Cheerleaders' Spring Break Ch. 02

Spring Break came before we knew it. All the plans came together so seamlessly, and my sister kept her word to make it as easy an experience as possible for me. She coordinated all the travel, and bought all the food we'd need. All she told me to do was to show up and enjoy myself.

The only deviation from my sister's promises came when she told me that not all of the senior cheerleaders would be there. It turned out that three of them, Monroe, Christa and Becky were not 18 years old yet. My sister didn't quite explain why that excluded then from coming, even though they were seniors too. But if Ivana wanted to exclude anyone on our trip who wasn't eighteen yet, that was her prerogative. I was just happy there were three less cheerleaders that I didn't have to worry about staring at.

Our caravan of cars full of cheerleaders didn't end up arriving until almost dark, getting out of school in the afternoon on a Friday. And before I had a chance to get swept away by my lust in a houseful of girls, I went right to the master bedroom to get unpacked, and use the solitude to get focused. I figured it was better if I wasn't around for the tedious task of assigning different girls to different rooms. Most of them would have to share a bedroom, and several of them would be sharing beds, and that was one more thing I didn't want to have to think about. I knew my fantasies would quickly get out of check if I was imagining specific pairs of hot girls in bed together. I knew they couldn't all be closet lesbians, but I was sure that I would get that cliché image of lingerie pillow-fights, or worse, stuck in my head for the rest of the night.

As it later turned out, about half the girls decided that they wanted a slumber party on the first night of our trip. There were a few rooms that were big enough to sleep them all in the house, but none were as cozy and flat out fun as the boathouse.

The boathouse was a small 30 foot by 50 foot cabin, just twenty steps above the lake. It had been the original home that was on the property when my parents bought it a decade ago, and had been transformed to be the place where we kept some of the boat equipment, water toys and life jackets. It was decked out like an entertainment room that had some couches and a TV, and a few bathrooms. As kids we'd often sleep in the boathouse instead of our rooms in the main Lakehouse just for the cozy experience, and to get away from our parents. There was something special about getting out some sleeping mats and sleeping bags that help lend a sense of adventure to a trip.

So with night setting in, about half of the girls made their way down the steps from the main house to the boathouse. It took a few trips to carry down some extra mattress pads and sleeping bags, and part of me was very glad I'd been asked to help carry stuff. When I got into the boathouse, most of the girls were lazing around in their skimpy pajamas. Several had on those tight short shorts or tank tops, and I don't think a single girl was wearing a bra. There were literally nipples poking against thin fabric everywhere I looked. Tori was there, and it didn't surprise me one bit that she wasn't dressed in regular pajamas. She was too sophisticated for that. She was casually talking to another girl, sprawled across her sleeping bag, wearing an almost see-through black teddy. It just covered her ass, and I could clearly see the thin strip of thong that disappeared between her cheeks. I kept peeking at her as I got some of the sleeping mats into place, and her teddy seemed to hike higher and higher each time I looked. The air smelled sweet with a handful of distinct perfumes, and the sight of pretty blonde Abigail rubbing lotion on her long legs was enough to give me a hard-on. Luckily I was still wearing jeans, and had time to escape before my dick tried climbing out of my pants to have some adventure of his own. I made sure the girls had flashlights, and got out of dodge before my willpower faded. I couldn't risk getting overly horny this early in the trip, or who knows what could happen.

I got back to the house, and was happy to find that most of the girls who decided to sleep in the main house were either heading to bed, or watching a chick flick in the den. I went back to my bedroom, and spent some serious time reflecting, trying to get my hormones in check and will myself not to look at some porn right now. I had to keep myself together.

It must have been an hour past midnight when my sister, Ivana, knocked on the door. I was in bed reading, so I called her in.

"Ben, we are going to sleep in the boathouse, but there are some trees creaking in the woods, and with it being so completely dark in there, a few of the girls are freaking out that a bear is going to burst into the room and eat them or something. Would you mind, pretty please, coming down to stand watch? I know just having you sleep there in the room will calm the nerves and help us all get to sleep."

I was feeling much more in control of myself now, and actually liked the sound of the water lapping on the shore and the sounds of the crickets down by the boathouse. I figured with everyone going to sleep in the dark I wouldn't be tempted to gawk. So I agreed.

I dragged another mat and sleeping bag down to the boat house, and got a chorus of "thank-you's" as I set up to sleep on the end of the room, right between the scared girls and the door to the boathouse. It was easier not to get distracted with most of them already tucked in for the night, and a few were actually already asleep. We said our goodnights and turned the lights back off.

It really was dark. Our parents had put blackout shades on the windows so we could sleep-in on summer days, and the loud buzz of a few old ceiling fans muted out most of the tossing and turning going on, so I quickly fell asleep.

I dreamed of girls. It was no surprise that my dreams centered on sex with so many of the girls that I'd been fantasizing about for years, who were sleeping in the same room as me tonight. At one point, I think I was dreaming about drilling Shawna while watching her big fake boobs bounce inches from my face, and the feeling of her pussy sliding up and down my cock felt so real. The slipperiness of her juices running down the sides of my cock and dripping onto my balls was making me writhe with pleasure. She slid up and down my pole, riding me, plunging my cock into her as far as it would go...

My eyes shot open in the dark, knowing that feeling was far too real. This was no dream. I'd never had sex before, and used masturbation as a rough indicator of what it would be like someday, but I instantly felt upon waking in the dark of night that my cock was rock hard, my pants were around my ankles, my sleeping bag had somehow been zipped open, and my cock was being serviced in the dark.

As my senses came to me, I panicked. I couldn't jump up screaming and wake the whole boathouse of girls to the sight of me with my pants around my ankles and my cock protruding in plain view. I had worked hard to maintain my chaste reputation and here I was practically being raped in my sleep and didn't know what to do.

I reached down towards my cock and felt long soft hair cascading all across my belly, and grasped the head of whoever was quietly slurping away at my cock, head bobbing up and down on my shaft. As soon as my hands grasped her head, she stopped bobbing, and I felt teeth starting to bite down on my cock. I nearly screamed in pain, but realized my surroundings again, and held my yelp of pain to a small grunt. We sat there, frozen, her teeth clenched into my skin while I grasped her head. I was at a total loss of what to do.

Without even loosening her grasp on my cock with her teeth, her tongue slowly started to circle around the engorged head of my dick. Her tongue flicked against the underside a few times, before circling again. The sensation was unlike anything I'd ever felt. Masturbation was nothing compared to this. My brain raced, trying to figure out how to get this girl off my cock, and get myself dressed, and yell at her, and tell her how many years of chastity she'd ruined; all while keeping anyone else from waking up or seeing what was going on. What in the hell was I supposed to do? My hands dropped to my side in exasperation as I thought through my options, and as they did, the teeth that had held me so gently in check, loosened and started to slide down my shaft. By the time they neared the bottom of my eight inch cock, I could feel the tightness of her throat pressing against the first few inches of my swallowed dick. She had my entire shaft all the way in her throat, had stopped breathing, and was now jabbing my cock repeatedly that last few inches into the back of her throat, tighter and softer than I could have ever imagined.

After what seemed like 30 seconds of the most intense pleasure I'd ever felt, she let my cock out enough to breathe and I could hear her gasp a few deep breaths. I tried to pull my hips back and free my dick from her mouth, somehow escaping the situation. If I could free myself, perhaps I could sneak out the door, naked as I was, and regain my composure. But as soon as I tried to pull away from her, I felt her hand tighten around my balls. She literally had me by the balls. She didn't squeeze them too tight, or pull on them, but again I knew that this was a game of chicken that I couldn't win. All she had to do was scream and there would be a dozen girls seeing me in their room half-naked. Would they think I was a pervert, or masturbating to them? Could I be accused of trying to rape one of them? I was stuck.

She slid her mouth back down onto my cock, her tongue bathing and swirling around my dick as she did. There was nothing I could do. I lay there helplessly, as some girl plunged my cock into her mouth again and again. Her hand went from forcefully grasping my balls, to gently massaging them as the continued to ride her head up and down the entire length of my cock. Her other hand lightly grasped the shaft just below her mouth and tugged slippery wet circles as her lips and mouth played along the head of my dick that was practically near bursting. The velvety smoothness of her mouth, and the alternation between gentle sucking and smooth sliding thrusts of her head were more than I could handle.

The weeks of abstinence I'd had after masturbating to my sister had been pressure enough, and the feeling of my first blowjob was quickly building. I could feel my balls tighten in her grasp as her noes touched my belly, my cock buried completely in her throat again. It was too much. I felt my balls start to churn, and I reached down, grasping two fistfuls of hair. But his time, instead of trying to pull her off me, I used my grip on her hair to slam her head forcefully further down onto my cock. I felt her throat convulse around the head of my cock, so slippery and tight and hot all at once. She pulled up just enough to get one deep gasp of air, and together we drove her head down onto my cock as far as it would go. My body tensed, each muscle pulling tight, and my head pulled back against my shoulders. My entire neck and head went numb as I felt myself shoot that first load of cum deep into her. My hips bucked my cock into her throat over and over again as I shot load after load directly into her throat. I cummed harder and longer than I ever had while masturbating, and the sensations all seemed exponentially more powerful. I could feel her throat grow tighter as she swallowed each burst of cum, and then she pushed my cock deeper into her throat until the next spurt came. I rolled my head back, completely overwhelmed by the sheer pleasure of what was happening. Lights were exploding in my head, and I was softly grunting, careful to not wake anyone who would turn on the lights and find me not only cumming into one of their friend's mouths; but now tightly gripping her hair as I aggressively pumped load after load of cum right into her throat. This was no longer against my will. I was taking the release that I craved so badly. She pulled completely off for another breath, and she loudly whispered: "NOW!"

Her lips wrapped around my cock again, and I felt one last dribble of cum get sucked into her mouth, when a bright flash of light filled the whole room. In that one brief instant of light, I saw another girl kneeling just to the side of me, her phone in front of her face, and realized that the light was the flash of her phone's camera. She had just taken a picture of my cock cumming into her friend's mouth, hair gripped tightly in both of my hands.

I froze in shock, still overwhelmed at the feeling of the most powerful orgasm of my life still washing over me, and the realization that I'd not only done something I would never do, but that there was now proof. My hands went limp. My eyes had been blinded by the flash, and I could feel the girl who had just sucked my dick, climb quickly from between my legs, and I could just barely make out faint footsteps and the rustle of a few sleeping bags over the noise of the fans. I sat up stunned.

Had this really just happened? I found my pants around my ankles and pulled them up. As my eyes readjusted to the dark, I tried to look around. It was too dark to see anything, and I couldn't make out the dim lights of any phone. I listened carefully but only heard the steady breathing of a dozen beautiful girls asleep. I knew two of them, at least, were not asleep, but I had absolutely no idea what to do about it.

I stood up and opened the door to the boathouse. The moonlight from outside filled the room. I looked over my shoulder and saw nothing that might indicate that anything unusual had happened. They all appeared in peaceful slumber.

I walked out and closed the door. I took small slow steps up the stairway to the house, not sure what to do or what to think. Was that the best thing that had ever happened to me? Was that the worst? I knew I should feel shame about what had happened, but it clearly wasn't my intention, or my fault. I felt guilty for having enjoyed it so much. I ran through scenarios of what I should have done, or what I could have done.

By the time I made it back to my room at the main house, I had thought of so many other ways I could have dealt with the situation. I dropped into my bed, exhausted and spent. My body still pooled with the adrenaline of my first real sexual experience. My brain reeled, and through tears I eventually fell asleep, late into the night.