Guilty Pleasures

“What do you think Jodie?”

“What?” I asked. I was deep in thought and hadn’t heard a word Kandi had said.

“About this new announcement from the Dean,” Kandi exasperated. “Look, I’ll read it again:

It has come to my attention that some of the girls of this college have been raising issues with the sexual excitement punishment of consensual rape. A few have claimed that they have been unfairly raped more than once for the same violation due to ending up completely naked after an inspection with all their clothes removed and not having anywhere to put their citation tickets that prove they have already been inspected. Thus with no pockets, some of these girls have lost their tickets and come across another inspector who duly performs his duty and in the process, finds the girl sexually excited (not knowing that her excitement is the vestiges of her previous inspection) and thus rapes her all over again. The girls report that the worst part of all is that they are made even later for the lessons they were on their way to. To address this issue of class punctuality and lateness, I am announcing a trial variation to the consensual rape punishment for one month: Any inspector consensually raping a girl vaginally or anally must ejaculate as deep as he possibly can inside her. The girl being raped is not to wipe away any of the inspector’s ejaculate. She must allow his seminal fluid to trickle out of her and dribble down her leg for the rest of the day. That way, if that girl is stopped by another inspector, he’ll see the previous inspector’s cum trail and know that the girl has already been dealt with. – The Dean’

“Great! This will sure help me out. I lost my citation ticket once and was consensually raped four times in a row by four different inspectors! The last three each refused to believe that I had already been inspected previously,” Bonnie said.

“Well of course they didn’t believe you otherwise any girl could say that and lie their way out of an inspection,” Camilla said.

“I’ve had cum trickling out of my arse before and I didn’t find it at all comfortable, having that soggy wet feeling dribbling from your bottom. How are we meant to sit down in lessons?” Kandi asked.

“Well since we’re not allowed to wipe it off, maybe we have to stand until it dries on us.” Ella stated.

“But that could take ages!” Daryl exclaimed.

“Probably not that long in hot weather. Anyway, if we do have to wait for the cum leaking out of our pussies and butts to dry before we can sit down, it will serve as an extra deterrent not to be caught in violation in the first place!” Kandi said. “What do you think Jodie?”

I only heard the beginning of what Kandi had read and then drifted off into my own thoughts again because I had a problem that needed solving. I had met up with the girls for mid morning break as usual but didn’t feel like sharing my predicament with them.

I woke up this morning feeling rotten. I was feeling so guilty, all because of this boy called Luke. I met Luke two years ago when he was new to the college. Straight away he fancied me a lot. He was, and still is a very shy and timid person but he finally plucked up the courage to ask me out about a year ago. As I was really trying to concentrate on my studies, I had to decline. We remained good friends but he never again spoke of his feelings for me. Over these last two years he has always been very nice to me; regularly tutoring me in math lessons and generally helping me out with anything I asked even when it was an inconvenience to him.

I had not realised this but over the last year, my requests for his assistance had become more and more demanding but he never refused once. I suppose I had been subconsciously using the fact that he fancied me to get him to do various things as I knew he would never say no.

Anyway, recently, I had my eye on an Armani handbag that cost $300. I was so excited, I told everyone about it. I was all prepared to save up for it but then discovered that as it was limited edition, the few bags the store had were selling fast with no more stock coming in. Being short of cash, I asked Luke for the $300 with every intention of paying him back. I could tell it was a stretch for him but he gave it to me anyway saying not to worry about paying him back. I really wish he hadn’t said that as even though I knew he most definitely didn’t mean it, it made me much less likely to try hard and repay the money.

He gave me the money yesterday morning but in the afternoon, my dad surprised me by wiring $300 into my account for the bag.

“Great,” I thought, “now I’ll just give Luke back his money, but I’ll buy the bag first since I won’t be seeing him again till later…”

That was a big mistake. While in the shop, a nice pair of matching shoes caught my eye and I ended up spending Luke’s money on them. I walked out of the shop feeling fantastic but then woke up this morning with the realisation that realistically, I would not be able to pay Luke back. I felt like an evil bitch who had only used him for his money and then kicked him to the curb.

Luke sat next to me at lunch today. He was in a good mood and said ‘hi’ but I was still deep in thought about how I was going to pay back the money I owed and I didn’t look up from my food. He could tell something was wrong.

“Are you alright?”

“Fine,” I said flatly. “Luke, do you still fancy me?”

The question completely caught him off guard and he became shy again.

“Well… you’re a nice girl… I guess so,” He mumbled.

I wasn’t sure what I was doing when I asked my next question, “Do you masturbate about me?”

He could not believe I had asked him that and looked around hoping that the floor would open up and swallow him, rescuing him from the situation. After a short while of him not answering my question, I looked at him directly and asked again. This time he could not escape my question and because he was so polite, he felt that he had to answer with the truth.

“Yes,” he said meekly.

He was extremely embarrassed now and wanted to get up and run.

“I’m really sorry, Luke. I don’t think I’ll be able to pay back that $300.”

He was so relieved I had changed the subject, “Oh no, that’s ok! I said that you didn’t have to. I can still help you with your math work,” he said hoping that I would not return to my previous subject.


“Good, I’ll meet you in the library later,” he said getting up to leave before I cornered him again.

“Instead of the library, meet me in my dorm room. It’ll be a bit more comfortable.”

Luke was a little surprised at this as we always met in the library but he agreed anyway.

With Luke being the way he was; shy, polite, meek, timid and a bit of an introvert, in the two years he has been at this college, he has never once engaged in a dress code inspection. He had always left them to the more assertive and confident boys at the college, even though he knew that not helping out the female students by enforcing the rules could land him in trouble. He was just way too shy to inspect a girl who looked like they could be breaking the code.

10 minutes before Luke was due to my dorm room, I decided to over dress by wearing a bra and panties, blouse, thick woolly sweater and a long pair of jeans.

Luke knocked on the door and I beckoned him in. He immediately saw the way I was dressed and recognised I was in breach of the college code. I could see the surprise on his face but he didn’t say anything, preferring to be subtle, making small talk about the hot weather.

After going along with his small talk for a while I realised he was never going to raise the issue of my inappropriate dress so I was going to have to do it for him.

“Even though it’s 28 degrees Celsius [82.4f], I was feeling a little chilly and thought that I’d take the risk and put on a few extra layers. Do you think I’m breaking the dress code?”

“Well… yeah.” he said, “but I won’t tell anyone.”

“But if someone else came in right now, I’d be in big trouble.” I paused, waiting for him to take the hint. He didn’t so I went on. “You’d probably be in trouble too for not bringing me up on the way I’m dressed.”

Luke was now looking very confused and wasn’t sure what to do.

“Don’t you think you should inspect me Luke?”

Now he was in a fluster, not sure where to look. I called him over to where I was standing and told him he should start with my top, “You should examine it to see if I’m in the wrong.”

He stepped in close, lightly touching my arms.

“You should feel it all over.” I said as I took his hands and placed them directly on my breasts over my sweater. He breathed out a loud sigh. This was the first time he had ever touched a girl. He started bending forward slightly and I realised that he was trying to hide from me his erection that had formed.

“The wool is quite thick,” he said.

“I guess then that you should take it off me.” I raised my arms above my head. He hesitated but then slowly lifted my sweater up and off my arms. I now started deliberately thinking sexy thoughts to make my vagina moist.

“I don’t know if this blouse is against the dress code,” he said.

“In that case, you have to take it to examine later as well.”

He unbuttoned it carefully, being extra careful to not touch my tits but I kept moving, forcing my breasts into the backs of his hands. He had now bent forward lower, trying to hide his erection that had grown even bigger. I was still thinking really erotic thoughts and my pussy was juicing up nicely.

With the blouse now off, he desperately avoided any eye contact with my boobs.

“What about my bra?” I asked, “Are we allowed to wear ones like these?”

“I don’t know,” he said quietly. He actually did know that they weren’t allowed but was feeling extremely shy about what he knew he had to do next.

“Then you’ll have to take it and examine it later too,” I said. I made him stoop so his face was level with my tits. He tentatively reached around my back to undo the clasp. Again I kept subtlety moving and when he undid the clasp, the bra fell away. My boobs sprang free and I pretended to lose my balance and pushed my tits into his face. He gasped at the feel of my soft warm breasts against his face and immediately stood up straight apologizing. I told him it was my fault then looked down at the bulging tent that had formed in his trousers. He saw me stare at his erection and apologized again.

“Don’t worry about it. It’s only natural when you’re inspecting a girl for the first time.” I told him.

I was now thinking hard, trying to imaging what his straining cock would look like once unleashed form the restraint of his trousers, which was doing a nice job of keeping my vaginal juices flowing into my panties.

He was really worked up now and trying not to move too much. The sensation to his dick rubbing against his trousers was getting to him and with all the friction, he was close to cumming in his boxers.

With me now topless, I turned his attention to my jeans, which definitely were against the rules, “I think these have to go.”

He kneeled in front of me, his head level with my stomach. He gently unbuttoned my jeans, pulled the zip down and slowly slid them down my legs. As my pussy was now very wet, the strong scent of my womanhood hit his nostrils and he inhaled deeply.

Dear god!” He said under his breath as he tried not to concentrate on the erotic smell of my pussy.

He was trembling now and really trying not to move as he was very close to cumming on the spot.

I stepped out of my jeans and stood in close to him again, now only in my damp, white panties which had become translucent with my pussy juice. My puffy vulva lips were clearly visible through the thin wet material.

“Oh, no. I’m afraid I’m wet.” I said innocently.

He gulped, still breathing in my sweet, musky scent. He knew he had to take my panties for evidence and as he slowly slid them down, stringy tendrils of my gooey pussy juice made strands from my pussy to my panties. He gasped again, this time at the sight of my shiny hairless wet slit. He could not believe how wet I was.

I now stood completely naked before him.

“So it looks like I have failed the dress code and failed to not become sexually excited during an inspection but hopefully I can pass the tactile inspection…?” I said guiding him in what to do next.

His hands were shaking as he’d never seen a girl naked before, let alone touch a girl’s pussy. He moved his right hand slowly up to my pussy. As his fingers made contact with my slippery gash, he let out another loud gasp. His hand slid all over my wet pussy looking for traces of pubic hair. I already knew he would not find any as I shaved my pussy smooth every day. After all this, he was still very shy and did not want to touch me for longer than necessary. He moved his hand away stating he could not find anything.

“Great,” I said. “One out of three’s not bad! But I did get wet. Very wet. I guess you know what you have to do next for my punishment and so that I learn my lesson?”

“Ok,” he said in almost a whisper.

He knew the punishment for a girl who became sexually excited during an inspection was consensual rape and he started to unbutton his trousers. His hands were trembling so much that he was having great difficulty undoing them. I decided to take charge and got him to lie on my bed. He was now breathing very deeply. I undid his trousers and carefully slid them and his boxers down making sure that there was no contact with his very taught cock as I didn’t want him to cum yet. His dick was ready to explode. It was twitching and jerking of its own accord. I got on the bed on my knees to straddle him and began lowering myself over his dick. With my left hand I parted my pussy lips and held his raging cock with my right. I lowered myself down onto his engorged dick and as my hot wet pussy lips slid over his plump sensitive cock head, Luke let out a sharp moan and came, spurting fountains of spunk into me, his whole body jerking and convulsing as he did so.

I lay next to him listening to him catching his breath.

My alarm clock went off reminding me that it was nearly time for my next lesson. “I have to go now Luke. You can stay for a while if you need to. I would really appreciate it if you could come back tomorrow to check the outfit I’ll be wearing.”

Luke was too wiped out to respond but he did come back the next day. In fact, Luke came back every day for the next 3 months to check that I was complying with the dress code and somehow, I always had it wrong.

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2 thoughts on “Guilty Pleasures

  1. bobblushing

    Is it possible to apply for the job of “Clean up Apprentice”…having to clean each punishment participant respectfully tidy all day, and, keep a detailed journal?


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