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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.
Weekend with Daddy Bear: Saturday By Always Horny
After our vigorous cherry-popping fuck, daddy and I were both sexually exhausted. We decided to order a pizza for delivery. Daddy had to go find a robe so that he could pay the delivery guy. After we ate, we snuggled naked on the couch under a big blanket and watched a movie. I had been naked since arriving, but somehow that didn't seem weird to me. Toward the end of the film I grew sleepy. Daddy picked me up and tucked me into his bed, then slid into bed and spooned up close holding me tightly. I was soon fast asleep.
When we woke up at 6 am daddy said "let's hit the gym". Daddy told me, "you stay here; daddy's got to get his gear on". He came back wearing only a jockstrap. The jockstrap was semi see-through from age and use. It had discolored stains all over it. The image of daddy's big bulge hanging under his belly encased in that dirty jockstrap was sexy as hell and had my mouth watering. He intentionally turned around to get a water bottle off his bureau, showing me his big hairy ass.
"You getting horny, son?"
Hell yes I was and he knew it! "Yes daddy, but I really need to pee first".
He said "Ok, follow me". He led me, still nude, to the bathroom and he got in the shower. He said "come here, son"
I was confused, why was he in the shower?
He said firmly "do as your told boy!"
I quickly obeyed and got in the shower. He grabbed me bringing me close. He pulled the waist band of his jock away from his body, and bent his knees a bit getting down to my height and said. "Go ahead and pee, son". Did he really want me to pee in his jockstrap? He was the daddy and he told me to do it so I did, letting loose my morning pee.
He said "Ok now son, I'm glad you feel better, but daddy can't workout in a wet jockstrap, you're going to have to clean me up a bit", pushing me down to my knees. "Suck on daddy's jock son, use your mouth to get the piss out of the fabric".
This whole scene was like something out of a porn mag or raunch flick! Oh well, I wanted a dominant daddy bear after all, and that's exactly what I was getting, in spades! I did as he instructed, sucking on his big package though his jock, tasting my own piss in the process. He took hold of my chin and looked me in the eye saying," keep nursing on daddy's jock, boy, don't stop". As I continued to worship his amazing junk through his jock, I noticed it was getting wetter. It took me a few seconds to realize that Daddy was pissing! He pressed my head to his crotch, saying "keep going boy, lap it up, swallow daddy's piss."
I did as he told me to swallowing all that I could, with some dribbling down my face. He continued his piss for a long time, shuddering at the final dribbles. I continued nursing on his manly bulge encased in the jock.
"You know what", he said, shedding his jockstrap, "fuck the gym. Suck my cock son!" After a few minutes, he said, "Son, you really need more oral training, but right now daddy needs your sweet ass more. Stand up, turn around and bend over". After a preliminary lube up of my asshole, daddy grabbed my hips and stuffed his massive cock in my ass, burying it to the hilt. This was no slow seductive warm- up fuck like last night; this was daddy fulfilling his needs, thrusting quickly and powerfully. I was daddy's horny little slut completely by now, thoroughly relishing the delicious ass fucking he was giving me. Daddy stopped for a moment, grabbed the lube and greased up his hand and my cock. He squirted some on his cock too to make his fucking easier on my ass. He commenced fucking and simultaneously reached around and stroked me off. I came first, of course, crying out and splattering my cum on the shower wall. He continued fucking me intently, eventually ramming his cock in balls deep and filling my ass with his cum.
He said, "Whew"! You've got a sweet ass Son! He turned me around facing him, saying, "You OK boy"?
"Yes Daddy, very much so".
He smiled leaned in and gave me a deep kiss. He turned on the shower water and washed us both up quickly. We got out dried off and he said" let's get breakfast". We got into his pickup truck and headed downtown to a diner he liked.
On the ride down we were quiet for a while, and I was thinking, "how am I ever going to go back to my apartment and job?" In less than 24 hours, I had become an entirely changed person. I was no longer just a horny dude looking for a daddy bear scene; I was a horny dude that was getting firmly attached to this particular bear. This was morphing from role play into reality. It scared me a little, hell it scared me a lot!
As if reading my mind, he asked "how are you feeling son, tell me your thoughts". I honestly told him my apprehensions, that I was getting sucked in too deep to our fantasy role play, that I was afraid I was changing due to the intensity of it and also of his gentle kindness toward me. He put a hand on my shoulder, rubbing it, and said, "Well it's the same for me Drew (using my real name and signaling that he was "out of character"), "I was expecting a kinky, spunk-filled weekend, nothing more, but your trust and eagerness to please me has affected me too. I'll tell you what, let's drop the whole daddy/son thing for a bit and just relax and have breakfast and talk for a bit."
During breakfast we talked freely about ourselves, our families, jobs, general backgrounds. He told me that he was a retired Navy medic, who now worked as a sales rep for a medical supply company. I told him I was recently divorced and was at loose ends, somewhat, and that I worked in the mail room and copy center of an insurance company. It didn't pay much, but was full-time and had good benefits. He asked me if I had kids and about my living situation. I told him I didn't have kids and that I lived alone in a one bedroom apartment. I touched briefly on my marriage, saying that we broke up over my wife's complete lack of interest in me sexually. I got fed up with asking for sex only to get rejected time after time. When I asked for a divorce, she didn't object.
After breakfast, Glen said, "Well Ok son, we seem to really be enjoying one another, no reason to stop just yet! But just know that I understand that you are a grown man with your own personality and agency. I will never take away your dignity or self-respect." I felt a wave of relief, and I smiled at him. He said "Tell me son, what do you like best about the things we've done so far?"
I said, "Well, daddy, I love your big sexy body, I love having your cock in my mouth, I love the way you fucked me, basically everything! And I really love the way that you take charge and direct me! That, perhaps most of all. It was a strain having to pretend to be more masculine that I was when I was married. It was a big relief this weekend to get to let go and be submissive".
"Well, son, you've come to the right place I've got a whole lot of kinky surprises for you. C'mon we are going for a road trip" When we got in his truck he said, "Scooch over to the middle seat". Daddy turned his head and kissed me, right there in the diner parking lot! But I didn't care and kissed him back enthusiastically. He put my hand on his thigh and put his hand on mine as he backed out. We drove for over an hour, stopping at a rest stop so I could suck daddy's cock again, which I did with gusto.
He told me that it was important that I suck his cock several times a day; daddy had a lot of testosterone and needed to cum often. He said that I should consider these frequent blowjobs "maintenance suck offs". If my mouth or jaw got tired, daddy would jack off into my open mouth, and I could swallow the cum, but it was very important that daddy's cum end up in my stomach or ass, nowhere else.
I didn't ask where we were going but I noticed that we were headed south toward New York City. He drove into the city down to Greenwich Village. We parked in a garage just off Christopher Street and I was wondering where we were going. We walked to a store called "London" which it turns out was a primarily gay sex shop. As we walked in daddy took my hand. He greeted the sales clerk, asking if they sold underwear. The clerk looked at us with no special interest. Apparently we were the store's usual sort of customers. The clerk led us to the back of the store going past the DVDs, dildos, lubes, poppers, and other paraphernalia. Daddy paused at the butt-plugs, picking up a medium size stainless steel beauty with a fake glass gem on the bottom. The clerk led us to the "clothing" section, leaving us to browse, asking, "will you be needing anything else?"
"Yes", Daddy said, "a bottle of good quality anal lube, the kind that's edible."
"What size bottle?" the clerk asked.
"The biggest one you've got" Daddy replied.
The clerk left us to our shopping. After perusing the jocks, thongs, and other underwear, daddy selected a pair of baby-blue underwear for me with a wide elastic waist band. "You are a thirty-two waist, right son"? Daddy showed them to me and I blushed when I saw that they had a big round cut out in the back. They were "easy access" open assed briefs! He picked out three pairs.
Daddy asked the clerk "Is there a fitting room?"
The clerk said "yes, but underwear was not allowed to be tried on in the store, it was not allowed by city code, and underwear was not a returnable item; however, he said, there is a small private club above the store where you can try things on after purchase". Daddy bought the butt plug and one pair of briefs asking, "Can we leave the rest of our purchases here while we try on one pair?"
"Certainly" the clerk said. "The stairs are just past where the underwear was."
Daddy thanked the clerk and led me to the back of the store. Another clerk sat at a small desk at the top of the stairs. He welcomed us and said that there was a $25.00 cover charge per person, and briefly went over the rules of the club; entry was for adults 18 or over, no alcohol was allowed, no drugs, or heavy activity that would cause bleeding, beyond that we were free to do whatever we wanted to. There was a bowl of complementary condoms and lube packets on the desk. Daddy took a few of the lube packets wordlessly.
The club had a row of small "changing booths." Daddy led me to one, closed the curtain and had me strip and try on the briefs. They were a snug fit, apparently designed to be. My ass hung out lewdly. Daddy spun me around, checking the fit. "They look pretty nice son but I wonder how they look on me".
"What?" I was thinking, "he wants to try them on?", but then he lubed up his cock and speared me with it.
Leaving me impaled on his massive cock, he looked down saying "Yeah they fit me real nice too". He whispered to me, "I don't like to fuck in public, least of all in a dirty sex shop, but I don't want your ass to get to get lonely." then he pulled out of me, lubed up the plug and slid it up my ass. I had never worn a butt plug before, but after taking daddy's giant cock, the plug was a breeze. Daddy said" put your clothes back on". I bent to pick up my underwear, he said, "no, I'll take those, son". I blushed again and pulled my khaki pants over my assless undies and butt plug. Walking with the plug in my ass was an unusual feeling, and was so kinky that I sprouted an erection.
We went to the counter and Daddy said, "We'll take the other two pairs of briefs and the lube". The clerk asked daddy if he wanted our other purchases bagged as well, to which Daddy replied "that won't be necessary, he's wearing them". At which I blushed the shade of a tomato. The clerk said to Daddy, "If you guys are around later on tonight, the store is co-sponsoring a party at the Man Cave later tonight. It's twenty dollars at the door, a free buffet and $10.00 drinks. The party is a charity event for a homeless shelter."
"Thanks" Daddy said. "Where is the Man Cave?"
"It's just up the street two blocks up."
Daddy was intrigued. When we got outside, he said, "I know we didn't plan this son, but you want to check it out? It would mean that we'd have to stay the night. I could try to find us a hotel room and we could grab some dinner then hit that party".
With me wearing sexy underwear with a plug grinding my prostate, I said yes immediately. I'd do anything to keep this incredible sex-filled weekend going. Daddy got us a room and we had a nice dinner, with me in my open-assed "boy shorts" with the plug still firmly lodger in my ass under my khakis the whole time.
When we got to the club, the bouncer, a biker type dude with a leather vest and a handlebar mustache, took one look at daddy bear and his clean-cut preppy date, and said, "you're going to want to check out the basement level, I think that you'll like it". Daddy got us two beers and we headed down to the basement level. It turned out that this level was known as a bear and leather daddy hangout.
The bottom level had a counter that said "clothing check". It had a rows of lockers behind the counter and an attendant. The attendant explained that tonight was a "tighty whitey" event, underwear only. Guests would strip down to only socks and shoes and underwear. You checked your clothes, wallets, keys, etc. with the attendant, and he locked them up and gave you the key on a wrist band. If you wanted to have drinks you had to pay $50.00 for an open bar, as there was no way to secure your wallet in just your underwear. Daddy took out his credit card and paid for the open bar for both of us.
"In for a penny, in for a pound, right son? You still trust me?
"Yes Daddy."
"OK then, strip."
Daddy and I stripped down and there was no avoiding it - my ass was exposed and on top of that I had a glittery butt plug up my ass. The bar was fairly crowded, but we immediately drew attention; a big burly bear and his younger cub, but everything was cool aside from a few whistles and some obvious staring, but hey, who wouldn't stare.
Even though I felt safe with Daddy, this was my first public outing as my queer self, and I was still nervous and painfully self-aware. Daddy saw this and hugged me and walked me to the bar.
"Two double bourbon's please." Daddy gave me the shot and said "drink". I drank the shot in one gulp, scowling as it burned down my throat.
"Now drink your beer" he said. The drink had a sedating effect and I relaxed a bit. There were no seats but daddy and I found a spot near the corner. A friendly older guy, even older than Daddy, came over for a chat. He had a thick nipple ring through each nipple.
"Hi there, I'm Chet".
"I'm Glen", Daddy said, "and this is my date Drew".
"Nice to meet you. I must say Drew that you have a sweet little ass on you, with that pretty plug and all."
I blushed and said nothing.
"You guy's must be hear for the contest".
"What contest?", daddy asked.
"What?" Chet said. "I assumed that's why Drew was wearing the pretty panties. There's a contest tonight, "spank a boy for charity". Daddies and boys pair up, or in your case are already paired up. A bartender acts as the MC. There is a big chair with a big leather paddle next to it. Each boy is displayed and the MC exhorts the crowd to pledge money to see the boy paddled. The MC hands out pledge cards. The boy who raises the most money wins the contest. He actually just wins a sore ass, but it's all in good fun and it's for charity. You two should sign up."
Daddy looked at me "could be fun, right, Son?" "The thing is", Chet said, "if guys are going to lay out serious cash, they want to see a proper spanking, just so you know".
Had it been any other day, I'd have misgivings, but I was so stoked on sexual adrenaline over the past two days, that I said, "let's do it!"
We signed up for it, and Daddy and I both had to sign a legal waiver. We were last in line for the contest. When it was my turn, the MC brought me over to center stage, and a spotlight was shown on me.
"Well looky, looky, look at this cute boy with his pretty little ass hangin out. C'mon guys, who wants to see this boy paddled? It's for charity! C'mon don't be cheap!" The hat was passed around and I got over $700.00 in charity pledges.
The MC looked at Daddy and said, "you know what to do". Daddy said "OK but I stop when I think he's had enough."
"Agreed" said the MC.
Daddy threw me over his shoulder and carried me to the spanking chair. He laid me across his lap with a firm grip around my waist. He picked up the paddle. It was fearsome looking, wooden, with leather covering, like an elongated ping pong paddle. "Ready"?
"Yes Daddy." He commenced paddling. The first strike rang out with a loud crack. I gasped! I wasn't prepared! Daddy paddled me steadily with medium hard swats. My ass was on fire. My ass was completely exposed to the onslaught, crack, crack, crack, it went on and on.
Then a strange thing started to happen, the unbelievable pain all over my ass spread a tingly heat directly to my groin. I had a hard on! I was openly crying and squirming, involuntarily rubbing on daddy's lap.
The MC called out "Ok, daddy, he's almost there, let him have five more hard ones". Daddy obliged and I was yowling and thrashing. On the final blow I shot a massive load in my underwear and all over daddy's leg. The crowd roared with approval. The MC yelled out, "I think we have our winner!"
Daddy got up and picked me up in his arms and carried me out of there. He grabbed our clothes and got us both dressed, being careful getting my pants over my inflamed ass. He carried me outside and hailed a cab. When we got to the hotel, he carried me in and all the way to our room, laying me gently face down on the bed. He said, "I'll be right back son". He grabbed the ice bucket and went to get some ice. When he got back he took off my pants and underwear, and gently removed the butt plug. He leaned down and kissed each cheek of my bright red swollen ass. He then rubbed several ice cubes all over my ass. It felt so soothing. After a while I became sleepy. He said, "I'm sorry son, that went too far".
"No daddy, it's OK. It hurt but I liked it!"
Daddy looked at me for a long time. "I think I love you son." "I think I love you too, Daddy".
To be continued.......