Boy and Mistress

Normally, I didn't check my personal email at work. My boss said he didn't monitor communications, but I didn't trust him. It was a Friday night, my girlfriend was out of town, and I didn't have anything to do. I was feeling a little lonely and was hoping my girlfriend sent a message saying she missed me.

I scrolled down the inbox looking for her email address. Something else caught my eye. It was my mistress's email address. My lungs moved to my stomach and my stomach moved to my throat. I didn't think I was going to hear from her again. I messed up the last time I was with her.

I had the nerve to forget to turn off my cell phone. I recognized my girlfriend's ringtone, got off all fours, and answered the call. When I hung up, Mistress slapped me across my face. She cut a hole in the crotch of my jeans and sent me away. Fortunately, I was able to stop at the office to change into my spare suit before I went home to my girlfriend. I sent Mistress an apology but didn't hear from her for months.

I didn't know if it was going to be words of hate or the time for our next session. I felt somewhat confident when I saw very few words on the page. It meant she wasn't chastising me. It read, 'SATURDAY. 9AM. LAKE HOUSE. You were very naughty Boy. Mistress is not angry. Boy will have the chance to fulfill his ultimate fantasy. COME NAKED.'

Coming naked was the least of my concerns. Whenever our sessions took place at the lake house, I had to come naked. The house was in the woods so we had no worries. My only problem was she made me park on the street.

Saturday, everyone was out walking their dogs or pushing children in strollers. I had to sit in the car and wait until the coast was clear. I was several minutes late. Mistress punished by making love to me. There wasn't any cock torture or humiliation. She repeatedly told me I was the best she ever had. I lost my erection repeatedly. She tried to make me feel better instead of humiliating me. I learned to come early.

I left work and began preparation for Mistress. She wanted me to look as boyish as possible. It was hard to make a 41-year-old look like a boy. I didn't even look boyish when I was a teenager. I had always been muscular and suave looking. I pulled many older women when I was growing up.

I shaved off all my body hair. I hated the way it looked, but Mistress would always get what she wanted. Depending on the notice, I would try to lose a little weight to make me look skinny. I started to put on weight when I thought our arrangement ended. I would mess up my hair and usually wear sagging jeans and a wife beater to look like a punk instead of a businessman.

It was cold and raining that Saturday. I hoped we wouldn't be going into the lake because my dick would end up little and shriveled. Mistress would not be happy. I always had to bring myself to erection before I went to the house. People jogged past and I would temporarily stop jerkin my cock until I was satisfied I was alone.

When I was at my full length and hardness, I checked to make sure the coast was clear. I rushed past the front gate. From there on, I wasn't visible from the street. I walked casually the rest of the way. I held my cock while I walked so it wasn't bouncing around.

There was an unexpected note on her door. It said go straight to the boat. I had been on her boat only once. It was too large and too nice for the lake, but a welcomed change of scenery. From that point forward, I did not hold my cock in case Mistress was watching.

I climbed onto the observation deck and didn't see anyone. It was the first time I felt completely exposed. Cold rain hit me and a breeze made the water sting. My cock was completely erect and my hands were behind my back. I went down to the cabin and there was my mistress sitting naked on the couch.

I ran over to her with my hands behind my back. I got down on my knees and kissed her feet. "Thank you mistress. Thank you for inviting Boy back Mistress."

"Stand up," she said, jerking her feet away. "I'm glad you got my email. Good Boy. I said that you would be able to fulfill your fantasy. Does that sound good Boy?"

"Yes Mistress."

"What is Mistress' fantasy?"

"Mistress' fantasy is to see Boy fucked by other men."

"Good Boy. And what is Boy's fantasy?"

"Boy's fantasy is to see Boy's girlfriend dominated by Mistress."

"On your hands and knees." Mistress stood up and bent over to lift up the couch cushion. I got a spectacular view of her pussy and ass. There was a cane under the cushion. It was my least favorite device she used. She slowly walked behind me. My ass was in the air and my balls were a fair target. I could feel my cock begin to shrink.

I felt the sting of the cane on my ass. It was a light hit but still painful. "Mistress' fantasies are Boy's fantasies, right?"

"Yes Mistress."

"What is Boy's Fantasy?" She rubbed the tip of the cane on my balls. I wanted to be sure to get the question right so that she wouldn't hit my balls with the cane. Each hit was always harder than the last. Then I felt the tip of the cane follow the path from my ball sack to my asshole. She inserted the very tip of the cane into my asshole. I could barely feel it, but then I understood the question.

"Boy's fantasy is to be fucked by men." I had actually put that on the list of things I was unwilling to do when we made our arrangement.

"Today is Boy's lucky day." She removed the cane from my ass. On my hands and knees, I saw a pair of hairy legs come around the corner. I wasn't supposed to look up while I was on my hands and knees so my eyes stayed fixed on the legs and large feet. My stomach immediately dropped.

"Go topside Miguel," I heard Mistress say. The two legs walked past me. When I could no longer hear the footsteps, Mistress walked in front of me. "Stand up." I was almost ten inches taller than Mistress, but she could get me to do anything she wanted.

Mistress walked back to the couch and lifted the cushion. I could tell she had out the string. She stood in front of me and looked at me for several seconds. I saw her begin to smile and I was starting to feel good, thinking she was happy to see Boy.

Her hand smacked my face. It almost put me off balance. When I straightened up, she spit in my face. I opened my mouth just in case she had more. "Close your fucking mouth. Your fucking cock is barely hard." She reached down and started stroking my cock vigorously. I was immediately rock hard and realized how I missed her touch.

The string wrapped around my cock and balls several times. She pulled it so tight it felt as if it was cutting into my skin. My balls were bright read and the head of my cock turned purple. I hated the string. It pulled my cock down instead of letting it point up freely. She held on to the end of the rope and pulled me by my cock and balls. Fortunately, the rain had stopped topside.

I could see the man she called Miguel. He was in his early 20s and muscular. He was tan with wavy hair. He would have made any woman crazy. "How does Boy like the man Mistress has been spending time with since Boy fucked up?"

"Boy likes him very much Mistress."

"Excellent Boy. Go make Miguel hard." I looked at Miguel who had spread his legs and scooted to the edge of the chair. His balls hung over the edge. I started to feel so uncomfortable that I almost stopped. I knew Mistress would completely sever our relationship if I did that.

I hastily moved towards Miguel and kneeled between his legs. His cock looked very small, even taking into consideration he was soft. I couldn't see what Mistress wanted with him. I grabbed his cock. My own was throbbing.

The clouds had parted and the sun was beating down on us. My hand slid very easily up and down his cock because of the sweat that had collected there. I was hoping the other houses didn't have people bird watching on their decks. I didn't want anyone to see me on my knees stroking another man's cock.

After a few strokes, I could feel his dick begin to swell. "Boy, hands behind your back," Mistress said. I saw Miguel smile. He grabbed the base of his cock and gave it a few strokes himself. He put his hand around my head and brought me forward.

My mouth opened the same way it would if Mistress was going to spit on me. He moved my head down onto his cock and pushed my head slowly down his cock. I gagged, feeling its limp, softness lying against my tongue. He guided my head up slowly and then brought it back down. I could feel it getting harder and thicker by the second.

At full harness, he held my head in place and began thrusting his cock in my mouth. Mistress walked over and sat beside Miguel. She took his hands from my head and put them on her breasts. I kept taking the full length of his cock. Surprisingly, it was probably 8 inches. Mistress flicked her tongue against Miguel's and their lips pressed together.

I wanted to bite down on his cock and have mistress all to myself. Jealousy was starting to and I was about to explode. Her skin was glistening in the sun. The sun reflecting off the boat illuminated her beautiful golden tan. The wind blew out her hair. She looked amazing and I wanted her attention, but I kept sucking that fucking asshole's cock.

Miguel violated Mistress for several long minutes. I knew there was no way he could satisfy her like Boy. Miguel leaned his head back, closed his eyes, and I continued to swallow his cock with my hands still behind my back.

"That's really good Boy," she said standing next to me. "Boy is enjoying sucking cock more than Mistress thought." She pushed me hard and I fell over onto the deck. "On your fucking back. Spread your fucking legs."

I did as told. The string kept my cock from going soft while I sucked Miguel's cock. I hated the experience. She walked over to me and started jerking off my cock with her toes. The red polish on her big toe reminded me of the time she let me cum on her feet. I felt a surge in my cock and my body jumped. "Boy likes sucking dick. Boy is rock hard after swallowing Miguel's man cock."

She ran her toe from the tip of my cock, down my shaft and balls, and to my asshole. I felt her putting pressure on it with her toe. We had not explored that area. The skin around my puckered ass hole was so sensitive to her touch. I felt my cock growing wider causing the string to tug tighter.

"Boy's fantasy is about to come true. Boy acted so ugly last time that he still has to be punished. Mistress knows how much Boy wants a cock shoved into his ass so Mistress won't punish Boy by taking that away. Boy is going to take every inch of Miguel's cock with only Boy's spit as lube."

My eyes widened and I stared at Mistress. I almost didn't believe her, but Mistress doesn't lie She waved for Miguel to come over. Mistress bent down and cut the string from my cock and balls. My balls fell so much relief as they hung in their normal position and my cock rested against my stomach.

Miguel stroked his cock between his thumb and forefinger. Then he grabbed it by the base and put it against my balls. He bounced my sack up and down with the tip of his cock. I felt pre cum dribbling onto my stomach. The sensation was incredible.

"Hold your ass open Boy." I grabbed my ass with both of my hands and spread my cheeks as wide as I could. Miguel rubbed his cock head up and down as if he was rubbing the slit of a pussy. I had anal sex with my x-wife and girlfriend so I knew lube was necessary.

He pressed his cock against my asshole. My sphincter muscles gave him some resistance. He put his hands to my side and got on top of me in missionary position. I felt like some scared girl about to lose her virginity.

Soon he thrust his cock into me really hard and grunted. I felt tearing pain as his cock shoved deep into my bowels. He closed his eyes as if they were burning from pleasure. I wanted to knock him off me, but my hands never left my ass. He gave me slow hard thrusts. His cock stimulated my prostate and pain turned to pleasure.

I noticed a shadow move in front of me and I opened my eyes. Mistress was lowering her pussy to my face. I stuck out my tongue to taste her sweet pussy juice. It was a treat for Mistress to let Boy taste her. I held out my tongue and let the rhythm of Miguel's thrusting guide my tongue across her pussy.

I let go of my ass with one hand and put my thumb against her clit. She grinded against my thumb. I could taste her juices flowing into my mouth. I knew she was going to cum soon. She sat completely on my face and I couldn't breath. I turned my head from side to side, hoping my nose rubbing her slit was getting her off. She put her hands on my chest and moved her pelvis back and forth. I felt her body spasm and shiver over my face. She rocked forward a few more times, and then lifted herself off, my face covered in cum

Reality hit me as I was gasping for air. Mistress had already cum, so I wasn't going to be able to fuck Mistress and I had a cock balls deep in my ass. Miguel kept plowing away at my ass as if he didn't realize Mistress came.

I watched Mistress walk over to the bench. She clapped her hands for Miguel to stop. Miguel pulled out of me and sat beside her. I felt emptiness that I wanted filled. I stayed on my back with my cheeks spread wide. My asshole contracted and relaxed into its gaping position.

"Get up Boy. Come ride Miguel's cock." I did as told. I felt silly being a grown man sitting in this guy's lap. He just sat there with his legs spread and his hard cock pointed up. I could never last that long at his age.

I had women in that position so man times but felt awkward doing it myself. I put my hands on his shoulders to steady myself. I put one leg on each side of him and lowered myself down. Miguel grabbed my cock and rubbed it on his cock head. Some of our pre cum mixed. I positioned myself over his cock and he pointed it towards my gaping asshole.

I had to let him in my ass instead of having my asshole virginity taken by force. It was fulfilling having his cock sliding up my ass. I held my ass to make it easier to slide his cock in and out. Miguel put his hands behind his head and watched me in action.

I started working faster on his cock. I looked at Mistress and saw how pleased Mistress was. I worked faster. Mistress leaned over, grabbed my cock, and started stroking expertly. With every stroke, I could feel cum building, ready to pop all over Miguel's stomach.

Mistress let go of my cock and I immediately took over. I squeezed my hand tightly around my cock, but imagined it was Mistress' tight pussy. I jerked it so hard and fast that it took me less than ten strokes to cum. Streams of hot, white, creamy cum went all over Miguel's stomach. I looked down at my work. It was the biggest load I produced in a long time.

I collapsed onto Miguel's chest as he bucked his cock into my ass. I felt my balls draw up into my body and drop back down. It hurt feeling Miguel drill into my ass after I came. When I could hardly stand it, he grabbed me by the waist and pushed me down hard on his cock. My ass hole contracted around his cock as he slowly pulled me up. My ass felt slick as he pulled his cock out of my ass. Cum dripped out of my gaping hole and Miguel pushed me off him.

"That was good Boy. Lick Miguel clean." It was so humiliating. I lapped up my cum like a dog drinking out of a lake. The taste was fowl, but I swallowed it all. I felt how hard Miguel's stomach was with my tongue. I started feeling self-conscious about the softness of my belly. I was going to work on myself for Mistress.

"That was excellent Boy. I am happy your fantasy came true."

"Thank you Mistress. Boy enjoyed it."

"Until next time, Boy. Leave me here with Miguel." I felt jealousy rise in me again. I wanted to knock Miguel into the water, but I couldn't even look at the guy who just fucked my ass. My cock was shrinking so decided it was best to leave.

On my way to the car, I could still feel Miguel's cum leaking out of me. I felt like such a cock whore. My asshole was throbbing. My cock didn't even get to pleasure Mistress. I still didn't like cock, but if Mistress wanted me to take another cock, I would spread my legs again. I went back home and spread out on the couch. I never bothered to dress. I replayed the day in my head and jerked off. I shot cum all over my chest and thought about my cum covering Miguel's stomach. I fell into a blissful sleep.