*So this happened two nights ago and I attempted to do a short ‘update’ on what happens at the end, because it was new and exciting to me. But, in trying to properly set the stage and circumstance, I wound up taking nearly a day and half and writing way more than I intended, so hope you all enjoy!*
Last night I was at one of those parties where at some point you look around and think to yourself: “why the fuck am I here?”. I had been invited by a co-worker of mine (f) whose wealthy family was putting it on. She had been dreading going because she never gets on with her parent’s friends and wanted someone she could talk to. I didn’t really have anything else going so I thought at the very least it’d be free food and drinks and maybe even a chance at getting a fire lit between me and her (I have always fostered a bit of attraction for her). But 1 hour into the night – though me and her had been getting along nicely – we both quickly realized that were essentially set dressing to these other “higher end” guests.
My co-worker texted some of her friends who were in the area, and we were just about to bail and meet them at the bar, when I looked across the room and noticed a slightly stocky, blue eyed older gentleman that sparked a glimmer of recognition. As I was trying to place him, he looked over and caught my eye, and it struck me. He was an old friend and colleague of my dad’s. He started to make his way over and I groaned a bit, realizing our exit was about to be delayed by social obligation.
I told my co-worker she should sneak off now if she wanted to go and I’d catch up with her at the bar as soon as I pulled myself away, she agreed and disappeared into the crowd.
“Jack?” The man (was still trying to place his name) asked, extending his hand.
“Yeah!” I responded. “Henry, right?”
“Good memory” he said, smiling.
We chatted for a bit catching up on my family and the business (my dad had since retired, Henry was only in his early 50s and still working). When I was starting to search around for a natural exit point, I realized that Henry was looking at me with a greater intensity than the situation would warrant and it stirred up something deep inside me. The thing that had set Henry apart in my mind from all my dad’s other friends: he was gay. I remembered years ago I had jerked off thinking about him the night that I had found that out. It was a few months after I had allowed myself to fully internally identify as bi-sexual and he had given off that mature experienced “daddy” vibe I had been so exclusively crazy about that time.
I flushed a bit thinking about this and the energy in the conversation immediately shifted. He was looking at me like he had just confirmed some suspension he held and I was trying and failing to get the train back on the tracks. Though my confidence in my encounters with men has grown over the years, this connection back to my more confused and vulnerable years coupled with the fact that my dad still doesn’t know fully about my sexual lifestyle had me feeling like there was a massive spotlight on me and that Henry could read my thoughts.
He noticed and after one last highly sexually charged glance that told me my sudden shyness had only turned him on further, he broke his gaze and looked around the room casually, his energy completely reverting to “empty social cocktail” vibes. And for a while the conversation flowed easily again.
“God, these people really are a bore.” He said, not too quietly. “Not even sure what the hell I am doing here.”
I laughed. “Actually, I was thinking the same thing just before you came over here.”
“What made you stay?” He asked, looking at me. The sexual energy wasn’t at the forefront of his gaze, which was polite and relaxed, but I could feel it bubbling under the surface.. or was that just me?
“Eh, social obligation, I guess” I responded aloofly, feeling like my confidence was finally gaining some traction.
Henry laughed. “Good one. Well, I won’t hold you up any longer…” – my heart dropped a bit – “go enjoy the rest of your night, I’ll manage this crowd by myself.”
I hesitated. I could see that, despite his obvious desire to fuck my brains out, he wasn’t going to cross any boundaries without my invitation. I made a decision.
“Walk me out?” I asked.
He seemed pleasantly surprised and the positive energy had returned.”Gladly.” He stated
….. ….
“Where are you? You still coming to the bar?”
I glanced at the text from my co-worker from the passenger seat of Henry’s car. I responded that I was actually feeling tired and deciding to just head home for the night. My fingers were shaking slightly and I had to retype the message a couple of times.
I had just had my dad’s friend’s tongue down my throat and was still buzzing with lust and excitement.
As we walked away from the party, Henry had put his hand on my shoulder as a last-ditch confirmation of his suspicion of our mutual intention and I had turned to him and shyly confessed that I had jerked off thinking about him the last time we’d seen each other. He had pounced, grabbing my face and pulling me into a deep kiss where we stayed for what felt like 15 minutes but was probably only two. His hands exploring my body and gripping my ass while I held onto his neck and rubbed his dick hard through his pants. His salt and pepper stubble scratched my cheeks as we made out and it drove me wild.
Eventually stopping for air, I breathed. “Where are you staying tonight?” He didn’t need more than that, he led me to his car and we were off.
It was fortunate that his rental wasn’t far because as we pulled up, the thoughts had started creeping in about whether or not this was a terrible idea given his proximity to my family. However, something about pulling up the driveway and seeing the front door bathed in porch light reignited the flame and resigned me to my immediate destiny. I was going to get fucked behind that door.
We were barely inside when Henry pulled me in for another long kiss, kicking the door shut behind us. Lust flowed through me again as I pushed my hips into his inviting him to take control of my body. He led me into the living room and in front of the couch. He pushed me down to my knees. Staring down at me while he undid his belt.
I took off my blazer and was starting to undo my tie when he placed a hand under my chin and stopped me.
“Keep the rest on, you look sexy all dressed up. I want to watch my little fancy boy sucking my cock.”
“Yes sir.” I complied, cottoning on how he wanted to play.
“That’s a good boy.” He groaned.
Looking up at him pleadingly, I reached out tentatively, my movements conveying both my desire for his cock and asking for his permission to have it. He looked down at me smiling, showing his pleasure with my actions, but hiding any direction. He was like a proud dog owner looking at a puppy who was behaving properly. He was going to let me guess at his pleasure… Would he punish me if I guessed wrong?
I found out soon enough.
I pulled down his pants and pulled down his briefs while kissing his stomach, taking in the musk emanating from his crotch. I took in the sight of his cock. Protruding from a thick but managed pelt of salt and pepper pubes was a surprisingly spry looking 7″ cut man-sausage, already plump with excitement, but nowhere yet fully hard.My hand gripped the shaft, but when my lips moved to the tip of his cock, my mouth watering with anticipation, I felt his fingers grip my hair and pull me back firmly.
“No.” He growled. “Balls first… That’s ‘One'” he counted, holding up a finger.
My tongue and lips found his sack and I took his balls in my mouth and sucked gently, staring up at him from behind his growing cock.
“Thats good” he smiled, sighing deeply. “That’s just right, boy”
I racked up 4 more “penalties” as I pleasured him with my mouth. This game was driving me wild, full of an insatiable desire to please Henry while also brimming with anticipation as to what my punishments might be left me feeling in a disembodied limbo, completely subject to my sexual instincts and his corrections of my errors.
It made me hunger for him. Every time his tip past my lips and slid it’s way down my eager throat and I heard him moan with affirmation, I was filled with a deep sense of purpose and fulfillment. What better thing could there be than this? This beautiful cock brimming with breeding power gaining force from the sensation of my mouth.
I could taste the pre-cum on my lips and I could feel his hips begin to shudder and his balls begin to clench. He grabbed my hair for support and forced my head towards his crotch, fucking my face and moaning deeply. His knees gave a bit and he gave one great thrust upwards and I felt the first wave of hot cum hit the back of my throat. I sputtered and swallowed quickly as more kept cumming, filling my mouth to the point that his seed was dripping down my chin. He pulled back and I had to spit what was left as I was nearly chocking. He bent down and kissed me hard and together we lapped up and swallowed the cum I had missed.
Henry stood up and breathed deep. Satisfied. He kicked off his shoes and pants and walked into the kitchen, wearing only his open dress shirt. My eyes found the tip of his still-dripping cock swaying confidently behind his firm ass cheeks as he walked away.
I was still kneeling when he came back, feeling extremely punch drunk from my exhibition of cum-sluttery. I felt rooted to the spot, like if I moved the satisfaction I currently felt ebbing through my body would fade away. I looked up and Henry was holding out a glass of water, surveying me.
“Drink.” He said.
I took one shaky sip of water, but after the first taste, found I was much more thirsty than I had realized and soon I was taking big gulps in between heavy breaths. Once I was done, I handed him back the mostly empty glass.
He placed the glass on an end table and then brought me off my feet, guiding me around the room. Facing me away from him, he pushed me firmly so I was bent over the back of the couch, pulled my pants down and spread my legs apart, taking in the sight of my pale ass. He grabbed my tie like a leash and guided my neck back.
“How many did we get up to?” He asked. “Five?”
“Yes, sir.” I responded, thinking I knew what was coming next.
I was right.I barely had time to prepare when I felt a hard smack on my ass, sending a shock through my body and a firey tingling in the spot where his hand had met my flesh. I yelped.
“You like being punished boy?” He growled.
“Yes, sir.” I answered. “Give me another”
I wasn’t just playacting. Once the shock had resided, the warm spot on my ass had become a beacon of dirty satisfaction, ebbing through my body that was now just begging to be used.He went through a progression of firmness to his spanks. Each one making me yelp louder and louder until a guttural groan of longing pervaded each outcry. Henry could see this reaction in my body and wound up going well above the ‘five’ I had earned, each strike fueling my lust further and further. When he was done, my ass was raw and burning. Then I felt his face tenderly nestle between his cheeks and his warm, wet, firm tongue flick out and brush my hole. And fireworks ignited in my head.
I let out a deep moan and pushed my hips back into his face, the warm pleasure coursing throughout my body as the roughness of his face on my tender cheeks blended with soft slippery deftness of his tongue on my sphincter. From my waist to my knees, everything just seemed to melt and flex as he worked my hole. I arched my back and pushed into him, wanting that feeling deeper and deeper inside of me.
My breath quickened and I was looking without seeing, all of my consciousness focused on the feeling of his tongue on my asshole. This old friend of my dad’s turning me to putty in his hands. With that thought, I felt his fingers enter me.
I wasn’t expecting it, but his spit and firm tongue had loosened and lubed my asshole and I sighed deeply as his finger entered me up to the knuckle, his adjacent fingers cupping and supporting my ass. He moved to my side and reached below my torso with his other hand and took my cock in his hands. It was only then that I really took stock of what a raging hard-on I had. My mind had been completely focused elsewhere and – at his touch- I realized how close I was to bursting.
He didn’t fuck me with his finger, but stayed knuckle deep and guided my hips like a puppeteer, using my body to fuck his own hand. Meanwhile, my head was spinning; my body trying to fuck in two directions, pulsing between trying to take his finger deeper and more firmly into my ass and trying to pump my cock through his hands. I could feel the orgasm building inside of me and my pumping rhythm started to get fiercer and more determined, and just as quickly had it started, the fuel driving the engine had sputtered and died.
I was panting, wondering what happened. Where had that finger that had been filling and controlling me so completely and the strong hand around my cock gone? Then I heard Henry’s gruff voice in my ear.
“You’re not going to cum all over the back of my couch.” He said.
I felt spent, cheated and depleted. Fuck this control game, I had been so goddamn close, its not even his couch! But, more than anything – and i’m sure Henry had been counting on it – the desire to get back to that place was stronger than ever. In that moment, I would have done anything to regain that pleasure that had been coursing through my body moments before.
“Follow me.” He stated. And I obliged. Barely even noticing I was still wearing my ruffled dress shirt, loosened tie or black socks, let alone having the where-with-all to remove them.
We walked down the hall and he opened a door at the end of it, revealing a small home theater with a wrap-around couch and a big square, padded ottoman in the middle.
“I was hoping I’d get a chance to use this room while I was here.” He breathed in my ear as I passed him into the room. “I was poking around and found some stuff we might have some fun with. Settle in and I’ll be right back.”
I dimmed the lights to “movie mode” and lay down on the couch, wondering what he might have found that he’d wanted to have fun with. I could see the obvious appeal of the ottoman, it was plush and padded and could easily fit two grown men fucking. Porn maybe? I doubted any AirBnB host would leave sex toys laying around…
The door opened and Henry walked in fully naked, holding a bottle that looked like lube (yes!), some condoms, and… a Sony camera and some cords.Looking at the big screen I realized what Henry had in mind.After fiddling with some cords and some inputs and adjusting the angle. Soon we had a live feed of the room displayed on the TV in front of us.
Though it had taken a couple minutes and my buzz had definitely subsided, the anticipation of what was coming definitely kept the fire raging. Especially when I saw the view angle of the camera. I had fucked in front of a mirror before, but this top-down angle had a dirty, voyeuristic quality that no mirror could match.
When Henry turned around and looked at me, that hungry fire returned to his eyes, I knew he was ready to go again. His gaze made me self-conscious in a good way. I looked to the screen and saw myself from the angle behind his head. A sexy, pale little half dressed morsel on his back with his knees up and spread, unconsciously running his finger around his sensitive asshole. Shit, I would fuck that. This objectification of myself only increased my horniness. I was seeing my body as a sexual being, ready to serve its purpose.
He told me to lie on the ottoman and keep doing what I was doing. I got up and lay back down on the padded surface, from this angle, I couldn’t see the screen, just Henry bathed in the light from the TV and the dark sound-proofed walls behind him.”Just.” I stammered, worried if this would break the spell.
“Please don’t record… if my dad..” I trailed off.
“Did you just tell me what not to do?” He barked, giving my thigh a smack. Then he smiled, playfully. “No, Jack, don’t worry. I wouldn’t want that out there either. This is just for us, for right now. Now, loosen that asshole for me.”
I complied. Pulling my feet up and bending my knees so that he had a full view of my hole, I begin to let my fingers wander around my ass. Spreading my cheeks with my thumb and outer fingers, while brushing and teasing my hole with the middle ones. I watched him between my knees, slowly stroking his cock hard while his gaze jumped between the sight before him and the picture on screen.
He then moved back, fading into the background. Wondering what he was doing, I arched my neck back a bit and chanced a glance at the TV and saw that he had moved out of picture and the screen just showed me in my shirt and tie and dress socks, pleasuring myself in the semi-darkness. I looked over and Henry was jerking off, transfixed on the screen. He obviously saw me looking around and flashed a look that told me he wanted me to act as if he wasn’t there. So I played the part, feeling sexier than ever as my hips started to grind and my fingers started to push in and out of my hole.
I actually started to believe the act as I explored my ass. Staring at the dark ceiling, picturing myself alone and just enjoying my own body. But the ever present knowledge that I was being watched was what really fueled me. Knowing that Henry was in the corner, arousing himself to the voyeuristic image on screen drove me wild.
And then he was there, one hand running down my inner thigh and the other holding the bottle of lube. When his hand reached my ass, he poured the lube from the tip of my cock and let it drip down my shaft and pool in his hand at my hole. He ran the cool velvety liquid all over my crack and I felt my asshole pulse when he brushed by.
“Get on your knees.” He commanded. And I flipped over eagerly, anxious to be in a position to watch. He laughed. “You like this, don’t you?”
“All due respect, sir.” I breathed, nearly exhausted with build up and anticipation “But will you just fuck me already?”
He grabbed my hair and pulled me back lightly but firmly and whispered in my ear. “You better hope you don’t regret that, boy.”
And then he was inside me.
I gasped and my whole body tensed and lurched forward from the intrusion. The shock to my system was short and intense. My asshole was firmly protesting while something deep inside me was begging for more. My eyes caught the screen and I saw myself on my hands and knees and Henry’s body fully up against mine, his dick in fully up to the hilt. I was feeling that cock pulse inside me, staying deep and experiencing its home flexing and loosening to accommodate him.
And then he began to pump. I put all my concentration into loosening my hole further, to relax and remove that slight tense burning from the otherwise waves of ecstasy that were flooding my veins. In that moment, I put my head down and closed my eyes in concentration when I felt a tug in my hair pulling my head up and directing it to the screen again. Henry wanted to me watch. The image of him fucking me drove all consideration of my tender ass from my mind. Suddenly it didn’t matter. I saw all the things on the screen that I hadn’t even realized I had been doing. How my back was arched and how my hips kept pushing back unconsciously to receive his thrusts. And Henry. The way I saw him looking down at my back from above, his head locked in concentration on my body, made me think of how he was picturing his dick filling me. This hot older man trying to pump his seed into the more-than-willing recipient before him.
The orgasm was building in me again and wild instinct burst into flame as I began to work my ass furiously and hungrily. With my hole now filled with cock-milking fury, it became evident from the picture on screen that Henry wasn’t going to last long either. He was screwing his eyes up in concentration, trying to hold out to the absolute last possible moment. Seeing that sent me over the edge. The need to drain his cock into me was so primal that it consumed every particle of my being. And once again, my body’s instincts led the way. It knew the final piece that was needed.
As wave upon wave of life-affirming orgasm flooded from my hips out to my clenched fists, my asshole clenched and pulsed around his throbbing cock and he let out a loud “oh Shit!” and thrust more firmly and deeply than ever before. I felt his hips shuddering against my cheeks and his cock expanding and draining inside of me, burst after burst of warm cum filling me. My climax ebbed and flowed like the surf, tingling pleasure pushing forward, replaced by peace and fulfillment as it withdrew. I could feel Henry behind me going through something similar, pushing his cock slightly more in me with every new wave of satisfaction. And then he was out and I collapsed onto the ottoman, looking up at the sloppy mess of myself on the screen and feeling simultaneously more dirty and satisfied than I think I ever had before
…… …..
In post-nut clarity, I realized one detail that I hadn’t even considered up until this point.
“You didn’t wear one of those condoms?” I asked, my tone somewhere between exasperation and accusation. The time for calling him ‘sir’ was long gone. This asshole just fucked me raw without permission.
His face spelled genuine surprise and immediate guilt.
“Shit Jack, I’m sorry.” The act was dropped. “I honestly forgot, my ex and I never used them. I’m tested and clean and everything, I swear.”
I had used that excuse myself before and had felt like shit about it after. But the fact he had dropped the control act and seemed fully remorseful made me soften and suddenly realize I didn’t care so much. If he had asked in the moment, I would’ve wanted him raw. If he was a complete stranger, I would’ve been more cautious and careful during the act and more angry after, but his connection to my past and general familiarity with my family had made the whole thing easier while retaining a taste of the forbidden. My dad had always called him a “stand-up guy”, responsible, someone who could be counted on. His controlling forward attitude and the potential consequences he represented made him feel dangerous, but our connections and familiarity made him also feel safe. That mixture had made me forget the condoms too.
“Don’t worry about it.” I said. Feeling the cum dripping from my asshole. “I was just thinking that next time, I would’ve insisted on it.”
He raised his eyebrows. “Next time?”
“Yeah, Im staying the night, right?”
He smiled.
Source: reddit.com/r/gonewildstories/comments/p1d0ra/so_i_fucked_my_dads_friend_this_weekend_mm
This is amazing