Finishing School Ch. 02

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

Jonathan Borden - Son

Kelsi Borden - Mother

Brent Borden - Father

Lily Tyler - Girlfriend

The locations in this story are real, but all events are a work of fiction. All characters in this story are aged 18+ and are consenting adults.

Jonathan

My life has taken a complete 180⁰ turn since the night of the Culver Academies Refinement Gala. What was probably the most dreaded moment of my 18 years turned out to be a blessing in disguise. Not so much in the sense that I'm all of a sudden popular, but I no longer feel like a nobody just drifting through existence. I still enjoy my VR rig and try to immerse myself whenever I get the chance, the difference is that I now have a player two by my side.

It turns out that Lily, the girl who initially rejected me when I asked her to the gala, is quite the gamer. I showed her my setup when she came over to the lake house for the first time. It was love at first sight. Not between her and I but between her and my rig. She immediately asked if I had a second setup and if we could play. I didn't have a complete second rig, but I did have an older headset and controller. I used the older version and let her use the full immersion rig. We played war games for what felt like two full days until we went back to school on Monday.

She's actually pretty good too. It took her a few tries to get used to moving in the rig, but once she did, she was quicker and more agile than me. Since that weekend, I've bought a second modern headset and controller. I haven't gotten a second rig or the haptic suit I've been eyeing, but maybe in the near future.

Obviously this all means that I've been spending less and less time with Yuki, the AI girlfriend that I had purchased for my VR system. That's obviously a good thing for me, but its been hard dealing with her during the scarce time I do spend with her. She sees that I have a second player logging in with me, and she knows that her gamer handle is LilyPad05. I've kept that program secret from Lily, but it's obvious that Yuki knows I have feelings for Lily. I want to move Yuki to the archival storage, but I haven't quite had the heart to do it yet. It's not easy being in a love triangle with an AI.

As far as a sexual relationship with Lily, we haven't gotten there...yet. She's still a virgin, and as far as she knows, so am I. It's not like I can say, "Oh yeah, after the Gala my mom and I had an all night fuck fest and she taught me how to please and fuck a woman." And she certainly wouldn't believe that I was with anyone else.

I did kiss her last weekend though. It was...awkward. Despite my newfound confidence, thanks to my mother, I was still nervous as hell, and it was obvious that Lily was too. She's never had a boyfriend, and according to her at least, she'd only kissed another boy on a dare at a party. Don't get me wrong, it was good, but it was closer to being like the first time I kissed my mom rather than the first time she kissed me. Her lips parted and it was a good long kiss, but she never really gave me the opportunity to give her a good French kiss. I'm hoping next weekend presents another opportunity, but in the meantime I was considering calling Mom to ask her advice.

Speaking of my mother...we've talked a bit about that night. Thankfully it wasn't awkward and it doesn't seem like she has any regrets. At the same time, although I haven't pushed for it, it doesn't seem like it's something that will be happening again. Mom seems like she's happy to keep it a memory instead of a recurring thing. I have to admit, it does make sense, much to my dismay. She says that she's happy that things with Lily are going well, and that I need to focus on her. Also, she's still a married woman and my mother.

It was hard to hear her break that news to me. I was hoping that we could make sex a regular occurrence. As much as I hate to say that my father was right, he certainly was. Having a girl in my life has made me almost completely forget about Yuki. I just never expected that girl to be my mother.

Don't get me wrong. I really like Lily, and things are moving along nicely, albeit slowly. But I can't get my mother out of my head. I'm sure sex with Lily would change that, but until that day comes, I'm left daydreaming about my mother's silky stocking clad legs, her full C cup breasts and perky little nipples, and most importantly her beautifully smooth vagina and how it looked when I covered it in my cum. And then afterward the way she looked at me and took a small taste before cradling me in her arms and telling me that she loved me and the way I made her feel.

I don't just want her again, I need her.

The worst part is that I've become distracted at school. I've never been an Honors student, but I have been able to get my GPA up to a High C to Low B average. Unfortunately the start of my senior year has seen that fall back to a mid C average due to my constant daydreaming of either Lily or my mother. Getting called on in class with a raging boner caused by inappropriate thoughts of your own mother is not a way to get ahead in class. Unfortunately I haven't been able to get these thoughts under control. That's really the only reason I haven't gotten rid of Yuki altogether. Right now, she's the only one putting out, and that's only because I can force her program to do so.

I'm taking Lily to dinner this weekend and then on one last night cruise in the boat before we winterize it for the season. Hopefully that leads to something more than a kiss.

Kelsi

My feelings and my hormones were all over the place for weeks after the night spent with Jonathan. The added pressure from Brent wanting to know every detail of the night and the clandestine but semi-obvious pushing from Jonathan to do it again had my brain feeling like the consistency of tapioca pudding.

Jonathan was the easier of the two to handle. I told him that I loved him, and that I was so thankful that we were able to share that night. To be honest, I didn't give him enough credit. He made me fuck like a teenager again, and I was filled with a renewed vigor for sex. I couldn't tell him that, but I did my best to let him know that I was entirely satisfied.

The truth of the matter was that he's my son, not my husband, not my lover. As much as I want to, and my God do I want to, do it again, I'm married to Brent. It wasn't hard to tell Jonathan that he should focus on Lily and that it wouldn't be right to be in a relationship with her and having sex on the side, regardless of who the other woman is. That's not how a man should treat a woman and that's not something I could do to his father. I could hear the disappointment in Jonathan's voice, but I could also tell that he understood.

Brent was a completely different animal though. From the moment I woke up the day after, he wanted to know every excruciating detail. Let me tell you, describing an extramarital sexual liaison to your husband is an extremely awkward affair, even if it was something that he wanted and encouraged. Describing sex with your son is one thousand times worse. In the heat of the moment it was exhilarating and sexy. Even reliving it in my mind was titillating. Describing it to Brent made it feel obscene, pornographic, and immoral. I hate to say it, but Brent's pressure to talk about it made that night lose its luster.

I joined him on the deck that afternoon after a much needed sleep and an even more needed shower. I threw on some sleeping pants and a t-shirt before tiptoeing through the house. Thankfully Jonathan was still asleep and would sleep most of the day away. But from the second I sat down, Brent was hounding me to tell him what happened.

I tried to get away with the basics. I told him that I went downstairs unsure of what would happen. I certainly wasn't thinking that we'd have sex, even though I had actually arrived at that conclusion before I even stepped foot on the first stair. I described how I told Jonathan that his father and I talked and felt that it was okay if he wanted to finish the kiss he started on the ferry. I told him that we kissed a few times. Nothing terribly inappropriate, but in the back of my head I kept hearing Brent's words, "if it leads to more."

Well of course it would lead to more. Jonathan's a teenager. His hands started to wander and one thing led to another. The sex was quick, as expected, and then we sat and talked for a while.

Then the questions poured in. How did I like it? Describe our son's cock. Was he bigger than Brent? Did I cum? Did I let Jonathan cum in me? What happened next?

It was overwhelming, awkward, and hard to answer without being ashamed of everything that happened. But he's my husband and he deserves to know the truth. I tried to do my best without being perverse, but it's hard to answer those questions without either turning bright red in embarrassment or getting turned on.

Brent's biggest questions seemed to revolve around how we got to having round two. I told him straight up...Jonathan asked if we could do it again and I said yes. I said that we could do it as many times as he wanted until the sun came up. He had the night, but after that, things went back to normal.

That seemed to satiate Brent...at first, but over the days the questions kept coming. He wanted to know if I kept my stockings on, then if Jonathan liked that I did. I didn't hold anything back. I explained how the stockings and their lewd design were what started the entire chain of events to begin with. As it turns out, Brent did know about the design in them. He thought that I knew about them and wondered why I didn't wear them with the lingerie he bought with them when we had sex the night before. I had no clue, so I wore an older pair for sex and saved those to have a clean and new pair for the gala.

Then the questions got more and more lascivious. Brent wanted to know if I tasted Jonathan's cum, how I liked sucking his dick, how he tasted. I had finally had enough.

"Brent, I'm sorry. I know that you want to know everything, and I promised you that I'd do my best to share that evening with you, but those kinds of questions make me very uncomfortable."

"I'm sorry, I'm sorry. I know Kelsi. It's just, I've been trying to wrap my head around everything. I'm happy for you, but part of me is..."

"Jealous." I responded for him. "Of course you're jealous. It's only natural."

"Yeah." Brent paused. "But not jealous in the traditional sense. More like, jealous that I didn't get to be a part of it."

"Be a part of it? How would you have been a part of it?"

"Well, I would have liked to have...well, I would have liked to have watched." Brent confessed. "I...I've always..."

"I know about your fantasy Brent." I cut him off. "You told me a few years ago after a few too many drinks."

"I did?" Brent turned white as a ghost.

"Yes, YOU did!"

"I obviously don't remember that. What...uh, what did you say?"

"I didn't say anything. I was disgusted by it. I couldn't believe that my husband was mentally picturing me with another man while we had sex."

Brent started to talk, but I cut him off again.

"But I understand it now. I can see how that...fantasy...could be something that appeals to you."

My heart was pounding harder than it was when I first started down the stairs to Jonathan's room a few weeks ago. I couldn't believe that I just confessed that to Brent. I didn't know what else to say.

"Can I ask how that night changed your feelings?" Brent asked sheepishly.

I nodded.

"Well, I saw us fucking in Jonathan's mirror. It was...well, it was one of the sexiest things I have ever seen."

My hands were shaking. My voice wavered as I confessed my insecurities, but I continued.

"Watching another man make love to me woke something primal in me that I didn't know was there. All of a sudden I needed more of it. I needed to see what you wanted to see all this time. And there it was. That it was Jonathan made it all that more special for me. Watching him do those things to me. Seeing him become a man. Seeing the looks on both our faces. Watching his cock enter me. It was...incredible!"

I could see the pained look on Brent's face. I was finally giving him the description he wanted, and it hurt. It hurt that I enjoyed it so much, but it hurt so much more that he didn't get to see it too. And I understood.

"Would you? Would you do it again?" He asked.

"I don't know, Brent. On one hand, yes, I'd love to...but I have to think about Jonathan. It can't be healthy for him, for us to have an ongoing sexual relationship. He's finally found a nice girl in Lily. I certainly don't want to be the other woman in their relationship, but what do you think?"

"I didn't think of it like that." Brent frowned. "I guess I'm being selfish, but yes. I want you to do it again, and I want to be a part of it this time. I don't know what that looks like, but that's what has been eating at me. Have you talked to Jonathan about it?"

"I have."

"And?"

"I told him the same thing. That it was a one-time situation. I enjoyed it, but it can't be a regular occurrence, especially not if he's dating Lily."

"I guess you're right. As hard as it is to hear. And thank you Kelsi, for sharing. I can't imagine that was easy to do, but I appreciate it."

I kissed Brent on the lips. Both of us were on the verge of tears.

"Thank you. You gave us an incredible night that we will all remember for the rest of our lives. I promise you that I will make it up to you somehow."

Brent

I'll be the first to admit that I didn't handle Kelsi's first time as a hot wife as well as I could have. It's one thing to fantasize about it and picture it in my head, but to live it is another thing entirely. I wasn't prepared for the emotions involved. I thought that watching Kelsi with another man, even our son, would be a dream come true. In a way it was. If only I had watched the whole thing.

I certainly didn't expect Kelsi to enjoy it as much as she did, and I never in a million years thought that she'd spend the entire night with Jonathan, having sex a half a dozen times in one night. Hell, she surprised me right off the bat when she took our son in her mouth right after they kissed. I should have known right then and there that things were out of my control and would not go the way I planned. But I was blinded by my desire to cum.

Cumming to the sight of Kelsi's pussy engulfing Jonathan's cock was incredible beyond words. I have pictured that night in my head every day for the past month. And that's the problem. I've become obsessed. Even more than I was before my fantasy became reality. I want...no, I NEED to see Kelsi and Jonathan together again.

It doesn't surprise me that Jonathan has asked Kelsi about another night together. I certainly can't blame him for trying. I still don't know how I feel about Kelsi's desires though. As much as I want her to do it again, it felt like a knife right to the heart to hear her say those words.

"Yes, I'd love to."

You never know how you'll respond to hearing your wife say that she'd love to fuck someone else. It felt like she simultaneously scooped out my heart and deposited it in my throat while at the same time pushing all the right buttons to turn me on.

She said that in the moment, "she needed more of it...to watch his cock enter me."

I still can't believe that I heard those words come from my wife. And it's all my fault. I wanted this. I suggested it. I put those thoughts in her head. I can't balk now that she's finally gotten on board. But the craziest feeling is that nagging in my gut that wants to see it again. Part of me wants her to want more. Hearing her say those words, as much as it hurt, also meant that it's entirely possible to see Kelsi and Jonathan together again.

Of course, she tossed out that carrot and then immediately pulled it back and gave me the whip. She won't interfere with Jonathan's new relationship with Lily. It makes sense. What mother would? And it's what I wanted for Jonathan all along. But my selfish desires don't care. Part of me wants to sabotage their relationship. Maybe Kelsi would comfort Jonathan with her body.

But how would I even do that? Especially without being caught.

No, that's not the right solution, but there is an answer somewhere. Now that it's happened once and Kelsi has admitted to her desire to do it again, I'm determined to make it happen. Somehow. Some way. Kelsi may be able to turn aside her feelings for now, but eventually they'll surface, and when they do, I'll be ready.

Jonathan

After school on Friday I headed to my parents' lake house while Lily went back to her dorm. The plan was to get ready and then take the boat across the lake to pick up Lily at the school docks before heading out for a cruise ending at the Culver Parks Department public docks just across the street from The Lakehouse Grille. It wasn't anything fancy, but then again, nothing in Culver really was.

Although we had been hanging out the past few weekends, we had yet to actually go on a real date, so I was nervous as hell. Actually, I was terrified. Lily was easy to be with when we were gaming or talking about gaming, but what if we didn't have anything else to talk about? And what the hell was I going to wear? I hadn't really thought this through. It was mid October. The temperature in the evening was beginning to drop into the 40s. It was an unseasonably warm day, but you never knew what it would be like out on the lake, especially once you got up to speed. If it was too chilly, it may end up being a very low speed cruise.

When I got to our lake house, I immediately set to getting the boat ready. My Dad's boat was a 2020 Cobalt R6. Not cheap by any means, but also not the biggest boat on the lake. It was incredibly nice though. It was a surf and wakeboard boat, although I rarely used it as such, but it did have a bathroom, sound system, wakeboard racks with a small roof, and all the upgrades, which were all convenient amenities for taking a girl out for a cruise. I threw a few blankets in with the lifejackets for good measure.

As for me, I decided on casual. The Lakehouse Grille was really just a bar and restaurant, so fancy would be way overdressed. I decided on a nice pair of khakis and a blue button-up dress shirt. I brought a light zip up jacket for good measure. At 5 o'clock, I went out to the boat, hooked up my phone to the bluetooth, and dropped into the water from our private dock.

It felt great to have the cool autumn air rushing past as I got up to speed heading north across Lake Maxincuckee. It made me wonder why I didn't take advantage of the boat more often. Who knows where I'd be next year or if I'd even go to college, but I certainly wouldn't have the convenience of a sport boat readily available like I do now. The cruise up to Culver Academies helped me to relax and forget about all my worries about taking Lily to dinner.

I pulled up to the school docks and Lily was already standing there waiting for me. I quickly glanced at my phone. It was only 5:25. I was early, but so was she. I moored up to the dock's loading area and got a good look at what she was wearing. I was floored. She'd always been a cute girl, and I had seen her all done up at the gala, but she literally took my breath away.

Lily wore a black, three-quarter sleeve minidress with black belt and gray knee high lace up boots. She layered with sheer black leggings and wore a gray, fur-lined sweater. Her voluptuous DDs practically spilled out of her low cut dress, of which she had left several buttons undone. I couldn't help but stare, but I didn't know if I wanted to stare at her breasts, her hips, or her legs.

She called out and finally broke me out of my trance.