Loading...The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me.
“Hey, you’re early. Knock’em dead big guy.” She was older then me. I liked older women and I had told her that many times before. But she was married and I just flirted with her. I would often drop a hint here and there. She never did back away from a conversation. I even told her she should have a web site and become a Mistress, a Dominatrix. She laughed as I walked by her and smacked my ass.
“Can’t a guy be alone?” I winked at her. She winked back and turned to leave.
“When you finish with your filing come visit me in the kitchen.”
“Ok, I’ll do that.” I figured she just wanted some company. Of course I didn’t have all the information to complete the application. I’d have to call the clients later. Nothing else I could do. I figured it was time to go harass Betty.
“Done so fast,” she saw me walk through the door and head for the coffee pot.
“No, I just can’t get my mind off of you and that red hair of yours. You sure you’re still married?” I loved asking her that question.
“Yeah, I am. Get your coffee and follow me.” I was out the door walking besides her down the short hall. The small office in the back had a door and no windows. There was a TV, couch and a computer. Betty went straight to the computer.
“Checking your email”, I said.
“Yeah, just jokes from you and my sister.” She looked up at me with a surprised look.
“Look what we got here.” I walked around to face the screen. It was a word document.
“Read this, could you do that for me?”
“Sure, anything for you.” I leaned over the back of her chair and began to read.
“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. I knew what this was. I tried to hesitate a little but Betty would have no of that.
“Keep reading.” So I did as I was told
“Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot.
“I have a few cold beers in the fridge,” she cooed. “Why don’t you take a break sissy boy and wiggle your ass up the stairs for me and Karen.” I almost fell on my face running up the stairs.
I had become engrossed with reading this story. I was also scared to death. Betty had found the story I had written on the computer. I had typed it the day before and submitted it to Literotica.
“You don’t want me to read this to you, do you?
“Of course I do, I would not have asked you to read. So if you will be so kind, please continue.” Her eyes were staring right at me. She was serious. I did have one way to end this right here.
“The girls will be here any minute. We can read it another time.” I reached over her shoulder to click the screen off. She grabbed my hand before I got to the mouse.
“No, your going to read it to me, understood.” Of course it was understood. I don’t know if she knew how excited I had become by doing this.
“They are all gone until noon. Remember, they went to corporate today.”
“What about,” she cut me off before I finished.
“They are out in meetings.” You are supposed to be here with me helping answer the phones. Remember?”
“Your right, but I don’t want to make you feel uncomfortable.” I really wanted to stop.
“Uncomfortable, Michael, I’m not the one uncomfortable. Just relax and read it. You wrote and I want to here you read it to me.” She was serious.
I took a breath.
It was hot out, did I tell you that already. We were in the middle of a heat wave at the Jersey Shore. Things had slowed down a bit, people were on vacation, just moving a bit slower in this weather. The shore had been packed the last 6 weeks. Record crowds and too much traffic, all the locals bitched from Memorial Day through Labor Day. But we all knew the bottom line was the money made from the “Bennies”. The Jersey Shore is a great place to live and play. Lots of money, lots of fun people. And the women, single, divorced, married, it didn’t matter. On the job, after hours, they were all horny.
Betty told me to get the chair from the desk and get comfortable. She was relaxed, her head tilted to the left.
The girls were sitting around the small conference table in the back office. I heard some Pink Floyd on the stereo. Seems like the workday was about to come to an end. Karen had the same color halter on. As a matter of fact, they both had identical shorts and sandals on. How cute and sexy! I helped myself to a cold Sam Adams and took a seat between the two beauties. Lisa had her feet resting on the edge of the table. I love her legs, her ass and those sandals just drove me fucking crazy. She winked at me.
Betty shifted around in her seat. She must have not read this, no, what was I thinking. She had already read this. That meant she was cool with it. Hmmmm, I thought, this could get interesting. I read with a little more flavor.
“Hey sweetie pie, you’re working too hard.” She leaned her head back and took a swig. Her tits were ready to burst out of that tight top. Her eyes caught me staring.
“Listen sissy boy, we had so much fun with you last time, we were wondering…”
Karen spoke up, “We want to play.” She said it with the sexiest voice, even Lisa turned towards her. We both smiled at her. Karen reached down behind her chair and produced a bag.
“Go take a shower, then take this bag upstairs and put your cute little outfit on.” Lisa didn’t have to ask twice. They watched me stripped my clothes off.
Silence, Betty was into it. So was I, I continued;
I threw them on the conference table. The hooting and whistling made my dick grow hard. I gyrated my hips towards Lisa’s face. She grabbed me by my dick in a very rough way. I stopped the show.
“Listen sissy, you do as we say. That’s what we like.” She looked up into my eyes. I avoided her stare as I spoke.
“Yes Lisa,” I said meekly. She squeezed hard as she stroked my hard on.
“Yes mistress, say it sissy.” I had a raging hard on, but I managed to say it.
“Yes mistress.”
“Yes mistress, cute Michael, very cute. Continue, please.”
“Good, now do as you are told.” She released my dick, it was a purplish red and I wanted to just jerk off right then and there because I was that close to exploding. But I regained some type of composure and turned towards the shower with the bag under my arm.
The water felt good. I was dirty and sweaty so the girls had every right to have me clean up before we had playtime. I made it a quick shower, all the while expecting one or two of them to join me. No one came in, so I wrapped the towel around my waist and headed up the stairs. There was some small talk coming from the conference room. I didn’t go back to them, I did as I was told.
I had begun to rub her shoulders, slightly rub them. She didn’t object. I was so turned on and I wanted to ask her so many questions. But she wanted me to read.
The bag held some very hot goodies. In addition to panties, bra and stockings, they had some garters for me to wear. I ran my fingers through the lacy panties, the stocking were a white sheer material that felt so smooth. Dropping my towel, I started with those sexy stockings. The panties were tiny, a tight little thong that barely held my dick. The head of my dick stuck out of the pouch as I grew in anticipation. The bra was also very silky to the touch. There was a wig as well and a small leather pouch still in the bag the girls had given to me. I reached in and found a note under the leather pouch.
“Slut,” it started out with. “You are in for some fun. We love having you as our sissy boy. Do as you are told and all your sissy boy fantasies will come true.” It was signed, “Your hot blonde Mistress Lisa and Mistress Karen… smack!”
I was rubbing myself through my pants and I didn’t even realize it. Betty caught me. She took my hand from the growing bulge in my pants. She didn’t say anything other then “Read.”
I opened the leather pouch and found some interesting toys. A red dildo, a 6″ vibrator, a string of beads, a tube of KY. There was a DVD as well. I opened the case up and there was another note. “Put this on and make yourself nice and hard for us, but do not cum.” I could have cum right then, wearing those sexy white stockings. I laughed as I read the title, “Sissy boys serving their Mistress.”
I took a breath and figured I wouldn’t stop until I was done. Betty was squirming in her chair. She was turned on like I was. Her hand brushed my hand on her shoulder. It was like electricity passing between us. I wanted to, well I kept reading
I did as I was told. I finished putting on my wig and pumps. The new twist they had added had me applying my own lipstick. So there I was, puckering up my lips and smearing a slutty deep red lipstick onto my lips. That got me thinking, what the fuck am I doing. But the hard on peeking through my thong kept me going. I pressed play on the DVD. I heard small talk from downstairs. They were definitely moving around. I listened for footsteps coming up the stairs, but there wasn’t a squeak to be heard. The action on the screen started right from the beginning. A hot leather mistress, a sissy boy dressed like a girl, oh my! My dick was straining, I played with it just a little bit. It grew to its full length real fast and I had to stop in order not to cum. The action got hotter when the mistress told her boy to bend over and spread his ass. “Fuck me, fuck me like the slut I am”, the actor moaned as her dildo fucked his ass. She pumped it in fast and hard, his panties were down around his ankles, just like me I thought. This was too hot, I played with my hard on a little more, I squeezed the head when I was almost ready to cum. I had my head back and my dick in my hand. I didn’t dare move my hand. The action on the screen was at full tilt, his mistress was fucking him and smacking his ass. I had stopped myself from blowing my load, but the precum had begun to seep from the tip. I took my finger and wiped it off. Bringing it to my lips I licked my finger, enjoying the somewhat salty taste. I heard the squeaky step, but time had stopped by that time.
I looked up and froze. Standing before me was someone other then Karen or Lisa. I was so turned on yet scared to death. Someone else was being let into the circle. I quickly calmed down within a few seconds after recognizing who stood in front of me.
“Hey you sissy fuck, want some company.” The DVD was playing, the moaning grew. “Say it, say you like me to fuck you ass.” My dick was hard, my hand started to stroke it, slowly, trying not to cum… not yet.
Well after reading this I figured I had nothing to hold back. I stood up like I had to stretch. I undid my belt and slid my pants down before she had a chance to object. She didn’t, she wanted more.
“Why stop now, you know you want to jerk off so do it, be my little bitch.” With that my shorts were pulled down over my hard dick. I was standing inches from her face. She looked up at me.
“Jerk off for me sissy boy. And keep on reading.”
There was an empty chair right next to me. I slid to the right and made some room. It was quiet, except for the DVD. “Your ass is so fucking tight.” The mistress fucked her boy. A dick, a real dick was put in front of the sissy boys face and he took it in his mouth. He took it all. His hand wrapped around the base as he began to stroke it. Slowly at first, the rhythm picked up. He licked the sides and played with the balls dangling in front of his face.
“Suck his cock you fucking slut.” She fucked him harder. His head bobbed up and down faster and faster. His hand pumped with a fury.
I began moving my hand with the same rhythm as the one on the screen. My dick was ready, but I knew I couldn’t release until Mistress told me too. I strained and stopped stroking. A hand reached across to wipe the precum from the head of my dick. It twitched, but I was able to hold on.
“You look surprised.” Sticky fingers were licked clean, one by one.
“Yes I am. But I’m really interested into what you want to do.” My dick was hard and I wanted to finish off what I had started.
“You better not cum until I say so, got that.” Betty smacked my ass.
“Yes mistress, I won’t cum until you tell me.” Betty reached out with her hand and helped me along. She flicked her tongue out and gently licked the head of my dick. I was still jerking off and I needed to pace myself so I wouldn’t cum. I continued,
White stocking, garters, everything was the same. Those silky covered legs looked hot. The hard on sticking out of the same little thong was driving me nuts!
“So your part of this too.” Scott had been my friend for years. He was older then me. Now I know why he was always coming by to visit the girls downstairs. At 6’5″ he looked sillier then I was. He got into the action on the screen and began playing with his growing hard on. Same sexy clothes, same wig, same make up. I stroked my dick, knowing how close I was to losing it. But there was no turning back, not with Scott in the room. We didn’t speak, we both just sat back and enjoyed the action on the screen. He stopped jerking off long enough to hand me a note
“Read this, it’s from the girls.” I read it out loud.
“To our two sissy sluts. Get comfortable. Practice sucking each other off, kiss and make out like two lesbians. When we get up there we are going to check out how good you are. And remember, your asses are ours! Now suck some cock.”
It was obvious to Betty I wanted more. She unbuttoned her blouse and undid her bra. She had nice tits and she let me stroke her nipples hard. I heard her moan as I rubbed those puppies. But she made me stop, she wanted to have me finish for her.
“Now finish up this story, you want to finish for me don’t you?”
“Yes mistress, I do.” I began jerking off again, I knew I was almost at the end.
Scott broke the ice. He reached over and stroked my dick. It felt so hot in another man’s hand. He looked me in the eye and said, “We might as well practice.” His wig was off a little, his tiny panties strained to hold his hard on. His dick was the same size as mine. Lisa had told me she didn’t like them too big, just the right size. His wig came off as he leaned over to kiss me. I opened his mouth and kissed him like a girl. Our tongues probed each other’s open mouths, it was the first time I had ever done anything like this. We stood up and groped each other. His hand stroked my dick, I was starting to moan. I took his dick in my hand and did the same. What a turn on. Nothing else was said, even when he went to his knees and took my dick in his mouth. I almost lost it.
Being careful not to make me cum, he worked my dick like he had done this before. His panties were down around his ankles and with his free hand he began jerking himself off. Sucking a little too hard for me to hold back I told him to let me try on him. He stopped sucking and stood up as I licked my way down to his dick. I took him into my mouth. It was everything I had ever dreamed about. I played with his balls and worked my finger around to his asshole. I slipped it in and began to massage that tight spot. He moaned and I told him to talk dirty.
Betty had begun to rub her pussy through her pants. She had undone them and I had made the mistake of trying to pull them down. She smacked me, hard across the ass.
“What the hell do you think your doing? Now finish reading bitch.”
“Suck my dick, you dirty fucking whore.” I did as I was told. The door opened, this time I never heard the squeaky step. I never missed a beat, I continued to suck on his dick. I did see the girls, Mistress Lisa and Mistress Karen that is, enter the room. They were ready for action, each sporting tight leather outfits with a strap on harnessed between their legs.
“Very good, very good.” Lisa stroked her strap on. I could see the lube glisten in the light.
“Make him cum, suck his dick you fucking pansy.” She was topless, she had the best tits. I worked his dick with my hand, making sure to put on a show, I pulled the head out and opened my mouth. He was ready, his dick swelled, he looked down at me. “Open your mouth you cock sucking whore.” He let go, a huge stream of sperm landed on my tongue, then another and then another. It went right into my open mouth, all of it. I never stopped stroking his dick, I milked it for more. I had two fingers buried in his ass. He filled my mouth. I let the girls look in and see that mess. I closed my mouth and swallowed.
“Yum, yum.” Lisa winked at me.
Betty took my hands from my dick and let me rub her pussy.
“You want that pussy don’t you. Well I’m going to fuck you first just like you wrote about. Got that. You’re not getting this pussy before I fuck you first.”
I was ready, my dick was red and hard. I wanted to wait until she told me to cum.
“Read bitch.”
“Now Scotty boy, get on all fours you faggot. We have a nice hard dick to put in you ass.” She smacked him with her riding crop. I licked his dick one last time. Mine was swinging back and forth. Mistress Karen had taken off my panties. She was spreading that gooey lube on her dildo. He fingers worked into my asshole and began to lube and massage it. She stopped long enough to stroke my dick and lean in for a wet kiss. She kissed me passionately, my tongue was in her mouth, and she sucked on it and tasted the sperm I had just swallowed.
“You make me so hot, you sperm swallowing fag. I want you to fuck me, how would you like that.” She took my hand and rubbed it on her wet pussy.
“But I’m going to fuck you after you fuck Scott.” She kissed me again. I played with her tits, she moaned as I rubbed her nipples. Lisa had her dildo in Scott’s ass before I even stood up. She kissed me, then Karen joined in. They played with each other. I was hard once again. Lisa never stopped fucking that ass.
“Your next. Fuck him hard, make him scream.” She let me finger her pussy. She whispered in my ear, “I love watching you suck dick, I’m going to let you fuck my pussy. Just you, not this faggot you are going to fuck.”
I was jerking off furiously for Betty and I wanted to cum, now. She pulled her pants down and showed me her neatly trimmed pussy. Her tits were out too and the sight was too much….
I’m going to cum right now.” She handed me a coffee cup and told me not to spill a drop.
I exploded into the cup, three streams of white cum. She watched me milk it for all it was worth. I was shaking.
“Good boy, now swallow it all, just like you like to do sissy boy.”
I did as I was told.