The Hole

by WantonOne247

29 Oct 2023 1254 readers Score 9.4 (11 votes) PDF Mobi ePub Txt


So just to recap a bit, my name is sam, I'm bisexual though recently I've been more on the receiving end then the giving end. I'm not complaining. As for my current situation, the last two nights i thought i was getting  royally screwed by a hung trans woman. Turns out it was my friend Dean, who so happens to be a trans man. Either I don't read well or some information wasn't given in the ad. Again, not complaining. So without further ado.

As I come to, I notice a few things.  First I'm still kneeling oh the couch but I have a blanket draped over me, Dean is sitting on the couch in a bathrobe staring at me and lastly that enormous horse cock is still lodged up my ass.

I look at Dean and ask" so hooowwww's it going?" - "I've been fucking your brains out the last two nights and that's all you can say?" - "thank you, sir. May I have another?"  -  "I'm serious, why are you here, how did this happen?" - "ok, ok" I say "you know exactly why I'm here, I was getting fucked by you if you forgot. Though at the time I didn't know it was you! Did you know it was me? Did you set this up to out me?"- " No, I didn't know it was you, I didn't know you were bi. I thought I was banging some power bottom. even if I knew, I would never out you.  Your my only guy friend who's ever looked at me for who I am, not what I am" - "I never cared about what you were. I only care about You!" Dean looks at me dumbfounded "what do you mean? As I stammer out my response I look away as I tell him. " I care for you, honestly I have feelings for you. I just never told you, not sure if you've forgot but you've been in a relationship for what? Seven, eight years and you like ladies. So there's that"  As we sit there in silence the reality of the situation sinks in. I need to see where this can go, if this can become something more.

So I ask him "why did Lauren leave you? the truth, please" "At first i was still a girl, albeit a tomboy, we are good together. Happy little lesbians, but i needed to be honest with her and myself. I told her how I felt  Like a man trapped in women's body How I needed  to become my true self. That I wanted to transition.  It took her a bit to get her head around it but then she seemed happy for me and we were good  but then It wasn't so good. The last few years after I transitioned she told me She didn't feel the some way as before.  it wasn't the same that I wasn't the same And she was right. things were different.  She said that she couldn't stand being seen with me. All she saw were people staring at her while she was with me. So she left. It was my fault" All I can say at first is "im sorry" but then I continue "but do not apologize for being who you are. Her leaving was not your fault but her doing. She wasn't able too love you inside and out, not how you deserved to be." Like I could, I think to myself.

"So why all this? Why banging guys?" 
"I wanted to know what its like, Lauren was pretty much a prude for lack of a better word. I wanted to fuck some one like they do in pornos, fuck someone that wanted to be fucked, that wanted it as bad I wanted to give it. but that didn't happen..... til you, Sam. That first night was everything I could ever want. You didn't run away when I entered you"  "speaking of which, I think you left me with some unfinished business" as I shake my ass making the blanket look like I have a tail swaying back and forth. Dean jumped up so fast it was comical, not to mention I got a full view of deans naked body.  As Dean grabs the strap of the harness and the base of the dildo, and as he did I pushed back taking it up to the ring.  Moaning out loud, I look back at Dean and simply smile. Dean stares at me for a second before releasing the strap on harness and disappearing behind the glory hole wall. 

When he reappears, he is sans bathrobe and holding what I assume is a bottle of lube. Dean steps up behind me, taking up the harness once again and begins to don it. All the while eliciting small moans and groans from me as this giant cock moves all around inside me. Once Dean is all strapped up he looks my straight in the eyes and asks me if I'm sure about this. Looking back at him, I tell him this is what I want, that he is everything and the only thing I want.   With that, he applies some lube to both of us and proceeds to push his cock into me, upto the ring , then pulls back an inch and pushes the ring as well as the last hands width in me. Simultaneously wrapping one arm around my waist and the other around my chest drawing our upper bodies together for the first time. utter bliss, as he starts rocking his hips. Feeling the ring pulling out, stretching me then to be pushed back in to the base stretching me wide open. Feeling us giant balls against my own. I can feel his cock pushing my abs against his arm as he takes me over the edge. Hearing my moans and his grunts. Him rubbing himself against the harness getting off, pushing into me like never before. Before I know it I feel cum blasting through and out of the dildo. I cum instantly, every last ounce of energy in me gone. Dean slumps down on my back, both of us panting. 

And as strange or as Cliche As it sounds I finally feel  like I belong right were i am and with who I'm with.

TBC