James woke up groggily in the morning grabbing his head in pain because of the side effects of the sleep drug. Once James could get to his senses he saw that he was in his room laying on his bed. James was glad that Spike was nice enough to help him get to bed after that night. James groaned as he rolled out of bed to head for a shower to help clear his head and clean himself up. Once James was finished he headed downstairs to see Twilight pulling in a gift basket and she had the widest smile on her face. James was confused as to why Twilight was receiving a present because it wasn’t her birthday and no holidays have come up yet either. James followed Twilight to the coffee table and she was still smiling at him thinking that he was the one to get her the present. Twilight opened the present and released a loud squeal at what she got. She was given an ancient spell tome on arcane defense magic. Twilight rushed over to James and gave him a kiss on the cheek. As much James wanted to let her believe that he was the one that got her the present he couldn’t.

“Twilight not to rain down on your parade but I didn’t get you that present.”

“Of course you did James who else would get me such a present that I would enjoy?”

“I don’t know who could have done it but I think somepony is trying to steal you away.”

“Don’t worry James if they were they would never succeed because I belong to you and you alone. Also possibly some other mares but we will see where that leads.” Twilight said that last part quietly so James couldn’t hear her. Even if Twilight was loyal to James it didn’t mean that whatever pony was trying to win her over wasn’t going to give up. James wouldn’t interfere, as he wanted to see for himself if Twilight was truly loyal. Sure she showed her love for him but it was just his paranoia that had him so worried. James went to his room to wait for that phone call from one of the mares to go on the next date.

As James just lounged around in his room he picked up the book on herbs and plants and started flipping through the page. James was able to figure how to deal with the unicorn mares but he still needed something to deal with earth and pegasi ponies. Sure James could probably deal with the two earth mares if they were alone but with who they were teamed up with James needed this advantage. Octavia had the help of two unicorns and Pinkie had the help of two pegasi and it also didn’t help that one of the pegasi was Fluttershy. James could never find a reason to ever cause any serious harm to her because she was just too kind and caring of others. As James flipped through the pages he came across a flower called flightsbane. The flower could be used to strip a pegasus of their flight abilities if ingested for a short amount of time. James continued reading to see if there were any combinations of other plants that could be very helpful. As James neared the end of the entry he saw that if he could get some honeydew roses then he could make a special liquid that when swallowed would leave a pegasus in a state of unconsciousness. Now James had something to use against pegasi and unicorns but still nothing on earth ponies. As James kept flipping through the book he reached the end and got nothing to solve his little problem. James knew who everypony was paired with so James could possibly make this work but he would need to try something out.

James headed back downstairs to see Trixie on the couch reading her visual arts spell book. As James got closer Trixie looked up at him with a huge smile. James was wondering why they weren’t mad or anything since they didn’t succeed in winning but probably had to chalk it up to that they probably don’t remember falling asleep. James wasn’t really happy to make this request especially with such a good friend and possible lover but he had to see.

“Hey Trixie do you mind helping me check something out?” James was nervous to do this but he had to if he wanted everything to work out.

“Sure James. What exactly do you need help with?” Trixie was more than glad to help her future husband and was willing to help him anyway she could.

“I want to see if some parts of ponies would react under the same conditions as a human would if I were to put pressure here.” James did the action before Trixie could either accept or deny the request. Once James pinched the neckline meeting the shoulder Trixie passed out unconscious. James grabbed the back of her head and back and gently laid her on the couch so she could sleep it off. Just as he finished making sure that she was comfortable on the couch and covered with a blanket James turned around and saw Spike coming down the steps.

“Hey James how you feeling man?”

“I’ve been pretty good so far and I learned a few things that have been helpful. Also if you are headed out can you please get me some flightsbane and honeydew roses?”

“Sure I can but can I ask what exactly they are for?”

“Well you saw how I mixed magesbane and pegasusjacket to make that sleeping drug?” Spike nodded his head as he remembered helping James make that potion.

“Well essentially I’m doing the same thing but this combination is focused on dealing with pegasi.”

“Dude I know that I said that first concoction that you made was going to get you killed because of Twilight and Rarity but if you do that you are going to really die this time. I mean full fledged your body isn’t moving and nothing can bring you back dead. You plan on using this against Rainbow Dash the best flyer in Equestria, Spitfire Captain of The Wonderbolts, Lightning Dust that is probably a match for Dash in speed and stubbornness, and finally we have Fluttershy. I mean you do remember what she is capable of right? You heard the rumors about her stare and you are still going to do this.” Spike rubbed his head trying to stave off the headache that was coming because of James’ insanity.

“Yeah I truly have a lot of doubt that this thing would work. I also truly don’t want to do this either to Fluttershy because she is just so innocent. Then we have Dash, Spitfire, and Lightning Dust that could easily rip me apart if they so choose to. Though for my love of them I have to try no matter how insane.”

“I don’t even know why I am helping you but you are right. If it wasn’t for you my relationship the three mares probably wouldn’t have worked out so well if it wasn’t for your advice. I will help you but you must not mention that I helped you with these hair brained schemes.”

“Don’t worry Spike you will never be mentioned no matter what. This is my crazy ass plan that I have decided to go through so I will deal with all the consequences.” Spike left the library to go get James his supplies. James went back up to his room and waited for the phone call of the next team to ask him out. Once James reached his room he went over to his bookshelf and checked to see if he had enough of the first concoction that he made. James didn’t need much since he was dealing with only two more unicorns but these two were also emotionally hurt. James had enough to deal with Vinyl and Lyra so he went and sat at his desk drawing little cartoon characters on his sketchpad.

Octavia’s Home

The three musicians were sitting around trying to come up with the best way to win James. The three of them have been at it for three hours and couldn’t come up with anything. They knew James didn’t care about extravagance or anything of the sort so they wanted to make something from the heart. As they sat around neither one of them could figure out a single thing to think of.

“How difficult is it to think of something to give to James to show we care?” Vinyl asked as she threw down her pencil in frustration that she couldn’t come up with anything.

“Well we need to truly think on what James could truly love from all of us if we were to give him something.” Lyra was adding input as she pinched the bridge of her nose and looked at her blank note pad that had no ideas on it.

“Well I think we are going about this all the wrong way girls.” When Octavia said this the other two looked at her in confusion and were gesturing her with their hands for her to continue.

“We are trying to step away from what we do best. We are three very talented musicians and we aren’t even trying to use that to our advantage. So instead of trying to come up with some kind of gift for James why don’t we make him a song? This also won’t be just any song though that we have created. This is a piece of art that will use our musical styles to convey our feelings better than words.”

“Even then though Octavia how will that ensure our win. Sure we could make him fall in love with our music but where is the part where we truly use our skills of seduction to win him over?” Vinyl asked with a little crimson on her cheeks because of the thoughts she was having on seducing James.

“Oh but we will be able to do that Vinyl and very easily. I do hope that you two weren’t planning on wearing your dresses for long after dinner with James at my house.” Octavia grinned ear to ear apparently delighted by her idea on how to win.

“What exactly are you planning here Octavia?” Lyra was a little nervous at what the cellist had planned as she looked back tat the three dresses and Octavia trying to figure her out.

“Lets just say that when James hears us play and watches us play he won’t be able to resist us.” Octavia kept her grin as she looked at the other two mares who were slightly nervous at what she had planned.

Library

As James laid on his bed his phone started ringing. James looked at his caller i.d. and saw that Vinyl was calling him. James knew which team he was up against and felt a little saddened that they were the next to ask him out. James loved Vinyl and Lyra very much that he didn’t want to hurt their feelings in anyway. James looked over at the sleeping drug and sighed heavily knowing that he had to this. He may not be happy to do such a thing but it had to be done. James answered his phone before it went to voicemail.

“Hey Vinyl what can I help you with?” James asked trying his best to hide the little hurt that he was feeling.

“Hey James me and Lyra are at Octavia’s and were wondering if you would like to join us for dinner?”

“Sure Vinyl I would love to join you three for dinner.” After James agreed and went to hang up his phone he couldn’t help but hear the small squeal that Vinyl let out. James got dressed in another plain shirt and jeans since he needed to not show any favorites at all during these dates. As James headed downstairs he was stopped by Trixie. As James tried to walk past her she stuck her arm out stopping him. Before he could say anything though James got a slap to the face.

“What exactly was that for Trixie?” James was confused as to why his friend was angry at him enough to slap him on the face.

“That is for making Trixie fall asleep before she could answer you request.” After that was said Trixie walked off. James watched her leave and wasn’t sure if she was truly angry with him. As she walked off she swayed her hips left and right while swishing her tail to entrance him. James just shook his head and left the library.

Trixie

“Twilight may I come in for a second?”

“Sure Trixie come right on in. So what can I help you with?”

“James is headed out on another date. Lets go grab Rarity and the others and see how this goes.” Twilight got up than and walked next to Trixie and placed her hand on her shoulder. Once she did this they were teleported to Rarity’s boutique.

“Good evening Twilight and Trixie. What can I help you with today?”

“Hey Rarity. James is off on another date so we need to grab the others so we can watch.”

“Then let us be off then darling. We don’t have much time.” Twilight then teleported the three of them so they could grab the other five.

Octavia’s house

James arrived at Octavia’s house and was happy to see that the house was as beautiful as ever. James walked up to the door and gave a few knocks. What James saw next nearly blew his mind and almost made him pass out. Lyra answered the door wearing a dress in the color of her minty coat. It was designed that the front parted her breasts so you could see in between them and show off the middle of her back. The dress also stopped just right below the knees showing off her well toned calves. She gestured for James to enter and when he did he nearly blew a load in his pants like last night. Octavia was wearing a charcoal V cut dress that also parted her breasts but her back was covered. The dress ran down to her feet but was cut along the side showing off the stockings that she wore underneath. Vinyl was wearing a two piece dress that James didn’t think was possible to exist. Her top was red like her eyes that she was showing off making them stand out even more. The top was a mid rif showing off her toned stomach and was X crossed along her breasts. Her bottom was also red and were like a pair of shorts. The bottoms were only half way down her thigh and hugged her so tightly that it showed where she curved.

“God damn it Rarity why do you have to be so good at making dresses.” James silently thought to himself seeing that if these three were dressed like this then so were the remaining five. James knew that this was going to be another long night.

“So how are you fine mares doing this lovely evening?” James asked trying to keep the blood not only from coming from his nose but away from his crotch.

“Oh we are doing just lovely and now even better that you are here.” Lyra replied for them all as she let her warm breath run along James’ neck teasing the hairs on it.

“Well that is good to hear from you all.” James answered back trying to keep his heart in his chest.

“James if you could be a dear and bring out the dinner please while the three of us finish setting up the table that would be lovely.” Octavia requested his help using a low sultry tone that made that man shiver at how alluring it was to hear.

“Sure Octavia I would be glad to bring out our dinners.” James walked towards the kitchen to fetch the food and place the last of the sleeping drug in both Vinyl’s and Lyra’s food. The drug doesn’t work on earth ponies but that was what confused James a lot. James if the sense of things would consider himself an earth pony since he couldn’t use magic and couldn’t fly. These two facts is why James couldn’t understand why the sleep drug affected him. Though there was also the fact that he was a different kind of species that never existed in this world so it might be because of his biology. Whatever the reason was James knew he would have to be careful in case this was ever used against him. Lucky for James the food was labeled for who it was for.

Once the food was laced with the sleeping drug James brought the food out. When he exited he saw that the three mares had their back turned to him. The mares were setting up the table but as they did they were swishing their tails causing James to look down. James was too entranced to see that the three of them turn around and were looking at him. When Lyra coughed to get his attention James stood straight up blushing intensely that he was caught. The mares on the other hand didn’t mind as they walked towards him swaying their hips and making their breasts bounce just a little. Once they reached James they looked at him with half-lidded eyes and wrapped their tails around him and lead him to the table. As they got to the table James saw instruments set up in another room and knew that there was probably going to be a show after dinner.

Dinner was the same like it was last time back at Twilight’s but this time it was a little more intense. These three mares were a little more adventurous than Twilight, Rarity, or even Trixie was. Vinyl was pretty much sitting on his lap and slightly grinding herself on his leg. Lyra was using her tail to have James’ hand rub up and down her thigh and as he did so he could he the soft whimpers coming from her. Octavia was using her tail to put slight pressure on his cock and it was working. James was trying so hard to fight of the erection that was trying to form as the three mares were breathing slightly with their hot breath bathing over his body. Dinner was finished and James looked at the clock and started the countdown for the two hours until Lyra and Vinyl were out. James was glad that Octavia had a few glasses of wine, which would help when he sent her unconscious.

With dinner over James was now lead to the room containing the instruments. The walk there felt like hours as Vinyl kept grinding herself on James, Lyra kept using his hand on her thigh, and Octavia was exerting more pressure on his crotch. James was certain that he was going to lose it at some point but the image of either one of his friends hurt that they couldn’t be with him allowed him to endure no matter what.

“James please wait out here while we get everything set.” Octavia requested this as she drew a tiny circle on his chest lightly that made James shiver. As the three mares entered the room James leaned against the wall to help support him. James was breathing heavily from all the excitement that he was going through right now and was afraid that he was going to end up with blue balls before the nights end and he still had two more dates that he would need to go on. As James was able to calm down he was called into the room. When he entered it was dark except for the light on a single chair. James walked over and sat on the chair. Once James was seated the lights came on.

When the lights came on James couldn’t help the blood that came out of his nose and quickly punched his thigh to stop the erection from staying. In front of him were the three mares before but now they have removed their dresses and were now naked with their backs turned to him. Lyra was sitting with her new harp, Octavia was with her cello, and Vinyl to James’ surprise was sitting at a piano. Silence held the room for a while until Octavia started playing. As Octavia was playing she was moving her tail up and down James’ right leg. After Octavia played a few chords Lyra came in on her harp and followed Octavia’s lead and started moving her tail up and down James’ left leg. Once Lyra got in her few chords Vinyl came in on the piano and it was the most beautiful sound James had ever heard. Vinyl then followed the other two mare’s actions and moved her tail up and down James’ crotch. James was lost to the pleasure and sound of the music and the tails rubbing against him. James could feel all the notes and the emotions that followed them. James could tell that this was a trio piece that these three created to show their feeling for him. Time went on and James saw the clock that was thankfully in the room. He still had thirty seconds before Vinyl and Lyra were out. James started counting down the seconds to the sleep. Fifteen seconds and the song started to slow, ten seconds and the last few notes were played, five seconds left and the last note was held. After the notes were done Lyra and Vinyl passed out. Before Octavia was able to ask what happened James quickly knocked her out. James took a few minutes to gather his senses before he moved. Once he was able to think straight James started taking Octavia, Lyra, and Vinyl to their rooms. When all three mares were put to bed James left the house and headed back to the library.

Outside

The eight mares were out on the roof of an old abandoned building that nopony uses. As they watched Rarity couldn’t help but be proud at how well her dresses were working against James. She never thought that she would reach a point in her career that she would enjoy watching them be used against somepony that she loved more than making them. All the other mares were getting very antsy out how the date was going and couldn’t help but squirm. A few of them were panting heavily at the sight of how James was being seduced and were about to lose it. Once James left the house though they all got up and left in the shadow of the night to return to their respective homes for tomorrow.

Author's Notes:

Two dates down and two to go. There will be two other chapters coming out today so keep a look out for those.