Toby's Journal

by 138b

23 Nov 2023 984 readers Score 9.5 (25 votes) PDF Mobi ePub Txt


Author's Note:

My thanks and appreciation to those who are reading and following this story in that this is the first time I have done this before.  While I have so many sublots that I could add to it I felt that they would take away from the main focus of in that now the main characters have been established (but there are always future possibilities for them.)


Neither Ted nor mom had an appetite, so we drove straight on home instead in total silence.  Once we got to the house Ted offered to open the car door for mom, but she went straight into the house and up to her bedroom.

I was making my way in the house Ted asked if he could have a word with me.  I said sure and offered me a drink.  I accepted it and sat down in front of his desk.

“Weren’t you a bit tough on your mom today, Toby, she means well.”

I laughed softly as I took a sip of my drink and told Ted, “if anything else Ted I was being too gentle with her, she doesn’t want to really fucking know how I really feel of her, and you know that because you live in this house as well and have seen it all but never said fucking anything probably because I am Patrick's son and not your own. 

"Once you have a natural child of your own, you may think differently Ted."

“She never abused me physically but there are other forms of child abuse and her stunt today in the car just fucking provided it.

“She gave her word Ted to both you and to me in this very office that she would sign the papers and you know that. “

Ted said, “she did. You are right there and right about me.  I don't have a child, or a son to call my own, but I don't Toby.  You are the closest one and I tried to be the best stable and fatherly figure that I could but with your dad's sudden death and being his business partner I just wanted to make sure that his legacy could one day pass to you."

I changed the subject and replied back to Ted, “you tried warning her Ted last night what could happen to me if she cannot come to terms with me finally letting me be my own man for once and let me make my own decisions either right or wrong for once, so I had to force my hand in order for her to hear it from me while she was in a somewhat sober condition.

"So if I am expected by both you and Kathleen is for me to inherit the family business that my father built up from scratch, brought you on a business partner because of your access to capital and before his vision could come to fruition he died and then give it all up so I can be myself for once then I fucking will Ted. I goddamn swear I will. 

"I'm not fucking inheriting something that is being imposed on me Ted!"  

Ted laughs and said, “and I think you did Toby.  I agree with you in that she needed to hear it from you, that’s why I stayed out of it today and I believe that she got the message through her stubborn ‘Mick’ skull this time around.  You did just that.

Ted then asked me, “would you follow through on those threats you told Kathleen about living in a homeless shelter? Becoming a male prostitute giving hand and blow jobs to businessmen to get quick cash?”

I found Ted’s question very unusual and I took another sip of my drink I just replied back, “I don’t make threats Ted, only promises so if crashing at friends’ houses and living on the street until I can access my Trust Fund and if my situation became so dire then yeah I just might but then that wouldn’t me my decision but strictly yours and Kathleen’s.

“I just wanted mom to know to what extreme extent that I would go in order to get by.”

Ted just said, “I see.  I hope it never comes to that.  It would be a disservice to Patrick and to you.  You will always be looked after Toby even though you may not know it.”

We sat silently for a moment sipping our drinks until we both heard mom’s voice from the entryway into Ted’s off.  She said “Sean Tobias may I have a word?

Both Ted and I rise from our seats, and I said in my bad Irish, sea ​​Mháthair (yes mother).”

Ted added in and said “I’ll leave so you both can talk in private” for which mom said that he could stay as well.

Mom stood right across from me, with red eyes and dried tears on her cheeks. She asked Ted for her usual Vodka Tonic and as we stood in silence, Ted poured it and served it to her.  She took a sip of it.  She then said, “Sean Tobias, look at me.

I did and when mom gave me the biggest slap on my face that I ever had since I was eleven when I asked her if she was a ‘cunt’ because that is what my cousin Kyle thought she was and the slap stung like hell.

Mom just coldly said to me and said “Sean Tobias, that was no way to talk to your mother today” and then gave me a big unexpected hug.  I sure as hell wasn’t expecting that from her, especially when she started bawling out tears again.  She even got me crying a bit because yeah I showed her disrespect but then she broke a promise to me and broke it, not out of ignorant afterthought but out of absolute malice and for that I needed to call her out for.

Once we broke off our hug mom just said “you were right Sean Tobias, as much as it pains me, one day I will have you to be the young man you need to be, and for that I have to let go of my baby boy” as she cried and hugged me again.

I hugged her back and said in our Old Language and in a crappy Irish accent Tá brón orm a Mháthair, (I am sorry mother) but one day you have to let me go, if it’s not today, then when? When I go to college, will I have a family of my own? When does it stop with you Máthair (mother)?”

She pulled away, wiping away the tears from her eyes and said “it starts today Sean Tobias.  I don’t you want you, living on the streets, and being a striapach fireann aerach for money.  You know I feel about those kinds of people.”

I smile and said “well mom that was the last resort unless I could get you to see your ill ways.  I love you and you know that.”

Kathleen said back to me, “I know Toby.  Have a good road trip with your team, I’ll see you and Ted soon.  I’m heading to Maureen’s to stay the night before our drive to Asheville early tomorrow.  We both need a break from one another for a bit.  Ted help put my bags in my car.”

Ted does.

After all of the drama today I just pour myself a small shot of Ted’s good bourbon, take a sip of it and smiled in that I have finally broken my overbearing and controlling mother.

The next morning it was the usual routine, with running, checking my pulse rates, logging them, eating breakfast, drinking tea and goddamn Jake was right about it.

Weight trained with Jake as my partner in the school’s athlete’s gym and as we did so told me of a certain girl in his history class that has shown interest in me and it wasn’t big titted Rosarita Sanchez.  I asked him for her name, He said it was Monika Selaanne, the Finnish exchange student in that she sees you as quiet and stoic on the outside but a raging party animal down below and that animal has needs to be unleased in her pussy.”

I blushed some and thought that if there was anyone who I would want to take my ‘virginity’ away it would be Jake and no one else so I just said “that’s good to know.  I think we share the same algebra class together but ‘Frau Schmidt’ has given us assigned seats but I’ll be on the lookout for her.”

Jake just says “she and a ‘friend’ for me are joining us for lunch so be on your best behavior ‘Church-boy’ I haven’t gotten laid since I started school here.”

With everything that’s been going on with me I have almost forgotten that Jake was a little bit more open about his own sexuality and that’s what make me more attracted to him in that he is so open and confident about it and confides with me about it.

I blushed again but this time he apologized to me sincerely and said “sorry Toby, I didn’t mean to offend.  I know that discussing such things makes you uncomfortable.  You know going to an all-male Catholic School and all.”

I said to Jake, “yeah just a bit” as I tried casually to adjust my now hard boner that is hidden beneath my work out jock and very baggy gym shorts, but I had the feeling that my cock was leaking pre.

Before even the forty-five minute bell rings before the start of class, I stopped my workout with Jake to tell him that I need to get my signed papers by my mom to Coach Morrow and the school’s nurse so that I am officially cleared to play on IR and to travel with the team.

Jake said “good that you can come along I wouldn’t want to bunk with anyone else ‘Crop-Boy’, see you at lunch time.

I go to my locker to change into my school clothes and sure as hell I was right in that there is a big wet spot of my pre in it.  I quickly pull it off, put on my boxer shorts and shove it my locker and dress for class.

I gave my papers to Coach Morrow first, he looks over them and said to me, “looks like everything is in order O’Malley but a slight complication has arisen.”  I asked him what that was.  He said that he couldn’t tell me at the moment but by tomorrow he’ll have an answer and that he expects my ass on the bus for the away game, even if I’m on IR.

I said “sure thing Coach, I am a part of this team and wish to support my teammates in any ways I can even if it’s on the bench.  They are my brothers.”

Coach Morrow replied back to me “we need more players with your and ‘Scoundrel’s” mentality, ‘Crop-Boy’, I’ll see you on the bus.”

I just said, “yes Coach”, left his office, turned in my papers to the schools nurse and went to first period.      

As I went to Algebra class, I saw Monika take her assigned seat and I walked by. I turned my head and smiled at her.  She smiled back.  She was cute, pretty hot looking for a girl in that she had long blonde straw blonde hair and pale blue eyes and from what I could tell a nice set of tits.  I took my seat and dreaded the next hour of “Frau Schmidt's class.

During lunch I caught up with Jake, and we got today's slop line the school calls nourishment; it was something they were passing off as build your own vegan burgers and hot dogs’ day with chicken nuggets and an option as well.

We took our seats and as we were about to eat Monika came over with her “friend”.  Jake and I rose and introductions were made.  Jake said “Monika, this is Sean O’Malley, but he goes by Toby.  Toby this is Monika, she is our exchange student from Espoo, Finland and this is Annette DiMarco, her friend and who she is billeting with.”

And as soon as the introductions were made Annette said in her very thick New Jersey accent “oww my gawd Jake it the guy's life you saved?  He is so cute.  Jake didn't give you mouth-to I hope" as she giggled and snorted loudly through her nostrils as she sat down right next to me and placed her hand on my lap.
I gave Jake the “what the fuck have you gotten me into bro” look as Monika had a look of disappointment on her face and sat by Jake.

For the rest of the lunch period Annette went on and on non-stop about how I was doing, what I have, asking about my personal life, what Catholic School I went to before and talk about going to one in Patterson, not that I really gave a fuck about it and when she stopped talking and snorting loudly through her nose, I told her that I went to an all-male prep school before coming here.

Annette then went on and on while I was trying to eat lunch and on occasion giving Jake more dirty looks. 

I knew he meant well but still for the time being I was in lunchtime hell.  Jake and Monika were trying to have a conversation as well and on occasion as he and she were chatting and smiling to one another.

The bell rings that lunchtime is over and as we take our trays of slop that is considered fit for human consumption and dump the food in the trash, the four of us go on to our next class with Jake right next to me and out of earshot of Monika and Annette saying “I am so sorry Toby.  I was trying to hook you up with the Finn and not ‘Snooki'”.  I just told Jake that was okay and that he tried to hook me up and I appreciated it.

While there was no official team practice after classes, there was an unofficial one with some of the guys from the team, which I joined in on.  We just farted around on the field by picking up, running and passing the ball to one another while trying to score against his “Worshipfulness” Dean.

It was nice to just be with the team and yes after everything that has gone with over the past few days and knowing that mom was on her way to Asheville, I could come home to a peaceful house for once in the past few days because Ted never gave me much grief in that he always left it to Kathleen to either feed or reprimand me.


After the practice my teammate and I showered again.  Jake apologized again for how the meeting with Monika and Annette went down during lunchtime.  I told him not to worry about it.  As he was washing his bare muscular chest and then his privates, he asked me a big favor of me.  I asked him what it was.  He asked if I could be a “wingman" on a date with him and Monika, and that Annette has to tag along as well considering her family is billeting her.

I told Jake straight out forward “I owe you a ‘life debt' Jake just like Chewbacca to Han Solo so if there is anything I can do for you just ask and if it means listening to ‘Snooki' go on and on so that you can get laid, then so be it.”

Jake just looked at me blankly and said that he didn’t get my “Star Wars” reference back to me as he lathered up his cock some more with the soap and as gave Jake's man-junk a quick glance I notices that it was getting slightly stiff.

And I lathered up my bod, nads, taint, and butt Jake said to me “looks like you got a nice set there ‘Crop-Boy’ so if you could get that ‘Jersey Shore' gal to take even some of that into her mouth you just might shut her the fuck up for hopefully five, ten, maybe fifteen minutes or so and if you are a quick cummer hopefully at least one minute.”

I just said dryly and with one of those infamous Han Solo grins and said “well hopefully for two minutes at least but ‘Snooki’ will be still talking as she chokes on my big ‘Mick’ cock.”

After that comment Jake and I just busted out laughing while we finished up showering and went back to our lockers.

As Jake and I dried off and dressed Jake asked me what I thought was so funny back in the shower room.  I just said to him that I have had a rough few days lately and while not going into my personal family drama that for the first time I found something to be actually laugh about.

Jake just said “I bet. While I don’t know your mom or step-dad but your mom comes off as a bit ‘extreme' to me but you having that medical scare and . . . ”

I whispered back “you have no idea bro.”

Jake was silent as we finished up dressing our gear and school bags, were about to leave the locker room, and with no one around, Jake gave me a sudden hug.

As we hugged Jake said to me “I can tell that you have had a bitch of a week ‘Crop-Boy’ that’s for sure.  While I don’t know what else is going on with you but I'm sure you got a lot going on. I'm just letting you that I'm here for you when and whatever you need.  Call me your brother from another mother or whatever but I'm here for you Toby as I said I want to see your ‘Mick’ ass back on the field and to be our team captain next year.”

My cock got hard as Jake was hugging me and I broke off it off early because I didn’t want him to feel my growing chub touching him, so I just said that I gotta get back home and that I'll see him on the team bus for the away game tomorrow. . .

by 138b

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