Dormitory Dilemmas

Now, I normally sleep naked, but with Susan being here I thought a bit of modesty might be in order, and besides, I was in a girls’ dormitory, or at least pretending to be, although it once was a real girl’s boarding school.  There was a night dress provided and so I figured I better wear that, putting it on just with my navy school knickers on underneath.

Laying in bed it took a while to adjust to my unfamiliar surroundings.  I thought about masturbating, there had certainly been enough excitement during the day, but was worried in case I made a mess of the sheets, so maybe it would be best if I didn’t.  I wished Caroline was here, not that for a minute I would think of using her to satisfy my carnal lusts, but it would at least be nice to have a cuddle, and you never know, it could lead to more, although, not of course with Susan being in the same room.  Maybe a ménage à trois?  Ah, this was not doing me any good at all. I was getting more horny and frustrated as my imagination went to work.

Just as I had resolved to get up and go and get some tissues to masturbate into, I heard Caroline and Susan coming into the room.  Phew, that was a close call.  While Caroline doesn’t mind me “taking care of myself” as she calls it, she does love to call me a little masturbator and if I’d been caught she would have been sure to have involved Susan in her taunts and no matter how playful she might be the ridicule would have been extreme in my eyes.  Best to play safe and keep my hands out of my pants.

Caroline and Susan were making a bit of noise with their chatter and I was in two minds whether or not to ask them to please be quiet, but then I caught the thread of their conversation and decided to fane sleep so I could listen in.  I must admit I got a little rush out of eavesdropping on my two female companions, my fellow students, that I almost wanted to rub myself while I did it, but I daren’t risk them  catching me or give Caroline an excuse to call me a naughty little wanker or some other taunt.

“That’s an interesting line of work, I guess.”  It was Caroline and I think they were talking about the lady who was organising the weekend and performing the role of Head Mistress.

“Yeah, there must be some perks!”

“Pricks more likely, I imagine she has to deal with all sorts” Caroline was laughing.  “And sounds like she sorts them out too.”  They both laughed and it sounded like Susan making the sound of a whip.

“What did you think of her ponygirl weekend offer?”  Susan asked Caroline, but there was no answer.  “I’d be game if you were...” Susan went on.

“Maybe” Caroline sounded a bit reluctant and as if changing the subject “What do you think of tomorrow’s timetable?  I must say I’m looking forward to it.  On theme, but nice and varied, not sure what Mar..., eh Marcia is going to make of it though.”  She chuckled and I couldn’t quiet hear Susan’s reply except that she ended by saying better tell him.

“Yeah, he’s gonna have to get up early to be breakfast monitor.”  I listened carefully hoping Caroline would say more, but then she was shaking me by the shoulder.  “Wake up dear, you’re going to be busy like a bee, buzz buzz.” With that she started to poke me until I turned over and sat up, pretending to be groggy with sleep.  The lights went on and I was worried they, or Caroline at the very least, would notice the little tent I was making, the swelling induced by the image of Caroline and Susan being ponygirls had not yet receded, especially after the recent horniness.

Doing my best sleepy impression and also trying to be politely dutiful and avoid further scrutiny, I asked what’s up.

“You, Marcia, are breakfast monitor.  We’ve all been given jobs.  I’m chalk monitor and Susan is blackboard monitor.  But then we thought we’d like breakfast in bed and so elected you dear, as breakfast monitor.  That means up early and down to the kitchen.  There’s instructions.  Simple job for you” She was patting my head, reassuring the uncertainty she must have spotted in face.  “But as it’s school property you must be dressed...” before she could go on she started laughing.  “And Susan has picked out your knickers to wear” This was burst out amid more laughter and Susan admonishing Caroline for dobbing her in.  Then it happened.  Susan lay a bright pink pair of what I could only call bloomers over my bed, just where I was supposed to wear them, only problem was they didn’t lay flat and without thinking Susan went to smooth them down and as she did so let out a shriek as she felt my little stiffie under the bedclothes.

It didn’t take Caroline two seconds to realise what had happened.  Susan started apologising, Caroline told her not to, that I must have been having a wank, that obviously I must be enjoying being a schoolgirl and should apologies to Susan for giving her a fright.

As I had my eyes shut tight in embarrassment I didn’t see Susan’s reaction, but I started apologising as best I could.  Susan still seemed a bit contrite “If I’d have noticed, I never would have ...”  Caroline interrupted “It’s very small, Susan, not your fault you didn’t notice it, hell, I don’t notice it much either, in or out.”  Caroline giggled and then Susan giggled and I realised they were both a bit tipsy.

“It’s okay Marcia, it’s just not something I expected” Susan explained.  I squirmed at this and had Caroline giggling even more which then had Susan saying “Not in a girls’ dormitory at any rate.”  Caroline then wanted to know if I was a girl or would she have to call Headmistress.  I thought it best to play a long with her and replied yes, I am a girl, trying to get a petulant school girlish tone into my voice.  I was rewarded by a big smile from Caroline and little guilty smirk from Susan.

Forced Feminisation At Boarding School

My wife Caroline and her best friend Susan had signed up for a weekend retreat that promised a realistic experience of an old English private boarding school.  The only thing was there was a minimum requirement for three pupils and so I was dragged in as well.  They didn’t tell me it was a boarding school for girls, but they had warned me that there would be some dressing up, just like in a “How to Host a Murder party”.  I had to admit it sounded interesting and the location was exceptional and the food and lodging was advertised as superior to school standards.  There was even wine with dinner.

Now, Caroline knows I like to cross dress and I guess she probably confided as much to Susan.  Either way when we arrived and I realized what was required I couldn’t back out; Caroline’s look told me she knew this was something I would enjoy regardless of any protestations on my part.  More so, the Head Mistress who greeted us, who we were to refer to as Mistress Eleanor, gave me a stern look  and after getting us into our uniforms and complimenting Caroline and Susan on their smart appearance, just said to me with a note of disappointment “You’ll just have to  do.”

There is not much you can say about a school uniform and really I suppose, apart from the skirt, it was pretty unisex.  I was almost disappointed: vest, no bra; socks, no tights; and of course flat shoes and no makeup.  Caroline and Susan wore bras and if I’d have been asked I would have said I thought that was unfair, doubly so when I later found out we would be playing tennis – the sight of the two girls playing tennis braless would have been literally boggling.

The accommodation was a dormitory, basic but certainly a lot better appointed than it would have been when it was part of an actual girl’s school.

We went almost immediately into lessons.  The first one was French and I got the feeling I’d been set up as I knew Caroline had studied the subject at school and Susan had travelled extensively in France.  My French was limited and I nervously took the French 101 book from my desk and stood to read out loud as Mistress Eleanor instructed.

Well, it was about fifteen minutes of Caroline and Susan giggling and laughing as Mistress Eleanor continually corrected my pronunciation of the text.  Finally she gave up and told me I was a stupid girl and proceeded to put a dunce’s hat on my head and lead me to the naughty corner.  I was quite mortified by this and listened in silence as first Caroline and then Susan read aloud without any trouble or correction. Mistress Eleanor then dismissed them for morning tea which I later found out was a nice spread of coffee and cakes brought in from a local tea rooms.  I however had to stay in the naughty corner and be content with a glass of water.  Mistress told me off for pouting and that if I had been a better girl I wouldn’t be missing out.

For the remaining lessons we practiced calligraphy, studied domestic science and did some embroidery before games in the afternoon.  Of course my hand wasn’t the neatest and so I had to wear the dunce’s hat again.  My cooking skills also were not up to par and I was left to eat my rather dull scones for lunch rather than the nice looking sandwiches that the others enjoyed.  They also had juice, but I just had water again.

Most of the afternoon was given over to games which turned out to be Caroline and Susan playing tennis while I had to “pretend” to be the “ball boy”; something that they thought was very funny and even Mistress Eleanor had a few laughs, particularly went Caroline chided that I had to pretend as I wasn’t a boy as I was at a girls’ school wearing a skirt and that anyway, I didn’t have any balls.  I blushed and was further shamed when Susan smiled as Caroline lifted up her little finger in the time honoured indication that I had a small penis.  I’m not sure what Mistress thought of this behaviour and I almost expected her to tell the two of them off, but instead she chuckled and said that maybe a girls’ boarding school was the best place for me.  

Caroline and Susan playing tennis was actually fun to watch.  They had changed into sports bras and tennis shoes, but still had on their school skirts.  Those skirts would fly about as they swung their rackets and I would get lovely glimpses of their knickers, ugly school girl knickers it is true, but it was still pretty sexy, especially when Caroline would comment on it, shouting out: “Saw your knickers!”  “Break an elastic!”  Susan was a bit prudish to start with, but her competitive spirit overcame her modesty and forced Caroline to concentrate more on her game and less on her taunts.  I enjoyed the display and the exercise in running after the balls was good.  It certainly beat sitting in the dunce’s corner.  However afterwards it was a bit embarrassing when Mistress Eleanor told me off for displaying my knickers as I was fetching the balls which had Caroline and Susan in fits of laughter.

It goes without saying that my sewing was a failure.  Mistress Eleanor told me I would be repeating the task for homework, at dinner time.  So, there I sat, dunce’s hat on my head again, dinner getting cold, sewing my name, “Marcia” onto a handkerchief.  Each time I finished stitch I had to recite my name and it became quite hypnotic and soothing.

Caroline and Susan had finished the wine by the time I joined them so I had to content myself with water again.  I must say the catering was superb, not that I got to enjoy any of it much.  I suppose in that way I was getting more of a real experience of what it was like at a girl’s boarding school.

Mistress Eleanor came to check on us and enquired how everything was going.  Caroline and Susan said they were having a great time.  My opinion wasn’t sought, but as I sat squirming, Mistress Eleanor snapped “What is it Marcia?”

“Please Mistress may I use the bathroom?”  Caroline and Susan burst out laughing and as a result I didn’t hear Mistress Eleanor’s response and so had to ask again.

“You really are a stupid girl.  The answer’s now no.  Not until you go to bed.”  She stood looking at me and could see I was desperate.  “In fact it is best if you go to bed right now you silly girl.  Give that empty space in your head some rest.”  Shame faced I made my way hurriedly to the dormitory and rushed to the loo, leaving Caroline and Susan to an enjoyable night of watching some TV and possibly having an adult conversation with Mistress Eleanor about what they expected on the second day of our weekend stay.

sissy in Bondage

Mistress puts me into bondage.

She gags me, a ring gag, blindfolds me.

My ankles are cuffed, and my wrists.

She puts me onto my knees, and pushes my face into the carpet.

I kneel, and she pushes a butt plug inside me.  Then she turns it on.

“Kneel tiffy.  And don’t move.”

I kneel, and I hear a click.  Even with my mask on I can sense the light has gone out.

It goes quiet, and I’m not sure if she’s still in the room.

I move my weight slightly.

“Don’t move tiffy.  I didn’t say you could move.”

She’s in the room with me.

i stay as still as I can.

i hear her draw on a cigarette- and then the smoke hits me in the centre of the ring gag.

i cough, and she laughs.

“you are pathetic aren’t you tiffany?  Look at your tiny cock.  I’ve had to buy a CB6000s for you.  The “s” stands for short.  You tiny cocked wanker.”

She blows smoke into my mouth again, and I tremble.

i hear her stand up, and walk round me.

“Don’t fidget tiffy, or I’ll keep you like this all night.  Wanker.

“Do you think it will improve when I let you stand up?  Because it won’t. As long as you are here with me you will be receiving no comfort, just humiliation and discomfort.  Because you are nothing but a cross-dressing sissy with a tiny cock.”

The butt plug makes my arse feel raw.

Drool is pouring from my mouth because of the ring gag.

My knees hurt, my back aches.

But it doesn’t let up.

She blows smoke in my mouth, whispers insults in my ear.

And I realise that the next 24 hours are going to be a constant torment.

It goes on, apparently for ever…..

“Stand up tiffy.”  I struggle up, and she removes my mask.

“Time for dinner,” she grins……

A Quiet Weekend At my Flat

I went to my flat this weekend. I had some business to do in Hull, so staying in Gainsborough was a good option. And of course it gave me the opportunity to unleash tiffani…
I arrived late, and tired; the traffic was just awful. I parked up in the car park under the flats, and taking my bags, I got the lift up to the 4th floor. I walked up to the door, and put the key in the lock……. but it wouldn’t turn. I checked it was the right key, and tried again- nothing. But when I tried the handle, it turned….. Hell, I must have left the door unlocked the last time I was here.
I went in; the lights were on. Something was wrong here. I dropped my bags and walked up to the living room, opened the door and went in.
To my shock, there was somebody sitting on my sofa- an imposing looking, attractive blonde woman, wearing a black skirt and top, smoking, legs crossed, a glass of wine on the coffee table in front of her.
“What on Earth….” I started, but she raised a hand and cut over what I was saying.
“Don’t panic Rob, your wife Anne sent me. She’s asked me to do something for her.”
“What? How do you know Anne? What has she asked you to do?” I frowned, confused.
“It’s simple Rob, here read this.”
She handed me a note- clearly it was from my wife, I’d know her terrible handwriting anywhere.
“My name is Eleanor by the way, but you can call me Mistress.” The lady on the sofa said. And then she kept talking as I read the note. “She found your suitcase Rob, and she’s not impressed. If you don’t do what I tell you to, she’ll expose you to your friends and colleagues, and she’ll divorce you and take your money and business.” The note confirmed it. “And by the way, you are to be known as tiffani from now on… tiffi.”
“But, but, Oh God, how…..what….” my mind whirled and I sat down.
“Stand up tiffani, you haven’t earned the right to sit on a chair. Let me put it simply. Your wife is unhappy with you, and has hired me to turn you into her feminised sex slave and domestic help. And I have a free hand to do whatever I want to you.” ..... continued 
Posted by sissy tiffy