Craigslist Hookup Pt. 03

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Life was good. I had just been made a senior partner at my law firm. In addition, we had opened an office in Chicago, which meant my meetings with Will soon became a regular thing. During the months we spent together we started growing close. Our “fuck sessions”, as we called them, were starting to include talking and we actually got to know each other beyond our purely sexual attraction. I didn’t know just how close we had gotten until one day in August.

Our meetings always started with me blowing Will. I wasn’t sure which of us enjoyed it more. I honestly think it was me. In addition to the purely physical aspect of it, I had the additional sensation of knowing I was pleasing him. I would often look up at him as he was coming. The expression of pure pleasure on his face thrilled me in ways I could never have imagined.

He never sucked me and I never fucked him, which was perfectly fine. It had never even occurred to me to suggest it. Although we had never discussed it we both early on accepted the fact that in our relationship he was the top and I was the bottom. Or maybe he was the man and I was the woman. It seemed perfectly natural for it to be that way.

We were in a motel, as usual. Both of us naked, him lying back with his hands behind his head, watching me blow him. Having him in that position always excited me. Some times I sat on his cock and rode gaziantep escort him like that, doing all the work while he relaxed. Once or twice, after having abstained for a while (my wife being ill or having her period) I almost came like that. It was the closest I had ever gotten to coming just from one of Will’s ass-fuckings.

“That’s it,” he was saying. “Suck my cock. Mmmmmm. Like that. You like sucking my cock, don’t you?

“I love it.”

“Yeah. Tell me all about it.”

By now, we both knew what each other liked. Will like the dirty talk. I didn’t mind it but it really got him off so I started stroking him.

“I love sucking your cock, Will. Your cock is so big. And hard. It feels so good in my mouth and I love when you let me suck it. And I love that you come in my mouth. Your cum tastes so good and you always give me so much of it.”

“And you always swallow it don’t you. Like a good little cocksucker. Because that’s what you are, isn’t it. A cocksucker.”

“Yes. I’m your cocksucker. I’m your little slut. I’ll suck your dick any time you tell me. I’ll drop to my knees and let you put your big, hard cock in my mouth and suck you off until you come. Until you come in my fucking mouth. I love being your cocksucker.”

“You like it in your ass too, don’t you, you fucking whore.”

“Yes. I love it when you fuck me in the ass. I love it when you make me get on my knees like the bitch that I am so you can fuck my ass with your hard cock. Are you going to fuck me today, lover? I really want you to. I want you to fuck my ass. Fuck it with your big dick. In fact, I don’t just want it, I need it. I need my ass fucked. Are you going to fuck my ass, baby?”


I could tell he was getting close to coming.

“I can’t take this any more. I need to suck you. Please le me suck your cock, Will. Please let me put it back in my mouth.”

“Suck it, BITCH!”

I grabbed his cock with my mouth. His first shot hit my cheek but the rest went inside. Squeezing, I milked his dick with my hand and lips, draining out his cum and swallowing it.

“Damn, that was good.”

Wiping his cum off my cheek and licking it from my fingers I looked up at him and smiled. “Glad you liked it.”

I laid there with my head on his stomach, stroking his cock. Waiting for it to wake up again. I could tell by his breathing that he had fallen asleep. I let him sleep until I couldn’t wait for him any longer. He had come once but I hadn’t and I was still hungry for him. I took him in my mouth and held him there, running my tongue over his cock. I could feel him getting hard in my mouth as he responded to me. Before long I heard him stirring and looked up.

“Good,” I said. “You’re awake.” He looked down at me and smiled.

“How could I not be after that?”

I got him wet with my tongue and climbed up next to him. He started to roll me on my stomach but I stopped him.


“What’s wrong?” he asked.

“Nothing. I just…”


I took a deep breath. “I love you.”

I don’t know why I said it right then. I only knew that it was true. I think I had known it for weeks.

“I don’t know how you feel and it’s okay if you don’t feel the same. I just wanted you to know.”

He didn’t say anything, he only smiled. Then did the last thing I expected. He pulled my head to his and kissed me. Firm but not hard. Then he laid me on my back and entered me. He moved slowly, gently. I lay on my back, looking up at him as he thrust into me. He positioned himself so that my cock was pinned between his body and mine. I ground against him, grabbing his ass and pulling him into me harder. As his passion overtook him he began moving faster. I arched my back and thrust my hard cock against his stomach. With a moan he slammed into me one final time and I felt his body shudder as his cock exploded in my ass. The feel of it made me come. We pressed our bodies together, using each other to drain our cocks. Finally, he rolled off and collapsed on the bed beside me. There in a motel room in downtown Chicago we did something we had never done before: We made love.


Stay tuned for Part 4.

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