The following is written in UK English, if you don't enjoy my style please pass me by, it's how I was dragged up and even on Lit. I have to live with that.
*
I'd requested my current lover, Harry, to take me out of my comfort zone: we've swapped before, tried a little bondage but I had not expected his response. When I arrived home Friday evening his handwritten note simply said, "Undress, shower, shave your pussy bare and dress in your red shoes, black stockings, blue suspenders, green skirt, yellow jacket and nothing else. Apply red lipstick, green eye shadow, lots of non-water proof mascara and green nail varnish. Get your orange handbag, put your keys and a packet of tissues into it and nothing else. Arrive at the station at six fifty and go to platform four. There a man will identify himself and give you further instructions. Jesus. were the fashion police in for a fun time but I'd be easy to spot.
The platform was deserted so I had to wait, typical Harry. He was a bit of a drama queen and loved to build a little tension. He was certainly succeeding I was almost shaking. Eventually, a train pulled up and a number of commuters descended from the carriages. One of them walked over to me and said, "I'm Jim. I'm your guide. In order to confirm my identity you must unbutton your jacket for me and I should be able to see your bare breasts."
"Bloody Hell," I squealed, "what right here with the security cameras and all?"
"Please just follow the instructions, I'm not allowed to discuss them.
I turned my back on the nearest camera and unbuttoned my jacket to show Jim my firm yet ample bust.
He gazed for a few seconds and then said, "thank you ma'am. You may button up. Now hold still whilst I feel under your skirt. If I am the right person I will find that your pussy is smooth and hairless." He slipped a hand under my skirt, stroked my naked mons making me shiver with anticipation and then he ran a finger along my embarrassingly wet slot, which made me blush hot crimson.
"Thank you ma'am, sorry if I embarrassed you but those were my orders. We are to catch the next train. You will sit by the window and I will sit opposite to you and deliver your next set of instructions." The train was by no means empty but neither was it busy so we had little difficulty in locating two empty opposing window seats.
"You will come with me and I will take you to where you are to spend your weekend. I will collect you at eight p.m. on Sunday and escort you home. Once safely home you are to reward me by stripping naked and lying face down over your pink pouff. I will then take my pleasure in which ever hole I fancy. One piece of advice I can offer you is to keep your arse well greased, here's a small pot of Vaseline to add to the contents of your handbag. You may make a trip to the loo if you wish."
"But... But I've never. No one's... I mean."
"You've not been fucked in the arse. Well long before I get you home that will have been remedied, in all probability many times over."
I stumbled to the tiny toilet. I was close to tears. I knew that I had requested 'out of my comfort zone,' but this was going to be into my worst nightmares. I rubbed my tight little sphincter with the gooey stuff then slipped a tentative greasy finger inside of me; just to feel what it might be like. It was not as bad as I had expected. In fact it was not really at all unpleasant. As long as I was not stretched too wide it might be alright. I washed my hands thoroughly and returned to my seat good and slippery.
So Jim was to screw me or have me suck him off. I decided that I would not mind that in the least. He was young, mid twenties I guessed, probably just a little younger than I. He was slender, muscular and rather dashing. His speech was curious, southern continents, northern vowels; it was fluid and eloquent, no 'um's, er's, nor like's and when reporting dialogue people said rather than 'going.' He was wearing an old fashioned grey suit over a white shirt and narrow red tie; I wondered if the suit had once belonged to his father. His black brogues were highly polished, indeed his whole demeanour was highly polished; he might have been an actor.
"Have you ever had another woman make you come?" he enquired. "By the way one of the rules is that you must always tell the complete truth at all times without prevarication, omission or exaggeration. If you are caught in a lie you will be spanked on the bare bottom, the first time with a wooden kitchen spoon. I have it here, please place it in your handbag and also hand me your keys, I will return them after I have taken my reward from you."
I was nervous about handing my keys over, especially since Jim clearly knew where I lived. Jim smiled and waved a copy of my own front door key in front of me. Harry obviously trusted him so, with some trepidation, I handed my keys over. Now I had hardly any clothes on, no phone, no money and no way of returning home. I was scared but also curiously excited, my pussy was moist and my nipples like bullets. I just wished the latter would not rub so against the rough fabric of my jacket.
"Anyway, have you ever had another woman make you come?" reminding me of his question.
"Not strictly I replied but when I was a girl the girl across the backs from me, Alice, and I used to finger one another to a lovely warm climax. If Mum and Dad were out we'd lick each others titties too. Sometimes she'd pause and make me writhe on the end of her finger till I promised to lick her to orgasm."
"So your not a complete stranger to lesbian attentions and have enjoyed them previously."
"Yes," I mumbled. I was blushing again. The thought that women as well as men might be about to take advantage of me was a strange but wonderful prospect. That would be, well not a first, but a delightful reintroduction to the pleasures to be had from members of my own sex.
"Show me your tits again, right now!"
I unbuttoned my jacket and held the sides so that they shielded my not inconsiderable assets from prying eyes.
"You may button up once more. Now hitch your skirt until your suspenders and stocking tops just show."
Jim had sharp hearing because as I adjusted my hem the conductor entered the carriage. I doubt he even looked at our tickets as he clipped them, his eyes were riveted upon my hemline. Finally he smiled at Jim, returned the tickets and said, "Thank you very much sir," in that nudge, nudge, wink, wink tone that leering men can do so well." That made me blush, yet again. True to my request, I was well outside of my comfort zone and the evening proper had not even begun.
When the conductor had gone Jim instructed me to "eat these" as he handed me a packet of sandwiches and a large bag of crisps. Lettuce dressed with mayonnaise, cucumber, tomato and strong Cheddar cheese cut thick. Harry had done his job alright, my favourite. I had not had time to eat and I wolfed them down, all four of the thick sandwiches. I offered to share the bag of crisps with Jim but he declined, politely. "Once I've delivered you there's an excellent fish and chip shop not far away, in the back they have a couple of tables and I must not spoil my appetite; the bread and butter's complementary you know." I didn't but he made me feel as if he had let me in on a dark and deadly secret. Given his physique, perhaps it was a dark and deadly secret, Jim's little weakness, maybe. He was certainly bold enough in telling me about what he was to do to me!
Gradually more and more men developed weak bladders and kept having to walk past us to get to the toilet. That train must have had only that one toilet working. I never knew that a stocking top, a blue suspender clip and half inch of bare thigh could garner quite so much attention but when on public display they obviously do. I was embarrassed by all the attention but proud too, however, I must admit that in the end I was glad to get off that train. We alighted at a tiny station in a small town that I had never visited before. We exited through a back entrance into narrow terraced streets.
The area was a maze of near identical dwellings and as they had back streets as well as front ones Jim soon had me completely lost. We entered one of the numerous red brick houses through a back gate and Jim led me to a small outbuilding. He held open the door for me. "I'm to leave you here. You must undress completely, place your clothes and, once you have taken the wooden spoon out of it, your handbag in the wooden chest in the corner and then snap the padlock shut. Hold the wooden spoon in your right hand and await further instructions.
So, at around eight o'clock I'm stood stark naked in a shed, in a strange house, in a strange town with no phone, no money and no access to my clothes. To make matters worse rather than being delivered by a person my instruction came through a loud speaker. "Teresa welcome to they house of surprises. You are every bit as attractive as Harry promised us. I'm glad you've shed that preposterous costume. Your nipples are very stiff, I hope you are not cold. Still it's a very warm evening. Oh if you need to pee there's a bucket in the corner and we even left you a little toilet roll; personally, I'm not sure about such indulgent luxuries, a wet rag ought to suffice, but the others insisted.
'What,' I thought, 'I've to piss into a bucket. Not bloody likely.'