Finishing School

A three point-of-view tale of cuckoldry, voyeurism, and coming of age.

Cast of Main Characters

Jonathan Borden - Son

Kelsi Borden - Mother

Brent Borden - Father

Locations in this story are real, but this is a work of fiction. All characters are 18 years of age or older and are consenting participants. Enjoy!

Jonathan

My name is Jonathan Borden, and I am about to start my senior year at Culver Academies. It is a boarding school in the middle of Bum Fuck, Indiana for Chicago socialites, wannabe Tik Tok and Instagram influencers, future military leaders, athletes seeking Division I college scholarships, and brainiacs hoping to be the next Elon Musk and Jeff Bezos. It is a melting pot of the Midwest's up-and-comers located on the shores of Lake Maxinkuckee (yes, that's its real name), but everyone just calls it Culver Lake. The school and lake are in North-Central Indiana, about two hours from Chicago, two hours from Indianapolis, and three hours from Detroit. Of all the cliques, the jocks and socialites tend to blend, but the others seem to isolate. The military brats even have different uniforms, pretend ranks, and additional military classes, formations, and duties.

As for me, I don't fit in with any of the groups. My parents sent me here after my first semester in the Chicago public school system where I was constantly harassed and sent home with black eyes and bloody noses. Rather than send me to a 15 thousand dollar per year private school in the city, my brilliant parents decided to ship me off to a 50 thousand dollar per year boarding school.

"It will help him toughen up!" Said my dad.

My mom reasoned, "You'll be able to find more kids with similar interests at Culver than you would in the city."

Neither could be farther from the truth. If I was a loaner in the city, I'm practically invisible at this institution of higher learning and refinement. I don't have any friends. I don't participate in any extracurricular activities (not that I would be any good if I did). The only thing I have going for me is that my parents actually own a lake house on the western shore of Lake Maxinkuckee. This doesn't make me popular with any of the other kids as several other students have parents with the same set-up, but I have a first class VR gaming rig set up in the basement. Of course I can only use it on the weekends when I have passes off campus, but as a senior, every weekend is free. For once, I am actually looking forward to leaving the city for Indiana.

"I have a feeling that this is going to be your year, Honey! Are you excited to be a senior?" My mom, Kelsi, asked.

"I'm excited to have more time at the lake house, but besides that, I don't see anything about this year that will be different from the last three, Mom."

"Well, make sure you invite some of your friends over. They're lucky to know someone with a place on the other side of the lake."

I had told my mom countless times that I didn't have any friends. Barely anyone even knew my name, let alone that I spent my weekends off campus. At least I wasn't getting my face pummeled every week. I was a C student with no talents outside of gaming. I wasn't muscular or smart or even funny. At 5'9" and 150 pounds, I blended right in with the background and that was the way I liked it. If I could live in my VR rig, I would do so happily.

"Just remember," my dad Brent chimed in. "No drinking and boating, and for God's sake, get a girlfriend so you don't have to take your mother to the Refinement Gala."

Fuck! I had tried my best to block that out. Every year during Parent's Weekend, the school hosted the Refinement Gala. It was a huge ball that served as a culmination of all the manners and courtesies that we had been taught across the previous three years. It was meant to act as the senior class's introduction to adulthood. It was expected to be a semi black tie affair in which everyone brought a date. Some of the military dweebs would even invite minor celebrities in the tradition of the military balls. There was always a rumor of some kid that someone knew who pulled it off and got some hot celeb or another to attend, but no one ever had any concrete proof. The only surefire way to be the laughing stock of the class was to be forced to take a parent or sibling in place of an actual date, which of course was looking more and more like it was in my future.

"Oh, leave him be, Brent. I'm sure Johnny has plenty of options for a date to the Gala."

My mom then turned towards me.

"But if you don't, Honey, I would be happy to be your date for the evening. Don't let your father get to you." She said with a scowl directed back at my father.

"Thanks Mom. Thanks Dad." I said as I hugged them each in turn and headed down to the car to start the trek to Culver for the fall semester. "I'll see you in a few weeks for Parent's Weekend."

Kelsi

"I don't understand why you are always so hard on him, Brent. You know he has never responded well to tough love."

"Tough love, ha! Tough love was what he got from those gang bangers in public school. I just want him to grow up and stop living his life in a video game, for Christ sake. He's never going to become a man if he lives in virtual reality half the time. We never should have bought him that rig. What I should do is take away his lake house privileges."

I just shook my head at my numbskull husband.

"He's been looking forward to all the time he's going to get to spend there this year. You can't just take it away from him. What kind of father would do that?

"The kind of father that wants to see his only child become an adult. That was the whole point of sending him to Culver in the first place."

I gave Brent an over dramatic eye roll.

"If you would open your eyes you would see that he is becoming an adult. He's more responsible, he's well dressed and groomed. Hell, his grades have even started to come up. Maybe if you wouldn't focus all of your energy on him finding a girlfriend, he would be more receptive to you. And besides, I would be honored to be his date for the gala. He doesn't need to be an adult in every way. He's only 18."

"He needs to get laid is what he needs."

"Brent!"

My mouth hung open in shock.

"I'm just being honest, Kelsi. If he had a girlfriend he wouldn't need to spend so much time in his virtual reality. You know when he's not playing war games he's spending his time with an anime girl in VR. I'd rather him use the lake house to get an actual girl in bed than jerking off with the help of an AI computer."

"And how would you know all that, Brent? Sometimes...I swear your mind cooks up the wildest rumors. He likes his video games. So did you when you were his age."

"Yeah, but I got out of it once I discovered I could see boobs."

"Jesus," I scoffed with another eye roll. "You're more childish than he is."

I left the living room and moved to our bedroom, partially to get away from Brent, but also so that I could look for Jonathan as he drove away. To be completely honest, Brent was right in a way, but Jonathan was still my little Johnny. He would always be my baby boy, and I didn't want to think of him with a virtual girl or a real girlfriend. Several of our friends were dealing with unwanted pregnancies, abortions, and children with STDs due to their promiscuous sex lives. I was happy that those weren't our problems. Sure, Johnny could use some real human interaction, but he wasn't hurting anyone: he wasn't hurting himself; he wasn't in trouble with the school or the law. He was just socially awkward.

Despite his awkwardness, he was becoming an adult. I could see it more and more over the summer. After a few days he would have a bit of stubble and have to shave. He was also no longer the scrawny kid he was as a freshman. He wasn't muscular or athletic by any means, but you could tell he was no longer a boy. By his father's definition, though, he wasn't a man until he's slept with a woman. By that reasoning he might not be a man until he's 40, if even then. The way I saw it, he'd be ready in his own time. Trying to force it could only end in two ways; he'd develop an unhealthy relationship with sex or he'd have a bad experience and would isolate himself permanently. Either way was unacceptable, and besides, part of me wanted to go to the gala with him just to see how much he has really transformed over the past three years.

Brent

Jonathan was on a path to irrelevance and his mother seemed to be indifferent. She was happiest pretending that Jonathan was still her little 10 year old when the reality was that he was an 18 year old that acted like a 10 year old. We sent him to Culver to give him every opportunity that his mother and I didn't have at his age. I had hoped that he would find something that interested him other than video games. Unfortunately his love for gaming intensified and his ability to contribute to society was stuck at pre-teen levels. I'm hard on Jonathan, but my father was always hard on me when I needed guidance, just like his father before him. Teenagers are dumbasses, and Jonathan was no different. I just needed to find the right way to reach him.

Kelsi thought I was being ridiculous when I said he just needed to get laid, and she had a point, but I saw that as a better result than our son living his life in virtual reality. I'm not as clueless as my wife would believe. I would never have agreed to buy that damn VR rig if it was just for Jonathan. Truth be told, I enjoyed using it as well. Kelsi and Jonathan seemed to be none the wiser. I knew that our son had a virtual girlfriend because I had stumbled upon it while playing around myself. There is nothing creepier than a bimbo anime waifu accidentally mistaking you for your son when you wander into the wrong program. I still can't get that creepy accented voice calling me "Jonatan" out of my head.

I know the odds of him actually connecting with a real girl his own age are rapidly falling. The more time he spends with that AI, the less likely he is to even try to find a girl in the real world. Going to the gala with his mother will only push him further into his isolation, but I don't know how to help him. Unfortunately his mother can't see how bad the problem is, and I can't explain without outing my own vices.

I was lost in thought in my study when Kelsi called from the other room.

"Brent...it's Jonathan on the phone. Pick up!"

I answered the phone on my desk.

"Hey Johnny! How was the first week?"

"Hey Dad. Pretty low key. Mostly just getting to know the teachers and going over the curriculum. It will start to pick up next week."

Kelsi was still on the phone in the living room.

"Make sure you study. Don't spend all your free time playing video games, mister." She said.

"I will, Mom. Don't worry." Jonathan responded.

"Any plans for the weekend?" I asked.

"Not really. Still getting my room in order, then I'll probably head to the lake house...maybe order a pizza."

I sighed. "Ok, try to get out and socialize. And can I ask you to do me a favor?"

"Sure. What is it?" He asked.

"I want you to ask a girl to the gala this week. Can you do that for me?"

"..."

"Jonathan, did you hear me?"

"Yeah, I heard you, Dad."

"So you'll do it?" Kelsi chimed in.

"Yes, Mom. I'll try."

"Good luck!" I said. "And we'll see you in a few weeks. Hope you enjoy your classes."

Jonathan

The first week of classes had gone really well, but after that phone call home, I couldn't relax and enjoy my weekend. I should have waited until Sunday night to call my parents.  Now all I could think of was trying to ask someone to the gala and getting rejected, because, let's face it, that is exactly what was going to happen.

I went to the lake house and went straight to my room in the basement. The whole level had been turned into my bedroom and living space for when I wanted to get away from school. I had an ugly red sofa, a 65 inch flat screen TV, a queen sized bed, a desk and computer, and of course my VR rig. It consisted of the console itself, VR goggles, haptic gloves, an omnidirectional treadmill, a gaming chair with different levels of haptic feedback, and several remotes, including my favorite, a simulated M-4 rifle with grenade launcher for my special forces simulator. The military nerds at Culver would probably nut at the chance to try it out instead of drilling with their old ass M-1 Garandes.

I slipped into the rig and set up a rescue mission in Fallujah, but halfway through I lost focus and was KIA along with half my team. I booted up my virtual living space and was greeted by Yuki. She was usually my only solace when I was in a bad mood, but today, even her cute accent and slutty clothes couldn't prevent me from thinking about what I had to do. And it's not like I can tell my virtual girlfriend that I have to ask another girl on a date because my father said so...how do I even explain that to an AI? Yuki could sense my apprehension and offered to give me a hand job. Currently that consisted of me holding my cock with my gloved hand and her using different pressure and vibration patterns to get me to cum. I had hoped to convince my dad to buy the full haptic suit, but that was now seeming less and less likely.

I thanked Yuki for the offer, but politely declined. Instead I said goodbye and turned off the rig altogether. Instead of spending time with Yuki, I laid on my bed and tried to figure out who the hell I was going to ask to the gala. There were several girls who I'd love to take, but they were all super good looking and as a result were extremely popular. They likely wouldn't even know who I was. I expected to get laughed at either way, but asking one of them would bring additional unnecessary ridicule by the rest of the class. There was a girl in a few of my classes that was cute in a homely sort of way. She was a bit nerdy, and really smart, but you could tell that she would be attractive if she cared to put any effort into her look. Her name was Lily, and she didn't know it yet, but on Monday she was going to get quite the surprise. The only problem was that I had no idea what to say.

Monday came and I was a ball of nerves. I had three classes with Lily, so that gave me several opportunities to ask her to the gala. I wasn't able to come up with anything clever, so I felt simple and straight to the point was the best way forward. Now I just had to build up the courage to actually go through with it.

First period was Calculus. I was so deep in hell with figuring out how to not fail that I was in no shape to ask Lily out after taking a beating from Mr. Biehl for 55 minutes. That gave me Biology to regather myself before trying again during US History.

I had successfully steeled my nerves and was ready to approach Lily after history class. I walked up to her and tried to break the ice.

"Hey Lily? How's it..."

Before I could even finish my greeting, Carmen pushed her way in front of me and started talking to Lily. I stood there dumbfounded as she deliberately turned to glare at me as they walked away.

"Well, strike two," I thought to myself. I still had lunch and Latin class during the last period where I could try again. Or I could just tell my dad that I tried and she said no. It would pretty much be the same result, and he'd never know the difference.

"No, I didn't just promise my dad that I'd try, I promised myself too. You don't want to be stuck taking your mom to the gala. You've got to do this today."

I repeated that promise to myself over and over in my head throughout the rest of the day. I could do this.

Lunch and the afternoon classes dragged on and on. Latin finally came, and while you would think it would have been the most boring class of them all, our teacher, Mr. Rhodes was hilarious. He was the only reason I stuck with Latin for four years versus switching to something more practical like Spanish or French. Of course I knew almost zero Latin, but I got Bs and didn't have to work really hard. Lily sat right in front of me, so when the final bell rang, I made sure to get right up and grab her attention.

"Hey Lily!" I started. "Are you heading straight back to the dorms?"

"Um, Jonathan...yeah, I am."

"Cool, me too. Um, can I ask you a question while we walk?"

I started with an easy question. Can I ask you a question. Get a first yes out of her before asking the big question.

"Uh, sure. Let me grab my things."

I walked with Lily down the hall to her locker. We talked about Latin and how it was too bad that it was our last year with Mr. Rhodes and how screwed we were going to be for taking a language in college. She grabbed her things and we carried on outside.

"So, what did you want to ask me?" She said.

"I...I, uh, was wondering if you had a date to the Gala yet, and if not, would you like to go with me?"

"Oh...um, sorry Jonathan. I'd really like to, but I can't. I'm already going with someone. But..."

I cut her off because I didn't have the strength to listen to the rest of her rejection. "Ok, sorry to bother you."

I turned across the quad and made my way toward the male dorm. I could tell Lily was trying to get my attention, but I just couldn't turn and face her. What was done was done. I had tried and the result was exactly what I expected. At least I could tell my dad that I tried and let my mom know to make sure she brought a gown for Parents' Weekend.

Kelsi

Even though Brent and I were disappointed that Jonathan wasn't able to find a date to the gala, I was proud of him just for asking. Brent, of course, pressured Jonathan into trying again, but after talking with him it was obvious that he truly tried and was truly hopeful that his friend Lily would say yes. After being rejected, he just didn't have it in him to try again. While I was sad for him, I was excited that we would have this last opportunity to have a makeshift Mother-Son dance. I would also do my best to limit the awkwardness for Jonathan.

I wasn't quite sure how to do that, but I figured I could try my best to act like an actual date and not like his mother. Brent was highly supportive and encouraging of that plan.

"I'm going to have a chat with Jonathan and tell him to treat you as if you were on a date," Brent said as if it were his idea. "He needs that experience and you'll need to play along, Kelsi."

I wanted to roll my eyes at him, but he was so in the zone that I doubt he would have noticed. We packed our things and headed out of the city for the Indiana countryside. The whole way, Brent continued on about how I should act, how Jonathan should act, and how he could help.

Finally, I had had enough. "I think we can figure out how to get through the evening without any help honey. Jonathan is growing up. I think he'll surprise you with how he treats me. But just in case, I'll be sure to give you all the juicy details." I gave him a silly wink to drive home the point.

That finally seemed to calm him down and the rest of the drive to Culver was uneventful. When we arrived at the cabin, we both got settled and unpacked what we had brought with. Mostly just some groceries for the weekend, a few sundries and snacks for Jonathan, and of course my gown for Saturday evening. I hung it in the closet with my heels and put my undergarments in the dresser for later. Once everything was put away, we hopped back in the car and made the drive to Culver for the start of Parent's Weekend.

Jonathan met us for lunch on campus and then we were invited to attend his afternoon classes. Having attended the previous two years, it was nothing new or exciting, but it was always nice to see the facilities and faculty that we were paying so much for. We sat through Physics and Latin, which were both way over my head, but Jonathan seemed to enjoy them both, and Brent seemed interested as well.