Going Gay with a Family Friend

Back when I was a teenager, my dad was suddenly fired from his job and was lucky enough to quickly find another one before any financial hardships were felt. He worked for some sort of corporation, not sure exactly what he did, but he ended up becoming really good friends with his supervisor. His supervisor's name was Jeff Williams, who became a close friend of the family, always coming over to eat dinner, or go on a fishing trip with me and my dad, and other things. He was a really nice guy and successful too.

It was never a problem that he was my dad's supervisor because he handled it really well and was never a jerk. He was a really good looking guy too...same age as my dad, in his early forties, dark shorter curly hair, trimmed mustache, tall (probably about 6'2"), olive skin, and seemed pretty well built. We always cut up and joked around and just got along really well. Eventually I went off to college, and decided to come back home during the summer. Jeff eventually came by to hang out with my dad, and hadn't known I would be coming to stay. He knocked on the door and I answered it.

Jeff: "Whoa, hey Tony! I didn't know you were home"

Me: "Hey Jeff, yeah I decided to come back home and stay with my parents for the summer."

Jeff: "Well good deal. Good to see you. It looks like the swim scholarship is treating you nicely. You're looking really trim and fit."

Me: "Thanks, yeah I'm not missing having to practice so much."

Jeff: "Well good. Just have fun and relax...that's my motto."

Me: "Sounds like a plan" (smiling)

Jeff: "Is your dad home?"

Me: "He will be in about half an hour"

Jeff: "I see...you want to shoot some hoops until then?"

Me: "Sure, even though you're about half a foot taller." (laughing)

Jeff: "I'll go easy on you" (smiling)

I change into a tank top and shorts and grab the basketball. It's decided we're going to play just some regular one-on-one. I start dribbling the ball and turn my back to him to protect the ball. He comes up to guard me, swatting at the ball. "Don't even think about stealing the ball, Jeff. I've got skills. Haha," I say. He responds, "You're not even going to get to the basket with me guarding you." He comes in further and really guards me closely. I can feel his crotch slightly rub against my ass. I keep dribbling and it seems as if he's still guarding even closer. I can feel his soft cock pressing against me. Finally, I dribble pass and shoot it up and score. "Make it, take it, right?" I ask. "Sure, why not?" he answers. I take the ball back out and bring it in again. He resumes his hovering position on my backside. I break away and shoot up, but it hits the rim and bounces away.

Being taller, Jeff snags the rebound and takes it back out. He dribbles in and turns away from me to protect the ball. I notice his legs are pretty far apart so I try to slap the ball away by going between his legs. I reach through and as I do, he moves slightly and my hand accidentally rubs against his dick, but I do manage to knock the ball away. "Hey now, that's not fair, you were distracting me," he says. "It was an accident; I was going for the other ball, not yours. Haha." He says, "It's still distracting and it's still my ball." We continue playing and finish the game as my dad pulls in the driveway. "Good game, Tony", Jeff says, slapping me playfully on the butt. "Yeah I'll beat you next time." Jeff walks over and chats with my dad and I go inside. As I'm changing, I start thinking about how I brushed Jeff's dick. Man, it was pretty large for being soft. I wonder how big it is hard? Then, I'm thinking why am I wondering about Jeff's cock? He is an attractive guy but I've never been one to be attracted to guys. I pushed the thought out of my mind and finished showering and changing.

A few days later, I walked down from a fresh shower and put on a cut-off t-shirt and some cargo shorts over my baby blue boxer briefs. My dad was stressing out over a bunch of paperwork at the kitchen table. "Hey Tony, can you do me a favor? I need you to drive over to Jeff's house and pick up some files I need to finish later on. Can you do that for me?"

"Yeah sure Dad. No problem. Just give me directions because I haven't been to his new house."

"Great, thanks son, I'll let him know you're coming." I get directions and hop in my car and drive over to Jeff's house. As I pull up in his driveway, I let out a slow whistle. "Wow! Now this is a house." It's a large two-story mansion-esque type house....very expensive looking. I get out of the car and walk up the sidewalk to the front door. I ring the doorbell and hear the echoes of the ring throughout the house. I can see a large silhouette of a man walking up through the glass of the door. The door opens and Jeff is standing there. "Hey Tony, come on in." I walk in and scan the inside of the house, looking around. The interior is large and spacious with vaulted ceilings. "Well, what do you think of my new house?" Jeff asks. "It's awesome man. I didn't know you did this well at work."

"I do ok," he responds, smiling, "follow me". I follow him and notice he has on a tank top, somewhat short shorts, and wet dark hair so he must have just gotten out of the shower. He motions to a room, "There's the den...have a seat and I'll grab those files for your dad."

I walk in and look around. The room is basically a TV viewing room, designed for relaxing. There's a leather wrap around couch, a fireplace, a large 60" flat panel TV on the wall, speakers everywhere, and not too much lighting. I also notice a small cabinet close to where the TV is and walk over to check it out. I open it up and notice just a bunch of blank VHS tapes. Looking through some of them, I notice none of them have labels. "Odd..." I thought. "I see you found my movie gallery" I hear from behind me. I look around and Jeff had just walked into the room.

Me: "Sorry, Jeff, I was just being nosy. Why don't any of these tapes have labels?"

Jeff: "Because this is my porn collection. I have them on unlabeled tapes so when I grab one to watch, it'll be a surprise."

Me: "Good idea. It must be nice to have such a large collection. I think I might maybe have one."

Jeff: "Well I have plenty there. You're more than welcome to borrow some and make copies."

Me: "Yeah but I won't know what's on them."

Jeff: "Well, pop some in and preview them. I'll watch with you to give you my opinion."

Me: "Ok sure why not."

I grab one and pop it in and hit play. Jeff lowers the lights some to enhance the viewing experience. The first one opens up to a hot brunette swallowing a huge cock while the guy eats her out. "Damn, I didn't realize how long it's been since I've gotten laid," says Jeff, "Look how gorgeous her tits are and how she's sucking the load right out of that cock. That's hot." The couple starts fucking and the stud switches from pounding her pussy to pounding her ass. "Man that has to be hurting her," I remark, "especially as big as that dude's dick is."

"No not really. If you do it right it can be really pleasurable for the person getting fucked...and man there's nothing like fucking a tight ass" Jeff comments. I look over and notice a sizeable tent in Jeff's shorts. "That's it for this tape. Try another" he tells me. I grab another and start it playing. This time it's a blonde with huge tits and a nice round ass. In walks two studs, and she drops to her knees and begins blowing both of their swollen tools.

"Damn those guys are lucky...I could really use a good blowjob," Jeff says. I look over again and notice the head of his cock is poking out the leg of his shorts now, and man is that thing huge! I look back at the screen and now she's sucking one and getting fucked by the other. Jeff looks over and says, "Are you straining as much as I am? I've got to let this thing free." He pulls down his shorts, and reveals he wasn't wearing any underwear and his cock is sticking straight up, swollen and hard, stretching to about 9.5 inches and really thick. "Do you mind?" he asks. "No man that's not a bad idea." I pull my shorts and underwear off and my rock hard cock points straight at me, growing to its full 8 inches. "Cool," Jeff says. He starts stroking and his cock seems to grow even more. I stroke mine too watching the two guys blow their loads all over the blonde's face.

"This one's done. I'll put in another," says Jeff. He grabs a tape from the back and pops it in. He pulls his shirt off as he comes back to the couch, making him fully naked. I decide to follow suit and pull my shirt off. I notice he has a nice covering of curly hair across his chair and stomach, his bush is trimmed, and his balls and cock are smooth and shaven, while I am completely smooth all over. The tape starts up and the setting is a weight room. Two guys walk in and start lifting weights. I wait for the girl to pop in, but she never does. The guys are working out and it keeps showing close-ups of their hard-ons in their shorts. Eventually one guy pulls the other guy's shorts down and starts giving him a blowjob.

"You ever watch a porn like this, Tony?" Jeff asks.

"No," I respond.

"You know the best blowjob I ever got was from a guy," Jeff tells me.

"Really?" I say.

"Yeah, actually the best blowjob and ass fucking," he says.

On screen, the guy that was sucking cock is now sitting down on it.

"You know I think you're really hot, Tony. You've got a great body and are sexy as hell."

"I think you're attractive too, Jeff."

"You know when I watch these movies, I wish it was you and me doing all these things," Jeff reveals. "Really?" is the only response I have at this point, amazed at what's going on. "Yeah, I imagine your cute little mouth on my cock and then fucking that tight little ass of yours. I've wanted to do you for a long time." I look over at him; he's staring at me stroking his long swollen rod. "You want to come over here and relax and just have some fun?"

I don't even say anything; I stand up and walk over to him and sit right beside him. He puts my hand on his cock. I wrap a hand partly around it and begin to stroke it. "Yeahhhhhh...." he mutters. I move down to my knees between his legs. I lean down and kiss his balls as I continue stroking him. I kiss up his shaft and all round his head. Then I take my hands off and very lightly and slowly run the tip of my tongue down his shaft and around his balls, so lightly he can only feel the tingle from the sensation. I can see his eyes close and squeeze together. I gently blow a small stream of air over his hot pulsing tool. "Fuck..." he groans. I wrap both hands around the base of his cock and stand it up, just licking the pre-cum out of the top. I open my mouth, sticking his head, and then wrapping my soft lips around it tightly and suck and lick his mushroom cap. I double-fist his shaft and stroke it slowly as I wildly tongue the top end of his cock. "Damn...you're hot Tony." I move my hands lower and open my mouth and throat and take as much of his cock down as I can and am able get a good 8 inches in. I pull it out and push it back in. My fingers are running around his big smooth balls as my mouth sucks down his large piece of meat. "This is the best blowjob I've ever had" says Jeff. He puts his hand on the back of my head, gently pushing my mouth on his cock. I get hotter and hotter and keep sucking harder and more wildly.

Jeff pulls my head off his cock and stands up. Now that I am eye-level with his dick, he puts his cockhead back at my mouth and pushes his cock in. With his hand on my head, he starts to face fuck me while I make my lips nice and tight. He pushes harder and harder until he is completely down my throat. I'm trying not to gag as his meat pushes further down my throat. I can also feel his balls hitting my chin. My mouth stretched to capacity to accommodate this huge sausage. He pulls out and rubs his cock all over my face, slapping it against my lips. He pulls my jaw apart and his dick goes back to filling my mouth. He pumps some more and then pulls out again and lies down on the floor. He says, "Come here and get on top of me...I want your face at my cock and your ass at my face." I comply and climb on top of him. I position my ass down by his face and can feel his hands grabbing and squeezing my cheeks. I lean down and resume sucking on his mancock. I feel my cheeks being spread and his tongue entering, flicking my tightened hole. The sensation was more pleasurable than I had expected. It made my cock harden even more and made me want to suck his cock faster and harder. He ran his tongue up and down my crack, making sure to pay special attention to that little opening. He pushed his tongue in and started tongue fucking my ass. I was going nuts from this. I pushed harder down on his cock forcing it in more and deep-throating his huge tool. I could feel him lifting his hips to push his cock into my mouth. I pushed my ass down more on his face to get more of his tongue in me. I felt him bury his face in my ass, shaking it, and tonguing it crazily. I pull his cock out and yell, "Fuck Jeff!"

He pulls his tongue out and sticks a finger in; I get lost in a trance of lust. He barely squeezes another finger in. "Damn you're ass is so damn tight!" he says. He fingers me some more and then pulls them out. "Tony, will you sit on my cock, please? I've wanted to fuck your ass for so long." I turn around and crouch with my ass inches above his cock. I stand up his rod and he puts his hands at the bottom of my ass, spreading my cheeks. I rub his head against my hole, turning me on. I slowly lower myself on to him, feeling like I'm being impaled. I keep going until I'm sitting completely on his cock. I've never felt anything like this; His cock is so deep inside me and I am furiously turned on. I put my hands on his chest and kind of lean forward. I start fucking his cock with my ass. "Fuck! I knew your ass would be tight but damn!" His large, strong hands squeezing my ass cheeks as my tight hole envelopes his meat. He flips me over and holds my legs up towards my head and fucks me with his massive tool. Both of us watching him pump me. I pull my legs further back and stand my ass up. He stands up, holding my ankles, and lowers his cock in and out of me. I feel empty every time he pulls out.

He stops and sits up on the couch; I follow and straddle him and begin riding him again. His strong arms pulling me close...my ass cheeks stretched from his hands. "You're going to make me cum soon, Tony." I lean in and start kissing his neck. "Go ahead and shoot it in my ass. I want to feel it."

"Fuuucccckkkinnngg hotttttttt....," he moans, "here it comes...." I bounce harder on his cock, my arms around his neck, our chests close together. "Ohhhhhhhhhhh...take it baby." I feel a warm sensation in my stomach as his cock pumps an enormous load of cum in me. I make sure to keep fucking his cock, "I want it all...I want all your juice from your hot mancock." He continues shootin and finally collapses. I leave his cock in my ass and lean against him. "That was awesome, Tony," Jeff says. "Yeah, Jeff it was. You mind if I just stay here tonight?" I ask, smiling. "You can stay as much as you want with an ass like that," Jeff answers, grinning.

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written by bicuriousnfl2443