James woke in the mid afternoon after sleeping from his small panic attack that he had last night about what to do. James got out of bed and walked over to his shower and set it to a very hot setting. It wasn’t scalding hot but hot enough that it did burn a little. James needed this so he could get to thinking of a plan on how he was going to get everything to work. After James’ hot shower he put on a pair of jeans but avoided a shirt for now. James walked downstairs to see that the library was completely empty. James got this gut felling that something was going to happen and quietly made his way to the kitchen to grab some breakfast. James was happy that there was some fruit so he didn’t really need to cook anything which allowed him to return to his room so he could avoid Twilight, Trixie, or even Rarity if she was here making a plan with the other two unicorns. James shuddered at the idea of Rarity coming up with plans because he knew how scary crazy smart she was when she really wanted something. James needed to come up with a game plan and so he went to his sketchpad to begin jotting down ideas on what to do. Thirty minutes later this was all James could come up with.

“I don’t have a fucking game plan at all.” James said to no one in particular except himself since he couldn’t come up with a single idea. So James did the next best thing he began writing a letter about him having to leave for a very long time for something that the princesses wanted him to do. After about a quarter of the letter written James ripped it up since he knew that he couldn’t get away with it what Twilight being Celestia’s star pupil and everything. James was beginning to lose all hope of ever trying to get this to work until Owlowiscious came in with a book.

The book that the owl came in with was a book on plants and herbs. James picked up the book and saw that one of the pages was bent showing that it was marked to read later. James opened the book to see that the page was about magesbane. James cringed at the thought of using magesbane against the three girls but knew that he might have to if he wanted to come out of this alive and get everything to a point that he could work with. James read the entry a little more seeing that it told of another plant called the pegasusjacket. The pegasusjacket could be mixed with magesbane to not only cancel out magic but also knock out the magic user. James smiled as a plan came to mind on how he could get this to work. James would need to make a trip to the Everfree but if he could get this flower then this would work in his favor. One effect the flower had was that it would put the magic user to sleep if they ingested it.

James put on a working t-shirt as he headed for the Everfree forest to get the pegasusjacket. James entered the forest and headed to the waterfall that he used to meditate at to find the flower. The flower likes to grow near a large source of water in a dark place. The waterfall had many nooks and crannies that the flower could grow in. James reached the waterfall and started his search. It took James an hour but he was able to finally get the flower. The flower had yellow and black petals with a stem that contained thorns. James smiled that he had the flower and to be on the safe side he grabbed a few more just in case he needed more. James left the forest and headed for the library to start up the mixture.

Rarity’s Boutique

Twilight and Trixie were standing naked in front of a mirror as Rarity was taking measurements. Rarity had this idea that if the three of them were going to win the bet against the others then they would need to look as beautiful than ever to get his attention. The clothing that Rarity had in mind to make were going to be very slim and tight hugging dresses that were going to show all of their womanly charms. Twilight was going to wear a lavender dress that was bare back and barely stopped above her butt. The front was crossed around her breasts covering them but showing the cleavage well enough that little to the imagination couldn’t do anything more. Trixie had her dress in the back with an X fashion but her held by thin straps. The front of the dress covered her breasts separately so anypony that looked could see the middle of them. Rarity’s seemed to really be on edge, as it didn’t leave much to any imagination at all. The dress was pretty much a skimpy dress that would easily make James faint from even looking at her.

“Rarity are you done yet because I’m kind of getting tired standing here with my arms spread. I feel scared that James is going to come in and see me in this position and try to feel me up. Though I wouldn’t mind that as much as I love him but I don’t just want to jump straight into it without any romance.” Twilight tried to get Rarity to speed up her process because she was losing all feeling in her arms.

“Keep calm darling if you want to make this bet an easy win then we need to look our absolute best. Besides I don’t hear Trixie complaining at all.” Rarity said smiling at Twilight at how well that the dresses were coming along to make them look sexy.

“Trixie isn’t complaining because she fell asleep a few minutes ago when you went to make the front of the dress hug our breasts tightly.” Rarity looked over to Trixie and saw that she was actually asleep. Rarity just rubbed her eyes and decided to give Twilight and Trixie a break for a while. It was the least that she could do since she has been at this for ten hours trying to make the perfect dresses. As Rarity left the fitting room there was a knock at her front door and she answered it to see Pinkie, Rainbow, Spitfire, Lightning, Fluttershy, Lyra, Octavia, and Vinyl. The eight mares smiled at Rarity as she let them in to have a seat.

“Good afternoon girls, is there anything that I can get for you?” Rarity asked trying to keep a level head about the eight mares visiting. All the mares just asked for a simple glass of water and Rarity went and fetched eleven glasses for everypony. As Rarity exited the kitchen she was being stared at with fury from the mares and as Rarity looked to her right she saw the fitting room door open and it showed the dresses that she was making. Rarity was feeling her chest tighten as she was waiting for interrogation to start.

“What exactly are those dresses for there Rarity?” Spitfire was first to ask a question to know more about the dresses.

“Those are just extravagant dresses that I am making for a special night whenever it may come.” Rarity lied through her teeth hoping to deter any conversation away from the dresses.

“If they were for a special occasion then why exactly are they labeled with Rarity, Twilight, and Trixie?” Lyra was next to ask a question as she saw through Rarity’s lie.

“Don’t tell me you are making sexy fun time dresses for you three so you can easily seduce James by showing off your bodies. That is so unfair that you three can get dresses that easily make you win this and then not give us any real playing field.” Pinkie voiced her opinion and she didn’t look very happy that there wasn’t any fairness in the competition.

“Please Pinkie I’m just using what I have available to me to help in this bet. I don’t remember there being any rule saying that I couldn’t do what I do best to help my team out.”

“So that doesn’t give you any right to make us look bad to James just because you are a good fashion designer. I didn’t think that you were so shallow that you would do such an underhanded thing to win this.” Rainbow was now getting after Rarity for her dresses and Rarity did feel a little bad about what she did. As the mares were about to have at it with Rarity Twilight showed up with Trixie in tow.

“What exactly is going on here? Why is everypony getting so upset?” Twilight asked looking at the mares trying to see what had them all in a fuss.

“Nothing we were just here to have a chat with Rarity until we saw her dresses and were wondering why she was being so shallow.” Lightning Dust explained to Twilight as she pointed to the door showing the three dresses. Twilight saw why it would make them so angry and she looked at Rarity with a look that pretty much said that she better do the same for everypony else.

“Okay girls to make this an even playing field again how would you all like a personalized dress like those to help on your dates.” Rarity hung her head in shame for being a shallow friend and try to make this a one sided bet for her team.

“Very well then Rarity since you offered and realize the unfairness of this then we accept your offer.” Fluttershy spoke in a soft quiet voice but Rarity could hear the hurt and seriousness that is held to show how bad she was. After everypony was able to settle down and all had something to eat and drink they all headed back to the fitting room so Rarity could get started on the other dresses.

Library

“Dude you do know that after you do this and they wake up they are so going to kill you for this right?” Spike was at the library with Sweetie Belle, Applebloom, and Scootalo just hanging out. If hanging out consisted of having your pants on the ground and three girls taking turns blowing you then James would need to hang out with the eleven mares more often. After Spike had his pants pulled up and the girls made themselves look decent James then explained what he was doing. The girls were more than happy to help as they were still trying to get their cutie marks. James nearly lost his mind as he wanted to tell the girls how they would get their cutie marks but when he mentioned it to the others he had his ear nearly talked to death by all of them. Apparently you were supposed to find out your special talent on your own and not get any help from others. James just didn’t argue this even though when the girls explained how they got their cutie marks was because of Rainbow Dash made a sonic rainboom so that was kind of indirectly being helped by another pony without figuring it out yourself.

“Spike I am very well aware of the situation that I am in. If I don’t do this though then I won’t be able to get them all to at least think about the harem. As far as I can tell though the only two that were dangerous are Twilight and Rarity. Twilight just because if I break her heart then I get the wrath of her friends, the princesses, and even her brother and dear god help me if I have to deal with that. Rarity on the other hand I feel that she would get revenge that would just be so crazy that I don’t even understand how it would work along with also being attacked by her friends, the princesses, and then Twilight’s brother just because Twilight would ask for his help. Trixie I could probably easily keep her from hurting me since I was the first to show her any kind of friendship when she arrived here. So at the worse I would just probably receive a slap across the face and be shunned for the next while.” James knew that his idea was crazy but there was no other way that it could possibly get any worse. James was going to make this work especially since he had to go back to the Everfree to get a rainbow root so he could get the taste of this concoction to not be noticeable. As James was working his phone started ringing. James picked up the phone and saw Trixie was giving him a call. James swallowed all of his pride and maybe his last breath as he answered.

“Hey Trixie what can I help you with?”

“Hey James I just wanted to ask you if you could start cooking dinner because me Twilight and Rarity will be over later.”

“Sure Trixie I get started on that right away.” James hung up his phone and smiled at how this situation just turned better for him. James went to the kitchen and saw the food that was set out for dinner. James knew what was wanted to be made and got to work. He read the book and learned that it would take two hours for the sleeping drug to take effect. James cooked the food and was able to get the drug mixed in with it. James knew that the other mares would be watching to make sure nopony cheated so he had to be careful not to do anything that would give away any intention that he had. After the dinner was finished there was a knock at the door and James guessed that it had to be the girls. James walked towards the door and opened it. When James opened the door he just about had a near heart attack and nearly blew a load in his pants out of sheer arousal.

The girls stood at the doorway in the dresses that Rarity prepared for the three and it was almost too much for him to handle. They looked absolutely stunning in their skintight dresses that showed off all their feminine features. James took more than a few glances at their nearly exposed breasts trying to keep himself from falling to the ground. James moved to the side and as the girls walked in they used their tails to brush against him to make him even feel more pleasure. James was beginning to think that he wouldn’t be able to last the whole entire night. They headed for the kitchen as the girls stayed close enough to him to have their tails brush against him as he was forced to watch them sway their flanks in front of him drawing attention to their shapely rears. James was trying so hard to keep his erection in his pants so he wouldn’t take all three of them then and there.

They reached the kitchen and settled down for the lovely meal. Twilight and Trixie sat to his right while Rarity was at his left. As they ate their meal Twilight, Trixie, or Rarity would once in a while brushing their tail against him. As the night got on further with the meal they got bolder in their attempt to get the mans attention. Rarity was playing a woman that dropped everything and when she dropped something it would be near James’ crotch. As Rarity leaned down she would brush against him just trying to egg him on and she would torture him with small glimpses down her dress to see her breasts. Twilight just breathed on the nape of his neck and was nibbling his ear lobe making him groan. Trixie used her tail and guided James hand to her thigh near her marehood and moved it up and down her thigh. James was breathing heavily now as he was stimulating Trixie and probably the other girls as he was making Trixie release slight moans. James was feeling his head get fuzzy and light as he was losing himself to the pleasure. James had to do something or risk failing in his plan. James took all of his courage and got up out of his seat. The girls looked at him worried that they did something wrong.

“Hey girls how about we take this to the living room and dance?” James needed to blow off some more time for the drug to finally take full effect. They were already starting to feel the effects of the drug and they still had an hour left before they were out. James had to make sure that the girls ate the food and weren’t suspicious of the food if he wasn’t eating it so he also ate the drugged food. James was glad that he talked to Spike about making sure all of them got to bed after they all fell asleep. Sweetie Belle was more than happy to help out, as she wanted to get revenge on her sister for threating Spike one day. James never asked and Spike never explained so it was just left at that.

The mares got out of their seats and walked over to James. When they were standing in front of him Twilight wrapped her tail around his left leg and looped her arm through his left and placed it between her breasts. Rarity took his right side by wrapping her tail around his right leg and looping her arm through his right and placing it between her cleavage. Trixie then walked in front of him and wrapped her tail around his waist and had her flank pressed to his crotch. God these girls really wanted James and he could tell that this was going to be a lot harder if he was going to have to do this with three other teams of mares.

Once in the living room of the library the mares adjusted around James so they could all dance together. They kept their tails wrapped around him so they would have an excuse to rub their bodies against. James couldn’t tell them to stop because he didn’t want to hurt their feelings. James looked at the clock and they had forty-five minutes till they were out cold. They started off slow in movement after Twilight used her magic to play a slow dance song and dim the lights. As they danced the girls got closer and closer until they were practically on him rubbing their bodies. Now that they were so close the mares started giving little teases to the already aroused man. Twilight would sneak a kiss on his neck, Trixie would run her tail along his leg making him shiver, and Rarity was just face to face with him giving him the best view of her breasts. As the dancing got more intense he could feel their tail move around his body.

They mares began to move their tails to his arms and pants. Twilight took his left arm and brought it to her marehood and Trixie did the same with his right arm. James could feel the heat coming off the two women and guessed that if he could move his hand to Rarity’s marehood he would be able to feel the heat she was giving off. Rarity was using her tail to unbutton his pants, which to James was an amazing feat to behold since it was her tail but it was probably helped by magic he guessed. James looked at the clock and saw that they had thirty seconds left. James used the last bit of his will power to hold out for the rest of the time. As James held on the best he could it was like time slowed down. James just kept his cool and counted down the last few seconds that were left. Twenty seconds left and the mares were getting closer, fifteen seconds left and they were still incoming, ten seconds and they closed their eyes and were going on for a kiss, five seconds they were centimeters away. Time was up and they all fell to the ground asleep. James was still standing but fell to his knees but before he fully hit the ground he whispered a thank you that he was able to last the night.

Outside

The eight other mares were outside watching the events unfold. A few of them were shifting on the ground because they were getting heated themselves at the scene. As they watched they saw the four of them fall to the ground and fall asleep. The eight other mares giggled at the failure of the date and were glad that they had a better chance. The eight of them then talked about who would be next to try and seduce James. After they talked they agreed that Octavia, Lyra, and Vinyl would be next. Then after them would be Rainbow Dash, Fluttershy, and Pinkie Pie. The ones to go last would be Spitfire and Lightning Dust but they didn’t mind, as they were certain that they could easily win this. They all went their separate ways to get ready for their chance to win.

Author's Notes:

One team down with three to go. Please also take the time to re-read the chapter before this because ErikTheSoulReaper pointed out that I forgot a few things and I have them put in so please take the time to read it again.