This is a story that came to mind when I was asked by somebody what was the one thing I should have done that I did not, it happened to me a long time ago. I will leave it up to you to decide when reality stops and fantasy takes over. PS this was before the days of the internet and its UK based story so fanny is not ass its pussy.
The flight over to the Isle of Man had been very quiet and there were plenty of taxis outside of the airport. The weather was typical of an English winter; it was freezing cold and the rain was hammering down. I got soaked just running from the airport terminal to the taxi rank.
It was my first business trip to the island and it was all very new to me. The village I was working in was at the far side of the island and did not even have a hotel, so I had booked into a local Bed and Breakfast. The journey took half an hour and I was soon standing on the porch of the Bed and Breakfast, ringing the bell whilst shaking off as much of the rain as I could.
The door was opened by the owner, and as she ushered me in, I noted she was a little shorter than I was, slightly older and blonde. She was gorgeous, dressed in a white blouse that showed a black bra through it, a bra that was cupping a gorgeous set of boobs. Further down she had on a black skirt with black nylon stockings and was wearing a pair of black high heels. I thought she looked sexy as hell, and on that cold wet night, she was a real site for sore eyes.
"Hello there, I am Debbie", she said with a smile. "Welcome to my home."
"Zak, thanks for having me", I replied.
"Nice to meet you Zak", she said. "We don't get many visitors in the Winter, so you have the place to yourself!"
And with that she showed me the layout of the place, where breakfast would be served etc. Then she took me up to my room, it was up two flights of stairs and I took position behind her so that I could gaze at her amazing little bottom. She was wiggling her arse as she went in front of me and the site was one to behold.
The bedroom I was given was small but it was well laid out if a little homely, with a small shower space and toilet in the en-suite bathroom. Debbie left me to it with the request that if I needed anything just ask.
I hung up my work clothes and unpacked my toiletries before stripping off and having a nice shower. The water was hot and took the chill from my bones. I dried off and slipped on my usual night ware, a pair of bed shorts and t-shirt, before grabbing a magazine from my case and lying on the bed. The magazine was soft porn; a few stories with pictures, readers letters, that sort of thing. I had picked it up and the airport, slipping in inside a copy of the Telegraph as I paid for it.
I started to flick thought the pages until I found a story I liked. I slipped my hand down my shorts and started to give the 'old crown jewels' a stroke, as most men would have. It soon became evident that the elastic band on the shorts was very tight, so I slipped them down over my knees to give me more room. I was busy reading a nice little story when Debbie walked in. There was little I could do, I had been caught red handed.
She knew what I was doing, I knew she knew what I was doing and she knew I knew; there was no escaping from it, I was caught bang to rights.
Time stood still as Debbie stood watching, my hand around my slowly wilting cock and I was holding my breath. I was sure she would scream the house down, kick me out or something.
I looked at her, and she looked at me, and I was sure I was about to have a heart attack.
She placed the tea she was holding on the bedside table. I was waiting for the world to erupt but as she just sat down on the side of the bed, my heart skipped a beat.
"It's okay Zak, it's only natural, please don't stop on my account", she said, almost purring as she looked at my now soft cock.
I was like a statue, my hands feeling like lead, I couldn't move them. There was no way I could continue.
"Wow, nice cock!" she said, as she leaned over and took my hands off my cock. She used one digit to touch the swollen head gently and I trembled with trepidation.
Her tiny hand, with red polished fingernails, slid under my ball sack and stroked it gently, making me gasp out loud. Then her fingers stroked up over my cock, one of her thumbs rubbed over my glans before she encircled it and slowly stroked it. It was like a jolt of electric though my body, her touch was feather light but at the same time it was sending pulses of intense pleasure thought my body.
Her fingers traced patterns over my dick, as she stroked up its length and back down over my tightening ball bag. My cock jerked at her every feather-like touch. She cupped my balls in one hand and gently weighed them.
"Oh they certainly need emptying", she giggled.
I saw that a little pearl of pre-cum had escaped from my cock. Debbie wrapped her fingers around the top of my cock and used her thumb to rub the cum over my mushroom-shaped cock's head.
Making a circle out of her thumb and index finger, she squeezed the sensitive skin just below the bell end, this made more juice slip out of my cock's slit. She began to revolve her fingers slowly, first one direction and then the other, using my cum as a lubricant.
I watched unable to move as she slowly and methodically masturbated me. I wanted to talk, wanted to say something, but the words were stuck on my throat. She shifted position so that she could use one hand to fondle my balls and one to stroke my organ.
She had a look of total concentration on her face as she went about her work. Every now and then she let out a little 'ohhh' or a little 'ahhhhh'.
I looked down and noticed that her skirt had ridden up, and I could see her sexy legs encased in those black nylon stockings, I could even see the black suspender's holding them up. My heart again skipped a beat as a pair of black G-string panties came into view. I tried not to look, tried to be the gentleman, but those sheer black stockings on those lovely legs was just too nice a view to miss.
I tried to block out the immense feeling of pleasure that was coursing through my body. I tried to think of anything but the amazing sensation that her ministrations were giving me. It was hard; trust me, no pun intended, as hard as hell.
I looked up at Debbie. She was staring intently at my throbbing cock with her left hand still fondling my balls, sometimes cupping them, sometimes trailing her nails over the tight skin. Her right hand was slowly stroking up and down my length. She gently pulled my foreskin down exposing my cock's mushroom-shaped head; that made me groan out loud.
I watched her wrap her hand tightly around my shaft. I felt a chill run down my spine as Debbie stroked my erection, sliding her soft hand from base to tip, milking more juice from the head. Suddenly, her head began to move closer to my cock until I could feel her breath on the throbbing head.
I slipped one hand onto her leg, feeling up along her thigh, until I was touching the bare flesh just about the elasticated top of her nylons.
Debbie looked at me and smiled as she continued to stroke me; long slow strokes, deliberate and firm. My head was spinning and my breathing was deep. She seemed to know when to increase the pressure and speed to bring me close and when to slow down and release the pressure before I boiled over.
She seemed to be enjoying wanking me as much as I was enjoying her wanking me.
"Are you getting close?" Debbie whispered breathlessly. I could only grunt my confirmation and that made her giggle.
I watched her hand sliding up and down my cock, and I knew I would not last much longer. Her red fingernails entranced me; her face was now so close to cock I could feel her breath on my exposed bell end.
I heard a growl and realised it had emanated from my throat. Debbie started to stroke slower but with more pressure and more intensity. I felt my balls tighten as my orgasm started to boil up inside me. I was desperate to hold back but the feeling of one of Debbie's hands on my nuts and the other on my cock was too much and with a sigh I let my natural urges take over. There was no point trying to hold back as I knew that my body was going to ignore my brain.
.... There is more of this story ...