This is my very first time writing anything like this and plan to do many more in the future if this one goes well! So sit back, make yourself comfortable, and enjoy the show!
***
It was that time again for the annual business conference in the big city where thousands of want-to-be business entrepreneurs gather to hear the latest news on how to make it big. I was there along with three of my co-workers; Jessica, Brooke, and Sara, enjoying the show and the entertainment.
Upon the completion of the conference, everyone casually walked back to their hotel rooms to prepare for the feast in the ballroom. I had arrived about a half hour late to my room after chatting with some old colleagues and finally was able to start getting dressed for the night. My room had a door connecting it to my co-worker's room just next door and I noticed it was open just a crack. I thought nothing of it because we had been visiting each other's rooms throughout the day. It wasn't until I had taken my suit jacket off when I heard noises coming from the other room.
Curiously, I quietly walked over to the door and peered through the crack and what happened next blew my mind away. I look and see all three of my co-workers naked except for their panties in one bed snogging and playing with each other. My heart dropped as I tried not to gasp in shock. Mixed emotions were playing through my head; stay professional, or keep rubbing myself as I was there, watching.
I'm not sure how long I was standing there, looking through the crack when I accidently pushed the door too far, causing it to squeak. Instantly, all three of them look over at the door as I quickly close the door shut. I know I had been caught but I tried to keep my cool and act as if I never looked.
"Michael! Open this door right now mister!" Jessica yells, banging on the door.
I hesitated for a while, trying not to make any sounds and debating on what I should do. I know they saw me and can only imagine what they think of me now...some kind of pervert? Against my better judgement, I opened the door to see all three girls standing there in only their panties with pissed faces. As soon as I opened the door, they grabbed me by my shirt and forcibly pulled me into the room and close the door behind them.
I'm now standing there, in the middle of the room, with the most embarrassed face, trying not to look at them.
"And just what did you think you were doing spying on us?" Brooke snaps.
"I uhh...I heard a noise and went over to the door and saw you...uhhh..."
"Invading us of our privacy is a very serious matter Michael, not to mention creepy. I might just tell our boss, Mr. Johnson about this." Jessica says, staring straight into my eyes.
"Oh please no Jess!" I get on my knees in front of her, holding her hand. I look pathetic but I did not want to lose my job and possible legal charges against me. "I won't tell anyone and I won't look anymore! I'm sorry!"
"I'm afraid sorry won't cut it this time mister!" Sara says crossly, reaching for her phone.
"Please don't tell Mr. Johnson! I'll do anything!" I am yelling at this point, almost in tears.
"Wait Sara.." Jessica says. "He said he'll do anything!"
At that moment, all three of them simultaneously looked at me with the evilest, naughtiest faces I've ever seen.
"We won't tell Mr. Johnson, but we will teach you about spying on our privacy!" Jessica says as she pushes me backwards onto the bed. "Sara, Brooke, grab his arms."
Both Sara and Brooke grab each of my arms and hold them above my head as Jessica unties my tie and uses it to bind my right leg to the post. She then goes into my room, finds another tie and does the same to the left leg, leaving me completely defenseless.
"Wha..what are you doing Jess!" I stamper.
Out of nowhere, Jessica slaps me across the face. "That's Mistress Jessica to you, mister! And don't let me have to say it again!"
The slap didn't hurt but it stung a bit on my unaware cheek. "Yes Mistress Jessica," I say, trying to wiggle free but unable to.
"Good, now answer me clearly. Did you pack another shirt with you?" Jessica asks, again looking straight into my eyes.
"Yes Mistress Jessica. There's another one hanging up in my..." I try to explain before another slap strikes my face.
"I didn't ask where, I asked did you!" Jessica snaps.
"Yes Mistress Jessica," I say, wanting to rub my stinging cheek.
"That's better. In that case, I guess you won't be needing this, will you?" Mistress Jessica grabs my shirt and yanks it apart, sending a few buttons flying. A small moan arises from Sara as my somewhat in-shape chest is exposed. Mistress Jessica then goes for my pants, yanking them open and pulling them down by my bound ankles. My hidden boner is now visible to all three girls.
"What's this?? Are you enjoying this Michael?" Mistress Jessica snaps, slapping me in the face twice.
"No Mistress Jessica, it's just natural I can't control it!" I say totally embarrassed, red to the face.
"Can't control it? But I can," Mistress Jessica says, slapping my hard cock many times through my boxer briefs. I yell loud as the pain is unbearable. The slapping did nothing but make me harder and hornier. She then slaps my face once again. "You'd better keep it quiet or the neighbors will complain! Sara, Brooke, take off your panties."
Sara and Brooke do as they're told, Sara removing her blue lace boyshorts, Brooke removing her black lace thong, and Mistress Jessica removing her black lace tangas. Now they're all completely naked, making my exposed boner rage to get out of my tight undies. Mistress Jessica gathers all the underwear, rolls them into a ball and forces them into my mouth, gagging me.
"There, now no matter what we do to you, no one will hear you," Mistress Jessica smirks. I muffle through the panty ball, soaked with the juices of the girls, making me moan.
"Yeah that's right, whatever...we...do..." Mistress Brooke twists my nipples between every word, making me moan loudly into the panty ball.
Mistress Jessica bends down and pulls my underwear down to my ankles, giving my raging hard cock room to breath as it stands there erect. Then she teases my cock by hovering her mouth just inches from the head, blowing hot, moist breath, making me shiver.
"You want it, don't you?"
"Yes Mistress Jessica,"
"Well too bad! Bad boys don't get what they want! They get punished!" She raises her voice.
"Move that table closer and bend him over,"
Sara and Brook release my arms to grab the table and I lower my arms to the side when Mistress Jessica gives me a sharp glare. I instantly raise my arms to where they were.
Once the table is moved, Mistress Jessica unties my ankles and Brooke and Sara grab my arms again and bend me over the edge, tying my ankles to the legs of the table and my arms to the opposite ends. I am completely vulnerable now.
"Now normally I would leave this for the girls and me, but since you've been so naughty, this is all for you!" Mistress Jessica reaches into her bag and pulls out a strap on with an 8 inch flesh colored dildo attached to it.
My eyes widen and I produce a smile before quickly returning my face to normal. Mistress Jessica notices my look.
"Do you have something to say?"
I try to say something but the panty gag muffles my speech. Mistress Jessica stomps over and removes the gag. "Well...um... my biggest fetish happens to be getting pegged by a pretty woman..." * I added pretty to try to soften the punishment but it had no affect.*
"Ohhhh...we have a sissy boy here girls!" She says with excitement. "He actually wants to get fucked in the ass!"
The other girls giggle and moan louder as I could tell they all wanted to participate.
"I'm not a sissy boy!" I talked back which was a terrible idea as Mistress Sara went over and grabbed a paddle from the bag. She walked up behind me and gave me a hard smack on the right cheek.
"Don't you ever talk back to your mistress like that!" Mistress Sara yells and smacks the other cheek.
The pain was intense and tried to apologize but was too caught up in the pain I only said,
"Oww...I'm sorry Jessica!" completely forgetting to add Mistress.
Mistress Jessica immediately grabs the paddle and walks over to my face on the other end of the table.
"I thought I told you it's Mistress Jessica from now on...now you will count to 10 at every smack and if I do not hear you, we start all over. And the gag goes back in too. Do you understand me, slut?"
"Yes Mistress Jessica!" I said, trying to prepare my ass for the spanking of a lifetime. Mistress Jessica rubs the panty ball along her pussy and puts it back in my mouth and stands behind me and smacks..."1"
"Good boy" Brooke says, moaning from the corner, obviously had been touching herself.
*SMACK*..."2"
*SMACK*..."3"
*SMACK*..."4"
My ass is on fire but it feels so good I only moan loudly.
*SMACK*..."5"
*SMACK*..."6"
*SMACK*..."7"
I am gripping the ties that bind my wrists, trying to endure the pain.
*SMACK*..."8"
*SMACK*..."9"
*SMACK*... "10"
I let out one last big grunt and moan as Mistress Jessica rubs the paddle against my tomato red ass cheeks.
"Very nice slut, I think you enjoyed that. Remember, every slip up and I add 10 each time." She then assembles the strap on and sticks it deep in my mouth, making me choke. The 8 inch cock fills my throat causing me to gag and my eyes to water... I felt like such a slut but I was loving it. Mistress Jessica removes the cock, allowing me to catch my breath. She walks behind me and I feel the tip just touching my hole, the anticipation was killing me, one stroke of my cock and I would've came right there.
"That's it slut, nice and slow," Mistress Jessica says as she slowly pushes her cock deep in my ass, making me moan into the panty gag, soaked with my saliva and my Mistress' juices. The slow in and out of my ass feels incredible after the pain of being stretched had subsided. The pace increased and so did my moans, I was white-knuckling my fists at the pleasure trying not to cum.
Mistress Brooke walks over to my mouth, removes the gag and pushes my head into her soaking wet pussy. She let out a deep moan as she ordered me to lick her inside and out. She tasted so good, my mouth was full of her juices and had some dripping down my chin. I could tell she was close as she pushed me into her harder, just as Mistress Jessica went into me suddenly full length, making me moan and pushing Mistress Brooke over the edge. Her juices went flying into my face, and when she recovered from her intense orgasm, she moved to my rock hard cock.
Mistress Sara then did the same thing, pushing my head into her pussy, pushing out many intense orgasms, as Mistress Brooke slowly rubbed my cock. The pleasure was unbearable I felt as if I was going to cum right there.
"Mistress Jessica may I please cum!" I muffle from between the legs of Mistress Sara.
"Not yet cum slut!" She starts to really pound my ass.
My moans increase as my cock feels as if it's going to burst.
"Please Mistress Jessica!" I try again.
"Not yet, and don't you dare cum without my permission dammit!" Mistress Jessica scowled.
Mistress Jessica continues to pound my ass the hardest she could, I'm still licking Mistress Sara's clit, and Mistress Brooke strokes my cock even harder. I couldn't hold it! I let out a scream that I did not recognize as my own voice as wave after wave of pleasure jolted through my body, testing the knots on the restraints.
After I recover from the most intense orgasm of my life, I see all three Mistresses standing in front of me, looking unpleased.
"Why the hell did you think you could cum without my permission mister!" Mistress Jessica scolded.
"I'm sorry Mistress, I tried to hold it!" I weakly say.
"Well since you keep disobeying my orders, after we were done I was going to invite you to dinner with us, but since you are a useless, disobedient cum slut, I've got one more thing just for you." Mistress Jessica smirks as she walks to her bag and pulls out a G-spot vibrator. "Since you want to cum so much, I'm going to let you, but you are going to cum over and over without anyway to stop!"
Mistress Jessica shoves the small vibrator into my sore, gaping asshole and turns it on low vibrate. A sudden chill travels my body as I can already feel my cock reviving.
I'm leaving you just like this for the rest of the night while the girls and I go out!" Mistress Jessica says as the girls get dressed in their business attire.
Mistress Jessica shoves the panty gag back into my mouth and starts her way to the door. She hesitates then walks back and turns the vibrator on max, making me moan loudly and shake the table as the vibrations shoot straight into my prostate.
"There we go. Have a good night Michael!" Mistress Jessica says as the other girls laugh through the doorway and close the door behind them.
***
It was that time again for the annual business conference in the big city where thousands of want-to-be business entrepreneurs gather to hear the latest news on how to make it big. I was there along with three of my co-workers; Jessica, Brooke, and Sara, enjoying the show and the entertainment.
Upon the completion of the conference, everyone casually walked back to their hotel rooms to prepare for the feast in the ballroom. I had arrived about a half hour late to my room after chatting with some old colleagues and finally was able to start getting dressed for the night. My room had a door connecting it to my co-worker's room just next door and I noticed it was open just a crack. I thought nothing of it because we had been visiting each other's rooms throughout the day. It wasn't until I had taken my suit jacket off when I heard noises coming from the other room.
Curiously, I quietly walked over to the door and peered through the crack and what happened next blew my mind away. I look and see all three of my co-workers naked except for their panties in one bed snogging and playing with each other. My heart dropped as I tried not to gasp in shock. Mixed emotions were playing through my head; stay professional, or keep rubbing myself as I was there, watching.
I'm not sure how long I was standing there, looking through the crack when I accidently pushed the door too far, causing it to squeak. Instantly, all three of them look over at the door as I quickly close the door shut. I know I had been caught but I tried to keep my cool and act as if I never looked.
"Michael! Open this door right now mister!" Jessica yells, banging on the door.
I hesitated for a while, trying not to make any sounds and debating on what I should do. I know they saw me and can only imagine what they think of me now...some kind of pervert? Against my better judgement, I opened the door to see all three girls standing there in only their panties with pissed faces. As soon as I opened the door, they grabbed me by my shirt and forcibly pulled me into the room and close the door behind them.
I'm now standing there, in the middle of the room, with the most embarrassed face, trying not to look at them.
"And just what did you think you were doing spying on us?" Brooke snaps.
"I uhh...I heard a noise and went over to the door and saw you...uhhh..."
"Invading us of our privacy is a very serious matter Michael, not to mention creepy. I might just tell our boss, Mr. Johnson about this." Jessica says, staring straight into my eyes.
"Oh please no Jess!" I get on my knees in front of her, holding her hand. I look pathetic but I did not want to lose my job and possible legal charges against me. "I won't tell anyone and I won't look anymore! I'm sorry!"
"I'm afraid sorry won't cut it this time mister!" Sara says crossly, reaching for her phone.
"Please don't tell Mr. Johnson! I'll do anything!" I am yelling at this point, almost in tears.
"Wait Sara.." Jessica says. "He said he'll do anything!"
At that moment, all three of them simultaneously looked at me with the evilest, naughtiest faces I've ever seen.
"We won't tell Mr. Johnson, but we will teach you about spying on our privacy!" Jessica says as she pushes me backwards onto the bed. "Sara, Brooke, grab his arms."
Both Sara and Brooke grab each of my arms and hold them above my head as Jessica unties my tie and uses it to bind my right leg to the post. She then goes into my room, finds another tie and does the same to the left leg, leaving me completely defenseless.
"Wha..what are you doing Jess!" I stamper.
Out of nowhere, Jessica slaps me across the face. "That's Mistress Jessica to you, mister! And don't let me have to say it again!"
The slap didn't hurt but it stung a bit on my unaware cheek. "Yes Mistress Jessica," I say, trying to wiggle free but unable to.
"Good, now answer me clearly. Did you pack another shirt with you?" Jessica asks, again looking straight into my eyes.
"Yes Mistress Jessica. There's another one hanging up in my..." I try to explain before another slap strikes my face.
"I didn't ask where, I asked did you!" Jessica snaps.
"Yes Mistress Jessica," I say, wanting to rub my stinging cheek.
"That's better. In that case, I guess you won't be needing this, will you?" Mistress Jessica grabs my shirt and yanks it apart, sending a few buttons flying. A small moan arises from Sara as my somewhat in-shape chest is exposed. Mistress Jessica then goes for my pants, yanking them open and pulling them down by my bound ankles. My hidden boner is now visible to all three girls.
"What's this?? Are you enjoying this Michael?" Mistress Jessica snaps, slapping me in the face twice.
"No Mistress Jessica, it's just natural I can't control it!" I say totally embarrassed, red to the face.
"Can't control it? But I can," Mistress Jessica says, slapping my hard cock many times through my boxer briefs. I yell loud as the pain is unbearable. The slapping did nothing but make me harder and hornier. She then slaps my face once again. "You'd better keep it quiet or the neighbors will complain! Sara, Brooke, take off your panties."
Sara and Brooke do as they're told, Sara removing her blue lace boyshorts, Brooke removing her black lace thong, and Mistress Jessica removing her black lace tangas. Now they're all completely naked, making my exposed boner rage to get out of my tight undies. Mistress Jessica gathers all the underwear, rolls them into a ball and forces them into my mouth, gagging me.
"There, now no matter what we do to you, no one will hear you," Mistress Jessica smirks. I muffle through the panty ball, soaked with the juices of the girls, making me moan.
"Yeah that's right, whatever...we...do..." Mistress Brooke twists my nipples between every word, making me moan loudly into the panty ball.
Mistress Jessica bends down and pulls my underwear down to my ankles, giving my raging hard cock room to breath as it stands there erect. Then she teases my cock by hovering her mouth just inches from the head, blowing hot, moist breath, making me shiver.
"You want it, don't you?"
"Yes Mistress Jessica,"
"Well too bad! Bad boys don't get what they want! They get punished!" She raises her voice.
"Move that table closer and bend him over,"
Sara and Brook release my arms to grab the table and I lower my arms to the side when Mistress Jessica gives me a sharp glare. I instantly raise my arms to where they were.
Once the table is moved, Mistress Jessica unties my ankles and Brooke and Sara grab my arms again and bend me over the edge, tying my ankles to the legs of the table and my arms to the opposite ends. I am completely vulnerable now.
"Now normally I would leave this for the girls and me, but since you've been so naughty, this is all for you!" Mistress Jessica reaches into her bag and pulls out a strap on with an 8 inch flesh colored dildo attached to it.
My eyes widen and I produce a smile before quickly returning my face to normal. Mistress Jessica notices my look.
"Do you have something to say?"
I try to say something but the panty gag muffles my speech. Mistress Jessica stomps over and removes the gag. "Well...um... my biggest fetish happens to be getting pegged by a pretty woman..." * I added pretty to try to soften the punishment but it had no affect.*
"Ohhhh...we have a sissy boy here girls!" She says with excitement. "He actually wants to get fucked in the ass!"
The other girls giggle and moan louder as I could tell they all wanted to participate.
"I'm not a sissy boy!" I talked back which was a terrible idea as Mistress Sara went over and grabbed a paddle from the bag. She walked up behind me and gave me a hard smack on the right cheek.
"Don't you ever talk back to your mistress like that!" Mistress Sara yells and smacks the other cheek.
The pain was intense and tried to apologize but was too caught up in the pain I only said,
"Oww...I'm sorry Jessica!" completely forgetting to add Mistress.
Mistress Jessica immediately grabs the paddle and walks over to my face on the other end of the table.
"I thought I told you it's Mistress Jessica from now on...now you will count to 10 at every smack and if I do not hear you, we start all over. And the gag goes back in too. Do you understand me, slut?"
"Yes Mistress Jessica!" I said, trying to prepare my ass for the spanking of a lifetime. Mistress Jessica rubs the panty ball along her pussy and puts it back in my mouth and stands behind me and smacks..."1"
"Good boy" Brooke says, moaning from the corner, obviously had been touching herself.
*SMACK*..."2"
*SMACK*..."3"
*SMACK*..."4"
My ass is on fire but it feels so good I only moan loudly.
*SMACK*..."5"
*SMACK*..."6"
*SMACK*..."7"
I am gripping the ties that bind my wrists, trying to endure the pain.
*SMACK*..."8"
*SMACK*..."9"
*SMACK*... "10"
I let out one last big grunt and moan as Mistress Jessica rubs the paddle against my tomato red ass cheeks.
"Very nice slut, I think you enjoyed that. Remember, every slip up and I add 10 each time." She then assembles the strap on and sticks it deep in my mouth, making me choke. The 8 inch cock fills my throat causing me to gag and my eyes to water... I felt like such a slut but I was loving it. Mistress Jessica removes the cock, allowing me to catch my breath. She walks behind me and I feel the tip just touching my hole, the anticipation was killing me, one stroke of my cock and I would've came right there.
"That's it slut, nice and slow," Mistress Jessica says as she slowly pushes her cock deep in my ass, making me moan into the panty gag, soaked with my saliva and my Mistress' juices. The slow in and out of my ass feels incredible after the pain of being stretched had subsided. The pace increased and so did my moans, I was white-knuckling my fists at the pleasure trying not to cum.
Mistress Brooke walks over to my mouth, removes the gag and pushes my head into her soaking wet pussy. She let out a deep moan as she ordered me to lick her inside and out. She tasted so good, my mouth was full of her juices and had some dripping down my chin. I could tell she was close as she pushed me into her harder, just as Mistress Jessica went into me suddenly full length, making me moan and pushing Mistress Brooke over the edge. Her juices went flying into my face, and when she recovered from her intense orgasm, she moved to my rock hard cock.
Mistress Sara then did the same thing, pushing my head into her pussy, pushing out many intense orgasms, as Mistress Brooke slowly rubbed my cock. The pleasure was unbearable I felt as if I was going to cum right there.
"Mistress Jessica may I please cum!" I muffle from between the legs of Mistress Sara.
"Not yet cum slut!" She starts to really pound my ass.
My moans increase as my cock feels as if it's going to burst.
"Please Mistress Jessica!" I try again.
"Not yet, and don't you dare cum without my permission dammit!" Mistress Jessica scowled.
Mistress Jessica continues to pound my ass the hardest she could, I'm still licking Mistress Sara's clit, and Mistress Brooke strokes my cock even harder. I couldn't hold it! I let out a scream that I did not recognize as my own voice as wave after wave of pleasure jolted through my body, testing the knots on the restraints.
After I recover from the most intense orgasm of my life, I see all three Mistresses standing in front of me, looking unpleased.
"Why the hell did you think you could cum without my permission mister!" Mistress Jessica scolded.
"I'm sorry Mistress, I tried to hold it!" I weakly say.
"Well since you keep disobeying my orders, after we were done I was going to invite you to dinner with us, but since you are a useless, disobedient cum slut, I've got one more thing just for you." Mistress Jessica smirks as she walks to her bag and pulls out a G-spot vibrator. "Since you want to cum so much, I'm going to let you, but you are going to cum over and over without anyway to stop!"
Mistress Jessica shoves the small vibrator into my sore, gaping asshole and turns it on low vibrate. A sudden chill travels my body as I can already feel my cock reviving.
I'm leaving you just like this for the rest of the night while the girls and I go out!" Mistress Jessica says as the girls get dressed in their business attire.
Mistress Jessica shoves the panty gag back into my mouth and starts her way to the door. She hesitates then walks back and turns the vibrator on max, making me moan loudly and shake the table as the vibrations shoot straight into my prostate.
"There we go. Have a good night Michael!" Mistress Jessica says as the other girls laugh through the doorway and close the door behind them.