Kevin’s First Time

Fictional story of a guy losing his virginity to an older teen girl

I was 14. My sister’s friend Amy was 16.

Our parents were gone for the week. My sister was in charge and we had the whole house to ourselves. I was playing on my desktop and Amy came over.

“Hey loser! Whassup?”, she said and messed my hair. She was always calling me “Loser” when we were together but never around other people, a nickname.

“Oh hey beyotch.”, I said back

She put me in a head lock. Her soft tits against the back of my head.

“Doesn’t hurt!”, I said. She pushed on the pressure point on my shoulder. “Who is the beyotch? Who?”

“Ahhhhh dammit!”, I said wincing in pain.

“Who?”, she said

“Ok me! Dammit!”, I said. “Damn! What the hell is wrong with you?”

“You are so cute. That is what is wrong!”, she said. She messed my hair again and hugged me from behind. “Where is Tam?”

“She went to the store. She will be back in 10 minutes.”, I said.

“Cool. I will wait.”, She said and started to walk out to the living room.

“Quit staring at my ass!”, she said

“I…I…wuz…wuz…wasn’t!”, I said. I was, Hell what guy wouldn’t?

She laughed and came back. I was all blushed. “Would it kill you to tell me you like me?”, she asked

“What? Me? I uh…”, I said. She started laughing

“I think it would!”, she said

She pushed on my nose. “I like you! Maybe if you tell me how you feel you can see my butt bare BUT if you like the present situation then that is cool.”, she remarked snidely. She walked out to the living room.

I was thinking of something to say. “Something cool. Act cool. Act macho. That is it.”, I thought. I went to her trying to act that way. She laughed in my face.

“Oh my Lord! You are a doofus!”, she said. “Be yourself, Loser! I don’t like you because you put on an act. Have you ever had a girlfriend?”, she said. I shook my head.

“Oh boy! Like sculpting clay. Alright. Ever kiss a girl?”, she asked. I shook my head. I was so nervous. She was so hot. “Ok. First of all. RELAX! God you act like I am about to kill you.”

“Sorry.”, I said. She laughed. She slapped my face playfully.

“Hey what the fuck?”, I said.

“Oh you getting mad? Loo-sar!”, she said. She slapped me again.

“Fuck this!”, I said angrily. She grabbed my cheeks and kissed my lips. All that anger instantly melted away. I felt faint and almost did. My knees buckled a little.

She laughed. “Do you need an ambulance? My God you are a virgin.”

“I jus…jus…like you and I don’t wanna screw this up.”, I said

“Well then open your damn mouth when we kiss!”, she said and smiled.

She kissed me again. Oh it was heavenly. Our tongues danced together. We sat on the couch and continued making out. She pulled away and sighed.

She grabbed my cheeks playfully again. “DO YOU HAVE ANY COURAGE AT ALL? MAKE A MOVE! YOU HAVE TWO NICE TITS IN FRONT OF YOU. TRY TO TOUCH THEM. DO I NEED TO WRITE A MANUAL?”, she said and laughed at me. She looked at my boner. “OH MY GOD! WHAT THE HECK IS THIS? NOW I GOTTA DO MORE WORK!”, she said jokingly. She was so funny. She knew I was nervous as all fuck and made light of it to get me to relax.

She took my dick out of my pants. “Nice. Ever get your dick sucked?”, she asked. I told her no. “Figures. Too bad. A lot of girls are missing out I see!”, she said complimenting me. She slid my pants off.

She grabbed my dick. She put it against her forehead. Slid it down her nose and gave me a quick smile as as she went down on it. She deep throated me and came back up. I moaned. “You like that? I am going to give you the time of your life!”, she said with all confidence. Her tongue swirled around my cock head and she went down on me again. She sucked hard on the way back up. Swirled her tongue and went back down.

I heard a car pull up. “Amy! Stop! Tammy is back!”, I said. She giggled with a mouthful of dick. She came back up.

“Let’s freak her out!”, Amy said

“Let’s not! Come on!”, I said

Amy giggled and continued. Sucking my dick as hard as she could.

“Please!”, I said. She went down on me as my sister walked in.

“Amy what the fuck?!!!”, she said

“Awwww fuck!”, I said as I orgasmed. My dick was shooting pools of cum into her mouth as my poor sister watched horrified. Amy swallowed and rolled on her back. She was laughing hysterically.

I was so embarrassed. My dick and balls in view for my sister to see. Amy had cum rolling down the sides of her mouth as she laughed her head off. Tammy stomped off to her room.

“What the hell? My sister is probably going to need counseling and you are laughing your head off about it. She saw her brother naked!”, I said. In the back of my mind, I thought it was funny too. I was trying not to laugh.

Amy went in to talk to Tammy. I hear “How could you? He is only 14!”, Tammy said

“Who sucked their first dick at 14?”, Amy asked. Whoa, hearing some big sister’s secrets! This should be good.

“You know he is listening! Shut up!”, Tammy said.

“Kevin are you listening?”, Amy asked. I laughed and said “no”

“See! He is not!”, Amy said.

Next day she came by when Tammy was gone. “I knew your sister would not be here. Want another lesson Kev?”, she asked. I was far more relaxed now.

“Kev?”, I said. “Thought I was Loser?”

“Not anymore. You got your dick sucked. You’re still a loser but getting better!”, she said and pressed my nose.

“Well you are still a beyotch!”, I said and smiled. She shoved me into the couch. I had a button up shirt on and she ripped it open. She grabbed my throat pretending to choke me. “Don’t you ever call me that again!”, she said. She kissed me and bit my lip. I was hard as rock.

She saw my bulge. “Oh someone likes it rough! Good. I love it rough!”, she said. Her attitude changed. She was more bad girl now. “What’s the matter Kevin? Huh? Pretty girl make you hot?”, she mocked me and slapped my face. “You like being dominated?”, she asked. I didn’t answer.

She played with the bulge in my shorts. “Look at this! All your worth is right here! The only thing good about you. You loser!”, she said. I spanked her. I took her cheek in my hand and squeezed. She slapped me hard this time. “Don’t ever touch me without permission.”, she said

“I kinda like this side of you. It’s hot!”, I said. She was trying to hold back her grin.

She cupped my chin in her hand and squeezed. “Shut the fuck up.”, she said. She was a great dominatrix.

“Lesson two Loser! I want my pussy licked. Do it right or I will personally rock your world.”

She had a short skirt on and took off her underwear. I was dying to see that pussy. “Look at you! You never seen a girl naked before? You dying to see my pussy boy?”, she said

She took her dress off and there before me was a beautiful angel. “Oh my!”, I said

She grinned. She was trying so hard to stay in character but could not hold it. She strutted up to me. “Aw you like what you see Kevy? Little Kevy want to touch my pussy?”, she asked. She was shaved but had a little patch above her slit. I ran my finger down her slit. She slapped me hard. I was so turned on. She grabbed my hand. “What did I tell you about touching me.”, she asked. She bent my wrist back. “Stupid little virgin boy!”, she said. I winced in pain.

“Fuck this is hot. You are so beautiful.”, I said

Her face blushed. “Be quiet.”, she said with a smile. “You see this virgin boy? This is a pussy.”, she said. She spread her lips. “You are going to lick here.”, she said

“You are going to take these two fingers and shove them into my hole. Any questions?”, she asked. I just stared at her body. She slapped me and pinched my cheek. “DO YOU UNDERSTAND?”, she said. I nodded

“Stupid mute!”, she said. She straddled my face. I licked her tasty little clit as instructed. She pushed down on my forehead hard. “You are mine now! I own you! Understand?”, she said. She flicked her finger on my forehead. “Ok virgin boy you got the basics down. Now we 69. Get your fucking shorts off fast or you will be jacking off tonight!”, she said. I pulled my shorts down real quick. “Ah there it is.”, she said. “Isn’t that the most beautiful dick?”, she asked me.

“I ain’t into dicks!”, I said

She laughed. “Shut up or I will bite it off.”, she said laughing

“Yeah real convincing beyotch!”, I said.

“Why you little fuck! You know what fuck this shit. I am going to rock your world.”, she said

She got on top of me. She looked me in the eye “You ready?”, she said being serious.

“Yes!”, I said

She slapped my face and told me to be quiet. “Trick question. Dumb ass!”, she said and smiled. She lined my dick up and I tried to poke it in. I tried to help but got yelled at. Her warm tunnel just slowly engulfed every inch of my cock. She was wet and warm. She was slowly moving up and down on it. Her beautiful blonde hair surrounded my head as we made out. “You like your first time?”, she said sweetly. She rolled her eyes when I thought it was a trick question. “You are so cute.”, she said and smiled. “Fucking answer me!”, she said angrily

“Absolutely!”, I said. She smiled and giggled. Our tongues danced as her lovely body slid up and down on my dick. She let her tits hang in my face. I sucked on her nipples.

I rolled her on her side and overpowered her. My dick came out and she fought me while on her back as I tried getting back in. I grabbed her legs and pushed them forward and slid my dick back in. Her legs opened freely. She was digging her nails in my chest and beating it. Cussing me out. I slapped her playfully now. “Fuck me hard baby! Come on!”, she said

I was a virgin but I was totally into this. I grabbed her hips and just started pounding her. “Oh my God”, she said. She cussed me out but was mostly enjoying me fucking her. She called me a wimp for not cussing her out. Hint. So I did. It made it even more fun. She played with her clit. I called her a slut and a cunt. Told her how she liked being raped by a virgin. I pounded her hard right into my orgasm. Our bodies were making slapping sounds from me pounding her. We came together. Her head went back into the pillow. “Aww aww Kevin! Kevin! You are amazing.”, her pussy shot out juice.

“Holy shit! Aw Amy I love you!”, I said as I shot my load into her. I pumped every ounce I had into her and rested my head on her breasts. She laughed and stroked my hair. “You are adorable!”, she said. “You sure you were a virgin?”, she asked. “You did that pretty well!”

“I had a good instructor.”, I said. She laughed and kissed my head. “Don’t traumatize my sister by telling her we did this!”, I said

She laughed. “Every last detail.”, she said.

“By the way do you know how to sew buttons on a shirt?”, I asked. She laughed and pushed on my head.

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