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.
