Elizabeths Adventure

The package arrived via Fed-Ex Friday morning. Elizabeth had been expecting it, but even so, when the Fed-Ex delivery man dropped the envelope on her desk she jumped.

“Sign here please Ma’am.” said the young man.

Elizabeth signed for the package and, with a look over her shoulder to make sure that no-one was looking, she opened it. Inside were several things; a letter, a key, a sealed envelope and an airline ticket. ‘Hmmm’, thought Liz, ‘This time’s he’s outdone himself.’ The ‘he’ she was referring to was Tom, Liz’s boyfriend. In the 6 months they had been seeing each other, Liz had discovered more about excitement and her own sexuality than in the 25 years previously. Tom was always coming up with the next “adventure” for them to take on together. It had been Tom who had introduced Liz to Bondage and to the kind of games that Mom never told you about.

Elizabeth was now a successful software broker and had opened up her own business selling software to large companies that needed to buy in bulk. At the office Liz was always in control and very much her own woman. To her surprise, Liz had found out that she loved being the one who was tied up, that she loved being submissive. She was always excited when Tom had ‘instructions’ for her. Last week, Tom had promised her an adventure of “unparalleled proportions” and to expect her instructions on Friday via messenger.

Liz opened the letter to find out what she needed to do next. The letter was a short one and contained her weekend instructions.

Dearest Slave Liz,
You’ll find enclosed all that you need to begin your “adventure”. The airline ticket is to Chicago and the plane leaves at exactly 6:00pm. Don’t miss it. The flight will take a little under 2 1/2 hours. The return flight, as you can see, will have you back at work on Monday morning. For your flight, you are to wear a pretty cocktail dress. It must have a hemline above your knees and I expect the fabric to be light enough that I could see through it if the light were behind you.

When you get on the plane, you are to open the sealed envelope and follow the instructions inside. Do NOT open the envelope beforehand.

You’ll also find a key in the package I just sent you. This key is for use in Chicago. Bring it with you.

I love you lots and you can expect this ‘adventure’ to be the best yet.

Love, Tom.

Liz’s face was flushed and her breathing had quickened by the time she finished reading the instructions. She would have to get moving if she wanted time to go home and change before her flight. She couldn’t believe that she was going to get on a flight to a strange city for a sexual escapade.

By 6:00pm, Liz had managed to pull it all together. She had left the office a few minutes early and had rushed home to have a quick shower and change. The only dress she had that fit the instructions was a light yellow sundress that was strapless. It was a little out of fashion for November in Chicago, so Liz put a white sweater over it. A bra was, obviously out of the question but Liz made up for it was a garter belt and stockings and a pair of sheer lace panties. She threw some other clothes into a carry-on bag and rushed to the airport where she just made her flight. The plane left right on time and as soon as they had levelled off, Liz reached into her bag for the sealed letter. There was, thankfully, no one sitting next to her because Liz was sure that the letter would be very explicit and she would die of mortification if a stranger read it.

Inside the envelope, as expected, was a letter:

Dearest Slave Liz,
If you have followed your instructions, you are now winging your way to Chicago where your weekend adventure will continue. Here are your instructions:

First, as soon as you finish reading this, go to the plane’s washroom. Once in there, remove your bra, panties and stockings. Do not masturbate. You are not allowed to masturbate until I tell you. Once you’ve taken off your underwear, leave it in the garbage disposal in the washroom You won’t be needing them.

Next, go back to your seat. When you sit down, lift your dress so that you are sitting directly on the fabric of the seat. During the rest of the flight, write a fantasy of exactly what you’d want to happen to you in our next adventure. Make sure it is the most exciting thing you’ve ever thought of.

When you get to Chicago, walk across from the terminal into the O’Hare Hilton. It is only a couple of minutes walk. The key I gave you is for room 310. Go directly to that room. Once there, remove the rest of your clothes and hang them up neatly. You’ll find a blindfold on the bed. Put it on and then lie down on the bed, face down and spread your legs wide apart. Stay like that until you get further instructions.

Your Loving Master,

Liz was squirming by the time she finished reading the instructions. She was sure that there was a wet spot on her dress when she got up to go to the washroom. She had to wait a moment before getting in.

Inside the tiny airplane washroom, Liz had trouble trying to get undressed. Finally, she managed to get her panties and stockings off and stuffed them into the disposal chute. Liz took a long look at herself in the mirror. She knew that she was a very pretty 25 year-old. Her sandy blond hair was short and curly. Her figure was not voluptuous but she liked it. She was more like a runner, she thought. Her breasts were 35 B’s and her tiny waist and trim hips showed the hours of exercise and dancing that she did on a regular basis. She took a long deep breath and left the washroom.

As she moved up the aisle back to her seat, she felt very exposed. She knew that the men in their seats were looking at her and she felt like they could see right through her light cotton dress. She felt a blush hit her face as she finally sat down. She was about to do up her seat-belt when she remember the instruction about how to sit. Liz looked around her to make sure that no one could see.

Everyone seemed preoccupied with whatever they were doing. As surreptitiously as possible, Liz pulled the back of her skirt up so that her now bare bottom was sitting directly on the seat. Finally, she was organized and as she looked up, she saw one of the stewardesses was looking right at her. Liz blushed a deep red as the stewardess gave her a knowing smile. Liz dropped her eyes and buckled up her seat-belt. She felt the heat of her embarrassment all over her face and knew she must look like a little girl with her hand in the cookie jar.

The plane was soon descending into the crowded skies around Chicago’s O’Hare airport. Liz was getting more and more excited. She read her instructions again and again wondering what would happen to her once she was naked and blindfolded, lying on the bed face down. She kept herself busy writing down the fantasy that Tom had asked her for. She wrote a sizzling fantasy about being on a tropical island and being captured by natives who stripped her and subjected her to countless sexual trials. She was soaking wet by the time the plane landed and she knew that she would leave a wet spot on the seat when she got up.

As soon as the airplane door opened, Liz scooted out of her seat and out of the plane, making sure her skirt was pulled down as she got up. The stewardess who had seen her pulling up her skirt was at the door and she smiled as Liz came forward.

“Have a nice day Miss.” said the pretty flight attendant and Liz blushed again as she thanked her.

Once out of the plane and into the terminal, Liz found herself following the mass of people as they headed for the exit. She asked someone at the Car Rental counter where the O’Hare was and was told it was right across the street. Five minutes later, Liz walked into the lobby of the hotel. The elevators had her on the floor a moment later and then she was at the door of room 310. She put her key in the door and then, just as she was turning it, had a thought that maybe she wouldn’t be alone! The thought had her pause but it was too late now. With a deep breath, Liz pushed the door open and walked in.

Thankfully, the room was empty. The curtains were flung wide open and Liz wondered if people could see in. Certainly she could see out very clearly and the idea of taking off her clothes in such an open environment made her shudder. She wondered if she was allowed to close the curtains. She figured not. After all, the rest of the instructions had been so specific, she was sure that Tom wouldn’t have forgotten something like the curtains. Liz looked around the room and couldn’t find anything in the closet or anything else that said that Tom was here. In the middle of the bed, however, was a black silk blindfold.

Liz took one of the closet coat hangers and went to the bathroom that was positioned right across from the closet. In the bathroom, hidden from what seemed to be the eyes of all of Chicago, she slipped out of her dress and heels. Her dress went onto the hanger and her shoes she held in one hand. She looked out for a moment from the bathroom then jumped across to the closet and put her things away. She jumped right back to the bathroom and took a good look at herself in the mirror. Her pussy was soaked, she noticed.

Last month, during one of their ‘adventures’, Tom had shaved off all of Liz’s pubic hair and he insisted that she keep it smooth “just like a good slave.” When she looked at her now puffy pussy lips, they were covered with her juices. Liz wet a hand towel and cleaned herself. In a couple of minutes she was ready. She knew all this primping was just putting off the inevitable.

Taking a deep breath, she left the bathroom and scooted onto the large bed in the middle of the room. The blindfold was still there and Liz quickly pulled it on, making sure it covered her eyes completely. Then, as instructed, she lay face down and spread her legs wide apart. Lying there, not able to see, Liz started to imagine all kinds of wild things. She imagined that there were people peering into the room from the window and that she was on display just like in a zoo. She imagined that there was a video camera hidden in the corner of the room, watching everything. She imagined the stewardess from the plane coming into the room and teasing her and toying with her just like Tom did.

The thoughts didn’t stop and the longer she lay there, the more excited she got. When she finally heard the key in the door, she was very turned on. ‘Would it be Tom?’, she wondered. He had never involved anyone else in their sex games before but he had threatened to from the first time he had tied her up. The idea of being helpless to prevent someone from seeing her naked and exposed turned her on.

The door opened and Liz heard someone walk into the room. She held her breath, trying to hear everything as though the sound of the footsteps would tell her that it was her lover or not. The door closed and the footsteps started walking around the room. Liz heard the sound of a bag being put down on the table then the zipper as it was opened. The footsteps carried on all around the bed, looking at her from every angle. The unmistakable click of a camera had Liz blush as pictures were taken of her in this exposing position. Finally the camera was put down and Liz heard Tom’s voice for the first time.

“Hi there my little slave, how are you enjoying your adventure so far?”

Liz sighed with relief, “Oh God!, I had no idea if it was you or if you had found someone who would take pictures of me. “

Tom laughed, “Don’t talk too soon. I’m going to prepare you now for an ‘examination’.”

Liz felt Tom’s hands on her wrists as she tried to digest what he had just said. An examination?, she wondered, by who? and what would they do? Her mind was a jumble as Tom attached wrist straps to her and then pulled her hands wide apart to attach to the corners of the bed. Tom lifted her hips and pushed several doubled up pillows under her belly and then had Liz pull her knees wide apart and forward so that she was straddled on the pillows. More leather straps around her thighs and ankles made sure she would be staying in position. The effect of the pose was not lost on Elizabeth who knew that both her bare pussy lips and her anus were now fully spread and exposed. Her breasts hung below her so that just her nipples were touching the bed. The tingling touch of the bedspread on the sensitive nipples added to Liz’s excitement. Finally she was ready.

Tom patted her on her perfectly curved bottom, “Alright Liz, you’re ready for your examination. Just relax. I’ll be leaving the room now, but the next person to walk in will be examining your body and your submissiveness thoroughly. Enjoy yourself.”

Tom chuckled as Liz heard him leave the room. Her mind was now running rampant as she imagined what might happen next. The position she was in was not only completely exposing and humiliating, she was also helpless to get out of it. She really had no choice but to submit to whatever would be done to her next. Each minute seemed like an hour to Liz but finally she heard the key in the door again.

She was breathing heavily as the door opened and someone walked in. Was it a man or a woman Liz wondered. Would they be gentle with her? The door closed and Liz heard the footsteps walking all around her. Her 25 year old body pulled at the straps holding her wrists in a vain effort to let herself free. She kept waiting for them to touch her, hoping they wouldn’t and also hoping they would. The first touch of the cool fingers came at her left breast. Just the tips of the fingers as they gently grasped her nipple and tugged it away from her breast.

Liz gasped.

The touch had been electric. She felt her nipples stiffen and grow even longer into the fingers of the stranger. The long cool fingers rolled the nipple back and forth, teasing it and playing with it until Liz couldn’t stand it any more and moaned out loud. The fingers left her nipple and just the tips of them trailed down along her ribcage, tickling her and making her squirm at the sensation. It was as though every nerve ending in Liz’s body had awakened and was ready to be teased. The fingers reached Elizabeth’s bottom and moved further along the side of one buttock and down the outside of her thigh. At the back of her bent knee, the fingers stroked her gently before moving to her inside thigh and starting to trail upwards.

Liz was holding her breath again waiting for the hand to reach her soaking box. She felt a trickle of her own juices slide down her leg and blushed at having so revealed herself to the stranger. The maddening fingers had reached Elizabeth’s pussy and she felt them stroke the outside of her smooth pussy lips.

Her pussy responded to the teasing by puffing out even further and opening the hot pink interior lips to the ‘examiner’. Just the tip of one finger touched the wetness inside and Liz gasped as it moved around slightly. She felt herself pushing her bottom down trying to get the fingers to touch her hard and sensitive clit but they didn’t oblige.

A fraction of an inch at a time, the finger pushed itself into Elizabeth, lubricating itself on her juices. Liz let out a long sigh as the finger penetrated deep inside her. The finger turned slowly then pulled out, again a fraction of an inch at a time. Liz felt the hot wet tip of the finger travelling up her crack and pause at her tiny crinkled opening.

“Oh, no.” She pleaded. “Not there.”

The stranger paid no head to the bound woman and slowly pushed the lubricated finger deep into her bottom. Liz squirmed helplessly in her bonds. There was nothing she could do to stop this stranger from violating even her most private opening. The finger slid out and then pushed in again even deeper. Liz moaned at the feeling. Back and forth, the penetrating finger turned and touched until Liz was panting at the sensations running through her body. Finally it pulled out.

Liz was left, gasping as the stranger moved from behind her to another part of the room before returning. Again Liz felt a touch at her anus. This time, the touch was cool. Liz felt the cool touch of a plastic plug as it was pressed into her. Her bottom tried to keep out the intruder but without success.

Elizabeth’s toes curled as the thick bulge in the middle of the plug passed inside her and her muscles pulled the rest of the plug deep into her body. The ‘T’ shaped handle kept the plug from disappearing into her completely and the result was that her tiny virginal anus was kept open, clenching down on the neck of the white plastic plug.

Liz’s breath was in short ragged breaths now. She was sure she would come any minute. The stranger stepped back. Liz heard the whistle of the leather strap through the air a split second before it exploded on her bottom. She cried out more in surprise than pain as the strap came down again and then again. She was helpless to do anything but endure as her spanking continued. She had been spanked by Tom before but this was the first time a strap had been used on her tight bottom.

The strapping left Liz’s bottom hot and red. The pain only lasted a couple of minutes but the heat remained. It seemed to travel through her body, making her nipples even more hard and her pussy even more wet. With each stroke, Liz felt her ass clench down hard on the unyielding plug still inside her. The sensation seemed to go directly from her ass to her clitoris. By the time the spanking finished, Liz was trembling. She had never been so excited in her life.

The stranger moved aside again and a moment later Liz felt a sensation she would remember for the rest of her life. The plug in her bottom suddenly came alive! The plug started to vibrate deep in her bottom and Liz felt the beginnings of an incredible orgasm. The door suddenly opened and Liz heard as if from a distance, the strange person leaving the room. The orgasm hit her like a ton of bricks. She cried out again and again as waves of pleasure washed over her. Her anus clamped down hard on her rectal plug and the sensation caused her to cry out again as another wave of orgasm took over.

Liz thrashed back and forth, pulling frantically at the leather straps that bound her. She was sure that if the pleasure didn’t stop right now, she would die from it, but still it continued. She was helpless to stop it. When she was sure she couldn’t come any more another orgasm hit her just as hard as the first and again she cried out. Finally, exhausted, she lay still, the rectal plug still causing her to spasm from time to time as it hummed in her bottom. The vibrations stopped quite suddenly and Liz felt her whole body relax. Fingers tugged at the silk blindfold covering her eyes and a moment later daylight poured in to reveal Tom sitting beside her. Very gently he untied her from the bed and helped her to lie down. As if in a dream, Elizabeth looked up into his eyes and smiled.

“It was the best adventure ever”, she said drowsily, “but I’d like to sleep now.”

“Yes, have a good sleep,” said Tom, “because today’s is only Friday and we have the whole weekend together. Wait until you see tomorrow’s adventure.”

Updated: June 17, 2020 — 2:20 am