Tom Gets a Second Chance

This is part of an ongoing story over multiple Categories with common characters.

*

I went to Cup in Time for my usual doppio with a shot of Carolans. Scott was behind the bar but the girl at the front register I didn't recognize. When I got to the front of the line she said "Welcome to Cup in Time. What can I get for you?"

"Hello; can I get a doppio for here?" I replied.

She was a little hesitant and looked over at Scott and said "Doppio? Scott."

He came over and showed her where it was on the register. Scott looked at me and said "Morning Tom. This is Crystal, she's new. Crystal, this is Tom. He's pretty regular here."

Crystal smiled and said "Hi Tom. It's my second day so I'm still learning."

"No worries, glad to meet you," I said as I handed her my card. As she rung me up Scott smiled and went back to the bar. After I paid, I went over to the bar and waited for my drink.

"Tall Mocha for Izzy," Scott said. As the lady took her drink and left, he asked me "Have you been to the new place yet?"

"Nah; not yet." I replied. Truthfully, I had forgotten that Jason was opening a second store on the south side of town. "Debbie there?"

Scott handed me my drink and nodded. "Yep, that's where she works now. Jason had to hire two newbies for here. Henry is in the back. He should be up here in a few minutes. Nice guy. Sad."

"What's sad?"

"Jason said no penis in the payroll," he replied.

I laughed and wanted to check this Henry out. "Nice guy?"

"Yeah, I've known him for a few years." Scott leaned in and whispered "In fact, we almost did it last year, but I was too scared. I wouldn't be now as you well know."

Henry came up from the back and said to Scott "I'm on now bud. Whatcha need?"

Scott stepped back and said "Henry, this is Tom. Regular here; always orders a doppio. Take care of him. Tom, this is Henry."

As Scott walked away Henry gave me a bit of a strange look then asked if I had lived here long. We chit chatted for a very short time as he made a drink or two. After a bit I said I'd see him again and went to a table.

Later, as I was drinking my doppio, Henry went to the table next to me and wiped it down. He looked at me and said, "Can I ask you a question?"

I looked over and replied, "Sure. What's up?"

"Do you know if there's an adult bookstore nearby?"

I looked at Henry and casually replied "Yeah, I think there's one near the lake."

Henry shook his head up and down and asked, "Ever been there before?"

Okay, where was this going? Well, I wanted to find out so said "Yeah. Why do you ask?"

Henry looked around and said softly "I think I owe you a blow job."

Okay, he had my attention. "What?"

Henry cleared his throat and continued. "I was there one day months ago and got a blowjob through a glory hole but panicked and took off after it was done. I was scared; it was my first time, so I went outside without giving one or talking to the guy that did it."

"So, what does this have to do with me?" I asked.

Henry looked around again and said "I waited outside and saw you leave the store. There wasn't anyone else in the store, so I figured it was you."

I didn't know what to say. Was this the guy I sucked at the bookstore that disappeared afterwards?

"I just want to apologize," he said. "And if it's okay with you I'd like to suck your cock to make us even."

Okay, this was crazy shit, but I could play along.

"Scott left yet?" I asked.

Henry gave me a confused look and said "Yeah."

"Does Crystal know how to make drinks?"

"Oh yeah, she worked at another coffee shop before."

"Good, then take me into the back-storage room and pull your cock out. I can tell if it was you or not."

"I can't do that," he replied a bit shocked at the suggestion.

"Sure, you can, I've been there many times. Just take me back there, I'll take a quick look then we can set up a time where you can make it up to me," I said. Well Henry, your call.

Henry looked around. The shop was pretty empty now, no one in line and only a couple of tables full. "C'mon. Let's make it quick." he said.

As we walked into the back Henry told Crystal "I'll be right back." We entered the storeroom and he shut the door.

"Lock it," I said. He did. "Show me your cock."

Henry unzipped his pants and pulled his cock out. I shook my head, "Nope, doesn't look familiar. Let me get a closer look." Before he could say no I dropped to my knees, grabbed his cock, and took it into my mouth.

"Oh shit!" he said as my mouth went down and his cock started to harden. He grabbed my shoulders as I went up and down with my mouth then pulled away. Smiling I stood up and said "Oh, yeah. I remember this nice cock."

"Fuck man!" he said loudly. "Are you crazy?"

"Relax man, this room gets used for cock sucking a lot," I said. "Now let's set up a time where we can get together at my place."

Henry put his cock away and zipped up and asked, "Your place?"

"Yeah, fuck the bookstore," I replied. "I want to be somewhere where we can take our time and have privacy."

Henry looked at me and it was his turn to not know what to say. I continued "You like sucking cock? You getting enough to suck, and you have enough guys sucking yours? Let me guess, probably not. Well today's your lucky day Henry. I can fix that. Now let's exchange phone numbers and we can set up a time."

He looked at me and smiled. Nodding his head up and down he said "You're right. This may be my lucky day."

We got back to the bar and Crystal looked at us and smiled. Wonder what she knew about if anything? Oh well.

************

The next morning, I was checking my website and filling orders when my phone went off.

Ding! Hmmm, Henry? Interesting.

Henry -- Hi Tom. How are you?

Me -- Doing well. What's up?

Him -- Well I was thinking about what you said yesterday. Want to get together?

Me -- Sure. When?

Him -- I have to be at work at 1 but am free now.

Me -- Cool. Come on over. Here's my address.

Him -- Be there in about ten.

Sure enough, he arrived with a minute to spare. Hmm, that was interesting.

"Good seeing you again Henry" I said as he came inside.

"Same here," he replied.

"Want something to drink? Water, beer, wine?" I asked.

"Kind of early for alcohol, how about water?" he said.

Kind of early for alcohol? Wait until you're about twenty years older kid and you'll be thinking differently. I learned after I got older, it's never too early for alcohol. I headed to the kitchen and came back with a bottle of water for Henry and a beer for me.

"Mind if I sit down?" Henry asked. Polite kid, I figured he was about Ben's age, maybe twenty something. This should be interesting. I know I can suck his cock, but bet I can't fuck his ass, at least not yet.

"Sure, have a seat."

We sat and talked for a bit then I figured he might be a bit inexperienced and didn't know what to say so I jumped right in.

"So Henry, when I sucked your cock at the bookstore, was it your first time with a guy?"

He paused for a bit then replied "No, I had had my dick sucked a couple of other times at the bookstore, but they weren't as good as when you did it. I mean uh, well you know."

"No, no, no," I said reassuringly with a smile. "It's all good. Just was curious about how far you've gone with this guy-guy thing."

"Well when you sucked me off it felt really, really good. That's why I stayed around to see who you were even after I ducked out. I was so scared."

"No worries. I remember the first time a good friend of mine sucked my cock and I sucked his. It was right here actually. Being friends before sucking his cock made it so much better."

Henry nodded and said, "I hated going to the bookstore but was too afraid to ask any of my friends. Except for one time but nothing came of it."

"So, Scott and you are still friends?" I asked.

Henry looked stunned and stammered. "Oh, the Scott at work? Yeah, that's how I got the job."

"Hey man, no judgment here. Scott told me about you two," I replied. "Scott and I are pretty close buds."

"He did?" Henry asked.

"Yep, said he regretted not going through with it. But it would have been his first time; first time is the hardest."

Henry was quiet for a couple of minutes then asked. "Do you and Scott; you know."

"Oh, do I suck Scott's cock? Oh yeah, as often as I can," I said. "I trust you to keep it a secret, but yeah we do each other a lot."

"Ever suck his dick in the storeroom at Cup in Time?"

I laughed, "No comment."

"I'd suck your dick there," Henry blurted out. "I mean, uh."

I laughed again. "Look Henry I have a lot of friends that I suck and suck me, and we have a good time. We like to say grownups doing grownup things. But each one of us had to be comfortable with doing it and we did it at our own speed. No one got tricked or pressured into it. Same thing with you."

"What do you mean?"

"I sucked your cock at the bookstore because I was good with it and wanted to do it," I said. "I was ready to do that and as I got ready to do other things, I started doing them. But the thing was; I was ready. You said you wanted to suck my cock, but are you ready? Have you sucked dick before?"

Henry shook his head and said "No. Actually you were the last time I had my cock sucked by a guy. The bookstore just didn't seem safe and I just figured I'd forget about it. Then I saw you."

"Well look, sucking a guy's cock is a big step in a man's life on a lot of levels," I said. "If you ever decide you want to do it, do it for the right reasons."

Henry nodded that he understood. I smiled and continued.

"You don't owe me anything; you don't have to suck my cock. I sucked yours because I wanted to, no other reason. Make sense?"

Henry smiled and said "Yeah, it does. Thanks for understanding Tom. I appreciate it."

"Good, now that we have that all cleared up, how about if I suck your cock? I'd like that."

Henry looked stunned; guess he didn't see that one coming.

"Look, I want to suck your cock and you don't have to suck mine. In fact, I have a few friends that I suck their cocks and they don't ever suck mine and we're good with that." Okay, so I was lying but I

did

want to suck Henry's cock. "If you don't want me to that's fine as well. Just saying."

Henry took a deep breath and asked, "Will you suck my cock Tom?"

"Only if you cum in my mouth Henry," I replied. "We can do it right here, right now. Get comfortable."

Henry stood up and began to unbuckle his pants. "Should I get naked or what?"

"Whatever you want to do, it's your call. I can do you here, in the kitchen, in my bedroom, whatever makes you comfortable. Naked, pants down around the ankles, take them off. That's up to you. I just want your cock in my mouth."

Henry pulled his pants and then his underwear down to his ankles, his cock starting to get hard.

"Comfy?"

"Yeah, yeah I'm good," he said.

"One thing you need to know. You can hold my shoulders but don't touch my head. I'll take care of you."

He was almost totally hard when I grabbed his cock. He flinched a bit then stood his ground as my wet hand slid up and down his cock. I bent forward and licked the head of his cock. It expanded in enthusiasm as I went around it to the left then to the right. My other hand went to his balls as I lifted his cock up and began to lick down towards the base.

"Ohhh damn," Henry said as I went farther down, down to his balls and began to lick them.

"Hmmm; better than at the bookstore, hey Henry?" I started to go back up.

"Oh yeah, way better," he replied. "Oh hell; that's so good."

Back at the top I opened wide and took his cock inside. He wasn't the biggest cock I sucked but it was a nice size. I could get it all into my mouth I figured and went down to see. Yep, it fit really well, like it belonged there. Of course, every cock I suck belongs there. I swallowed down to the bottom then came back up, wet, hot and slow. Henry had gripped my shoulders and he tightened his hold. Oh, I knew what that meant.

I went down, fast, then up fast. Over and over my mouth slid up and down his hard, fleshy cock. Halfway down I'd stop and swallow hard, his cock thick and tasty. Then down I went to the bottom of his now aching cock, all the while rubbing his balls. Back up halfway; swallow gripping his cock tightly, then back to the top.

This was his first really good blow job and he could see me sucking his cock. Glory holes are cool, but you can't tell who's on the other side sucking your cock. But when you can see the cocksucker? It becomes personal and I knew he was going to cum soon. He didn't disappoint.

"Oh shit! Oh fuck!" he yelled as he shot a huge, young spurt of cum into my mouth. I counted four large squirts and a couple of small ones then he was dry firing. Ahh, to be young and cum loaded again! I sucked him dry, wanted more, but instead I pulled away. He let go of my shoulders and backed away, finding the chair behind him and sat down.

"I'm, I'm sorry," he said.

"Sorry for what?" I asked after I had finished swallowing his yummy cum. Fuck, I love swallowing cum!

"I didn't last that long," he said.

"Oh man, I don't care! You shot a sweet large load of cum in my mouth," I said. "That's what I wanted, and you gave it to me."

"Oh, oh okay," he replied. "I didn't want to disappoint you."

"Henry; you didn't," I said. "I loved it and will suck your cock any place, any time. Just tell me when and where."

Henry looked at me and didn't know what to say. Geez, I love the young ones.

"I have a roomie this weekend, so you better get your pants back on in case she comes home."

"Okay," Henry said as he stood up and put his pants back into place. "I'll be going now."

"Oh, you can stay longer if you want, but if you have to be somewhere, I understand."

"Well actually I don't. It's okay if I stay here for a while?"

"Sure, put on the TV," I said and tossed him the remote.

"Thanks," he replied and began changing channels.

"Hey, I usually have some coffee at Cup in Time about now, but I'd rather stay here and shoot the shit with you. I'll make us a French Press and put some Carolans in it."

"Carolans?"

"It's a liqueur, you'll see."

As I started to walk to the kitchen Henry said, "Thanks again for sucking my cock."

"Loved it and I tell you what, if you ever want to suck mine, just let me know. If you don't, as long as I can suck yours, I'm good with it," I said.

Henry smiled and nodded. "We'll see," he said.

There was a knock at the door. I opened it up and Alexa stepped in, gave me a hug and a long kiss. When she pulled away, she noticed Henry and said "Oh, hello! You must be one of Tom's friends! I'm Alexa, glad to meet you."

Henry nodded and said, "I'm Henry, pleased to meet you."

Alexa and Henry did the chit chat then she told me she had a wonderful morning. She also said she was going to see Lori tonight for dinner.

"I'm sure you two will have a good time," I said.

"Three of us. We're having Cyndee for dinner too," she explained.

I laughed, "I bet you are. Sounds like fun."

"Well I have to give Edwin a call, so I'll see you in a bit," she said and headed off to my bedroom. I turned to talk to Henry, and he said softly.

"Holy shit! Is that your girlfriend? She's gorgeous."

I laughed and said "Not quite. She's a friend in from Vegas. But you're right, she is gorgeous. Sweet too."

Henry stood up and said "I have to be going Tom. Want to grab some food before I head to work. Thanks for everything and I'll think about what you said. I appreciate it."

I walked him to the door and after he left Alexa came into the living room.

"You have a good time sucking his cock?" she said with a grin. "I tasted it when I kissed you."

"Yeah I did," I replied. "Nice kid, he's a newbie, still struggling about sucking a cock."

"Well if he hangs around you long enough, you'll help him through it," she said knowingly. "Want your cock sucked?"

"How could I ever tell you no," I said as we walked into my bedroom.

************

"Ding" The timer went off in the kitchen and I went to fix up my coffee. As I topped off the cup of French Press with the Carolans I got a text.

Henry -- Morning Tom. Have some free time?

Me -- Sure. What works for you?

Him -- Now would be great but maybe this evening?

Me -- Now is fine.

There was a knock at the door. Huh? I went to it and it was Henry. He had a bottle of Carolans in his hand, a smile on his face, and asked, "Is your roommate here?"

Let's just say I was a bit surprised. I told him no, he had met Alexa yesterday, and motioned him inside. He walked in and I closed the door. When I turned around, he had placed the Carolans on the table and said, "I want to suck your cock."

"What?"

"I want to suck your cock," Henry said. "I thought about it all last night after yesterday and jacked off a couple of times while thinking of doing it."

I didn't know what to say. Was he sure? Did I care? I mean, he wants to suck my cock and I loved sucking his. What the fuck.

"Hold on a sec," I said as I grabbed my phone and texted Alexa. She stayed at Lori's last night and I didn't want her coming in and scaring Henry off. She didn't get back to me right away but hell, at least I tried. "Come on, let's get comfortable." I led him into the bedroom, closed the door and we got undressed. Yum, yum, yum. He was young, good looking, in shape and was hard already.

"How do you want me Henry?"

"Whatever works best for you," he replied. I sat back on the edge of the bed, my legs spread wide, cock hard and ready to go. "Oh, one more thing," he said with a grin. "Don't touch my head."

I laughed, he dropped to his knees and took my cock in his hand. "I been thinking about this all night," he said. "I hope I do it well."

"Don't worry about that Henry. Just do what feels natural to you and the more you do it, the better you'll be at it. Can I cum in your mouth?"

He looked me in the eyes and said, "You better," and went down on me.

Henry wrapped his mouth on the head of my cock and pulled his hand away. His mouth was hot, my cock was already aching, and he slowly went down my dick, stopping about halfway.

Once there he swallowed, his mouth tightening on my cock. After a second or two he relaxed and slid back up. Down he went again, this time taking a bit more of my cock inside him then he stopped and swallowed. He spent a little longer on my cock, slid a bit lower, not much and swallowed. I figured newbie had maxed out as he came back up my cock.

I know the first time a guy sucks a cock it usually isn't that great, but hey, he's sucking your cock! Henry went back down then back up, speeding up and down, a man on a mission and I wasn't going to disappoint him. I started to play with my hard nipples, my cock aching even more, wanting to fill this newbie with my cum.

"That's it Henry. Oh shit, that's good," I said. Encouraging him as he went along, he found his groove and it really was good. I was getting close as he pounded my cock up and down, up and down. After a few minutes I figured the newbie might be getting tired so I helped him along.

"Oh fuck, Henry," I said loudly. "I'm going to cum!"

I shot my first spurt into his mouth on the down stroke, he stopped a bit, then kept sucking. Up and down, two three spurts of hot cum splashed in his mouth. Was he going to swallow my cum? He answered that question as he kept sucking and sucking. After how many dry fires I pushed him away, totally spent.

Henry looked at me and smiled. "I liked that," he said nodding in agreement.

"You can suck my cock anytime you want my man, any fucking time," I replied. "As long as I can suck yours."

He laughed and stood up; cock hard. "Want to do it now?"

Did I want to suck his cock?

I always want to suck a cock!