Jack and Toby Ch. 07

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kmillerk1
kmillerk1
352 Followers

***

The light was blinding, I pulled the covers over my head and went back to sleep. I don't know when I felt a warm hand rubbing my shoulder and Caleb's voice breaking through to bring me out of my sleep. "Toby... Toby... come on Babe. Wake up."

"What?" Oh shit that hurt, I moaned.

"Here take these." He handed me four Tylenol and a bottle of water. "I have a cup of coffee for you too."

I tried to sit up and he helped me. "How did I get here?"

"I assumed you came by cab, you showed up at my door already fucked up. I know you could've probably drove home when you left, but I really didn't want you to leave. When you came back, you were so shitfaced, you didn't last long after you walked through my door."

"I'm sorry man, I shouldn't have bothered you." I almost fell over trying to get up.

"Shit Toby, what happen?"

"Jack was at home, he questioned my loyalty. He fucks around on me all the time and he questions me." I put my head in my hands. That is when I realize I only had boxers on and I saw my jeans and t-shirt over the back of the chair and went to reach for them.

"Don't worry Toby. I just took your clothes off so you could sleep. I didn't do anything else, I promise."

"Why?"

"Why what?"

"Why would you want someone as fucked up as me?"

Caleb chuckled and actually blushed, I looked at him. "Toby, I've always had a crush on you." He chuckled again. "Well at least in high school and you're still as sexy. I'm still just as drawn to you, maybe it's just because I had just broken up with my boyfriend, I don't know."

"You didn't tell me that."

"I didn't want to talk about it. I just wanted to forget and have a night I just never talk about or maybe I do, I don't know."

"I actually know the feeling Caleb, even though Jack isn't gone and especially after he questioned my loyalty last night."

We looked at one another, he got up from the chair he was in, walk over to the bed and sat down next to me. We gave in to one another, he wanted to forget his boyfriend or his break-up.

I don't know what I wanted. It wasn't to show Jack, I probably will never tell him about this. I'll probably never admit that I did anything when I leave this room today. Maybe this is to get an ounce of myself back, I don't know. But I do know this was the most careless thing I've ever done in my life because we didn't even have any condoms.

We started out again just kissing and caressing one another. It advanced quickly from there Caleb kissed down my neck, pinching both of my nipples, he had me erect before he even sat next to me and he knew it. "You always did have a nice cock, Toby. I always fantasized about sucking you in the showers after football practice." He pulled the waistband of my boxers down and I lifted up to take them completely off.

Before I had them pushed down my legs he had my dick down his throat. "Shit." I swore because he even had my balls squeezed tight. God did it feel oddly great and he made me quickly forget about my headache. "Get out of your clothes and let me have your cock."

He pulled off. "Are you going to leave if you cum once?"

"No."

"Stay the day with me?" Caleb asked.

"Yes."

"Then you can have me afterwards. By the way, I'm only a bottom, so I hope you weren't hoping to get fucked. But I hope I was." He smiled up at me.

Oh shit yes he was and no one has ever tapped me. "I'm only a top so you have nothing to worry about there but you better have some lube in this room."

"I bought some the other day hoping you would fuck me." He reached over to the other side of the bed to the nightstand drawer. When he did this I took the opportunity and jumped on top of him and pulled his t-shirt off. I started kissing the back of his neck and humped his ass, he laughed. "God Toby, I'm never going to forget this." I pulled his shorts off along with his underwear.

"What? Never forget that we had a wonderful lunch and dinner today?" I laugh, because that is all I'm ever going to remember happened today. I turned him over and I did want to suck him too, so I flipped so he could finish me off and I could suck him.

He had a good six and half inch cock maybe a little longer, but not much thickness, not like mine at least. He was doing a good job of fucking my face as I sucked him. I was also fucking his, I could hear him gag every once in a while. God did that get me even harder, I don't know why. When I started to cum, I think it pushed him over the edge and he started shooting his cum into my mouth and I was happy to accept every drop.

We held one another afterwards and kissed, I even stayed hard and was humping against him. I finally pushed Caleb on his back and kissed down his neck, stopping to suck each of his nipples until they were hard as chocolate kisses. He was moaning so loud, I loved it. Caleb was begging me to go down on him again. Oh I was, but I was going to be opening him up too.

I grabbed the lube that he dropped on the bed when I tackled him as he grabbed for it earlier. I flipped open the top and poured some out in my hand, I licked his ball sac and he shivered. I started to finger him and he moaned, I pulled his cock from his stomach and went down on him.

The moans I was getting out of Caleb made me so hard so as soon as I added the third finger I pulled them out, lubed my cock and pushed in. "Oh shit man, you're huge." I stopped so he could adjust to me. When he nodded for me to continue I pushed myself all the way in and bent down and kissed him. "Oh God Toby, shit you're big."

"I'll stay right here as long as you need." I continued to kiss him and Caleb wrapped not only his arms around me but his legs which caused me to lay down on him and I pushed further in.

"Oh God, Mmm. Roll over with me Toby, I'm going to do the piloting on this one." Caleb smiled at me. We rolled over together, I did end up coming out of him because he had to straighten his legs but he had me back in quickly and was riding a way. I would squeeze his chest, rub his cock and sometimes he would come down for a kiss.

I needed to fuck him, I knew I could get my release this a way but I needed to fuck him. "Let me fuck you, please."

"Oh, you don't like my slow steady ride?" As he reached around and grabbed my balls.

"Oh God, yes." I sat up and kissed him, God did it feel great to have his hard dick sandwiched between us.

"Yes Toby, please fuck me." He lifted off and got on his knees, I jumped up and was behind him in a flash. I entered him and you could hear our skin slapping against one another. All I was hearing from Caleb was moans or yeses and I was grunting

"Caleb I'm going to cum."

"Cum in me Toby, please." Because he felt me slowing down to withdraw, so I continued and slapped into him a few more times and I couldn't hear anything when I came. I spasmed so hard I thought my nuts were coming through my dick, it felt awesome. I could feel Caleb spasm below me so I knew he was coming too.

When I withdrew I dropped down on the bed and Caleb quickly covered me with his body and we were holding one another, caressing and kissing. I was wore out and quickly fell asleep and the last thing I remembered was Caleb laying his head on my chest and I was out.

When I woke later he was still laying with his head on my chess but I knew he was awake because he was playing with my chest hair. 'Hi."

Caleb looked up at me and kissed my neck. "Hey sleepy, want to take a shower?"

I laughed this is not going to go well. "Two guys in a shower, you know doesn't go well."

"I know but you can wash my back and I can wash yours." He laughed. "I would love to get you in the gym shower. I wanted to be on my knees so bad sucking your cock Toby or having you fuck me. What I wouldn't give to be able to do that."

"Well, sorry I'm not going to break into the high school just to fulfill a fantasy." I laughed. "Come on, we can try to fit in the shower."

"I take, you haven't showered much with Jack?"

Why did he have to kill such a good mood? "No." But it did bring me back to reality.

I think Caleb noticed because he pulled me out of bed. "No Toby, remember this day never happen. So let's take a shower and go have a very late lunch or early dinner and have some more fun." He kissed me and we went into the bathroom to shower.

***

I didn't make love or have sex with Jack of almost two months after Caleb. Not that I felt guilty or anything, that day never happened. But I made sure I was disease free. I never asked or talked to Caleb to see if he had any STDs so I tested a few times. Some you know within a week if you have, others you can't know for over six weeks. Jack has never brought anything home to me, I wasn't going to give anything to him.

But it wasn't like Jack even noticed that I wasn't putting out for him, he was hardly there. I don't know who he has been shacked up with this time, but I've noticed his clothes starting to disappear. That is normal when he starts living with someone part-time, he has to have some of his clothes there. They'll get tired of one another and Jack will come back like he always does.

**Jack**

Toby thinks I'm stupid, I know he fucked Caleb, he probably did that entire week. But that is okay, he can have his fun. I have Roy and he wants me, he felt bad for dumping me a few years ago and came to Glo and then to Aspirations with flowers a few months ago. Toby never does that and he knows I like them.

Roy also knows about Toby this time, I told him up front that I have a boyfriend. He told me he didn't care that he was going to win my heart. Roy asked if he could take me out on the side without Toby knowing. I told Roy the whole time we were dating before Toby didn't know. Roy smiled and kissed me.

One night while lying in bed I was snuggled up to Roy, which I do like. "It's Toby right?"

"Yeah, what did you want to know?"

"Where does he think you are?"

"He knows." I laughed. "But he's too much of a pussy to do anything about it. I've been fucking around on him for years. Every time I got bored or when he pisses me off."

"Wow, if you become mine. How am I going to know you aren't doing it to me?" Roy asked.

"Honey you would know, I don't think you're stupid. The first night I didn't come home?" Then I thought about and back peddled. "Well at least if you knew why I wasn't coming home, if it wasn't for work or something else that is."

"Yeah, you're right. So what do I have to do, to get you to leave this Toby?"

"We'll talk." I smiled.

kmillerk1
kmillerk1
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AnonymousAnonymousalmost 3 years ago

I can’t believe the reader who defended Jack, saying he was a good person and good for Toby to motivate him to stay on the right path. What absolute bullshit!!! Jack was a selfish asshole and user. He used everyone in his life for a different purpose. Whether it was money, material things, great dinners, trips, or in Toby’s case a handsome, meek safety net with a big dick that never questioned his infidelity nor held him accountable for his shit. He did not motivate Toby in any way to be better. In fact, I’d debate that without Jack, Toby would’ve finished college much earlier, would never had been demoted to night shift for years due to punching Scott, would’ve realized his potential much sooner and would’ve had several loving relationships with guys (like Caleb) who respected and valued Toby instead of using him. So glad that Toby seems to be coming to his senses and figuring out he is better without Jack. As for Jack, I could not care less what happens to him. He deserves the absolute worst in life and I hope he is treated as badly as he’s treated Toby for over a decade.

chilliwackbc2020chilliwackbc2020over 3 years ago

Why would anyone feel sorry for Jack....Toby would have done just fine on his own,,,,half the time Jack wasn't even there.....Jack was a selfish promiscuous little prick who only thinks of Jack.......

chilliwackbc2020chilliwackbc2020over 3 years ago

Jack, Jack, Jack, I do believe you are in for a big surprise....you are a little two faced f... tart

NymzanSusaurenNymzanSusaurenalmost 5 years ago
Issues

I know people probably hate Jack, but if this was a 'best friends' or "friend with benefits" instead of of an 'i love you' story, they would probably see things differently.

As you say later, he didn't really know what love was, so he THOUGHT what they had together was it. Yes, they do love each other, but they were BOTH clearly not 'in love' with one another.

I am sure people also fuss that this relationship should not have happened or should have ended sooner. I have my argument on that, too. Did you say this was reality based, or a real story? I don't remember. Point being this: Toby would never pushed himself to do better, get that degree, or a higher paying job without Jack. His high maintenance relationship drove ambition he didn't have. He would not have graduated his classes so quickly, or so well. And he would never have ran off across the country to escape his 12 year relationship...so, he never would have met, loved, or married his soul mate...Jake.

I think deep down Jack knew they weren't meant to be together, but he lives a very reckless lifestyle and something about Tobias gave him the stability he occasionally craved and needed. As well as safety...I am surprised he didn't get hurt more often honestly. I hope Jack finds his one true love and settles down soon. He may be an emotional drama queen, but he is really not a bad person. If he had been, he would have let Tobias flounder and die in obscurity. He lifted him out, gave him purpose, and set his feet on the right path.

I was hoping Roy might be his salvation. I find it worrisome that Jack came back even after this ends. I know, i know...You left it unfinished, so Roy may not have even been the one he was seeing at the time Tobias called it quits, but I am hoping Jack falls in love and just came for Toby because he was scared of it. Perhaps seeing Toby was gone for good, he will try to love...real love...and find his own happiness. I wish them luck. I hope you finish this...but even if you don't...I loved it.

mfa607mfa607over 5 years ago

Jack’s an asshole! Looking forward to seeing if he gets left alone like he deserves!!

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