Always Read the Fine Print

Work had been hell; working overtime running seven projects at the same time was very stressful. When it came to the end I decided to relieve some of my stress so I started searching the escort ads for a mistress. I was looking for specific fetishes and wanted to find a mistress who respected what I wanted.

I contacted several and finally found a winner. I wanted a massage to start, then a spanking, with dominance and body worship, ending with fucking so I could get some relief. I told her I don't like feet and my nipples are very sensitive so no pinching. She mentioned that she liked anal sex so I decided to bring some toys and lube.

When I play I like two safe words; RED is for stop and YELLOW is to move on or slow down, just to get out of character for a minute but to continue the play. I was looking for a slow role play so I was prepared to pay extra over the usual rate.

This is my story.

I was nervous arriving at her house, not sure if this is what I wanted but we agreed on the safe words and my limits so I felt assured all would go well. She was looking good when she greeted me at the door. She did the usual check and I grabbed her ass for my check, after placing the donation on the table we relaxed. She went over my conditions and limits again, and then we got down to business.

I needed a massage to relax so after undressing and laying down she started the rub down. It was very nice and loosened me up. When her hands were around my genitals she would tease my testicles and cock with her fingers, I liked that a lot. Occasionally her fingers would rub my asshole stopping to press down causing me to moan or even yelp out loud.

"Shut up and enjoy your massage!" she would say and then slap my ass.

"I need different oil" she said as she grabbed my bag of toys. She worked on my genitals, one hand massaging and tickling my testicles and cock, the other massaging my asshole with the new oil which didn't feel like massage oil but more like lube, little did I know that I was correct. As she oiled my ass I was moaning with the occasional yelp resulting in my ass being smacked. I felt the tip of a toy at the entrance of my asshole.

"Wait a minute, we didn't agree to this! I'm not gay! I don't want anything up my ass!"

I let out a big groan when she inserted a toy with small beads into my asshole.

"Shut up and enjoy it in your pussy." I was too worked up to fully comprehend what she had said, but she definitely called it my pussy.

"What did you say?" I asked her

"Just relax and enjoy it." She replied. I had brought the toys to insert into her ass. But I started to enjoy it and I was open to something new as long as we played with the small beads. She would keep hitting a spot in my ass that caused me to moan.

"That's your boy button. I don't know why they call it that because if I keep hitting it you will cum like a girl." She said as she continued fucking my ass with the toy.

"What do you mean?" I groaned

"You will cum just like a girl. Just from me fucking you, I won't have to touch your cock." Laughing as she replied.

"No, please I'm a guy!" I cried out and she just laughed

"We will see about that." She said as she was fucking my asshole with the vibrating beads while her other hand tickled my testicles and cock. When she pulled the toy out I thought she was done but then she grabbed the larger beads.

"No! Please don't! Please, I'm begging you! Don't fuck me with that!!!!" I let out a high shriek when the tip of the beads pushed its way past my outer ring and into my ass.

"Take it out! That really hurts! I don't like this, please stop! It's too big!" I cried out.

"The massage is over and you need to be taught to obey!" She told me as she smacked my ass even harder. She removed the beads and inserted a small butt plug which stayed in place.

"This plug will stretch you and prepare your pussy for later." She said with excitement in her voice.

"Why do you keep calling my asshole a pussy?" I asked, she responded with a hard smack on my ass.

"Stand up!" she commanded. I stood up covering my cock, being Irish I'm not well endowed. When I stood up I could feel the butt plug move in my ass causing me to reach behind me to remove it. She grabbed my hand.

"Leave it in place or I will find something bigger to shove up your pussy." She yelled out.

"Remove your hand and stop covering your cock." She commanded, and then she saw my cock.

"My mistake, I mean your clit." she said sarcastically. I was humiliated and confused, I'm a guy, and I don't have a pussy or a clit. She sat down and pulled me by my cock over to her. She made me lay over her lap for some over the knee spankings.

"You need to be punished for stopping me from fucking your pussy with the toy." She told me.

Again she said pussy and I was about to ask her what she meant when her hand came down on my ass spanking me. Many smacks later I knew my white ass was now pink or even red, she paused rubbing my ass feeling the heat radiating off my ass from her spanks.

"I will stop spanking you if you let me play with your pussy." as she moved the butt plug as if it was a joystick. I struggled a bit but she had a firm hold on me.

"But I don't have a pussy, I'm not a girl!" I cried out. That comment resulted in many more smacks on my ass, when she would spank me on the butt plug it drove in deeper causing me to cry out.

"Shut up! Or I will give you something that will really make you cry." She mocked me when I cried.

"Please stop spanking me." I begged her. She paused again rubbing my ass feeling the heat radiating off my ass from her spanking. Also she was moving the butt plug around in my ass.

"I will stop spanking you if you let me play with your pussy." as she moved the butt plug as if it was a joystick, also pulling and pushing it in and out. I knew what she wanted but I didn't know why.

I paused for a little too long so she slapped my balls causing me to cry out.

"I can do this all day long." She said.

"I don't have a pussy, I'm here to fuck your pussy." I cried out. My comment resulted in more spankings, now I knew my ass was red.

She pushed me off her lap and bent me over her bed; I had brought a rope restraint so she tied my hands behind my back. While I was tied up, the rope did allow me free myself if needed. She held me down with one hand and she grabbed the butt plug with her other hand yanking it out of my asshole as I cried out. She grabbed the lube, lubed the larger vibrating beads, and started fucking my asshole with them holding me down with her free hand. She hit the on button and vibrations started causing me to moan.

"That's your boy button again. Let's see if you can cum like a girl. Moaning like a girl means you must like your pussy being fucked!" as she laughed at my humiliation.

"I'm not a girl! Please stop!" I was saying as I tried to defend my manhood. She just laughed and continued fucking the toy in and out of my ass.

"Your pussy is so pretty, you should thank me for stretching your pussy." She commented while fucking me with the beads.

"I'm a guy; I told you I don't have a pussy". I told her when I could catch my breath. She just smacked my ass and laughed. I was about to say YELLOW when she stopped leaving the beads buried deep in me. I lay over the bed with the vibrating beads buried in my ass.

I didn't know what she was doing. But I soon found out that she had gotten a bigger butt plug. She pulled the beads out of my ass then she pushed the large butt plug into my ass which really made me cry. She twisted it while moving it in and out, stretching my asshole. I was about to say YELLOW again when she stopped.

"It's time for body worship but if you want to see me naked you have to keep the butt plug in to stretch your pussy." She said. She really liked calling my asshole my pussy.

She pulled me off the bed and had me sit on the floor with my back against the bed with my hands tied behind me; I winced as the butt plug went deeper into my ass.

"Did that hurt your pussy?" She laughed.

"Yes, but I don't have a pussy." I said as I shook my head.

"Kiss my ass!" She told me as she turned around, bent over, and lowered her panties. I started kissing her ass all over.

"Now you have to lick my asshole before we do any ass fucking" she told me, so of course I was happy to oblige. After licking her asshole she stood up.

"Are you ready to fuck?" She asked, of course I was ready!

"Yes but I want to remove the butt plug first." I replied happy to move onto the next phase.

"Of course silly, how else would I be able to fuck you?" She asked as she turned around, pulled down her panties and her giant cock popped out! I was like a frozen deer in headlights as I stared at her cock and balls dangling before my face. It was twice the size of mine! I finally regained my composure.

"This is a mistake, I want to leave!" I cried out and tried to get up from the floor. With my hands tied behind my back it was difficult to get up. Then to make matters worse she put her hand on my head holding me down.

"Open your mouth baby girl." She said as she started rubbing her cock over my lips.

I wouldn't dare because I knew what would happen so she started slapping my face with her cock. She would alternate between being nice and being mean saying things like; "Just give it a little lick, maybe you will like the taste" and "Open bitch, you are not leaving here without sucking my cock".

"Listen, if you don't suck my cock I'm going to bend you over the bed and fuck your pussy!' She told me.

"Please, No!" I begged

"Open up!" Was her reply; at first I just stuck out my tongue to taste her cock head. She was okay with that at first but after a while she got tired of that.

"Open up for some sucking." She commanded.

"Please, I'm not gay" I cried, but she just laughed.

"Good, I like fucking straight guys because I like to turn them out. It's no fun fucking gay guys that want my cock!" She told me and slapped me again. I cried out giving her the opportunity to stick her cock into my mouth.

"Don't bite me or I will really hurt you." She warned me. I have a really sensitive gag reflex and she noticed it right away. I think she was disappointed she couldn't go deep in my mouth.

"It's okay, there is no gag reflex in your pussy!" she said, that scared me so I wanted to do a good job and make her cum. She told me how to suck and lick her cock and balls, teaching me what she liked. This seemed to go on forever when she got tired of squatting and told me to get up on the bed to suck her. She sat up at the head of the bed.

"Get between my legs and start sucking again bitch!" She commanded, I removed the rope restraints so I could balance myself and also used one hand to help pleasure her. I have always been very oral and even though this was new to me I was starting to enjoy it. As I started sucking her cock again she reached for the butt plug to start playing with it again causing me to squirm. I moaned and went to pull my mouth off her cock.

"Don't stop bitch!" She yelled, the humiliating comments she made turned me on. Finally after a little while she pulled me off her cock.

"It's time to fuck!" She said as I stopped sucking.

"What do you mean?" I asked, knowing I didn't want to know the answer.

"It is time to fuck your pussy!" She laughed.

"Please let me finish sucking your cock." I begged but she just laughed as she got up.

"Lie down on the bed." She told me as she straddled my legs playing with the butt plug loosening my asshole. I heard her open a condom, put it on her cock, and then she grabbed the lube. She pulled out the butt plug, poured lube on it and shoved it back into my ass twisting it around. I cried out and she slapped my ass.

"This is going to be fun. I love to fuck straight guys in their pussy." She told me.

"But I don't have a pussy" I said and she just laughed.

"Sure you do." Was her reply as she yanked out the butt plug. When she was all lubed up she started to stick her cock into my asshole, it was too big and it hurt. I cried out for her to stop but she kept pushing in. I tried to push her out but that only helped her gain entry.

"Please take it out, it's too big!" I cried but she kept pushing.

"I told you I love to turn out straight guys." She said as she was calling me a bitch and other names, she was very verbal and demeaning. She slid all of the way in. Her cock was buried in my ass. I felt every inch of her cock as she rested for a minute to let me get use to her big cock. Then she started fucking me.

I begged her to stop; groaning and crying out as her big cock fucked in and out of my asshole. She would just laugh and call me names telling me I was being turned out.

"Now you are a girl since you know what it feels like to get fucked." I just moaned, burying my head in the bed. Then I remembered the safe words!

"YELLOW, stop fucking me!" I cried out. Finally this nightmare would be over! She did stop; but the problem was that she stopped with her cock buried balls deep in my ass, her laying on my back, and her arms holding me tight. I could feel her cock twitching in my ass as I struggled to get free.

"I said YELLOW, stop fucking me" I cried out.

"I did stop; I'm not fucking you anymore." She said as she laughed. Now it was just semantics because her cock was still buried in my ass.

"Please pull your cock out!" I cried.

"That would mean not stopping. Please make up your mind!" She told me.

As I struggled I could feel her cock hit places in my ass that felt good but I was afraid to admit that. But each time I squirmed I would softly moan in pleasure.

"That's your boy button again" she whispered in my ear as she teased me. She was no longer mean with her words but being sexy.

"I like your pussy, it's so tight. I know you like my cock in your pussy." I kept denying it but it did feel good.

"Do you really want me to stop?" She finally asked me.

"YELLOW, please fuck me slow and let me get use to it." I replied breathlessly.

"You have to tell me exactly what you want me to do." She responded, just teasing me. I was squirming and her cock was driving me crazy so I couldn't think straight.

"I want you to fuck me slowly and let me get use to it." I said again.

"Tell me what you want me to fuck." She whispered in my ear while holding me.

"My ass" I said.

"Wrong! Tell me what you want me to fuck." She replied, as she shifted causing her cock to move in my asshole causing me to moan.

"Tell me bitch!" she said louder.

"Please fuck my pussy with your cock." I said broken and beaten.

"I knew you would like it." She laughed. She fucked me flat on the bed for a while longer, and then she pulled out.

"It's time for some real fucking bitch." She told me as she pulled me up on to all fours doggy style.

"Now you are a bitch, just like a female dog". She told me; then she started fucking me opening up new places deeper in my ass. I was moaning and begging her to stop but she didn't care as she continued to fuck me. We changed positions several times while fucking as she continued to call me names and humiliating me.

Finally at the end she pulled out, ripped off her condom and shot her load all over me. She let clean up. As I came out of the bathroom she was standing by the bed.

"Bend over the bed again." She commanded. I groaned but obeyed her wishes. She yanked down my underwear and I felt her insert the butt plug up my ass and then she spanked me again.

"Don't take it out until you get home." She told me as she pulled up my underwear trapping the butt plug inside my ass.

"Please no more." I cried.

"Get dressed and you better come back soon so I can enjoy that pussy again." She responded.

It was going to be a long drive home...