I’m screwed. I was so fucking cocky I made a bet thinking there was no way I would lose. And what happened, I lost. Now my male colleagues and I are going to have to pay up.

My name is Richard (Rich) Gilliam, and I’ve been the best salesperson in our region for several years. I’ve had a long history of winning. I am a winner. Or should I say, I was a winner.

I graduated at the top of my class from an Ivy League university and a prestigious business school. I was hired as the lead salesperson for CorePath Software in the East region’s Finance and Banking sector — their largest sector. CorePath is a small start-up software company selling across industries in the USA. Our products are new and innovative, and the company is experiencing rapid growth. I was given the largest quota on the team and was personally responsible for sales in the company’s largest industry segment. I’ve consistently exceeded it every year since I started. In 2006, my first year, I doubled my quota. In 2007, my quota was increased, and I doubled the new number. I was getting cocky and thought I was the best sales person on the planet.

CorePath Software is a small start-up, and as such, we have a relatively small sales team. Our manager is Dana Whitaker. Under her, we are each assigned an industry segment with a specific sales quota. As I mentioned, I have finance and banking. Kimberly Fox (my nemesis) has Consumer Staples. While it is a smaller industry than mine, Kimberly has also been blowing away her numbers, but not by as much as I have. We also have Eric Dalton, who has the insurance industry, Elena Price, who sells to the Healthcare industry, Nick Voss, who sells to the Automotive industry, and Lauren Douglas, who sells to the Utilities industry. All of us are very young (in the 24 to 28 age range) and very aggressive.

At our end-of-year sales celebration event in 2007, I received a huge commission check and a bonus, and I was feeling very cocky. I approached Kimberly and challenged her to a sales contest for the next year. Obviously, straight sales would not be fair because some industries are simply larger than others, but we could make a wager based on our percentage over quota. Kimberly was aware of my results and was a little hesitant to go straight up, so she suggested that we hold a contest with the men against the women. The results for the three men (me, Eric, and Nick) and the three women (Kimberly, Elena, and Lauren) would be totaled to determine which sex was the better seller. Next came a discussion of the stakes. We didn’t want to talk about money; that’s just boring. So, I suggested that the losers have to strip naked and do whatever the winners want. The three ladies are beautiful, and I’d love to see them naked and have my way with each of them. Eric and Nick gave me a very scared look, basically asking, ‘Are you sure about this?’. I told them, “Relax, guys, I guarantee we’ll win.”

Well, my cockiness really pissed off Kimberly. She huddled with the other girls and then came back and said, “Okay, it’s a bet.”

I said, “Okay, after the year end, we will tally up the results and determine the winner, i.e., the men. The losers, i.e., the women, will get stripped and have to do whatever the winners want for 3 hours. There are 3 of you, and I think it would be nice for each of us to have each of you for an hour.”

Kimberly said, “Nice plan. Count those chickens before they hatch. We’ll win, and then we’ll decide what to do with the three of you. Better get yourself in shape. You’re going to be showing off your goods for 3 hours when this is done.”

*****

Well, I hate to admit it, but Kimberly was right; the 2008 financial crisis hit, and my year was a disaster. But not only was it my year; nobody was spending money on anything they didn’t have to. Banks were collapsing or getting bailed out. Banking was not investing in new software — it was out of the question. Same thing for Insurance. And Automotive was also a disaster; nobody was buying new cars. Not everyone met their quota. On the female side, it was the opposite. While it was not a great year for anyone, people still need Consumer Staples, Healthcare, and Utilities. The ladies won, and it wasn’t close.

Kimberly had the three of us sitting in my office while the ladies prepared the conference room for our ‘show’. I wasn’t sure what preparation was needed, but I’ll do it anyway.

Eric and Nick were giving me the evil eye. They blamed me for getting them into this mess, and I guess they are right. I said, “Look, Eric, Nick, we lost. Who could have predicted the financial crisis? Let’s just get through the next 3 hours. You know they will try to embarrass us, keep a positive thought, and don’t let them get to you. They probably are going to mainly go after me to punish me for being so cocky, so you’ll probably have it a little better than I will. And, who knows, maybe they’ll just want to have sex with us. That was what we had planned to do with them. We’re all good-looking guys. I’m approximately 6 feet 2 inches tall, weigh 180 pounds, and am in good shape. Eric, you’re a monster at 6 feet even and maybe 195 — all muscle. Nick was just under 6 feet and 175 pounds. We’re some good-looking beef. We may enjoy this as much as they do.”

Eric said, “I hope you’re right, but I doubt it.”

After letting us stew for a while, Kimberly came to get us and brought us into the conference room. The room was set up with some open space in front and three large tables spread around the room, with over 20 women sitting around the tables.

I said, “Wait a minute, this was between the 3 of us and the 3 of you, not over 20 women. This was not the deal.”

Kimberly said, “The deal was 3 hours with you doing whatever we want while naked. No mention was made of the number of people in the room. We get to decide that.”

I looked around the room and saw several familiar faces. Sitting front and center at the first table was our boss, Dana Whitaker. There was an empty chair next to her, which I assume was for Kimberly. Jennifer, my assistant, was sitting on the other side of Dana. Elena and Lauren each had the lead chair at the other two tables.

Kimberly explained, “While you’re looking out and wondering who all these people are, let me give you some context. These are people you see and interact with almost every day. Of course, you know Dana, Jennifer, and the three of us who whipped your butts in the contest. We also have Sheila, the head of marketing, whom you also know. Around the room, we have representatives from the development organization. I know you attended some of their briefings on our products. We also have ladies from the secretarial organization, the maintenance and cleaning team, and the call center. We also have some people who you might know from the area around our building. Several of the waitresses from the restaurants where you eat lunch are here. They tell me you tip by breast size, is that true? No need to respond. And a few others from businesses in the area that you have frequented. Everyone was very excited to hear that you would be performing for us.”

I said, “But wait a minute, there’s a guy back there.”

“Oh yes, that’s Jerome. He works at the hairdresser’s on the first floor of this building. I was there getting my hair done and inviting my hairdresser to join me. He overheard us and thought it sounded like fun, so I invited him too.

Okay, we’re almost ready to begin. However, before we proceed, I would like to give you one last chance to withdraw from this entirely, for your benefit and that of your colleagues. All you will need to do is answer one very simple question, and you can walk out of here fully clothed, leaving this whole group very disappointed. This is a question only for you, Rich, so please don’t seek help from Eric or Nick. Are you ready?”

I was so relieved. I did believe Kimberly when she said it was an easy question, so I thought I might have a good shot at this. I was starting to feel a bit confident again. “Okay, let’s hear the question.”

“As I just went around the room, I introduced all the different groups of people you interact with on a regular basis. Other than the three of us in sales, our manager, Sheila from marketing, your secretarial assistant, Jennifer, and Jerome, whose name I just mentioned, there are 17 additional ladies in this room. Can you name 3 of them?”

I looked around the room. So many of the faces were familiar. Kimberly was right, I did see these people all the time. But I had absolutely no idea what their names were. We’re screwed.

I said softly, “I can’t do it.”

Kimberly said, “Wow, that’s disappointing, especially for Eric and Nick. I thought salespeople were supposed to be good with names. I suppose you’re not very good at sales. But we already knew that from your yearly numbers.”

*****

“Okay, let’s get started. Why don’t the 3 of you line up in front of the room and strip off your outer garments? You can leave on your underwear for now.”

Eric, Nick, and I walked to the front of the room and started removing our sports coats, ties, shirts, slacks, socks, and shoes.

While we were undressing, Kimberly said, “I’d like to go over the rules that you all will be following. Rule 1, which we agreed to in the bet, is that you will do whatever we want for the next 3 hours. Rule 2: There will be no complaining, bargaining, or hesitation. If we tell you to do something, you do it. Rule 3 if you are going to cum you need to alert the room with enough time so that we can all gather around and enjoy the show. There will be a punishment if you disobey any of these rules. And, since you are a team, if any one of you violates a rule, you will all be punished. Your first offense will be a spanking. It’ll increase in level from there, but we’ll address that when or if necessary. This should not be a surprise to you. Do you agree with these rules?”

We all said, “Yes.”

“To get started, each of you is going to be paired with a host to help you, one of the three winners. Elena will be helping Eric, Lauren will be helping Nick, and I drew the short straw and will be helping you, Rich. We will start by undressing each of you individually. Elena will start first with Eric.”

The three of us were standing at the front of the room, facing the three tables and over 20 women. We were all in our boxers and undershirts. Elena stood up from her table and walked up to Eric with a big smile on her face. Elena said, “We’re going to have some fun, Eric. You’re a very attractive man with a lot of muscle. It seems a shame to hide them under clothing. Let me start by helping you take off your undershirt.”

Elena pulled Eric’s undershirt over his head, exposing his upper body. He was extremely muscular. Elena started rubbing her hands over his chest and arms and commenting, “Ooh, very nice, this is going to be fun. Let me see what you’ve got down below.” With that, she stretched his boxers away from his body so she could get a private look down inside. She turned back to the audience, saying, “Oh my god, you are going to really like this. I’ll keep you all in a bit more suspense, Eric, turn around so your back is to the room.” Elena knelt in front of Eric, pulled down his boxers, and had him step out. She threw the boxers to the side of the room and started to reach around him and rub his butt. This put her face up very close to his dick which was starting to get excited. The audience was getting very excited, but wanted to see the front. Someone yelled, “Turn him around!”

Elena said, “Your wish is my command.” She turned Eric around and exposed him to the room. He was huge. His penis was not erect at all, yet he was already over 6 inches. Elena gave him a few strokes, and he had just barely started to get erect and was already up to 8 inches and had more room to grow.

Kimberly took back control. “Well, that was a good start, but we have two more volunteers to see, so let’s not get too far along before we have the others catch up. Elena, don’t set that thing off just yet. Lauren, why don’t you come up and help Nick out of his underwear?”

Elena took Eric to the side of the room. She stood next to him and would occasionally touch his dick if it started to get soft while Lauren was assisting Nick, just to keep him in a state of semi-arousal.

Lauren repeated the same process with Nick in the same manner. First, she removed his undershirt and felt his chest, then took a peek in his boxers, and then repeated the rear view/front view exposure, finally exposing his dick to the crowd. Nick also has an impressive penis. Not quite as long as Eric’s, but his girth is tremendous. He looks like he has another appendage. Nick started at about 5 inches while flaccid, but quickly grew to 7 as she touched him, and would also get even larger when fully erect.

After finishing the Nick unveiling, Lauren took Nick over to the side of the room, and it was my turn.

Kimberly approached me with the largest grin I have ever seen. “Let’s go, Rich, time to see if the goods match the talk.”

She walked me to the center of the room, and all eyes were on me. She removed my undershirt and started to rub my chest. I’m in pretty good shape, not as good as Eric, but not bad. The room had been heated up and was waiting for the final unveiling. Just as the other ladies had done, she pulled my boxers away from my body to get a sneak peek below. She looked back up at me in the eye with an even bigger grin. She knew she had won. She turned me away from the audience and pulled down my boxers. Her face was right next to my dick as she rubbed my butt. The audience was liking the view from behind, but again someone shouted out, “let’s see the big man’s dick!” She turned me around to face the crowd and they could all see my 2-inch dick. It’ll reach 4.5″ when erect, but it is far smaller than what Eric and Nick had displayed. When I’m fully erect, I might grow to what the other guys were when flaccid. I was humiliated. Kimberly topped off my humiliation saying, “well I’m not sure where all his cockiness comes from.”

*****

“I think the next order of business is to let everyone in the room have a nice inspection of the goods. Why don’t the 3 of you line up in the center of the room and get yourselves nice and hard so everyone can get a good look at you in full glory.”

Eric, Nick, and I came to the middle and started to jerk our dicks. There was a lot of hooting and hollering from the crowd, along with encouragement to ‘get that thing hard’. Eric reached a full 10 inches; Nick was about 8 inches; and I was coming in at about 4.5 inches. After we were fully erect, Kimberly said, “We’re going to let the boss have the first view, and then we’ll have you spread out among the crowd. Why don’t you three line up in size order and then we’ll have your host present your dick to Dana.

Being the tallest, I stood in the back, with Nick in the front and Eric in the middle. Kimberly said, “No, no, not height order, size order. Get your dicks next to each other so we can see who is the biggest.”

Of course, Kimberly already knew who was biggest to smallest, it was just another dig to get at me. She said, “Rich in front, then Nick, and finally Eric with his monster in the back. Hmm, now that I think about it isn’t Dick often a nickname for Rich or Richard. I think from now on we’ll call you ‘Dick’.”

Kimberly stood next to me with Lauren behind her, next to Nick, and Elena next to Eric behind them. She led the way and walked us over to Dana, who was seated at the center of the front row of the first table. Kimberly said, “Dana, I’d like to present to you Dick’s dick.” This got a big laugh from everyone, including Dana.

Dana said, “I was sorry that you did not measure up this year — oh, I meant your sales in case you misunderstood. Now let me see what we have here.” With that she took hold of my dick and pulled me in close. She looked my dick up and down, rubbing her fingers all up and down the shaft and then exploring the head. She realized I was getting a bit excited and decided to stop touching my dick and started exploring my balls. She rolled each ball in her fingers and then decided that I had had enough. When she was through, she said, “Okay, you can let the other ladies at this one, let me see who is next.”

With that, Kimberly took me to Jennifer, my assistant, while Dana moved on to Nick and repeated her inspection with him. Jennifer is probably the best-looking woman in the company. She has huge boobs, a thin waist, a beautiful face, long blonde hair, and did I mention she has huge boobs. Jennifer looked me in the eye while grabbing my balls first. Jennifer said, “I hope you are enjoying your usual view down my blouse. I think from now on, whenever you take a look, I’ll grab hold of these and see how you like it.” She moved on to my dick, giving it a pull to get it harder, and then a slap. When Jennifer was through, Kimberly brought me around to the other ladies sitting at her table for each of them to explore my private parts.

Meanwhile, Dana had finished exploring Nick. Lauren took him over to her table to let the ladies there inspect him.

Eric was now presented to Dana. She said to him, “You are truly impressive. And in case there was any misunderstanding in your case, I’m talking about your body, not your sales.” Dana was very much enjoying Eric and spent a bit more time with him than she did with Nick or me. In addition to her thorough inspection of his dick and balls, she also had him turn around and spread his cheeks to inspect his anus. Then she felt his arms and torso. She finished her inspection by taking a quick suck on his dick before allowing him to move on. Elena was so thrilled that she had lucked into Eric as her partner. The girls knew Eric was muscular, but had no idea of his dick size. She took him by the dick and brought him over to her table for the people there to have their inspection.

Elena’s table was the one where Jerome was sitting. So, as he circled the table and each lady had their inspection eventually Elena brought Eric over to Jerome. Jerome was grinning, and the ladies at the table were very interested in seeing this. Jerome knew that there was a long night ahead of him, so he didn’t want to push too far too early. He followed the lead of the ladies at the table and fondled Eric’s dick and balls. Eric was trying to tune this out as he is not attracted to men and really did not want a man to be touching him. But he knew that if he complained, he would face punishment. After each of us was inspected at our host’s table, we were rotated through the other tables as well. This continued until each of us had been thoroughly inspected by all the ladies… and Jerome.

*****

Kimberly said, “I think we’re well warmed up. I think we need some cum to start flying around here. But I don’t want you all to explode at the same time. Let’s stage this out. I think we’ll start with Nick. Why don’t we have Nick come up front and center? We’ll have Lauren do the honors of jerking him off, and we can all gather around to watch the event. I think we should give our other entertainers a front row seat so they can see very well how this works. We’ll have Eric and Rich/Dick get down in front of Nick so that they can get an eyeful when he cums. I know guys love facials, now you’ll get to experience one yourself.”

I said, “there is no way I’m going to have Nick cum on my face.”

Both Eric and Nick immediately said, “No, don’t object.” But it was too late.

Kimberly said, “I knew you would be the first one to complain. As you agreed to the rules earlier, this will result in a punishment for all of you. Then we will come back and proceed as planned.

All 3 of you will now be spanked. Join your host at her table. She will put you over her lap and then the entire table will take turns spanking your butts.”

I accompanied Kimberly over to her chair and lay myself across her lap. My dick was hanging down between her legs and she clamped her legs together to hold me in place. The other two were having the same done to them at their host’s tables. Kimberly, Elena, and Lauren had done quite a bit of strategizing in planning and coordinating all the aspects of the evening’s events.

Once we were in place, the spanking began. Each host went first, demonstrating what she was doing while the other ladies at the table observed. Kimberly rubbed my butt cheeks to get them warmed up and then gave me several very hard swats on each cheek. After she was finished, she grabbed my balls and squeezed to make sure I knew she was in control. I thought I was done after she finished squeezing my balls and started to try to get up. She said, “Where do you think you’re going. I was the only one at the table; every lady at this table is going to get a turn.” I resumed the position, and Dana was the next one to go, followed by Jennifer, and then all the other ladies at the table. A total of eight ladies had swatted my butt and squeezed my balls. I was in significant pain. If further penalties were going to be harsher than this, I need to learn to keep my mouth shut.

“Okay, now where were we? Oh yes, Lauren was going to jerk Nick off onto Eric and Dick’s faces, unless there are any further objections?”. Kimberly looked at Eric and me, and we both kept our mouths shut. Probably good advice for this next activity too so we don’t get Nick’s cum in our mouths.

Nick moved back up front, and Eric and I positioned ourselves on the floor in front of him. I could see the other guys had bright red butt cheeks as we were moving into position. I certainly expect that mine looked the same. Once in position our faces were directly in front of Nick’s dick. Kimberly said, “If I were you, I would keep my face right where it is. If you move out of the way, that will require another penalty.”

While our spanking session caused our dicks to deflate, we were still extremely excited from being fondled by 24 women (okay 23 women and one man) for most of the last hour. I didn’t expect it would take too long until Nick covered our faces in jizz.

Lauren attempted to wrap her hand around Nick’s dick. It was so thick that she really couldn’t grasp all the way around it. She did the best she could and started to move her hand up and down his shaft. She made deliberate movements between pointing the tip at my face and Eric’s face which led to some side betting as to who was going to get the first stream of cum. There was a lot of encouragement from the crowd of ladies who were all gathered around us. “Go for it, Lauren!” “Stroke that dick!” “Splash their faces!” After many strokes she decided to vary up her technique and tease his dick a bit with light touches and she reached between his legs with her other hand and started playing with his balls. This had the desired effect, and Nick started to get very close. Lauren went back to full strokes while maintaining her grip on his balls. Nick shouted out, “I’m coming!” and then a few seconds later, he exploded on our faces. I was the winner (or loser) who got the first shot, but Lauren directed his dick back and forth so that we each got a face full as Nick shot stream after stream of cum.

Kimberly said, “Great job, Lauren! And, you too, Nick. Good thing you remembered to let us know you were going to cum in advance or you all might have been heading to another punishment.” Kimberly handed Eric and me some paper towels and wet wipes and told us to clean ourselves up.

*****

Kimberly continued, “You know I was thinking that these guys could use some cleaning up, beyond wiping the cum off their faces. They are a bit too hairy for my taste. I think we need to get them a trim, especially in the pubic area and around their anus. Fortunately, we have some skilled professionals with us today who have volunteered to assist us with this. You all met Jerome earlier. His colleague from the hairdresser is Belinda. Nick why don’t you take a short rest for a minute to recover while we start with Eric and Dick. Belinda, why don’t you start with Eric, while Jerome can work on Dick.

During the previous activity, a few of the audience members had placed mattresses on top of each of the tables. Elena took Eric to her table and had him lay face up on the mattress, and Kimberly did the same with me on her table. She then asked Belinda and Jerome to get started on our pubes and invited everyone else to gather around and watch.

The thought of someone wielding sharp items near my dick makes me very nervous. However, I did not plan to complain any further. I was also not thrilled that I drew Jerome instead of Belinda, who was quite attractive. But I’m sure that was intentional on Kimberly’s part. Jerome started with the outer part of my pubic area, basically shaving the entire area clean. He left a strip of hair, close cut, above my dick. It then came time to clean up the hair growing right next to my dick and my balls. He said, “I am going to need to get you hard to make it easier to shave this area and your balls. I hope you will enjoy this as much as I will.” He then started to stroke my dick. I closed my eyes and pretended it was Kimberly doing the stroking so I could get hard and get this over with. My dick became hard, but Jerome decided that he would continue stroking anyway. He was using the razor with one hand and had his thumb pushing up against the underside of the head of my dick to keep me aroused. I have to say, this guy really knew where to touch, but then he knew what it felt like, so he had an advantage.

To Jerome’s disappointment he finished my dick area and then asked me to turn over and get up on my knees with my ass raised. Jerome asked for some volunteers to help out here, he needed to spread my ass cheeks so he could get the hair in the crack. To my chagrin, Dana volunteered along with Jennifer. He had each of them pull my ass open so that he had access to the crack. They and everyone else had a great view of my anus. Jerome took some shaving lotion and rubbed it along the crack being sure to get quite a bit around the anus itself. Probably much more than necessary. He then began shaving away all the hair in the area. When he was done, he took his fingers with some aftershave lotion and wiped the entire area, being sure once again to pay special attention to my anus. He even stuck a finger in, he said, to make sure no hair had snuck inside. When I was finished, I stood up and saw that Eric had already been shaved, and Belinda was now working on Nick.

Kimberly said, “I think you both look much better. Dick without all the hair around it I think your dick looks like it might be another inch longer.

At this point I think you both need to cum. Nick already shot a load and is being worked on by Belinda. You’ve been fondled for a long time and are probably bursting at the seams. Now, how should we do this? Do you guys like blow jobs?”

I knew better than to answer. Kimberly was going to do what she wanted, no matter what we said.

She continued, “No answer, hmm, maybe you don’t. But I think we should do a blow job anyway. How about another game? This one is a 50/50 chance. We will flip a coin, and you can call it ‘heads’ or ‘tails’. If you win, one of the ladies will give you a blowjob. I’m sure several would be willing. However, if you lose, then you have to blow each other. How does that sound?”

Again, not planning to answer. I would have preferred better odds, but at least there was a chance I wouldn’t have to blow Eric.

She continued, “Okay, I will flip the coin when you are ready, and you can call it in the air.”

I said, “Okay since we’re talking about a blowjob, we call ‘heads'”

Kimberly said, “Ha, ha, very funny. I liked that. Well, let’s see the result.” She opened the hand she had over the coin, and it was heads. I was so relieved.

“Very good, guys, you got lucky. Let me check with the women and see who would like to do the honors.”

Kimberly stepped over to the ladies, and they discussed this for a few minutes before she turned back to us. “You guys are very lucky. We had several women who wanted to blow each of you. For your entertainment, we will present each of you individually, allowing everyone to enjoy the show. Eric, we actually had to limit the number who wanted to suck your dick, but we decided that the three women from the development organization could all share your meat.”

Eric was thrilled; these girls were really nice-looking.

Eric moved to the center of the room, and the three girls approached him. I was wrong when I said they were nice-looking; they were drop-dead gorgeous. How did I not remember their names? They were also very turned on and decided to really get into it. They laid Eric down and two of them started sucking on both sides of his shaft, moving in sync up and down. The third girl opened her shirt and took off her bra and started pushing her tits into Eric’s mouth. The three of them moved around his dick like they had practiced ‘synchronized blow jobs’ together. Hmm, maybe an idea for a new Olympic sport, but I digress. About every 30 seconds or so they would rotate so that they each got to suck him and they each got their tits sucked by him. He held out longer than I could have. After about 7 or 8 minutes, he finally shouted out, “I’m coming!” The girls had been told not to take his shot in their mouths because everyone wanted to see it. So, they removed his dick from their lips and started to jerk him off. His dick is so big that actually all three of them had a hand on it when he started shooting load after load up into the air. Most of the shots fell back on his body, but I think the first one may have landed on his face. His second facial for the day.

“That was great. Now Dick, you also had multiple ladies volunteer. You will have two women sharing your morsel. They are the ladies from the cleaning and maintenance organization.”

I’m sure these are very nice ladies, but they are older and not nearly as attractive as the girls who just blew Eric. Still, I was very thankful that it was they blowing me and not Eric.

Kimberly continued, “Oh, and Jennifer also said she wanted to be involved.”

All of a sudden, things were looking up. Getting blown by Jennifer has been one of my dreams.

“Jennifer said she would like you to eat her ass.”

Ugh, not what I had in mind.

I lay down, and Jennifer approached me and stood over my head. She removed her panties which gave me a good look at her pussy and her anus. She lowered herself down and shoved her anus near my mouth and said, “start licking”.

The cleaning ladies tried to simulate what they had just seen done to Eric, but it didn’t quite work out the same. They first tried to do the synchronized blowjob on my shaft, but I was just too small for that to work. So, they gave up on that fairly quickly and decided to rotate back and forth with one of them blowing me while the other one had me fondling her tits. My mouth was too busy on Jennifer’s anus to suck their tits, which might have been a blessing. I really don’t want to be complaining about fondling tits, but these lady’s tits were old and saggy. They rotated back and forth several times, and it took me over 10 minutes. I was excited about getting a blow job, but not that much by who was doing it. Finally, I started to breath really heavy and moan so they knew I was getting close. They took my dick out of their mouths and started using their hands. Or should I say, they used their thumb and forefinger to jerk me to completion. I shot my load into the air, and it also landed all over my body. The crowd watching was thrilled with both Eric’s and my performance.

Kimberly came over to us and said, “I hope you enjoyed that because unfortunately, you just violated one of the rules again. You did not announce that you were coming.”

*****

“Guys, you’re in the home stretch. If you can get through this penalty without any complaining, we’ll consider your bet loss paid off.

We’re going to do this penalty, focusing primarily on one of you at a time while you satisfy your host, although all three of you’ll participate each time, as I’ll explain. We’ve moved the mattress to the floor because we’ll need more room around it. There are two major parts to this penalty. Your host will be your focus for the penalty. Each host will be naked and lie on the mattress. The man she is hosting will get on his knees between her legs and give her head until she is satisfied. The other two men will suck on her tits to increase her enjoyment. While you are pleasuring your host, one of the other ladies will reach underneath you and stroke your dick. You are welcome to cum if you can and you do not need to announce it because your mouth is going to be busy in your host’s pussy. Any questions so far?”

I said, “Not a question, but this sounds great.”

Kimberly continued, “I’m glad you like it. There is one more part that I have not yet mentioned. While you are on your knees you will be fucked in the ass. We have several strap-ons available and one of us will lube you up and then give you a nice fuck.

Elena, would you like to be the first?”

Elena removed her clothing and took her position on the mattress. All three of these ladies were beautiful, each in their way. Elena had a very pretty face with long, black hair that hung just below shoulder length. She was fairly short, very thin, and had very perky A cup tits. Elena spread her legs, and Eric took his position on his knees. Nick and I were guided over to our positions where we were going to suck on her tits. Dana had asked to be involved in these punishments and she really wanted another chance at Eric’s dick, so she took the role of reaching under him. Eric began licking, we began sucking, and Dana began stroking.

The final position was Lauren’s. She stripped naked as well, since she was going to be doing the honor position next anyway. She picked out one of the strap-ons, a fairly long one, to try to match Eric, and fastened it around her pelvis. She grabbed the lube and got behind Eric and greased his anus. She really didn’t want to hurt him, so she tried to insert the strap-on gently and slowly. He was scrunching his anus so this was difficult. Lauren told him to relax and let her in; it was going to happen one way or the other, and it would be easier if he cooperated. Eric realized she was right and tried to relax, letting it happen. Lauren got the strap-on in and started to pump his ass. First slowly and then faster.

Dana had Eric’s dick at full length. She realized that she had enough room underneath him to get under there herself. So, she lay down on the mattress and moved her head underneath him. She took his dick into her mouth and started to suck him off.

The sexual stimulation was intense. We were sucking Elena’s tits while Eric was eating her pussy. Eric was being sucked by Dana while Lauren was fucking him in the ass. Elena lifted off the ground with a tremendous orgasm. This set off a chain reaction with Eric shooting his load into Dana’s mouth.

Lauren stopped pumping and said, “My turn”. She quickly took Elena’s position on her back on the mattress. Lauren is a gorgeous redhead. Long wavy hair, freckled face, a dream. She has very large tits, probably a D cup, while still being thin and in great shape. I stayed where I was to suck Lauren’s tit and Eric joined me on the other side. Nick moved between Lauren’s legs. Elena needed a break after her orgasm, so she was out this round. So was Dana. Belinda, the hair dresser, volunteered to perform Dana’s role on Nick’s dick. This time, she just went straight underneath for the blow job from the start. Kimberly stripped down and took one of the strap-ons for the final position.

Lauren was already really hot from fucking Eric, so this was going to be very quick. We all got started with our assigned tasks, and it was probably under 2 minutes before Lauren had an orgasm. But she said she wasn’t done — keep going. So, Nick kept licking and Belinda and the two of us kept sucking, and Kimberly kept fucking Nick’s ass until Lauren had her second and third orgasm. Nick shot his load at about Lauren’s second orgasm, but Belinda took it all and kept going.

The last one was Kimberly. Despite my competitive dislike of Kimberly, I must admit that she is beautiful. She has a gorgeous face with short blonde hair (done very nicely by Belinda), She has a perfect body; thin waist, nice ass, and perfectly formed C cup tits. She lay down on the mattress, and I took my position between her legs. Eric and Nick would be sucking her tits. Elena had recovered and would be underneath me sucking my dick, while Dana and Jennifer were fighting it out for who was going to fuck my ass. They finally agreed to take turns.

We began our sucking and licking activities and Dana and Jennifer each had taken a turn fucking my ass. I was feeling pretty good licking Kimberly, having my dick sucked by Elena, and even though I had never done it before, it felt good having my ass fucked by Dana and Jennifer. Then the feeling behind me changed. There was something in my ass, but it did not feel like before when Dana and Jennifer were fucking me. It actually felt… better. I had to see what was going on, so I did a quick turn of my head to look behind me. It was Jerome. He had stripped down and it was his dick in my ass.

The crowd was going wild. I was shocked, and my immediate thought was to get him out of me. But I realized that if I objected, we were going to get another punishment and he was going to fuck me anyway. More than likely, I’d be sucking Jerome’s dick and then he would fuck me anyway. I figured I’d better just deal with it. Besides, it really did feel good.

I got my mind back on my business and restarted giving head to Kimberly. I had my fingers in her pussy and my mouth on her clit. She was climaxing multiple times and then I shot my load into Elena’s mouth and Jerome shot his load into my ass.

Kimberly caught her breath and then said, “Great job, Rich. I knew you would be good for something.”

Kimberly pulled herself together and thanked everyone for participating. They were all thanking Lauren and Elena for including them. She called an end to the evening and thanked the three of us for being everyone’s entertainment.

I turned and said, “We’ll get even with them next year.”

Eric and Nick said, “What are you crazy, no more bets!”

*****

It was over, and I was sitting in my office just staring off into nothing. I heard several of the ladies gathering their things and laughing. They were all going out for drinks. Almost everyone was gone, and I was thinking back on the day, wondering what a loser I had become. I was stripped in front of my boss, my secretary, and 20 other women. I got spanked and a cum facial, and worst of all I got fucked in the ass by a guy. These women are going to see me every day and I’ll know that they all saw my small dick.

Then there was a knock on my door. It was Kimberly. I said, “Coming by for one last gloat before you leave?”

She said, “Quite the opposite. I wanted to compliment you. You made a bet, lost, and you paid up. Many people would not have done what we had you do, and I think you handled it well.”

“Well, thank you for that. But I’ll never live this down. Everyone is going to be calling me ‘Dick’ and I will be laughed at because of my small size. I’m not sure where to go from here.”

“I like your dick. Your mouth was pretty good, too. So, I’d like to make this up to you. How about I take you home and we fuck like crazy for the weekend?”

I wanted to let you know that no reply was required.

 

The End.

 

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