A Reluctant Sex Instructor Ch. 01-02

So at 8:57pm, I forced myself out of the room and walked up the stairs.

Just before I reached the rooftop, I heard them talking about me. I paused and listened.

"Do you think Ken will go for it?" Lisa asked.

"You're Ken-Whisperer," Tony said. "You tell me."

"Thinking about this now, I'm not sure if this is a good idea," Lisa said.

"Isn't it a bit too late for that?" Denise asked.

"What if he starts having feelings for me?" Lisa said.

"Girl," Denise said, "he's already in love with you."

"He's not!" Lisa snapped. "How many times do I have to say this? We're just very good friends."

"You're in denial," Denise said. "You do know the way he looks at you right?"

"That's because he's comfortable with me," Lisa replied.

"Because he likes you," Denise said.

"Because I'm nice to him!" Lisa yelled.

"What do you think, Tony?" Denise asked.

"It doesn't matter much to me. I'm not the jealous type. I don't have an issue if he does. It's not like he's going to steal my girlfriend away," Tony said. "But for argument's sake, so what if he's in love with you?"

"I don't want to have to reject him," Lisa said.

Ouch. I knew she would never go for me, but hearing it like that hurt a lot.

"Then don't," Tony said. "It's not like we're monogamous or anything."

Hearing Tony didn't have a problem with me falling in love with his girlfriend was... strangely comforting.

"Even if we assume I like him that way, he may not be open to non-monogamy," Lisa said. "You should know best what kind of family he came from."

"I do, but he's not as traditional as his family," Tony said. "Especially if he agrees to have anal sex with you."

Traditional was putting it mildly. But Tony knew exactly what my family was and knew my thoughts on my family better than everyone else, even Lisa.

"There's a big difference between sodomy and non-monogamy," Lisa said.

"What's the difference?" Denise said.

They all laughed.

"Do you really think he's already in love with me?" Lisa asked.

"He's definitely infatuated with you," Denise said.

"Maybe I shouldn't be his first..." Lisa said.

Shit. Was I too late? Should I have agreed earlier? I really want to have sex with Lisa.

"I could help," Denise said.

"You?" Lisa scoffed. "You'll scare him away."

"Hey, I've taken several virginities before," Denise replied. "And they all came out fine. A few of them more than fine."

They laughed again.

"That's because they are dying to lose their virginities," Lisa said. "They would do it at first the opportunity. And they did."

"You think Ken's different?" Denise asked. "If you just drop your panties in front of him and ask him to have sex with you, you think he won't go for it?"

"He didn't even want me to take off my top just now," Lisa said. "I think he would prefer to take it slow, maybe a little romance first."

"Why don't you just ask him?" Tony said. "Much easier than going around in circles talking about it right?"

"He's not as confident as you, Tony," Lisa said.

"But he tells you everything right?" Tony said.

"I don't think he tells me everything," Lisa said. "Just more than most people."

"Before we continue talking about this," Denise said, "is he even joining us here? If not, I rather go to the room and fuck."

"I'll go check," Lisa said.

I quickly crept back down the stairs and pretended to walk back up, slowly. By the time I was halfway up the stairs again, Lisa appeared at the top in a bathrobe.

"There you are," Lisa said. "We're wondering whether you're going to join us."

I stopped and looked up. Her long, creamy legs were mouth-watering. "Sorry, I was uh..."

"Don't need to apologize," Lisa said. "Come join us." She smiled at me.

On the rooftop, Tony and Denise were in the hot tub. Tony was topless, but I guessed (and hoped) he wore shorts. It was different to look at him and not be jealous. Broad shoulders and wide chest, with huge biceps. Along with the textbook definition of 'six-pack abs.'

Even in a hot tub, Tony had his usual slick-back hair like a mafia boss.

Denise was in a tiny purple bikini that barely covered her ample breasts. Though her platinum-blonde hair shielded half of my view. She flicked her hair back when she saw me looking and pushed out her chest. She winked.

Denise was tall, slender, and model-like. With very big and round tits, almost too big for her slim frame. If not for the fact I knew her since high school, I'd have thought her tits were fake. They suspended in the air as though they decided that the rules of gravity didn't apply to them.

On top of being one of the hottest girls in school, she was also a big flirt. Slutty and sexually aggressive. I didn't have a problem with that except for the fact she liked to tease and embarrassed me. Even after frequently getting scolded by Lisa.

Living in the same house as her was a nightmare. She frequently wore crop tops that exposed her midriff without a bra, and took every opportunity to brush her tits against me.

Whenever Lisa admonished her for teasing me, Denise would reply it wasn't teasing, it was an invitation. Though I was certain she didn't want to have sex with me. Girls like her didn't want to have sex with guys like me.

"Come in dude," Tony said, gesturing opposite him. Denise sat close beside him with their shoulders touching.

I took the furthest spot away from them and went in. I got to admit, the warm water felt nice on my skin. It was rather comforting. Perhaps I could get used to this.

From the corner of my eye, I could see Lisa removing her robe. I stared down and tried not to peek.

Then Lisa climbed into the tub and her breasts came into view beside me, begging me to look at them.

Like Denise's, Lisa's bikini was tiny. Just two small white triangles covering the nipple areas. The kind of bikini not allowed in public.

I looked up at her and saw she had caught me staring. She gave me a warm smile and I immediately looked away.

I heard Denise chuckle.

"Ken, you can look at me, you know, I don't mind," Lisa said.

I looked back at Lisa's face. She sat so close to me that I felt a rising urge to move away. But I resisted.

Lisa smiled. "I meant you can look at my tits if you want."

"Uh..." I glanced down at her tits then quickly back up at her face again. She was as good as naked. Shit, I was getting aroused.

"How about we play a little game?" Lisa said.

"What game?" I asked, panicking a little now.

"For the remainder of tonight, you can stare at our tits all you like," Lisa said.

"Uh..." I glanced down at her tits again. Her bikini top were nothing more than strings. I looked back up to her face.

"You like looking at our tits right?" Lisa asked.

I swallowed hard. "They are... uh... very nice."

Denise laughed. "Gosh, he's so cute, I want to bring him to bed and rape him."

"Denise!" Lisa said in an admonishing tone.

"Sorry," Denise said, trying to hide her laughter.

"Anyway," Lisa said. "You can look at our tits whenever you want."

"Uh, thanks," I blurted out. Denise laughed again. Shit. I said thanks. Was that weird? That must be weird.

"Just treat this like practice. You just need more practice," Lisa said. "We've talked about this."

"Uh, right," I managed.

So the practice today was to be able to comfortably stare at the girls' tits.

Lisa had taken it upon herself to help me overcome my awkwardness with practice. For a period of time, she would ask me to stare into her eyes for one minute every day, until I could withstand not averting my gaze. Then the practice would progress to two minutes, three minutes, five minutes.

Another practice she made me do was to walk up to a random girl, comment 'nice shoes,' look her in the eye, smile, then walk away. It had taken me a long time to get comfortable with that. I still wasn't. But now I could at least pretend to be like a normal human being. I was surprised by how effective Lisa's practices were.

"Do you want champagne?" Lisa asked.

"I just took Benzo. Not a good idea to take it with alcohol," I said.

But even if I hadn't taken medication I stayed away from alcohol as much as possible. After my favorite uncle died in a car accident while drunk driving when I was young, I had vowed not to touch alcohol.

"Just a little is fine. We'll take care of you," Lisa said. She poured me a glass and I took it reluctantly.

"What should we cheers to?" Lisa asked.

"To our tits," Denise said. Lisa shot her a disapproving look.

"What?" Denise asked, scandalized. "It's not inappropriate right?"

They laughed. I couldn't help but chuckle a little as well.

For the next hour or so, we just talked about the usual stuff. College, friends, high school, things of no consequence. Or rather, they talked while I mostly listened. Like I tended to do whenever I'm with them. Once in a while, Lisa would pull me into the conversation.

Between the Benzo, the alcohol, and the hot tub, I got to admit I was having a good time. It was one of the better nights I had.

I didn't stare at their tits, but I didn't deliberately avoid my gaze either. I blamed it on the alcohol, though I did like looking at their tits. Very much.

It was hard not to like. They were very fine sets of tits.

Besides, I needed more practice.

----

"Dude, you alright?" Tony asked when it was just the two of us in the tub.

Lisa and Denise had gone to the pool to cool off. I watched them standing at the end furthest end and giggling among themselves. Their breasts shook along with their bodies.

Perhaps I could get used to this. With enough practice.

I turned to Tony. "I think I'm buzzed."

Tony chuckled. "That's a good look on you. You should join us more often, dude."

"One step at a time," I replied, not exactly sure what I was talking about.

"Have you thought of what Lisa asked?"

"You meant the... butt stuff?"

Tony chuckled again. "Yeah, the butt stuff."

"Uh... you're fine with that?"

"Dude, I suggested it," he said.

"You really don't mind me having sex with your girlfriend?" I asked.

"Do you?" Tony asked.

"Uh..." Shit. I couldn't think straight. What was the right answer here? Would Tony mind If I confess I want to have sex with his girlfriend? What if this was a test and he got angry?

"I know how you feel about Lisa," Tony said. "Ever since we became friends."

Shit. I needed to think. "Was it... really that obvious?"

"I didn't go after her at first out of respect for you dude. But when I saw you were not going to do anything, I made my move."

"Uh... it's not like she liked me anyway."

"Maybe she did," Tony said. "But you missed out on the chance to find out."

"She said..." I stopped myself. Shit, I almost confessed to eavesdropping on them.

"For the record, I know you overheard us earlier."

"You... knew?" I asked.

Tony nodded. "I saw you. Again, I didn't say anything out of respect for you, dude."

I was touched by his loyalty. He knew I liked Lisa and he knew I was listening but he acted like he didn't know. He had always been a great bro. But this was the bro-est of the bro-code.

And my bro even wanted me to fuck his girlfriend. Which I now suspected was more for my benefit than for Lisa's. I wouldn't be surprised if he orchestrated the whole thing just so I could be intimate with Lisa. So that I could get laid. So that I could learn to be comfortable with physical intimacy.

What kind of bro did that?

"Uh... thanks. And sorry, I shouldn't have done that."

Tony waved his hand. "Ken, you need to start learning that in life, you need to work towards what you want. You can't always expect others to spoon-feed you all the time."

I felt like a kid receiving words of wisdom from his father. Tony was always introspective and serious when drunk.

It was probably the alcohol effect, but I decided to shoot back.

"Not everyone got it easy like you."

"Maybe. But I worked at it too."

"Since when?"

"Remember the first year in high school when I started to put on muscle?"

I nodded. He went from a scrawny kid to looking like a gladiator in just a few months.

"Call it genetics or hormones if you like," Tony said, "but I spent a few hours in the gym every day so that nobody messed with me ever again. And so that I could protect my friend."

I was deeply touched. The affection and nostalgia hit me like an animal tranquilizer taking out an elephant.

"So the moral of the story is I should start going to the gym?" I joked.

"Maybe," Ken said, looking at me seriously. "I'm giving you the opportunity to get what you want. You're no longer living under the oppressive rule of your parents. You can have the opportunity to get over your fears. You can lose your virginity and have sex with Lisa if you want. You may have your issues, but you can't say you don't have the opportunity to get through them."

"Uh..." I was lost for words at the generosity and affection of my best friend.

"I'm not going to keep treating you with kid gloves, dude," Tony said. "You're my best friend and I'll always look out for you. But I'm not going to coddle you anymore, Ken. If you want something, I'll support you. But I'm not going to keep trying to be patient with you like Lisa."

Coddle? That was fucking harsh. But I knew what he was saying. And I knew he meant well. "I understand where you're coming from."

Tony jerked his head towards the girls. I turned and looked in the same direction.

They were topless. Their bikini tops untied and thrown carelessly on the floor next to them. A bundle of white and purple strings bundled together. Looking at their naked breasts in all their glory, and they were glorious. I was... enthralled.

"I'm going to go over and suggest we play Chicken Fight," Tony said, pulling my attention back to him. "You can decide whether you want to join us."

With that, Tony stood up, got out of the tub and started to walk toward the topless girls.

Then he stopped and turned back. His expression softened a little.

"Why don't you just join us?" Tony said in a kind voice. "If you don't like it, at least you know. But you won't regret for not giving it a try."

He turned and walked towards the topless girls again.

This was a test. A test to see if I would follow his advice. A test to see if I would take the opportunity in front of me instead of running away.

Chicken Fight meant the girls would be sitting on our shoulders. Which meant their legs would be around my neck. Which meant a lot of physical contacts. Which meant I would probably die from sheer discomfort.

On any other day, I would run away. I was a wimp.

But I didn't want to be a wimp anymore.

Besides the offer to have sex with Lisa, I also didn't want to let my friends down. Everything Tony said was true. They had treated me with kid gloves. Lisa had to protect me most of the time. What kind of girls did that? And what kind of guys allowed girls to do that?

Girls definitely don't like wimpy guys.

So I drank the rest of my champagne, got out of the tub, and started walking toward them. My courage faltered a little when Lisa beamed at me with approval. She was so gorgeous. Even more gorgeous naked.

But I carried on.

And it was a good thing I did. Because it was the first time in my life I found out how much I enjoyed the female naked flesh against mine.

****

Chapter 2: The First Time

****

After trying to avoid eye contact and avoid staring at their naked tits, I mostly forgot about the topless girls once we started playing Chicken Fight.

Mostly.

We started with Lisa on my shoulder and Denise on Tony's.

"Ken..." Lisa said, dragging my name, as she pushed her crotch against the back of my neck. "Hold me tighter!"

We had a few false starts because Lisa kept falling off my shoulders before the fight even began.

Having a girl's legs wrapping around my shoulders was stretching my comfort zone. I was acutely aware of how Lisa's pussy and my neck were only separated by a thin material. It didn't help whenever I thought of how tiny her white bikini thong was.

It was the furthest I've ever gone with a girl.

"Grab my legs," Lisa shouted above me.

"I'm already grabbing your legs," I shouted back.

"Not my ankles. My thighs." Lisa said, a little frustrated now.

I hesitated, then reluctantly complied, gripping her kneecaps, which I thought was the most innocent in this situation.

Somehow, Lisa was able to reach down and move my hands up to her bare thighs. "Hold me tight."

I did, feeling her creamy thighs for the first time. Interestingly, the experience wasn't as uncomfortable as I thought it would be. It was actually enjoyable.

I even forgot to feel anxious.

But I forgot all about that quickly when Tony and Denise approached and the fight started.

We went at it for several rounds. Then we switched over. I lost every time. Even though Tony was the one supporting the girls, he was too strong, too tall, and too fast.

Tony's athleticism extended even in the pool. He could flank me faster than I could turn in the water. Even with a girl on top of him.

Well, at least I did have fun.

"One more?" Lisa asked.

"I choose Tony!" Denise said quickly. I couldn't blame her. I was no match for Tony.

"How about Tony and Ken?" Lisa suggested.

"Girl, we're gonna get our ass raped..." Denise said. "Unless that's the whole idea."

They laughed. I laughed too. The alcohol and benzo were working.

"How about we make the game more interesting?" Tony suggested. "Punishment for the losers."

"I was kidding about getting my ass raped, Tony," Denise said. "Especially not by you."

"Oh!" Lisa said. "How about the losers have to strip naked for the rest of the night!"

"If you want me to get naked, you can just ask." Denise smirked.

Lisa shot her a look. She turned back to me. "Shall we?"

"Uh..." I didn't know which was worse. Seeing the girls naked or being naked myself.

Well, of course I wanted to see the girls naked. But I was already having too much stimulation.

Before I could answer, Tony swam towards me, got underwater, went between my legs, and head-butted me in the groin, pushing me up into the air with his shoulders. I hung on to his head for dear life. It was a wonder I didn't get thrown off.

Well, too late to say no now.

Though Lisa had a curvier body and bigger frame than Denise, Denise was taller. So Denise grudgingly allowed Lisa on her shoulders.

In a normal chicken fight, the two people on top would wrestle with their hands and try to bring the other one down. But Tony being Tony, he'd rather create a situation where there was no contest at all.

Tony's strategy was always the same. He would move towards the opponent, then side-step to their flank or get behind them if he could, while the one on top of him could just push the other pair over, making them lose balance. To Tony, it wasn't a game, it was a competition.

This strategy could only work because Tony was strong and fast enough. He moved faster in water than I moved on land.

Tony was a true pro in Chicken Fight. I supposed he must have a lot of practice with a pool in his mansion.

But the first two times, I couldn't take advantage of Tony's superhuman speed. When we got behind Denise and Lisa, I froze, missing the opportunity. Tony had to move back and try again.

The sight of two topless girls with their bare tits hanging in front of me... it was too much. And when we got behind the girls, Lisa's thong was so small at the back she might as be naked. I could easily push her from behind and topple them, but I didn't dare touch her naked flesh.

I blamed it on the alcohol but I wasn't paying attention. Or rather, I was paying attention to the wrong thing.

"Dude," Tony said from below. "I don't know about you, but I rather see the girls naked."