A man in need of quick cash makes a deal he might regret.
I needed five hundred dollars quick. Like now. Nevermind why. A friend of a friend knew a way. It sounded simple. Go to the address provided, strip, blindfold myself, get on all fours, and wait for someone to show up and fuck my ass. He said the guy would wear a condom. He also said the guy liked my "type".
About my type. I'm athletic, but not chiseled. Taller than average. Dark hair and eyes. A bit of a tan. And I'm straight. I've never been with a guy or even thought about it. Hell I didn't even like when my ex girlfriend tried to stick her finger up my ass.
But it couldn't be that bad, could it? No one would have to know. It would only take a few minutes, right?
I showed up, opened the unlocked door, and walked in. An almost bare room. Bathroom in the right corner, a closet next to it. I stripped, put my clothes in the closet. Made a quick bathroom trip and put on the blindfold I had found in the closet, and assumed the "position".
Not sure if there was a cam in the hall or in the room, or maybe some sort of an alarm that was tripped, because I heard the door open almost instantly. Good thing, it didn't give me time for second thoughts or worry.
"Hey, baby", I heard him say as he entered. I heard a suitcase or bag being set on the floor and unzipped. He had a deep, soft voice. A bit seductive I'd have to admit.
"Hey", I replied.
"I like what I see so far", he said as he slapped my ass. I winced in spite of myself.
"Thanks", I replied.
I felt him straddle me, his jeans legs brushing against my sides. Then he started massaging my shoulders. It felt good. I was starting to get into it. Maybe this won't be so bad I thought. I think I even moaned a little.
Then I felt his hands around my throat. I started to get up and protest, but he held me in place and handcuffed me. I was getting scared and was too afraid to guess what else he had in his case.
"This wasn't part of the deal", I said.
"I don't make deals", he replied.
"I was told $500 to get my ass fucked with you wearing a condom. That was the deal!".
"Your ass, and everything else is mine for the next hour or two. We'll see if I wear a condom or not."
I started to protest again, but then he put a ball gag in my mouth.
"Just keep quiet and cooperate, baby. Then you won't get hurt... Much."
With that he started spanking my ass. I hadn't been spanked since I was a kid. I wouldn't even let my ex do that. Though it smarted, it felt good in a way. Made me feel like a bad boy. Made me moan.
"Oh, you like that , baby? Wait till you see what else I have for you."
I heard him rustling in his bag again. Next thing I knew he was putting clamps on my nipples. I did not like that at all! He sensed that and gave both clamped nipples a little twist.
"You'll learn to love it, baby."
Then he started massaging my shoulders again. It had a calming effect on me. I started moaning again. I could feel my cock stiffen. Was I going to enjoy this?
"Yeah, just relax, baby".
I was getting tired of being called "baby", but his voice was soothing and, I hate to admit it, erotic.
He worked his way down to my ass, massaging every inch. He then alternated massaging and spanking my cheeks. My cock was getting harder and my moaning increased. Then he began massaging my balls and lightly stroking my cock. I could barely stay still enough for him to continue. I wanted to cum so bad.
"I think you're going to really like this, baby."
By this time he could call me anything he wanted. I was writhing in pleasure.
I could hear him rustling in his bag again. What would it be this time? He went back to massaging my balls and then... He was hanging weights from my balls! I'd heard of it, but had never experienced it.
Before I could even begin to react, he started whipping my ass with a leather belt. The unexpected jumps from pleasure to pain and back were driving me crazy. I tried to scream around the ball gag.
"Shhh, baby. The real fun is about to begin."
Then he began massaging my ass again. It felt good after the belt. Then he licked my asshole a couple of times and spit on it. The licks felt really good. I still really wanted to cum.
I felt his cock head press against my asshole. Then it slowly began entering. It hurt as his cock entered my ass. At least he was taking it slow.
"Your asshole is so tight, baby. Feels so good on my cock."
I guess it took a minute or so for him to enter his full length. It didn't feel bad after the initial penetration. It took a moment to get used to the full feeling. And, yes, I began to like it.
Then he started slowly fucking me. I was really getting into it. Squirming and moaning.
"I told you you would like it, baby."
Just as he was picking up the tempo, I heard the door open again. My fucker paused briefly.
"She told me you would be here. You almost missed out on the fun."
"Wouldn't miss it for the world", another male voice replied. His voice was higher pitched and edgy. I didn't think I liked him.
I heard him move in front of me and then I heard a zipper. All of a sudden, an almost hard cock slapped me in the face. My earlier fear returned. I definitely didn't bargain for two guys.
Then he started brushing his cock head against my lips. I felt his balls on my blindfold.
"This would be more fun if he could see my balls coming", the second guy said.
"Oh, he's nothing but fun. The little bit of misbehaving at the start was worth it to feel his tight asshole grip my cock. Not sure how much longer I can hold out."
"Guess I need to put him to work then."
With that he parted my lips with his cockhead. I figured at this point there was no point in resisting. He worked his cock in and out of my mouth, going deeper with each thrust. Eventually I felt his cockhead in my throat and his balls on my chin. I gagged a bit.
"You're doing a good job, hon. You just need practice, it will get easier."
So now I'm one's "baby" and the other's "hon". At this point I was hoping and praying it was only these two.
At this point one was railing my ass and the other was fucking my face. It seemed to be a race to who would cum first. Then I realized I was tasting cock and not a condom, and come to think of it, it felt like a bare cock in my ass. I wasn't surprised by anything at this point, but I was hoping both were clean.
Then I heard the door open again. What now?
"What a filthy little slut!".
It was the voice of my ex! What the fuck was she doing here?
"You wouldn't let me put my finger in your ass, much less let me peg you. You wouldn't let us have threesomes. Now look at you!"
About this time both guys came. It felt nice in my ass, but I spit out the cum in my mouth.
"Make him clean it up!", I heard her scream.
The first guy pulled out of my ass and began spanking it. The other pushed my head down to the puddle on the floor. I began licking up the cum and swallowing, trying hard not to gag. The first guy was still pelting my ass.
"That's a good girl, baby", the first guy said. "Clean it up."
When I finished the first guy stuck his cock back in my mouth.
"Clean this too, baby", he said.
Then the other guy stuck his cock in my mouth. I cleaned his cock as well. My head was spinning at what I had done. I wasn't feeling well at all. I laid down on the floor.
"So we owe him 500 bucks, right?" the first guy asked.
"Cheap sluts like him are barely worth 20 bucks each", my ex replied.
I felt some money drop on my body as my hands were untied. I heard the door open and close.
When I took my blindfold off. I saw that I was alone and only had $40 to show for my ordeal. I began to cry.
Did she arrange this? Was it revenge?
I cleaned myself up as best I could and left. Then I started plotting my revenge...