High School Hooker

Like I said, Lilly was one of the most beautiful girls in school. She was shorter than Kara by about three or four inches but often made up for that by wearing heels. She had long straight brown hair that was tied up in a cute but messy bun of some sort. She had big brown eyes accented by long lashes. She wore just a hint of makeup but not enough to hide the adorable freckles on her cheeks just below her eyes. Her lips were soft as they mashed against mine and I found myself starting to explore her body with my hands.

First I dipped one down her to ass. She had a perky bubble butt that was just made for squeezing. I slid my hands up her slim waist and ran my fingers lightly around the exposed skin of her midriff. She had the cutest belly button and a flat, smooth stomach. As she pressed her body against mine I could tell that she had chosen not to wear a bra underneath her thin spaghetti strap top and it made me wonder if she had any panties on under her tight jean shorts.

As we kissed she reached down and unbuttoned her shorts, pushing them down until they fell to the ground. She broke our kiss and grabbed my hand. As she pulled me over to the bed I could see her bare ass barely covered by a tiny thong. She backed me up to the bed and pushed me down into a seated position on the edge.

Sinking to her knees in front of me, her eyes never left mine. A sexy smile on her face the whole time. She fumbled with my belt for a moment before pulling it and my pants open. Then she drug my pants down to my ankles and off completely. My rock hard cock stood straight up in front of her, already teased from watching Kara earlier. A large drop of precum dripped down along the bottom of my shaft.

Lilly took it in her hand, smearing the precum around and started to stroke me.

"I've wanted to do this with you for so long!" She said, then dipped her head down and took the first two inches of my cock into her mouth.

"Ohhh..." I moaned. My cock finally getting the attention I had wanted since lunch. Although I much proffered this sort of attention to my own hand.

Lilly was slow and deliberate in her blowjob. Swirling her tongue around the tip of my cock while sucking on it, her hand slowly stroking the thick shaft and her fingers scraping against my balls. My cock wasn't enormous but it was definitely above average. I was proud to know that it was bigger than the guys I had seen Kara with.

Lilly removed it from her mouth and ran her tongue down the side and to my balls, licking one and then the other. She sucked one into her mouth gently, licking it in circles before releasing it and kissing her way back up the shaft.

"Emmmm...it IS big..." She said in between kisses. "Jennifer was right..." Then she took it back into her mouth, even deeper this time. Taking more than half of it in until it touched the entrance to her throat, then she started to bob her head up and down slowly.

'Jennifer?' I thought to myself. Jennifer was a girl I had dated earlier this year for awhile. We had slept together but the relationship didn't last long. Apparently girls talk.

After only a short time of receiving Lilly's amazing oral skills I could feel myself getting close. I ran my hand through her hair and held onto the bun lightly. My hips started to rock slightly but she had no intentions of getting me off yet.

"Nuh uh sweetie..." She smiled and gripped my cock tightly, holding it against her cheek. "Not yet! How about you come play with me for a bit?"

I grinned and nodded my head 'Yes'. I couldn't pass up an opportunity like that. Lilly stood up in front of me. She crossed her arms in front of herself and grabbed hold of her top, pulling it over her head to reveal her magnificent breasts to me for the first time.

Magnificent might have even been an understatement. They were perfect. Nice big hand fulls, no less than a C cup. Hardly any sag whatsoever. They were full and firm and sat high on her chest. Her nipples were hard and begging to be sucked.

She raised her hands up and squeezed them together in front of my face. Then she reached one hand to me.

"Touch them..." She said.

I reached up with my right hand and she took hold of it, guiding it to her breast. It was soft but firm in my hand. Her skin was so smooth and her erect nipple pressed against my palm. She climbed on top of me, straddling my lap as my other hand came up to caress her other breast.

"Emmmm..." she moaned and kissed me again. Her thong covered pussy ground against my naked cock. "They're very sensitive..." She informed me when I began playing with her nipples.

I kept on exploring her body. Cupping her ass in my hands and pulling her harder against my cock while she rubbed her pussy against it. Only the thin material of her panties separating them. Lilly climbed off of me and dropped down onto her knees once more. She took my cock back into her mouth, bobbing up and down on it just a few times before pulling away, leaving a thick coating a saliva on my penis.

"The best part of doing this here..." She said as she leaned forward and placed my cock between her tits. "Is that we don't have to rush...we can take our time..." And she pressed her tits together, smothering my cock between them and rubbing them up and down. Fucking my cock between her soft titflesh.

"Oh fuck..." I let out a soft groan. It felt amazing. I'd never tit fucked before and the feeling was better then I could have imagined. I sat there groaning as Lilly fucked me with her beautiful tits. Tilting her head down to lick the tip of my cock every so often, sending little shivers up my spine. I was really enjoying it but she stopped before I even came close to cumming.

"You were supposed to be playing with me...!" She giggled.

I smiled. "Sorry, you kinda distracted me..."

She giggled some more. The sound was musical. "I know, I just felt like doing that for a minute. We will definitely do that again sometime though. But right now I want to feel your tongue..." She pulled her thong down her toned legs and to the floor. Stepping out of it she sat down on the bed and lay back against some pillows. Her legs spread in front of me, showing me her pussy.

Just as everything else was on her, Lilly had a very pretty pussy. Her shaved mound led down to the tight folds of her pussy lips. They glistened with arousal and were parted just enough to show the pink of her pussy. I laid down on my stomach between her legs and ran my hands onto her taut stomach. Deciding to tease her a bit myself I started licking from her inner thigh. My tongue made it's way to her mound but completely avoided her pussy and clit. I licked down her other thigh then back up. Lilly squirmed slightly and I kept going. Finally, I licked over to her clit and began drawing tight circles around it with my tongue.

"Yesss..." She moaned and ran her fingers through my short brown hair.

I licked and sucked her clit, sometimes dipping my tongue lower to the entrance of her pussy and back up causing her hips to jerk upwards. I cupped my hands under her ass and squeezed her cheeks tightly as I pressed my tongue harder against her clit.

"Oh yes...oh you fucking tease..." She purred.

Finally I dipped lower and without warning slid my tongue past her lips and into her pussy. Pressing it in deeply and lightly twisting it around before coming back up and sucking on her clit.

"OH! Oh you bastard!" She squealed but her hands pressed my head harder against her pussy.

I continued to lap at her pretty little cunt for a few more minutes. My tongue licking from below her entrance all the way up to her clit. Finally she was close to coming. She held my head tight as I focused my assault completely on her clit. Her hips bucked up pressing her pussy harder against my face.

"OH FUCK! OH FUCK!" She moaned loudly. Then an orgasm swept through her body. She shivered in my hands, her hips grinding against me and fresh juices drenching my lips and chin. She reached up and squeezed her breasts, sending several more shivers through her body as she rode out the orgasm.

When her body finally relaxed and I knew that she was finished I pulled my head away, grinning up at her with a cocky smile.

She returned the smile and her hand went to her pussy, rubbing it slowly. "You are good at that!" She complimented.

"I aim to please!"

"That you did!" Then she sat up and pushed me onto my back. Lilly climbed up my body, planting little kisses along my chest until she made it up to my face. She kissed me hard, mashing her lips against mine.

"So..." She started. "Would you like to watch my ass bounce up and down on your cock? Or watch my tits bounce up and down while I ride you?"

"How about both?" I smiled hopefully.

"Good choice!" She winked. She spun around above me and straddled my lap with her back facing me. Her perky bubble butt in perfect view as she raised up and took hold of my cock. She rubbed it against her soaked pussy, the head of my cock slid easily between her pussy lips as she rubbed it back and forth. Then after lining it up, she pushed down and impaled herself onto it. I watched as her pussy lips stretched around the invading member. She raised her ass up again and pushed down harder, this time taking the entire thing inside of her.

"Ohh...you feel good..." She cooed. I reached forward and squeezed her ass in my hands. She began riding me, her ass slowly bouncing up and down on my cock. It really was an amazing sight to see. She placed her hands on the bed between my legs and bounced her ass up and down quickly. My cock slid into her tight pussy over and over, the feeling was incredible.

"Oh!...Oh!...Yesss..." She continued to moan as she rode me. My eyes were glued to her beautiful bum as I watched my cock repeatedly impale her tight pink pussy. My hands helped guide her ass up and down on my cock.

Lilly looked back over her shoulder at me with a wide smile. "I really like fucking you..."

I couldn't help but laugh. "I really like it too!"

"Tell me when you are starting to get close okay? I wanna turn around so you can squeeze my tits while you cum..."

I nodded 'yes' and continued to squeeze her ass. I bucked my hips up lightly each time she came down, pushing my cock just a little bit deeper. After a few more minutes I was starting to get close. I wasn't there just yet but I knew it wouldn't be long. And I really did want to see her tits bounce while she rode me, just like she said.

"Turn around..." I said. Lilly looked back and smiled. She swung her leg off of me, my cock slid out of her pussy. It was slick with her juices. She wasted no time in turning around and climbing back on, quickly impaling herself on my cock again.

Lilly sat there for a moment before starting to grind her hips around in a slow circular motion. She was breathing a little harder than before and her eyes were half shut. As she concentrated on the cock filling her pussy I reached down and pressed my thumb against her clit, stimulating those nerves and sending small lightning bolts through her spine.

Her back arched and one hand covered mine on her pussy while the other squeezed her left breast. She pressed down harder, grinding her pussy on my cock. She started panting in short, quick breaths and I could tell she was about to cum. Her eyes were shut and all her focus was on the feelings shooting through her body.

Finally her orgasm overtook her and she began bucking her hips forward and back. Not really riding me but continuing to grind against me hard as every nerve in her body fired off at once.

"UGGGGH!" She moaned and collapsed onto my chest. Her pussy began to spasm on my cock and I could feel it pulsing as she came. She pressed her hands onto my chest and lifted herself up, rocking her body back and forth while she came. She rode out her orgasm, taking in a breath that I hadn't realized she was holding in. Her eyes fluttered open and she smiled down at me.

"Oh my God..." She said. "That was soooo...ugh!" She couldn't continue as I bucked upwards once, sending one more jolt through her sensitive pussy.

"So...good?" I teased.

She nodded her head. "Very good!"

Once she recovered and wasn't quite as sensitive anymore she began to ride me. She kept her hands on my chest and quickly raised her body up and down. Slamming down onto my cock each time. I rested my hands on her hips, watching her perky teenage breasts bounce up and down as she rode my cock.

"Good sweetie?" She asked. "You like watching my titties bounce up and down while I ride your big cock??"

I nodded my head up and down, feeling myself getting close. I was surprised I had even lasted this long considering the circumstances. We had been messing around for close to forty minutes by now. At least half of that time was fucking.

Over and over again her ass bounced up and down on my cock. I could feel the warm velvety folds of her pussy slide up and down. Her pussy felt so snug around it and I knew I was only seconds away.

She must had been able to see it in my face. "Emmmm...you going to cum sweetie?"

"Ugh...uh huh..." I groaned.

"Squeeze my tits baby..." She ordered and I did. I took her firm breasts into my hands. Squeezing them tightly as I felt my balls begin to tighten.

Lilly leaned over, holding her head against mine, with her lips right by my ear. Still riding my cock she began whispering into my ear.

"Yes, cum for me baby...cum in my tight little pussy..."

She kissed my earlobe and neck, sending bolts of lightning down my spine and directly to my cock. The nerves in my dick began firing off as I prepared to blow.

"Fill that little pussy baby..." She continued. "Cum inside my pretty little pussy, I want to feel your cock shooting off inside me..."

Then I did. Every ounce of pent up lust from watching my sister fuck, through all the different sensations Lilly had given to me finally erupted as semen evacuated my balls and I released a torrent of cum into the beautiful girls tight vagina.

"UGH!...UGH!...UGH!" I grunted with each shot of cum.

"Ohhhh...oh fuck yess..." Lilly moaned into my ear, feeling my cock fill her with semen. Over and over again, thick jets of cum shot from me and into her pussy. My orgasm seemed to last for hours even though it was really only several seconds.

It finally started to subside and my body relaxed. Lilly leaned up and kissed my lips. Our tongues massaging each other again as we enjoyed the feelings. My cock still twitched slightly inside of her, our lips smacked together as we kissed, and my hands rubbed up and down her body.

She finally broke the kiss and sat up, looking into my eyes. "I can feel your cum leaking out of me..." She giggled.

I looked down to our joining and sure enough a large glob of semen was leaking from her and around my softening penis. She swung her leg off of me and stood up next to the bed. She walked out of the room and returned a few seconds later with a damp washcloth. She came over and wiped me off, cleaning the ruminants of cum and pussy juice from my cock before wiping herself clean as well. Then she climbed back onto the bed and lay beside me, resting her head on my shoulder.

"That was fun!" She said.

"Yeah...definitely!"

Lilly rolled over and propped herself up on her elbows, her pretty eyes looking straight into mine.

"Okay, I know you have questions still..." She said.

"Kinda...I guess."

She laughed. "You had questions before we did it...what, my pussy scramble your brain??" She teased.

I laughed at that then thought about it for a second.

"Well, really I was just surprised by the whole situation, thats all. You are the last person I would expect to be doing something like this."

Lilly nodded her head in understanding. "Yeah, I don't want it to make a reputation for me. I don't want people to think I'm dirty or slutty, you know?"

"Yeah, I get it. I mean, I don't really know you that well but from what I've heard and seen for myself, you aren't known for hooking up a lot. Or even at all really."

"I know. I don't sleep around like some of the other girls do. The boys that I have been with know to keep their mouths shut if they ever want a chance in my panties again."

"So why do this then? Why let guys pay to sleep with you? Won't word spread that you are doing this?"

"You had no idea I was doing it right?" She asked. She was right, I didn't have a clue. "I do it because I like it and I make a lot of money, thats all."

"I guess you're right. So, you said earlier that you have wanted to do this with me for a long time?" I smiled.

She smiled back wide. "Yeah, kinda. A few of the girls in our group have little crushes on you."

"Really?" I asked. "I didn't know that. What stopped you before?"

"Kara wouldn't let any of us. She is way protective of you."

"What? Why?"

Lilly giggled. "She would never say...but now from what she told me, I think she just wanted you for herself..."

My eyes widened and my jaw hung open slightly. "Huh?"

"Common Brian. You caught her on video getting paid to fuck. And for punishment she gave you back the tablet with the videos and had you come out to your truck and do it again?"

"Then why would she send me off with you? And pay for it on top of that?" I asked.

"I don't know. But I'm glad she did..." She leaned in and gave me a quick peck on the lips.

"I am too."

"That mean we will do it again soon?" She looked at me hopefully.

"Well, I would...but I'm not really...you know..." I tried to explain. "I don't think I would be the kind to pay for sex..."

Lilly laughed and shook her head. She smiled brightly and kissed my cheek. "No sweetie, I didn't mean like that. I know you aren't. I meant more like you could take me out for a date sometime and then after that maybe we could play some more..."

"Ohhh, ok I see." I slid my arm around her lower back and pulled her closer to me. "Yeah, I would like that. But you're gonna have to wait until I ask you out properly..." I teased.

"Ask me out properly then!" She smacked my chest playfully.

"Can't right now, it would seem like I only did it because you brought it up, you know?"

She smiled again but nodded. "I guess so. But don't make me wait too long..."

"I won't...actually, you should probably keep your weekend free, just in case..."

We both laughed. Lilly got up and left the room. She returned a couple minutes later with two bottles of water. I loved watching her walk around her house naked. I could stare at her body and pretty smile all day.

"So." She started when she came back and sat down again beside me. "My parents won't be home for over an hour and a half..."

"Oh yeah?" I said.

"Yup...so that means we have plenty of time to do it again..." She wagged her eyebrows up and down playfully.

"I don't know...you're pretty expensive..." I teased.

She splashed some water at me in mock anger and laughed.

"Don't worry sweetie..." She finally said. "That last one was your sister's treat...this one is on me!"

I left Lilly's house an hour later, well fucked and with a big smile on my face. Even though I had teased her about it before, I asked her out anyway and we made plans to go on a date the following Friday night. I went home feeling very happy and relaxed. But one thing still stuck in the back of my head. Why would Kara try to keep her friends from dating me? And why did she want me to watch her again?

When I got home dinner was already ready and I sat down to eat with my family. Kara gave me a knowing smile as I pulled my chair in and began to eat. I still wondered why she had paid for me to go with Lilly. 'I'm sure she will tell me later' I thought to myself as I took another bite of chicken from my plate.