Working Under Cindy

She tells you to calm down and to crawl under her desk. As you get into position you can feel her legs start to envelope your head and you lean forward anticipating her wonderful pussy, however, this time when you lean forward you encounter something hard. You stick your tongue out and as you open your mouth to ask what it is as she slides forward inserting the strap-on dildo she is wearing into your mouth.

You are so overwhelmed that it doesn't it dawn on you that she is fucking your mouth with a strap on dildo. As she tells you to focus more and to not grate your teeth over the surface you come back to your senses. With your hands cuffed behind you and you wearing nothing but your birthday suit you are not in any position to argue.

So, you concentrate on giving head to the dildo as you would like it done to you. She continues to fuck your face but has to thrust less now that you are into it and in fact you realize that you are actually deep throating this fake phallus. After 30 minutes of working on this she suddenly begins to shake and as her orgasm overtakes her she thrusts forward burying the dildo all the way into your mouth, completely filling it.

As you breathe through your nose you feel a liquid splash across the back of your throat and for the second time this morning you are caught by surprise. She settles down from her orgasm and begins to withdraw from you, you taste the liquid and realize that it is somewhat salty. She completely withdraws from you and looks down at you past the fake phallus with such a wicked smile you actually blush.

Cindy asks how you liked sucking cock, but before you can answer her, she nudges your rock hard cock with her nylon covered foot and states that you obviously enjoyed it. She then orders you into the Inspection position and you quickly scramble out from under her desk and assume the position as best you can since you are still wearing the handcuffs. While she is still sitting in her chair she rolls over to you and begins to give you some of the best head you have ever had.

Just as you start to get close to erupting inside her mouth she grabs your balls and squeezes just enough to quell that thought. As she continues to felicitate you she slowly reaches around your back side and begins to rub lube into your bung hole. Finally, you can't stand it anymore and beg her to let you cum, she does and you let loose with a torrent of cum filling her mouth.

While you finish and begin to soften she stands up and grabs your head with both hands and plants her lips on yours and transfers your cum from her mouth to yours. You eat it down and continue to passionately kiss her. After she breaks the kiss she unlocks the cuffs and hands you her delicates from yesterday and tells you to get dress. As you walk out of her office that morning you are on cloud nine and don't have a care in the world.

With this new toy introduced into the mix, things continue for several months, with you becoming very adept at sucking her 'cock'. You also learn to take her strap-on up your backside and just like when you sucked her off she makes sure to leave a load inside you, which allows you to experience firsthand what a woman might go through after a quick romp. In fact on several occasions you didn't catch the leaking fast enough and had a bit of a spot on your pants. You decide to mention it to her the next morning.

You stand there in front of her desk in the Inspection position, and you tell her of your predicament. She gets somewhat upset with you and tells you that as a sissy you should know how to handle it, but that since you don't she will help you out. She then has you put on the previous days garter and nylons, which you think is odd, but decide not to challenge it since she is already upset.

She then produces a pair of 4" open toed heels and has you put them on and walk around the room. Since this is your first time at wearing heels, you don't walk very gracefully. She continues to have you walk around giving you instruction on how to swing your hips more and take smaller steps. Finally after 30 minutes of practice your feet are starting to hurt, but you opt to just endure. She then has you come over to her desk and cuffs your hands behind you. She then bends you over her desk and tells you how wonderful your 'vagina' looks framed in garters.

She then begins to lube up your backside and then proceeds to mount you while wearing her strap-on. As she enters you, you notice that the strap-on feels somewhat bigger but figure it must be the position you are in. In reality she has moved onto a bigger dildo. As she pushes more and more inside you, you relax your muscles and anxiously wait for her to reach the end.

This new dildo seems to go on forever, but finally her thighs are resting against your nylon encased legs. As she lets your body become adjusted to the new size and length she tells you that she wants to meet with you this weekend and have you prove how far you are willing to submit to her. Before you can answer she begins to withdraw and you readily agree and try to thrust your ass back toward her. She pulls out until only the tip is inside you and then begins to slowly fill you up again.

This new dildo feels so wonderful and seems to trigger feelings that you didn't know existed that you clamp your mouth down on your arm so as not to cry out. She continues to thrust in and out of you slowly at first and then picking up speed until she is slamming into you.

Finally, as her orgasm rips through her body she slams the entire length into you and fills your backside with fluid. You flex your muscles trying to milk every last drop out of her. As she finally withdraws, you feel a very empty sensation, but just as quickly you feel something being inserted into your 'vagina'.

Cindy tells you to stand and you realize that she has inserted a tampon. She uncuffs your hands and tells you to get dressed. As you are finishing buttoning up your shirt she hands you several more tampons and tells you to use them throughout the day so that you don't leak. The rest of the day as you move around on the floor you can feel the tampon inside you and your thoughts continue to drift back to Cindy and your session with her this morning.

The rest of the week goes as usual with you spending the first hour of every day in her office satisfying her sexual cravings. Friday afternoon rolls around and as you prepare to go home for the weekend you receive an email from Cindy giving you an address to a hotel and a time to be there. She also tells you to wear the same things you have on today and to make sure you are ready to prove your devotion.

You drive home and your mind wonders what she has in store for you and you almost miss your turn for your apartment. That night you can hardly sleep due to the anticipation of Saturday. In the morning after having some breakfast you take a shower and use the depilatory solution to ensure you are nice and smooth. As you towel off you begin to put back on the garter belt and nylons and put on some sweats over them along with a pair of slip on shoes. In her email she instructed to you to be at the hotel room no later than 10 am and so you have to hurry in order to not be late.

You reach the door, knock and stand there nervously awaiting today's events. Cindy answers the door wearing a black leather bodice that squeezes her waist and pushes up her ample tits so that they are only half way supported. She is also wearing black fishnet stockings and knee high boots with 4" heels.

She commands you to come in and remove your clothes while she locks the door behind you. You quickly remove your sweats and are standing in the middle of the room in nothing but your garter and nylons. She tells you to remove your pretty lingerie also and then proceeds to give you a pedicure and manicure ending with all of your digits covered in bright red nail polish.

She then hands you a matching black lacy bra and garter set along with black nylons and the heels from earlier in the week and has you put them on. As you finish with the clothes and stand up she looks at you and tells you that it just won't do.

You look hurt, but become bewildered when she pulls down your bra and begins to glue silicon breasts to your hairless chest. As she helps you put your bra back in place she gives you a very satisfactory look. She then has you walk around the room getting used to the feeling of having 46 D tits. At first you like the feel of the weight, but after only 30 minutes you start to understand what having tits entails.

She then has you sit down so she can put make up on you. She starts out tweezing your eyebrows and then applies a foundation and blush. She then makes your eyes to be very sensual and lusty with smoky colors. For your lips she outlines them with a lip pencil and then fills them in with a very bright red lipstick that matches your polish. Next she retrieves a blonde shoulder length wig which she secures to your head with glue explaining that she doesn't want it to come off during the night's activities.

At the mention of this your member begins to twitch and you figure you are going to have a great time serving her and doing her bidding, little do you know. Next she pierces both your ears and puts long, dangly diamond earrings in them.

She then has you stand and applies some of her perfume to your wrists, throat and behind the knees. She then proceeds to put a black lacy choker around your neck and a gold dangle ankle bracelet around your left ankle. As you sit there imagining what you look like your penis begins to grow and stick out from between your garter straps.

She notices it and tells you that you are not being very lady like and drops between your nylon covered legs and begins to go down on you. Your mind is in such a state of sexual arousal that you don't last very long and blow your load into her mouth as she continues to suck every last drop out of you.

She then stands and leans down to give you a kiss. As you open your mouth she pushes your load of cum into your mouth with her tongue. You are so entranced by the feel of your lipstick lips sliding against hers that you just swallow without even thinking about it. Once she is finished she stands, fixes yours and hers lipstick and then heads over to the closet.

She returns carrying a very short, very sexy looking red brocaded dress that has a slit up one side and not very many buttons down the front. As she helps you put it on, you realize that if you were to lean to far forward you would fall out of it.

You also notice that the dress just barely comes to your stocking tops and the slit is strategically placed so that when you walk in your mincing stride it reveals your garter straps. She has you stand up and walk to the bathroom to inspect the end result.

As you enter the bathroom you see several mirrors lining the wall and almost stop thinking that there is another woman in there when you realize that it is just you. As you stare at the beautiful blonde in the tight red dress wearing black nylons and heels you can't believe your eyes.

This sight causes your cock to stir again. Cindy, now fully dressed, walks in behind you and tells you that since you can't seem to keep your 'clit' under control she will have to do it for you and tells you to pull up your dress.

You do so and notice that she has some sort of latex panty in her hand. She first unfastens your garter straps and then proceeds to pull it up your legs. As she reaches your member she takes it and tucks it into a tube and then proceeds to finish pulling the panty up. She informs you that these "pussy panties" will help hide your real 'clit' and as you look down you see a latex vagina with a blonde triangle of hair above the slit. You are in such shock that you don't notice the fact that your back side seems to be exposed. While she reattaches your garter straps, Cindy informs you that from now on you will have to sit down to pee just like a real woman.

By this time it is almost 1 pm and she asks you if you are hungry, you say you are and so she hands you a purse and tells you to come with her. At first you hesitate, but then look back in the mirror and wonder if anyone will be able to tell you are not a woman. The two of you head out and find a nice place to have a simple lunch.

Afterwards she takes you to a nearby mall and proceeds to drag you around to various stores having you buy more lingerie, dresses and heels. She tells you that she wants you to start wearing woman's clothes whenever possible, which means whenever you are not at work. After several hours of shopping your feet are beginning to ache and your back too.

She smiles knowingly and tells you that she has made reservations at a very nice restaurant for dinner. As you pull up the valet can't keep his eyes off of your legs and you notice a slight bulge in his pants. At first you are somewhat shocked but realize dressed the way you are, why shouldn't you cause that kind of reaction.

You enter the restaurant and you realize that this is a very expensive restaurant. As the maître d' seats you and Cindy in a circular back booth you notice that the atmosphere is very romantic. You immediately slide in next to her and feel your stocking legs rub against each other making a zipping sound which causes your member to stir, but with the "pussy panties" you can't get hard.

Cindy notices your discomfort and just smiles. Before either of you can say anything, the waiter appears and asks for your drink orders. Cindy orders a bottle of White Zinfandel and tells the waiter that you are waiting for others. This comment catches you a bit off guard, but figure Cindy knows what she is doing.

The waiter leaves and Cindy turns to you and tells you that after all that walking her feet are a bit tired and asks you to slip under the table to massage her footsies. You seem a bit taken aback, but as she lifts the table cloth you gently slip beneath the table.

Once down there you realize that the table cloth is long enough so that no one will notice you under there. You quickly remove her boots and begin to massage her feet. As you work your way up her calves she spreads her legs and her aroma reaches your nose and you can tell that she is wet.

You continue to massage upward she continues to spread her legs more and more to allow you easier access. You notice that her fishnet stockings are crotchless and you can just barely see the moisture gathering on her outer lips.

You quickly move in and begin to lick and flick at her lips. It isn't long before she grabs your head and pulls you in very close so you can insert your tongue into her folds. You are so caught up in servicing Cindy that you don't notice two more sets of legs appear under the table. At first you are afraid you will be found out and embarrassed but Cindy continues to hold your head encouraging you to continue.

You continue to suck and lick until she finally reaches her orgasm and clamps your head with her thighs and her juices flood your mouth and face. You figure now she will let you arise, but instead she pushes you over to one of the two pairs of legs.

You now notice that both sets of legs are dressed in pants and realize that they belong to men. At first you don't know what to do, but then see that both men have unzipped their pants and are stroking their members.

At this sight one of the men grabs your head and directs you to his crotch. At first you are hesitant, but then you feel Cindy's foot rest itself between your legs and begin to apply pressure and so you lean in to the man's groin.

Causing the pressure on your nether region to lessen and before you know it you are face to face with a man's cock. You only have time to lick your lips before he guides your mouth towards his now raging hard on. With Cindy's foot still between your legs you hesitantly open your mouth and allow the cock to slid between your lips.

The initial taste is salty and you figure it is precum, and while you are thinking about this he keeps feeding more and more of his cock into your mouth. Your gag reflex kicks in, but you relax and before you know it your nose is buried in his pubic hair and your mouth is completely filled with his cock.

While still guiding you he begins to withdraw your head until you are at the tip and then begins to feed it to you again. You figure you have come this far and so you begin to slid back and forth on his cock until he finally tenses up and grabs your head pulling it all the way down on his cock and begins to shot wave after wave of cum down your throat.

You swallow as fast as you can but he cums so much that some of it trickles out of your mouth. As his cock begins to soften he lets go of your head, passing you along to the man next to him.

This time you don't need any encouragement and begin to bob back and forth on his cock until again you are rewarded with a very large quantity of cum. As you are hunched under the table the waiter returns with the wine and takes everyone's order. Once he leaves, you discreetly exit from underneath the table where Cindy is holding up the table cloth. As you emerge you notice two very handsome men sitting at the table with very big grins on their faces.

Cindy looks at you and wipes some cum from your chin and feeds it to you and tells you to come with her to freshen up. Once in the ladies room, Cindy tells you that the first gentlemen you took care of was her husband, Jim and that the second was his friend from work, Bill. She helps you freshen up your lipstick and then tells you that you will be Bill's date tonight. As you return to the table your salads have already arrived and both men get up to allow you and Cindy to sit on the inside.

Dinner is pretty uneventful, if you consider that Bill can't seem to keep his hands off of you and continually gropes you. All this sexual activity is causing a great stirring in your loins, but due to your restraint you don't get hard. You do notice that your "pussy" does seem to be getting wet and wonder about that, but Bill then pinches one of your nipples and the sudden pain brings you back to reality very fast.

Everyone finishes dinner and Jim suggests you go out dancing at a local club. Cindy thinks that is a wonderful idea and you all head out. As you reach the front of the restaurant, Cindy tells you to ride with Bill. The valet brings Cindy's car and as you watch her and Jim drive off, Bill lets his hand slide to your ass and he gives it a squeeze before leaving it there. The valet returns with his car and as you enter his very low car you expose quite a bit giving the valet one of the best sights he has seen all night.

During the short drive to the club Bill continues to fondle you, which only causes you to get damper and damper between your legs. You arrive at the club and after parking Bill pulls you close and gives you a long, deep kiss smearing your lipstick. He grabs your breast and tells you he can't wait to see you shake your thang. You enter the club and see that Jim and Cindy already have a table and that there are already drinks on it.

You sit down sandwiched between Cindy and Bill and take a big swallow of the drink offered you. Your mind is in such a state of sexual frenzy that the alcohol seems to go straight to your head and you immediately begin to feel more easy going. It isn't long before Bill is pulling you out onto the dance floor where you dance several fast dances, as best you can in heels.

The next song is a slow song and Bill grabs you and pulls you close to him. Your face rests on his chest and you feel his hands roaming all over your backside and eventually resting on your ass.

The song ends and you head back to the table noticing Jim and Cindy getting up to leave, you start to ask a question but Cindy merely silences you with a look and you and Bill follow after them.