First of all donate to NIFTY. They have provided me the platform for these types of true tales and allowed me to meet other great authors.
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Also if you remember me from writing "The Kid and the Suit Maker", I am absolutely stunned with all the positive feedback. I know you all want to know about my grandfather, however I just cannot put it into words yet so you'll have to be patient.
However for your entertainment this series is about my Craigslist "hook up" days. I hope you'll find it interesting. It certainly was for me.
Obviously this material is for those 18 and over. And by now if you don't like the subject material it's a "you" problem.
As usual feel free to drop me a line (afoolishringmaster@aol.com)
"Oh how I miss Craigslist Part 1 - The Executive"
You have no idea how bummed that Craigslist has to shut down the personals. And yes, I know the reason why. But it doesn't mean I have to like it. I had a grand old time playing with my "Grandpas". These men for the most part were happily married, raised wonderful kids and for the most part "hetero". Usually they played with men due to the Mrs. having no desire for sex, or due to disease no longer could have sex. They like to remember their "college days", or their fooling around in their youth. So this is the first time I went on a CL hookup.
I had to have been 35 at the time. Since the Mrs. and I weren't having sex anymore, I finally broke down and started looking through CL for "Mr. Right now". Although I was an "old person", I love age play so "daddy/grandpa" could fulfill our fantasy if but for a short time.
No mind you reading the various wants, needs, and desires was a definite eye opener. Never was into the rough stuff, anal, pain, or verbal humiliation. So I plucked up the courage and posted my own ad.
CL: "Hi Grandpa. Remember the day you caught me reading your Playboy's? Instead of punishing me, you led me to the bathroom to teach me "man stuff". Well I may be in my 30's but I'm still that naughty nine year old that always wanted to suck on your lollipop. I know Grandpa is a nice person who never mistreats his boy.
And my inbox explodes....
The first dozen or so responses were rather revolting. I was already second guessing myself. But there was this one response that changed my middle age doldrums.
CL: " Hello this is Grandpa. I miss my grandson so much that I'm in town tonight at the Omni Hotel. If you can tell me what you require, I'll have them ready by 7pm. BTW I'm 60, and 6 feet tall and my hair is white as snow. A bit of a gut, but your favorite "pacifier" is still a strong 7". I won't post a pic and don't expect the same from you."
Mind blown! And this had to be around noontime. Being a Federal Civil Servant and a desk jockey to boot made it easy to hide my raging hard on that was renting in my slacks. I'm 6' 2", about 200lbs with jet black hair. I could still pass for younger and since I really didn't work out, I still had a "toddler bod" (non-defined pecs, puppy fat on the tummy, etc), so the physical aspects of my favorite role play was still there.
So I replied, "Hi Grandpa! I miss you very much! Can you give me a bubble bath? I want to be nice and clean for you. After that can we kiss and snuggle? And can you show me again how to 69? I'm not into the anal stuff men do, but I'll do my best to please you as always."
It had to of been an hour later (I mean we all have to earn a paycheck), when he replied back.
"Hi grandson. I've just finished with my meeting. I think it's your birthday coming up so I'll hit the store and pick up some Mr. Bubble, get you a happy birthday balloon, and I found this cute teddy bear from the airport. How can I be sure you can be at my hotel tonight? And yes, I love the idea of cuddles versus fucking. What a smart and thoughtful boy you are."
"Well Grandpa. I can see the hotel from my office. And if you go to the hotel bar you'll see a gentleman in a grey suit with a Raider's cap on. Just sit next to me and say "teddy bear" and I'll know it's you. We'll have a drink to make sure we click. And if we do I'll gladly come to your room."
Grandpa: "Ok be there at 7pm sharp please. This is going to be fun."
After an eternity, finished my work day. Survived my commute home. Told the Mrs. that I was seeing a client (very common for me, so the lie was easy), and hopped in the shower to ensure my parts were all clean and clean shaven. My pits and crotch were shaved to finish the effect. Went back into the bedroom and changed to my favorite grey suit, grabbed my Raiders hat and left home to grab a bite to eat prior to the encounter.
Now before I worked for the Feds, I've worked at enough hotels to know how to get in an out without being noticed by the hotel "dicks". The Omni had the bar located just left of the entrance. I'm notorious for showing up early. I sat at the corner of the bar where it wasn't as noisy, ordered my beer and then I saw him.
Grandpa was 6' tall, his hair was pure white as snow, and carried himself like a professional. He scanned the bar and saw my hat. He glides towards the empty seat and asks the bartender for a martini. As soon as he gets his drink, he waits for the bartender to leave and he says, "I love coming to this town in my travels but where can I buy a teddy bear for my grandson?"
Now I'm trying to play this cool. This was my first hookup via CL. So inside I'm quivering in anticipation. So I take a swig of my beer and replied, "I'm so glad you're here. I have one simple rule, I won't ask you to do anything you're uncomfortable doing and all I ask is for the same." His smile lit up the bar.
He slides me a room key. "Room 912", He said. "Let me finish my drink and come up in 10 minutes." He finishes his drink, leaves a $20 at the bar and exits. Now I'm trying very, very hard to nurse my beer. Must of stared at my watch during the time. 10 minutes pass and I left my money for the bartender and headed to the elevator.
I knock on the door. He opens it, and he was already in his bathrobe. I can tell already that he was smooth and not hairy. I enter the room and he closes the door. "Happy Birthday! Let's get you washed up first. I've got some presents for you, but you can't open them up just yet." He said with a Cheshire Cat like grin.
I grabbed my hangar for the Suit and I slowly undressed in front of him. When it came to my slacks, I gave him a look and asked, "Grandpa can you help me?"
"Of course." He unbuckled my belt, opened my two snaps, unzipped my fly, and then pulled them down to see my Batman Underoos (I was skinny at the waist, so I could still pull this off. The Mrs. never knew this side of me).
"Oh my!" He exclaimed. He took my hand and guided me towards the bathroom. Inside he already had two pillows by the tub for his knees. The tub was a picturesque bubble bath with the bottle displayed. He had me dip a toe in the water to ensure the temperature was right. I nodded that it was fine and he takes off my undies. My 7" cock was throbbing massive, and his eyes were in total rapture. He undo's his robe and I swear our cocks were identical except that he was uncut. He had these sexy spidery silver pubes. I get in the tub and with a washcloth took his time "cleaning me". I'm in pure heaven. He gently asks for me to turn over and throughly cleans my backside. I'm shocked that I didn't shoot my load then and there. I turned over and he scooped some of the bubbles to form a beard. He wanted to take a pic, but I politely said no. Nothing was safe on the internet as far as I was concerned.
With the bath "finished", I step out of the tub. Grandpa took his tide toweling me off and playing with my cock. His lips kissed the head of my cock like no one else ever did. "Ready for your presents kiddo?"
"Oh Grandpa, you shouldn't of have gone to all the trouble." I replied and we both giggled.
The king size bed had a small white teddy bear and at the nightstand was a Happy Birthday balloon. So I crawled on the bed and start naughtily posing with the bear. I said "You can take pics so long as my face doesn't appear in them." He takes a few snaps with his cellphone. Grandpa let me review them and I approved. Next thing he does was to grab the balloon and ties it to my hard cock. The helium filled balloon lifts my cock in the air and he took more snaps. Once that was done he pulls the knot down to the base of my cock and steers me towards the chair and ottoman.
Our first kiss was chaste. We gently explored each other. The touch and feel of his skin sent me to Nirvana. He gently pushes me down to the chair. With him on the ottoman he swirls his tongue at the head of my cock and worked his way down to the most incredible blow job. I'm fighting like hell not to explode, but after 10 minutes, I shot my pulsating load down his throat. He swallowed it like a pro. He then lays on the bed and waves me over.
"I miss my pacifier Grandpa." I said
"I would never deny anything from my boy." He said.
So moving the ballon string for convenience, we started kissing again. Then with my tongue, I slowly ran it from chest to cock. The soft moaning told be he was into it big time. His nipples were perky but soft and I suckled on them. His cock was warm and inviting. And I blew him for a good half hour. Whenever I felt he was close, I'd move to a different spot. I could tell we were making fantasy into reality. When I got him to finally climax and let him spurt his hot hornet down my gullet. We grinned and discovered the type of euphoria that only men can understand. He sat up on the bed, I laid my head on his chest so he could absent mindedly stroke my hair.
"What brings you here Grandpa?" I asked.
"I just finished a land deal for oil, gas and mineral rights. If the lobbyists didn't insist on a post celebration, I'd have more stuff prepared for you. Being an executive has it's privileges." He said. "And you?"
"I work for the Federal Government. I've discovered my wife and I weren't sexually compatible. I wanted to rekindle my "bi" side again. I was always a sucker for older men who are kind and gentle. I can't thank you enough for the experience." I replied.
For the next hour we cuddled silently. He made me feel safe and content. Sadly the alarm on my phone told me I had to go. I untied the balloon and started to get dressed. Since I wore a hat I could hide the tell tale signs of our activities. He got up, put on his robe and handed me the teddy bear. We kissed languishly not wanting to break the moment. And then I exited the room.
Sadly, we never hooked up again. But that teddy bear still sits on my desk hoping one day we meet again.
The end.