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  • Cheerleaders' Spring Break Ch. 04

Cheerleaders' Spring Break Ch. 04

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I was still sitting there on the covers of the bed, my back still cold against the wrought iron headboard for twenty minutes after my sister had left. I was still torn between crying to myself at being taken advantage of against my will and having a massive boner, when Riley walked in. She hadn't been there the day before, so I was surprised to see her.

Riley had been one of my few real friends at school since I had been held back a grade. She was perky and always happy. She had brown hair just past her shoulders, and brown eyes, and dimples. She was short, and pretty thin and cute, and her tits weren't too small. Even though she was skinny, she had a well-rounded ass. She was always complaining that people thought she looked like Miley Cyrus. The fact that their names rhymed only added to the occasional joke. We weren't friends enough that we'd hang out often, but we'd had classes together for years, and she was probably the only girl I really felt at ease talking to or joking with. She had even confided in me some frustrations she had in her relationships, and I had reciprocated by opening up about some of my fears and struggles. I had almost asked her out a few times, but chickened out because I didn't want to ruin the good thing we had going. I'd have loved to date her, and I think we'd have made a great couple, but I just didn't have the guts.

"Riley, what are you doing here?" I said, with sincere cheerfulness, as she came into the room and closed the door.

"Ugh." She breathed, coming into the room, setting her phone on the nightstand and crawling onto the bed next to me. "I had a stupid student government meeting this morning at the school. It's so dumb that they make us miss the first day of Spring Break for it, when the school year is almost over, and everyone is already off having fun."

"Anyway," she said, crawling right up next to me "When the girls texted me the picture from last night, I knew you were going to be royally pissed, and came straight here from the school."

The fact that she was still wearing her plaid uniform was evidence of that. She had on knee high red socks, and a short red and blue plaid skirt and tight white shirt and red sweater. She crawled right up to my lap, pulled off my covers, and straddled my hips. I didn't toss her off, but was about to protest her being so forward when she leaned right in and kissed me full on the mouth.

I had dreamed about Riley being my girlfriend, and there were even a few points in our friendship that it almost seemed like it might happen, or she had acted like she was coming on to me, but I either chickened out or was too scared of the consequences of having a hot girlfriend. And despite my frustrations with current events, this was definitely a great distraction. I would gladly kiss her, as I doubted Riley could have agreed with the girls plans. She was as close to a female friend as I had.

We kissed deeply for a few minutes, and it wasn't until I realized that she had started to ever-so-lightly grind against my obvious boner, that I pulled away from the kiss. Her skirt was spread out, and all that was between my raging boner and her pussy was her underwear and mine. The feel of her heat through thin cloth was a huge turn-on. My habitual moral defenses started to flare.

"Riley, I shouldn't do this."

She put her fingers to my lips, and quietly shushed me. "Ben, I know that this is hard for you, and I know that you really want to save your virginity. But you and I both know that deep down inside you really want this. And I love you too much and am too fucking horny to wait another minute for this to happen."

She gently grasped my hands and lifted them above my head, as she leaned in to kiss me deeply again. The feeling of her warm wet tongue wrestling with mine was too good to stop and I allowed it. I couldn't believe she'd just told me that she loved me. She left my hands there against the ironwork framework of the headboard, and reached into the back waistband of her skirt, pulling out a pair of fur-lined handcuffs.

"How about you let me put these handcuffs on you, just to help you remember how much you want to be here?" She smiled. My mind screamed out that I should try to escape the situation, but my body was frozen by the raw eroticism of what was happening. I guess I could let this go just a little bit, and just stop her if she tried to take it too far.

I heard the clicks of one handcuff as it tightened around my wrist, and she leaned back into to kiss me deeply as she looped the handcuffs through an iron post of the headboard and handcuffed my other wrist securely.

I was about to complain again, and she pulled back looked me in the eyes.

"Ben, there are a bunch of girls in the other room, you know. And if you aren't quiet, they'll probably come in to investigate, which you do not want. You see, we drew random numbers to see who would get to have you first. Kasia drew number one, and I drew fourteen." She frowned slightly as she remembered it.

"But I knew that Kasia would ride you like a bronco, and wouldn't give you the time or attention that you deserve your very first time. Luckily your sister is surprisingly sensitive to breaking into this experience gently, and wanted to give you until this afternoon to let everything sink in before we take turns ravaging you. And they don't know I'm here yet, or in here with you. So you'd better be quiet." She smiled, and tossed her longer-than-shoulder length brunette hair to the side. "I can't imagine you'd want them watching what we're about to do. Or worse yet, try to steal you from me."

I looked at the door, desperate to talk my way out of the situation, but helpless at the gaze of this beautiful girl who I had such powerful feelings for. Looking into her deep blue eyes, I realized exactly what she was telling me, my lust began to flare and my breathing quickened.

"I couldn't stop thinking about you when I was at the school today" she continued. "I even left on this little outfit for you. And now you're looking at me like you want me to take it off."

I took another breath, about to respond, and she just pressed her fingers to my lips again. After a few seconds, she climbed off and stood up next to the bed, turning so I could admire her legs, and unbuttoned her sweater.

She hesitated on the last button. "You had better be a quiet boy, or you are going to regret it. Do you understand?" I nodded.

She pulled back the sweater and started to run her hands across the shirt covering her breasts. "And do you know what?" She said coyly. "I didn't wear a bra today."

I could see her nipples starting to harden against the thin white shirt she still had on. She ran her hands across her nipples through the fabric, bringing them to full attention.

"I really can't believe this is finally happening." She said, lightly laughing. "And especially with all those girls out there missing out, not knowing that I'm in here rubbing myself for you... undressing myself for you."

She took off her necktie, and started to unbutton her shirt. Her shirt opened more and more and she was indeed wearing no bra. Her hand snaked into her shirt and she quickly caressed a nipple, closing her eyes and licking her lips.

She looked at me in the eyes again, and started to open her shirt further. Her breasts were small, and her nipples were hard and tight, showing her obvious excitement.

"You like my little nipples?" she mused. Fully exposing her breasts now, and running her hands all around them. She gently massaged herself on each side, and pulled at her nipples to stiffen them even more. Each hand exploring her skin the way part of me wished my hands could right now. My willpower was starting to fade, and I was rock-hard with pent-up desire for this girl I'd wanted for so long. I couldn't believe this side of her that I'd never seen before, her actions overtly sexual and assertive. But she was acting so shy at the same time.

Her breasts were small enough that she could just barely press them together as she continued to massage them. She gazed into my eyes as she licked her fingers with the flat of her tongue, and rubbed her now slippery hands over her nipples again.

"They're getting so hard. I love to play with my nipples when I'm lying in bed thinking about you." She giggled. Tugging at them more firmly now. They were sticking out nearly a quarter inch, and were bright red.

"I'd bet you really want to see my pussy, huh, you dirty boy? Shame on you." She was only a foot from the edge of the bed, and as her hands left her breasts, I could see the saliva still, wet on her nipples in the cool air.

Her hands roamed down her body and started to hike up the hem of her skirt, revealing thin white cotton panties. She giggled again, and tugged the top of her panties down just a hint. I could see the top of her closely trimmed bush as she ran her fingers over her pubic mound. Her fingers wandered near her clit and she smiled.

I involuntarily lurched, my cock straining to get free from my underwear with a mind of its own, and she laughed again.

"You like that, don't you." Her panties were pulled halfway down, just barely covering the lips of her pussy, her barely visible pubic hair clearly in the open.

She let the unbuttoned sweater fall from her shoulders.

"I bet you want to see my little bum." She giggled. Turning her back to me, she lifted up the back of her skirt, revealing panties half covering the cheeks of her ass. She leaned her ass towards me and I realized that I'd never been this close to an undressing girl. I could see everything so clearly. I could make out the smoothness of her skin, and smell the perfume she was wearing.

Just as I was relishing how close she was, she sauntered over to the overstuffed leather chair just to the side of the bed. She kneeled on it, leaning her whole body forwards and sticking her ass back towards me. Her knees were together, and her skirt pulled up to her waist. She bent herself down onto the chair, and her ass stuck straight up into the air. Her panties stretched against the strain and I could see her pussy clearly outlined, a wet spot starting to form. She swayed her ass back and forth, the panties pulling up between her cheeks and she looked back over her shoulder at me.

"I stripped so many times like this, thinking about you being with me in my room."

She turned and sat on the chair, the skirt still pulled up around her waist. She ran her hands across them, before pulling them to the side revealing her pussy into full view. She ran the fingers of one hand over her swollen pussy lips, again and again, biting the lips of her mouth as she did. Her bush was closely trimmed, but her pussy lips were completely shaved. They were wet with her pussy juices and her fingers slowly spread that juice up and down the length of her slit.

"Do you like my pretty pussy?" She said, her fingers pausing briefly at her clit, before sliding along her slit again. "I bet you just want to gobble it up!" She said, giggling again.

She moistened a finger in her mouth, knowing the extent to which she was turning me on, and leaned back in the chair, raising one of her feet to her ass, her legs now spread wide. Knee high socks had been a turn on before seeing my sister strip with them, but now they would forever remind me of this moment.

She used one hand to spread her pussy lips, and her other wet fingers went to her clit. She made small circles with her index finger, stopping momentarily only to pull up more of the juice now dribbling from her love hole. She circled her clit with her fingers slowly. "I really like teasing my pussy for you." She said, and slid those fingers up and down her slit again and again. "It makes me really wet."

The strain of my dick on my underwear was unbearable now. I had just about given up deciding if this was okay, and realized that I wanted to taste that pussy I was staring at. She was rubbing her pussy lips with all the fingers of one hand, and I circled my hips against the air in time with the circles she made on her pussy with her hand.

"Oooh. You're so bad!" She laughed. She had the inner lips of her pussy grasped between her fingers, and other fingers spread the outer lips of her pussy wide. She moved her fingers around, clearly getting off on her own actions. "Am I making your cock hard? I barely nodded. "Dirty boy? Shame on you..."

She pulled both legs up now, spread wide, with her knees almost up to her shoulders, and rubbed both hands across her pussy.

"... letting a dirty girl like me make your cock hard." She dove two fingers into her pussy about an inch, and circled them there. "You're making my little pussy wet."

She pulled her knees together, and rolled sideways in the chair. Her ass was pointed right at me, her pussy still visible with her panties pulled to one side. She rubbed up and down her slit again, dipping her fingers inside her once or twice before standing up from the chair.

"You know what I really want to do?" She licked her tongue along her teeth, and nodded at me. I lay there speechless still.

"I'm a hungry girl... a VERY hungry girl. And I came to your room today for one reason: To play with your cock." She stood and walked to the foot of the bed, standing between my feet. "I bet it is going to be my new favorite toy." She giggled, undoing the last button of her shirt. She pulled her shirt open, and worked her small nipples again, staring straight at my dick. "It's so hard, because you keep looking at my pretty little nipples, huh?" she said as she rubbed her perfect little tits "And I have a soft little mouth that is going to make you feel so good." She said, sliding a finger into her mouth, and slowly drawing it out as she sucked on it.

She crawled up onto the bed, running her hands all the way along my legs as she did. My cock involuntarily jerked again. She leaned down, and licked at where my cock hid in my underwear. She ran her tongue along my underwear where the ridge of the head was clearly visible, and licked to the base, then kissed her way up my underwear, and kissed along my stomach. Her hair was held back by a plaid headband, but some of her hair still tickled my bare skin as she did.

She hooked her fingers on the waistband of my underwear, and started to pull them down. It was one thing to watch this beautiful girl dance around and strip. But to see her undressing me was too much.

"Riley!" I said in a loud whisper. "Really, we shouldn't do this. I can't let you..." I pulled on the handcuffs, which were very real, and they bit into my wrists through the fur lining. I pulled again on them harder, straining against the iron framework of the bed, and it was unyielding. So was Riley, who just smiled at me as she pulled my cock free from my underwear.

She was licking her lips as it came into view, and she lit up with a giant smile. "Dear God, this is huge. I bet you're really excited, aren't you? You sure look like you are." She purred. "I bet you've always really wanted to feel my tongue on your cock. Especially now!" Her face was so close to my dick that I could feel her exhale on me.

She used a few fingers to pull my cock up off my stomach, and stand it straight up in the air. It swelled involuntarily at the feeling of her light touch. She smiled and giggled again. "Look how hard your cock is for me!" She said, looking right into my eyes. Her tongue reached out and swiped a few times at the underside of my engorged head, surprising me with how good a simple brush of her tongue could feel.

She grasped my cock firmly in one hand, reminding me of the picture I'd so recently seen on my sister's phone, and Riley's hand was nearly as tiny, dwarfed by my monster. She paused, then said: "Tell me that you want this to stop. Tell me that you can't wait to see how amazing I can make you feel."

I wanted her to stop. I hadn't wanted it to be like this, but I had fantasized a thousand times about something like this happening, and she was right there, just inches from giving me the best pleasure of my life. I was weighing my options, but couldn't bring myself to say no.

She slowly licked up the entire shaft with the flat of her tongue, staring in amazement as she did. Then she looked into my eyes again and gave the tip one small delicate kiss. Her mouth opened and she enclosed the head with her lips, only letting the head into her mouth, and slid her lips up the head until she ended in another soft kiss. She repeated this again and again, sending jolts of pleasure right into me so powerfully that I completely forgot my struggles from just a few moments ago.

She got more comfortable on the bed between my legs, and then leaned back over my cock. She took it deeply into her mouth this time, taking nearly half of my cock in at once. I could feel my head jabbing against her throat as she did. She bobbed once or twice, and then slid my cock out again slowly.

This was just as powerful as the blowjob I'd gotten the night before, and it was compounded by being able to feel her hair against my hips, and see her half-dressed body as it moved and arched. The visual stimulus was overwhelming. And the style she had was also completely different than whoever had sucked me off last night. Riley was so cautious and gentle.

She pulled my underwear lower down my legs, and my balls came into her view. She cradled them gently, licking around them. She kissed one and then the other before sucking one right into her mouth. She laid them back down, and returned to my twitching cock, and drove her head onto it again. She had it deeper than before, but wasn't close to having my entire length down my throat like the girl from last night. Regardless, the sensation of her head bobbing my cock into her throat over and over was delightful. I could hear the suction as it pulled out of her throat and the slurping from all the wetness. After each thrust of her head, she looked up at me with those beautiful eyes, now watering just a bit from the beating she was giving her own throat with my cock. She rhythmically plunged several times before gasping a quick breath and went back to plunging. I was sure that if I hadn't come earlier this morning, this would have been enough to send me over the edge, and luckily I had some endurance to enjoy this.

She pushed her head down harder, and I could feel how tight her throat was with nearly three quarters of my cock in her mouth. She just looked into my eyes and plunged her mouth onto me with steadiness. I could feel her saliva dripping to my balls and she must have noticed, because she grinned and stopped to lick it up with her tongue, a long string of pre-cum mixed with saliva, strung between her mouth and my cock. She switched to long licks along all sides of my cock, with the occasional suck on the tip.

I groaned in appreciation, and she giggled and smiled up at me. "Ben, I love to play with your cock." She said, beginning to use her saliva to gently pump the head of my cock with one hand. It felt glorious, and her sincere smile convinced me that there wasn't another thing in the world she'd rather be doing right now.

She made a game of spitting onto my cock and then licking it all around until she'd cleaned it up, sucking the wet head of my cock into her mouth. Her sucking intensified, and she sucked the head of my cock harder now, comfortably in her mouth, as the same hand continued to pump at the base of my cock. She would suck on the tip for a few seconds before bobbing deeper, and then alternate shallow and deep. Then she'd spit on my cock again and repeat the whole process.

The tightness of her throat as she tried to swallow my entire length reminded me of how I'd always imagined a pussy to be tight. I wondered as she continued to alternate deep and shallow slurping bobs of her head, if she was just planning on a blowjob, or if she was really intending on having sex with me.

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