Finishing School Ch. 02

"Hi Jonathan! Should I just hop in?"

"Huh...oh, yeah. Hi Lily. Let me come around and give you a hand."

I made my way back to the side and took her hand to help her aboard. I had her sit in the co-captains chair while I went and untied us.

"You look amazing, by the way. I, uh, feel a little underdressed."

"Don't be silly." Lily said. "You look great. I just wanted an excuse to wear this dress before it got too cold for it."

Well, I'm happy you did. Do you still want to go for a cruise or head straight to dinner?" I asked.

"Let's go for a ride while it's still a bit warm."

I backed us away from the docks and set out for a ride around the lake. The lake was only two miles long, so a trip around only took about 15 minutes at a medium speed. Fortunately, there weren't too many fall boaters, so the lake was pretty smooth. I set Spotify to play a top 40 mix and showed Lily how to operate the boat as we took our first lap around the lake.

Like everything else, she seemed to be a natural. I let her take over the captain's chair once she was comfortable, and she took us on a second lap. After 30 minutes of cruising, we were both getting hungry and headed over toward the Culver public docks. I asked if she wanted to dock the boat, but she passed that responsibility to me. I pulled us into a free spot and tied us up. I hopped out first and took her hand to help her out onto the dock, and walked with her into the restaurant.

Dinner went much easier than I expected. Conversation came naturally between us, but most of that credit goes to Lily. Everytime it seemed like I had nothing to talk about, Lily was able to delve into something that interested us both. We talked about gaming, boating, and a little about college. I really loved spending time with her. For dinner, I had the pork tenderloin that Indiana is known for, while Lily had the Caprese chicken. Again, nothing fancy, but it was a perfect evening. I paid for the meal and we headed back to the boat.

It was now dark, so I had to put up the navigation lights, and we could only travel back to the house at idle power, so it took about 40 minutes. I was about to head toward our dock when Lily grabbed my hand.

"It's still nice out, why don't we stay out on the lake for a bit?"

"Yeah, yeah." I stuttered. "We can do that."

I pulled over to a shallow spot and tossed out the anchor and set the boat to accessory mode so the engine wasn't running. When I looked back, Lily had taken a seat on the rear divan and motioned for me to join her.

She looked so sexy. Her short skirt had started to ride up and showed a bit more of her thigh. Her voluptuous breasts were spilling out of her dress. I sat next to her, put my hand on her leg, and was immediately hard. Without hesitation, I leaned in and kissed her.

Kelsi

Brent answered the home phone after two rings.

"Good morning, Borden residence."

He always answered it the same way, like a butler serving a rich family. I've told him several times to just get rid of the home phone, that no one uses them, and that the only calls we receive at that number are from Jonathan or telemarketers. Brent always claims some excuse about a bundle, so since he wants to keep it, I usually let him answer.

"Hey Jonathan! Yes...Yes...Oh, good for you...That's great to hear. How'd it go? Uh huh...uh huh."

Brent shouted across the room to me, "Hey Kels! Jonathan is on the phone. Apparently he had a date with Lily last night, and he'd like to talk with you."

I got up and walked over to Brent in the living room, took the phone from him, and sat on the sofa.

"Hi Jonathan. How are you doing?"

"I'm good, Mom. How are you?"

"Oh, just fine, just fine. Your father says you had a date with Lily this weekend? How'd that go?"

"Um, yeah. That's what I called to talk about. Dad's, uh...Dad's not still around is he?"

I looked back over my shoulder. Brent had disappeared into his office.

"No, he's not. Is everything okay?"

"Yeah, yeah, of course Mom. It's just, it's kinda embarrassing and I'd rather talk with you about it. You know how Dad can get."

"Of course honey. Did everything go well with Lily?"

"It did. It was great. And I really have you to thank for my new confidence."

I giggled slightly at Jonathan's innocent reference to our not so innocent evening. I still got butterflies thinking about it.

"That's great to hear Jonathan. We're both so happy for you."

"Thanks Mom. It's just...well, Lily and I had sex on Saturday, and..."

"Jonathan! Did you...we're you..." I looked back over my shoulder for Brent and then whispered the last word, "Safe?"

"Yeah, of course Mom. That's not the problem."

"Oh thank goodness!" I sighed a huge sigh of relief. "Well then, what IS the problem."

Jonathan took a second to gather his thoughts.

"Well, it was...it was different." He said, unsure of his words.

"That is to be expected, but different how?" I went back into caring mother mode.

"Well first...it, uh, it hurt her more than I expected. She didn't seem to really enjoy it."

This time I laughed.

"Of course she didn't, Jonathan. She was a virgin, right. You've had health class. I hope you were gentle with her."

"Yeah, of course, Mom. I went slow. But even then, she pretty much had a grimace the whole time. And the blood...it wasn't a lot, but it was more than I was prepared for. "

"Did you do anything to warm her up first? It shouldn't have been all bad?" I asked.

"Um, I tried to go down on her, but...but she didn't want me to."

"I see, so what did you do? Walk me through it."

I can't believe I just asked that of my son. If he hadn't been inside me just a month ago, this might have been the most awkward conversation ever. As it was, it was only slightly awkward.

"Okay, so we were on the boat."

"On the boat? Jonathan, your first time with this girl was in public?" I practically squealed.

"Not really important, Mom. It wasn't planned. It was just a heat of the moment kinda thing, but yes, on the boat, but it was dark and private. Down by the sand bar along South Shore Drive."

"Okay, okay." I calmed myself. "Continue, please."

"So we started with some kissing. It was good. Definitely the best kiss I've had with her so far. We were both really into it. I did it...well, just like you taught me. I pulled her close to me, and in the heat of it, her breasts spilled out of the top of her dress. I took them in my hands, and her nipples in my mouth. She seemed to really like that."

I pictured Jonathan's face buried in Lily's ginormous tits and was immediately struck with a pang of jealousy.

I bit my lip to hold back a rude retort. "Mmmhmm, go on."

"Well, we did that for a good fifteen minutes. I was feeling up her breasts, and working my hands up her dress and feeling on her legs, but...but anytime I got close to trying to rub between her legs, she closed them and adjusted so my hand was back on her hip. I didn't try again after two attempts."

"It sounds like she wasn't ready."

"That's what I figured. I was happy just making out, but out of no where she said that she was ready, and that she wanted to have sex."

"What a slut!" Was my initial thought. There I went getting jealous again. Why did that keep happening to me? I had my night with Jonathan. It was amazing. Better than I could have ever imagined, and not because Jonathan knew what he was doing and was a sex God in bed. Quite the contrary. He was a nervous teenager with no dick control. But the adrenaline I got from doing something forbidden. It was electric! Just thinking about it and listening to him describe his night with Lily had my juices flowing.

But I had already decided that it was a one time thing. I had told both Jonathan and Brent as much, and I had resigned myself to that decision as well. Those feelings of jealousy and desire weren't doing any of us any good. I needed to push them back down and start thinking like a mother.

"What happened next?" I asked dryly, trying to push the inappropriate thoughts from my head.

"This is where it got kinda awkward. I got the condom out, but I hadn't used one before. I thought it would be simple to put on, but it wasn't as intuitive as I thought. I initially tried to roll it on backwards, but it wouldn't go. Then I started to panic. I flipped it around and got it on, but by then I had started to...to get soft."

"Typical virgin teenager." I thought to myself, even though Jonathan was no longer a virgin.

"Lily pulled down her pantyhose to her knees, and I climbed up on top of her, but...but."

"Go on, I'm listening."

"Well, she wasn't, like you, Mom."

My thoughts ran away again. "That's right, and no girl ever will be."

But I caught myself. "What do you mean?" I asked.

"Um, she wasn't, um, shaved?" Jonathan struggled to find the words again.

"Okay?" I asked, not seeing the issue. "Not every girl will be."

"That wasn't a problem. It was different, but she was also really, well, tight. That and the hair made it really hard to, um, find the hole. Then I wasn't fully hard, so I couldn't get it in right away, and I had to stroke myself to get hard again."

"None of this is anything out of the ordinary, Jonathan. You're both new to this. Lots of weird stuff happens during sex. Funny sounds, strange smells. When you're younger it's awkward and embarrassing. The more you do it you'll understand that it's just a part of sex. Nothing to be embarrassed about."

"Okay, that's good to know."

"But go on, tell me how the actual sex was."

"Not much better unfortunately. Like I said, it obviously was uncomfortable for Lily. I did my best to be gentle and considerate, but nothing seemed to help her. None of that mattered though, because I still finished pretty quickly. Not as quickly as my first time, but nowhere near as long as the second or third. I just...I expected it to be more like being with you, but it wasn't."

"This is what I was afraid of, Jonathan. You have an unreal expectation of sex because of what we did. You're not going to find sex like what we had with a girl your age. She has zero experience and doesn't know what she likes yet. On top of that, it's going to take her a few times before it stops hurting. It's also going to take a few times for you to stop finishing so quickly. Yes, you were able to fuck for a longer period after having orgasmed that night, but it's been a month. Your dick still isn't trained."

"I wish." Jonathan hesitated. "I wish we could do it again. Just so I can get more confident."

I was torn. The more he talked, the more I wanted to do it for him. For me too. But it would hurt more than it would help. I was the parent. I needed to be the strong one.

"That's not a good idea, Jonathan. That will just set more unrealistic expectations for you. Sex with Lily will get better. I promise. Next time, see if you can convince her to let you warm her up. Do that thing you did to me with your tongue. If that doesn't get her lubed up, nothing will. Trust me when I say it will be better for both of you if she's wet. And don't be afraid to use lube. Astroglide is your best friend. And for God's sake, DO NOT FORGET TO USE A CONDOM!"

"Assuming there is a next time." He said glumly.

"Oh come off it. You're not going to pout your way back into my pants. We've already talked about this Jonathan. The night of the gala was a great night. I am eternally grateful that we have the memory of that night. But that is all it can be. I would love nothing more than to hop in the sack with you whenever you are feeling down. I shouldn't be telling you this...but you deserve to know. The feeling I had when I was with you...when you were...inside of me. It was like nothing I've ever experienced."

"Really?" I could hear the excitement reentering his voice.

"Yes, really. But not in the sense that you're hoping for. It wasn't because you were a superior lover than your father. It was because of who you are. I love you more than anyone in this world. All mothers love their children that way. It's a byproduct of carrying you for nine months. It's even moreso for me because you are my only child. The thrill of being with you, of being unsure, of the taboo of having sex with your child, of being able to do something for you so intimate, so loving, and so forbidden. It was the most intense sex I've ever had. Not because it was great sex. You still have a lot to learn. And you will, with Lily or another girl your age. But that night was amazing for me because it was you. And you have to understand that it has to remain just that night. As badly as we both want to do it again. We cannot."

"Okay Mom. I understand."

"I know it hurts. Trust me, it is just as hard for me to deny myself those feelings. You and Lily need to make your own way of it. Communicate with her. Tell her what you like. Ask her what she likes. If she doesn't know, suggest things that she might be okay with. Don't compare her to me. That isn't fair to her. She thinks you lost your virginity that night too, so make sure she knows you are happy and grateful for it too."

"I will, Mom. Thank you. That...that really helps."

"You're welcome honey. Don't be afraid to call back and ask for advice. And maybe next time, take it inside. I can't imagine sex on the boat was very comfortable. It had to be cold too."

Jonathan laughed. "Freezing, Mom!"

"Ugh, boys. Always thinking with the wrong head." I laughed.

"Okay, okay. Thanks Mom. I'll let you know. I gotta get going."

"Bye honey. I love you."

"Love you too, Mom. Bye."

I hung up and phone and was surprised to see Brent standing there.

"What was that all about?" He asked.

I was caught off guard.

"How...how long have you been standing there?"

"I just walked in."

"Oh, well Jonathan apparently had sex with Lily this weekend."

Brent interrupted. "Attaboy Johnny! Good for him. Why did he want to tell you?"

I explained everything and how I gave him advice on how to make it better. I told Brent that Jonathan probably wanted to talk to me about it because we all know how intense Brent could be, and we both agreed that I most likely handled it better than he would have.

"I'm sure Jonathan will come to you for advice when he's ready."

"Did he compare Lily to you?"

"Yes, he did. I was afraid of that."

"Yeah." Brent frowned. "What did he say?"

"Not much. Just that it was different. But he did ask if we could do it again."

Brent's eyes perked up. "What did you say?"

"I said no, Brent. I'd already told him that, and I'm sticking to my guns here."

"I dunno Kels. I think you should consider it. In the right situation it could be helpful. And you said yourself that you wanted to do it again."

"I also said that it wasn't healthy for him and that I will not be the other woman to Lily. You just want to find a way to watch, Brent. I know what you're trying to do."

"Well, can you blame me Kels? That's been a fantasy of mine forever. You finally did it, and I was asleep upstairs for the entire thing."

I got up and kissed him on the forehead.

"I'm sorry you missed it honey, but I can make it up to you in other ways. Why don't you go pick out something sexy for me to wear. We can do a little role playing. Would you like that?"

Brent

I'll give her credit. Kelsi really knows how to turn it on when she wants to. I was used to having to beg to get her to wear lingerie to the bedroom and I wouldn't have dared to ask her to roleplay my fantasy of her fucking someone else. She sent me to wait in the living room while she went to change. All this to try to persuade me to give up pursuing her and Jonathan having another night together.

About 10 minutes later, Kelsi strutted out of the bedroom wearing a black lace bodystocking, Louboutin stilettos, and nothing else. Her hair was done in a high ponytail and her makeup was full on glam with large smoky eyes, huge false lashes, and bright red lipstick. I was immediately hard.

"Oh, I'm sorry." She said. "My husband isn't home right now. Is there anything I can do to take care of you?"

She kneeled on the coffee table and looked back over her shoulder at me. I couldn't believe she was doing this for me. I decided to see how far I could push it.

"Yeah, actually. I've been pretty stressed. I could use a little relief." I said. "Oh, and can you call me Jonathan?"

Kelsi frowned. "I don't think that's a good idea. I'm trying to help you forget about that. Pick another name."

I went with Thomas. It was a name of a work colleague. He was 6'6" and 270 pounds. He was quite intimidating and in my mind had to be hung. Imagining Kelsi with Thomas had me filled with feelings of anger and intrigue. Kelsi jumped right back into character.

"Let me help you with those pants, Thomas."

She had me undressed and my cock in her mouth in seconds. It was so sexy to watch her put on a show. She whipped her hair back and forth as she licked me up and down. She locked eyes with me as she stroked my cock.

"Oh no, what time is it?" She looked at the clock. "My husband, Brent, will be home in 30 minutes. Quick, come fuck me in the bedroom before he gets home."

She led me to the bedroom and sat me right in front of the mirror. In seconds she had mounted me and was moaning as she rode my cock.

"Oh my God, Thomas, your cock is stretching me out. I'll never feel my husband's dick again." She cried out.

I was in heaven. Of course I only lasted a few minutes with Kelsi putting on her act for me. I pulled her down into me and thrust deep into her as I came.

"What...what are you doing? Oh my God, I can't believe you just came inside me." Kelsi whined. "My husband. He's gonna be so pissed. He can never find out. Promise me. PROMISE ME, THOMAS!"

"I promise!" I said. "I'll take it to my grave."

"Good." She said. "Then get cleaned up and get outta here before my husband gets back. And next time, cum on my face and not in my pussy, got it."

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Meetings between Kelsi and Thomas continued weekly. Every week she'd have something new to wear. A pink and purple Honey Birdette set. A black latex bodysuit and knee high boots. A tiny white spandex top that barely covered her nipples and thigh high athletic socks. Kelsi's libido was through the roof. I could barely keep up, but I enjoyed every minute of it. I also kept Thomas's promise to not cum inside of Kelsi.

After a few weeks, however, the novelty began to wear off. As fun as the role play was, it wasn't the same as the real thing. Part of me now wanted to see Kelsi with the actual Thomas. Not only that, but my fantasy of seeing her with Jonathan had not faded as she had wished. I still thought about it. I still had the image of her riding our son's cock emblazoned in my brain. Playing make believe just wasn't the same.

I was home alone on a Friday evening in November when the door to the condo opened unexpectedly. At first I thought it was Kelsi, back early from shopping, but it turned out that Jonathan had made an unannounced trip home.

I got up to welcome him with a hug.

"Jonathan! I wasn't expecting you this weekend. Is everything okay?"

"Yeah, Dad. Everything is fine. Lily went home to her parent's place in Lowell, Indiana this weekend, so I figured I'd make a trip home too. Good to see you."

"Good to see you to. Anything I can get you?"

"Actually, is Mom home?" He asked.

"No, she's out at the store. Probably be an hour or two."

"Oh, okay. That's probably for the better. Can we have a chat?"

I sat across from Jonathan on the couch and let him get into what was bothering him.

"Well, I have asked Mom for advice about Lily a few times, and she's been very helpful, but she always gives advice from a woman's perspective. I...I guess I could use a man's advice."

"I'm glad you and your mother have been keeping up, and I'm happy for you and Lily." I said. "That's great, but how can I help?"