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First Time With My Brother's Best Friend

Tags: virgin, outfit
This is my first story, hope you like and all feedback will be greatly appreciated.

Right I'll just set the scene....

Tom and I both go to the same college but he’s a couple of years older than me and is best friends with my brother. They’ve been friends for years and he’s watched me grow up. He doesn’t know but I've always had a crush on him but he’s never noticed me in that way until this day........

College had been holding cheerleader try outs and I was hoping to become part of the squad. It was the final day of the trials and I had been practising like mad to get it perfect and was very happy with how it was going. Tom and my brother had been watching me to tell me if I was doing ok and they said it was good.

After doing the routine and sitting to hear the outcome I was dead excited, the girls came and told us who had got on to the squad and handed out the uniform. When I got home Tom and my brother were in the basement playing pool and they heard me walk in. My brother shouted at me to come in and tell him how I'd done. I walked into the room, face looking sad and they both looked at me and started to say sorry, when I dropped my bag and pulled out the uniform. Tom smiled at me and walked over to me and gave me a big hug, lifting me off the floor. I loved that he did that, I could feel myself getting wet; just the touch of his hands and then body against me got me going crazy inside.

I ran upstairs to try my uniform on, then put my hair up and started practising in my room. I hadn't realised but Tom had come upstairs behind me and was now watching me, stood at my door. I turned round and saw him there and I started to blush, but giggled a little to try to soften my embarrassment.

"Does it look good on me?" I asked, praying that he would say yes.

“Looks good, hun. Never thought I'd see you dressed like that, shows your features really well." He was very confident which made me blush slightly more.

“Thank you. I was worried I was gonna look fat or it wouldn't fit. Hopefully now I'm a cheerleader, boys will start to notice me."

He looked at me then entered my room, closing the door behind him. "I'm sure they noticed you before, hun. I know I've noticed you."

“You’re my brother’s friend," I said, "so of course you have, but I mean I want boys to fancy me." As I said this he walked closer to me, just looking me up and down.

"Well what if I told you I fancy you?"

"Really?" I said, my heart beating so fast I thought I was gonna pass out.

"I have for a while now but seeing you dressed like that has basically made me want you more." He then pulled the waist of my skirt and I went flying into his chest. I felt his hand slowly running down my back and then on to my bum, when he suddenly clenched my ass cheek really hard. I gasped and got pushed into him even more. I could feel his cock in his trousers hard as hell pushed right into my tummy and I was starting to get very turned on.

He grabbed my ass a little harder and then moved his hand under my skirt to cup my ass cheek. "You’re not wearing any underwear. You are a naughty little girl aren't you? Were you hoping for something?"

I couldn't find the words to say and could feel my cheeks burning up.

"You wanted me to come up here and see you practising, didn't you?" As he said it he slapped my ass and the sting that I felt made me scream a little. He then put both hands under my skirt and picked me up till my face was in line with his. "Not gonna answer me then? You know good girls reply when spoken to."

I was burning bright red and couldn't say a thing.

"Well, if you’re not a good girl then that makes you a bad girl. Bad girls get taught lessons." A smirk spread across his face and I was a little scared, but so intrigued to know what he meant. He then kissed me passionately but very rough as his hands were massaging my bum cheeks, every so often slapping them one at a time. I wrapped my legs around his waist and he walked over to my bed and sat down.

He continued to kiss me and his hands then started to explore my body, going up under my tight new shirt and pulling me even closer. He stopped kissing me and lifted me off him so I was standing in front of him. He looked me up and down a few times. "Pull your shirt up just above your breasts, don't take it off, it's too fucking sexy to take off."

I did as I was told and just stood there not sure what to do. He then pulled me closer. "No bra on? Wow, girl, you really are trying to make me hard aren't you?"

He then took my nipple into his mouth and started to play with it with his tongue. I started to breath heavier and moan slightly when I suddenly felt his hand running softly and slowly up my inner thigh and then on to my pussy. "Oh. shaven. You are a very good girl. You know what a guy likes."

He started to rub his finger up and down my pussy as he sucked harder on my nipple. I grabbed on to his shoulders as I felt my like legs were gonna buckle under me. He could sense I needed support so he twisted me round and led me on the bed, but then went straight back to what he was doing. "Does that feel good? You're very wet."

I moaned and quietly said, "Yes, it feels so good." I then felt his finger stop at the opening of my pussy and he looked up at me as he slid his finger slowly and deeply inside me. I gasped loudly and my back arched at this new feeling that was happening.

"You're very tight, hun. It’s very good, I can't wait to put my cock in there!"

I shot back to reality. "But I'm a virgin, please don't hurt me."

"Oh, are you now? Well this is gonna be a lot of fun for me, I'm gonna show you a few things love. You won't know what's hit you."

"What about my brother, won’t he wonder where you are?"

“No he's gone to the shop. He'll be a while, which is good because I'm gonna make this last a while."

He started to finger me harder and faster, causing me to moan louder and he was biting down on my nipples. I was enjoying every moment of it but was scared of what was gonna come. He then started to kiss down my body till he found my clit. Still with his finger moving roughly in and out of my body, he started to flick my clit with his tongue and every so often suck on it as well. He could feel my pussy contract around his finger as I had my first orgasm. He removed his finger, got on to the floor and then buried his head between my legs.

He started to lick my juices away and then started to dart his tongue in and out of me really fast. All I could do was lay there and moan, "Oh god, Tom, that feels so good. Please don't stop."

"I decide what happens," he said to me with a look in his eyes that slightly worried me but turned me on even more. He continued to lick and suck my pussy for a few more minutes then he felt my pussy contract on his tongue as I had another orgasm. My legs came up and tightened his head into me.

He pulled my legs away and he stood up. "Enjoy that?" he said.

I was too overcome by my last orgasm to talk. I just looked at him and nodded.

"I told you bad girls that don't speak get taught a lesson. You don't listen do you?" he grabbed my hand and pulled me off the bed on to my knees in front of him. "Right then, girl, I'm gonna show you how to take a cock in your mouth properly." He undid his flies and let his trousers and boxers fall to the floor. "Now grab the bottom of the shaft and open your mouth."

I did as I was told and as I opened my mouth he put his hand on the back of my head and pulled me closer. He entered my mouth slowly and just pushing in ever so slightly to get me used to the new thing inside my mouth. I felt his cock hit the back of my mouth and then he started to speed up. "Good girls get treated nicely; bad girls have to take the whole of my cock and never try to pull away. Understand?"

I tried to look up at him to say I agree, but he just kept thrusting his cock deeper in my mouth, causing me to close my eyes and try to concentrate on what was happening.

"Oh yeah, that feels good. Move your hand up and down my cock as you do this, yeah just like that." After a few minutes of this I was starting to get jaw ache but I didn't want to upset him, so I tried my hardest to keep going. He could tell it was starting to hurt me as he saw my facial expressions change, so he pulled out of me completely and lifted me up to his face. "That was great, girl," he said and kissed me deeply.

I was melting into him and I wrapped my legs back round him I could feel his cock between us just outside my skirt and I was gagging for it to be inside me. "Tom."

"Yes, babe?"

"I want you to fuck me." The look in his eyes was answer enough for me.

"Don’t you worry, I'm gonna."

He went back to the bed and led me down on it, looked at me for a second still dressed in my uniform. "You look so hot in that." He then moved forward and hitched my skirt up a little.

"Can I not take it off?" I asked.

"No, you're gonna leave it on. It's getting me rock hard seeing you in that."

He then spread my legs and got between them and placed his cock at the opening of my pussy. "You ready for this?"

"Uh huh." He started to push in as I said those words.

"Fuck me, you’re so tight, I'm gonna fucking open you right up."

I was in pain but trying not to notice it. He pushed in a little further then pulled back out trying to get some motion and let the wetness make it easier. Each time he pushed back in, he went a little deeper until he felt something stop him. "This is gonna hurt a little, but once it’s done you will really enjoy it."

He pulled out and with a hard thrust I felt my virginity break. I screamed from the pain and a few tears started to slide down my face. "There we go, it'll be ok now." He slowly started fucking me until he could see I was ok with it and then he started to get a little faster

"Tom, fuck me hard please." As soon as I said that he pulled out of me and flipped me over, lifted my skirt over my ass and pushed back inside me. "You want it hard do you? Well get ready to scream your house down."

He put his hands on my hips and started to move me back on to him getting faster, harder and deeper with each stroke. I was screaming from the pain but was loving every minute of it. He then reached a hand round to my clit and started rubbing it fast and hard. With that he could feel my pussy get tighter and I screamed even louder as the most intense orgasm shot through my body.

"Oh fuck yeah, you liked that. I'm gonna fucking cum, girl. Your tight pussy feels too good. I'm gonna cum all inside your tight little virgin pussy." With both hands on my hips he got faster and harder than before. "Oh fuck yeah, oh can you feel my cum inside you?"

I could feel the contractions of his cock inside and it felt so good.

After he had completely emptied himself inside me, he stepped back and I fell forward exhausted and in pain. He lowered my skirt and flipped me back over to face him.

"That was brilliant babe and I definitely want to do that again." He then bent and kissed me very softly and then pulled me into his arms holding me tight. Then we heard the front door open. He got his trousers on quick and hurried out my room but then put his head back round.

"I've always loved you girl and now I love you even more, especially dressed like that. Same time tomorrow, my place."

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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