The Keyholder Pt 4
- 4 years ago
- 28
- 0
I had a female friend who ran an escort service. One winter night she called me and asked if I'd do her a favor. She had just received a call from a 61 year old widow who wanted to have a man visit her and asked if I'd call her.
I had never done anything like this before, but was excited by the idea. I told her, "Yes." I was 33 years old at the time.
The woman explained to me that her husband had died over a year ago and that she had not had sex in all that time and was "very horny and needed a man's cock inside of her!" She explained that she was on a fixed income and could not afford the "escort charge."
I was so turned on by now that I was willing to visit her for free. I had been with women a few years older than me, but one that was 28 years older and so up front with what she wanted had me hard in my pants. I called my friend and told her the woman cancelled due to lack of funds. I then called the woman back and got her address. It was about 10:30PM and I told her I'd be over after I showered.
She asked what I looked like. I told her I was 6'3" tall, 185 lbs., shoulder length brown hair with Hazel eyes. I told her I had a mustache and that people had told me I looked like Sam Elliott. She cooed and said she was getting wet and asked me to please hurry.
I had no idea what she looked like. and ugly or thin and beautiful. But by now it didn't matter to me. The thought of fucking this grandmother was driving me wild! I couldn't wait to get there.
I got out of the car and walked through the snow to her apartment door. It was a full moon and the snow glowed brightly under it's light. I knocked on the door. I heard her voice say, "Just a minute."
Then she called for me to come in. My heart was pounding as I opened the door. It was dark inside and it took my eyes a minute to adjust. It was a basement apartment and there was a long flight of stairs leading down. At the bottom was a soft yellowish glow coming from the right and there at the foot of the steps was my prize.
She was about 5'2" tall, petite with short grey hair, large glasses and wearing a full length, black silk nightie. She nervously clutched her hands together in front of her. She was wrinkled, but not unattractive. As I descended the stairs she moved back towards the direction of the light. I turned the corner and entered her living room.
She looked up at me with her blue eyes and said, "I prayed you wouldn't be a "hunk." Then she said, "You don't want an old wrinkled woman like me."
I couldn't wait to show her how very wrong she was. "Oh yes I do," I told her as I took her in my arms and bent down and pressed my mouth to hers. As we kissed, I looked behind her and saw a lamp on an end table next to a red velvet recliner chair. "Perfect," I thought.
I bent down as we continued kissing and scooped her small body up in my arms and carried her to the chair and laid her in it, pushing it open as I did so. I laid on top of her and we began kissing more passionately. As our tongues explored one another's mouths, my hands began exploring her slim body. I began kissing her face and her neck and then down to her cloth covered, small breasts. I found her nipple, hard beneath the material and began sucking, making it wet with my saliva. Then I kissed down across her stomach and then ducked my head under her nightie. She spread open her legs for me and I marveled at her milk white thighs and hairless pussy.
I began lightly licking up and down the slit between her legs. She twitched a bit as I did so. Then I pushed my tongue inside her, parting her love lips and fully licking her. I found her plump clit and began flicking and twirling it in my mouth. I could hear her softly moaning as I pleasured her. Then I sucked her clit into my mouth and licked as I sucked on her.
My cock was extremely hard and struggling to be released from it's cloth prison. She said she needed a man's cock inside her and I was ready to fulfill her need. I reached down and unbuckled my belt, unbuttoned and unzipped my Levis. My pants fell around my ankles as I rose up to be in a position to enter her.
Looking down at her laying beneath me, I took my hard, throbbing cock in my
right hand and began rubbing it's head along the length of her pussy. The
anticipation of being inside of this grandmother was sweet agony. I could only
imagine how she felt. She gasped as I slowly pushed my love staff inside of her.
I gave her all of my seven and a half inches. Her warm wet pussy gripped my
staff like a velvet glove. I was amazed at how tight she felt as I slowly began
fucking her. This was great! Thrusting myself in and out of her, over and over
again. We fucked for awhile and then I pulled out of her.
I then sat on her couch and removed my boots, socks and pants. She offered me a whiskey and water. I lit a cigarette and as I sipped on my drink, she got down on her knees in front of me and began kissing my still hard cock. "Oh yes," I thought. "Suck me grandma."
As though she could hear my thoughts, she slipped her wet mouth over my cock and began bobbing her head up and down as she sucked on me. I sipped my drink and smoked my cigarette as she worked at pleasuring me. I couldn't help but think how fantastic this evening was for me. I wanted to fuck her again. I wanted to give this old woman the best fuck of her life!
I softly said to her, "Let's go to your bed."
She got up off her knees, took my hand and led me to her bedroom. I took off my shirt and she pushed me backwards so that I fell onto her bed. She then pulled her long night gown off over her head and tossed it aside. Then she climbed up on top of me and slid down onto my stiff cock. I was once again inside of her wonderful hole and she began riding me. I loved the look of her slim naked body and small sagging breasts as she fucked me. I grabbed her hips with my hands and began bucking back. I then raised up and took her nipple into my mouth and suckled on her while we continued screwing.
"Do you like to fuck?" she asked.
I looked up at her and answered, "Oh yes!"
I then put my arm around her and pulling her body close to mine and thrusting my cock fully inside of her, I flipped her light body around so she was on her back and I had remained inside of her. The curtains of her ground level window were open and the light from the full moon lit her bed with a pale, blueish light. With her fully naked body gleaming beneath me, I began giving it to her harder. This was so exciting and she felt so good. I had no idea how good an old woman could be. I hadn't even finished with her and I was thinking about how much I wanted to see her in the future.
She was moaning and tossing her head from side to side as I pounded her. Her legs were now up in the air as I gave her everything I had. I arched my back to give each thrust more power. I wanted to make sure she would want to have me again! I wanted to be her sex toy!
Her moans became louder and quicker. She began to quiver beneath me and I knew she was on the verge of exploding! I pulled out of her. I turned her over and she scrambled to her hands and knees and I entered her from behind and began fucking her dogie style, my hands grasping her hips as I gave her my throbbing manhood over and over again.
"Oh mamma, I love fucking you!" I told her.
She then pushed her face into her pillow and muffled a scream as she released her cum. I reduced to a slow fucking as her body quivered and quaked before me. I slowly pulled out of her and as I curled up next to her, taking her in my arms, I could tell she was crying.
When I asked why, she told me it was because she had wanted us to cum together. I explained that I didn't always cum the first time with a partner.
"It's something we'll have to work on," I told her.
We continued seeing each other about twice a week for over a year. As old blue eyes used to say, "It was a very good year."
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BDSMChastity with Ex as Keyholder Ch. 08bychastity_sissy©"So, that is what you fantasize about? Having my hot boyfriend and me making you our little sissy bitch? Pathetic," my Ex said flipping through the pages of the story I had submitted to her, while I worshipped her sweaty pantyhosed feet per our already established agreement.I still couldn't believe an Ex of mine was actually a hot Hooters girl. Being one with a small, tiny, thing for uniforms, I couldn't believe I had let this one slip...
Chastity with Ex as Keyholder Ch. 06bychastity_sissy©My Ex knew me. She knew me better than I knew myself. She knew it had been a deep, disregarded fantasy of mine to be a helpless maid amongst a variety of men and women, all dressed up in pretty outfits demanding drinks and snacks from the maids passing by.She had, without a doubt, put "the guy" in his place. My cock was completely locked away in full metal, and it would require an ER visit to physically remove the device without a key. I...
Chastity with Ex as Keyholder Ch. 02bychastity_sissy©From what I could remember the following morning, I had definitely done something stupid. My memory became fuzzy after she had left. Just as she had predicted, I surfed the web and looked at my saved cache of porn. Unable to get off on it, I drank more and stayed up later than usual until everything became a blur and I woke up on the couch, still dressed in the corset and nylons.Good thing I had the day off.Work! How could I deal with wearing...
Chastity with Ex as Keyholderbychastity_sissy©Several days off. I was looking forward to it. The days off had been meant for something else, but those plans fell through. Now, I had the weekend plus several extra days. I could barely contain myself as I was excited to try out the new toy I had recently purchased.As soon as I got to my apartment, I checked with the management building and sure enough, the package was there. Before I could do anything else, I had the package opened on my table...
About 10 years ago I was out at a pub for a workmates going away party, not really my scene but the workmate was a good bloke and I really needed some times away from my girlfriend, who I’d being seeing a for 2 about and a half years. But to be honest, it felt like the last few months were just out of routine. Things were on the downturn and weren’t getting any better. It was well and truly beyond its use by date, but I guess both of us were too afraid to move on.Anyway, back to the story.I...
Hope you guys out there enjoy reading as much as I am enjoying my time with this woman.So, I recently graduated from university and came home to visit family before starting my new job later in the year.Sex at university was always temporary and being Pakistani, I have always chosen white girls throughout school, college and university as they seem to have a more open lifestyle. Dating Pakistani girls was always put of as I never seemed to connect until recently, with a woman 10 years my age. ...
This is a true story of my first encounter with an older woman while I was in high school. I had been online the night before trolling through AOL chat rooms at the time and i started talking to a woman who was from the same city as me. After a bit of cybering she sent me her phone number and asked me to call her. While we were chatting she never mentioned her age and I asked her when we were on the phone and she said she was 38, being a freshman in HS this was huge for me especially since...