[Humil][chastity] Innocent naive college virgin wins a sorority’s life time virgin award. His prize isn’t what he thought it was.

I was homeschooled by my overbearing mom until college. She wasn’t religious, but she was as sheltered and naive to the world as one could get. It was never something I thought about growing up, just as a boy doesn’t know what something is, like a combustion engine, until he’s told of its existence, I didn’t know about sex. I was aware people had it, it’s how babies were made, but outside of that, I was clueless. I never thought it’d be a prominent factor in my life. Boy was I wrong.

I started college at one of the largest universities in the country. Unbeknownst to me, also the largest party school. I found this out via a sorority event believe it or not.

At the time I was unaware, but apparently during pledge week for the major sorority, the pledges are given the task of finding a virgin and bringing them to a party. Like a dinner for schmucks type situation.

So when a beautiful blonde girl, who was dressed, revealing more skin than I had ever seen on a girl my age, asked me to come with her to a party, I wholeheartedly agreed. In my mind, this was the first step to meeting my future wife. Due to my sheltered life, my mind went straight to marriage, oblivious to how dating really worked, especially in college.

I showed up to the party later that night, dressed in a button up shirt, slacks and holding flowers. The head sorority sister; Angela, answered the door, not Brittany, my date. She was clearly intoxicated, and had started laughing when she opened the door, I assumed it was because of something someone said.

I was led inside and downstairs to a room filled with 12 other guys my age. I was a little excited as they all looked like people I could be friends with. One was in a star trek shirt, the other reading a book, most of them seemed interesting, though noticeably out of place at a party. I walked over and started talking amongst them.

Some time went by and I had completely forgotten about Brittany, until the basement door opened up and a row of girls walked down. Brittany was among them; she was absolutely beaming at me. She was nudging the girl behind her and motioning towards me, all the while with a big excited smile on her face. It made me elated to see I made her that happy.

The head girl, Angela, asked us to line up and for the sorority pledges to stand behind their date. So there I stood, with Brittany standing right behind me in her tiny blue dress that hugged her every curve and outlined her tight petite tits. I felt her hand on my shoulder and some of her hair brush against my neck as she leaned in and whispered in my ear “whatever they ask, just do it, if we win I’ll make it worth your while.” I felt a wave of warmth overtake me, it was the sexiest thing to have ever happened to me. I was so focused on this new feeling, what I now know to be horniness, I hadn’t noticed me getting erect. I wouldn’t have noticed either if it wasn’t for Angela exclaiming “oh my God, no wayy! Looks like we already have a winner for round one!” She was standing, mouth agape, and pointing at my crotch. I looked down, mortified to see my pants lifted to a point, with the only explanation being my now erect penis.

“Normally round 1 we have the girls do their best to get their dates hard without doing anything sexual. But it looks like someone is a step ahead of us”

“Good job babe!” Brittany whispered loudly in my ear. I felt my erection twinge with excitement.

“Okay now for round two! We all know the saying ‘size matters’. Well let’s see whose taking round number 2!” Angela shouted, pacing back and forth, inspecting each of us.

I had no idea what was going on. I was fixated on this feeling of elation, this horniness and consciously ignoring the sense of humiliation. I was so set on enjoying this ecstasy, this new arousal, I didn’t want to worry about anything but keeping it.

Brittany was back in my ear “babe, drop your pants. Pleaasseee, they do this every year. It’s nothing anyone here hasn’t seen before, just real quick pleasssee!” As she finished her sentence, I felt the warmth of her breath and just seconds later, her tongue, running around the brim of my ear. I shuddered as waves of that warmth carried down my body.

Before I knew it, I was fighting my belt and dropping my pants to reveal my fully erect penis. I look over and see several other guys with their pants down and their cocks exposed. One kid seemed to be arguing with his date, before he loudly said No and walked out.

“Oh what a shame! Looks like you lose Tiff, better luck next year.” Angela chanted as Tiff broke down in tears and ran out.

Before I knew it Angela was walking down the row with a ruler. It didn’t take long for me to figure out it’s purpose. As soon as I realized this, I started scanning the other guys in the row and started to get nervous, borderline scared. Every other guy was different sizes, but all of which, were decidedly larger than me. This was confirmed as Angela moved down the line, each time announcing the length of the guys cock in front of her.

“5 and a half… ooh, 7… 4… And now, the winner from round one…. oh my.. 3 inches. Looks like we have our winner folks! Back to back rounds, Matthew is our winner. Give it a round of applause.”

I stood there with my pants around my ankles, a row of guys smirking and a room full of beautiful girls cheering. It felt wrong but I couldn’t help but remain enveloped in blissful arousal. It didn’t hurt that each time i won a round I had Brittany in my ear.

This competition went on for a couple hours and I somehow won every round. The final round, when it was left between just me and one other guy. Brittany was in my ear, telling me how much she wanted me and intermittently licking my ear. After just a couple rotations of this, I found my knees locked and back arched as a wave of heat and pleasure jolted through me and erupted out of my erect penis onto the floor.

They announced I was the winner and I asked what I won. “You’ve won the grand prize of the lifetime V card member. How excited are you?”

Coming out of my arousal fueled ecstasy I was a bit confused, but wanting to match the energy in the room I excitedly told them I couldn’t wait.

After some laughter, Angela pulls out a sheet of paper and tells me to sign at the bottom for my prize. Unsure what a v card was, but excited at the sound of it I sign away.

If you’ve ever heard someone say to read a contract before signing it, they’re right. It took me a bit but I finally found out what that contract was. It was signing up to be a life time virgin.

They brought me upstairs and led me into a dark room, sitting me down in a weird leather chair. Before I knew it, leather bands were wrapped around my hands and legs so I couldn’t move, and Angela was standing in front of me.

“Alright listen up. This is stage one. I call it initiation. I’m going to ask you questions and you’ll answer them honestly.”

The feeling in the room had changed. At first it was playful and fun, but now, now it was tense and intimidating. I felt nervous and worried about getting in trouble as I was completely vulnerable.

“How much porn do you watch?”

“Um. None actually. I was homeschooled and have never looked at it.”

“Oh my god, really? You’ve never looked at porn?”

“No I swear”

“Okay, perfect then. This probably won’t take long then. Just sit back and enjoy. Brittany will be in to check on you intermittently. Good luck” and with that she was out of the room and I was alone, strapped to this chair alone.

Suddenly the wall in front of me turns into a blinding wall of white. It was a projector screen. The white flashed into the picture of a beautiful blond girl, completely naked. It flashes again and it’s the same girl from before but this time drawn back more so I could see her face. I was stunned to see that it was Brittany. There she was, completely naked staring right back at me. I felt that arousal wash back over me and my penis stiffen. The screen flashed again and now there was a picture of a different girl on the screen, this one also appearing naked. But this time, where her breasts and pussy was, was instead large black censor bars. Their sexiest parts blocked out. The screen flashed and a different girl was on the screen, her also censored just as the one before.

Over the next couple hours I sat there watching image after image flash on the screen. The only fully nude pictures were those of Brittany and every one else was censored. I started off hard right away, but over time I would keep getting soft after long periods of only censored pics, my erection always to return when the rare naked Brittany would appear.

I must have been in there for a couple days. When they finally pulled me out of the chair, my legs were weak and my balls ached like I’d have never felt before. As they pulled me out into the hallways my eyes stung from the light. When they finally adjusted I was sitting in one of the girls rooms.

I sat rubbing my eyes for a couple seconds before the door opened and in walked Brittany. She was wearing a pink and white polka dot bikini. She walked right past me without even acknowledging me. I wanted to say something but I couldn’t. As I opened my mouth to say something, i lurched my neck as all my muscles tensed up. I felt my ass cheeks clench as a warm heat erupted from the throbbing in my balls and rushed through my almost instantly erect penis, forming a large circular stain on my pants.

I was speechless. I sat there confused and like a deer in the headlights. As soon as I saw her, in almost an instant I was overcome with pleasure and arousal and came almost instantly.

Brittany was now looking at Me and laughing.

“Oh my. That’s fucking embarrassing. Here get out of those I have something for you to help”

Without thinking I stepped out of my pants and stood there half naked in front of her. She told me to close my eyes. I did.

Soon after I heard some clunking and then all of a sudden a cold solid thing was pressing against my balls and flaccid cock. Brittany insisted I keep my eyes closed. Before long I feel a considerable weight on my entire groin and a cold solidness to it. I open my eyes and see a small pink plastic tube like thing covering my dick. I stumble back muttering a question as to what that was.

“Well you see. We know you can be sure you cant exactly get a girl to sleep with you on your own, but we can’t be sure you won’t have sex with yourself. So this chastity cage will ensure that. It’ll also stop you from ruining every pair of clothes we give you.” She was smiling diabolically at me and after dangling a tiny key in front of me, walked out.

Over the next month I spent my time cleaning the house and doing whatever the girls asked of me. I was promised if I did good they would let me out of my cage and let me enjoy some “freedom”.

The thing that was hard though, was that these girls would have parties all the time. And as I wasn’t allowed at the parties I would have to stay in one of the girls rooms and not move. Sure enough, sooner or later a girl would come back to their room. Often with a drunk guy, and proceed to have loud drunken sex right there in front of me. I would be sitting there, almost in tears as my cock strained against my cage, watching the entire thing.

Finally the month ended and Brittany told me I had been a good virgin and that I could have some freedom time. She told me to go to her room and lock the door. I was told the key would be there on the counter and I could have the whole hour to myself.

Excited, I ran upstairs and into her room, locking the door behind me. I had been looking forward to this all month. Just the thought of it caused my cock to strain against the hard plastic.

As I turned to look for the key, as my stomach sank in a pit, I saw on the desk a giant cube of ice. And there in the middle of it, the key. I sat there rubbing my hands on the ice till they hurt, and doing everything I could to help melt the ice for the entire hour. As I was maybe an inch away from the key, Brittany busted in through the door and broke out laughing. She mocked me for not being able to melt the ice, and how sad and defeated I looked. She told me she felt bad for me, and that in order to make me feel better shed give me a treat.

With that, she undid a latch on her top, and her shirt fell forward, revealing her perfect B cup tits. Before I could even put a name to what I was looking at, i felt the skin of my cock tug on the edges of the small openings in my cage, followed by a flood of heat and a stain growing on my pants.

“Hahaha you fucking loser. I guess we don’t even need to take that thing off anymore. Angela! It’s time for stage three!”

Source: reddit.com/r/eroticliterature/comments/6zrrxt/humilchastity_innocent_naive_college_virgin_wins