Here are 8 sissy caught stories for you:)

1/8 Sissy Caught Stories – PLEASING THE HEAD

A sequel to “Boys Will Be Gurls”, Pleasing The Head continues the story from the next morning.

*

I woke up the next morning a little groggy, I hadn’t had much exposure to alcohol before and wasn’t enjoying the after effects. For a second I didn’t remember what had happened the night before, then it all hit me in a rush.

I had dressed up like a girl to be my best friend, Will’s, date for the dinner, one of the other boys, Charlie, had flirted with me and we had danced together. We had ended up grinding on the dancefloor and had both got excited, running off to the gardens where we had kissed. But the pièce de résistance was that I had wanked him off, letting him cum on me before he raced off back to the dinner.

I lay back on the bed, the most surprising thing about it was that I didn’t care, in fact I had enjoyed it and was oddly proud of having made Charlie cum. I vividly remembered the sensation of his hard cock in my hand, the feeling of it pulsing when he came, the sight, the smell and taste of his cum.

I was starting to get excited, my own dick stirring in my cum stained panties, I chuckled, oh yeah, and at some point during all of that I had been so turned on I had cum without even touching myself.

I ran my hands down my body, and began gently rubbing myself through my panties, not wanking not yet, working up to it, slowly. Unlike with poor Charlie, I wanted to take my time. I laughed to myself, poor Charlie, he had cum like a geyser even if he hadn’t lasted long, maybe next time…

I stopped, there wouldn’t be a next time, Charlie had gone to the garden with Harriet, not Harry and Harriet didn’t exist, not really. That might be the only time I got to be Harriet, the only time I would do THAT…

It was just as well, I had stopped touching myself, because the door to my room swung open and Will barged in, red eyed and pale, he plonked himself down on the bed next to me as I quickly rearranged the covers to hide my panties and my erect cock.

“Oh man, I feel rough? Do you remember what happened last night? I woke up on a bench downstairs.”

Not waiting for me to reply, Wll levered himself up and started going through my bedside table.

“Have you got any headache tablets? I think I’m dying”

I lay back, Will was such a dick sometimes.

“Yeah, second draw I think.”

He found them, downing a handful with a swig from the glass on the table before lying back on the bed, next to me, but on top of the covers. He looked around the room, surveying the devastation, there were clothes everywhere and in the corner my vintage green dress, even from across the room I could see the stains on the front, hopefully Will wouldn’t notice.

“So did it work?”

He wasn’t even looking at me, he was laid back with his eyes closed, probably nursing the mother of all hangovers.

“Seems so, though I’m not surprised you don’t remember.”

He didn’t answer for a second. “I’m guessing I got really drunk and was a complete dick.”

I uh-huh’d

He sighed, “Sorry dude, I know you really… what you did, I’m really grateful, sorry I wasn’t more appreciative.”

I smiled, “You’re welcome… dickhead”

We both chuckled.

“Harry?”

“Will.”

“Were you wearing panties when I came in?”

I coughed, “Yeah, I was too smashed to take them off last night.”

Will chuckled, “That’s so gay.”

I hit him with a pillow.

The next couple of days were surprisingly normal, back to the routine of before. I went to class, hung out with Will, went to the various clubs I was a member of. In drama the teacher asked me if I’d seen a wig that had gone missing, a brunette one with a short pixie cut. I had, it was still in my room, but I couldn’t tell him that so I lied.

Then the dinner caught up with me, I was given a message in Math class, I had to go and see my housemaster, Mr Stepleton.

Mr Stepleton had intercepted a parcel I had ordered, it had contained my bra and panties, but I had paid for it with Will’s card so it had been addressed to him. When Mr Stepleton had spoken to Will about it, he had dumped it on me, saying I had borrowed the card and he didn’t know what was in the parcel.

I was stood outside his office waiting for him, understandably nervous, was i going to be suspended? Expelled? Would he call my parents?

He came up the hall, carrying a pile of papers, he was a tall man, probably around 6′, he towered over me, he was a big man, quite fit he coached the school rugby team, but was carrying a little extra weight, he shaved his head to hide the fact he was going bald and always seemed to have a 5 o’clock shadow. He had rolled his sleeves up, but still had on a tie, he looked like he should have been a farmer rather than a professor.

However, the most noticeable thing about Mr Stepleton was his voice, it was deep and he spoke with a slow yorkshire drawl, it was a calm voice. “Mr Cabot”

My name is Cabot, Harry Cabot and at my school everyone is a Mr.

I stood up straighter “Morning Sir”

“Settle down, you’re not in trouble, just let me get in my office and we can get started.”

He juggled his pile of papers so he could get his key and open the door, leaving it open he dumped the papers on his desk, gesturing to a chair as he made his way round to sit in his own.

“Now Harry, this is… well it’s…” he looked up, directly at me “a bit fucking awkward.”

All the boys like Mr Stepleton, he treated us like adults, he could be hard but was fair, it was odd that one of the strictest teachers was also one of the most popular.

I nodded, not wanting to speak in case I incriminated myself.

“I expect Mr Hythe” that was Will “has informed you I checked a parcel addressed to him the other day, that apparently contained items for you.”

“According to Mr Hythe you ordered the items with his card, with his permission.”

He was looking straight at me

“Is this true.”

I didn’t answer straight away, I couldn’t think of what to say.

“I’ll rephrase, is Mr Hythe selling me a pack of lies and should I be dragging him in front of the Head?”

I swallowed, my mouth suddenly dry “No, Sir.”

He raised a hand, “You’re not in trouble, the… items aren’t unallowed, they are just… unusual.”

I hung my head, not wanting to look at him “Harry look up.” I raised my head but couldn’t look at him “Harry, I want to be having this conversation as much as you.”

I managed to raise my gaze to look at him, he wasn’t angry or disgusted just a little embarrassed.

“I just need to know if you are ok?”

I nodded and he smiled “There, progress. Do you mind if I ask you some questions?”

I gulped slightly but nodded.

“I’m assuming from your reaction to all this the items are for you.”

I nodded.

“How long have you been wearing women’s clothing?”

I didn’t know what would be the best thing to say, so I was honest.

“They were the first things I got Sir.”

He nodded as if that made sense, “Okay, and forget the Sir for now. Why did you use Mr Hythe’s card? Does he know?”

I thought about it for a second “I didn’t have any money on mine so Will lent it to me but he doesn’t know what I used it for.”

He made a scribble on a piece of paper “Ok Harry, I’m just going to come out and say it, I’m a little worried about you and I have no idea what to do. I don’t feel telling your parents would help anything.”

I nearly leapt out of my seat, “So, I’m not going to tell them, but I want to make a deal with you.”

I settled back in my chair and nodded, I felt like I had been nodding a lot. “I want you to talk to someone, let them know how you are feeling?”

I nodded again, “OK.”

“You can talk to who ever you want, if you want to talk to a member of faculty I can set it up for you.”

I piped up “Can I talk to you?”

He seemed taken aback, but he nodded. After a moment he spoke.

“So Harry, how have you been feeling?”

And I told him, I started off talking about dressing up, how it made me feel, how much I enjoyed it, then I told him about the dinner, I didn’t tell him why I had gone with Will and he didn’t ask, but I told him about Charlie, though I didn’t use his name. I told him about the feelings of shame and how they had stopped.

He didn’t interrupt, he just sat there listening all the way through. I talked for ever, I hadn’t realised how much I had needed to share, to unburden myself of all that had happened. We arranged that we would have regular meetings and I would keep him up to date. When I was leaving, he asked me on question.

“Are you wearing panties now?”

I nodded.

My chat with Mr Stepleton had made me feel much better and I resolved that while Harriet couldn’t come out and play, I could dress in private.

Because I was part of the drama club, I had a key to the drama room, so I moved most of my supplies in there and spent a couple of evenings dressing up, using my own dresses (including my stained green dress) and the costumes, as well as make up and a wig. The sessions would always end the same way, with me jerking off thinking about Charlie and garden.

I saw him around school, but avoided him, deciding it was too much of a risk he might recognise me. Unfortunately someone did recognise me, just not Charlie.

I went down to the drama room as normal, but when I went in I could see the light was on in Mr Harding’s room. Mr Harding was the head of drama and the worst thing about it, he was just mean and one of the least liked teachers. He tended to choose a new victim every year and bully them mercilessly, he had always be ok with me but I made a point of keeping on his good side.

His door opened and he stood in the doorway beckoning me over. “Cabot, in my office.”

I scuttled over, nervous, I was wearing gym kit with my panties underneath, I had even put on the padded bra I had worn to the dinner thinking it would be dark enough no one would notice.

He was stood leaning back on his desk a I came in, arms crossed. He gestured to a chair directly in front of him so I sat in it, though it was uncomfortably close, forcing me to crane my head up to look at him.

He was average height but still taller than me, overweight, with his thinning hair combed over trying to hide his bald pate.

He didn’t say anything for a while, nervous I spoke first.

“Sir?”

He blinked as if seeing me for the first time, “What should I call you?”

“Sir?”

He seemed somewhat contemplative when he answered “Well I can’t call you Harry, can I?”

After a pause, “Can I?”

Teachers were meant to call students Mr whatever their surname was, some didn’t but Harding was a stickler for it.

“No Sir.”

He looked down at me, “No, because Harry is a boy’s name, and your not a boy are you?”

Everything froze, my heart sank, he knew, I didn’t know how but he had to know.

He produced a phone a started swiping, he showed me the screen, they were pictures of me in various states, in womens clothing, in make up, touching myself, the last picture wasn’t a picture, it was a video of me wanking myself off wearing a girl’s gym kit.

He tutted “Well, if you’re not a boy, what are you?”

I shook my head on the verge of tears “I don’t know”

He slapped me, it wasn’t hard but I wasn’t expecting it “I don’t know Sir.”

I stammered but repeated it as quick as I could.

Leaning back against the desk again he continued “Well I do, you are a faggot.”

Tears started rolling down my cheeks. He reached behind him and pulled out a girls gym kit, judging by the stain on the pleated skirt it was the one I had wanked in last night.

“Get dressed, hair, make up, everything.”

I did as he told me, not allowing myself to think, burying myself in the now familiar patterns of dressing. I dried my eyes and carefully did my make up, using a wig that was on the desk.

When I was done, I turned to Mr Harding, unable to speak.

“Now that’s better, what should I call you?”

Without thinking I replied “Harriet.”

He chuckled, “Not very original, but it works. Harry the faggot and Harriet the… Slut.”

He was looking straight at me as he said the last word and I shuddered, causing him to smile more.

“Do you know what sluts do, Harriet?”

I shook my head, but I didn’t think it would be pleasant.

He smile spread into a grin and his hand undid his fly, “They suck cock.” he pulled out his hard member, pointing it straight at me.

Neither of us moved, I stood there, looking very much like a schoolgirl, while he stood holding his dick. I refused to look down, I refused to look at it. He held it in his right hand, gently stroking it, while with his left hand he brought up the phone again and showed me the pictures.

I was beaten and we both knew it, he didn’t even need to say anything. I was trapped, I couldn’t even runaway dressed like a girl in a cum stained skirt. I stepped forward and silently sank to my knees in front of him, he moved his hand away and I could see his dick for the first time. It was bigger than mine and bigger than Charlie’s it wasn’t long but it was thick, with big veins running down it towards the head that mushroomed out from the shaft making it even thicker.

I looked up at him again in time to see the flash of the camera on his phone as he took a picture, his dick and my face looking up at him in the same frame. I couldn’t see his face behind the phone but I could picture him smiling.

He rocked his hips forward slightly, bumping the head of his cock against my lips. I shied away slightly, looking at it, throbbing in the air. If I am honest I had fantasized about giving a blowjob since that night with Charlie, but I hadn’t thought it would be like this.

I reached my tongue out, tentatively touching his spongy head, tasting it. It didn’t taste of much, I moved closer, using my tongue again but this time running it over his hole, testing the taste again. It was subtle, not like I had imagined, I didn’t know what to expect, but this wasn’t it. I moved even closer, putting the head into my mouth, sealing my lips around it and dragging them back until it popped out.

He wasn’t saying anything and I couldn’t bear to look up, so I carried on. I put my lips around him again and gently sucked as I moved back. I had never given a blowjob, or received one, hell I hadn’t even seen one in a porno, but I had other boys talking about them and that despite the name, you didn’t blow, you sucked.

I did this a couple more times, eliciting a groan, I looked up, the head still in my mouth, the flash went off again. I knew exactly how I would look, I had seen images like that in a magazine, the girl, her mouth full of cock looking up into the eyes of her lover. When I had seen it, I thought it was incredibly sexy, but now I was that girl.

I repeated the motion and he thrust gently towards me, causing me to go deeper every time, I was careful not to scrape him with my teeth, something else I had heard from the other boys. Soon I was struggling, I was going most of the way down with each thrust, but he was pushing against the back of my throat, causing me to gag slightly, my mouth filling with saliva.

“Use your tongue.”

I looked up again, this time looking into his eyes rather than the lens of a camera.

“Use your tongue, when it is in your mouth.”

I had to think about it, but started to swirl my tongue round the head while it was in the front of my mouth. I was rewarded with a strained “Fuck” from him.

He pushed me away gently, pulling his cock out of my mouth, he held it, pulling up against his belly, exposing his heavy balls.

“Lick them, suck them into your mouth.”

I did as he asked, licking his balls, making them glisten with my spit before sucking them into my mouth one at a time. I was so close I couldn’t avoid his musky smell, he wasn’t dirty or sweaty, but it was quite a strong smell, I guess it was what men smell like, I decided I liked the smell.

As I wa doing this he let go of his dick, letting it fall, gently smacking me in the forehead, leaving it lying across me as I worked on his balls. His breathing was becoming more strained.

He pushed me away again, pushing his dick down, the tip dragging across my face on its way back to my mouth, I parted my lips for him and he pushed inside. He started thrusting into my mouth, holding the back of my head, keeping me in place.

“Normally I would make this last longer, but I want to come.”

He was steadily fucking my face now, slowly building up steam.

“Play with my balls.”

It took me a moment to figure out what he meant, my hands were braced on his hips, for stability and to stop him pushing too far, but I used one of my hands to cup his balls, gently massaging them, I was careful to be gentle, I knew how sensitive they could be.

Despite the situation I was getting turned on, I moved my other down, lifting the skirt and rubbing myself through my panties. He was getting faster and faster, I was trying to do everything at once, suck, use my tongue, mind my teeth, in the end I just knelt there as he fucked my face, slowly playing with his balls inside their pendulous sack.

He started grunting and I could feel his balls tightening in my hands, he carried on thrusting as his penis became solid, hard like an iron bar, before it started spurting. I could taste his semen, it was coating the inside of my mouth, mixing with the saliva.

He pulled back, pulling his penis out of my mouth, I went to follow it but the hand at the back of my head pulled me back by my wig and the last of his cum was spread across the bottom half of my face, I tried to say something but all that happened was I choked and the sperm and saliva mixed in my mouth ran down my chin and onto my top.

Using his hand on the back of my head, he twisted my head round so I was looking up at him again.

“A good slut swallows, but we’ll make allowances for your first time.”

He leant down slightly, “It is your first cock, isn’t it? Slut”

I didn’t think Charlie counted, not after what had just happened, so I nodded. He smiled and brought his other hand round with the phone in it, the flash went off again.

“Well now you’ll have something to remember it.”

It was then, he noticed my hand underneath my skirt, moving, touching my own hard cock. His eyes narrowed, “clean yourself up, lock up before you go.”

He pushed his messy cock back into his trousers, zipped up and left without another word. I knelt there covered in his cum, wanking furiously until I came. I brought my hand covered in my own cum to my mouth and licked it off my hand, my cum and his cum mixing in my mouth. I could see myself in a mirror in the corner of the room, hair and makeup disheveled, covered in cum. He was right, I did look like a slut.

Mr Harding had said it was my first time, but I didn’t think it would be my last time and I wasn’t sure how I felt about that.