It had been raining most of the day but now that the temperature was dropping the rain turned to snow and the water already on the ground turned to ice. It was a messy slippery day. I needed to pick up a few groceries so I stopped at the local store on the way home from work. The car ahead of me was moving very cautiously but I knew I had to be patient in this weather. It pulled into a parking spot and then continued into the spot ahead of that one. I pulled up behind it.
When the door opened out stepped a pair of tight knee-high boots with very high heels. They were followed by a woman in a black leather coat. Long curly red hair tumbled over her shoulders. From behind she was gorgeous and I wanted to get a look from the front. I got out of my car in time to see her slip and almost fall into the slush. She grabbed the fender of her car and was hanging on to stay up.
I rushed to her to help out. I said ‘Let me give you a hand’ and then I took her by the arm and steadied her. She turned to thank me. She was very good looking. She was also, by my best guess, in her late sixties. The fact that she had the figure of a younger woman got my attention and I’ve always been a sucker for red hair but I certainly didn’t expect what I saw from the front.
‘I shouldn’t have worn these boots in this weather’ she said ‘it was very stupid of me.’ I told her ‘Don’t be so hard on yourself; sometimes there’s a price to be paid when you want to look good.’ I helped her get into the store safely, got a shopping cart for her, she thanked me and then we parted ways.
As I went up and down the aisles looking for the things on my list I crossed paths with her several times. She looked better every time we met. Around her neck was a white silk scarf which went perfectly with her blazing red hair. Her coat was open to reveal a shiny white blouse with small black buttons up the front. A brown suede skirt and matching brown stockings completed her outfit. Her clothing looked expensive and she looked classy.
On the way out we reached the check-out at the same time. My cashier was much slower than hers and I was still in line when she left. I watched as she left and thought to myself “I wish I had met her forty years ago, she must have been some beauty.”
On the way out she was standing beside the door. She looked at me with a pair of emerald green eyes and asked ‘would you be a dear and walk me back out again please?’ I told her I would be happy to and took her by the arm again. I placed her bag in the back seat and began to help her into the front. As she was getting in she paused for a moment and said ‘Thank you very much, you’ve been such a sweetheart I wish there was something I could do to repay you for your kindness.’ I was about to tell her that wasn’t necessary when she excitedly blurted out ‘I know what I can do. How would you like a blow job?’
To say I was stunned was an understatement. This classy old lady had offered me thanks in a way that no one would ever expect to be thanked. Before I could regain enough composure to reply she continued ‘My dear departed husband always said that I gave the best blow jobs in the world. He’s been gone three years now and I’m getting out of practice. What do you say young man; will you let me do this for you? I think it will do us both some good.’
I may have been flustered but I wasn’t stupid. In a stuttering voice I accepted her offer. I got into my vehicle and followed her home. All the way there I was wondering just how grateful she was. Every time I saw her in the store I had tried to imagine what she would look like tied up. Now I was picturing her giving me blow job while tied up. I got such an erection it was getting difficult to concentrate on driving.
By the time we reached her home I still had no idea how to approach the subject. I carried her groceries with one arm and escorted her with the other. Once inside we removed our coats. When I got a better look at her my opinion didn’t change; if anything it improved. She had a slender figure and a lovely pair of breasts. She pulled off her scarf to reveal a long elegant neck and a slim gold chain that disappeared down into her cleavage. The combination of the green eyes and the red hair was further enhanced by a slight hint of freckles across her cheekbones and a bright red lipstick on her full mouth.
Still without a plan I decided to just be honest and ask her. ‘I hate to take advantage of your generosity but I am wondering if you would be open to a request? Ever since I was a young boy I have had a fascination for damsels in distress. As I got older my fantasies had a tendency towards taking advantage of these damsels. Being an intelligent woman I am sure that you know where this is going.’
‘Well sonny’ she replied ‘for my generation a damsel in distress was a woman being tied to the railroad tracks by a villain dressed in black. I would imagine that it doesn’t mean the same thing anymore. Why don’t you get me up to speed on what it takes to be a modern damsel?’
I was a little uncomfortable opening up my desires to her but she was so open to new ideas that it got easier as I explained what my hopes were. I didn’t want this to be an impersonal encounter; I wanted there to be some interaction between us. I told her that it would be nice to do some role playing.
She said ‘That’s a wonderful idea. I used to do some amateur theater. That’s how I met my husband; we were in a play together.’ From the look on her face I could tell that she was lost in her memories. I gave her a minute and then brought here back to now. I started to explain what I wanted to do and she very enthusiastically made a few suggestions, most of them good ones. In just a few minutes we had created a scenario to act out.
I was going to be a thief who gained entry to people’s homes by posing as an inspector who was looking for a gas leak. She would be the unsuspecting senior (her idea not mine) who was foolish enough to let him in. We had a general outline but we deliberately avoided too many specific details. She said that the best theater is created when the players react to the situation as it unfolds. She had become the director of our little production and I didn’t mind at all. If she could bring the same excitement to her performance I knew it would be a success.
I went out to get a pair of coveralls from my trunk so that I looked the part. I was also going to grab my tool box which had a very special set of tools in it. No screwdrivers; no wrenches; just rope and tape and other things essential to my hobby. As I was going out the door she asked ‘Is there anything I can do? Would you like me to put on a negligee or answer the door with just a towel on?’ I realized that a woman doesn’t get to her age without figuring out what is sexy and how to turn on a man.
She had taken off her wet boots when we came in so I told her ‘You look great just the way you are but if it’s not too much trouble could you please put on your sexiest pair of shoes.’ I went out to my car in just a few minutes I was back knocking on the door. A second of panic crossed my mind. What if she had played along just to get me out of the house? Getting the tools was her idea. What is she was just trying to get this sex maniac out so that she could lock the door and call the cops?
I knocked. She said ‘who’s there?’ ‘It’s the gas company ma’am. There’s a leak in the neighborhood and we just want to check your house to make sure that it’s safe.’ She opened the door and I stepped in. As she closed it again I stepped up behind her and clamped my left hand over her mouth. Using my other hand I pushed her against the door and I said to her ‘Don’t make a sound. Cooperate and everything will be alright. Do you understand?’ She nodded yes.
Holding her against the door I took my hand from her mouth and opened my tool box and took out a piece of rope. I tied her hands behind her back. I began to reach for a gag when I noticed her scarf hanging on a hook at the entrance. I took it down, knotted it in the middle and gagged her. Then I turned her around and told her ‘Now you’re going to show me where you keep your jewelry.’
She led me to her bedroom and motioned with her head towards the dresser. A jewelry box sat on top. ‘I’m going to be taking that with me’ I said ‘but first I’m going to make sure that you can’t get help any time soon. I wouldn’t want to lose my head start on the police.’ I sat her on the chair at her make-up table and tied her ankles. It was then I noticed the shoes she had picked. They were a pair of brown suede pumps that matched her skirt. I was about to tie her to the chair when she began to mmph through the gag. I pretended to ignore her and she got more insistent. I undid the gag.
‘Please don’t take the jewelry’ she begged ‘I have a lot of pieces of sentimental value from my mother and grandmother. Please take something else.’ I grabbed her by the hair, bent her head back and in my most menacing voice I told her ‘You are in no position to negotiate; I’ll take whatever I want. And besides what else do you have that I would want. Appliances are too much trouble to haul out of here and your car is too big to hide so just what else do you have to offer?’
She was quite an actress. She looked up at me with what appeared to be genuine fear and in a trembling voice she made me an offer. ‘There’s not much I can do tied up like this except to offer you oral sex. It’s not much but if I can make you come will you leave?’ I almost laughed at her play on words but I had to keep in character. ‘What makes you think an old broad like you can satisfy me?’ I already had a hard-on that was beginning to throb and she said ‘If I can get you to blow your load than age would seem to be unimportant. What have you got to lose?’
I pulled her from the chair and lowered her to her knees. I dropped my pants and underwear to my ankles. She looked into my eyes for a moment and then began.
Before taking it into her mouth she worked me over with her tongue running the tip of it back and forth, around and around. She tossed her head so that as her mouth did its magic her hair stroked my thighs. Then she took it in. She worked back and forth, gently at first, then with increasing speed and grip. I wanted this to go on but I couldn’t hold out. When I blew it was such a release that I became light-headed. I staggered and grabbed her hair to steady myself.
Holding her like that kept me inside of her which meant that she had to swallow. When I realized what had happened I began to apologize. She said ‘Don’t say a word. That just made it even better. And besides, it’s not the first time that’s happened.’ Then she winked at me and added ‘I seem to have that effect on men.
I untied her and then sat with her on the bed for a while rubbing the rope marks on her wrists. ‘You know you don’t have to stay’ she said ‘I know you’ve probably got better things to do than to hang around with an old broad like me.’
I looked into those heavenly eyes and said ‘What did you buy at the grocery store. I’m feeling a little hungry.’