Weekend with Daddy Bear By "Always Horny"
This story is about an erotic encounter between two consenting adults. The terms "Daddy" and "Son" are meant as indicators of dominant and submissive rolls, much like "Bear" and "Cub" would be. The characters are not related.
I am a recently divorced bisexual man in my early thirties. After ten years in a sex-starved marriage, I had finally had enough. I've always had a big thing for older dominant daddy bears. I had been getting off on daddy bear stories for years on Nifty.org. I finally decided that I really wanted to live out my fantasies at least one time. I posted a Missed Connections post on Craigslist, cheekily claiming "missed daddy bear, can you help me find him?"
I received several replies and was immediately drawn to one from an older guy named Glen. He described himself as a big, slightly overweight, bearish guy, 55. He asked me what I was into. I replied that I was a newbie who wanted to explore my sexuality with a patient authoritative older man. I was turned on by being submissive and was looking for someone who didn't mind a little role play. I was nervous about admitting this, thinking it might be a turn off for him. He replied right back saying that he didn't mind at all. I sent back a grateful email describing the ways I wanted to please "daddy", or "sir".
He quickly took over the conversation, replying that I was to call him daddy. He stated that he had to go away on business for three weeks, but we could meet when he got back. We set a date.
Daddy then sent me a set of rules that I was to follow. I was allowed to jack off once now, catch my cum in my hand, and eat it. Then I was not to cum more than twice a week until we met, eating my cum each time. If I got too frustrated I was allowed to jack off up to four times in a week, but this would have consequences. I was to keep a log of when I jerked off and what I was thinking about when I did.
I was not to engage in sexual activity with anyone else. I was instructed to continue going to the gym focusing on leg and butt exercises. I was not to shave my ass or pubes and to not touch my ass at all. I was to send daddy my waist measurements, cock size, and ball size. He assumed (correctly) that my anus was very small and tight. He might be making some purchases for which he may ask me to split the cost.
Before arrival: I was ordered not to jerk off for one week prior to our meeting, but to think about daddy often.
I was to purchase a small Fleets enema and clean out before arriving. I was to stay hydrated and get a lot of sleep on the days prior to our meeting. He told me to arrive showered and shaved, wearing khakis, white briefs, a t shirt, and a clean oxford shirt. Also to pack a small weekend bag with spare undies, socks, pants and a shirt, as I would be staying the whole weekend, if we clicked.
The week leading up to our meeting was sweet torture, I was hard or semi-hard the whole time which was hard to hide at work. I desperately wanted to jerk off but managed to hold off, although my cock was drooling precum the whole time. I was to take Friday off and arrive at noon sharp. At nine I gave myself the enema, showered and dressed. I drove the 45 minutes to daddy's house. I arrived in his town slightly early. I decided to just sit in a commuter lot until the time got closer to twelve; I simply couldn't go to a store or caf‚ with my raging erection on display.
With great anticipation, I arrived at daddy's house. I walked to the door and rang the bell. The door was opened and my heart stopped. Before me stood a bear of a man - about 6'2, with short salt and pepper hair and a full beard. He had huge arms and chest, thick legs and a rounded belly.
He let me in. He said, "Boy, while we are here, you can call me daddy, if we go out and you need to address me you can call me Glen. Now take off all of your clothes, fold them neatly, and put them on this table".
After I did that he told me to lean forward and spread my cheeks so that he could inspect my ass. "Did you clean out as instructed?
"Yes" I said.
"Yes what"? "Yes daddy".
"Good. Did you hold off cumming this week"? "Yes daddy".
"Let me see your jerk off log. I see that you jerked off more than what was permitted. Where you able to concentrate at work last week"?
"Not very well daddy, but I tried".
"Come here"! We entered a small library. He said, "I want you to undress daddy, leaving my briefs on, and fold my clothes. I like to spank unfettered".
He pulled out a desk chair and ordered me over his lap.
"I'm going to spank you now. I doubt you'll cum, but if you feel like you are going to say, "Daddy I might cum". I don't want you nutting just yet. I think jerking off more than allowed earns you 50 swats to your nice tight buns".
He commenced spanking, telling me to count the spanks. He had big calloused hands, and he spanked me hard. By 50 spanks, I was shaking all over with a bright red ass. He sat me on his lap, "Are you OK son? He asked", wiping away a tear.
"Yes, daddy".
He kissed me and said "Good, now go to the kitchen and get me a beer and a glass of water for yourself". I did as I was told.
"Kneel" he said. He stood and said, "Remove my underwear".
As I did so his thick half hard cock flopped out. He had huge balls and a thick growth of pubic hair. He spanked me in the face with his big cock and said "open" "suck me slowly until I say, don't use your hands".
I couldn't believe it was finally happening, my years of daddy fantasizing was being fulfilled. I could only get about half of his big cock in my mouth, but I sucked him earnestly, wanting to please my daddy. As I was savoring his tasty cock, He said, "Use your tongue and lips on the shaft and balls as well".
After a while daddy said, "Now suck faster and use your hand to jerk me".
After about a minute I was rewarded by daddy's big salty load in my mouth. "Now swallow son, and clean off my cock". I swallowed his load and licked the residual cum clean as well as the cum oozing from his piss slit.
"Good boy", he said.
"Come over here to the couch and lay across my lap again".
I was a bit apprehensive, "Don't worry, I'm not going to spank you again".
I lay across his lap. My hard cock trapped against his beefy thighs.
"Spread your legs a little bit."
This exposed my asshole and made me quiver, my cock freely drooling. He took a bottle of lube off the side table and gently rubbed some over my asshole with his finger. I gave a little jump when he did this he. He chuckled, saying, "I see you have a very sensitive little hole there son, that's very good. We are going to have to work on opening you up, if you are going to be able to take my cock up your ass".
With that he gently slid his finger in my hole, provoking a moan from me.
"You were such a good boy in taking your spanking and sucking daddy's cock that I think you deserve to cum, but hold off as long as you can".
Then he slowly but deliberately began to finger fuck me. The feeling was indescribable. My breath quickened, he added a second finger and picked up speed saying, "hump daddy's thigh and cum anytime, boy".
With that, I released a week's worth of cum onto his thigh and couch. I lay across his lap fully sated. He withdrew his fingers, eliciting a little squeal from me. He laughed, saying, "You have a very hungry hole son. That's going to make daddy very happy! Now let's get cleaned up."
We were both sticky from my climax on daddy's lap. Daddy led me to his bathroom which had a large shower in it. He turned on the shower and said,
"Get in there boy".
Once in the shower Daddy gave me a tender kiss, his tongue finding mine. I was melting but was nervous, I didn't want to start to fall in love or expose myself emotionally too soon. Daddy seemed to sense this, he cupped my ass and whispered, "Relax, you're safe here, Daddy will never hurt you".
This was so kind and reassuring to me that I quickly did relax.
"Get on your knees".
With his back blocking the shower spray, daddy said, "I always need to piss after a good cum, son. Ever tasted a man's piss before? "No Daddy"
Daddy pushed me to my knees, retracted his foreskin and released a powerful stream of piss directly in my face.
"Open your mouth" and I instantly obeyed him.
"Drink Daddy's piss, Son"
I gagged a little bit from the taste. Daddy said, "That's Ok son perhaps you're not ready for that yet. A little taste is enough".
He stood me up and continued to piss on my cock and balls.
He then said, "Clean daddy up good now".
As I reached for the soap Daddy said, "No, with your tongue, son". "Start with my nipples and armpits"
He raised his arm and I obeyed, lapping his hairy armpit. I moaned as he slipped a soapy finger into my ass. I found the whole thing intensely arousing. I was rock hard and ready to cum again.
"Keep going" he said pushing me downward. I continued, licking his big belly and sucking his cock once again.
"OK" he said, "that's enough of that for now, you'll get plenty of Daddy's cock later. I need you to clean daddy's balls and ass. And do a thorough job of it!"
After a while of licking daddy's big balls he said "move on back and clean it all".
I did just that, licking daddy's taint and furry ass cheeks. I made a furtive lick close to Daddy's asshole.
He solved my nervousness by bending forward and backing up trapping, my head between his ass and the wall. My face was buried in his muscular ass, and my nose was right at his asshole, smelling his musky odor. I licked his asshole with fervor for at least a minute, then daddy stood up straight, releasing my face.
"Good boy" he said kissing me once more.
Daddy lathered up his hands with soap and washed me from head to toe, paying particular attention to my groin and ass crack. He gave me the soap bar and told me to soap him up as well. After I did this we stood face to face and he sensuously started to rub his cock against mine while he kissed me slowly. This whole "hot" shower with daddy had me so horny and excited that I knew I wanted him to fuck me. I was dying to give myself totally to daddy.
I whispered in his ear, "Please fuck me Daddy".
We got out of the shower and quickly dried off.
Daddy took my hand and led me to his bedroom where he laid me softly on my belly, propping pillows under my hips raising my ass up for his pleasure. He lubed up my hole really good repeating the finger stretching that he had done earlier. He got up behind me and whispered in my ear, "Ok son, daddy is going to give you his cock and cum, don't worry daddy will be gentle."
I felt daddy behind me gently pushing his cock against my pucker. He said "push out like you do when you have to go to the bathroom".
I did as he said and his big cock head popped in. It felt huge! He gave me a moment to adjust to his cock then slowly worked it all the way into my asshole. He slowly began to fuck me. It felt incredible and my cock was leaking profusely all over his pillows. He gradually built up speed to the point where he was fucking me fast and deep. He went on for what seemed like a good five minutes with me moaning and panting the whole time. He leaned over my back whispering,
"Do you want to cum with daddy?"
"Yes Daddy"! I urgently replied.
He flipped me over and continued fucking me. He squirted some lube on my cock and began stroking it as he fucked me. I felt my climax building very quickly.
"Oh daddy, I'm close!" I panted.
"Then cum boy!"
I released spurt after spurt of cum onto my face, chest and belly. Daddy flipped me over so I was ass up again and continued to pound me rapidly. I soon heard him growl and release his seed into me. Spent, he lay on top of me for a moment, then slid out of me. He whispered in my ear, "We are going to have so much fun this weekend!"
I smiled. This was even better than I had dreamed
To be continued.....