I am a thirty-five year old married professional guy who has his own office so I get to do pretty much as I please each day, and as long as I get my work done no one will complain. I am a good looking man, just under six feet tall, one hundred seventy five pounds, with steel blue eyes, and just a little salt starting to show in my short brown hair. I haven't ever really had too much trouble getting girls, but with being married now that was the last thing I wanted to do. I love my wife, but my relationship with Dania is 'safe.' She lived in Providence, Rhode Island with her husband, and I in New Jersey, so while it wasn't out of the realm of possibility for us to meet, it wasn't going to happen easily or anytime soon. That's why we played our little game.
I finally got into the office and booted up the computer, which seemed like it was taking forever. Each moment I made her wait, I imagined her dreaming up more severe punishments. Up until now our games consisted of her guiding my masturbation, and having me do silly things like sitting at the toilet to pee and telling her how I felt. The one rule she had with me is that I had to be totally honest with her about everything, and I always was. Today would be no different in that regard.
Finally the instant messaging program loaded, and I saw she had left a message, "Where are you?" was all it said.
I quickly typed in, "I am soooo sorry I am late, I didn't mean to keep you waiting, Mistress," and I waited eagerly for a reply. I was nervous. Did she leave? Am I going to miss out on playing our 'game' today just because of that stupid traffic? Is she really angry? All of these thoughts kept racing through my mind. I desperately want her to reply, but was also worried what that reply would be.
"Finally you show up, slave...," popped up on the screen.
"I am so sorry Mistress, there was traffic and I didn't want to be late, but I couldn't help it," I quickly typed in hoping to alleviate any rage she might be feeling.
"Apology accepted, slave. But...you will still have to be punished."
'Ahhh good,' I thought to myself, at least she is going to keep talking to me.
"You will have to do everything I say today, and provide me with evidence that you have completed the tasks if you ever want to talk with me again after today. Do you understand slave?"
"Yes Mistress, of course, I will do anything you say, anything at all. Please don't stop talking to me?" was what I typed back, and even though it was a game, I would be sad if we didn't get to talk anymore. I had shared a great deal with this woman even though I hardly knew her. She had become a good friend, but now it seemed like it was more.
"For starters, Sissy boy, you are going to go shopping at lunch and buy these items...," and links to different websites began popping up in the messenger screen.
I clicked on the first link and a lingerie website opened up in my browser. I quickly got up and shut my office door. I didn't want anyone in the office to see what I was looking at now. I was embarrassed and I hadn't even done anything yet. The website showed thigh high white, nearly opaque stockings, and a matching garter belt. I blushed, and felt a little awkward looking at the stockings on my work computer. The next website had a set of satin thong panties, four pairs, and all of them were some version of pink. One was solid pink, another was white with pink stripes, the third was pink with little red hearts, and the fourth was more of a hot pink. The last link showed a satin bra with no underwire or padding that almost matched the panty set
“I don’t know where to buy these things, Mistress,” I typed into the messenger.
“Go to your nearest Wal-mart, K-mart, Kohl’s, or Target!” she typed, and it almost seemed as if I could sense her getting angry.
“As you wish, Mistress,” I typed back, and I prepared myself mentally for my lunch break.
I drove to the store. When I got to the K-mart I walked in calmly and got a cart. I picked up some men’s t-shirts, and socks, and other things then made my way over to the lingerie department. I was nervous and I was sure that the sales girl knew what I was there for. I browsed the stockings section and found what I thought was the same pair as, or at least very similar to, what Dania wanted me to get. I quickly found the garter belt to match and the bra wasn’t hard to find either. As I moved over to where the sets of panties were I realized that this was going to be more difficult.
“What size is she?” I heard from off to my left.
“Huh?” I muttered and turned
There stood a very cute, short, blonde sales girl staring right at me. She blinked, the said again, “What size is she?”
I swallowed hard. “Ummm, I don’t know. I guess about my size?” I said.
“And what is she looking for?” she said, this time accenting the word ‘she’.
“A set of four pink satin thong panties,” I said this time without hesitation.
“I like a girl that knows what she wants, they’re right over here, follow me,” and she brushed past me heading off to my right. When I caught up to her she already had the pack in hand. “These are for girls 7-9 in size. Do you think they’ll fit? Perhaps she wants to try them on?” she said smiling at me
“No,” I said, “I’ll just take those if you think that is best.”
“Oh, I am sure they will look hot on her. If you need anything else, or want more help when you come back, find me. I’m Tammy,” she said holding out her hand as if to shake. I quickly shook her hand and thanked her. I could feel myself blushing.
Tammy told me to take everything to register four, and the girl there would check me out quickly. When I got there the girl’s tag read ‘Lizzy’ and she was chewing gum and looking very bored. I took all of the clothes out of the cart at once and dumped them on the conveyor belt, hoping she would just scan them quickly and stuff them in a bag. After the way Tammy was knowingly smirking at me, I felt a little self-conscious buying the things that Dania had sent me for and I just wanted it to be over. Lizzy quickly scanned the men’s items, bagged them and then handed them to me. When she got to the lingerie items though, she slowed down. She looked at each one carefully, holding it up, admiring it, looking at me, smiling, she then said, “Someone’s going to be a very lucky girl, aren’t they?”
I stammered, “I guess so, yeah…”
“Very pretty,” she said, “I wish I could see her wearing them, I bet she looks super hot!”
I just smiled and waited to pay. I slid my card through the slot and signed for all of the items. “Thanks Lizzy, have a great day!” I said as I took the bag and walked away.
“You too, and have a great night!” she said behind me, now giggling as I walked away.
I made my way back to the car and drove quickly back to the office where I stashed the bag full of lingerie in a plastic bin in my office.
When I logged back on, Mistress Dania was waiting for me. "Took long enough!" she typed. "Did you get everything you were supposed to?"
"Yes Mistress, I have everything," I responded.
"Good. Now go to the bathroom and put it on under your work clothes. Hurry up!" she commanded. Soon I found myself in the bathroom with the door locked and panties, stockings and a bra in my hands. I quickly took off my pants and underwear and stuffed the boxer briefs rolled up into my pocket. I stepped into the satin thong and pulled it up quickly. It barely covered my cock and balls and fit tightly around my waist pulling the thong up in between my ass cheeks. I was actually a little surprised at how well it fit. Next I sat down on the toilet and began sliding on the stockings. They felt cool on my legs and the rubber inside at the top of the thigh highs caught into my leg hair a few times. When both stockings were on my legs felt cool and sexy, but I hurried to put my pants back on before someone else needed to use the bathroom.
Lastly, I pulled up my shirt over my head and quickly snapped the bra on and slid my arms into the straps setting it into place. When I got my shirt back on I checked the mirror and there were no signs of my secret undergarments. I flushed the toilet and headed back to the office.
"I did exactly as you commanded Mistress," I typed back into the messenger.
"Good," she said. "Now you will be a good slave and keep it on the rest of the day. On the way home tonight I will have another assignment for you! Keep that little man-clitty cock of your hard all day for me slave sissy-boy! I will be back later on to tell you what you are to do for me."
And with that, she was gone, logged off. I was shocked a little, but she was right, I was really turned on. The rest of my day went as usual with the only difference being my near constant state of arousal. I was always worried that someone somehow knew my secret, but the day passed with nothing out of the ordinary happening. At five minutes before five her name lit up in the messenger window again.
"Did you have an exciting day slave?"
"Yes Mistress, I have been turned on all day," I typed back. I was really curious what she had planned for me.
"I am glad you enjoyed yourself, but this is supposed to be a punishment slave...so this is what you are going to do...."
I waited in anticipation as the messenger window said she was 'typing' and I was growing more and more excited. Obviously she wanted me to do something more than just play in the office for her like I had done before.
"You are to do some research and find what they call a 'glory-hole.' When you find one, I want you to go there after work with your 'sexy' clothes on under your work clothes. On your side of the glory-hole you are to strip down to just the 'sexy' clothes and kneel in front of the hole and wait. You are to suck on any cock that comes through that hole, and you are not going to stop until you make the man cum with your mouth only. Do you understand slave?"
"Yes Mistress," I typed automatically, but I was very, very nervous. What if I got caught dressed up as a woman in a place that would have a glory-hole? I would be mortified.
"Good. Now go do your research and take your punishment like a man. Tomorrow you will tell me all about it. Good-bye for now slave." The messenger sounded like a door slamming shut as she left.
I contemplated just lying about an adventure to her tomorrow so I could save myself the trouble, and the potential embarrassment, but I hadn't lied to her before, and I didn't want to start now. After all, it was my fault that I was late to work, I should be punished for it. I typed 'glory-hole NJ' into Google. I soon found an adult bookstore that guys said had a glory-hole. It wasn't far out of the way on my commute home so I figured I should do exactly what my Mistress commanded.
When I arrived at the parking lot I saw the place. It was called "Peek-a-view" video and the storefront windows were completely blocked so you couldn't see inside. As I entered the store I saw racks of video DVDs and many sex toys of all sorts on the walls. There was a counter in the front with a young girl with piercings all over sitting there watching TV looking kind of bored, and there was a beaded curtain leading to the 'back' where I assumed the videos and the glory-holes were. I made my way to the back and was about to head through the curtain when I heard the girl say, "You can't go back there unless you buy tokens first."
I walked back up to the counter and I asked, "How much?"
"Five," she said.
I pulled out a twenty dollar bill, handed it to her, and she handed me back fifteen singles and a stack of tokens.
"Have fun," she said smiling and went back to watching her TV.
I put the cash in one pocket and the tokens in the other and headed to the back. When I entered through the curtain the first thing I noticed was how dark it was. I waited a moment for my eyes to adjust and then moved slowly down the corridor. There were doors with a light over each one on both sides of the corridor which wound around in a rectangular shape. I guessed there were for booths in the center island and then booths on the outer edge all the way around. At the back of the store there was another entrance, or exit, depending on which way you were going of course, and there was a larger room, which looked like a business office or something.
That door didn't have a light over it.
As I walked through the corridor sizing up the situation I wondered which booths had the glory-hole. Most of them were occupied, some had the door shut and others had guys standing in the doorways smoking cigarettes, hanging around, and there were a few other guys talking to each other in a normal voice. I made my way back to the beginning of the corridor and decided I would try the first room that was open. As I entered the room I saw right away that I was lucky. This one did have a glory-hole about 4 inches in diameter in the middle of the wall separating the two booths. I started to close the door behind me when I felt it being pushed open towards me.
A large guy that I would guess was in his early 50s came into the booth with me. He was taller than me, I am guessing about 6'-2" tall and was really a large guy. He was extremely well built and although it was pretty dark you could see that he kept himself in shape. He started putting tokens into the slot and a video started playing. It was a girl kneeling between two guys with a cock in each hand and she was alternating back and forth sucking on each one.
"My name is Rick," he whispered. "What are you here for? Be honest, tell the truth..."
I don't know what came over me. I don't know why but I trusted this guy. He seemed like a pretty cool guy and I could see his wedding ring, and I just felt comfortable.
So, I told him about the online games and that my 'Mistress' sent me here to suck a cock through the glory-hole in panties, bra, and stockings, and that I was supposed to make the man cum with only my mouth.
Rick sat down on the bench with me standing in front of him between him and the video screen with the glory-hole to his left and said, "Well...you'd better get to it then. I am going to watch you do it. I'll even take a few pictures for you if you want. Go ahead. Strip!"
His words were just like a command and I found myself taking my clothes off. My shirt came up over my head and he held out his hand for me to hand him the clothes and I did as he motioned.
"Very sexy," he said about the bra. "Now the pants."
I kicked off my shoes and as I stepped over towards the glory-hole my stocking covered feet felt something wet and slippery. Rick smiled and said, "There lots of cum on the floor, isn't there?" I nodded feeling the slippery spunk all over my feet. He pulled my shoes under the bench close to him and watched intently as I undid the button on my slacks. I lowered my pants but I was careful not to let them touch the floor. I stepped out of them carefully and handed them to Rick. He folded my clothes neatly and put them on the bench next to him. Then he said, "You look so precious. Can I take pictures?"
I nodded, and he began using a cell phone to take pictures. "Well go ahead. Do what you want to do. Get down there," Rick said with a commanding tone again. I could feel the nervousness in my tummy start to churn more, and I couldn't be more helpless in front of such an imposing man, but now he was going to watch me suck cock right there through that disgusting hole. I squatted down and looked through the hole and I saw a guy standing in front of his own bench slowly stroking his hard cock. It looked about average from what I could see in the dim video light. Rick said, "If you put your finger through, he will stick his cock through the hole for you." So I did as he said, and quickly the guy came to the hole and guided his hard cock through.
At first I gently grasped it with my left hand, steadying myself against the wall with my right hand. I readjusted my squat and stepped in another puddle of cum that squished in between my toes. I gently licked right under the head of his cock and it 'leaped' up. I looked at Rick and smiled, and he smiled back, taking another picture. I felt more comfortable after seeing his smile and opened my lips over the head. The tightness and smoothness of the skin was amazing. I was now feeling totally comfortable with my new friend watching me and the stranger on the other side of the wall so obviously enjoying my mouth on his cock. The stranger began to talk dirty through the wall, "Suck me...that's it... you like sucking cock, don't you? You little slut... you love my cock don't you?"
I mumbled, "Mmmmm hmmmm," with his cock sliding in and out of my mouth.
Rick whispered, "No hands, remember?"
I took my left hand off of the Stranger's cock and just let my mouth go up and down on him at a medium pace. I slowed down to tease him a little and Rick approved with a sigh. The Stranger begged, "Faster please...please finish me off... ugh... ugh... suck it.. come on... make me cum you little slut...." and I began moving up and down on his hard-on quicker. I bent my head down and applied pressure across the top of the head on my up stroke and the Stranger really seems to appreciate this. He groaned and thrust forward against the wall. I took this as a sign that he wanted to go deeper and I thrust my head down on his cock as far as it would go.
I felt the tip in the back of my throat pressing hard, gagging me, but there was still an inch or so to go. A few more strokes with full suction and I felt him start to swell. I could tell he was close, and so could Rick. Rick said, "I think you should swallow that load, don't you want to?" Just then the stranger began cumming with my head all the way down on his cock. I tried to pull back quickly but I felt Rick's hand on the back of my head. The first shot overwhelmed me and I accidentally swallowed a little bit of his cum, but quickly tried to block the rest. The Stranger shot again, and again, but Rick wouldn't let my head off of him. My mouth had filled up with his cum and had just started to drip down the side of his cock when Rick said, "Swallow it all now."
I surrendered to my new friend and just let the cum slide down my throat. My humiliation was complete. I was totally spent too. After I swallowed, Rick pushed me over from my squat position and I landed on the cum drenched floor. I could feel the stickyness and slimyness on my stockings and on my butt. I looked down and to my surprise I had a raging hard-on that was tenting the thong panties. Rick just laughed and then said, "On your feet."
I stood up.
"Turn around now!" Rick said loudly with authority now. I wasn't sure what was going on but I did what he said. "Give me your hands behind your back." Again, I didn't know what was going on but I was getting even more turned on. I heard and felt handcuffs going around my wrists as Rick pushed me into the corner.
"You're under arrest for lewd and lascivious behavior. You have the right to remain silent, anything you say can and will be used against you in a court of law. You have the right to an attorney, if you can't afford an attorney on will be appointed to you by the court. Do you understand these rights?"
"Shut up you slut," Rick said. "My name is Detective Rick, and you are in big trouble. Do you have any idea how much trouble you are in? You are facing six months in jail or a five thousand dollar fine, and you will go to jail tonight. Your wife will have to come bail you out. Do you understand?"
"Yes, what!?" Rick sounded angry now.
"Yes, Sir?" I said questioningly.
"That's right... you call me Sir and nothing else for the rest of the night. Now, do you want to go to jail right now?" Sir whispered, "Or would you like to work something out?"
"I will do anything you say Sir, but please don't take me to jail."
"That's right you don't want to go to jail, because I would have to take you in as I found you, in that ridiculous outfit you have on. Do you want that?"
"No, Sir. Please, anything you want Sir," I stammered hiding my face in the corner.
"Good." Sir grabbed my clothes in a bunch in one hand, opened the door with the other and led me out of the booth into the corridor in front of everyone there. They had come out of their booths to see what the commotion was and Sir said, "We've got a dirty little slut here boys that is willing to do anything we want." There was some commotion and everyone seemed to be heading one direction. Sir led me down the corridor to the back room with the door that had no light above it. The door was open already with many guys standing around looking directly at me. I was so humiliated I kept looking at the floor as Sir pushed me along in front of him.
As we got to the door Sir showed me his badge and said, "If you think you want to stop at any time, just say so, and I can take you out of this mess. Do you want to stop?"
"No Sir. I don't want to stop Sir," I said quietly acknowledging my total defeat.
Sir led me into the room which was larger than a normal booth, perhaps three times the size and there was a table like contraption in the middle of the room. I was like a combination of a chair and a table I think. It had two padded wide flat legs in the front leading up to a table like padded horizontal surface and beyond had two 'Y' like arms projecting out at a fairly wide angle but still horizontal.
These 'Y' like arms had curving tube legs projecting from the front of them and curving back underneath to support them. As I was positioned in front of the furniture I could hear many more people entering the room behind me. My right leg, still in the stockings, was handcuffed to the piece of steel tubing behind the padded flat front leg, and the same followed with my left leg. I was pushed over and my hands were released from behind my back, but quickly they were stretched out along the 'Y' section of the table. My arms were handcuffed to each leg of the table on the other end and my head hung facing the back of the room with my ass facing the door.
"Put a blindfold on him so he can't see who you all are," I heard Sir say, and I felt someone come behind me and secure a blindfold into position.
Then I heard a different voice, "Okay, the store is locked up now." It was the girl from the front. Did she know somehow this was going to happen to me? Was that why she said, 'Have fun?' She was there now.
"Ooooohhhhh, look at how sexy she is in those panties, and the stockings are just lovely!!!" she squealed walking around me. "This is going to be a great video...Go ahead, have as much fun as you want Rick, I am all set up." My thoughts raced. Was she taping this? Oh God, who would see?
Then it began. I felt the first guy walk up in front close to me. He grabbed my head under the chin and lifted my face up and I felt his soft cock slap me in the face. There was laughter in the room and I was trying mentally to count the voices, but I was quickly distracted when I felt in each had another semi-soft penis being pushed. Lastly, I felt someone standing behind me and running their fingertips up and down the backs of my stocking clad legs. I shivered. His light fingertip caresses felt really nice. The man in front of me rubbed the head of his soft cock along my lips and I got the idea quickly. I parted my lips and he thrust it into my mouth quickly. I sucked it in, and let it slide out slowly, getting it wet. Then I started to slowly alternate between sucking in and letting it slide out.
I could feel him start to harden in my mouth and I felt sexy, even though I was in this disgusting place with these dirty men doing anything they wanted to me. I stroked the cocks of the men in my hands and they too started to get hard. Many of the voices in the crowd started to get louder and they were soon cheering me on. The guy behind me pressed his body against my backside, and I could feel how excited he was. He moved the thong to the side and I struggled a little testing my bonds. There was nowhere for me to go.
I felt the head of his hard cock press against my ass and he just held it there. Then I felt a warm wet drop right between my ass cheeks. I guess he spit, because I felt the tip of his cock sliding up and down getting me wet. Then he stopped and pressed it right at the entrance. He went slowly but pushed constantly.
I tried to relax and focus just on the three cocks in front of me. The guy in front of me was holding my head and thrusting his dick in and out slowly but it seemed as if he was trying to make me gag each time. Then I felt the guy behind me push in. It went in quickly with kind of a pop, and there was pain. I moaned loudly, and the crowd of guys cheered, followed by laughter. The guy behind me started moving back and forth slowly at first, and I could feel it burning. I moaned loudly again, and he slowed down. Then he pushed in as deep as he could go and just held it there. The guy I held in my mouth started working it harder and grunted, "I'm gonna cum..." and just as he finished speaking he began pumping his load into my throat. As I swallowed the first spurt the guy behind me grunted and I felt him spasming. I knew he was cumming in my ass.
I felt his weight collapse on top of me for a moment. He stood up quickly and pulled out of my ass with a 'pop.'
The guy on my left moved in front of me and the guy on the right moved behind me, both with their hard-ons that I gave them. New guys with soft cocks moved to their places and again I could feel them in my hands. I felt so sexy that each of these guys got hard, then came because they were touching me. My cock was aching. I wanted to cum so badly. The guys didn't stop soon. It went on for a long time from what I could remember. I counted six loads of cum that I swallowed, and six guys came in my ass. I felt the cum run down my legs so I knew they didn't use condoms. I was totally used and abused by 12 different guys, not including the stranger on the other side of the glory-hole. When they were done, they uncuffed me but Sir told me to keep the blindfold on.
"Now jerk off for us slut boy," Sir said.
I took my aching cock in my hand and began to stroke. The front of the panties was drenched in pre-cum and in no time at all I was cumming. I felt Sir's strong hand on my neck as I finished cumming and he pushed me to my knees, still with the blindfold on.
"Now lick it up you nasty little slut, and I will let you go home," Sir commanded.
I stuck out my tongue and searched the floor for my own cum, listening to the laughter and the cheers as I got closer until I could finally taste my own salty sweetness. I slurped it into my mouth and swallowed. I felt someone push me over on my side with their foot and my clothes fell in a pile on top of me as they all left the room. By the time I got up and dressed the place had emptied out completely. The only thing I had left to do was to tell my Mistress what my punishment was like.