02

An awkward teenage virgin was asked to have anal sex with his crush. But first, he needed to be comfortable living with naked girls and learn to enjoy regular sex. Somehow, he eventually became known as a sex instructor on campus.

AUTHOR'S NOTE:

This is a multi-chapter story of how a shy teenage virgin eventually became known as an anal sex instructor. But there's also a lot of vaginal sex. Along with threesomes, orgies and college sex parties.

Lisa made sure of that.

This story includes a lot nudity, harem, group sex, lesbianism, anal sex and polyamorous relationships. If any of that bothers you, find another story to read.

All characters in the story are eighteen and above.

(By the way, I was medically diagnosed as a wimp and certifiable weird. Though I did get less wimpier the more girls I had sex with. Even my doctor was impressed. So don't be too hard on me at the start, deal?")

****

- PROLOGUE -

****

"Oh fuck..." Alena moaned as my mushroom head disappeared between her butt cheeks.

I could never get used to the sight of watching my cock entering a girl for the first time.

"Does it hurt?" I asked.

"No... push in some more..." the nineteen-year-old college girl encouraged.

I compiled, gripping the redhead's hip and thrusting slowly until my cock went in another half an inch. Then I stopped, letting her get used to my cock in her ass.

Spooning on our sides like this wasn't ideal. It was harder to control my thrust. But it was the best position for first-time anal sex.

When I felt no resistance from her, I went in another half an inch, then another. I stopped whenever she tensed up, then continued on when she relaxed.

Until I finally bottomed out. It was unbelievably tight. Okay, not that unbelievable, since every girl's ass was always tight, especially for the first time. Sometimes a little too tight, especially when her butt's clenching my cock.

Though not unpleasant. It was the opposite of unpleasant. I supposed this was how a cock ring would feel like, with the ring moving down my shaft as I pushed deeper into her ass.

Except unlike a cock ring, her butt could clench. At the moment, it felt like my cock was going to break from getting squeezed too hard.

Has a cock ever break during anal sex? I had no idea. I hoped not. I didn't even want to fuck Alena's ass in the first place.

I was only doing this as a favor after all.

I tried to calm down before my anxiety took over. Having stupid thoughts like that... was stupid. I took a moment to breathe. Despite me not wanting to do this in the first place, I might as well try to enjoy this.

I focused my thoughts on what I enjoyed about fucking a pretty girl like Alena. Alena was really hot. The ratio of guys wanting to fuck her and guys that actually fuck her was probably a few hundred to one. So I was the only lucky few that could fuck her. And the first to fuck her ass.

Staring into the back of her ginger hair, I tried to enjoy the sensation of feeling her slender back against my chest, her perky butt against my pelvis, and her slim legs against my thigh.

Most importantly, I focused on how pleasurable it was to be inside this peachy ass. My cock. In her ass.

I never liked thinking like this. It was rude. But for the moment, it seemed to help me get into the right mood.

"Good?" Lisbon asked.

The petite college girl sat cross-legged in front of Alena. I glanced at her naked body. Her modest breasts looked so perky. I've been wanting to touch them since she took off her bra.

I'm definitely in the right mood now.

"I feel... very stretched," Alena said.

Lisa giggled, her breasts bounced a little as her body shook. "That's the whole idea."

Even after seeing Lisa's tits every day, it still made my heart flutter a little whenever I looked at her naked.

I took a deep breath and willed myself to focus on the girl in front of me. It wasn't right to lust after another girl when my cock was already in her butt.

"Let me know when you're ready," I whispered into Alena's ear.

"Give me a while to... get used to it..." Alena panted. "It feels different from having a plug up my ass."

"But much better right?" Lisa gave a salacious grin. She should know. Her ass was the first one I'd fucked.

"You weren't kidding," Alena said. "I feel like I'm going to come just from this."

"Oh!" Lisa exclaimed. "You should try with a vibrator on your clit! It's the best feeling in the world when you come with him in your ass."

"Um..." I interjected quickly before they started getting funny ideas. "How about we take it one step at a time?"

Lisa giggled. "Well, you're the expert."

----

It still felt weird to be called an expert.

I was by no means an expert. Even after fucking some of the hottest college girls' butts to the point where I'm starting to lose count, simply talking to girls alone still made me anxious.

I was a wimp. Though I did have good reasons for that.

But despite my wimpiness, I still somehow became known on campus as the 'go-to guy' to help girls enjoy a cock in their butts.

There were even the weird occurrences of guys asking me to help their girlfriends fall in love with anal sex. So that they could eventually enjoy their girlfriends' butts themselves.

They said I'd be doing them a huge favor. They'd owe me one. Just for fucking their girlfriends' asses.

I supposed when a guy really wanted his girlfriend to be addicted to anal sex, he would do anything to get her hooked on it. Even if it was not his cock she got addicted to in the first place.

The reason how I became known as the 'anal sex expert' was weird.

It wasn't because I was the best-looking guy on the campus, or had the hottest body, or had a monster cock like Tony.

On the contrary, it was precisely because my dick wasn't big at all. Though it happened to be the right size. The right shape and size for anal sex. At least that's what they all told me. Making college girls begging me to fuck their butts.

It was the kind of thing that I thought only existed in porn.

It seemed ridiculous to think that merely six months ago, at the start of the school year, I was still a virgin.

I hadn't even held a girl's hand before then. I had a crippling, severe anxiety disorder since young that made me uncomfortably anxious most of the time. Especially around pretty girls like Alena.

But somehow, my debilitating mental condition also made girls like having sex with me. Even when we're not doing butt stuff.

These two weaknesses became my strength as a sex instructor.

For any girls who wanted to have anal sex with me, Lisa also made sure those girls allowed me into their vaginas first.

And it must be bareback sex, because Lisa hated condoms, even if her vagina wasn't the one receiving my cock. With me coming inside them at least three times before I'd penetrate their asses.

Or so Lisa proclaimed.

It was a rule Lisa set. And a rule that all the girls obeyed.

Because of that, I had a long queue of girls waiting to have sex with me. Just so I'd fuck their butts.

Worse, there's also a new rumor going around that I'm the best guy to help girls lose their virginities. Any virginities.

"Any hole you want to learn to enjoy having a cock in it."

I'm pretty sure it was Denise who started it. I suspected she enjoyed tormenting me like this.

Truth be told, I didn't enjoy casual sex. Being naked with a stranger freaked me out. But I was getting better at it.

It all began at the start of my first year in college when my best friend, Tony Kingsley, asked me to live with him. His family was ultra-wealthy and rented a two-story house, insisting that I stayed with him rent-free. Along with Lisa and Denise.

Lisa was Tony's girlfriend while Denise was Lisa's best friend. Though the three of them frequently had sex together, in kind of a trouple, polyamorous relationship that took me a long time to understand.

There were also other girls who frequently joined them in the bedroom. Tony was the luckiest guy in the world.

If he wasn't my best friend, I would have hated him.

Tony was tall, had a pretty boy face, jacked body, and filthy rich parents. He was smooth, charismatic, and confident. A chick magnet that started in high school.

Just to complete the cliché, Tony was also blond with piercing blue eyes. Or maybe the cliché started with Tony whenever people described a beautiful guy. A Greek sculptor would be jealous.

In high school, Tony's nickname was 'Mr King.' I won't be surprised if he was actually royalty.

Whereas I was a nerd. With anxiety so severe I had to take Benzo every day. Along with a host of other mental conditions. I couldn't even look girls directly in the eye whenever I'm talking to them.

Except Lisa Kelton.

She was the girl I wanted to be with the most in this world. I'd rather have sex with her than casual sex with a new girl every day.

Which was why I couldn't refuse her when she first came to me with an unusual request after living two weeks in the same house.

****

Chapter 1: The Request

****

- August, 2017 -

"This is not a joke right?" I asked.

"It's not," Lisa said firmly. She pulled her honey-blonde hair over her ear and waited for that statement to sink in.

"You want me to... fuck your ass?" I asked.

Anyone who meets Lisa and Denise for the first time would be shocked by how casual they were talking about sex. It was like they lived in a porn movie.

Denise could walk up to a random stranger and say, 'nice tits' as though Denise was complimenting her shoes. Lisa could talk about her sex life within five minutes of meeting someone new, just like how guys would talk about their favorite sports.

Sex was always their favorite topic even in high school. They could casually ask someone 'Did you have a good fuck last night?' as though they were asking 'Did you do your homework last night?' with a straight face.

After being friends with them for years, I was used to it. Mostly.

But this request was outside the comfortable range of what I was used to.

"That's right, Ken," Lisa said.

I looked into her beautiful green eyes to make sure she wasn't kidding. My favorite eyes in the world. But I was the worst person to understand social cues.

"And Tony's fine with it?" I asked.

Who in the world would be comfortable with asking his best friend to fuck his girlfriend in the ass?

I know Tony and Lisa had a special kind of relationship that included inviting other girls to have sex with them. But I didn't know Tony was open to having other guys fucking his girlfriend.

Especially her ass.

"Yup," Lisa said casually. "He suggested it."

"He did?" I asked, not quite believing what I heard.

Tony was always generous towards me, the kind of generosity that always made me cringe.

But I didn't know Tony was this generous.

"Maybe I should start at the beginning," Lisa wondered out loud.

"I think you should," I agreed.

"So Tony and I have been trying anal sex for a while..."

In situations like this, I'd have said, 'Too Much Info'. I never like hearing about their sex lives.

But she did ask me to fuck her ass.

"Okay..." I managed.

"But we can't seem to get it to fit..."

"By 'it' you meant..."

"Tony's cock," Lisa said. "It's too big."

"Uh... right." I knew what she was talking about.

Even if sharing gym class with Tony for the past three years hadn't made me know of that fact, girls in high school always talked about Tony's monster cock. It was the only thing they ever wanted to talk about.

Another reason why I'd love to hate Tony.

"So we're hoping you can help me to get used to it," Lisa said simply, as though that explained everything.

"How's... how's that going to work?" I asked cautiously.

"You can help me stretch it first."

"By 'it' you meant your..."

"My butt," Lisa said. She tilted her hip and indicated her bottom for emphasis. It was a bottom I had lusted after for several years.

"Uh, right..."

"Do you think you can help us... help me with that?" Lisa asked cautiously.

Lisa played on my weak spot. She knew I'd avoid saying no to her whenever I could help it.

"You know this is a really weird request right?" I said.

"It's a little unusual, I admit," Lisa confessed.

"A little?" I asked, incredulous. "But why me?"

"Because Tony trusts you, of course. We all do."

"Is that the only reason?"

"Um, well... how do I put this..." Lisa said hesitantly.

"Because I've a small cock?"

I didn't exactly think I had a small cock. It was average. I was neither proud nor ashamed of it. But compared to Tony's, mine was tiny. Hell, compared to his, everyone's was tiny.

"No!" Lisa said quickly, "Um, just maybe... not... as big as Tony."

"This is not payback for the other night, right? An elaborate prank to get back at me?"

"No, no!" Lisa said quickly. "I already told you I don't have a problem with that! I never did!"

"Then what's the meeting earlier about?" I asked, still suspicious about the meeting before this talk with Lisa.

I was invited to have a meeting with Tony, Lisa, and Denise in the living room. A formal house meeting. I thought I was getting kicked out of the house for looking at Lisa walking around naked.

My nerves were still frayed thinking about the house meeting earlier.

----

"Am I getting kicked out of the house?" I asked, half-joking, half not, as soon as I sat down with them in the living room.

When Tony asked me to live together with his girlfriend and his girlfriend's best friend, I thought it was a bad idea.

Even in high school, I knew they had a huge amount of sex. Whenever we had study sessions in Tony's mansion, Tony and Lisa would often disappear to have sex several times a day. Then they would come back half-dressed, hair messed up, and continued to study with me as though nothing happened. An hour later, the same thing happened again.

I also knew Denise often joined them. They didn't exactly try to hide it. Denise also frequently brought a friend to join Tony and Lisa in bed. Then the three girls would appear looking like they had the best time of their lives.

I always wondered how that worked. Having sex with three girls at once looked and sounded exciting. The stuff of fantasy. But in reality? It felt impossible.

I didn't exactly mind that they were always having sex. It was their business. And they were my best friends. Good for Tony. But it only became a problem for me when I had to witness it every day.

I found out exactly how bad an idea it was on the night we moved into this house.

The house was four blocks from campus with four bedrooms. Downstairs had a living room, kitchen, bathroom, and two bedrooms. Upstairs had two more bedrooms and a bathroom. The rooftop was flat, with a small pool and a hot tub. I was pretty sure the owner designed it to be a party house. I was also pretty sure this was the main reason Tony wanted to live there.

Tony and I took the room downstairs. Lisa and Denise took the rooms upstairs. But with Tony's room being the biggest, Lisa and Denise frequently had sex with him in his. Almost every day. Sometimes with an extra girl.

Right from the first night, I could hear them having sex. With only a thin wall separating my room and Tony's, I could hear everything. All the moans and groans. All the smacking of flesh on flesh. And all the dirty talks that Denise liked during sex.

After the first night, I begged them to allow me to take the bedroom upstairs instead. But Lisa and Denise wanted the second floor to be the girls' floor. Something about easier to share everything when their rooms were side by side.

Another thing they liked to do was walking into the kitchen whenever they took a break during sex. Stark naked. The first time I caught a glimpse of their naked butts when I opened my door, I shut the door quickly.

When Tony tried to apologize to me the next day, I told him it was fine. It was his house, his rules. No matter how uncomfortable I was.

Since then, whenever they started having sex, I mostly stayed in my room with a headset on. Or hid out on the rooftop until I knew they were done.

Then an incident happened two nights ago. At two in the morning, after I was very certain they were all asleep after a bout of very long sex, I came out of the room only to find myself face-to-face with a naked Lisa.

It was the first time she was fully nude in front of me. I had seen her in various states of undress before, but never as naked as the day she was born. And I had never seen her bare pussy before.

Until that night.

Instinctively, I ogled at her body, checking out every curve. I stared at her bare breasts and pussy for god knows how long, mesmerized. When I finally regained my senses and looked her in the eye, she was looking at me, very amused.

Then the panic struck and I yelled an apology and dashed back into my room.

So when Tony called this meeting, I thought I was getting kicked out for ogling his girlfriend.

"Woah dude, nobody's getting kicked out!" Tony said quickly.

"I still feel like I'm getting ganged somehow," I said, looking at my best friend, then at his girlfriend. My anxiety was already starting to rise.

"Dude, chill the fuck out," Tony said. "And tone down on the passive-aggressiveness, will ya?"

Lisa frowned and turned to her boyfriend, "Tony, maybe I should talk to Ken alone?"

"I thought the whole point of coming to college and living together like this was so that we can start behaving like proper adults," Tony said frustratingly.

"Okay, okay, this is not going as well as I expect it to be," Lisa said.

"How did you expect this to go?" I asked, now failing to hide the panic in my voice.

"Dude, stop that!" Tony said.

"Tony!" Lisa yelled, "Just let me speak, will you?"

"Is this about the other night?" I asked nervously. "It won't happen again."

"That's what we wanted to talk to you about, dude," Tony said.

"I'll just stay in my room from now on if it helps," I said quickly.

"No!" Lisa said quickly, "You don't have to do that... look, can you try to hold your anxiety together until I finish saying what I want to say? It's nothing bad, I promise."

I looked at Lisa, then at Tony, then at Denise who had remained quiet the entire time, then back at Lisa and nodded.

"First, let me say again I'm not mad about the other night," Lisa said. "We live together. It happened. It was my fault for walking around naked like that."

"It's not your fault that I stared at you like a piece of meat," I said guiltily.

"Technically it was her fault," Denise decided to chip in.

"Wait, how's that my fault?" Lisa asked.

"You're hot. He's a virgin who had never seen a naked girl," Denise explained matter-of-factly.

"Denise!" Lisa yelled. "Don't be rude!"

"How's that rude?" Denise said. "It's just a fact."

"Uh, so this meeting is about that night, right?" I asked. My anxiety was now leaping into the uncomfortable zone. Just a few steps away from a panic attack.

"No... well, in a way, yes," Lisa said.

"So it IS about the other night?" I asked again.

"Dude," Tony said, annoyed. "Alright, it is about the other night. Move on."

Despite being best friends, there's a limit to how much Tony's alpha male side could tolerate my wimpy ass.

I often wondered why Tony put up with me. Not just put up, but kept me as his best friend.

We were nothing alike. He was the kind of guy everyone wanted to be friends with. I was the kind of guy no one wanted to be friends with.

He was fun, spontaneous, and easy to talk to. I was a nerd, who couldn't talk to anyone.

He was good-looking, I was not. He had a model-like body. I did not. He was rich. I was not.

All the girls wanted to be with him. No girls even wanted to talk to me.