A Reluctant Sex Instructor Ch. 01-02

And the worst thing of all was his loyalty. The only reason why we became friends was because I happened to help him when he was getting bullied. I didn't even mean to help him. In a billion parallel universes, this was probably the only one that I did.

When Tony first entered high school, he was small and pretty like a girl. That attracted a lot of bullies targeting him. He frequently fought back and ended up in bruises.

In the third week of high school, I happened to walk past him surrounded by four seniors in a corner. Somehow my body reacted and I ran over to help him. It was a heroic moment like in the movies. But unlike in the movies, both of us got beaten up badly.

But after that incident, we became friends. Or rather, he declared me his best friend.

Then six months later, he hit a growth spurt, became ripped, more handsome rather than looking like a girl, and suddenly became the most popular guy in school. He was the typical jock. Tall, muscular, handsome. And very rich. But unlike typical jocks, he was also smart, kind, and treated everyone well. Especially me.

Throughout the rest of high school, he kept me close. He asked his friends to become my friends. He invited me to parties. He made sure no one messed with me.

If he wasn't so loyal, perhaps I could hate him. But I can't. He did everything right, even when I didn't deserve it.

"Um..." I stammered, glancing towards my room, now plotting my escape. I never did well with tense and confrontational situations.

"Tony!" Lisa admonished her boyfriend. She was the only one who knew me best in the world.

Lisa was also another friend I didn't deserve. On the first day of school, we rode the bus together. We talked. Or rather she talked, I participated.

That should have been the end of the story.

Except Lisa also decided to become my friend. If not for Tony taking the top spot, she would have been my best friend.

Most people found me too weird and difficult to talk to. I agreed. I was weird. But Lisa didn't mind. She was gentle and kind. She took the time to understand me and made me feel comfortable.

"This is getting nowhere," Tony said sharply. I flinched, which made Lisa frown at her boyfriend again.

"Denise, take Tony to your room," Lisa said. "I'll talk to Ken alone."

----

"Ken!" Lisa snapped her fingers, drawing my attention and bringing me back to the present. "Don't start spiraling now, please."

"Uh... You haven't told me what the meeting earlier was about." I said, trying to remember the conversation we were having. We're talking about... me fucking her ass. "Does this... request got to do with the other night?"

"It's linked," Lisa said. "But they're two separate things."

"You know you're not making it easier for me to understand right?"

"Alright, alright," Lisa said. "Let's settle one thing at a time."

"Fine."

"So can you help me to... stretch my butt?"

"Couldn't you, I don't know, use a plug or something?"

"I've been doing that!" Lisa snapped. "I've been wearing a butt plug for months now. I've also tried a nine-inch dildo. But somehow it's different once Tony tries it with his cock."

Nine-inch? Damn.

"So how is this going to work?" I asked. "We're just going to... do the butt stuff until you can... accommodate Tony's?"

"That's the general idea," Lisa said. "And more, if you're comfortable."

"More?"

"I've always wanted to do DP with Tony."

"D-DP?" I stammered.

"Double Penetration. You know, having a cock in my pussy and my butt at the same time."

"I know what DP is... Uh, so you want me to have sex with... you two?"

"And Denise."

"Like... a foursome?"

"If you don't mind..."

"Uh, Denise wants to do that... with me?"

"She also wants to get used to anal sex. But she's even tighter than me."

"Um..."

"You don't have to give an answer now," Lisa added quickly. "You can take your time to decide."

"Right... So what's the other thing you wanted to talk to me about?"

"You know how Tony, Denise, and I are very... enthusiastic about sex?"

"I might have noticed that," I said drily.

Lisa giggled. "Anyway, I don't like to wear clothes after sex. My body gets very hot."

"Like the other night..." I muttered.

"Yeah, like the other night."

"I'll make sure to stay in my room whenever you three get... enthusiastic."

"Oh no, it's the opposite actually," Lisa said.

"The... opposite?"

"Well... we're hoping that you don't mind if... if we walk around naked."

"Oh..." That was unexpected. "So you want my... permission to... walk around naked after sex?" I asked hesitantly.

"Yes," Lisa said. "And in general."

"What do you mean by 'in general?'"

"Well, I don't really like wearing clothes at home... even when I'm not having sex."

"So you want to basically turn this house into a nudist place?"

"Not nudist," Lisa said quickly. "I'm not a nudist. I just don't like wearing much clothes."

"What's the difference?"

"Most of the time I'll wear just panties... or maybe a shirt if it's cold."

I wanted to ask if she meant either just panties or a shirt, or both. But I guessed I would find out eventually.

"And I'm supposed to be naked too?" I asked.

"Of course not!" Lisa said sharply. "You can wear anything you want. Or not at all. It's your choice. That's what I'm saying. We just set a rule where we can dress however we like."

"Oh... I don't think you want me to walk around naked."

"Why not? Tony does... at least in his room."

"But Tony's your boyfriend."

"I don't have a problem with you walking around naked, if that's what you want."

"If everyone's naked... I might... uh... ah, never mind."

"You know you can always tell me what's on your mind right?" Lisa said. "We've talked about this."

"Right. But some things might still be inappropriate to say out loud."

"More inappropriate than asking you to help me stretch my ass?"

I laughed. "That's a good point."

"So?" Lisa said. "What was it you wanted to say?"

"Um... I might have... an embarrassing situation if you and Denise walk around naked," I managed to say.

"Embarrassing situation?" Lisa raised her brows. Then she got it. "Oh! Well, if you're going to help me, it's not like I won't see your erection right?"

"Right," I said, still not quite believing Lisa was asking me to fuck her ass. And now I could see her naked. Or just with her panties on. Every day.

I've had a huge crush on Lisa even before she and Tony got together. I got to know her first, before Tony stole her away. Though it wasn't like I was ever going to be with Lisa. Still, it hurts a lot whenever I see my best friend being with my biggest crush.

"So are you comfortable if I start walking around in just my panties?"

"Uh..." This felt like a trick question somehow. Or my mind was playing tricks on me. Why was it so difficult for me to just say yes?

"You can look at me however you want, of course," Lisa added. "I really don't mind that. Denise would probably like it when you look at her in just her panties."

I imagined seeing Lisa and Denise walking around the house in nothing on except their panties. Everyday. And allowing me to look however I like.

It would be a sin not to allow them to do that.

"Sure... if you... don't have a problem with me walking around with an erection all the time."

Lisa giggled. "I don't mind."

"Uh, is Tony going to be walking around naked too?"

"Sometimes. But he usually wears boxers at home. You don't mind that, do you?"

"I rather not see Tony's monster cock."

She laughed. "I think we'll all get used to it after a while, don't you think?"

"Uh, right."

"Then... once you get used to it... maybe we can... go one step further..." Lisa said slowly.

"One step further?" I asked, warning bells starting to ring in my head again. "You know, if you want me to be less anxious about this conversation, it would be better for you to just say everything together instead of one after another."

"Oh... Um, the next one might be a little awkward."

"More awkward than the conversation we're having?"

"Um, if you don't mind... would you be uncomfortable if we... have sex when you're around?"

"You want me to watch you guys have sex?"

"Oh no!" Lisa said quickly "You don't have to watch if you don't want to... but you can watch if you want as well. Either way is fine."

"So you're saying you want to have sex in front of me?"

"Yes."

"Like in the living room?" I clarified. "Or the kitchen."

"Anywhere in the house... whenever we want."

"I could just stay in my room, you know."

"No!" Lisa said. "We don't want you to do that. This is your house as much as ours. We want you to be comfortable doing whatever you want, and not have to coop up in your room because we want to have sex on the couch."

"So if you two, or three, are banging in the kitchen, you won't mind if I walk in, grab a drink from the fridge, and watch you three bang?"

"We don't mind if you don't. It can be... very hot for you to watch." Lisa smiled coyly.

"So you want me to watch?"

"No Ken, you're missing my point!"

"Then what's your point?"

"The point is we can all do whatever we want, without being uncomfortable or awkward around each other. If we want to walk around naked, we walk around naked. If we want to bang, we bang. If we want to watch, we watch. That's the point!"

"What happens if I don't want that? Should I leave the house?"

"Then we won't force you. But you don't have to leave the house. You're staying with us no matter what."

"I don't want to be an inconvenience."

"You're not. You're our friend. You know we love you right?"

Urgh, if only Lisa used the L-word in the way I wanted.

"Wait, why did you say these two things are linked?"

"Oh, well... about that... Denise said it would be better if... I ease you into it before you help me."

"What do you mean by that?"

"Well, I know you're a... virgin..."

"Everyone knows that."

"So Denise thought it won't be nice if your first time is anal sex."

"Uh, right."

"So maybe we can... have regular sex first until we're comfortable with each other."

"So... we're going to have regular sex first?" I asked.

"If you don't mind."

Mind? Having sex with Lisa? There's no parallel universe where I'd mind.

"Uh, tell me again, how do all these link together?" I asked.

"Well, I know you're uncomfortable with physical contact because of your anxiety, so maybe we can help you get used to it first gradually before we start having anal sex."

"And the first step is to walk around naked?"

Lisa nodded. "We can just cuddle without clothes first."

"Before we go into that, are you sure you want to... have sex with me?"

"Why not?" Lisa said in a voice that suggested I was asking a stupid question.

"Because you're with Tony? And Denise? I'm not sure exactly how your relationship works, to be honest."

"Tony and I are not exclusive when it comes to sex. We allow each other to have sex with others. Denise just joins us for sex. She's also our girlfriend."

The way Lisa said it made me wonder if having sex with Denise and having Denise as a girlfriend were two separate things. It sounded like they were. It was confusing as hell.

"And you want me to join as well?"

"If you don't mind."

"You don't mind... having sex with me?" I asked. "What I meant is... are you sexually attracted to me?"

"Oh. Well, I love sex and you're my good friend. I don't have a problem having sex with you."

"There's a big difference between you don't mind and you want to."

"Is this something you're concerned about?" She asked.

"I just want to know what you're thinking," I said.

"Well, sex is fun, enjoyable, and nice. You're my friend. I don't have a problem having sex with my friends."

Even after being friends with Tony, Lisa, and Denise for several years now, I never quite understood the whole 'having sex with friends' thing.

In my upbringing, I was raised with the idea that a man and woman should only have sex with each other, after marriage.

I never bought into that idea of course. I thought of sex too often to accept the idea that I could only have sex with one person, and only after marriage. And my high school was the kind of place where people have sex all the time.

Still, there's a chasm between casual sex and polyamory. The idea that someone could be in a relationship and still had sex with another person was hard to imagine.

But Lisa and Denise pushed the chasm even further by making it a norm to have casual sex with friends. Any good friend was a friend with benefits.

For normal people, hanging out with friends meant talking and bonding. With Lisa and Denise, hanging out included having sex together. Their idea of bonding extended to getting naked together and having physical intimacy.

Then they would end the "hanging out" as normal friends. As though sex between normal friends was normal.

I didn't participate in those "hanging out sessions" whenever I knew it involved people getting naked and touching each other. But it wasn't because of the lack of invitation. As Tony's and Lisa's friend, I was always invited. But it was too intrusive for me, even if my cock liked the idea.

But despite being exposed to the idea, I still didn't understand how it worked.

"So you will have sex with anyone?"

"Not anyone. Only people I like. I like you. We're friends."

I tried not to flinch. Once again, the word 'like' felt like a punch to the gut.

"Don't you have male friends that can help you with... stretching?"

"Well, it took me a long time to get used to the idea of putting something in my ass. I don't have anyone I trust enough to help me stretch it. Except you."

"So I'm the only person that can help you?"

"If you really don't want to, I won't force you, Ken. I'll just try to find someone else."

I didn't like the thought of someone else putting his dick inside Lisa's ass. I rather it be my cock in her ass.

"But I don't know anything about... stretching," I said.

Lisa giggled. "We can figure that out together. It's going to be fun," she said. "Ezra's also going to teach me. She was the one who suggested I start with someone... not as big first."

Ezra was Lisa's elder sister. A senior who came once a week and disappeared in Tony's room whenever she was around. I wasn't sure if Ezra and Lisa did things together. But just the thought of Tony doing two sisters was so unfair. Plus Denise.

How did Tony manage to be able to have sex with three girls at once? I couldn't even manage to have sex with one.

And Ezra wasn't any regular girl. She was the hottest senior. Even hotter than Lisa, objectively speaking.

Along with her youngest sister Elsa, the three sisters were very popular in school. Pretty faces, big tits, and not mean bitches.

"Ken." Lisa snapped her fingers again. "Focus."

"Uh, sorry. What did you say?"

"Are you comfortable with these?" she asked.

"I'm not, but..."

"But you're willing to give it a try?" she asked encouragingly.

Tony was like the impatient father who loved me even though he was frustrated. Lisa was like the patient mother who frequently encouraged me to step out of my comfort zone. This weird dynamic had always worked out for us.

"Uh, I'm fine with you walking around naked. But the sex stuff..."

"You don't want to have sex with me?" she asked.

Of course I want to have sex with Lisa. She was so beautiful. I masturbated to her often. I tried not to, but sometimes the image of her just entered my mind.

"Uh, I... I don't mind, but..."

"You don't feel comfortable having sex in general?"

"Uh, more of the physical touch... you know... my condition."

She nodded. "Don't you think it's time to learn to be comfortable?"

"I'm not sure if I can learn that."

"Why don't we just give it a try? We can help each other out."

Any sane boy would say yes to having sex with Lisa. Or rather no sane boy would ever say no. But I wasn't normal.

Still, it's too good an opportunity to pass up.

"Uh... alright."

"How about we give it a try now?"

"N-now?"

"I can take off my top and we can try cuddling," she said, leaning toward me.

I looked at the gorgeous girl in front of me. Her big blue eyes were soft and encouraging. Her blonde hair flowed down her back. She was casually dressed and yet stunning, a plain black blouse doing little to hide her ample chest and a simple pair of white shorts exposing a lot of creamy thigh as well as her long, long legs. Curvy and slim at the same time. She was a goddess.

I felt blood rushing to my groin and my cock was starting to rise. I immediately crossed my legs away from her to hide my growing erection.

Lisa immediately jumped back a little on the couch, probably thinking I was uncomfortable this close to her. Well, I was, but not in the way she thought.

"Sorry," Lisa said quickly, "I shouldn't have done that."

"Uh, no... I was just... taken by surprise."

"How about we start slow? We can just soak in the hot tub tonight first and ease our way into it."

"Naked?"

"Well, if you want to push yourself a little. But you can just wear swimming shorts first."

"What about you?"

"I'll wear a bikini first."

"First?"

"Why don't we just get comfortable first and then see what happens?"

"Uh... I'll try."

"Say, 9pm?" Lisa suggested.

"I might have work to do tonight," I said. A lie, in case I wanted to back out.

"Well, then join us whenever you're free?" Lisa said. She knew I was lying. I always lied like this whenever I want to avoid social events.

"I might not be able to finish by tonight."

"Just promise me you'll try to make it if you can?"

"I... I'll try."

----

I spent the entire day fretting over what to do.

I had never once joined them in the hot tub on the rooftop. Even though the tub could comfortably fit six people, or up to eight if everyone sat shoulder to shoulder, the thought of being in close proximity with others freaked me out.

Especially with half-naked people. I wasn't uncomfortable with nudity per se. It was more of an intimacy thing. My mind equated nudity with intimacy. And intimacy made me all weird up.

My mind was weird, making up its weird rules without much logic. Going to the beach and seeing semi-naked people was fine, but sitting with a bikini girl on the same towel was not.

Watching porn was fine. But seeing Lisa walking around in nothing but panties? It felt intimate. Boundaries crossed. I had a big thing with boundaries. Even when I could be with naked girls. My mind didn't like that even if my body did.

It wasn't like I wanted this.

I wanted to be confident and outgoing like Tony. I wanted to be having a lot of sex like Tony. And I really really wanted to have sex with Lisa.

But I felt uncomfortable with physical contact. When in close proximity with others, it felt like bugs crawling up my skin. And once I started to feel uncomfortable, my body and mind tensed up. I wanted to run away. I usually did.

By 8:53pm, I was spiraling.

I was already dressed in swimming shorts but in the last thirty minutes, I changed my mind every few seconds.

Aside from Lisa's weird request, I knew this was the opportunity for me to learn to be more comfortable.

Lisa was the best person to help me. She had helped me to be able to talk to others like a normal human being. She had helped me to be comfortable looking at her in the eye when I talked to others. She had helped me to resist the urge to run away at the slight discomfort. Mostly.

And now Lisa was offering to have sex with me. I could always refuse, but then Lisa would find someone else and the offer would be gone forever.

Without Lisa's help, I might never get laid. And I want to get laid. Especially with Lisa.

And I rather do butt stuff with Lisa than let another guy do butt stuff with her.