Craigslist Hookup Pt. 02

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Things were going well at the law firm. I had been winning most of my cases and was getting a reputation around the local courts as “a force to be reckoned with” as one of the senior partners put it.

“In fact,” he told me one day, “you keep going like this you could even be a judge some day.”

“Really?” I asked.

“Why not? But in the mean time I need you to go to Chicago again for the Davidson case. Rumor has it that the defense has a surprise witness they’re going to present and we need to find out if Ted knows who it could be.”

I wasn’t too thrilled with the idea until I remembered the last time I was there. Will. I hid my excitement at the thought.

I had held on to our e-mails. I’m not exactly sure why. Maybe as a souvenir of our encounter. When the date I was going to be there had been confirmed I pulled up the last one and sent him a reply:

“Hey. I’ll be in town again the 19th and 20th. You interested in getting together again?”

My hands were shaking as I hit “SEND”. Would he reply? Did I even really want him to? A couple of days later I received a response:

“I think I can arrange to be free that night. Send me your motel info as soon as you get it.”

“Will do,” I excitedly answered. As I stood to go I glanced down at my crotch. Great, I thought. Am I going to be hard for the next week?


There was a knock at the door. I practically leapt from the bed and looked through the peephole.

“Hi. Come on in.”

“Hey. I was really surprised to hear from you again.”

“Hopefully pleasantly.”


We sat and chatted for a while. Kind of caught up on things. I think just getting more relaxed with other. Which was weird. We both knew the reason we were there. It’s not like we were on a date and hoping we would get lucky.

“Well,” I finally said. “What did you have in mind for tonight.”

“Actually, I thought we might try something a little different. My wife likes it a little but mostly does it because it really turns me on.”

“Maybe. What is it?”

He stood up and looked around the room. After a few seconds his eyes fell on a picture on the wall. It was a generic looking seascape that was probably in every room in the motel.

“Let’s just say your safe word is ‘lighthouse’”.

“Safe word? I don’t know about this.”

“Don’t worry, it’s not really all that different from last time. Besides,” he said, standing. “You wouldn’t need to worry if you hadn’t scratched my car.”

I was confused. “Scratched your car?”

“Yeah. It’s going to cost $500.00 to get it fixed.”

“$500.00? But I don’t have that kind of money”

“Well you’re going to have to figure out something. I’m not going to pay for it myself.”

“But I can’t. I don’t have any money.”

“I suppose there is an agreement we could work out.”

I acted relieved. “Sure. Anything. What is it?”

“Well,” he said, unzipping his pants, “there’s a girl I know who charges $100.00 for a blow job. I figure five should pretty much cover it.”

“But I’ve never done anything like that. I couldn’t.”

“I don’t really think you have a choice.” He pulled out his cock. “The sooner you get started, and the better casino oyna you do, the sooner it will be over with. Now get over here and get on your knees.”

Once I was in position he pulled my head towards his crotch.

“Now open wide.”

I resisted. But not much. “No. Please don’t do this to me.”

“Quit whining, you little bitch. You’re only going to make this take longer.”

I opened my mouth and he pressed his cock in.

“That’s it. Now start sucking.”

I slowly moved my head up and down on his hard shaft.

“That’s it. Suck my dick. That’s it. See, that’s not so bad. You might even learn to like it if I let you do it enough.”

“No. Please stop. Please don’t make me do this.”

“Shut the fuck up.”

As I knelt there with his big cock in my mouth, it was all I could do to keep from grabbing my own. I tried to keep in character. Resisting when I could and muttering the occasional “Stop” or “Don’t do this” but I don’t know how convincing I sounded. By the way he was responding I must have been doing pretty good.

Once I tried dragging my teeth along the shaft like I did the last time we were together. He seemed to like it then but he moved wrong this time and something caught.

“Ow! What was that?”

He pulled out of my mouth and examined himself for any damage.

“Did you try and bite me, you fucking cunt?”


He hit me with his cock. Hard. In fact, it actually did hurt some.

“I think you did.”

He hit me again.

“No,” I pleaded. “I didn’t.”

“Say you’re sorry.”



“I’m sorry.”


“Louder, bitch! I can’t hear you.”

“I’m sorry. Please.”

“That’s better. You better not let that happen again. Now ask for it back in you mouth.”

“Please,” I asked. “Please let me suck your cock some more.”

“See,” he said, “I knew you’d learn to like it. You can suck it.”

He let me enjoy him a little longer then said, “I think it’s time to finish this.”

He took my head in his hands and held it firmly. “I’m going to fuck your mouth.”

I tried to turn away but was unable to move. And this time I really couldn’t. He was holding me so hard I couldn’t move. Will was completely in control of me. I became even more excited, which I thought wasn’t possible.

We stayed like that for quite a while. Me on my knees and him fucking my mouth. Using me entirely for his own pleasure. At this point I honestly don’t know if he remembered, or even cared, who I was.

Breathing hard, he pulled out and grabbed his cock.

“Open, bitch! Open your fucking mouth.”

I obediently responded but tried to turn away.

“That’s it, you bitch. You’re finally learning. Now fucking stay there. Stay right there while I jack off in your mouth. Don’t fucking move. And you better swallow it. All of it. Or you’re going to do this again.”

“I will. I’ll swallow all your cum. I promise.”

He was pumping harder now. His knuckles turning white as he squeezed his cock.

“You fucking better,” he said. “You better swallow every fucking drop. Get ready. Get ready. Here it comes. I’m going to come in your mouth. In your little fucking bitch mouth. Here canlı casino it comes. Here it fucking comesssssss!”

His cock exploded into my mouth and on my face. His warm liquid splashed across my cheeks and onto my forehead. As much as was covering me, even more went into my mouth and ran down my chin. When he finally let go of his cock I quickly leaned forward and took him back in my mouth. Squeezing it with my lips to pull out the little that remained.

“Fuck,” he panted. “That was great. I hope it didn’t freak you out or anything.”

“No way. It was really hot.” I wiped some of his cum off of my face and licked my fingers. Not as good as straight from the source but still pretty good.

I didn’t realize how much I had liked it until I looked down. My own cock was rock hard and there was precum on the carpet. He was done but I still needed more. A lot more. I don’t think I had ever been this horny. I stood up.

“Fuck me.”

“What?” he said, sounding shocked.

“I want you to fuck me. Right now.”

“Are you sure?”

“Yes,” I said. I could hardly believe what I said next: “Please.”

“Take off your clothes,” he said. “And get on your hands and knees.”

Excitedly, I stripped. He started to do the same.

“No,” I said. “Leave them on. I want the same guy who was just here.”

“Yeah. I can see that. Only you want it this time, don’t you? You fucking slut.”

“Yes. Please. I want you to fuck me.”

“Then get down on all fours. Good. Now show me where you want it.”

I pulled my cheeks open for him.


He dropped out of character. For only a second. “Shit. I almost forgot. We’re going to need something.”

Back in character now. “Don’t move, bitch.”

He ran into the bathroom and came out with the hotel hand lotion, which he quickly rubbed over his cock.

He pressed the head of his cock against my ass and gently started pushing. I relaxed as best as I could and soon felt him slid inside me. But just the head.

“Let me know if it hurts or anything,” he whispered.

I nodded. “Keep going.”

He slid in further.

“You like that, bitch? You like how my cock feels in your ass?


“You want some more?”


Another couple inches went in.


It hurt a little but I was pretty sure I could handle him.

“Yes. Give me all of it. I want your whole cock inside me.”

He held me by the waist and pushed forward. I felt the last few inches of his cock enter me. Slowly but firmly he fucked my hungry ass, sliding back until only his head remained inside me then pushing in the whole length. With each stroke it became easier to take him in and before long it felt as good to me as it did to him.

“Yeah. You like that, don’t you, you little slut. I can tell you like getting your ass fucked.”

“Mmmm hmmmm,” I moaned. “I love it. Don’t stop. Please.”

“Don’t worry. I’m not going to. There’s no way you can make me stop. I’m going to fuck you hard, bitch.” He started pumping me harder, talking between his thrusts. “I’m going to…fuck your ass…and there’s nothing…you can fucking…do…about…it.”

“Believe me…I don’t want you…to kaçak casino stop… I want you…To make me your whore… I want you…to fuck me like I…deserve… Use my ass…for your pleasure… Fuck me…Fuck me in the ass.”

After far too short of a time he started going faster. I could tell he needed to finish.

“Stop a second,” I managed to say. “Take it out.”

He pulled out. “What’s wrong?

“Nothing,” I said, rolling onto my back. “I want to watch you.”

He spread my legs and pushed himself back inside. It went in easier this time.

“Mmmmmmmmmmm, I moaned.

I lay there on my back and watched him as he fucked my ass. Faster and harder. I sat up as much as I could, took his own ass in my hands, and pulled him into me.

“Fuck me,” I said, looking into his eyes. “Please. Fuck me. Harder. Fuck me harder.”

He pounded into me as hard as he could, slamming his body against mine. Filling me with his cock.

I arched my back and grabbed the bed in my tight fists. Grunting like an animal as he slammed into me. Looking back on it I’m sure it there was anyone in the next room they could hear us but at the time I didn’t even think about it. I wouldn’t have cared anyway.

“Don’t pull out. I want you to come inside me. Come in my ass.”

A few more thrusts and he came, moaning. He slammed into me until he was finished, then stopped, breathing hard. He started to pull out but I stopped him.

“Not yet,” I said, pulling him back and grabbing my cock.

A few tugs later and I came, shooting on my chest and stomach.

Will fell back to the floor, exhausted. After a few minutes he got up, undressed, and headed to the bathroom. “I need a shower after that.” We both did.

When I could walk again I followed him. I pulled the curtain aside and stood looking at him.

“Like some company?”


I stepped in next to him. The closeness of our bodies soon had us aroused again. I looked down at him.

“Three times? You sure you can?”

“I think so. Just don’t expect too much.”

We were both at that where we could only finish ourselves off and were soon jacking off like a couple of schoolkids. I finished sooner that he did. He finished in my mouth.

We got out of the shower, dried off, and he got dressed to leave.

I had never felt this way so, curious, (and worried?) I asked him.

“Are we gay?”

“Nah,” he said. “Just gay for each other.”

That sounded about right. Before he zipped up I walked over to him.

“Just a second,” I said, kneeling.

“There’s no way I’m going to be able to do any more.”

“Don’t worry,” I smiled. “You don’t have to.”

I pulled out his cock and, like last time, looked up at him as I kissed it.

“Thank you.”


A few weeks later my wife and I had just finished watching the latest episode of Game of Thrones.

“I think I’m ready for bed.”

I looked at my watch. it was only 10:00.

“It’s still a little early, don’t you think?”

“Oh, I didn’t say I was ready to go to sleep,” she grinned.

I followed her into the bedroom and paused at the doorway.

“What do you say we try something a little different tonight.”

“Different? Like what?”

I thought for a few seconds.

“Let’s just say your safe word is ‘Westeros.’”


I’m planning on a Part 3 but still have to work out a few details. Stay tuned.

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