Date: Fri, 13 May 2022 23:42:04 +0200 (CEST) From: lucas_dwyer@tutanota.com Subject: A Father's Perdition part 8 (gay>incest) This story is completely fictional any references to names, places, situations are made up. If you enjoy the stories posted here please support Nifty. http://donate.nifty.org/donate.html ------------------------ Feel free to contact with comments and suggestions. I enjoy hearing what everyone thinks. Email: lucas_dwyer@tutanota.com If you would like updates on when I plan to post new chapters feel free to follow on twitter. Twitter: lucasstories ------------------------ Author Note: A short chapter that will build up to what I have planned next. Hope everyone enjoys and thanks for the positive feedback! ------------------------ I have an idea of what Dan wants to do to get Oliver ready so I ask what he has in mind. He stands saying he'll be back in a minute then disappears down the hallway. I look at Eric but he shrugs having no idea what's about to happen. When he comes back in the room he's carrying a small duffel bag that he sets down on the coffee table before unzipping it. He rummages through it before saying "here we go." He pulls out a plastic encased set of buttplugs ranging from small to medium then opens the package and places them on the table one at a time. He sets out a total of three, the largest being one I could easily take but these aren't for me, they're for Oliver. "I bought these before you came out, I wanted to find the right time to bring them out and talk about them so what better time than now" he says. He must see the uncertainty I'm feeling now faced with this decision because he says "you're his father Henry so I'm not going to pressure you but we both know you want this and I'm certain Ollie wants it too he's just too young to understand what he should be asking for." I know he's right, fuck I'm ready for this but it's also terrifying at the same time. "So when should we start" I ask. Dan looks at me and says matter of factly "right fucking now son." I stand up raising my hands to shut him down but he stands too saying "listen Henry, the boy had a big day, he's tired and will sleep through the night" he picks up the smallest plug and says "it might be hard on him getting this first one in but if he can keep it in all night he'll be well on his way to taking the larger ones." I shake my head but then Eric chimes in "maybe we drug him?" I spin my head towards him "what the fuck Eric!" Dan says "hear him out Hen, it'd definitely be easier on him." "Okay you both have lost your fucking minds..." I shout "you're saying you want to drug my son." Dan grabs me by the shoulders holding me still and facing him "that's not what we're saying son, but there's ways to make it less painful for him while he still is aware of what's happening" he pauses then says "I have something that I used with Kyle his first time and it worked really well." "Alright so what do you have that we can use" I ask with a hint of snark. He grins, pleased that I'm giving in, he walks back down the hallway to the bathroom then back with a tube that looks like a lube bottle. "Like I said, used this on Kyle and he barely felt anything... but I also went pretty easy on him too." I look at him shocked and say "uhhh wow where was this bottle of..." I grab it from him looking at the label then continue "anal-eze and where was this concern for my comfort when you fucked me that first time." He looks genuinely hurt so I quickly apologize for being an ass. I look at the tube reading the instructions then walk into the kitchen setting it down on the island turning and opening the pantry. I dig around until I find what I'm looking for, pulling out a bottle from Dan's prized whiskey collection I set it on the island then go retrieve a shot glass. I look at Dan and Eric then ask "either of you want a shot?" They both shake their heads so I pour myself one, slam it back, pour another and slam that one back. Dan says "whoa son, take it easy" but I'm done, that should be enough so I put the cap back on then place the bottle back into the pantry. I grab the tube and make my way down the hallway to the bedroom where Oliver is sleeping. I push the door open and as the light from the hallway shines in I can see he is sound asleep and looks so peaceful yet here I am ready to ruin that. I walk over to the side of the bed and kneel down, setting the tube on the night stand. I place my hand on my sons back gently rubbing him until he begins to stir. His eyes flutter a bit, then he sees me and as tries to focus he says "daddy?" "Hey sweetie, I'm sorry to wake you" I say softly while rubbing his back. "Is everything okay" he croaks, his voice a little hoarse from being woken up. "Daddy, grampa and Eric want to do something else with you but you'll need to be awake..." I say at which point I see him get a curious look about him as he props himself up. "Are we going to play again" he asks. "No sweetie, we want to do something that will help you get ready for some of the playtime we have planned" I gently run my fingers through his golden hair feeling how soft it is, admiring how well it frames his face. I continue "but this can hurt a lot so we need to use something to make it so you won't feel the pain." I can see he's more concerned than curious now so Dan steps in "remember how brave you were earlier and how much fun we had" he says to which Oliver nods his head "well we need you to be even more brave but remember what I said," Oliver chimes in with a smile "you love me and won't hurt me." He steps closer saying "wow you're such a smart little man." I stroke his cheek and say "he's daddy's brave little man isn't he" which gets a huge smile from him. Eric disappears as Dan walks to then other side of the bed sitting on the edge. Oliver is still undressed but under the covers so I pull them back to the foot of the bed so he's fully exposed now. I look to Dan unsure what to do next so he tells Oliver to roll on his tummy get into a position where his legs are pulled to his chest. Oliver does as he's told and in a matter of seconds his ass cheeks are spread wide and his hole in plain view. Dan can sense my apprehension so he says, "why don't you sit at the head of the bed and talk to him, I'll get him ready ok." At this point Eric walks back in the room holding the smaller plug and a bottle of lube. As I hand over the bottle of anal-eze I feel a tear roll down my cheek. Eric places the plug and lube in front of Dan then walks over with his hand out. I take it and he pulls me to my feet walking me closer to the door. Dan tells Oliver to stay put then gets off the bed and comes over to us asking "what's wrong son" the concern evident in his voice. I look at Oliver then back to him and before I can say anything he reassures me he will be gentle. I shake my head and say "no dad that's not it, I know you will be..." I turn facing Oliver again, laying there with his butt thrust up in the air, docile, waiting for whatever we plan on doing. I turn toward Dan and Eric again and say "this is the last time he'll be my little boy, after we do this he'll never be the same again." Another tear streams down my cheek which Eric quickly wipes as Dan grips my hands in his, I can tell he's getting frustrated with me but also trying to be calm and reassuring as he says "it's scary son, I get that" he pauses, looking back at Oliver then to me again and for a moment I see uncertainty which he immediately shakes off "he'll always be your little boy and nothing will change that but your relationship with him is about to get so much stronger so look forward to that, okay?" I nod my head in agreement, Oliver will continue growing and he'll learn things with or without our guidance so I would rather he learn from his family. We walk back to the bed, Oliver turns his head looking back at us and asks "are you okay daddy?" Dan places his hand on my shoulder and says "you should sit with him during this, he needs you." I move next to my son sitting on the bed then tell him "daddy's fine, I'm just worried about you that's all." He looks up at me and smiles "it's okay daddy, I'm not scared." I ruffle his hair saying "I know, you're my brave little man." His smile widens as I position myself on the bed so he's between my legs and I can hold him if he needs me to. Dan kneels behind Oliver, Eric takes a place next to him handing the man the tube. Dan squeezes out an ample amount of the cream onto his fingers then has Eric spread Oliver's ass open. As he begins to apply the cream Oliver tenses so I begin to gently rub his shoulders and upper back soothing him. "Alright Ollie" Dan says "I'm going to push a finger into your butt to spread some of this cream around." My son looks up at me, his eyes wide, he asks "he's gonna put a finger in me?" I try to give a reassuring smile as I tell him "that's right, he's going to spread some cream around that will help your butt so it doesn't hurt when he..." I pause for a moment not sure how to explain what he's going to do. While I'm thinking Dan pipes up and says "flip the boy on his back and hold his legs up." I look at him questioning but he just grabs Oliver's waist and tells him to turn over. Once he's on his back Dan grabs the boys ankles thrusting his legs up he tells me to hold them. Once he's in position Dan holds up the butt plug so Oliver can see it telling him "once your butt is numb I'm going to put this inside you." I feel my boy begin to shake a bit so I hook his legs with one arm and use my free hand to rub his chest telling him "it'll be ok baby." "Listen Ollie" Dan says "if you want to play with your daddy, uncle and grampa this will make it easier for you okay?" He nods his head slowly as Dan places the plug back down on the bed then begins pressing his index finger at my son's virgin hole. Eric moves closer to me taking Oliver's legs and holding them in position so I can focus on comforting the boy should he feel any pain or get scared. Oliver winces as Dan's finger pierces his hole, "does that hurt baby" I ask concerned. He shakes his head and responds "just feels weird" so Dan continues saying "must be working already." He pushes a little deeper, this causes Oliver to squirm a bit but he's up to his second knuckle and the boy isn't complaining although I'm sure the desensitizing cream is helping too. In a swift motion though Dan pushes the rest into my son's rectum groaning as he does. He's moving his finger around which causes Oliver to squirm more but again he doesn't complain. I stroke his hair talking to him, telling him how good he's doing especially now when Dan removes his finger and picks up the butt plug. He begins to lube it up, getting it slick before telling me "lift his head up, I want him to watch this." He's fucking ruthless, I think to myself but do as he asks lifting Oliver's head so he can see the plug. Dan looks at him and says "you'll probably feel some pressure when I start to put this in, there may even be a little pain but we're not stopping" he looks to the boy for acknowledgment, when he nods his head he continues "your daddy and uncle Eric are right there for you but I know you're a strong boy and you'll do really well." I can see the apprehension in Oliver's eyes as he looks up to me then Eric then back to me, I gently massage his chest telling him it will be alright. He turns his attention back to Dan who is beginning to press the head of the plug at his tight little ring. As he pushes forward, opening Oliver's hole up the boy begins to wriggle between my legs and lets out a soft groan. Before I can ask he looks up at me and says "it feels weird daddy." Dan is methodical though not letting up pressure while inserting the plug at a slower pace than I ever imagined he would. "You're doing great Ollie" Eric says, his view better than mine or my sons of how deep the plug is now. Dan stops for a moment and asks "how are you doing" to which Oliver gives a weak smile and says "it just feels funny grampa." The cream must be working wonders because Oliver doesn't appear to be in any pain, maybe a little discomfort but he's not begging us to stop so Dan proceeds by applying more pressure. Eric looks at me then leans close and whispers in my ear "bro it's almost all the way inside him" and just as he finishes I hear a soft pop and feel Oliver tense up. "Alright kiddo, you got your first plug up your cute little butt" Dan says cheerfully. Oliver's body has calmed a bit so he looks at me and asks "how long do we keep it there daddy?" I look at Dan questioning so he responds "well I think it's best to have you sleep with it tonight that way we can start working on the next one tomorrow." My son looks at me, a surprised look on his face he asks more rhetorically "all night?" I nod my head and tell him "why don't I sleep in here with you tonight" but Dan begins shaking his head then says "nah I think he should sleep in grampa's bed tonight that way if he has any difficulty I can help him with it." His grin though tells me he's up to something or he's more worried that at some point Oliver will start complaining and I'll just remove it so he's making a move to prevent that. It's way past Oliver's bedtime and I know I'm beat and Eric looks like he's ready to pass out so Dan says "Ollie, why don't you go in my room and get in bed then I'll be in shortly." When Oliver stands he bounces from between his feet, the feeling of the plug sticking out of his butt making it awkward to move around with; again I notice he doesn't seem to be in any pain but more likely a little discomfort. He grabs his blankie then walks out of the room, once he's gone Dan turns to me and says "so tomorrow morning I will remove the plug, I think the three of us could have a little fun with him before we start working on the next plug." I have to ask "what kind of fun are you thinking?" He grins as he says "we can teach him something new." I shrug feeling like he's taking full control now and it'll be difficult to regain but he's also done this more than I have so maybe it's better this way. "OK dad but tonight you're not going to do anything right?" He grins again and says "do you want to sleep with us to make sure?" I sigh so he says "I won't do anything Hen, promise. Why don't you lovebirds go get some sleep because we're going to have a big day tomorrow." I go into the master bedroom finding Oliver already laying in bed with the covers pull up over him. I ask him how he's doing and he tells me he's doing good, his butt feels weird but it doesn't hurt. I kiss him on the forehead then tell him to get some sleep and I will see him in the morning. He leans in before I pull away and kisses me on the lips, I kiss him back a little more deeply feeling his tongue sliding into my mouth. We both let out a soft moan before he breaks the kiss and says "goodnight daddy, I love you." I stand there looking at him, my precious boy as he wiggles around looking to get comfortable I say "I love you very much Oliver" then head out of the bedroom. I stop to give Dan a hug "thanks for helping with this dad" I say before I go to the guest room where Eric is laying down then crawl into bed with him. Once we're both settled in bed I have him roll on his side facing away from me then wrap my arms around him holding him close to me. He scoots back pressing his ass against my cock which is firm but not fully hard but I really want to talk to him so I ask "you said we'd talk about it later, coming to Boston, so do you have any thoughts on it?" I can practically hear the smile in his voice as he says "of course I have thoughts, I want nothing more than to be with you and Ollie, shit bro I fucking love that kid but I'm just worried that I won't fit in out there or be able to find a job or... fuck bro... what if you get tired of me too." I lean my head into the back of his neck kissing him softly then say "I know you got fucked over and you're still dealing with a lot of that hurt but we've been friends for so fucking long if I was gonna be sick of you that would've happened a long time ago." We both lay there quietly for a few moments then he asks "well give me a bit of time to think about what I need to do, is that okay?" I laugh softly and say "of course it is, I'm not out there dating randoms looking for some guy and if anyone is going to be part of me and Ollie's life there's no better man than you." He practically spins around "really Hen" he exclaims now looking in my eyes I can see tears in his so I tell him "yeah bro, Ollie adores you and well I guess I kind of like you a little." We both start to laugh then I say "take the time you need to figure it out, like I said I'm in no rush and I want you to be certain about your decision." He throws his arms around me nearly crying now "thanks Hen, fuck bro I love you so much." I hug him tight and say "I love you too now let's get some sleep, sun will be up before we know it and you know Dan's gonna want to get an early start." Eric chucked and says "sure thing... that man is itching to pop that boys cherry, hell I think deep down you are too aren't you?" I look away feeling myself blushing he says "fuck yeah, I knew you were you fuckin' perv." I punch him in the shoulder then tell him "roll back over so I can cuddle your annoying ass" and once he does we both gradually drift off to sleep.