by Anthology
“Good evening Lia, how was your day?”
“I have to be honest with you Sir; it was one of the longest days of my life.”
“I can only imagine Lia. I’m sure it was very uncomfortable; especially with the enhancement cream. What I really want to know is if you understood your punishment and why I picked the pearl thong and the enhancement cream for you to use?”
“Yes Sir, I believe I do. Since I came without your permission, you wanted me to learn how to control my urges and my body no matter how badly I wanted to. The pearls rubbing on my swollen clit all day was almost more than I could handle. I’m sure the whole office noticed how flushed I was and wondered why I was squirming in my chair so much.”
“I’m very proud of you Lia. You did an excellent job and followed my instructions perfectly. Move your camera down and let me look at my beautiful, swollen pussy.”
As I move my camera down, I think how his words make me feel. I’m so happy that I was able to contain myself and do as he asked. That I am stronger than I thought. And how his praise makes me want to please him even more.
“Oh Lia, my pussy is so beautiful. Open your lips for me, but don’t touch your clit. It’s so pink and I can see your juices already running down your thighs. How I wish I could be there right now and nibble on that swollen clit. Take it into my mouth and suck on it gently as I push my fingers in and pump them slowly in and out. I promise you Lia, that will be very soon.”
I have to close my eyes and bite my lip just to keep from coming from just his words. I don’t know how much longer I can last like this.
“Lia?”
“Yes Sir?”
“I need you to open your eyes and listen to me. I know how desperately you want to cum, but your punishment is not quite over. I’m not being cruel, in fact tomorrow you will be rewarded with the most explosive orgasm that you have ever had.”
Oh my God! I don’t think I can take this another day!
“Lia, you can do this. This is all about training your body…mind over matter. I promise you it will be worth it. You have one more box to open in the morning and follow the instructions. Be sure your phone is charged and you take everything from the box with you. Do you understand?”
“Yes Sir. And thank you Sir for the beautiful thong.”
“My pleasure Lia. Now, go to bed and that’s an order because I’m sure you got little sleep last night. Sweet dreams and I’ll talk to you tomorrow night at the same time.”
“Goodnight Sir.”
I switch off my computer, take a big sigh and crawl into my bed. The sooner I can fall asleep the better so I’ll quit thinking about my aching pussy. I turn the lights out, close my eyes and within minutes, I’m asleep.
I awake the next morning feeling a little bit better. At least I know my punishment will be over within a few hours and I’ll get the release I so desperately need.
I head downstairs to open my box. Inside is a gorgeous black glass anal plug with gold filigree lightly etched around the top. Normally I don’t think anal plugs are gorgeous, but this one is and I have to say that I’m a little excited to wear it. There is also a tube of lube and a note from Sir.
Lia, I hope you like the anal plug that I picked out for you. I took great care in finding one that is deserving of your beautiful ass and I hope you enjoy wearing it. Please put it in and do not remove it until we talk tonight. You will need to wear a pair of your sexiest high heels and a short skirt; one that is able to be pushed up to your waist if instructed. Also, no panties are allowed today. At 11:55, you are to open the second note and follow the instructions. I’m looking forward to talking to you tonight and hearing about your day. Sir
Hmmmmmmm…intriguing instructions, but I’d better get my ass in gear, literally, so I can make it to work on time.
The morning goes by quickly since my boss is still out of town and I’m having to do a lot of extra work. The only downside is having to sit so much with this anal plug in, but even that has been bearable and before I know it, it is time to open my second note.
Lia, I hope your morning has gone well so far. Since I know your boss is out of town and most of your coworkers will be at lunch; I want you to go into his office, close the door and lock it. Pull your skirt up to your waist and sit down in his desk chair. Place both of your high heels on his desk and spread your legs as far as they will comfortably go. Put your phone on the desk, making sure your pussy is in full view and press the video record button. I want you to touch yourself slowly and enjoy the anticipation of the orgasms to come. Know that I will be watching you as you cum, making my cock rock hard wishing that it was me giving you such pleasure. I’m sure that after all of your orgasms, the chair will be wet and covered in your juices. You will proceed to get on your knees to properly clean the chair. You are to reach around and grab each ass cheek and spread them so that I have full view of your ass and your swollen, dripping pussy. You will then proceed to lick your juices off of the chair until it is totally clean. If during this time, your juices drip to the floor, you will also be required to lick them up in respect to your boss’s work area. I so look forward to watching this video tonight as I grab my cock and get my own release knowing how much you enjoyed yours. Enjoy and I will talk to you tonight. Sir
Fuck! I’m excited, scared, wet and needing to get up and go before anyone sees me. I nonchalantly walk down the hall to my boss’s office. Luckily no one is around and I slip in, lock the door and take a big sigh of relief. Grabbing the hem of my skirt, I pull it up to my hips allowing the cold air to hit my now very wet pussy making me shiver. I walk over and sit down in his chair. It is big and sturdy and luckily is not made of real leather or has any wheels. Cautiously I bring both of my legs up, anchoring my heels to the edge of his desk hoping that I don’t leave any kind of marks. I spread them as far as I can and place my phone on the desk angling it just right to get the best view of my now very wet, very swollen lips and my very engorged clit that is begging to be touched. Leaning my head back and closing my eyes, I slowly move my right hand down and separate my lips, allowing my juices to flow freely out and down my thighs. I capture some of the wetness and start to slowly circle my clit. My mouth opens and a small whimper of neediness slips out between my lips. My left hand dives into my pussy, three fingers deep. I finger fuck myself hard and deep and fast while I rub my clit adding more pressure with each circle I make. I want to go slow, but I can’t. My need to cum is so great and I don’t think I can last another second. Suddenly my legs start to shake and that feeling of pure ecstasy that starts at your core and shoots straight up through your body begins. My eyes start to roll back in my head and I’m holding my breath trying to make it last. I feel like I am floating outside of my body but I need to stay grounded because I feel another orgasm starting. I can no longer feel my fingers, but I know they are still pumping and rubbing and bringing me to another high. Time has no meaning at this point and I don’t know how long this continues or how many orgasms I have, but I suddenly realize that I am sitting there with my eyes closed and my heart beating and my hands are resting in my lap. Sir was right. I have never had so many intense orgasms in my life. Looking down, I also realize that I am literally sitting in a small puddle of my own juices. I stand up and literally fall to my knees; my legs are still shaking and so weak. Following Sir’s directions, I reach around, grab my ass cheeks and open myself up to the camera. I lean my head down and start licking the chair; lapping at my juices making sure I don’t miss a drop. Of course I still have some running down my legs so when I’m through with the chair, I bend over even further and lick the floor clean. I finish just in time for my lunch to be over and honestly at this point, I couldn’t eat a thing.
That night I click on my computer just in time for Sir to start messaging me.
“Good evening Lia, how was your day?”
“Sir, I have to say that was the most enjoyable punishment I have ever had. Not to say that I don’t want to be obedient and have to be punish
ed, but I did learn something about how to control my body and to make sure and follow your instructions. Thank you Sir.”
“You’re quite welcome Lia and you did an excellent job with each task. I can’t wait to get your video and have a little alone time with myself tonight. I have a late night dinner meeting and have to run, but I’ll talk with you soon. Sweet dreams Lia.”
Over the next couple of weeks, I find my feelings for Sir are getting deeper. He has been so patient with me and my training and I absolutely love it when he calls me his “good girl”. But to be honest, I really love it more when he calls me his ‘fucktoy’ and what he’ll do to each and every hole. It makes me wet just thinking about it. As I sit there day dreaming about being just that; my computer pings and it’s Sir.
“Hey Lia, are you there?”
“I’m here Sir.”
“How’s your day going?”
“Good, I was just sitting here daydreaming about you.”
“Hmmmmmmmmm, tell me about it.”
“Just how I would love to have your cock in my mouth right now and swirl my tongue around the head and dip the tip of my tongue in the slit to catch that first drop of pre-cum.”
“Fuck!”
“Then I would flatten my tongue and lick you from the head to the root while gently squeezing your balls. And then suck your cock all the way down my throat and swallow to make the fit even tighter.”
“Lia!”
“Sir?” Batting my eyelashes with an innocent look on my face.
“My cock is so fucking hard right now!”
“Well Sir if you were here right now, I would gladly take care of that for you. Even slip my pinky in your ass for added pleasure.”
“Lia, stop! You know I am rock hard and I’ll have to excuse myself to go take care of it while watching your office video, which by the way is the hottest video I have ever seen. And since you were being a little brat; I have an assignment for you.”
“Yes Sir.”
“For the rest of the evening you are to walk around your house totally nude. I want all of the window shades open and all of the lights on. At 7:00 I want you to stand at your front window and start touching yourself. Tweak and twist your nipples and make them hard. Finger your pussy and rub your clit until you cum. I don’t care if people walk by or even stop and watch. You are not to move until you are finished coming. Do you understand my instructions?”
“Yes Sir.”
“Lia, I’m not mad at you, in fact I love your sassy side and the fact that we don’t always have to be so serious. This is just another part of our journey together. This is about learning to be comfortable with your body and allowing others to watch. Be brave and enjoy it. I’ll talk to you later tonight and Lia?”
“Sir?”
“I love you.”
“I love you too Sir.”
Luckily I don’t live in a heavily family oriented neighborhood. It’s made up of more young people just starting out in life and older couples who have retired. So I feel a little better about the assignment knowing that I’m not going to scar some child by doing this.
I remove all of my clothing and go around my house turning on all of the lights and opening all of my blinds. My house is older and has mature trees in the front yard. So that should give me a little protection from prying eyes, I hope.
I decide to put on some music; something that will get me in the mood. Close to You by Maxi Priest is perfect. A great beat but so sensual in both the music and the words allowing me to be brave enough to approach my front window. Closing my eyes, I lose myself to the music and block everything else out. Automatically my hands begin a slow journey down to my breasts and start circling my nipples, slowly moving in until I reach the tips. I start pulling and twisting, working them really hard; so hard that my eyes fly open and suddenly notice a couple walking down the street. I’m frozen in mid twist and hold my breath. They are so engrossed in their conversation that they don’t even look my way. Fuck, that was terrifying, but at the same time, I’m a little turned on thinking they might have seen me. Maybe there is a little exhibitionist in me. The music is still going so I start again. It doesn’t take me long to start tweaking my nipples and swaying my hips to the music. I’ve got both hands working my pussy when I look up and see the creepy, old man staring out his front window at me. Again, I stop mid stroke and just stare at him. What the fuck do I do now? Sir told me to keep going even if people stopped and watched. If this creep wants to watch then I will give him a show. I slide my hand back down to my pussy and start to rub my clit. When I look back up he’s gone. What the hell is going on with this guy? At this point, I just want to finish my assignment. So for the third time I start again, although my heart just isn’t in it anymore. I close my eyes so I don’t have any more distractions. Finally, I feel the start of my orgasm and with it comes a breathtaking release. I lean my forehead against the window trying to catch my breath and thanking God that no one saw me. Well, no one but that creep across the street. As soon as that thought comes into my head, I look up and see him standing at the window and this time he has binoculars! What the fuck is going on with this creep? If I had known that he was back, with binoculars no less, I would have done everything I could to cum faster and get the hell away from the window. My feet can’t get me to my bedroom fast enough. I throw on my robe and get on the computer to see if Sir is there. I need to talk to him. I need to feel safe. I type in his name and hope and pray that he is on.
“Sir, are you there?”
“I’m here Lia. How are you sweetheart?”
“Sir, I just need you to talk to me please.”
“Lia, what’s wrong? What’s happened? Are you hurt?”
“No Sir, I’m not hurt, I’m just scared.”
“Lia, tell me exactly what happened and don’t leave anything out, do you understand?”
“Yes Sir. I was in my front window doing my assignment when a couple walked by, but they didn’t even see me. Then I looked up and saw the creepy man who lives across the street watching me. Well, I thought if he wanted to watch, then I would give him a show. So as I continued; he left. I thought that was the end of it until I finished and when I looked up, he was staring at me again, but this time with his binoculars. It shook me up. He’s lived there a lot longer than I have and he’s never done anything to me other than to smile and wave, but still he just gives me a creepy feeling.”
“What does he look like?”
“Well, he’s older and bald and a little overweight. He’s not bad looking, it’s just the feeling I get and the way he stares at me.”
“Lia, I want you to make sure all of your doors are locked and bolted, your windows are locked and when you go outside; be aware of your surroundings. He sounds pretty harmless to me, but you never know. He probably sees a pretty young girl and wishes that he was young again just to have a chance with you. But, if he starts acting stranger or gets out of line in any way, I want you to contact me immediately and I will handle the situation. I will not allow you to be hurt in any way Lia. I want you to feel safe and protected at all times.”
“Thank you Sir. I appreciate you being there for me and making me feel so safe and protected.”
“Lia, as your Dom, that’s my job. It’s not all about the sex, although that is a big part of it. It’s also about making sure you are safe and happy and supported in your decisions. Now, it’s been a rather long day, so I want you to make sure everything is locked up and you go to bed. That’s an order. Is that understood?”
“Yes Sir and thank you Sir. I am exhausted. Goodnight Sir.”
“Goodnight Lia. Sweet dreams.”
CHAPTER THREE
“Good morning Lia.”
“Good morning Sir.”
“Have you been using the anal plugs that I sent you; going up in size every three days?”
“Yes Sir I have, although they are getting um rather large and a little uncomfortable.”
“Lia, I assure you, when my cock f
ills your tight, little ass, you will be so grateful that I made you wear those larger plugs. Your ass will thank me also. I know you’ve never had anal before and are a little scared at the thought. That’s why it’s so important to take it slow and prepare your ass for the first time. I promise you it will be a lot more enjoyable if we do it this way.”
“Sir?”
“Yes Lia.”
“Are we ever going to get to meet in person so we can actually have anal sex? I mean, I love talking to you every day and all of the assignments and you getting to watch me, but I would really like to progress to an in person relationship, not just an online relationship.”
“Lia, you know one of the reasons why I chose to have this type of relationship is because of my work schedule. I travel so much that it would be nearly impossible to set up in person dates.”
“But Sir, I know you live in San Antonio, which is not far from me, and I could be waiting for you naked and in your bed when you arrived home. You would not have to do a thing except lay down and enjoy the ride. Wouldn’t you love to wake up with a warm mouth wrapped around your cock?”
“Oh Lia, of course I would. There is nothing more I want than to have you in my bed, thrusting my cock in that wet pussy of yours. Maybe one day we can change the course of our relationship, but at this time, I just don’t see any other way.”
“But Sir, I can only learn so much over the computer. I really want the whole experience where I can actually feel your touch and not just imagine it.”
“Lia, I understand your point, but hun at this time, there is nothing I can do to change it. Are you having second thoughts with how things are between us? I need to know if you are.”
“No Sir, no second thoughts. You know how I feel about you and the trust between us has only grown. I just want to feel the intimacy between us. I know it will be unbelievable and it will truly tie us together in every way.”