Ginny's Dilemma

Robert added, "well, she knows what could happen."

Ginny asked Robert how he felt about it. "Not great, but Michelle said if that happens, it happens."

Ginny saw her parents sitting with some people and went over to say hello. Ginny's mother, Carol, saw her and had a big smile on her face when she came over. She hugged both her parents and her mother said, " I almost didn't recognize you with your clothes on. Ginny, are you going to enter the race?"

"Yes, wouldn't miss it."

"Me too," Carol said.

Don, Ginny's father got up and said that he was going to say hi to Mike.

"Any new adventures, Ginny."

"Oh, one or two. Do you know Connie?"

"Yes and all her staff. Lester was my first black cock. Absolutely love the man. Hope he's still there."

"Lester is still there. Yeah, my first one, too. So, is dad going to be your driver?"

"He had a funny look on his face when I asked him. But I guess so. Listen, I have to go to the lady's room. I'll call you during the week."

They hugged and Ginny felt a tap on the shoulder.

"Ms. Bossert. I didn't see you."

"Ginny, how about calling me Kathy outside the office?"

Ginny smiled and Kathy put her arm in Ginny's and they strolled to the bar. Kathy asked her if she was going to enter the race and smiled when Ginny said she was.

"Are going to enter, umm as a driver, I mean?"

Kathy laughed and said, "Well, if I could find someone to trust where I had a chance to win, I would...as a pony!"

Ginny choked on her drink. "What? You? A sub! I don't believe it!"

"I switch, Ginny. Sometimes I like to fuck people and there are times when I like people to fuck me."

"That's all fine, really, but if you lose its three hours in basic sex slavery."

"Yes, I know. Isn't that exciting! Got to run."

She kissed Ginny on the cheek and walked away. When Ginny returned to her friends, she saw her father leaving and shaking Mike's hand. She waived at her father and he blew her a kiss.

"So, when is Michelle's initiation?" Ginny asked.

"Four weeks. We still have to decide how to present her. Obviously, she will be naked but beyond that, haven't decided."

Everybody agreed that there was time but a collar, leash and maybe clamps and a butt plug or nipple clips would work. Jonathan and Grace had to leave so everyone decided to call it a night and they went home.

Ginny and Mike didn't talk much about the race. Michelle's initiation was on her mind and Mike had to attend a conference for a week and was faced with administering mid term exams. Ginny for her part, was busy at work and was able to talk to Kathy just one time after work.

"So, are you going to enter?" Ginny asked.

"Yes, I think I am. Found someone to drive. Should be interesting." Ginny smiled and asked if she was going to the initiation meeting.

"Trying to go. Will see."

Ginny and Mike were upstairs getting dressed the night of Michelle's initiation into the club. Ginny was trying to decide on what to wear. Mike never had expressed a preference preferring Ginny to be naked.

Knowing that after the initiation there would be opportunity for some wild sex or BDSM play, Mike finally said to Ginny, "Go naked. You know I love you that way and we're driving Jonathan and Grace to the hall so it won't matter to them and you will probably be naked right after the initiation anyway."

"Great idea," said Ginny. She put on a pair of heels and said "Ready. Let's go get our girl initiated."

They picked up Jonathan and Grace and Grace joined Ginny in the back seat.

"Oh, I should have gone naked, too."

"I'm not stopping you." Jonathan said from the front seat. "Go ahead and strip off."

Grace began to get out of her clothes and when they arrived at the club, she was naked.

"Lot of cars," Mike said.

As the four went inside the hall, they could see quite a few people already seated around tables. Bondage equipment had been set up around the large dance floor area, stocks, a suspension frame where a submissive could be bound spread eagle in an upright position, and a spanking bench. A large mattress and various padded mats were scattered around the floor. Before they went to look for a table, they each had to write their name down on a slip of paper and place their slip in one of two fishbowls; one marked male the other female. They found a table and sat down. Robert and Ellen, Michelle's parents, joined them.

"Where's our girl?" Ginny asked Ellen.

"Getting her makeup on. She's a bit nervous but really excited."

"Who's going to emcee?" Mike asked.

"Surprise!" said Jonathan. "I've known for a week but had to keep it secret so the spontaneity factor wouldn't be lost. Robert, Ellen and I worked out the details and any more than that, you will have to wait and see. Sorry, got to dash. Need to start in five minutes."

Jonathan kissed Grace and he left with Ellen and Robert.

A few minutes later Jonathan walked out with a microphone and spoke to the audience which Mike thought was close to 60 people.

"Good evening. In a few moments will begin the process of initiating a new member. She is the daughter of two of our founding members and will be presented by both of them. We do have other parents and adult children members so no, that is not a first for us. After the initiation you will have until midnight to enter our Day at the Races event. Forms will be distributed later. So, let me now introduce to you Robert and Ellen and their daughter Michelle."

There was applause as Robert and Ellen led Michelle out. She had her nipples clipped and the clips were connected by a small chain. There were large bulldog clips on each of her pussy lips. She was wearing a thick leather collar with a leash that Robert held. Ginny noticed that Michelle was walking almost normally but not quite. When the trio reached Jonathan, they had Michelle turn around and bend at the waist. Ginny and all the others saw that Michelle had a butt plug in her ass.

Jonathan spoke, "Well, as you can see, our initiate is a submissive and I can personally vouch that Michelle is truly a wonderful sub. In agreement with Ellen and Robert, and, of course, Michelle, we have set three tasks for Michelle to complete. For the next 30 minutes, Michelle is going to circulate among you and introduce herself. Ask her what you wish because you will then write down what you want Michelle to do. We will take those papers and draw them randomly. Michelle will then complete the task on the paper."

Michelle was unleashed and the pussy clips removed by Ellen. The nipple clips and butt plug were removed by Robert and she made her way to the first table. She didn't make it to Ginny's table until there were just a few moments left. Ginny put her arm around Michelle's ass and asked how she was doing.

"I am fine. A lot of people wanted to know if I've been fucked by my dad or eaten my mom. God, I think that's what they all want to see. Well, if it happens it happens."

Michelle said she hoped to speak to them later and went back toward Jonathan. Robert and Ellen just looked nervous.

"We are ready to begin, so write on the paper you have at your table and we will collect them," Jonathan instructed. "If you do not give Michelle the choice, then the people who will be taking part in the three scenes will be drawn from the appropriate male or female bowl. You cannot write a scene that says we want to see Michelle have sex with blank. Ok? Great! Start writing those scenes."

The scenes were collected, put in a bag, shaken, and Jonathan pulled out the first slip and read out loud, "Michelle will chose one female and eat her pussy. Right then. Michelle whose pussy are you going to eat until they cum?"

"That's easy! Ginny," she yelled.

Ginny got up and went toward Michelle and Jonathan who ushered them to the large mattress on the floor. Ginny laid down, lifted her knees up so that her feet were flat on the floor. Then, as if to invite Michelle in, she slowly opened her knees revealing her pussy. Michelle lowered herself between Ginny's thighs and in one long lick went from the bottom of Ginny's slit to her swelling clit. Some of the club members came alongside the mattress to watch Michelle's oral skills. Michelle was sucking and licking on Ginny and her face was quickly be covered in Ginny's juices. Low, guttural moans escaped from Ginny's lips as Michelle kept licking Ginny; pushing her tongue inside her friend as far as it would go. Ginny grasped Michelle's head with her thighs and her yelling told the audience she was cumming.

"Well done, Michelle. I am sure Ginny would say that you passed the first test of your initiation," Jonathan said. There was applause for her efforts.

Michelle was helped to her feet by a man she didn't know and Jonathan helped up Ginny. As he always does when Ginny is naked, he squeezed her ass.

"Now, the second scene," Jonathan announced, and he reached into the bag and pulled out a slip of paper. He read out loud, "pick four names from the bowls, two men, two women, who will each give Michelle twenty five strokes with four different implements that Michelle will choose She will be in the stocks for all the strokes."

The stocks were being moved into place and Ginny could see that Michelle looked a little concerned. One hundred strokes, Ginny thought. A number of implements were laid out on a table and Jonathan instructed Michelle to go and pick the items to be used on her. She quickly selected the flexible paddle, the riding crop, a sorority paddle and a tawse.

The fishbowls with the names were brought out and Jonathan pulled out two names from the male bowl. "Calvin and Don." Ginny didn't know Calvin, but Don was her father. The two men walked toward Michelle and hugged her. Jonathan drew out two names from the female bowl, "Connie and Ellen."

Ginny looked around the room because she hadn't seen Connie but there she was. Ellen got up from the table and said, "this I can do."

All four chastisers were dressed as they stood next to the naked Michelle just before two other men led her to the stocks. They had her head and hands immobilized in seconds. Each man took hold of Michelle's ankles and pulled her legs apart and attaching her ankles to cuffs at the foot of the stocks.

The four were discussing what implement they were going to use. They broke their huddle and Calvin was first. He held the tawse in his hand and gave Michelle 10 quick strokes, five on each cheek. He let the effect sink in and then he repeated the process. Michelle was squirming. Her ass was getting red and the way she was moving her ass was having an effect on the males watching what was taking place. Calvin finished with five sharp slaps across Michelle's cheeks.

Connie was next and she had the flexible paddle, which Ginny knew from experience, thought Michelle could handle. But after being hit with the tawse, she wasn't sure. Connie wasted no time. She alternated between Michelle's cheeks in rapid fire. By the end of the 25, Michelle was very loud in her yells.

Don had the crop. Ginny thought to herself, "hit her pussy, hit her pussy" hoping that would give Michelle's ass a break before the sorority paddle that Michelle's mother would wield. As if reading his daughter's mind, Don began his punishment of Michelle by bringing the crop upward into her pussy. He stopped after 10 strokes and moved in front of the stocks. Michelle's tits now felt the crop across her tits and directly on her nipples. They weren't easy strokes and Ginny was impressed by her fathers crop work. Well, maybe she thought.

Ellen was last and she picked up the sorority paddle and went to work on Michelle's red ass. The crack of the paddle against Michelle's ass echoed through the room. By the fifteenth stroke, Michelle had tears rolling down her face as the paddle did its work. But it was over. Michelle's ass was dark red, and Michelle was swaying her ass side to side. Don and Calvin undid the top part of the stocks and lifted Michelle up as Ellen and Connie uncuffed her ankles. Walking very slowly she moved toward Jonathan and the last scene.

"Do you need a moment or two, Michelle?" Jonathan asked her.

"No, no, I'm ok. Hope there's no spanking in the last one."

"Let's see, then." Jonathan said as he reached into the bag. "Michelle you get your wish. No spanking. Pick three names out of the male fishbowl who will then fuck your in your mouth, pussy and ass at the same time. Michelle chooses who goes in what hole. Well, this should be something!"

Michelle reached into the bag and pulled out a name and handed it to Jonathan, then a second and finally a third.

Jonathan read out the names. "Mark, Stu, and Mike!" Michelle smiled when she heard Mike's name.

Ginny asked Robert who the two other guys were.

" I know Mark a bit. Not really into the BDSM but likes sex and Stu I don't really know him that well.

Ginny said, "maybe they'll go easy on her."

The three men were getting undressed and Michelle was looking at their sizes. She took Mike's hand and said, " Ass, Mike?"

"You bet, sweetie."

Mark was as endowed as Mike so she said "mouth and Stu, you get my pussy."

Michelle told Stu to lie down on the mattress and she began to suck him. Once he was hard, Michelle climbed on his cock and sat down on it until it disappeared in her pussy. Michelle was now sucking on Mike while riding Stu. Mike pulled out, took lube and applied the gel to his cock and inside of Michelle's asshole. Kneeling behind Michelle, Mike slid his cock slowly into her ass. Mike liked Michelle and was not looking to hurt her. Once he was in, he nodded at Mark who positioned himself by Michelle's mouth.

"Open up, honey," Mark said to Michelle. She opened her mouth for him and he pushed his cock half way in. The three cocks soon were in rhythm as Mike went deep into Michelle's ass as Stu slid his cock back. Michelle was starting to feel the beginnings of an orgasm as the cocks kept up their pace. Stu was the first to cum, driving into Michelle's pussy as Mike pulled half way out of her ass. Mark gripped her head and was driving his cock into her mouth until he groaned and began to cum into Michelle's mouth. She swallowed most of his cum, but some leaked out of her mouth. Mark collected the seeping cum on his finger and fed it back to Michelle. Now Mike was driving his cock into Michelle's ass. He grabbed her hips and felt his cock go in as far as it could. Two more thrusts and he was filling Michelle's ass.

As Mike withdrew, Jonathan announced that Michelle was know a member of the club. There followed applause and Jonathan announcing that registration for the races at Connie's in four week's time would be open after a break.

The talk was all about the races and who would enter after Mike returned to the table.

Ginny leaned into Mike and whispered "how's Michelle?"

Mike whispered back "her ass is really sore from the paddling but she is going to be fine. She said she will come and sit, well, stand with us the rest of the evening."

Michelle returned just as Jonathan began to announce the rules for the races.

Jonathan began. "There are two races, one for male horses and one for female horses. If there are three or less entries in either race, that race will be cancelled. Each pony will pull an identical cart. Each pony will wear bell nipple clips and a bit in their mouth which will include an o ring gag. Each pony will wear a tail that is attached to a six inch long three inch wide butt plug that must be inserted by the driver. Each driver will be supplied a buggy whip. If you enter a partial entry you may list your driver on race day. However, if you have no driver one hour before post time you will spend one hour being chastised by anyone who wishes. Based on wagering, there will be prize money for win, place and show. The pony who finishes last will spend one hour being punished by a variety of implements that will be determined by our hostess, Connie. Then one hour as a sex slave to our female attendees and one hour as a sex slave to our male attendees. Any questions?"

"You have 30 minutes to submit your entries. Good luck!"

Jonathan joined the others and Don and Carol came over.

"Mike, what do you think?"

"Think about what?" Ginny asked.

"Your dad has made an interesting proposal. He would be your driver and I would be your mom's."

"What? Seriously?"

"I said that it was up to you. I said that I wanted to hear all the rules so I knew what was involved. Now, I know. Now, you know."

"It will be a bit of fun, honey," Carol said. "Say yes."

"Ok, but if Ginny loses, Carol is my slave for a day," said Mike.

Don said "agreed."

Ginny said, "well, you're going to be putting a butt plug in your daughter!"

They filled out the forms and gave them to Jonathan. More slips were handed in and at the end of 30 minutes, Jonathan announced time was up.

Jonathan held up his hand for quiet. "We only had one male horse apply so there will not be a pony boy race. We have, however, a number of pony girls entering. We had one come in by text and that would be Kathy and she will name her driver on race day. Hope so for your sake, Kathy."

Jonathan picked up the next slip and read off Susan and Daniel. Ginny looked at the others and it appeared they didn't know them either. "Ahh, send Jonathan, our newest member Michelle and her driver will be our hostess, Connie."

Ginny elbowed Michelle in the side and asked her when this happened.

"After the initiation. She really is quite nice and, well, gorgeous!"

"She knows how to handle a pony girl, too. I should know!" Ginny said. Michelle smiled.

Jonathan continued. "Well this not expected. Ginny and her driver, her father Don!" There were murmurs and some applause with this announcement.

"Robert and Ellen have entered. Our sixth couple is Carol and her son-in-law Mike will be the driver. Grace has entered and her driver will be...me!" Laughter and applause rang out.

Someone, who Ginny couldn't see, yelled out, "Let the male enter. Who is it."

Jonathan looked at Connie who yelled that if those entered don't care, let him enter.

There were no protests.

"Very well. Stu and his driver will be Barbara." Jonathan announced. "So that's our field. See you all at Connie's place in four weeks."

Things were quiet at Mike and Ginny's house in the days that followed. Don and Carol had come over a couple of times for dinner. Ginny, of course, was naked and Mike tried to get Carol to strip but she declined saying that Mike and everybody else would see all her charms at the race.

Ginny had talked about the fact that her father was going to do some intimate things to her body to prep her for the race.

"Are you worried about your father losing control?" Mike asked.

"No, I am concerned about me losing control!"

Mike smiled and hugged his wife. "You are the most sexual person I have ever known. If you remember that it's just sex, maybe that will help. Besides, I'll be doing the same things to your mother and I don't plan on having sex with her unless you lose."

Ginny felt a bit better after that exchange. She started to think more about the race and who was going to be Ms. Bossert's driver. She gave no hints when Ginny asked her at work.

Race day arrived. It had rained the night before but the day was glorious. Ginny and Mike were driving Grace and Jonathan.

"Since you're going to be a driver, who is going to emcee?" Mike asked Jonathan.

"Connie said that Richard was going to do it. Lester will get the stalls ready and George will serve drinks and snacks. Connie has promised them some alone time with the loser. Oh, Mike, I am sorry. You don't know who these people are." Jonathan explained who they were and both women nodded their heads as Jonathan described what each man did on Connie's estate.