Craigslist Experience #14

What the fuck? 

I read these ads on CL from you sub guys, and I just can't help myself. I'm not a mean guy. I'm not a bad guy, I don't like to see people in pain, but fuck, I've done it twice, and I think I kind of like it.

This was the CL post I responded to:

> Cum Slut that needs to Swallow !!!! - m4m - 51 (Salt Lake)
> Reply to: pers-XXXXXXX@craigslist.org
>
>
> 6'0 190 DECENT SHAPE LOOKING TO LEARN TO SWALLOW
> PROPERLY !!!!
>
> I WANT TO HAVE MY FIRST LOAD OF HOT CUM IN MY MOUTH !!
> I WOULD LIKE TO BE TRAINED to DEEP
> THROAT!!
>
> DISCRETE, SQUEAKY CLEAN, PROFESSIONAL!!!!
>
>

We e-mailed back and forth trying to set up a time. He hit me back with this.

>Are you interested in the dominant role as I want to
>be submissive and be told and
>taught what to do.
>
>I am looking fro an occasional hookup to let you
>drain your load and teach me to take it all properly!

I told him I'd give it a shot, and we made an appointment for Friday.

He showed up, pretty early in the morning as we had arranged. He drove a big black Caddy Escalade. He looked like the squeaky clean professional he had described.

I invited him in I and sat down on the couch. He looked a little nervous, and started to unbutton his shirt.

"Wait" I ordered. "I'll tell you, when to do that".

It was like the color drained from his face. He looked at me quickly, then bashfully at the floor and calmly said "yes Sir."

I motioned for him to turn around so I could give him the once over. (I didn't really know what I was doing.)  He turned around for me.

Then I told him to come over to me and rub my dick through my pants to get me hard. Each request was met with a submissive "yes Sir".

I took off my shirt, and told him to undo my pants. He did and he pulled them down. he went for the boxers.

"I didn't tell you to take of my boxers!" I kind of yelled. His arms went limp and his eyes fell to the floor. "Yes Sir" he said. I had him take off his shoes, shirt and pants.

I told him I wanted him to go into my bathroom. There, he would find something hanging on the shower rod. He was to put it on and return to the living room.

Yesterday I went to Family Dollar a store that sells all kinds of stuff, kind of like an even cheaper version of K-mart, and for a few bucks, bought a cheap panty and bra set. It was navy blue and had a little lace on it. God, it was embarrassing waiting at the cash register while paying for that!

Squeaky came out wearing the panties and bra. I told him to stand in front of me and model. He looked a bit humiliated. I hoped he was enjoying it.

I pulled down his blue panties a little bit and played with his dick for awhile, then teased him with my cock. "Lick the tip." "Kiss the head" Finally I let him start sucking me off, which I wanted so badly, but I pretended I didn't, just to further the game.

At one point I told him to go and stand in the corner turn his back to me and jack off, while I looked at porn. "Yes, Sir."

When I was ready, he couldn't wait to get back on my cock.

He was dripping with precum, and a stringy drop fell onto the blanket I had put on the floor at my feet. I figured this was as good as an excuse as any to swat Squeeky's ass.

"God Dammit!" I exclaimed, "you got precum on my blanket. Get over here and lay across my lap!"

Squeeky looked confused, but finally figured out he had to climb on the couch next to me, and lay across my lap, my hard dick poking up into his belly, his poking me in the leg.

SMACK, SMACK, SMACK. Three open handed swats to his hairless bum. "Now get back on your knees and suck my cock!" I ordered.

He did as told.

Shit, I didn't know who I was any more. I NEVER talk to anyone like that.

Squeeky was on my cock only a minute or two, when I felt teeth.

This time I didn't say anything, but reached down and grabbed his hair, and pulled him off my cock. He looked at me with a questioning fear in his eyes.

"Get across my lap" I quietly but firmly said.

He did as he was told. This time, I didn't hear a "yes Sir."

You-SMACK-scraped-SMACK-my-SMACK-dick-SMACK-with-SMACK-your-SMACK-teeth!

His ass was turning kind of pink.

"Now get back down there and suck my cock, and no more teeth!" I commanded.

"Yes Sir" he said in his meek submissive voice.

Taking a cue from the first guy that wanted to be submissive, I pushed his head way down on my cock a few times, until I could sense he was gagging, then I let him off. He never wavered and just kept sucking. Then I grabbed him by the ears and pulled his face up next to mine, and I whispered loudly into his ear:

"Now, I want you to jack your self off while you're sucking me. I know you're horny you dirty fucker, because you're dripping pre cum all over my blanket. I want you to get close to cumming, but you better not cum, fucker. Just keep you self on the edge, and when I get close, I want you to get your self off at the same time. Understand?"

"Yes, Sir" he hurriedly said, and then got quickly back on my cock.

He did just as I told him to do. He would jack his dick, then quit, sucking me off all the while. Finally, I felt my orgasm building, and I had to concentrate. I was alternately watching the twink porn playing on the TV and Squeaky working on my dick. Finally I was getting close, and told him.

He started sucking me with fervor, and jacking off himself as well.

I started moaning and my hips were involuntarily pumping and I started to squirt my cum into his hot mouth. It felt great.

At the height of my orgasm, he must have started to blow too, he kind of forgot his place, and started to bite down on my cock as he was cumming.

"DON'T YOU FUCKING BITE ME! DON'T YOU FUCKING BITE ME!!  I was able to yell.

He opened up his jaw and relieved the pressure, and he was whimpering as he furiously jacked his cock, just below my line of sight. He fucking squirted bucket loads all over the navy blue blanket that I had laid out for him. Good boy.

When he was though I could tell he had my cum in his mouth and he looked up at me. I handed him a terry towel, and told him he could spit. He did. I really can't blame him. Then I handed him a piece of gum.

"Wow, you think of everything" he said. (what happened to "yes. sir?")

I try.

He asked if he could shower. "Sure," I said, "but you're leaving your expensive Tommy Hilfinger boxers here, and you're wearing those blue panties under your clothes when you leave."

He came out of the bathroom after his shower. He had on the panties, but not the bra. He dressed and made some small talk, asking me about my house and stuff. I guess the game was over, because he acted just like an old friend, not like someone who's ass I had just spanked.

I've been using his boxers for a cum rag for awile, and they're getting kind of crusty.

He e-mailed back once and asked if he could come over again. I responded back, but I never heard from him again.

If he does come over again, he'll get similar treatment, but he'll go home with those crusty boxers on under his clothes!