Jack and Toby Ch. 01


Hello Everyone,

I know it has been a little while. I have a little writer’s block going on. Of course it came when I was working on F&L so I worked with a few friends and we edited a few chapters of Jack and Toby. This Chapter was never supposed to exist, I actually was writing all seven (now eight) chapters of Jack and Toby at the same time and came to a dead-end. Wondering why Jack started cheating if he “TECHNICALLY” loved Toby in the beginning.

Chapter two will be out within a week (or so depending on when it gets published by Lit) I’m just running through it one or two more times. As I had wrote in my profile no one will ever say something is completely edited perfectly, I’m writing this for free, I can’t pay anyone to edit for me. So between two friends (I call my semi-editors) and a third reader (another friend) I hope that we catch most of the mistakes.

As always all comments and emails are welcomed, I am learning to “BREATHE”. My Ducky is still not here to help me float some days. But with the help of others I’m bobbing in the shallows.






When I walked into drama class on the first day, I literally already hated this school. Everyone was so mean to me, I really didn’t help things much I was an absolute bitch back. Walking into class, late of course, because I couldn’t find my way around the high school to save my life. All the football players started whistling and hooting at me, one of their many methods of making fun of me. Except for one, he looked down almost immediately. I found out a few classes later who he was, the captain of the football team Toby Smith.

The last class of the day, was choir. I walked in with Casey, a girl who had befriended me at lunch. Toby was already getting in trouble for fooling around with his friends. Football players I heard all take easy classes so they can stay on the team.

Toby was a senior, where I was technically classified as a junior, but if I completed summer school I could graduate. That’s what I get for playing around too much with a few too many guys and why I transferred to this school.

For the first week of classes Toby wouldn’t even look at me, but I knew it was him who made the guys stop teasing me. I don’t know how I always know but I knew he was hiding the fact that he liked guys. He just fit the type of tough guy that liked guys. I’d made friends with a few girls, guys wouldn’t come anywhere near me. So I asked what Toby’s story was, did he date?

They told me he was dating a girl named Jessica but they’d broken up at the end of his junior year. That rumor had it, Toby never wanted to do anything with Jessica. I asked what did they mean and they told me he never wanted to make out with her. She hated it, having one of the hottest guys in school and he wouldn’t touch her. I just smiled after that, bingo I knew I was right.

I was cast in the fall musical as Perchik in Fiddler on the Roof, so I couldn’t pay too much attention to Toby, but God did I watch him. I did get to see him play in a few of his games, but I really don’t like sports. He is a very cute sight to see, blonde hair and blue eyes.

It was in November when, Mr. Reed asked if I wouldn’t mind helping a fellow student out studying and learning lines so he could pass the verbal portion of the tests. I didn’t know when I said yes that it was going to be Toby. I thought he was doing fine in the class, but I guess he wasn’t if he needed help.

So when Mr. Reed stopped Toby after class to talk to him and asked if I would stay, I was amazed when he partnered us up. Toby smiled and introduced himself to me, he was very polite. After I introduced myself and we set up a time to start meeting after school, his buddies busted back in the room and he was gone.

I met with him a few days after school and on Friday since football was over. I asked if he was doing anything with his friends. When he said no that they all were out with their girlfriends, I smiled. Toby looked at me and it’s when I decided to make my move and was hoping that I wasn’t wrong, because I could get my ass kicked.

“Toby, do you trust me?” I looked him in the eyes, I’m a lot shorter than him but when someone is over six feet tall and a muscle God, he would look tall to anyone.

“I don’t know you well enough to trust you.” Logical even at seventeen.

“Okay, then I’m just asking you to trust me then, come with me please.” I stood and he was reluctant to stand, so I took his hand and pulled him to the closet which was in the drama room. It held a ton of props and other things, it was fairly large. I pulled him inside, I turned the light on and there was a step stool so it was just perfect to step on and be at the right height as Toby.

“Jack, what are…?” I didn’t let him finish his question, I pulled him to me and kissed him. There was no hesitation in him, he started kissing me back right away and he pulled me close to him. I could feel that he was hard, and that made me happy because I did like Toby. When we stopped kissing, Gaziantep Escort Reklamları I knew he was in a flight mode.

“Toby, it’s okay.” I pulled him back out of the closet. “Sit down for a few more minutes, please.”

“I really should get going.” I just nodded, I wasn’t going to keep him there, and he fled from the room.

I collected my things and went to my locker to get my bag and the rest of my books for the weekend. I headed out to catch a bus home, hoping I wouldn’t have to wait long. I was standing at the bus stop for almost ten minutes when Toby pulled up and rolled his window down.

“Would you like a ride?” I’d figured he was already gone, because by time I had collected my things and been at the bus stop it was close to a half an hour.

“You don’t have to.” I responded.

“Jack, get in.” I smiled and opened the door. “Come on, I don’t bite.” I just laughed at him. He just drove around for a bit then he finally asked where I lived. I think he was trying to get up the nerve to ask me something else and finally he did. “How did you know?”

“How did I know, what?” I knew what he wanted, but I was playing dumb, I wanted him to say it.

“How did you know I… ahh… I’m gay?”

“I was hoping that I didn’t get it wrong.” I smiled at him when he looked over at me. “I asked about you and I was told that you weren’t very sexual with your last girlfriend.” He didn’t say anything so I went on. “I like you Toby, you’re cute when you try not to look at me in class.”

“What are you doing tonight?”

“Nothing, why?”

That was the first of many nights that I spent at his house, well I didn’t spend that night. We walked in and Mrs. Smith, just happened to walk out of the living room to head to the kitchen and was surprised to see Toby with someone.

She greeted me and told us to come into the kitchen that there was food on the stove to eat up. She was trying not to stare at me, but I know she was. I know sometimes I can be a sight to people. I do like to stand out.

Being the skinny kid that can’t gain a pound if his life depended on it, also being five-seven, doesn’t help much. Semi tall and skinny, oh and I was blessed with brownish red hair. I hated my hair, so the first time I ever did anything to it, I bleached it platinum blonde after that I went reds. So when I walked into Toby’s parents’ house for the first time, I had it fairly bright red with a few black streaks.

Mr. Smith came into the kitchen looking for Mrs. Smith. He saw Toby first, went to say something and stumbled with his words as soon as he saw me. “Dad, this is Jack. He’s helping me with Drama class. I told you that I asked Mr. Reed for help and he partnered me with Jack.”

“Oh, it’s nice to meet you Jack. Welcome to our home.” I thanked him and both he and Mrs. Smith left the room.

“I’m a freak to them.”

“Not to me.” He made me smile. “Want to come up to my room, we could study more or talk.” We put our dishes in the sink and went up the back staircase. Toby had a decent size room and when I walked in I walked straight to his bed and sat down.

He closed the door just as his sister was popping into view. “Toby, I need to ask you something.”

“What is it?” He asked as he opened the door.

“Who’s that?”

“A friend, what do you want?” She asked him for some money and he just gave it to her to get her away. He closed the door and then took his desk chair and stuck it under the knob.

“You don’t have a lock?”

“No, my dad’s a cop, he doesn’t believe that his kids need locks on their doors.”

“So anyone could walk in on you at any time?”

“Yup and it’s not always the greatest time. Sarah has walked in on me more than once doing, you know.” I just laughed. “I just thank God I was under the covers every time.”

“When did you start doing the chair thing?”

“Just this year but if my dad ever caught me, it would surely be removed.”

“Why? He should realize you need privacy.”

“My older brother is the one that screwed it for the rest of us. Mom found drugs, my perfect brother Matt was found with weed. So for the longest time, if the rest of us wanted to close our doors we had to have a good reason. They have lightened up a lot, but I still don’t want to find out if he would be upset or okay with me blocking my door.”

“So there is just the three of you?”

“No four, Matt, is away at college now. Me, Charlie, you might have seen him in school, he’s a sophomore and then Sarah, she’s in eighth grade.” He had sat down on the bed.

“Was it okay. What I did earlier?” Toby looked at me then slowly nodded. “Do you want to do it again?” Again he slowly nodded. I climbed over in his lap just as someone knocked on the door.

“Get your books out” Toby whispered and walked over to the door and took the chair away. “Hey dad.”

“Tobias, I was just checking to see if you two boys need anything.” Boy was his dad afraid I was the school druggy or something.

“No dad, we were just going to run some lines before I took him home.”

“Alright son, remember you do have a curfew.” His dad walked away as Toby shut the door again, but this time he didn’t bar the door with the chair.

“When is….” He answered my question before I fully asked it.

“Ten that was my doing, not my brother’s.” He smiled, I just looked at him inquiring more information. “A party at the beginning of the school year, police were called. Dad had to come get me.”

“Boy aren’t you just full of surprises, I’m amazed you have a door at all.” I laughed, I don’t think Toby thought it was funny. “Come on we have a little time to run a few lines, I’ll make it interesting for you.”

“How so?”

“Just come sit here and run some of your lines, try to say them without looking. If you get them right you will know it.”

Toby ran a few lines from Othello, a few he got wrong, a few he got right and once he got them right he realized what would happen. I kissed him. Sometimes I would kiss him on the lips and sometimes on the neck. After a few lines though it turned into a kissing session, I’ll have to keep my will, if I’m going to help him at all. But he’s just so damn cute.

At nine he took me home, so he would make it back in time for his curfew. We talked on the phone a few times that weekend, and then of course during the week. Instead of staying after school to run the lines we would head back to his house. His parents really were wondering what was up, I’m sure. They looked at me every time I would come in and we would go up to Toby’s room. They would make some excuse to come in so we had to watch what we were doing and Toby could never put the chair in front of the door because sometimes they would just knock and walk right in.

Toby always protected me from his friends but since we started hanging out, he had to protect me and himself as well. But he told me to pay no attention to them. In the spring after Toby was asked to play a small part in Shakespeare’s’, A Midsummer Night’s Dream as Snug, the Joiner. It was fun getting him ready to play the part. I was in the play too, I played Tom Snout. But I’d played in this play before so I didn’t have to worry so much.

But getting Toby ready for it was fun, every time he would get a line correct I would start to rub his cock, he creamed his pants more than once. We almost were caught by his dad, I’d just pulled my hand out of Toby’s sweatpants as his dad knocked and walked in.


When he graduated high school, his curfew was lifted so he could finally stay out late with me. My parents weren’t the best, they left on vacation a lot without me. So summer was the first time we were able to be alone with one another and could have sex.

We were both eighteen so both of age and I had a lot more experience in this area than he did so I started out slow with him. We were in my room and I was kissing on him and I moved down, hoping he wouldn’t say anything. Because as I said we’ve never done anything other than hand jobs and kissing.

I pushed his t-shirt up and kissed his stomach. “Jack?” Toby said as I unbuttoned and unzipped his jeans.

“Let me please.” He didn’t say anything he just lifted up and helped take his pants and underwear off. He was so hard, I knew he was big, just by giving him hand jobs but oh God he was a nice size and thick, oh my God was he thick. I wanted to measure him, maybe Toby will let me later. I licked up some pre-cum and smiled he tasted wonderful.

When I took the head of his cock in my mouth, I thought he was going to shoot right then and there. He moaned and reached for my head. I smiled around his cock and held his hands away. I took hold the base of his cock again and started sucking him in farther and farther, it had been a while since I’ve had a cock in my mouth.

“God Jack, shit I’m going to come.” I knew he was, I rubbed his balls and that was the end of him. He started cuming and I drank it all down, he wasn’t expecting that at all. When he finished cuming he pulled me up and started kissing me, I didn’t swallowing all of his cum and he got to taste himself. “God Jack, that was fucking awesome.”

“Do you want to try that on me now?” I knew he had never sucked cock before, so he probably would be very hesitant.

“Yes, I do.” He didn’t take any time in deciding, which surprised me. He kissed me and started kissing my neck, pulling up my polo, he even sucked my nipples. God do I love that, I didn’t even think to do that to him this time. I unbuttoned my pants and he unzipped them, pulling them and my underwear off all at once, I couldn’t believe he was that quick.

I’m not as well-endowed as Toby, I barely have a six inch penis fully erect and it’s not that thick. But I was hard and he wasn’t scared to lick or suck it. He has several times touched me as I said we’ve giving each other hand jobs, but it was generally with sweatpants on. Oh did it feel good, it has been a very long time since I’ve had someone lick and suck me. Long since before I transferred into Toby’s school.

Toby was gentle too, he even caress my balls. “Toby, how do you know what to do?” I gasped as he was sucking me harder and harder.

He pulled off me and laughed. “You’re not the first person to give me head, but you’re the best, I’ve had. I’m just doing what I like done to me.” MMMmmm I’m not the first he has had, well that is a discussion for later. I did warn him that I was about to cum but Toby didn’t lift off. I didn’t think he ever had anyone cum in his mouth and I found out when he started gagging.

“Are you okay. Babe?”

“Yeah, I didn’t realize what it would be like.” Toby was still coughing a little.

“It’s okay. Babe. You will get used to it.” I pulled him up to lay with me on the bed and we kissed and he held me tight. I felt safe with Toby, I never have with any of my other boyfriends. “So babe, who else have you been getting head from?”

“Just a few girlfriends when I was sixteen. It was before Jessica, I made out with them but I just never really felt connected to them.”

“How were you able to get it up, if you didn’t feel connected?”

Toby laughed. “We were double dating, so one of my buddies were always in the room with their girlfriend.”

I laughed. “You’re terrible, so you had to have another dick around.”

“Yeah and Jessica never wanted to make out when there was someone else around, so hence the reason, I was a killjoy.”

“So you learned to hide well.” He just nodded.

“Sometimes I think too well. I know I’m going to kill my family.”

“Well, let’s kill them much later. I want to teach you more before you have to go home. Unless you want to stay tonight.” I know it was too much to hope for.

“Why not.” He responded.

“Why not, what?”

Toby laughed, “You don’t follow your own thoughts.” Then he sat up and retrieved his pants and pulled his phone out. “Hey Dad, I’m going to stay at Jack’s tonight. Okay, I’ll be home by lunch, I promise. Thanks.” When he laid his phone on my nightstand I jumped on top of him and he laughed.

I was glad I decided to pick up condoms and lube, I’m going to take this night to a whole new level. Toby isn’t going to know what hit him. “Toby, can we try something tonight?”

“We can try anything you would like, Babe.” He kissed me.

I pushed him on his back. “I know you don’t know how to open me up, so I’ll do that. Would you like to make love?” He didn’t know but I own butt plugs and dildos, which I use quite a bit.

“I don’t know what to do, meaning…. Well really, I don’t know what to do.” Toby glanced away and I smiled.

“It’s okay, Baby. I do.” I got off the bed and went over to my dresser and pulled out the box of condoms and lube. His eyes widen “I didn’t think you would want to go bareback your first time.” I came back over and laid them next to him, he was already hard. “Toby have you ever measured yourself?”

He laughed. “Yeah.” I looked at him for the answer. “Just over seven.”

“There is no way.” And he laughed again.

“Just over eight.”

“And around?”

“I don’t know, I never grabbed my mom’s sewing tape measure.” He smiled.

“Yeah right.” I laughed.

“Almost five.”

I didn’t wait after he told me how thick he was, I was so horny. I rolled a condom on him and lubed him up, rubbing a lot of lube on me as well, pushing into me. I bent down and whispered into Toby’s ear. “I play with myself almost every night. I have a few dildo’s and I been waiting for this night to come.”

But I still wasn’t prepared for how big Toby is, I slowly pushed down onto his cock and I wanted to scream still, it hurt. He went to push up into me and I had to stop him. “DON’T, please let me guide this one.” He stopped, I know it was hard for him. “God Toby, you’re huge.”

I slowly rode him until it started to feel good to me. I knew he wasn’t going to last long, what guy does when they first start having sex. But I knew he would get it up a few more times tonight and I was planning on using that to my advantage.

When he started moaning, I knew he was going to cum. So I began rubbing myself, Toby was very sweet he tried to rub me, but he couldn’t focus so I took back over. I could feel his cock pulsating when he started cuming inside of me, which caused me to cum and I did all over Toby’s chest and stomach. I collapsed on him squishing my juices between us and he wrapped his arms around me.

We had such a great night, God we fucked so much, I was sore for a week afterwards but it didn’t stop me from having sex with him again and again.


Toby decided he wanted to be a cop like his father and brother Matt, so he went to community college while he waited until he was old enough to go into the police academy. Just before he entered, he decided to tell his family that he was gay. They have been wondering why he hasn’t wanted to date anyone and why I was still hanging around so much lately.

He didn’t want me to be there, which I hated but he let me wait down the street, I was in my car. I saw him walking my way and I got out and hugged him, he was already crying. I took him to my house, he was beside himself, his father told him to get out. I just held him, I didn’t know what else to do for him.

Bir yanıt yazın

E-posta adresiniz yayınlanmayacak. Gerekli alanlar * ile işaretlenmişlerdir

gaziantep escort bayan gaziantep bayan escort Casibom Onwin giriş Güvenilir Bahis Siteleri istanbul travesti istanbul travesti istanbul travesti ankara travesti Moda Melanj kuşadası escort bayan ankara escort escort escort escort travestileri travestileri beylikdüzü escort Escort artvin escort aydın escort balıkesir escort bartın escort batman escort bayburt escort bilecik escort bingöl escort bitlis escort bolu escort escort Antalya escort Escort bayan Escort bayan bahisu.com girisbahis.com antalya rus escort çankaya escort keçiören escort Escort ankara Ankara escort bayan Ankara rus escort Eryaman escort bayan Etlik escort bayan Ankara escort bayan Escort sincan Escort çankaya çankaya escort etiler escort beylikdüzü escort