stopwatch app and let him practice.

"Now guys, I don't have any rules requiring condoms, but I do want you to be clean before we screw. Please go to the shower and wash your genitals carefully. There are plenty of towels there."

Each filed in to shower and cleaned themselves. Once all were finished and re-assembled in order, I said, "Let's begin. Number one, get your cock stiff and come on the bed when you're ready."

I asked the timekeeper to take a photo of each cock as it entered my pussy. I explained that I needed proof of each encounter. He agreed.

When the first man was in position, the timekeeper said "Go." He took a photo as this black dick burrowed into me.

He was fast and furious in pounding my pussy. One of the others moved onto the bed for me to suck his dick. I played with his balls and stuck my finger in his asshole at the same time. He was ready to shoot without even entering me.

Suddenly the first guy moaned and pulled out to eject his spunk. The timekeeper called out, "Three minutes and twenty-eight seconds."

Number two crawled between my legs and said he was ready. When the signal was given, he slowly entered and used his hand to help milk his cock as it entered again and again in my vagina. I thought that was ingenious. He was giving himself a hand job and me a pussy fucking at the same time. Shit, why didn't I think of that? His time was four minutes and one second. I guessed the hand job wasn't so great after all.

Number three stepped to the plate and flexed his muscles for all to see. With a last minute hand stroke of his eight-incher, the signal was given and in he went. I could tell the bigger guys had arrived. His stretched me.

At that point, I could only lay back and focus on tomorrow and me claiming the victory. I was hurting but determined as his thrusts bottomed out and shook my breasts. My brain was foggy, but I heard his time called at three minutes and forty-one seconds.

Number four climbed on. He was the one I'd sucked and fingered earlier. He leaned forward to whisper something. I listened carefully and nodded my head. He had a plan. I smiled.

When the signal was given, he went in for a couple of seconds, withdrew and turned to show me his ass. As instructed, I stuck my finger deep into this rectum to massage his prostate. With my other hand, I jerked down repeatedly on his dangling cock and sucked his balls into my mouth. He shot a massive load in two minutes and fifty-nine seconds, a new record. It covered my stomach and the towel I was laying on.

The crowd erupted "Cheater, you bastard, that's not in the rules, asshole."

I quieted the crowd and reminded them of the rule. "What I said is you must fuck my pussy and pull out before you shoot. Nothing was said about prostate massaging and using my hand or mouth to assist. In fact, I volunteered to suck you off to get you ready." Everyone grumbled but admitted I was right.

Number five came to the plate and asked me to do the same thing I did for number four. He was determined nobody from the hood was going to beat him. After spending less that ten seconds in my pussy, he turned for me to massage his prostate and milk his erection. He shot in three minutes and three seconds.

Finally, the one I'd been dreading. He was ready with his giant pole sticking straight out. He moved into position and the signal was given. He went in but only about eight or nine inches and stopped. He then masturbated the back half of his cock while studying my breasts and sweaty face and feeling the warm welcome in my vagina. He pulled out and ejaculated in two minutes, thirty-one seconds. The winner!

After cleaning all the cum off, I walked to the safe and removed the cash to pay the winners. I also gave the losers $100 each as a participation trophy. All left happy and wished me a great Christmas. As one guy said, where else can you fuck a beautiful woman and get paid for it? Only in the movies.

I totally crashed that night. My plan worked and those six brothers spent a combined time of less than 17 minutes in my vagina and no sperm were in me. I dreamed of getting back home to my husband and getting fucked only every week or two. His hidden mistresses would take my place on other nights.

End of Part 4