I Keep Tracy After School

"Hello Mr. Crabby. This is Tracy. I have been a naughty girl and I have to stay after school." That was the message, in a falsetto voice, that I heard when I answered my telephone a few days ago.

Tracy is a thirty year old woman who likes to role-play a naughty 18-year-old schoolgirl who is forced to serve detention. I was to be the mean principal who takes advantage of her so I told her "Tracy, you naughty girl! You get over here to my office right away!!" She would be over in less than an hour so I prepared the "detention room". This is a spare bedroom that I usually use as an office. I cleared all my books and my computer off the top of the desk and replaced them with my spare comforter, a folded blanket and some pillows. Some cheap plastic rulers were available in the drawer as were condoms and other things I expected to need. The rulers were for spanking Tracy and they were so thin and flexible it would be like spanking her with a ribbon. There are also a sofa and a wooden chair in the room so, after showering and shaving, I sat down and waited for Tracy.

When she arrived her hair was in a ponytail and she was wearing a long raincoat, which she removed and I hung in the closet. I was wearing my sternest expression, and this was really difficult because Tracy had on her version of the school uniform. This consisted of a white middy blouse and a plaid skirt. The blouse was so many sizes too small that it was completely unbuttoned and there was no bra or anything underneath. Tracy has a beautiful, voluptuous body with large, firm breasts, and I had to fight off the urge to fondle and kiss them. I stayed in my role and ordered her to my office, because I knew the fondling and kissing would come later.

The plaid skirt was only about eight inches long and there was nothing underneath it either, except her curvaceous ass and other private parts. I was eagerly anticipating the fun we would have in the "detention room".

When I walked in, Tracy was really into her role, looking scared while sitting in the wooden chair. She had removed her saddle shoes and her bobby sox but otherwise was in character. I had removed my shoes and socks also but otherwise I stayed in my role too, and bawled her out and told her I might expel her for being naughty. "Oh, please don't, Mr. Crabby", she begged. "I'll be good. I'll do anything you say. Please don't expel me."

I told her I was going to spank her and ordered her to bend over the desk.

"Please don't hurt me. I'll be good." But her pleadings fell on deaf ears.

Tracy bent forward over the desk and held a pillow under her chin. More for my visual delight than for anything else, I lifted her tiny skirt out of the way. Her ass is a thing of beauty with its voluptuous curves and its ivory skin, so alluring that I had to force myself to hit it with the ruler. "Ouch", screamed Tracy. "Ow, ow, ow, stop, stop, you're hurting me", came her pitiful cries.

The ruler broke and there wasn't a mark on her flawless skin. "Now look what you've done", I thundered. "You are even naughtier than I thought.

You come over here, I have to punish you more." I led her over to the sofa, pulled down my pants and underwear and sat down. After gazing at Tracy's gorgeous body and anticipating what we were going to be doing, my cock was fully erect. I ordered her to her knees and told her to put it in her mouth.

"I can't put your thingy in my mouth", she wailed. "It's too big."

"You do what I say or I will expel you and then what will you do?"

Seemingly reluctantly, Tracy put her lips around my cock. I touched her hair and her head bobbed down and enveloped my entire cock. "Now, suck it", I ordered her. She raised her head slowly, her tongue massaging my cock inside her mouth. Down and back up again went her head, again and again, while my cock was embraced and caressed by her very talented tongue. Tracy was demonstrating the same skill at sucking cocks and the same pleasure it gave her that she had shown me on other occasions. I interrupted her to remove the middy blouse that was blocking my view of her gorgeous titties as they swung beneath her. They were so enticing that I had to reach out and fondle them, especially the fully erect nipples.

Tracy took my cock out of her mouth. "My mommy says I shouldn't let men touch me there."

"If you tell your mommy, I'll tell her how naughty you are and expel you.

Now, take off my pants and lick me here", I commanded, pointing to my crotch and balls. Then I scooted forward on the sofa to give her full access to the places I wanted her to lick. After pulling my pants and underwear all the way off, Tracy licked my crotch and the base of my balls, then took one of my balls into her mouth and licked it and rolled it around. She did the same to my other testicle and then stopped. "Now lick my thingy", I ordered. Tracy lapped at my shaft and the head of my cock, then flicked the hole at the end of my cock with her tongue. "Now put my thingy back in your mouth and suck it."

"I can't, Mr. Crabby. I have a toothache."

"I don't believe you, Tracy. Now stop being a naughty girl and suck on my thingy or I will expel you." Back around my cock went her lips. All the way into her mouth went my cock, over and over again, with her tongue caressing my shaft and her lips applying extra suction as she withdrew her mouth. Tracy came slightly out of character and stopped her oral action, took my cock out of my mouth and smiled at me. She had the seductive, teasing glint in her eyes that I had seen before when she was sucking me off, or was otherwise highly aroused. I came out of character too, and smiled back at her. We were both enjoying ourselves immensely but we had to play the game to get the most fun out of it. "You put my thingy back in your mouth right now, young lady!", I bellowed at her. Tracy grinned and her mouth once more engulfed my cock and she continued her long, slow sucking strokes.

Although the strokes were slow, I could feel my climax building and I knew I couldn't stop it now. "Since you are being a good girl now, Tracy, I'm going to give you a special treat", I told her. She knew that special treat was a big spurt of cum, which really is a special treat to her, so she increased the speed of her strokes. Her tongue was still laving my cock but when she withdrew her mouth she pulled back slightly, then sucked hard and my cock went most of the way back in, then withdrew a bit more, then sucked most of it back in again, and continued like this until only the tip was still covered by her lips. Then she sucked my cock all the way into her mouth and withdrew in the same way, except her action was smoother and faster than my description. This is the technique she uses when she knows I am about to cum, and it always gets me off.

It did this time, too. After just a few of these strokes, I delivered Tracy's "special treat". She felt my cum flooding into her mouth and closed her lips tightly around my cock. When the spurting stopped, she swallowed that and squeezed what was still left in my cock into her mouth. There were still some drops of my cum left on the head of my cock after she took it out of her mouth and I ordered her to eat the rest of her "treat". She gladly licked it all off and also licked around the head and got it all. "I'm not done punishing you, Tracy", I told her. "Now sit down on the sofa by me until I'm ready to do the rest of what I am going to do about you. She had been lubricating so heavily that there was a wet spot on the floor where she had been kneeling. I pointed this out and told her I was going to punish her for getting the carpet wet but that she should stay where she was until I was ready.

When I was ready, I told her to kneel on the sofa facing me. What I wanted to do was to kiss her beautiful face but I had to stay in character, so I cupped my hands under her gorgeous titties and began to lick the erect nipples. They were big and sensitive and after a few minutes of my tongue switching back and forth from one nipple to the other, Tracy was breathing hard. I clamped my lips on one of the succulent globes and sucked on it, while my tongue continued to lick the nipple and the areola. The other globe got the same treatment and I switched back and forth from one of her luscious mammaries to the other, until I could smell fresh juices running in her pussy. "You are being a good girl now, for a change", I told Tracy.

Now go and lie on top of my desk." She knew what was going to be happening next, of course, so she arranged the pillows so she was comfortable and lay down with her gorgeous ass next to the end of the desk that was in the middle of the room.

I removed my shirt and knelt down in front of her and stared at the beautiful pussy just inches in front of my face, and right at eating level.

She was still wearing her eight inch long skirt, and I folded it back to keep it out of my face. Tracy shaves her pussy, and she had apparently shaved it just before calling me that morning. That was good, first because the smooth, hairless skin would feel so good to my tongue and lips, second because it would be more sensitive for Tracy, and she would enjoy it more, and third because the lack of pubic hair was in keeping with her role of a young girl. "Please don't hurt me, Mr. Crabby. I'll be a good girl." I smiled at this because, right now, Tracy was being not just good but wonderful. There was so much juice in her pussy that, instead of licking it out, I pressed my lips against the edge of her love hole and sucked it out.

It was delicious, as I knew it would be. There was still some left and I licked that out and started licking around the edges of Tracy's delectable love hole.

Just below the place where I was licking was her pretty, pink ass and I decided to soak my finger in my mouth and stick it in there. When I started to do so, I heard Tracy's voice. "Mr. Crabby, that's my poo hole. What are you doing there?"

"Stop being naughty, Tracy, and put your hands down here. Good. now spread yourself", I told her, as she reached down and spread her asscheeks. I slipped my lubricated finger in, pumped it a few times and resumed licking her lovely pussy. I started licking one of Tracy's inner pussy lips, at the top where it forms part of the hood over her clit. I would be licking her clit itself soon, but I was in no hurry. My tongue probed and licked the outside surface of this first lip, spending a lot of time in one place and licking everything it could reach. Slowly and steadily my mouth moved down the pussy lip, licking everything over and over again until I was at Tracy's adorable love hole. I could hear her purring contentedly, which was somewhat out of character but we had decided it was not anything we would try to prevent.

I started licking my way up the same pathway but this time I was concentrating the strokes of my tongue on the inner surface of the outer pussy lip and probing my tongue into the seam between the two labia. All the way to her mons, I licked, then I kissed her there. All of her hairless pussy felt good to my tongue and lips and it was all sensitive. I looked at Tracy's face and she had the same teasing, seductive glint in her eyes that I had seen before when she was sucking my cock. Tracy was cooing louder, expressing her pleasure as I started licking the outside surface of the other inner pussy lip. Again, I avoided her clit because I wanted to bring her slowly to her orgasm and I wanted us both to enjoy it for a long time.

Even so, as I licked my way down this other lip, her pussy had started humping into my face. Slowly, covering every bit of this delectably soft and smooth lip, I licked my way down to Tracy's precious love hole. Another rich harvest of her delicious pussy juices waited for me there, and I devoured it all, and started licking the inside of the outer lip on the same side. Again, my tongue probed the seam between the inner and outer lips.

Slowly, past her clit, all the way to the end of the outer lip my tongue worked its way and I kissed her sweet mons again.

I turned my attention briefly to the middle finger that I was fucking into Tracy's lovely ass. After pulling it almost all the way out, I pried open her sphincter with the fingers of my left hand, and slipped my right index finger in beside my middle finger, then pushed both the fingers all the way into that sweet ass. I fucked her ass several strokes with the two fingers and Tracy's cooing turned to pleasurable moans, her pussy started humping even stronger and her thighs rotated out to present her pussy more fully to my mouth. Another gush of juices filled her love hole and I eagerly devoured every drop.

With my chin resting on my hand, I probed the lower edge of Tracy's love hole. Her pussy was squirming now, besides humping into my face and her moans were interspersed with sighs and gasps. Tracy's hips were swiveling on top of the desk, thrusting her legs over my shoulders like pistons. My tongue probed firmly along the sides of Tracy's adorable love hole and her humping became even stronger. When I started thrusting my tongue against the upper edge, applying pressure to the clit, Tracy became even wilder, begging me to suck her clit. I covered that precious love button with my mouth and held it firmly with my lips while applying suction. While I sucked on it, my tongue licked and caressed and probed the top and sides of the little darling.

"I'm cumming! I'm cumming!", Tracy howled joyously and her legs clamped down on the sides of my head. Her arms were sprawled out at her sides and her hips rolled back and forth on top of the desk. I held on tightly and braced my self to keep her from falling off the desk. Tracy climaxed with a spasm of her body that lifted her ass off the desk and then she sagged back and loosened the grip her legs had on my head. Fresh cum juices are the best kind of pussy juices and I feasted on what was in Tracy's love hole before going to the bathroom to wash my face and, especially my hands after handling her ass and finger-fucking her. I also brought a basin of hot water, some soap and a towel with me and set it on the wooden chair because I expected to need to wash my hands again, after seeing how much Tracy enjoyed anal play that day.

When I returned, Tracy was lying on the desk with a blissful smile on her face but she quickly got back in character when she saw me return. "Are you done punishing me Mr. Crabby? I want to go home now. Can I go home now?"

"You probably can, Tracy but no, you may not. You are such a naughty girl that I have to punish you more. Now stand on the floor here and lean across my desk."

"Please don't spank me any more, Mr. Crabby. I'll be a good girl. My rear end is still sore from before."

"I spanked you once and you just kept on being naughty. I'm going to have to do something else. Now stand on this platform and bend over and lean on the desk and spread your legs." Tracy is only five feet, four inches tall and by standing on the platform, which was six inches high and I had made specifically for this purpose, her pussy would be at the perfect height.

Tracy did as she was told, except she leaned on pillows and put the folded blanket against the edge of the desk. We both knew that we would be fucking and that some of my thrusts would be strong, and we didn't want to bruise her legs. I got a condom out of the drawer and put it on and stepped between her legs and moved that silly skirt out of the way again. Tracy had apparently been anticipating the "punishment" she was going to get because her pussy was dripping wet and some of the juices were running down her leg. I wiped it off with my finger and licked it off. It was delicious. Then I reached in and opened up her pussy lips with the fingers of my left hand and guided my cock in with my right hand. One quick thrust and a few inches of my cock entered Tracy's dripping pussy. "Should you be doing that, Mr. Crabby?" Tracy asked, innocently. "My mommy says I shouldn't let men touch me there either."

I laughed, silently and said nothing aloud. Another thrust of my cock and I was all the way in her lovely pussy. With my hands on her voluptuous hips, I pulled my cock almost all the way out of that delightful place then slowly stroked it back in again, all the way so my pubic hair was tickling her hairless pussy. Tracy was cooing already and it was obvious that she was really enjoying what her mommy didn't want men to do to her. I continued stroking my cock in and out of her lovely pussy, and she started thrusting her pussy back to meet my cock. Tracy was lubricating so heavily that my cock made a squishy sound as I entered her and her juices were running along my cock and down my legs, as well as running down her legs.

I wanted my cock to massage all of Tracy's pussy so I swung her hips first to the left when I thrust my cock in and out, and then to the right. These motions changed the angle of entry so my cock thrust more firmly first against the left side of her delightful love hole, then the right. Tracy's cooing had already changed to moans of pleasure, and they became louder with this change in sensation.

I continued swinging Tracy's hips from side to side, and she continued thrusting back to meet my forward strokes, then she started a new motion.

She began swiveling her hips like she had done while I was eating her pussy except that her legs were pistoning into the floor as she shifted her weight from one foot to the other. The new motion of her pussy combined with the thrusts of my cock brought new pleasure to both of us. I changed back to plunging my cock straight into her pussy, and she continued to thrust her pussy back to meet me while swiveling her hips. "Do you still want to go, Tracy?", I asked her.

"No, Mr. Crabby. I want to cum!"

By standing on my tiptoes I changed the angle of my stroke again so the main force was on the top of Tracy's love hole, and the head of my cock rubbed against the underside of her clit. I also picked up the pace because I knew Tracy was ready to cum, and I wanted to make it as strong as I could. I was not ready to cum yet because my cock still had a date with her lovely ass.

While still thrusting my cock strongly into her pussy, I reached my hand around her and down her belly until I felt her adorable clit. I gently massaged that sweet love button and I could feel my cock rubbing against the underside while my fingers played with the organ itself. After a few minutes of this double caressing of her clit, Tracy howled "I'm cumming!

I'm cumming!"

Being pinned against the corner of the desk as she was, Tracy couldn't move much while cumming, but her arms were flailing the top of the desk and her feet were dancing on her platform. I continued stroking into her pussy and massaging her clit with my cock, as well as massaging it with my fingers until she climaxed with a sudden jerk of her hips. Then she sagged against the desk and her upper body sprawled on the top, with her arms stretched out at her sides. I came down off my tiptoes but kept my cock imbedded all the way in her pussy while Tracy recovered her strength, after her climax.

"Are you through punishing me yet, Mr. Crabby? MAY I go home now?" That was what Tracy asked when she pushed her upper body off the desk and supported herself there with her hands. She was grammatical this time, emphasizing the word "may".

"No, you may not, Tracy. You are such a naughty girl that I am not through punishing you yet. Now you stay where you are." Having said that I eased my cock out of her pussy, trying to catch as much of her cum juices as I could. I licked them off my hand and then got on my knees and licked everything I could out of her pussy and off her thighs. As I spread her asscheeks and licked, I could see Tracy's cute rosebud and it seemed to be winking at me in anticipation of having its turn next. I ordered Tracy to stay where she was and got out the KY Jelly and covered my cock with it.