Toby's Journal

As I sat there for what seem like an eternity waiting for a towel to wipe my shot spooge from my face and body, Bobby Joe just sat across from me, sipping on his Scotch and smoking a cigarette. 

Eventually Joey Bob turns up with a warm and soapy towel and hands it to me.  I used it to clean myself quickly.

Once I got most of my cum off of me, Bobby Joe said to me, “your one hot stud Toby.  My brother and I would have job for free if you either fucked the both of us or you let yourself to be bred by either one of us, but since that didn’t happen. . .”

I interrupted Bobby Joe by saying, “what finger fucking my asshole wasn’t good enough for you to get off to?”

Bobby Joe then said, “let me finish please and from what I saw, you didn’t mind the prostate massage that my brother and I gave you too much in that we've never seen so much cum shoot of a dick before unless it was in a porno, but now that the pleasure part is over Toby, let's talk business.”

I replied, “can I get fucking dressed first.”

Bobby Joe was about to say something but Joey Bob interrupted his twin brother and said “sure.”

As I dressed Bobby Joe gave Joey Bob a dirty look, but once I was fully dressed and the so ready to get the fuck out of their house, the three of us worked out the plan for them to get access to Ted's computer and the price.  I told them that I could do five hundred now at the most and the rest in a few weeks.

Bobby Joe didn't like hearing that.  He wanted all the money up front due to some techy psychobabble that I really didn’t understand but it was Joey Bob that said, “five hundred down is good.  The other five hundred once the job is done and Toby sees what’s on the computer.”
 

Bobby Joe just grunted angrily and then nodded his head before saying, “five hundred now, Toby.”

I then fished my cellphone phone from my short pockets.  I saw that there were many text messages and voice mails from my mom and Ted, all wondering where I was at in that the hour was late and that I had a game tomorrow and asking if I was drinking.

As I read them I knew that I was in a world of shit with them unless I came up with a believable cover story.  I then opened up my banking app and said to Bobby Joe, “I'll Venmo you the money, your email please?”

Bobby Joe then replied, “yeah we only deal with cash on requests such as this, so five hundred in bills before we do anything.”

I agreed but told them that it would be on Monday at the earliest.  Bobby Joe said that was fine.

Once the “business” was concluded with the Scots, I got up and left.  As I was leaving Joey Bob was walking me back to my car and kind of apologizing for his twin brother.  I told him to save it by saying, “look Joey I like you and we all had a good time tonight but your brother is bit of a dick so to me at the moment as much as I would like to keep on seeing you again and maybe we can in the future, but for the moment, let's keep things strictly professional.”

Joey Bob looked at me with a bit of a sad face and said, “I understand Toby, Bobby can be a bit too much at times but it doesn’t always have to be that way” as he got closer to me and attempted to hug and kiss me.

I stopped him in his tracks by saying, “the hour is late and I gotta go Joey.  I’m in a world of shit with my parents for being out so late as it is.”

Joey Bob said to me with a sadden face, “I understand Toby.  Hopefully we can see each other again soon and this time I'll make sure that your creepy brother Bobby is not around.”

Joey Bob replied, “yeah, he comes across like that and I understand. Have a good night Toby.”

As we parted ways and about to get into my car, I then said, “wait Joey.”  He then turned around.  I went up to him to give him a big hug.  He then bent down to kiss me.  I kissed him back.  We kissed for a long time and I started to feel my dick getting stiff again until I broke it off and said, “once our business deal is over, I promise.”

Joey Bob looked at me and said, “I hope so.”

I then got in my car and drove off back home. 

As I drove home my ass hurt a bit from the prostate massage from both Bobby Joe and Joey Bob but at least it gave me an insight on what Jake’s cock inside of me would feel like, that’s if it ever will happen.

I must have loved it in that I have never came like that in my life before and while I have seen some gay pornos of guys either fingerings their assholes or shoving big dildo’s up them while they jerked off, I have never done anything like that before.

As I drove into my subdivision, I then had to then think of a quick cover story to tell both mom and Ted and prayed that they would by it.  Once it came to mind, I decided to roll with it even though it was totally plausible and won’t get many questions.

 

Once I drove into the driveway, mom was outside with her usual Vodka Tonic and a cigarette in her hand.

Once I got out of the car, she yelled at me and said, “where the hell have you been Sean Tobias, I was worried sick about you!!”

I replied back, “sorry Mom, I just lost of the time.  I was hanging out with my friends and all.”

She then said to me, “are you sure that was all Sean Tobias?”

I just wanted the night to end and to shut her up so I said to her as I stood by her and said, “yeah sorry I didn’t respond to either of yours or Ted’s texts and calls but I was busy losing my virginity.  The rubbers that you gave me money for did come in handy.”

That shut Kathleen up real quick.  So much that mom had to take another drink and drag of her cigarette before saying, “well Sean Tobias you are no longer my little boy anymore but have become a man, and a very responsible one at that.  I'm not ready for bastard grandchildren like Maureen has.  Time for a drink to celebrate.”

I said back, “I better not.  It’s a long day for me tomorrow.  I need to wash up afterwards, you know.”

Mom was rather insistent and replied back, “it’s Ford family tradition.”

Mom and I then went into the house, to into the study where Ted was seated by my late father’s desk and said to me, “where the fuck have you been Toby.  You had your mother and I worried.  You didn’t respond to our calls and texts.  I was about to call the police.”

Mom then said to Ted, “can it Ted.  It’s not like you really cared for Toby to begin with.  He was out with his friends. Toby is almost eighteen now.”

Ted then replied, “he is your son Kathleen but I paid for his car and insurance.  I just want to make sure that he was neither texting or driving drunk.”

Before Ted offered me a drink, I went to the liquor cabinet and poured myself a big shot of Ted’s very expensive bourbon then said, “mom, refresh yours and Ted what are you drinking tonight?”

Ted looked at me in an incensed way and said, “same as you Toby but you should have asked first.  That stuff is expensive.”

I just replied back, “sorry Ted but mom insisted that we all have a drink to celebrate.  It’s a Ford family tradition.”

Ted went from being upset to then confused and then said, “what’s going on Kathleen?  An hour ago you wanted to kill the boy but now we are all sharing drinks.  What gives?

Mom just said, “it was a special night for Toby.  He was with his prom date for tomorrow.  I do so want to meet the girl.”

I then took another big sip of my drink and said, “ohh it wasn’t her and please don’t spill the beans to Annette.  She would kill me if she found out.  Annette still believes I’m a virgin.”

Mom then had a shocked looked on her face and said, “ohh, who was the lucky girl then?”

I said back, “just a girl from the Co-Ed prep school in town.  We met a couple of years back.  She was in town this weekend, we reconnected and then one thing led to another and then we both really ‘connected’ if you catch my drift.”

Ted then said, “ok I have heard enough.  Kathleen may I have a word with Toby alone?”

Mom then said, “sure Ted.  I need another smoke anyways.”

Once mom left the office, Ted just looked at me as he sipped on his drink and said, “got laid tonight Toby?”

I replied back to him as I sipped on his expensive bourbon, “I did, and used protection.  If this is a talk about the birds and the bees with my stepfather, then you are a bit too late Ted.  Can we make this quick because I have a very long day tomorrow?”

Ted just said, “sure Toby.  So that thing in the shower at my club with Vaclav. . .”

I slammed the rest of my drink and replied to the tool of my stepfather, “was a similar situation with you and the Latino locker room attendant from your club, and in this house no less.  I thought we both made a ‘gentlemen’s agreement’ about not discussing that.”

Ted then said, “I just want to make sure Toby.  Kathleen just started sleep in our bed again.”

I slammed my glass down and said, “What you and mom’s ‘arrangement’ is not my business Ted and by the way I need an extra five hundred in my account that I can access.”

Ted then replied, “why?  Your mom and I give you a generous monthly allowance as it is.”

I replied, "It’s for my car repairs.  Don’t worry I will pay you back in a few weeks.  You know that and it must be is cash.”

Ted then asked me, “why cash Toby?  Are you using it to buy drugs or something else.”

I then just stood up and said, “give it a rest Ted” as I slammed my drink glass on dad’s old desk, made a good dent in in that dad would appreciate and added, “it’s because they do side work on a cash basis, so no taxable income.  Something that you are good at in always moving money around so that the IRS doesn’t find it.”

Ted then stood up and said, “you just dented my desk.  It will cost a fortune to get that out.”

I just replied back, “no Ted I just dented my own desk that you currently use at the moment, or had you forgotten?  Patrick willed it to me so I just gave some more of my own character just like when Patrick and I would bash my toy cars into its legs.”

Ted had no words after that as I stood up and left the office and went to my bedroom.  There I stripped and then went to take a hot shower.  I had a bit of a buzz from the bourbon as I washed my hair and body.  When it came to my private areas, I soaped up a wash rag to clean up both my dick and ass.  As I soaped up my ass, I felt my dick getting a bit stiff again. 

I then added more of the soapy body wash to give my asshole a better cleaning after Bobby Joe and Joey Bob rimmed and probed it as I did so my index and middle fingers slid easily right into it.  As the very warm shower water ran all over my body, I then started to finger my ass and as I did so my dick was getting fully hard again.

I then grabbed the detachable shower head with one hand and then sprayed the water stream all over my cock, especially around its now swollen and sensitive cock head.

I then put the shower head back on it’s mount and then started to quickly jack my cock hard and fast with my right hand as I kept on probing and driving my now three fingers into my asshole with the left one.  I kept inserting and withdrawing them and finger fucking my ass until my middle finger was so deep into it that it hit was rubbing through my poop chute and along my g-spot.

As I did so my cock started to leak pre like crazy as I kept on jacking it.  I kept on jacking it hard as the water was starting to get cold while imagining Jake’s cock in my ass.

As the shower water was getting pretty cold, my balls started to tighten up into my body and shoot up high while I still had a massive hard on.  That was when I took the soapy wash rag and then jacked my cock hard with my fingers up my ass and quicky jizzed my second load of cum for the evening.

After I came, I was physically and sexually exhausted. 

As my hard dick went down and I washed off the fingers that were up my ass, I turned off the shower, got a towel and dried off.

As I dried off my body from showering, I looked into the semi-steamed up mirror that was in the bathroom and took a moment to look at myself.  As I looked at the reflection of myself in the mirror the only thought in my head was, “Sean Tobias O’Malley, you have definitely turned to the ‘Gay Side’ and loved it.”

I then brushed my teeth and flossed.  I didn’t bother changing into my sleep tee and shorts and decided to sleep in the buff instead because I knew that tomorrow will be a busy day for me. . .