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First Time...Again

My ex boyfriend and I were definitely not one of those couples that ever got bored sexually. In fact, most of my first time trying new things all happened with him. From my first time trying anal to first time being brought to an orgasm in front of tons of (unknowing) people; to first time having sex outdoors, and even random things such as giving him head while he was driving. He even made me cum while we were watching a movie with my family... completely unbeknownst to them...

However, one of his favorite things to do was role play. We tried all sorts of different roles, but one of his favorites, and what this story is about, is role playing about me being a shy, innocent virgin, and him taking my virginity; gentle at first, before becoming rough.

I was sitting at home on my bed talking to my friend Stacey. Typical mindless chitchat and gossip about boys and girls at school, who was fucking who, etc. After a few minutes I heard my phone beep and saw on the caller i.d that it was my boyfriend Todd.

"Sorry Stace, gotta go, Todd's on the other line."

"Alright, I'll see you tomorrow morning before school." I switched over lines.

"Hey babe, miss you," I said in an innocent voice.

"Miss you too. What are you up to?"

"Oh nothing, was talking to Stacey. How was work?"

"The usual, hard, but it's worth it for the money."

"Aww. Are we doing something tonight?"

"Yeah, I was gonna see if you wanted to come over..."

"Kay, I just gotta change then I'll drive over."

"Alright, see you in a bit. And babe?"


"Do you think you're ready tonight?"

"Ready for what?" I asked, genuinely confused.

"Ready to... you know...take the next step..?" He asked innocently. Instantly I knew what we were doing that night.

"I-I guess so..." I said back, pretending to sound shy and hesitant.

"We don't have to..."

"No, I-I want to. I'm just a little nervous. That's all... I'll see you in a little bit."

"Can't wait!"


"See ya."

I hung up and got up to chose an outfit. I needed to look innocent, which was hard with my natural curves and general sex kitten demeanor. But after all, imagination is what role playing's all about.

Underwear. I needed some cute girly underwear, not my usual black lace. I went with some pink booty shorts and a pink push up bra. Now for clothes. Did I have anything innocent? What did the younger non slutty girls at my school wear? It was hard for me to find something. Cleavage covering t shirts always pulled tight across my DD's and showed my belly due to my long slender torso. Actually, that sounded perfect.

I dug through my old clothes and found the perfect t shirt. It was pink with two teddy bears on it. I paired it with a pair of my blue spandex hot pants, and topped it off with some thigh high white tube socks with two pink stripes at the top. Perfect.

I considered putting my hair up or into pigtails, but decided to leave it down so I could innocently play with it and act nervous. One last look in the mirror and I was off. I new Todd would have trouble playing the part, he'd want me so bad.

Twenty minutes later I was at his house.

"Todd?" I called innocently after walking through his front door.

"In the living room babe," he called back. I adjusted my clothes and walked in.

"Hey babe," as soon as I walked in the room I saw the want in his eye. My pussy began gently tingling, anticipating the game to come.

We kissed and he lingered for a second, but I pulled away, teasing him.

"You look amazing," he said, smiling.

"Thanks," I replied, looking down and pretending to be shy.

"Come on, let's go upstairs." We went to his room and I sat innocently on his bed, twirling my hair around in my fingers and pretending to be nervous.

He sat down beside me and looked at me, smiling at my pretend shyness. He put a hand on my lower thigh, touching my sock before slowly bringing his hand up to the top of my tight shorts, which had ridden up high.

"Cute socks," he said.

"Thanks," I replied, leaving it hanging in the air.

He brought me closer and began gently stroking his fingers up and down my back before sliding it underneath. I loved the feel of his fingers gently trailing up and down, it sent shocks through my entire body. I knew the teasing and build up was killing both of us.

"It's a little hot in here," I said, standing up and turning on a fan. This would make my nipples hard and make me shiver when I stripped off my clothes later. I sat back down beside him.

He began rubbing my thigh again, sliding it more inside. Heat burned up to my pussy and an image of him fucking me senseless flashed into my mind. The throbbing in my clit intensified and I took a sharp breath in.

"It's O.K baby, it'll feel good, I promise. I only want to make you feel good."

"O-O.K Todd. I trust you," I said, biting my bottom lip. He slowly moved his hand up my thigh until it was wresting near my pussy.

"Spread your legs for me," he said. I did as I was told, looking at him with puppy eyes. He began rubbing my clit while looking me in the eye.

"Mmm, that feels good," I said. It did feel good, but I wanted his big cock. He slipped his hand under my shorts and panties, feeling my now soaking pussy, and continued rubbing my clit in gentle circles.

"Mmm your so wet. I told you you'd like this baby." He began movie his hand faster on my swollen clit and I spread my legs open a little wider."You like this baby?"

"Mmm yeah Toddy," I said sweetly, my breathing becoming a little faster.

"Good baby, it's only gonna get better.

"Oh yeah," I moaned as he switched to stroking his fingers up and down my clit. My breathing got even harder and suddenly he stopped, pulling his hand out. I was so insanely horny, I just wanted to rip our clothes off and ride him as hard as I could. I needed his cock soon.

He licked off one of his fingers.

"Mmm, you taste so good baby." I bit my lip and gave him the puppy eyes again. "Want to taste?" I did want to, he knew I loved tasting my pussy, but I stuck to my role.

"Eww Todd that's gross."

"No it's not, tons of girls taste there pussy's. Come on, try it."

"No," I said stubbornly crossing my arms.

"Oh, is someone being stubborn," he said tickling me while leaning me back onto the bed to kiss. I giggled and pulled away.

"Come here," he said, putting his hand back down my shorts while kissing me. I instantly melted into him. After a few seconds he pulled his hand out and smeared it across my lips.

"Todd!" I yelled, faking slight anger.

"Just try it baby, lick your lips." I did, slowly. "Not so bad, is it?"

"It- it's actually kinda good," I said sweetly.

"Here babe, clean off my fingers." Eagerly I did, slowly sucking each fingers clean. "Now go take off your clothes for me like a good girl."


"It's O.K..." I looked at him. "Just do it," he said forcefully.

I got up and walked over by the fan. Slowly I pulled my tight t shirt up over my head, my hair sexily fell around my big tits. Then I slowly stripped my tight shorts off. My pink panties were stuck to the wetness of my cunt.

"Help me with my bra?" I asked innocently. I craved his touch.

"O.K, but you have to take your panties off yourself like a big girl." He got up and walked over to me. Slowly he slid his hands along my sides before undoing the clasps. He sat back down and I let each strap drop, the cups still covering my breasts. I looked at him before letting it fall. As planned, the fan blew cool air across my chest and my nipples instantly became rock hard.

"Now your panties." I spread my legs slightly and grabbed each side of my tight pink booty shorts. Ever so slowly I brought them down. They clung to my pussy for a few seconds before dropping to the floor. The cool air hit my pussy, giving me a feeling of being completely vulnerable and exposed. I loved it.

"Mmm baby, you're so fucking sexy." Once again I wanted to jump on him and rip his clothes off. Instead I brought my hair over one shoulder, returning to acting shy.

"Your turn," I said.

He stood up and stripped his shirt off, I sighed as I took in his sexy chiseled body. It made me want to moan. I bit my lip and dropped my eyes as he took his shorts off revealing his huge stiff cock. I needed it inside me. I could feel my juices starting to leak down my thighs.

"Oh my God Todd, it's SO big. I-I don't know if it'll fit..." I said, quickly remembering my part.

"Don't worry baby. It will."

"But I've never had one in me before. It'll rip me in half!"

"It'll definitely rip you, but you'll be loving it within seconds. Now get over here and suck it like a good girl."


"Just do it already." He began getting a little more aggressive and the nice guy routine began to change. I loved when he forced me around.

"O-O.K. I've never done this before." I walked over to him and he ran his fingers through the back of my hair, bringing me in for a deep kiss. I could feel his cock between us and I reached down and massaged the head.

I could feel him begin to weaken slightly; I knew he wanted to fuck me right then and there. I broke away from the kiss, dropping to my knees. I licked my hand and began stroking up and down his cock before swirling my tongue around the head. I paused and licked up and down the sides, swirling my tongue back and forth as I moved back up then once again began sucking on only the head, like it was a lollipop. I wanted to tease him a bit. I stopped and stroked up and down.

"Am I doing this right Toddy?" I asked sweetly.

"Mmm yes baby. Put that cock back in your pretty little mouth." I did as I was told and began taking it deeper, sucking harder as I came back up and still using one hand to jerk it. I began gagging slightly as it hit the back of my throat, but it didn't stop me. He started breathing heavily as I sucked his fat cock. I could taste the salty precum oozing out.

"Mmm suck my fucking cock baby." I began moving faster and he started to fuck my mouth.

"Mmf mm mff," I choked as he began moving faster. I slowed him down and took his cock out. It made a popping sound as the head popped out. I pushed him down onto the bed and began stroking him hard with one hand as I tongued his smooth shaved balls. In and out I sucked them. I could feel him tensing up so I stopped, not wanting him to cum.

He sighed and laughed slightly.

"Fuck baby, you are SO amazing."

"I was good for my first time?" I said, bringing him back into character.

"You were fucking perfect. Now it's my turn. Come sit that pretty little cunt on my face." He lay back on the bed. I climbed onto the bed and straddled his face, my thigh high socks still on.

"Mmm fuck you taste good," he said licking between my pussy lips.

"Mmm," I moaned. He gripped my ass and buried his face deeper.He began sucking my sensitive clit hard and fast, my breathing increased and I began moaning louder. Faster and faster his tongue moved, I began riding his face.

"Fuck! Jesus Chris Todd! I'm gonna cum!" As soon as I said that he pushed me off of him.

"What the fuck?" I said, panting.

His face was shiny with my wetness.

"No babe, you're not cumming like that for your first time. I want you to cum on my fucking cock!"

"O.K Toddy. I'm fucking ready give me that cock!"

"Mmm you're turning into a little whore already."

"Yes Todd! I need your cock now! Turn me into your own little slut. Please Todd, my pussy's dying!"

"O.K baby, but I want you to put it in yourself." His cock lay stiff against his stomach. I straddled him and began sliding my pussy up and down it, getting his cock good and wet.

"Don't fucking tease me, shove that prick in your cunt. Now!" He yelled, spanking me hard.

I leaned forward and grabbed his cock. I put it right above my tight hole.

"Ready baby?"

"Mmm fuck yeah." I began slowly pushing his cock head in when suddenly Todd yelled "Good!" and shoved his cock in, balls deep, thrusting up hard with his hips.

"Fuck!" I cried out as pain shot through me. I actually felt like a virgin again. I wasn't expecting him to do that and my pussy was still super tight and it felt like his cock had re ripped me open.

"Take it you fucking slut!" he yelled, thrusting up hard with his hips. Soon pleasure mixed with the pain.

"Unnnnhhhh! Fuck meeee! Shiiiiiit!" I moaned, matching his hard rhythm and slamming my pussy down as we fucked.

"Oh fuck! Fuuuuuck!" He moaned. All roles disappeared as we fucked like animals. My big tits slammed up and down, bouncing crazily as I rode him. Suddenly he sat up, throwing me to my back. He threw my legs over his shoulders and rammed me crazily.

"Holy shit! Fuck Todd! Fuck me! Oh my God! OhmyfuckingGod!" His sweat dripped onto my stomach, mixing with mine. I could feel my legs beginning to get sore.

"Lay down," I said.

"What?" he asked, so focused on fucking me.

"Fucking lay down!" I took my legs off his shoulders and sat up as he lay down. I leaned forward to our faces were near, never taking his cock out and he began fucking me once again. Our breathing was intense, our mouths inches apart. We locked eyes as he began moving faster

"Fuck me Todd," I breathed hard into his mouth. "Fuck me hard! Oh my God!"

"Take it all you fucking slut," he said. His balls were hitting my ass. He wrapped and arm around me to force me down deeper.

"Oh fuck! Oh fuck!" I dug my nails into his shoulders.

"You like being fucked like a little whore?"

"Mmm yeah baby. I fucking love it!"

"Good." He began moving even faster.

"You like that you fucking whore?"

"Oh yeah!"

"Take that fucking cock! Take it!"

"Fuck Todd! Fuck!"

"Take it all baby!"

"Unnhhhh! Shiiiit!"

Suddenly I felt my cunt tighten.

"Todd I'm gonna cum! I'm gonna fucking cum! Shit! Ohhhh shit!" He threw me onto my back, grabbed my legs and began throwing all of his weight into me with each thrust as he fucked me as hard as he could.

"Ahhhhhhhhhh!" I screamed, my pussy spasming as I came with all my might. Wave after wave of my intense orgasm pulsed through me.

"Oh fuck! Here I come to baby!" he yelled, and with a final thrust he came hard deep inside my pussy. I could feel his hot cum spurt into me and leak passed his cock and onto my asshole. He pulled out and collapsed on top of me. The room was filled with the sound of the fan and us panting. My pussy twitched every few seconds. The room smelled like sweat and hot sex.

He sat up and began breathily kissing me as we both lay still panting.

After awhile Todd looked up at me.

"That was fucking incredible."

"Mmm I know," I said, running my fingers through his hair and massaging his scalp. He smiled and rested his head on my tits.

"And that was the cutest fucking outfit. I love the shit you come up with."

"All to make you happy babe."

We returned to silence. He continued to cuddle me, and I continued playing with his hair.

"So. What should we do this weekend?" I asked.

He looked up at me and smiled.

"I have the perfect idea..."

Sidenote: I was 17, about a month before my 18th birthday when this happened and he was 25. Hope you all enjoyed!
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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