Sexual Fantasy

by on Aug.03, 2009, under BDSM

The relationship I used to call my marriage had ended just over a year ago and my 44th birthday was a few days away when Jessica walked into the office. As a lawyer who had gone through a publicly humiliating divorce and been shunned by most of polite society in town, seeing her in the office elated me. 

The thought quickly passed through my mind that perhaps people were forgetting and the upscale clients I had lost were considering returning. While lots of other professionals get divorced every day not too many face public accusation of being addicted to kinky sex.

I had been using the internet for years for what I thought was safe exploration of fantasies. However, the more I explored porn sites and visiting adult chat rooms the less interested I became in vanilla sex with my wife. Things in the bedroom had never been what you read about in Penthouse forum letters but it was more pleasurable than just whacking off alone. A continued lack of interest in sex on my part prompted my ex to hire a PI. 

While I had never actually had an offline experience my online and phone sex activities were tracked down and thrown in my face right after she filed for divorce. Even though nothing specific about what the PI discovered appeared in the divorce records Kathy initially made sure that everyone knew I was “addicted to perverted sex”. As a result I agreed to a very generous settlement, got a restraining order against her from discussing me publicly or privately and began rebuilding what was left of a once flourishing law practice.

Jessica was a lovely woman a few years older than I was. When I was married she and her spouse traveled in the same social circles we had engaged in superficial cocktail banter over the years. They had what appeared to be a rock solid marriage, but as a lawyer I learned that what you see from the outside is often the worst indication of what is going on behind closed doors. 

“Jessica it is so nice to see you again but I must admit I’m a bit puzzled as to what brings you in here.” I told her as she sat down in the chair across from my desk.

She appeared uneasy and hesitant at first but mumbled a polite response to my initial greeting. When I asked her what brought her into the office she evaded the question completely and began quizzing me about the attorney client privilege with several questions about what office staff knew about open files. I spent about 15 minutes explaining things to her and repeatedly assuring her that whatever a client tells an attorney remains a secret and that upon a clients request office staff can be kept in the dark if need be. Despite this it was not until I assured her that an attorney could loose his license for disclosure of things a client requested to remain confidential that she relaxed.

“Tony, I have not actually done anything but I must admit I have been considering having a fling. The problem is that I think my husband has hired someone to spy on me so he can leave me penniless. I need to know if he has hired someone and if so what I can do about it,” she blurted out rather quickly. “I hope you don’t mind but I know you have had some “experience” in with this and you were the only person I felt might be able to understand and that I could trust and who might be able to help me.”

A few days later Jessica was seated across the table from me and was as nervous and fidgety as on her initial visit to the office. I decided it was best to put her at ease right from the get go. 

“Well there is absolutely no evidence that your husband has anyone following you or has been tracking your activities.” She visibly relaxed when she heard that and I gave it a moment to sink in and let her enjoy the relief. “However,” I added “the PI did turn up some things that could be hard to explain.”

“Oh? Like what sort of things?” she asked with a hint of trepidation in her voice.

“Nothing serious but you recall when we asked to look at your computers?” She nodded and waited for me to continue and hesitated to let it sink in and get a better idea of how to bring this out. “Well the history on those showed some rather interesting web sites that have adult erotica or pornography on them.” 

“Oh that must have been the kids playing around and surfing when nobody was looking.” she blurted out quickly. I knew her children and while kids do surf the net I knew they were not the culprits in this particular case.

“Now Jessica one thing you have to know is that you can trust your lawyer and you aren’t telling me the truth about that are you?”

“What do you mean?” she stammered.

“Well not all the records on the computer showed it was just web sites that had been visited. Do the names HotBytch or SubmissiveMilf mean anything?” I asked in my most professional tone.

There was a long pause and the she said “I had no idea that those things could be traced. I was just exploring and playing around a little. You understand about that don’t you?” I nodded and she said “All of this remains confidential and you can’t tell anyone about it right?”

“Everything remains between you and me on this Jessica. I did not let the staff see anything that I was furnished with so we are the only two people in the office that are aware of it.”

“Well I’m glad that I don’t have anything to worry about.” she added with a sound of relief in her voice. I let her sit for a few moments before I continued.

“Jessica, there is one other thing that I need to make you aware of.” Her eyebrows arched when she heard me say this and she got a little tense. I let her sit for a moment and then said, “Your cell phone records have a lot of what could be seen as suspicious calls.”

“Oh really? Suspicious in what way?”

“I don’t know exactly how to put this so may I just be blunt at the risk of offending you?” She nodded waited for me to continue. “Several times a week you were making or receive phone calls to out of state numbers. When these numbers were checked it showed they belonged to men. Based upon the time of the calls, the length and the frequency it appears that you are having what is commonly called phone sex two to four times a week while your husband is at work.”

“Oh GOD! If Jeff ever found that out he would never understand. It wouldn’t matter that I hadn’t done anything. He is so uptight about sex and anything associated with it and this would be too much for him.” At this point she was visibly upset and seemed about to loose her composure.

I started off with the computer and told her that it would be a good idea to keep the history of it clean. When she looked at me quizzically I took a few minutes to show her how typing in a web address stayed in the browser list until you cleared it out. Then I showed her how to keep the temporary file clean and tell tale cookies deleted. 

I was quite professional but made a point of going to one of the D/s sites she visited to show her how it left traces on the hard drive. It only took a moment for her to learn how to keep chat programs on the local disk and not put icons anywhere on the computer that could be accidentally clicked and to make sure that any names she used were not remembered on her system.

After computer class 101 was over she understood how to keep things from being discovered there and she asked about the phone records. I explained that past phone records were what they were and could not be changed. I did tell her that if she didn’t want her future calls to be listed by number that she could do one of two things. Make sure that callers she didn’t want anyone to know about used *69 to hide the number or that each of you use a calling card. 

To cover up any questions about who she may have been talking to it was suggested that she have a friend she could use as an alibi and if questions were asked about the outgoing calls to a card number just say she thought it wouldn’t count against her minutes.

We wrapped things up when she expressed how grateful she was at how the matter had been handled and trusted that I would keep her secrets safe. With that she began to walk out and I stood there shamelessly ogling her still tight ass under the smooth fabric of her dress. She turned quickly as she got to the door as if to say something and caught me staring at her. 

It was obvious I had been eyeing her but rather than say anything she put a finger to her lips like when you are telling someone shhh and walked out. It would be several months before I saw Jessica again.

It was the middle of October when I noticed that Jessica had made a late afternoon appointment and I wondered why she was coming back in. It had been back in the spring when she was last in the office and I had not seen her on a personal or professional basis since then. I will admit that a couple of times after our initial meeting I had gone on the net to see if I could find her playing around under one of the names I had for her online fun. 

While the names initially had profiles associated with them the profiles were gone within a few weeks after I met with her and I was never able to see what she was up to. She came in right on time dressed to the nines and looking incredible. I put on my best professional face, showed her in and asked her what I could do for her.

“Tony I wanted to let you know how much I appreciated your professional discretion since I was in her last spring. I really wasn’t sure about not letting anyone know the nature of the business I had with you but I am completely satisfied you kept your word and nothing leaked out” she told me.

“Jessica” I said and pointed to my degrees and license on the walls of the office, “had I breathed a word of what you came to be about those documents on the wall would have been recalled by the Supreme Court and I would be in a different line or work.”

She laughed and saying “I knew that but I had to be 100% sure and you passed the test.” Test. I asked myself? What the hell was she talking about? I didn’t have to wait to long as she continued. “Tony I need to tell you something and I expect what I’m about to say to remain in strict confidence.” 

She looked at me for an answer and after I nodded my assent she continued. “You have known Jeff and me socially for years and you are aware of how successful he has been with his insurance agency. It has paid for country club memberships, the best schools for the kids, a beautiful home, nice cars as well as a couple
of cosmetic surgeries for me.” 

I was aware that Jessica had gotten a boob job a couple of years back and took just a second to let my gaze drop to her well rounded and full breasts. She noticed and continued, “Beautiful aren’t they?” point to her tits. “I had these done hoping that Jeff would take more interest in me but it was a lost cause. For years I have lived in a marriage that provides me with all the material luxuries most young girls’ day dream about, but it’s come at a price.”

I sat there and listened as she spoke of a marriage that was seemingly devoid of passion and intimacy. Her husband loved to show her off, take her places or let her be the charming hostess for their friends but that was about the depth of their relationship. His life revolved around his business, the golf course and college football. 

She had tried everything to get him to pay more attention to her and her needs but after 20 years and no results she had resigned herself to live a financially comfortable but emotionally and sexually unfulfilling life. To be honest it was a story I had heard before but usually in the context of someone going through a divorce and that wasn’t the case here.

“Jessica, I don’t know exactly where this is going or what you may need my services for. I am not a marriage counselor. I am a lawyer and I learned a long time ago that my business was more concerned with busting fences than mending them.”

“Be patient with me a few more minutes Tony and I will explain everything. When I am through I will tell you what I need from you and will give you a day or two to think about things before you decide. Okay?” I nodded and she continued. “I am not interested in marital counseling. My lot is cast and this is the life I intend to live as long as possible, but quite simply it’s not enough. 

“A few years ago I started using the internet at home for e-mail and ordering things. I got a lot of junk mail about sexually oriented material on the net and finally decided to just take a look at some of it on a lark. It did not take long until I had a sexual reawakening and got a taste of the things I was missing in life.”

“Initially it was enough to surf a few adult sites, read erotica and let what I discovered there add fuel to a rapidly expanding fantasy life. It was not long before I discovered chat rooms and the cyber sex that is associated with those places. It took me a couple of years and hundreds of requests to have phone sex with someone before I decided to try it. I hate to admit it but I was hooked on the sexual high I got after the first time I talked with someone on the phone and masturbated with and for them.” 

Her admissions were taking me totally by surprise but I knew exactly what she was referring to from personal experience. “I have fended off more offers for illicit offline meetings than I can count but I find that I am drawn more and more towards those thoughts becoming a reality. The problem is that it is just too damn risky. I don’t want to jeopardize the life I have pursuing sexual fulfillment. I think you know that the costs of that can be especially high.” 

“Yes Jessica. Pursuing those desires can be quite costly in the wrong circumstances. I’m reminded of that every time I make the payments on the mortgage taken out on this place to pay Susan’s share of the property settlement and mail out those monthly alimony checks to her. But I still am not exactly sure of where all this is going.” I said in complete confusion.

“Tony, I want to have an affair but I need to know that no matter what happens it will be nothing more than the pursuit of sexual thrills and that the chances of anything being discovered are virtually eliminated. The problem is finding a man who is able to keep things totally discreet and be open to exploring sexual fantasies and taboos as a consenting adult and not get all mushy and fall in love the first time he gets his cock sucked.” 

I sat there in utter disbelief that she was revealing all this to me and then the shock set in when she dropped the bombshell. “Tony, I think you are THE man I want to have that type of affair with. No strings attached, no promises, no tomorrows, just pursuit of passion and desire with no limits or holds barred. Does that shock you?”

I sat there in my chair with thoughts racing through my mind at a million miles a minute. Why me? Is she serious? Jesus most guys would give their right arm for an opportunity like this! Is she for real with what she is saying? The list went on and on. “Jessica, I’m quite flattered at what you have said but honestly I don’t know how to take it.”

“I didn’t expect an answer right now and knew this would come as a total surprise Tony.” she said with a wicked grin. “But you need to realize I’m quite serious in what I have said. Since I was in her last I did some checking up on you too. I know that you aren’t currently seeing anyone and as far as my PI could tell you have not had a one night stand since you and Susan divorced. That is important to me because the last thing I need to have to do is explain how I contracted an STD to my husband.” 

While what she said made me a bit uncomfortable it was true. I had not had sex in over a year since my divorce and had been hesitant about getting into the dating and bar scene locally after what I had been through.

“Tony here is the bottom line. I want to us to use each other and explore all of our sexual fantasies. I’m not looking for love here. I just want a man who is not afraid of his desires or a mature woman’s sexuality and is willing to pursue things wherever they may go. 

“There is not a man out there who doesn’t dream of finding a woman to do the things with that I’m offering to you. The problem is that most either can’t find it or are afraid to follow up on it. I am going to leave you now with those thoughts and this package,” she said as she placed a manila folder on my desk. “Read what is inside and consider it for a couple of days. If you are mature enough and willing to meet my needs let me know. If not I trust that you will forget this meeting ever occurred and destroy the contents of the folder.” 

Before I could say a word she abruptly got up and left, leaving me in a state of total confusion and bewilderment. After Jessica left I spent the last few minutes of my day returning phone calls and checking my calendar and files for the next day. When the office staff left I was left alone at my desk with the folder sitting there before me. I opened the top and pulled out a set of smaller numbered envelopes. They were numbered from one, two and three, with a note on number one that said read me first. I opened it and pulled out the note.


If you are reading this you have gotten over your initial shock and opened the first envelope. I can’t believe that I actually went through with this but I had to find someone that I thought understood and could be trusted with my innermost secrets. I hope that my initial trust was not misplaced. I need a man. Not just any man but a man who understands that a woman has the same feelings, desires and passions that he does and is not afraid to accept her and what she has to offer and
still be able to respect her as a human being. Women are taught that nice girls don’t do certain things. 

The result has been generations of females living out their lives afraid of their own sexuality and clueless as to how to pursue it. Men tend to be so uncomfortable with the desires and passions of women that when they are confronted with it they resort to calling her names like slut or nympho to hide their inability to understand what she needs or to hide their own inadequacies or fears of being able to satisfy her. 

I do not believe that you are the type of man who is afraid or doubts his abilities. The second envelope contains a list of things that I want to experience and some of my most private sexual fantasies. If you can’t keep all that I am willing to share with you hidden please don’t open either of the other two envelopes. I will write this off as nothing more than a case if bad judgment on my part and hope that you will pardon me being so forward.


After reading the first envelope there was no way I was not going to open the other two no matter what my decision wound up being about Jessica’s offer. The second envelope contained a detailed list of Jessica’s sexual desires, fantasies and things that she wanted to at least consider trying. Reading them piqued my curiosity as well as amazed me that a woman so beautiful prim and proper could express much less be willing to act on thoughts that most would find so naughty. 

The last envelope contained a contract. It was titled contract between consenting adults. Reading it I realized it was similar to the slave contracts I had heard about with some apparent modifications. The gist of it was that I was going to be allowed to assume sexual control over Jessica, keep our relationship discreet and with the exception of acts that involved children, scat, blood play or left permanent marks there were to be no limits to our sexual play. 

There would be discussions of what we would try to make sure we both understood the parameters of any play engaged in. If she ever used the word pepper during our play that would served as a safe word and result in a time out. A Post It note was attached to the contract that said if I was in agreement to set her up for an appointment and we would both execute it.

I had a good idea of what all this meant and took the next couple of days thinking about it and doing some reading online about D/s and bdsm relationships. In addition I visited a few chat rooms where there were some discussions held and asked more than a few questions to those in there. 

I discovered that while this was supposed to be a so called “lifestyle” that was open and accepting to all types of relationships that involve a power exchange that a good many people out there were more interested in pushing their own points of view or agendas. 

I decided to take Jessica up on her offer but wanted to make sure that it was what I wanted and suited my needs as well as hers. With that in mind I set her up for another late afternoon appointment the first part of the following week.

When Jessica came in we were both a bit nervous and fidgety, like a couple of school kids at their first boy girl dance. I started off by stating some obvious things, “Jessica we are both consenting adults here and I think we understand that the type of relationship we are apparently getting into is not one that most people in the main stream understand at all. In fact I don’t understand it completely and this is something that we are going to have to sort of find our way through together.”

“I agree with you and have enough trust in you to see if this can work out.” she said.

“Fair enough, but there are some things I want to be clearly understood before we go any further. Ready to hear what my requirements are?” she nodded in agreement. 

“The first is that either of us can always decide that it is time to end the relationship and when that occurs we walk away, no questions asked. While we are having this relationship we both need to make sure that there is not a spillover effect into our public lives that could jeopardize either of us. By that I mean we are going to have to box this up and pretend it doesn’t exist when we are not engaged in sexual play. I don’t want anyone to see something that would arouse suspicions if our public relationship with each other started to get real chummy.”

“I agree with you totally.” And then Jessica added, “But I also want to know that no matter what we will always be honest with each other about whatever is happening. This is all quite heady for me and I could not continue if my trust was violated and I don’t think you could either.”

“Trust and honesty between us is something that is going to be essential if we are going to make this work,” I told her. 

“Okay, it sounds like we are on the same page then. Anything else you can think of?” she queried.

“There is one last thing that I have given a lot of thought to and I hope you don’t have a problem with it. It deals with how we will know whether or not it’s a good time to play or not. If I am interested in engaging in some form of sexual play with you I will ask you ‘Missy, do you have a few minutes?’ and if you are interested you should say ‘Sir, do you have a few minutes?’ If it is a bad time for either of us then we just box it up until another time.” 

She was agreeable to all of that and we both then signed the agreement. I spent the next 10 minutes just talking in general terms with her about schedules, good times, bad times and places we felt comfortable using for our play time. It was after 5:00 and the office staff had left a few minutes earlier and I knew we were alone and would not be disturbed. 

I stood up and looked at Jessica and asked her, “Missy do you have a few minutes, right now?”

“Oh God YES! I was wondering when I would hear those words for the first time,” she said breathlessly.

“Then I want you to stand up for me and do only and exactly what you are told to do.” 

She got out of her chair and stood there facing me for a few moments. As she rose and stood there I took all of her in for just a moment before continuing. There she was with blonde hair, blue eyes, 36 to maybe 38 D breasts, five foot three, about 135 pounds, in a linen skirt and pale colored blouse almost panting as she waited to see what came next. “Tell me how aroused you are right now young lady.”

“Very.” she said softly with her head lowered a bit.

“Tell me exactly what you are feeling now.”

“It feels like my heart is beating a million times a minute and I’m am both embarrassed and totally turned on standing before you right now. I don’t know that I have ever been this sexually excited before in my life.”

“Describe that sexual excitement for me.”

“My nipples are so hard and sensitive right now them just touching the fabric of my bra is making me hotter. The crotch of my panties has gotten so wet it almost feels like I peed in them and there is more moisture dripping out as I stand here.”

“Take the backs of your hands and run them lightly over your nipples for me.” As soon as I told her that her hands went instantly to her tits and began rubbing across her extended nipples. I let her enjoy the feeling of her hands coupled with being watched and told what to do for a few minutes before anything else happened. 

“Now, turn your hands around and begin to lightly pinch and rub the nipples through your shirt.” A harsh intake of breath followed her fingers taking her nipples and starting to squeeze them. I sat there for a few more moments just watching her, noticing that her hips had begun to move slightly back and forth as she stood there. 

“Look in my eyes.” I told her. “Now take one of your hands and begin to lower it toward your pussy for me.” I noticed her hand moving down as she continued to stare at me hungrily, but even if I could not have seen her hand the look in her eyes left no doubt as to the exact moment she touched her sex. 

“Uuugghh,” was all she could moan when her pussy felt the pressure of her hand through her clothing. Her hips were moving back and forth more noticeably now and her mouth had opened a bit as she had started to pant. 

“Oh God that feels so good,” she said as her hand made a tight circular motion in the fabric that had been pushed up between her legs. I still just watched her as I felt my cock expand to its full length of just under eight inches.

“Your pussy is wet and about to explode, isn’t it?” I asked as I stared into her eyes. She could only nod her head as she continued to rub herself. “You are going to need to cum soon aren’t you Jessica?”

“YES!” she replied through clenched teeth.

“You are not to cum until I tell you to, understand?” And she nodded her head quickly to let me know. She continued to rub herself as she spread her legs apart further. Her hand would rub in a tight circular motion right where her clit was located for a moment or two and then she would run it back towards her ass and bring it back to the front in one long slow motion that applied pressure to her open and wanting hole.

“Oh please. I need it now. Let me cum,” she begged. I told her to wait until I gave her permission and then she would be allowed to cum. For the next minute or two her hips were gyrating against her hand and I could tell if I didn’t let her cum she was going to explode on her own right in front of me.

“Now Jessica. Cum for me NOW!” When she heard that I watched in amazement as her hand began to move rapidly between her legs, giving her pussy the stimulation it was screaming for. It only took a few seconds before the first wave of her orgasm wracked her body.

“YES! OH GOD, YES! RIGHT THERE Tony! I’M CUMMING FOR YOU, RIGHT THERE!!” she said in a voice so loud it was a good thing the staff had left for the day. Anyone who had been in the office would have been able to hear her and even with the walls muffling the words there would have been no doubt from the tone in her voice what was happening behind closed doors. 

I sat there rubbing my cock through my pants while she twitched and contorted as her orgasm began to subside a bit. Her hand remained between her legs moving only slightly now but those slight movements provoked a response that continue for force her hips forward and back toward and away from the source of her pleasure.

“I can see you enjoyed that, but you haven’t had enough yet Jessica.”

“Damn!” she hissed through her teeth. “I can’t believe how incredible that felt and you are right, it isn’t enough for me yet.”

Several years ago I had a client build me a large wooden desk when he had trouble paying his bill. It was a sturdy piece of furniture that was large enough for me to lay the contents of a file out on the surface. With the exception of a desk blotter, a pen holder and a few other office items I made sure that it stayed clean so that clients wouldn’t be able to see files or documents belonging to other clients. 

I quickly cleared those away as I told Jessica to take off her shoes. After the desk was clear and her shoes were off I sat down in my chair and pushed it back a few feet. “I want you to get up on the desk for me now Jessica.”

It took her only a moment to climb up and after a tentative strep or two to verify it was steady she looked down at me. I started to lightly rub the head of my dick through my pants again and told her to begin to unbutton her shirt. She caught on quickly and began very slowly, alternating buttons until only the one in the middle remained. 

She looked at me and hesitated until I nodded to let her know that the last one needed to be undone as well. Instead of opening her shirt completely she pulled the ends closer together, holding one side in each of her hands. I was enjoying the teasing when she stopped for a moment and knelt down on the desk facing me and then slowly began to open the blouse. As the fabric was slowly pulled to the side her breasts came into view.

It was obvious she had excellent taste in lingerie and the bra she had on looked like it came from an upscale women’s shop. The fabric was blue and just sheer enough that you could see her nipples through the fabric. Jessica just sat there for a moment letting my eyes feast on what was before them. When I looked up again at her face I could tell she was waiting on me before anything else happened. “Stand up Jessica and let your blouse fall of your shoulders.”

That was all it took to spur her on and I sat back and quit rubbing my cock for a bit and she turned into my private dancer. The blouse fell silently on the desk top and she looked toward me for encouragement. A nod was all she needed to continue. Her sheer bra showed her hard nipples and she soon was rubbing them and her hips were gyrating in what appeared to be pure pleasure. I nodded at her again to let her know she needed to keep going.

Her hands began to run across her tits and abdomen, snaking lower and lower as she wiggled in front of me. She gripped her skirt in one hand and started to pull the hem up slowly. From the way her hips were moving back and forth I could tell she was enjoying being watched and totally aroused by what we were doing.

“Jessica, take off the skirt for me now!” The words were barely out of my mouth and she had unhooked it and unceremoniously dropped it on the desk at her feet. The panties she wore matched the bra and were the high cut French kind. I looked between her legs and could see the crotch piece was wet and pressing between the lips of her open pussy. Her fingers went quickly to her sex rubbing her clit and pressing the fabric deeper into her pussy. I could hear her breathing quicken and start to come in shorter gasps, signaling she was about to cum.

“Stop now!” I told her as I looked into her eyes. She hesitated as if she were going to continue so I told her again “STOP!! NOW!!” Her hands went to her sides and I watched her as she stood there with a bitch in heat look on her face. She was looking at me quizzically waiting and wanting something else. 

I stood up and walked around my desk just taking her body in. On my second time around I told her to kneel with her face pointing toward my vacant chair. I walked around behind her and looked at her round firm ass and the crotch and how the panties were pressed tight into her pussy. I reached up and pulled the panties down, exposing her ass and pussy to the air. 

When she felt the panties being pulled off she started moving her ass back and forth slightly. There was not a hair to be seen from the top of the crack of her ass to the front of her pussy and her current position all of her charms were exposed for my hungry eyes. The lips of her pussy were open showing the entrance to her cunt covered with her own juices. Where the lips met at the top they were just far enough apart to see her clit standing out all hard and deep pink in color. When I looked back from her clit her asshole sat there all nice clean and puckered and I could not resist reaching out and stroking everything I saw.

As my fingers played in the space between her asshole and clit she kept pushing back trying to get me to insert something into one of the waiting holes before me. I toyed with here until I sensed her body approaching another orgasm and then quickly withdrew my fingers. “You did not listen to me very well earlier did you Missy?” I asked her.

“No sir, I thought I had done EVERYTHING you wanted me to,” she replied.

“Think back. How many times did I have to tell you to quit rubbing yourself?”

“Two.” she said in a crestfallen voice.

“Are you such a slut that you cant control yourself and do what you are told when your cunt is all wet?” I asked as I put a hand on one cheek of her ass. 

“It felt so good that I got lost in it all. It was so intense and I was so close.”

“You need to be taught to heed what I tell you and I’m going to punish you for that young lady. I am going to give you six swats on the ass and I want you to count out each one as you receive it. Understand?” She nodded her head in agreement and I gave her the first one across the cheek of her ass and heard her say one as soon as she felt the sting. 

I stood back just a bit and waited to see how red the flesh was going to get. While my hand did not leave a complete imprint on her ass there was a nice spot quickly turning pink. I waited a bit so that she could feel and enjoy the sting that comes after a good pop before I continued.

The next three swats were on different areas of her ass. Combined with the first most of both cheeks had turned a nice rosy color and I was enjoying the control I was exerting over her almost as much as she was. I say almost because as I watch her I could see her juices start to run out of her pussy and drops had formed on her lips. A few had fallen and were now on the top of my desk adding to the aroma of raw arousal coming from between her legs. 

Before the next swat I placed a finger at the opening of her pussy and teased her a bit with the finger tip. Each time she pushed back I made sure not to let my finger go, keeping it in contact with the outside of her wanting sex. I took a second finger now and place it next to the first and began moving them back and forth over her well lubed pussy. Every so often I would brush them up against her clit and it would almost send her over the edge. “You are not to cum until you are given permission. Do you understand?”

“Uh, uh,” was all that she could say in her current state of arousal.

I took the tip of one finger and placed it at the opening of her pussy while placing the other against her tight little asshole. After placing one hand in the small of her back I started to pull her slowly back toward my fingers, making to keep them as close together as possible. Both fingers started to gain entry and I was surprised and how tight both holes were. I could feel the muscles in each hole spasm slightly as the fingers slowly moved forward. When I had both of them in as deep as I could go I just held them there enjoying the wetness, heat and the light fluttering around them. I drew them about halfway out and paused, watching her wiggle her ass back and forth to get some movement inside her hungry body. 

My other hand left her back and came down hard on one cheek of her ass as I shoved both fingers back deep inside of her. The combination almost proved to much so I left my hand on her ass to keep her still. Her head had lowered during this but she looked back between her breasts and breathed “Five”.

“I am going to slowly finger fuck you for a bit Missy. You are not to cum until you feel the last blow,” I told her as I started to move my fingers back and forth gently inside of her. She had started moaning a bit and the smell her sexual fluids permeated the room. I began moving my fingers in longer strokes making sure to keep them at the same slow pace initially. 

I watched as her lips clung to my finger as I would pull it out and would then watch her asshole greedily suck the other one in on the forward stroke. Her breathing had gotten rapid and she was just sucking in air through clenched teeth as I picked up the pace of the finger fucking. Her head was on the desk and she was moving back and forth trying to push my digits deeper inside.

I paused for a second as I drew my fingers back so that just the tips were inside her and placed a third finger beside the one in her cunt. I raised my hand above her ass and brought it down hard shoving the one finger back deep in her ass and letting her enjoy the additional one going into her pussy. As I held my fingers deeply inside of her I felt her sphincter tighten around the finger in her ass and begin squeezing it as the waves of her orgasm started sweeping through her body. 

“YES! FUCK! RIGHT THERE RIGHT THERE!” she started screaming. She let out a loud groan, her pussy clenched down on my fingers and I felt liquid gush out soaking my fingers and hand. She laid there with her head on the desk, ass in the air gyrating wildly seemingly lost in the throes of passion. 

I wasn’t sure if she was having multiple orgasms or just one very long and intense one but I kept my fingers deep in her until the waves of pleasure began to subside. I removed my fingers from her and she almost collapsed on the desk and lay there prone in the puddle of her own fluids that had formed on the top. As exhausted as she was there was one last thing that she was going to do no matter what.

My cock had been sporting a raging hard for the last fifteen or twenty minutes. After watching her reaction to the finger fucking my balls had already drawn up close to my body and were ready to pop. I walked back around to the front on the desk and stood there with my crotch about level with her head. 

She looked up as she heard my zipper come down and did not hesitate to take the head in her mouth as I pointed it towards her. Her warm wet tongue starting gliding over the head and my hips began to move back and forth immediately. She felt how close I was and began sucking in earnest to get me to release into her mouth.

Her tongue began moving back and forth on the sensitive underside of my cock and on each stroke up the tip would dip into the slit and wiggle. She began moving her tongue faster and soon my breath was coming in short gasps as I felt the pressure quickly build signaling my balls would empty in a moment. The first hot white spurt hit her tongue and we were both suddenly moaning. 

Each jet that came out caused my hips to press forward as if I wanted the end of my dick to hit her tonsils and the way she was using her tongue felt so good it was almost to the point of being unbearable. She kept sucking and I could feel her mouth filling with my cum with just a little dribbling out the side of her mouth. She continued to suck until there wasn’t a drop more that was going to come out into her overflowing mouth.

As soon as the last spasm had stopped she eased my cock out of her mouth keeping her lips pressed around it until it was completely out. She then turned her head and looked up at me. I watched as she opened her mouth to show me the load I had deposited and used her tongue again to swirl it around and over her teeth. 

The amount of cum was almost more than she could contain and it looked like her moving it around would cause it to spill out. With her mouth wide Jessica opened her throat and I watched as my cum slid down in one big gulp.

After clothing had been put back on, the desk cleaned up and we had a chance to catch our breath we sat down to talk before she left.

“Tony that was the most incredibly erotic thing I have ever experience. I hope that you feel the same,” she said.

“Absolutely! I want more of what we just did Jessica. The whole idea of us being able to have sex like that with no strings is quickly becoming something I am addicted to.” 

We talked a bit more and then realized with the hour being so late she needed to go but would stay in touch via e-mail and see when we could get together again.


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