Assassins MC Pt. 13

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Penny In Trouble.
10.8k words
4.73
7.7k
4

Part 13 of the 20 part series

Updated 06/10/2023
Created 12/14/2020
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This is a work of fiction. Unless otherwise showed, all the names, characters, businesses, places, events, and incidents in this story are the product of the author's imagination or used fictitiously. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Part 13 Penny in Trouble

Susan came by to see everyone, but I suspect she was most interested in seeing her daughter. She was over so much I commented she should move in and start dressing the same as the other women. She laughed and said she wasn't against either the moving in or the outfits. I asked about Ben all the time. Susan and Roger put him into a program for anger management, and Roger was spending more time with him, trying to get him turned around and able to see what he did was wrong. Susan assured me Ben would come around, and I hoped she was right.

Susan arranged for Julie to start her ghost training. She went after school to train in martial arts and handheld weapons. She was excited and looked forward to going each day. Susan told me she was making extraordinary progress, and Julie showed her enthusiasm when she told me about what she learned. I never previously saw her as interested in anything else as she was about this.

Roger and I started working together more. I spent more time with him after school and on weekends learning about different aspects of the club. I helped with more pickups, and they never got easier. It was just another woman that lost the life she knew with no hope of gaining it back. As a side effect of us spending time together, Roger was over at my place often. At first, this was uncomfortable for Penny. She wasn't ready to forgive her father, but she kept it in and remained cordial. Penny eventually softened, graduating to hugging her father when she saw him.

Roger and I had a standing agreement to share the women. Nicole, Beth, and Julie knew Roger, and he was over so often that they enjoyed having sex when he requested it. He would return the favor to me, and Susan was more than happy to accept the deal. I still had to ensure the women were accustomed to the lifestyle, even if I didn't fully agree with it. If Roger was in the house, he made it a point to only have sex in private so Penny wouldn't accidentally stumble in, and I did the same with Susan.

Christmas was fast approaching, and we were making our plans for the big Assassins Christmas party. We had to come up with some sexy outfits for the women. One competition was to see which family had the best costumes. One evening Roger and Susan came over for dinner, but Ben stayed home, still not ready to face us all.

We discussed the upcoming party, and I came up with the idea that we combine resources and dress all the women, including Susan, in the same outfits, since we were "technically" family. Everyone liked that idea and we all brainstormed with Nicole, the one who came up with dressing like sexy Mrs. Claus. The women could all wear red corsets with their black high-heeled boots, get some red collars, and each wear a Santa hat. The women would normally have their guardian name on their costume, but with me and Roger combined, we had to come up with a name that suited both of us. Whiskey is Roger's club name, and I suggested a name from whiskey distilling, Devil's Cut. That's the whiskey that gets trapped by the wood when it ages and is extracted later. It plays off my biker name Diablo, and we all agreed. Dressing in red would go right along with that.

The women went out the next day and each bought a red corset and red collar. Unlike the ones they currently wore, the corsets were not exposed top and bottom. These corsets, however, unzipped in case the women needed access, which we knew they would. Their breasts were covered up, but the amount of cleavage bordered on obscene. Susan had to buy a pair of thigh-high boots, which looked great on her.

When the night of the party arrived, we all drove out to the clubhouse, my women with me and Roger and Susan in their truck. We all walked in together and the women looked outstanding. Led by me and Roger, the women together looked like a BDSM Christmas review. They all looked sexy as hell, and they knew it; they strutted in like peacocks.

The place was crowded. All the men were club members and the women all belonged to the men. There were only affiliated women in attendance, so I suppose John had to get rid of all his entertainment, at least for the night. Not all the members were in attendance, though. We had a handful taking care of business in different states. There were also some of the associated women missing, having to work, or also out of state. I would estimate around 200 people. The clubhouse was huge, and people were spread out all around the building.

The place was filled with people and it was loud. Music was playing, and the playlist comprised Christmas songs, classic rock, and country. Some people were in one room dancing, but the majority were snacking on the food and talking.

Roger told the women to mingle. Beth and Susan grabbed Penny, Julie, and Nicole and showed them around, introducing them to some of the other women. Roger took me, we found John and said our hellos. He was happy to see us and wanted to know where our women were. We pointed them out and his mouth fell open. He told us he would have to consider dressing his entertainment women in a similar style. Roger pulled me around, introducing me to far too many club members for me to remember, and at every stop, I heard more stories of my father. He touched many people and affected almost everyone he met, and I just hoped I was half as well-liked as he was.

The first contest was starting. It was a fashion show, with the women showing off their costumes and the men voting with their applause. It was not scientific, but they whittled it down to 5 women at the end. Penny and Julie were both selected and were up against 3 other women that were just as hot as they were. When the MC passed his hand over a woman's head, everyone would cheer. Penny and Julie were last in line.

The first woman, a blonde with large breasts, at least a DD cup, pulled her top up and flashed her tits. The audience applauded. The second woman, another blonde, also a DD cup, did the same, but pulled her breast up and licked it, followed by louder applause. The third woman, a brunette with smaller breasts, had to do something better. She pulled her dress over her head and flashed everyone in attendance. She felt herself up, turned around, and shook her ass. The audience roared their approval.

Penny was next. When the announcer passed his hand over Penny, she turned to Julie, grabbed Julie's hair, and pulled her into her. She planted a big kiss and reached between her legs, pretending to grab her pussy. The audience lost their minds. Every man in the place was hooting and hollering.

When it was Julie's turn, she pushed Penny down, pulled Penny's head between Julie's legs, then put her hand on her head. She grabbed her hair and mimicked a motion of making Penny suck her off. People went nuts, and it took a few minutes to calm everyone down. Needless to say, Julie won the $5000 that was up for grabs, and she split it with Penny.

The second contest was the big one. In this, each family would send their women out to please as many men as they could. Each club member found a seat somewhere, some on the first floor, some on the second. They spread all the men out throughout the building, and the women would come around and do whatever they could to get the men off. Each man had 5 white chips and a marker. He would take those chips and write his favorites down and drop them in a bucket. These would be counted and the family with the most votes would win.

To make it fair, the number of their women divided each family's score taking part. So, 5 would divide our score. This was so a single woman representing her guardian had just as much chance of winning as a family of 10 women. Those 10 women would have to get more than 10x the chips as that single woman to win. Oh, and we couldn't vote for our women. That made sense.

The contest only ran for 2 hours. The women had to hustle. To reach every man, they wouldn't have enough time to do much, so they had to choose wisely and make each count. If they spent too much time, they risked not getting enough votes. They didn't have to get each man to orgasm, just to leave a lasting impression to secure their votes. Beth and Susan came prepared; they reached in their purse and gave Nicole, Julie, and Penny a bottle of lube; they would need it. There was a blue barrel filled with condoms. There must have been thousands of condoms, and the women all grabbed as many as they could carry. The game began, and I sat back, not knowing what to expect.

The first woman who came over didn't say a word. She just pulled her shirt over her head and got down on her knees. She was about 5'10 in height, brunette hair, and had to be about 50. She was still in good shape, and her breasts were a D cup. She pulled my dick out, put it in her mouth, and started swirling her tongue around it. The entire time she was looking in my eyes to see if I approved. After a minute of doing this, she pushed her breasts in my face and started jerking me off. She was trying her hardest to get me to cum, but couldn't do it. After another minute, she kissed me and went to find someone else. I took a note of her name, but I was sure someone better would come along. Sure enough, she did.

The next woman came by almost immediately. She was a redhead, standing about 5'5, and had average-sized breasts, around age 35. She sat in my lap and started kissing me. She wore perfume that reminded me of pine trees; it was nice. My cock was still out from the previous woman, and she wasted no time getting me hard. She had her bottle of lube, put on the condom, applied some to me, climbed on top, and started fucking me. It amazed me at how tight she was. She had freckles all over her body, and on her, they looked sexy.

She kept kissing me while she rode me, and between that and her tight vagina, I told her I was about to cum. She pulled out, put her mouth around my dick, and sucked every drop. In front of her, I wrote her name on one chip. She clapped and skipped off to the next man. This went on for the next 2 hours. I must have had over 30 women try their luck in various ways. I only came 4 times in two hours. I say only, but 4 times is quite a night. By the end, I was exhausted, and I was sure my dick had friction burns; I could barely touch it. Next year I'll bring my lube.

During those two hours, I caught a few glimpses of my women. The first was Julie. She jumped in a 30 something-year-old club member's lap and stroked his dick. He was good looking, clean-cut, and kept himself up. Not what I could have considered a typical biker. She would kiss him, then get down and try to suck him off. I saw her wipe her mouth, so I assumed she was successful.

The next was Nicole. She went down on her knees between the legs of a 50 plus-year-old man. His face was weathered, but he was muscular and looked fit. She continued until his dick was hard, turned around, then mounted reverse cowgirl. She rode him like that until I saw him relax, knowing she had gotten him off. She turned around, gave him a big kiss, then ran off to look for another man. Nicole was initially hesitant, but as the competition went on, she appeared more into it, becoming quite frenzied. I knew they forced her to have sex previously with multiple men, so it was surprising to see her this enthusiastic.

Next, I saw Penny. She approached a man in his 40s. He had a beer belly, beard, and looked like he lived on his bike. She bent down, kissing him and rubbing his cock. She pulled back and got down on her knees and sucked him off, put on a condom, then climbed up and sat on his lap, facing him. She pushed her breasts in his face while she fucked him. After trying unsuccessfully for a minute to get him to cum, she bent down and whispered in his ear. He tensed up and came in less than 10 seconds. Later when I asked what she said, she told him she was a teenager; I suppose eighteen counts. That did the trick! She said that worked at least 10 times. To think Penny was a virgin just a few weeks prior, then tonight get 10 shots. Simply crazy. Thankfully, she is on the pill.

If anyone was ready for this, it was Penny. She was a sex fiend since she lost her virginity. As I mentioned previously, she was tiring me and Julie out. This contest was perfect for her. In fact, it probably wasn't enough. She was up ready to go again the next day. It would take some time until she calmed down and only had sex once or twice a day, at least that I knew of. For the record, it knocked me out of commission for two days after this.

It disappointed me I didn't see Beth and Susan from where I was sitting, but I was sure I would get their stories later tonight. All the men were spent, and we grabbed some drinks and sat around talking while they counted the votes. The women all cleaned themselves up, grabbed some food and drinks, and mingled with the other ladies in attendance. They all came up and hugged me, telling me they were having a great time. I was worried Nicole, Julie, and Penny wouldn't like it because of the big contest, having sex with so many men, but they said that wasn't a problem. After the first few men, they didn't see them as men, but props they used in trying to win the contest.

I suppose that made sense, and mirrored the Assassins habit of seeing women as less than human; not to that extent, however. This was just a small microcosm of how easy it can be to dehumanize someone in pursuing a goal. I'm not comparing the women temporarily distancing themselves from the men to the systemic abuse heaped on by the club, but it's interesting to see how quickly the mind can rationalize that.

I heard multiple stories of my father and his exploits with women. It seemed even after marrying Beth, he didn't slow down. He would always come home to her, but his womanizing never slowed. I wondered if Beth knew the sheer number of women he was with. She must have at least had an idea, and it wasn't like these men were hiding it. I had sex with around 30 women tonight. This was different, though. I had sex out in the open in front of everyone, and there were no secrets. My father would do it away from Beth. Would the club's lifestyle force me to become just like my father? I wondered just how much of that was him, and how much of it was the club.

With the votes counted, our women won by a large margin, even with the votes divided by 5. The women were ecstatic. All the club members came by and congratulated me and Roger, telling us how lucky we were, and the women received many accolades from the men and the women. Oh, we knew exactly how lucky we were; we lived it every day. Each woman won a $10,000 shopping spree, a luxury day at a local spa, a gold and diamond necklace with a pendant with the club's logo, a gold watch, and a diamond tennis bracelet. The second and third place teams each won a combination of the above prizes, and each woman in attendance left with a few of the items.

We stayed longer socializing, drinking, and telling stories. Well, I didn't have many stories to tell, just the one of our first night out dancing. People seemed to like that story and I repeated it around 35 times, and I was sure I would get many more stories in the coming years. At the end of the night, we were all worn out, said our goodbyes, and all drove home.

Everyone had a wonderful Christmas a few days later, spending time together with Roger and Susan. Ben even showed his face, acting remorseful to everyone, especially Penny. He apologized profusely to her and told her he still loved her and hoped she would forgive him. She told him she didn't hate him, but it would take some time to get past everything, and that was as far as she would go. Ben accepted, and we all enjoyed each other's company. With Ben there, we didn't partake in any sexual activities for obvious reasons, and the women dressed casually.

Christmas morning everyone wore casual clothes, mostly sweats and robes, when we opened our gifts. I received a gift or two from each woman, and they exchanged gifts between themselves. When they unwrapped their gift from me, each woman looked disappointed I only bought them one each. I told them I had a bigger surprise and to follow me. Over the holiday I had the construction company finish the basement plans I designed. I walked the ladies to the basement door. I had put a bow on it earlier when the women weren't looking, and I told them this was the second part of their Christmas present. Nicole joked a door was exactly what she was hoping for. Thanks, Nicole. They opened the door and walked down the stairs.

The basement ran the length and width of the house, and I had it divided into two rooms. The larger room opened as you walked down the stairs, and was designed as a gym. I lined the walls with mirrors. On one side of the room had aerobic equipment: a treadmill, rowing machine, elliptical, and stair stepper. On the second side was located free weights and a universal. On the back wall where a door was located housed what I called the combat area; this was for Julie, but others would soon be involved. It comprised practice dummies, different equipment including asps, wands, knives, gloves, punching bags, etc. In one corner, I set up a beverage station with a couple of mixers and blenders. It had a refrigerator that was stocked with drinks, both sport and energy, as well as fruits and vegetables for any juices the women liked. A large cabinet next to the station had various powders and mixes.

The women went crazy, each one giddy with excitement. They were trying all the equipment, and Julie was examining her combat training area, just grinning from ear to ear. After they played around for about 10 minutes, breaking off to come over and kiss and hug me, I told them there was one other room. They all stopped and looked at the closed door along the back wall. I had painted it black with a pink neon heart in the center. They hadn't noticed it in all the excitement.

The first one through was Nicole, and all she could say was, "What the hell!"

Behind the door was a sexual fantasy land. In the middle of the room was an oversized circular bed with pillows piled on top. Along three walls were shelves. One wall's shelves were filled with various sex toys: vibrators, dildos, pocket pussies, anal beads and plugs, feathers, etc. I bought everything I could think of, in various sizes and colors. On the second wall, the shelves held various bondage gear; blindfolds, restraints, paddles, whips, leather gear, etc. On the third wall, I had mounted some restraint systems. I had a large X with wrist and ankle restraints, a chain dropping from the ceiling for securing someone's hands above their heads, a set of stocks, and a spanking bench. In the back corner was a refrigerator loaded with drinks and snacks, and a shelf with various other foods. One had to keep their strength up if they spent considerable time in this room, and the room was covered in shag carpet, wall to wall.

I reached over and hit one switch and on came the lights. A mirrored ball in the center reflected the lights around the room and I had more mounted in the corners that rotated, spinning colored lights that reflected off the walls. Nicole and Beth just stood there and started laughing.

Beth spoke up. "Damn, Rich! Did you travel back in time and steal this room from the 1970s?"

The other two women were just looking around, not sure what Beth's reference meant. I looked around and realized she was right. I hadn't thought about it, but I must have seen something like this in an old movie or something. I joined in, and we all laughed.