My Best Friend Alice

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With Alice, practice makes perfect.
8.2k words
4.8
37.1k
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Part 1 of the 2 part series

Updated 09/28/2023
Created 09/14/2023
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Being young is the easy part, there are no rules to follow and all you ever want to do was play, have fun and enjoy yourself.

That's when I met Alice, my best friend. From the age of five, we would play together all day, everyday. I remember looking forward to school, just so that I could see her again. We had so much fun together.

It's only when we started to get older, did people start lumbering us with rules and expectations, telling you what you can and cannot do.

It was always a binary choice, girls should play with girls and boys should play with boys. The other girls would go to Alice and say "You can't play Sean, he's a boy." and like wise the boys would come to me and say "but Alice is a girl, she can't do boy stuff like us."

We didn't care, It didn't matter to Alice and I, it only made our bond stronger.

As we grew older the other kids teased us, saying we were girlfriend and boyfriend or that we were weird (that's kids for you, if it's different, expect to be called out on it), which we always denied.

As we reached our teens and started puberty, it became evident our bodies were changing. Alice was developing into a beautiful young woman and I, well was a hot mess to be honest. I got taller, my voice got deeper and I got hair everywhere. I felt like a bag of elbow's I was so awkward. The boners came every five minutes, I was constantly having to put my hands in my pockets to save my embarrassment.

But despite all this, Alice and I had never been closer. There were no secrets between us, we would talk about everything and usually nothing was off limits.

We once spent the whole afternoon talking about her periods. I even secretly stashed some pads in my school bag for her in case she ever ran out.

We had now both turned eighteen and were in the final year of school. I went to her house after school as I sometimes did and we'd sit on her bed and chat for hours.

## Here's where our story begins...

"I think Kimberly is going to ask me out."

"How do you know that?"

"Ryan spoke with Alexa, she said Kim fancies me and was thinking of asking me out."

"Oh really. I like Kim she seems nice. Are you going to say yes?"

"I think so."

"You think? You should totally go for it."

"I do want to say yes, but I'm worried."

"Worried about what?"

"You know, the stuff you do on dates."

"Oh."

"I don't really have, you know the experience in that department."

"We've all got to start somewhere I guess."

"I know, but I've never even kissed a girl that wasn't my mother or grandma."

Alice could see this was really bugging me.

"I can't believe I'm going to suggest this, but you could kiss me... for practice I mean."

I scanned her face for sarcasm, it looked genuine.

"No way, I can't kiss you, you're like my best friend, it would be like kissing a sister or something, it would be weird."

"Fine, fine, I was only trying to help. Maybe you should call up Ryan and practice with him." She said visibly annoyed and with a hint of jealously.

Alice didn't really like my guy friends, probably because they never accepted her as I did.

"No wait, I'm sorry. I just meant, I don't want it to get weird between us."

"You worry too much, nothing's going to happen. You think we'll kiss and I'll suddenly fall in love with you and be like oh Sean where have you been all my life, Marry mee!" She said mockingly, making kissing noises with her lips.

"Yeah right. You wish." I said and playfully barged into her.

Alice scooched closer to me on the bed.

"Ok then Sean, kiss me."

I looked at her face waiting expectantly.

"Fine!"

I leaned forward, hesitating for a moment, then pecked her on the cheek.

"Uh, what was that Sean? I'm not your mother. Try again and this time on the lips."

I was feeling really awkward about this, but it didn't seem to be phasing Alice at all.

I leaned forward again and quickly kissed her on the lips.

"Ok, better. You found my mouth at least. That's a good start." she said joking.

"Ok, this time don't do it so quickly, push gently on my lips."

I tried again, my lips pushing against hers. Her lips were soft, with a slight hint of strawberry from the lip balm she used.

"Ok, how was that?" I asked.

"Good."

"Ok, so we've got the basics down. Do you want to try some tongue?"

I recolied a bit at the mention of tongue.

"I don't know Alice."

"Oh stop being a wuss and kiss me again."

I kissed her again, but this time Alice stuck her tongue in my mouth. I could feel her tongue meeting mine. I tried to copy her movements and then she pulled away. She licked her lips slightly.

"Ok, that was good, really good."

"You mean it?"

"Yeah, you were gentle, you didn't push to hard like trying to push a snake down my throat. It was nice."

I smiled at the compliment.

"See, wasn't so bad was it?"

"No, I guess not." I said feeling slightly relieved.

"Do you want to try again? Maybe this time a bit longer." Alice asked.

"Um ok."

We locked lips again, our tongues lashing against each other. My jaw soon began to ache we were at it so long. I pulled away and wiped a bit of saliva from my lip.

"That was nice."

I looked up at the clock behind Alice, it was nearly 7pm.

"Shit, lost track of the time, I need to be back for dinner."

I got off the bed, not knowing I was pitching an almighty tent in my shorts.

"Uh, got a little too excited there sport."

I was confused for a second, then looked down.

"You boys and your things." She said waving her finger.

I blushed.

"Ah, um, sorry. But thanks for the practice though. I really appreciate it. You're the best."

"What are friends for." She replied and threw my school bag at me.

"Later nerd."

"Nerd." I replied back and left her room.

The following day after school, Alice and I walked home together.

"So, did she ask you out?" Alice said all inquisitively.

"Yeah she did."

"Way to go stud." Alice said and punched me in the arm.

"So where are you taking her?"

"Probably the mall, then maybe catch a movie."

"Then maybe you can put the moves on her."

"Alice!" I shouted while nudging into her.

"I am gentleman." I said in a mock old english accent.

We got to her house and went upstairs to her bedroom again. I flung my bag in the corner and jumped on the bed and crossed my legs.

Alice dropped her bag in the corner and turned to face me.

"I know I offered, but yesterday wasn't too weird was it?" She asked.

"Maybe a little weird, but it passed. I guess you were only trying to help and I can't thank you enough for that."

"Oh you. You're making be blush." She said comedically.

"I was wondering however..."

"What?"

I tried to pluck up the courage.

"If maybe we could practice some more. I want to make sure it's perfect and you know what they say practice makes."

"So suddenly you're a convert now. Hmm. Well fine, but only because you're my bestie."

Alice jumped on the bed next to me and we went to it. We were at it for fifteen minutes, when Alice broke off the kiss, her face was all red.

"I don't know about you, but all this kissing is making me thirsty. Do you want a drink?"

"Sure."

It was perfect timing on her part as I had another boner and I didn't want her to see it again. I was desperately trying to will it to go back down, but it was not having any of it.

Alice returned after two minutes holding two glasses of water.

"Here you go." She said passing me the glass.

"Thanks."

I gulped down the water as Alice slowly sipped at hers.

"Do you want to carry on?" She asked.

"Can we take a break for a minute. I'm kind of uncomfortable at the moment."

"Oh, do you want me to get you a pillow." She said putting her glass down and getting up to go to her closet.

"I've got a spare in here somewhere."

"No, no, not that uncomfortable. This uncomfortable." I gestured down with my eyes.

"Oh, ohhhhhhh!"

I could see her face change as the penny finally dropped.

"Again! What was it this time?"

"The joys of being a boy I guess. This thing goes off a thousand times a day."

"Really, that often."

"Yep, I could be running, wearing shorts, in the shower, on the bus, see a pretty girl and then boom." I said gesturing with my hand.

"Does it hurt?"

"Sometimes, it can get so hard it's starts to ache."

"How do you make it stop?"

"Well either it will just pass on its own, or you know, you take care of it."

"And do you? Take care of it?"

I paused for a moment, wondering why she was suddenly so curious. This was certainly new territory for Alice and I, but if she honestly wanted to know, then I'd tell her.

Alice picked up on the hesitation.

"I'm sorry, this is too personal, I shouldn't have asked. Sorry."

"It's okay, no secrets remember."

I took a deep breath.

"God, I can't believe I'm telling you this, but yes, I take care of it."

"What's it like? Is it like a woman's?"

"I wouldn't know. Do you, you know take care of yourself?" I asked turning the tables on her.

It was her turn to hesitate.

"I do. May be when I'm in the shower if the mood takes me or sometimes in the bath."

I don't know why, but this kind of shocked me. It seemed like it was a running joke, that teenage boys were always at it, but you never really heard the girls talking about it."

"Really?"

"Yeah, it's not just you boys that get horny you know."

"So what does it feel like?"

Alice closed her eyes, looking like she was trying to recall the feeling.

"It's like, I don't know, waves of pleasure, the kind that builds up over time and you don't want it to stop and you just let it wash over your body. Your heart starts beating quickly and you feel that heat and wetness between your legs and you just have to keep going and then you just want to scream out loud."

For briefest of moments and unusal for me, I pictured in my mind Alice naked in the bath, her fingers between her legs pleasuring herself, screaming out in ecstasy, her naked body writhing in bliss.

Then it happened, I could feel the hot sticky sensation in my underwear. I had just cum. I could feel it smeared between my dick and underwear. I quickly grabbed one of Alice's pillows and put it on my lap so she wouldn't notice.

"So, how is it for you?" She asked.

My preoccupation with what just happened in my underwear meant I didn't catch what Alice had just said.

"Mmm, what? Sorry."

"I said what's it like for you?"

"Well, I don't think it takes as long as yours. Well not the rate at which I go at anyway. We just pump and pump and pump and then we just kind of explode. A bit like pumping up a balloon, you dont always know when to stop and bang, it explodes."

"I see, so it's gets messy then?"

"Yeah, very."

She paused, I wondered if she was picturing me as I pictured her.

"So are you good again?" She asked, bringing the conversation back.

"Um yeah, its calmed down a bit now."

"Did you want too continue or are you good now."

"I think I'm good. Thanks."

I paused for a second. I didn't think my dick could take another kissing session with Alice.

"Is there anything else you want to ask me? about you know, boy stuff." I asked candidly.

"Nothing else comes to mind. Do you want to ask me any girl stuff?"

There was so much rushing through my head, which I couldn't bring myself to ask Alice. I thought for now it was best to leave it there.

"Nope."

Our 'practice' session ended there and our chatting returned to normal things.

The following day was the day of the big date. I had arranged to meet Kim and we spent the afternoon at the mall, before heading over to the theatre to catch the movie. As we entered the screen, Kim grabbed my hand and led me up the stairs to the very back row.

"Come on."

I followed behind her and we sat in the corner. The trailers started to play and the lights went off. We were still holding hands when the film finally started.

I was watching the film, when I could see in the corner of my eye, that Kim was staring at me. I turned my head and as I did she leaned forward and kissed me on the lips.

She kind of took me by surprise.

"You didn't actually think we came here to see a movie did you?" She whispered in my ear.

I looked at her again, a little slow on the uptake. Then it hit me, she came here to make out.

I leaned to the side cricking my neck and kissed her, this was going to be awkward and painful I thought, that was until she got up and sat on my lap.

We started to make out, I tried to remember everything that I did with Alice. Kim squirmed alot on my lap, grinding her ass into my crotch as we kissed. It was driving my dick wild.

By the time the movie finally finished my jaw and cock ached so much.

We left the theatre and I walked her home, holding hands the whole way. When we reached her house, she turned to face me.

"Thanks again for today, I had a really nice time."

"Me too."

"Maybe we could do this again."

"I'd like that."

I leaned in for a kiss and Kim matched my intentions.

"You're a really good kisser." Kim said as our lips pulled apart.

I smiled at her.

"Well, I'll see you tomorrow."

"Bye."

And with that she turned to go into her house.

I stood there for a moment, feeling really happy with myself. I couldn't wait to tell Alice how it went.

The next day, Kim and I made plans to see each other again and I didn't get a chance to see Alice until after school.

"Soooo. How did it go?" Alice asked.

"It was good."

"What did you get up to?"

"This and that you know. That and a lot of kissing. Alot."

"How was it - the kissing?"

"Really nice, I did everything we practiced and she said I was a really good kisser."

"Good, you are a good kisser. I'm glad you had a good time."

"I couldn't have done it with out you though."

Over the next few weeks, I've found it harder and harder to spend proper time with Alice. Kim and I started to spend alot of time together doing couple stuff and that unfortunately meant something had to give.

Alice tried reaching out, but one thing or another and I kept blowing her off, which I felt really bad about.

I thought I'd make an effort this time and had planned to spend the whole weekend with her to catch-up.

I met Alice at the woods at the back of her house, we used to play there alot when we were younger.

"Hey bestie." I said cheerfully.

"Hey stranger."

"Ouch, cold, but deserved." I responded.

"Yep."

"Look, I'm sorry we haven't hung out as much as we normally do, its just you know..."

"Kim!"

"Well yeah. She's my girlfriend now and I..."

Alice stopped walking.

"Look I get it ok. I knew this would happen sooner or later. I just..."

She paused for a moment.

"I just miss you that's all. We've literally spent nearly our whole lives together and then suddenly it stops. I just feel like you're starting to slip away from me."

I grabbed her arms and turned her to face me.

"Never. Me and you Alice, best friends for life. If I have a girl friend or you get a boyfriend.."

"Yeah right. boyfriend. Who would want me?"

"Who wouldn't want you. You're smart, you're funny, I suppose you could be considered pretty." I said trying to make a light joke.

"Hey!" Alice said smacking me on the arm.

"Look, my point is. What we have doesn't change just because there are other people in our lives, we just have to make it work."

"You're right I suppose. I just wasn't prepared for it to happen so soon."

We carried on walking through the woods and things were a lot better now that we'd cleared the air.

We were on our way back to Alices house, when inevitably the conversation turned back to Kim and I.

"So, how is it with you two?"

"Its going well, she's nice, I really like her. Her parents are away next weekend and she's invited me over."

"Oh really, well we know what that means. I think somebody wants a taste of Seans pickle." Alice said teasingly.

"I can't believe you just said that, what are you? Ten."

"I'm only teasing. Lighten up."

"Well easy for you to say. If it is what I think it is, then... well it'll be my first time and I don't want to mess it up. What if I do something wrong, or she laughs at me."

"Sean! You have to get out of your own head. You're your own worst enemy sometimes."

"It's different for boys Alice, it's a macho thing, that expectation to perform, what if I can't get it up, what if she thinks its too small, what if..."

We stopped abruptly.

"Sean, stop it."

She took a deep breath.

"What if I could help you?"

I looked at her.

"What - us have sex?"

"No, nothing quite as dramatic as that. What if I taught you how to please a woman. That way if you focus on her, you won't need to worry too much about your own hangups."

"Hmm, I don't know Alice. This definitely feels like crossing a line. Not only are you my best friend, but wouldn't I technically be cheating on Kim?"

"I'm only trying to help you because you're my friend and if I'm totally honest, maybe I should start thinking about these kind of things myself. Perhaps think of it as an information exchange."

"An information exchange. Let me sleep on it ok."

"Sure, let me know what you decide."

We finally came full circle and reached Alices house again.

"I'm going to make a move, lots to think about."

"Sure, sure. I understand."

I turned to walk away, then quickly turned back.

"Alice!"

"Yes."

"Thank you for everything, I mean it. You're a good friend and I promise I will do better."

"I know." She said smiling and closed the door.

That evening I toiled with Alices proposition. I felt so conflicted, on the one hand it feels like cheating, but on the other I want my first time with Kim to be perfect, school could be a brutal place and if something goes wrong and word gets out, my life is over.

I also wondered how this would affect my relationship with Alice, there would be no coming back from this, was it worth it.

This was tough, up until the point where my head hit my pillow, I was debating it. I tossed and turned in bed, then grabbed my phone and messaged Alice - it was one word 'OK'.

She must have been awake too, as she messaged me back instantly.

She had sent a thumbs up.

The next day in school, I did my best to minimise my contact with Kim. Even the thought of what I was planning to do made me feel guilty.

I walked home with Alice as usual. My parents are out tonight, do you want to come over at say 7pm.

I felt my heart pounding in my chest, I thought I'd have a heart attack.

"Ok, 7pm it is."

I really didn't know what to expect from this evening. I was so nervous I threw up outside my house.

I literally counted down the minutes to 7pm.

I left my house and made my way across to Alices.

I knocked the door and Alice answered wearing just her robe, clutching it at the lapels.

"Come on in Sean."

I followed her up the stairs to her bedroom and closed the door behind me.

"So."

"So." She replied back.

"Are you ready for this? We don't have to do this if you don't want to. I won't be offended."

I took a big gulp.

"It's ok, I want to do this."

"Shall we start with the basics?"

"Basics are good." I said, my heart thudding in my chest.

I was so nervous, I was actually going to be trying sexual stuff and with Alice of all people.

"Maybe we should get naked first. If we can't do that, then I guess there is little point continuing."

Alice made the first move, she began slowly untying the belt around her waist, then paused suddenly feeling body conscious.

I held my breath in anticipation.

"And no laughing ok."

"I promise. Scouts honour." I said with my heart in my mouth.

Her robe opened and then she dropped it to the floor.

There she stood, completely naked before me. I struggled to take in the view all at once, I didn't know where to look first.