Life with Daddy Bear

By Chris Michael

Published on Dec 10, 2019

Gay

Life with Daddy Bear Part 12 By Always Horny

This story is about a relationship between consenting adults. The terms "Daddy" and "Son" are meant as indicators of dominant and submissive roles, much like "Bear" and "Cub" would be. The characters are not related.

Daddy had to travel often for his job as a medical supply sales rep. As had become our habit, Daddy always ordered me to abstain from jerking off while he was away. In fact, he had ordered me to stop masturbating altogether unless he was there and it was part of our play. All of my quite substantial sexual needs were met by Daddy or on rare occasions Andre. Of course he still had fun with me while he was away. I'm sure that he had some "special instructions" for me that would keep me horny. On the day before he was supposed to leave he instructed me to strip and get to the play room.

"Ok son get me naked". I undressed him and folded everything neatly.

"Son, I've got a surprise for you but first a warm up - when was your mom born son?"

"1956 Daddy"

"HMM, 19 plus 56 equals 75, what do you say to 75 spanks"? Do you want more than that, Son? "Oh yes Daddy" "Please spank me long and hard; as long as you want to".

"We'll see, maybe less maybe more"

"Yes, Daddy".

"No need to count son, just relax and enjoy."

Now you might be thinking that 75 or more spanks from a powerful man like Daddy would be too much, but Daddy had a finely calibrated sense of my arousal and tolerance levels regarding spanking. If the number of spanks I was to receive was high, say above 50, he would often starts fairly light and make the spanks harder as he went. The intent was a sore (but not agonizing) bright red ass that always supercharged my cock and balls and made me super horny. When he was spanking me he would mix in a little finger fucking, ball squeezing, or head teasing to make it sexy.

"Here we go" Spank, Spank, Spank, Spank, Spank.....he did this for about ten times then stopped and tied my balls up tight with some para cord. He left a lead on the cord so he tug on it a bit if he wanted to.

Spank, Spank, Spank.... After a while he stopped and rubbed my tight hole in little circles.

"Mmmmmnn, Daddy!" I said squirming and grinding on his thigh.

"You like that son?"

"Yes Daddy"

I heard a lube bottle snap open and then felt his fat finger push insistently into my boyhole.

"Oh God" I moaned.

He tugged on the cord, pulling by balls down, and gave my prostate a thorough rubbing with his rough finger.

"OH GOD! OHHH!"

"Shall I add a finger, son?" This was not really a question and he sank a second finder deep in my ass. It felt so fucking good my cock was oozing precum like mad.

"Oh Daddy, please fuck me!"

"Patience my boy, I've got to wind you up a bit, prolong your teasing, that makes it more fun for me. I enjoy watching you turn into a raging slut desperate to cum!"

Daddy had recently added edging to my sexual torments. I shuddered thinking how long he would keep me desperate today. Thankfully he always let me blow a big load and usually fed it to me afterwards.

He commenced spanking me for a long time gradually increasing the force and rapidity of the spanks making my ass really sting. He paused to squeeze my balls adding a few ball slaps to go with it.

"Ugh" I grunted.

He continued finger fucking me, making me ooh and ahh quite a bit, squirming my hips, and grinding my cock on his hairy thigh.

He suddenly pulled his finger out of my ass and said, "On your knees boy!"

I knelt before him. I starting at his big sweaty balls, tongue bathing each one thoroughly, then made my way up his thick shaft, kissing and licking it slowly until I reached his sensitive glans. I concentrated on delivering maximum pleasure to him, slavishly licking all around his cock head before taking his hard cock all the way down my throat. I had perfected this and he really liked it.

Daddy let out a low growl. "God, son, you are one talented cock sucker! Easy son, we have to slow down so I don't nut".

I paused and said "That's OK Daddy, I don't mind".

He rubbed my head affectionately. "I know son, you are such a giving lover; it's one of the reasons I love you so much. How about we have a nice fuck on the saw horse? I'll put your cock in the cum sleeve."

"Oh yes daddy! Please do that!"

Daddy loved to make sexual contraptions and he had rigged up a squishy jelly masturbator sleeve on the sawhorse. The sleeve was especially delightful because it had a little bulb pump that would tighten it around my cock when he squeezed the bulb. It took a little trial and error, but he got it arranged so that my cock would fuck the sleeve as he was fucking me. This way I could cum without him having to bother reaching around to stroke me off; he could just fuck away and I could cum whenever the urge arose. He claimed to love the way my anus spasmed on his cock when I came. Daddy had a lot of stamina and could fuck for a long time, sometimes I came twice!

I smiled and started back on his cock head. He let me for a bit then stood me up took my hand and led me to the saw horse.

I got into position on the horse, ass up as always. He gave me my final ten spanks, real hard ones, untied my balls, then squirted a lot of lube up my hole using a big plastic syringe that he had previously filled with lube. Daddy had access to a lot of medical equipment like this because of his job. He repurposed some of it to add a bit of extra kink to our play. He lubed my little cock toy up also and inflated it. Thus prepared he pushed his big cock in me slowly until he was balls deep.

"Ohhh" I moaned, the spanking and fingering had made me very well prepared for a nice fuck. The feeling of my anus widening to accept him as he entered me was exquisite. He fucked me full length slowly and when his hips hit my ass they pushed my cock through the sleeve.

He kept at that slow deliberate pace for some time making my cock drool but not cum. The feeling of his big knob head rubbing over my prostate was exquisite. I was his total butt slut and Daddy knew that I was insatiable. He could fuck me all night and I would love it! I was his complete and total bottom; I'd do any perverse sexual thing he asked. I think it scared him a little, to be honest.

He gradually picked up the pace until he was fucking me hard. This of course increased the pace that I was fucking the sleeve. I was panting hard and could feel my orgasm building up.

"Oh Daddy, I'm gonna cum soon!

"Not yet son, try to hold off, let's go for simultaneous orgasms, OK?"

"Ohhh, OK Daddy......but the sleeve is....going to force it out" I said between moans.

"OK son, hang on, tighten your sexy ass down on my cock."

He started pounding me real fast and hard as I squeezed his cock with my asshole. I heard his breath quicken.

"OK shoot now son, shoot now!"

With one more forward thrust through the cock sleeve, I exploded, blowing my load. My climactic anal spasms sent Daddy over the edge and he came deep in my bowels.

Daddy stood there with his cock impaled in me enjoying the final little shivers of his orgasm before easing his meat out of me.

"Holy fuck, Son! " "That was incredible!"

I had taken quite a shagging and I was a bit weak getting off the saw horse. He didn't feed me the goo that I shot on the saw horse, just left it there to dry on the faux leather padding. Sometimes he fed me the spilled cum, sometimes it just dried on the horse. Daddy claimed the funk of dried cum in the play room turned him on. I had to agree.

Daddy helped me off it and we retreated to our usual post sex hot shower. I kissed him under the spray and said "I love you Daddy".

"I love you too Son".

I smiled and nuzzled in his hairy armpit for a while enjoying the closeness and warm spray of the shower. I felt a different kind of warm spray on my leg and knew that daddy was pissing, we always pissed in the shower. I felt the urge to pee also and just simply released it, on him, on me, wherever.

After a light dinner of sandwiches, chips, and beer, we just chilled. Daddy watched Sunday Night Football, and I read a book. We enjoyed a sweet night of cuddling and spooning. I drove him to the airport the next morning so he could go on his trip. Of course I sucked him off in the truck right before he had to check in for his flight, then I headed to my folks house.

I hadn't seen my mom and dad for a while, and I had made plans to take them out to lunch. I was a bit nervous. I was planning on coming out to them (finally!), because I wanted to, but also because I wanted them to meet Glen. I wasn't sure exactly when and how to tell them. I finally decided to take them to lunch first and tell them in private afterward back at their house.

We ate at a favorite restaurant of theirs and I was pretty quiet. They were surprised at my changed appearance and asked me about it. I didn't mention Glen, but did give them some truthful information; that I was over my failed marriage and had been taking stock of my life. I had started exercising and eating better. I had also decided to be a little more ambitious at work. I explained that I had been looking to advance in my company and had been accepted into an underwriting training program. I was out of the mail room. I had to pass a series of exams and an apprentice period, but so far it looked promising!

"Oh Drew that's terrific!" mom said.

When we got back to their house we went into their living room. Dad and I had sodas, mom had tea. I asked them about their jobs; they were planning on retiring to Florida in just a few years. Dad said, "you know son, same old, same o". Mom just nodded her agreement with dad.

"Actually, there is something that I have to tell you, but didn't want to at the restaurant."

"Oh" mom said, with a concerned look on her face.

"Don't worry, it's good news, it's just on a very personal subject. Since my divorce I've done a lot of thinking, a great deal actually, and I need to tell you something important, and I hope that you will be OK with it. I recently discovered, well more like acknowledged to myself, that I am gay."

They didn't say anything, which I took as a que to continue.

"About a year ago I met someone, a wonderful guy named Glen, and we've become close. I hope that you are OK with it."

After a lingering pause to digest this major news, Dad said, "Why wouldn't we be son?" "We're not THAT old and we are fairly liberal in our low key way. I think that your mom and I need a moment to let it sink in is all."

"That's fair" I said. "Thank you for being so understanding about it."

I proceeded to tell them all about him, well you know, not all the stuff, just the things you can tell your parents. I was so relieved that they were so open to my being gay that I started to get emotional.

"Mom rested her hand on my arm and said' Why don't you bring Glen to Thanksgiving dinner at our house?"

"That would be great mom, thanks. What can we bring?' "Oh, just bring yourselves and a good appetite".

I knew that she was going to say something like this, but I insisted. "Mom, I really would like to bring something how about a vegetable side dish like stewed carrots or something?"

She looked at me amused, "You cook?"

"Well, I like to eat so yeah I cook", I said, laughing".

"OK", she said, "stewed carrots it is".

When I got home I went down to the play room to read the special instructions Daddy always left for me on the saw horse. He always wrote the instructions on a nice note card. Next to the note was a small gift wrapped box "Son, I'm only going to be gone for three days, that's not very long to build up your frustration level, so I have to intensify your self-torture sessions a bit."

  1. Every morning self-fuck yourself with you pink dildo for fifteen minutes 2. Every afternoon at exactly 5:00 pm, I want you to insert a new butt toy up your ass. It's in the box 3. Other sex chores as needed "Do this exact routine for the next two days. On Friday, the last day, do the self fucking, and butt toy insertion, but instead of pillow humping, I want you to edge yourself for 30 minutes by masturbating to "almost" completion, then stopping not allowing yourself to climax. Repeat this process until the thirty minutes is up. DO NOT MAKE YOURSELF CUM AT ANY TIME WHILE I'M GONE! UNDERSTOOD!"

"Good boy".

"Love, Daddy".

Whoa, Daddy sure new how to press my buttons. I had a good size lump in my pants after reading these orders. I picked up the box and opened it. My jaw dropped! Inside was a black wishbone shaped prostate massager. It looked like a high end one too. The package clearly indicated that it included an android smartphone app for "remote control" use. I knew what that meant. I had a little involuntary shiver. I was doomed!

The box had a second note in it just concerning the butt toy.

"Son, remove and clean this massager. Download the app that is included to your phone, then text me the link for the app and the download code. Use the special lube that comes with this toy. Don't use any other lube on yourself or the toy when you use it. Clean and dry it after every use. Take good care of it. It was a little expensive".

"Love, Daddy".

Wow! I was in for a ride! It being the first day, I got to my sexual chores. I went and got the pink dildo, stripped naked, lubed up and rode the dildo for fifteen minutes. I was already horny from the kinky instructions and surprise present from Daddy. I had to be real careful not to cum. I managed not to and stopped with relief at the fifteen minute mark.

I cleaned up and headed into work, trying not to think about the sex instructions anymore for the time being. I had learned how to compartmentalize my work "headspace" from erotic thoughts about Daddy and his kinky sexual instructions. I needed to focus on doing a good job and succeeding in this insurance underwriting gig. It sounds rather dull, but actually was pretty interesting, and paid more than the mail room job. Daddy and I had discussed it a good deal. It was his idea to call off all of our sexual antics at work, for both of us. No more sexting, bathroom jerk offs, the on-call sex, everything. This was actually a smart decision.

After work I went directly home. I immediately downloaded the app and texted the app info to Daddy.

At five I lubed up my ass and the massager and carefully inserted it in the way that the printed instructions showed. At 5:10 Daddy called me.

"Hi Son, Is the massager in you?"

"Yes, Daddy".

"OK, go into the bedroom and get comfy on the bed. Crank the heat a bit so you don't get chilled. Lie on your back and relax. Leave everything to me".

"But Daddy, what if I cum?"

"I said, "don't make yourself cum" I fully intend to make you cum with this thing - it better make you see stars for what it costs!"

"Now son, I don't rightly know how this thing works or what it feels like. I'm going to run you through the different settings and will be asking you how they each feel, which ones you like. I also don't know if you will have a normal ejaculation, a kind of ejaculation, or a just warm fuzzy feeling. There is no right answer. The whole point is just enjoy whatever happens.

He ran me through the various ways the massager vibrated; internally on the prostate, externally on the part that rested on your taint, both internal and external at the same time, regular pulses, random, pulses, synced to music. I couldn't quite tell but I think I liked the random and music setting the best.

The thing made me moan softly and really relax into the bed. After just the initial trial I had some dribbly drool like precum leaking out of my cock and a euphoric feeling not unlike when you take a pain killer that the dentist prescribed for you. It was awesome and a little different from a straight on orgasm. We stopped and just chatted for a while. Then a funny thing happened. I felt really good and happy for a long time after I took the toy out. I wondered if this was part of the "orgasm".

We continued with our nightly remote sessions. Daddy was starting to get the hang of keeping my ass and prostate very happy via remote control. He had me writhing and gasping for our next massage session.

On the final night I was getting truly desperate for Daddy.

Oh daddy, I need you! I need your cock! I really miss you! I'm coming with you on the next business trip!"

He laughed saying "OK son, I miss you too, and I would love to have you along. I'd love a nice blowjob after a difficult sales call".

"Oh you'd get it Daddy, you'd get it". We hung up and I spent the night thinking about the next day. I had taken the day off to pick him up. I had pleasant thoughts of the marathon fucking and sucking session I was in for. Daddy had given me an extra chore of humping a soft pillow for fifteen minutes saying he needed me desperate to cum by tomorrow. I couldn't wait!

To Be Continued........

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Next: Chapter 13


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