Adventures Part 2
By Captain J
[email protected]

copyright 2007 by Captain J, all rights reserved

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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The Garden Party

David was very nervous as he approached Mrs. Wilson's house. The old woman had caught him serving as a nude waiter for the girls and all but demanded that he provide the same service for her old biddy garden club friends. The only good part was that he was to be paid five times his normal pay rate for the afternoon. Mrs. Wilson had called earlier and told him to arrive at 12:00 even though the group was not scheduled to start their meeting until 1:00.

Pushing the doorbell, his whole body trembled as he wondered what awaited him. He didn't have long to wait, when he was met by a smiling woman, "Come in David, we need to get you ready for the party."

"Hello Mrs. Wilson, ... what do you mean ready?"

"Well we want to keep who you are a secret, don't we? So I had to come up with a costume for you."

"Secret?"

"Certainly! We can't have everyone knowing you do these little naughty jobs, now can we. What if the whole town were to find out? No we have to keep our naked waiter's identity secret or bad thing could happen..."

"Ok... Uh... What should I do?"

Without further discussion, David was led into the bathroom and told to strip. Then to his dismay, Mrs. Wilson had him stand in the bathtub and took her time spreading a smelly lotion all over his body below the neck. Then told him to stand there not touching anything for the next 15 minutes. David's skin was warm where the lotion was on him and getting increasingly uncomfortable; just when he was about to call out to complain, the woman returned and using a handheld shower and washcloth, began spraying and washing him. David watched the water as it ran down his body and noticed it looked dirty; but the total shock arrived when he looked at the placed she'd rubbed with the washcloth to discover that all the hair was gone. By the time she was done, he didn't have a single hair left below his neck.

"Mrs. Wilson?" he almost whined.

"Yes David, now you're all soft and smooth just like a girl or baby... don't worry it will all grow back... eventually... <ha..Ha...Ha...>"

The woman threw him a towel and told him to 'pat not rub' himself dry and he quickly complied, then she handed him a big container of baby powder and told him to rub it all over himself; again he complied; it fact it felt really good powdering himself, his skin was so smooth, it was amaizing...

When he was finished, she took him by the hand and led him into the hallway and to another room. "Your costume is on the bed, David," she instructed, "If you need help just give me a call; I'll be back in a few minutes." Then turned and walked away.

David looked at the bed and couldn't believe what he was seeing... There on the bed were sheer white stocking, a white garter belt, black high heel shoes with what looked like about 3" heels, open toes with a thin strap for the ankle, a white lace maid's hat, and a Halloween mask which looked like a woman's face; the kind that's almost transparent with an elastic strap that went around you head and a blond wig. 'I can't wear this stuff!' he thought to himself.

"WHY aren't you getting dressed?" he heard from behind him.

"Mrs. Wilson... I....I can... can't we...wear that..." he stuttered in reply.

"You certainly CAN and you WILL!" she demanded, and emphasized her point by swatting his rear with a metal handled wire fly swatter. "You sister said you might need persuading so I'm prepared, now start moving or you'll be serving the ladies with a very RED behind!"

David picked up one of the stockings but had no idea how to proceed and started putting his foot inside when she stopped him. She then had him put on the garter belt and sit on the bed, then showed him how to ball up the stockings and gently pull them up his legs, and assisted as he had no idea how to attach the garters. Once the stocking were on and attached, she put the shoes on him and he got another surprise when after buckling the ankle strap, she placed a small gold padlock through the strap on each shoe so that they could not be removed.

"Now stand up and walk around some, you'll need to get used to those shoes, they change your balance..."

David stood on shaky legs and almost fell when he tried to walk a step and his foot turned under. It took about ten minutes before he got the feel of walking with the heels on, and his legs and lower back were already complaining. It was going to be a long afternoon.

"We have to hurry here, the other ladies will be arriving shortly; come over here and I'll finish you up," she directed and quickly placed the mask on him, then fitted the wig over his head, making sure to cover his hair. "Now let's see that nice erection," she purred in his ear and David reached down and started stroking himself.

"I'm waiting!" she said several minutes later when no erection had developed, "It seems you need some help; bend over!"

David didn't know what was happening but bent forward as she stepped behind him and she took hold of his cock between his legs and 'milked' it downward as a finger probed his rear entrance. Within seconds her finger was on his prostate and he was hard as a rock in her hand. <She may be old but she knows the male body> crossed as a flash through his mind. "Now stand up and turn around," she ordered and then quickly placed a leather strap under his balls and over his cock, making both stand out from his body and obviously trapping the blood there to keep him hard. "Excellent!" she proclaimed, "Now we can't call you David or all my trouble with your costume is useless, so for the afternoon you will be "MISSY" understood?"

"Yes Mrs. Wilson..."

"Good, now Missy you will answer the door when my guests arrive and lead them to the patio. Once they are all here, you will serve drinks and snacks just like you did for the girls the other day, understood?"

"Yes Mrs. Wilson."

"You will not speak to anyone; so no one can recognize your voice; you will be handled by the ladies and if you are good, you will be permitted to cum; if not you will be spanked or punished as we see fit; understood?"

Just then the doorbell rang and the woman just said, "Answer it Missy!" and headed for the patio out back of the house.

David's whole body trembled as he wobbled his way on the high heels to the door and opened it, cautiously. There stood an old woman, had to be in her 50's, who just looked at him then broke out laughing, then finally choked out "Oh my, aren't we just precious!"

David motioned for her to enter and then led her through the house listening to her snicker behind him, "You need more practice in those heels honey, but they do wonders for that cute little behind..."

"Ah Mrs. Wheeler!" Mrs. Wilson greeted her friend, "Thank you Missy, you may go await our next guest," she said dismissing David, while guiding the guest to a seat.

David answered the door three more times almost without incident all were women in their 50's and 60's, one he'd seen around the neighborhood another at the drug store in town, but the last gave him a shock. It was Mrs. McMasters, the principle of his school! All made comments about his body and all got blushes in response, but his face just burned under the mask. Only the trembles and flushing of his skin around the edges of the mask and his chest told them how embarrassed he was.

When David went to retrieve the last guest he noticed Mrs. McMasters talking on the telephone but didn't pay much attention. At the door however, he got another shock, along with the woman were two boys he recognized immediately. Billy and Eddie Smith, both dressed in the same Brownie Scout uniforms as the day before!

"Grandmother, do we have to be seen like this?" Billy was saying through tears as David opened the door.

The woman looked at the naked erect boy standing in the doorway, then back at her grandsons. "Better like you are than he is! Now shut up and behave yourselves or you WILL be dressed like this sissy maid, only with VERY red bottoms!"

Both boys looked at the naked boy before them and gulped. Eddie's eye's locked on the erect cock and he whispered in his brother's ear, but then looked up at his grandmother and said, "We'll be good Grandmother!"

When everyone was seated, David stood waiting. "You may serve drinks now Missy," Mrs. Wilson directed. David went to the kitchen where trays of drinks and snacks were waiting to be dispensed, picked up a tray with glasses and iced tea and proceeded to serve the women. All of them took the opportunity to feel his body as he served them, paying particular attention to his erect cock, forward thrust balls and baby smooth behind.

"So tell us Mary, where did you find this lovely Sissy Boy Maid? His body is just so soft and smooth, and such a nice erection, to tell us how much we women are appreciated. I might want to hire him myself?" asked one of the women. Before Mrs. Wilson could answer and just as he served the last woman, the door bell rang again.

"Answer that Missy." He was told, and he set the tray down to comply.

<What now?> he thought as he walked through the house.

The previous shocks at the door were nothing compared to this one, standing there were two girls; one was the only other teenager in the neighborhood Becky Petry, age 15 and a year ahead of him in school; cheerleader, prom queen's court, most popular girl in her class accompanied by a younger girl who could only be her little sister about age 9 or 10, but already a 'looker' with long blond hair and long legs in too short shorts.

"OH MY GOD!" Becky exclaimed as both she and her sister took in the sight of the naked boy dressed up in stocking and heels with a prominent erection pointed at them, as they both laughed.

David motioned for them to follow him and burned from the giggles behind him all the way through the house. When he got them to the patio, Mrs. McMasters spoke up. "Mary, I hope you don't mind, but when I saw your Sissy Boy Maid, I had to invite my granddaughters it should be educational for them. Besides Mrs. Smith has her grandsons here, even though they are dressed as cute little Brownie's.

"Billy? Eddie?" the young girl exclaimed, "I know them from school! They're in my same classes!"

"Connie! You can't tell anyone!" Billy blurted out.

"Sure I can!" She replied, "So why don't you just explain how you ended up here wearing dresses."

"Stand up boys and explain to the ladies how you got yourselves in this situation" their grandmother ordered.

Both boy rose and Billy took Eddie's hand in his and gave it a squeeze, in support as his brother started the explanation. "Yesterday we went on an outing with the Brownie Scouts, to collect samples for our nature projects. When we got there, we were the only scouts not in uniform, so they made up wear these and took our clothes. When we got home, Mom decided to keep up dressed like this for the weekend."

All of the women laughed at the explanation and their grandmother added to their story. "Lori, their Mother, had other things to do today and I'd agreed to keep an eye on them; she said they were so much better behaved in dresses that she decided to keep them that way for the weekend and maybe longer if they acted up again. So it seems the Brownie Scouts know how to control unruly little boys better than their Mother." She said laughing and all of the women and girls joined it at the expense of the blushing boys.

"Missy, Connie and Becky need drinks!" Mrs. Wilson ordered, then turned to the girls, "When Missy comes back you may touch her however you want, just don't hurt her without my permission, OK?"

"You know Mary, I think Billy and Eddie should be helping Missy with the service here, it may teach them a valuable lesson, come here boys!" their Grandmother ordered. When they stood before her, she reached under Billy's skirt and pulled his panties down, then quickly did the same to Eddie; "Take them off and hand them to me, you won't need them until we leave," she ordered.

Billy started to object, but was quickly pulled across his Grandmother's lap and his dress flipped up and twenty hard spanks delivered before he could get two words out other than to yell at the spanking. Eddie just stepped out of his panties and handed them to her as his brother danced about, rubbing his now red behind.

"The same rules apply to these two as to the Sissy Maid," she told the group, "play with them all you want! Even though they don't have much yet, they are still capable of cute little hard-on's."

Both boys were sent to the kitchen to help the Sissy Maid and once they got there, Eddie immediately put his arms around the bigger boy's waist and hugged him. "David, we were sent to help you," he whispered.

"How... how did you know it was me?" David stammered.

"You have a mole there just left of your cock," Eddied continued whispering, "I recognized it."

"Listen you two," David replied, "No one but Mrs. Wilson knows who I am, and the others, especially Becky and Mrs. McMaster's CAN'T find out or I'm in deep shit! So no matter what, DON'T call me David, call me 'MISSY'!"

Soon the boys returned with trays of snacks and more drinks and all three were subjected to continuous feeling by hands all around the patio. When they were told to sit for a while, Connie placed herself between the twins and had a hand under each dress, playing with their boy parts; while her older sister explored David's erection and probed at his swollen balls. The head of his cock was purple and the skin was stretched tight all along his erection which was five shades darker than usual. It was so sensitive that even the lightest touch brought moans from him. "Mrs. Wilson, I think Missy needs to cum, her cock is straining pretty bad here," Becky announced.

"Well we can either let Missy do it herself or would you like to volunteer to do the honors Becky?" the woman responded.

"Could I? I mean I've only done it a couple of times..." she said blushing.

"No time better to learn dear, and I'm sure Missy won't complain if your technique isn't perfect. Just move him out here in the middle where we all can watch and then remove the strap and help him out."

"Would you like me to help you Missy?" the teenager asked.

David nodded his head violently up and down.

"Why don't you tell me?" she asked softly.

"Missy isn't allowed to talk," Mrs. Wilson replied, "it's one of his rules for the day."

"Oh...OK, Move out here and kneel facing the ladies Missy and I'll get this nasty strap off you and help you, OK?"

David nodded and quickly moved out to the center of the group, sitting back on his high heels, as Becky opened his legs wide and removed the leather strap, then knelt beside him and reached over and started slowly stroking him up and down. His whole body trembled and he dropped back his hands by his feet, his body arching up as he pumped his hips to speed up the stroking. Near the end, Becky just held her hand still, gripping him as he wildly pumped himself in her hand, until he finally shot the biggest load of his life in spurt after spurt into the air to the cheers of the women. When spent, he collapsed back onto his feet and his wig fell off as the exhausted boy lay there. When he recovered enough he realized the wig was off and quickly grabbed it putting it over his hair before sitting back up on his knees.

"Wonderful Missy, now go get a towel and clean up that mess you made," Mrs. Wilson ordered the still dazed boy. Who slowly got up on wobbly legs and headed for the kitchen. "Oh those heels just make the cutest little dimples in his behind," she murmured as he walked away, getting a laughter from all the women.

"How about these two?" Connie asked, as her hands continued to play under two Brownie Uniforms.

"I don't know if they can shoot cum yet," their Grandmother commented, "But I know they've been playing with each other since forever. So how about we have them do each other; I know they know how, I've caught them at it."

"Please No!" Billy pleaded.

"Billy didn't you learn your lesson already? Now both of you stand up and strip naked, then I want you two standing right out there in the middle and masturbate each other until you cum. Understood?"

"Do we have to?" Eddie said with tears in his eyes.

"YES! Or you won't be able to stand panties on your red behinds when I get done with you!"

Two very quiet boys slowly removed their uniforms and proceeded to the center of the circle of chairs with the watching women and girls. Then each reached for the other's erection with their right hands and began jerking each other off. Both were already on the edge from Connie's continuous handling and when Billy came after about 20 strokes, Eddie was right behind him, each spraying a few drops onto the other's stomach as they held each other by the shoulder with their free hands to keep from falling on their wobbly legs. Again all the women clapped and cheered, and the two naked boys were directed to go help Missy serve another round of drinks and snacks to the group.

After refreshments, it was almost time to leave, as most of the women had to go home and fix dinner for their husbands and families. All three boys were lined up and the two younger ones each were kissed by the women, who took the opportunity for a last grope, but Missy with her mask, got 'hand shakes' on her once again hard cock instead of kisses, except for Becky who hugged him and whispered in his ear, "Nice equipment David, see you around..." and her Grandmother Mrs. McMasters, the principle of his school, who also hugged him and whispered "I'll see you in my office Monday David, we need to talk..."

David didn't respond to either, just stood there trembling as they went out the door. When the door closed, he just dropped to his knees and whimpered "Oh God!"

"What's the problem David?" Mrs. Wilson asked.

"My principle recognized me and wants to see me in her office on Monday.... And...Becky recognized me too..."

"Well Becky seemed to like you, so I wouldn't worry too much about her. As for Mrs. McMaster's I'm sure she recognizes the need for discretion in this matter..."

"You think it will be OK?" he whimpered.

"I'm sure it will all work out, now go change back into your shorts and put your costume in this bag. Your sister wants you to bring it home with you. Oh, here is the key for the locks, now hurry, you don't want to be late for dinner."

David quickly went to the bedroom and removed the locks, shoes, stockings, garter belt, wig, mask and cap and put them all in the bag, then donned his shorts and t-shirt and tennis shoes and was heading for the door, when he was stopped by a hand on his shoulder.

"Here's your money David, you did a good job. I've have to hire you again some time."

It was a very worried boy who walked home that afternoon, his mind raced at the possible bad things which could happen with his Principle and Becky knowing who he was and he didn't even want to think about meeting Mrs. McMasters tomorrow.

When he got home, his sister met him at the door and immediately reached for the money envelope and extracted her 50%, before even looking at her brother. "So what's the matter with you?" she asked seeing his worried look.

"I'm in very deep shit; both Becky Petry and Mrs. McMaster's the principle of my school recognized me and the principle wants to see me in her office tomorrow."

"Well that explains part of the phone call I got then," Jane answered, "Becky called a few minutes ago and wants you to be with her little sister tomorrow evening so she can go on a date. Seemed strange since she's the only other teenager in the neighborhood and is always bitching about you stealing her babysitting jobs."

"I don't like the way this is all going, I have a bad feeling about it," David said with a tremble.

"Not much you can do but go along with the flow at this point," Jane giggled, "Now get cleaned up for dinner and then you have homework to do this evening; don't want to be in trouble with your Principle now do you..."

After dinner, his parents went out to some church meeting and just he and his sister were at home. David was working on his homework when Jane came into the room and stood behind him, looking over his shoulder. Suddenly she smacked the back of his head, "Ouch!" he yelled, "Why did you do that?"

"Because you deserved it! Stand up and strip!" She demanded.

"What are you talking about?" he whined as he rose and began removing his shirt. Jane smiled as she noted that he was complying with her order even though he was complaining. She immediately replaced the smile with a scow and just stood watching with her arms crossed over her chest, while tapping her foot to show impatience.

"I've been thinking about all this shit with Becky and Mrs. McMaster; it's all your fault, if you hadn't let your wig fall off, they wouldn't know who you were and everything would have been fine. So you deserve a spanking for screwing things up!"

"I didn't mean for it to happen! It came off when she made me cum..."

David was now totally nude before his sister and stood with hands trying for modesty as his head was lowered. "You should have been more careful and realized what could happen. So now you pay for it! Now get over to the bed and lean over it!"

"Please Sis, it wasn't intentional, ... I did... didn't mean for it..."

Suddenly she attacked without warning, holding him by the left arm as she swatted his rear hard with her right hand as she shoved him towards the bed. David danced trying to avoid her punishing strikes to his behind, but moving in the right direction and without fighting, lay across the edge of the bed. Once he was in position with his hip bent over the mattress, Jane grabbed his belt and folding it over, went to work, standing beside him and whipping his rear until it was crisscrossed with red welts and a crying and blubbering, older boy lay before her. She hadn't counted the strikes but her arm was sure tired. Satisfied he'd been punished enough, she threw the belt on his back and walked out of the room.

David lay there a long time, before recovering enough to go to the bathroom and find some medicated cream, which he gently applied to his damaged backside; then crawled into bed nude and tried to sleep. He didn't sleep well at all, between the pain in his butt and nightmares about what was going to happen tomorrow at school.

Changes at School

David woke the next morning, sore all over and groggy from lack of sleep. He put more cream on his behind and was looking at his butt in the mirror, tracing the red welts, when his sister entered the bathroom and saw what he was doing.

"Still hurt?" she asked.

"Some, but I don't think I can stand underwear on it..." he whimpered.

"Well we have a fix for that. From now on you don't wear any. I've been thinking about that anyway. You're naked more than clothed it seems any more and this way it's one less item for you to remove... So just put your pants on and quit all that whimpering!"

David returned to his room and dressed for school, knit shirt, slacks, socks and loafers. Then gathered his books into his backpack and headed out the door.

At school he was surprised when immediately after attendance was taken in Home Room, he was told to report to the Principle's office. <This is not good; she's not wasting any time...> he thought to himself as he walked down the hall to the administrative offices.

David had never been in the Office before and found himself standing before a long counter, with six desks behind it. Five were filled by students (all girls) and an older lady who he assumed was the School Secretary. David stood at the counter and the woman looked up at him from her desk. "You must be David. Mrs. McMaster is waiting for you; go through that door, through the conference room and her office is on the other side." She directed.

David looked in the direction she was pointing and saw a wooden door with a window in it and walked towards it. He opened the door and found himself in a room with a single long table and ten chairs around it; on the other side was an open door and he could see a desk with bookcases behind it. Slowly he walked across the room and stopped at the door, and knocked gently.

"Come in David," he heard from somewhere inside and when he stepped in saw Mrs. McMaster entering the room from another doorway. David advanced then stood before her desk, his whole body trembling in fear, wondering what was going to happen. Mrs. McMaster sat behind her desk and said nothing as she looked at the frightened boy before her for awhile. "Well David, I think an explanation is in order. Just how did you manage to get into that situation yesterday?"

<Where do I start and how much can I not tell her?> raced through his mind. "Uh...uh... Mrs. McMaster, a... a week ago I lost a bet with my sister and her friends and... and had to be their naked waiter one afternoon. Mrs.... Mrs. Wilson saw us... and... and said if I would serve... her... her garden party... she... she wouldn't tell..."

The principle watched the boy as he stuttered out his response and could tell he was only telling a 'partial' truth. "Strip!" she ordered, "I will not tolerate half truths or lies!"

David looked at the woman and knew she would accept no arguments and stepped out of his shoes, then removed his shirt with trembling hands, then unbuckled his belt. He looked up and saw a very stern face looking back at him, then unhooked and unzipped his pants and let them drop to his feet, then stepped out of them. David blushed deep red and his hands tried to cover himself.

"No underwear! You come prepared for anything, don't you; you perverted boy! Get those hands at your sides, I'll not have you playing with yourself!" Standing and walking around her desk, she looked over his hairless body and saw the red welts on his behind. "Seems like you've been punished. Who did that?"

"My sister, last night when I got home..." he whimpered.

Reaching out and running her hand over the welts, "Seems she did a good job. Why?"

"Because I let my wig fall off, and you and... and Becky recognized me..."

"Your sister is younger than you isn't she? Only about eleven, if I remember right."

"Yes Ma'am."

"How is it your sister is the one to punish you?"

"We... We have a deal... If... If I'm bad she punishes me rather than tell our parents..."

"So you let your younger sister punish you to avoid your parents finding out you are NOT the perfect little gentleman, everyone thinks you are is that it?"

"Yes... Yes Ma'am..."

"Get up on top of my desk on hand and knees," she ordered, shoving him forward.

David crawled up on the desk, and no more than had gotten on it when he felt something tapping his thighs, when he looked between his legs, he could see she was standing behind him with a heavy 'meter' measuring stick in her hand, "Open those legs wide," she ordered as she continued to tap the insides of his thighs. Once he had them as wide as he could get them, he felt her hand on his behind again, tracing the lines of the welts. "Yes your sister seems to know how to properly punish a bad little boy..." she murmured more to herself than to him. David was wide open, his balls hanging down low and his soft cock dangling in front of them. He knew in this position, is rear hole was also open since his cheeks were spread as wide as possible. His face burned knowing she was looking at his most intimate parts.

Her meter stick slid over his behind and then tapped at his balls hanging exposed, "I think some serious changes are in order David, you will not like many of them, but so what! It's no longer your choice. Are you listening David?" Tapping his balls hard enough to get an "Ouch!" from him.

"Yes Ma'am," he said with a groan as she continued tapping his balls with the stick.

"Good! Last night I reviewed your schedule and as of today it is being changed. All your classes will be in the morning starting tomorrow. Your teachers have already been advised that you would not be in class today. Each day after lunch, you will report to my office. I may or may not be present when you get here. Regardless, you will enter the storage room you saw me come out of, and undress in there. Then you will come into my office and get on the desk in the position you are in now; you will stay in that position until I give you permission to move out of it. Is THAT understood?" giving his balls a harder smack with the stick.

"Please Ma'am, that hurts!" he whimpered.

"Yes it does, doesn't it. Did you understand my instructions?" hitting again at his balls.

"Yes Ma'am... I... I understand."

"Good now some other changes. You are no longer in the Audio Visual Club, nor will you be taking gym. In short all of your study hall periods and other free time will be spent here or where I direct. You will also be taking Art; especially 'Life Drawing Class' three days per week; as you probably know, I teach that class."

"But I'm no good at drawing..."

"Ah... I understand that, but you see, YOU will be the model for my students. If you're real good, you'll get an "A" if not, well I punish bad models... and you wouldn't want that, now would you?"

"No Ma'am, I'll be good..."

Just then the telephone rang and David all but jumped from the desk in fright. "McMaster" the woman said into the phone as she stood beside the desk listening to who ever was on the other end. "I'll be right down." She said just before hanging up.

Picking up his clothes, she threw them into the storeroom and locked the door to the room. "I have to go handle a disciplinary matter David, you are to stay right here and not move unless told to until I come back." With that, she turned and walked from the room, closing her office door as she left.

David didn't know what to do, here he was naked in the principles office on top her desk on full display should anyone come in. Looking between his legs, he was shocked to see that her office door also had a window, and anyone in the conference room would be able to see him; fortunately he could not see the door to the main office so he was not visible beyond the next room. His whole body trembled as he thought about the implications of his new schedule; just what was 'life drawing' and who was in those classes? Naked every afternoon in the Principle's office? What if someone came in? Just then his thoughts were interrupted by the door to the office being opened.

"I wouldn't move if I were you young man!" he heard from behind him.

David looked over his shoulder and saw it was the School Secretary.

"Hello David, I'm Mrs. Carter the Secretary you met earlier. Mrs. McMaster said to keep you company while she's gone. I must say it's VERY nice to SEE you again. Now don't be nervous, you and I are going to become very well acquainted this year. Anytime the Principle is out, I am in charge of you and I just LOVE handling naughty boys like you." A hand closed on his balls without warning and crushed them. David screamed and fell onto his hands but remained on the desk, legs spread. "Now David, we can't have all that noise," she said with a purring voice and stuffed a cloth into his mouth, still holding his balls clamped in her hand. "You see David, I DO know how to control naughty boys... Are you going to be a good boy for me?

David vigorously shook his head 'yes' in reply.

"Wonderful, now why don't you turn over onto your back for me," she directed releasing her grip on his balls. "That's a good boy, now let's get those legs up and hold onto your ankles.... Good, now open them nice and wide, so we can see everything... Excellent! You're learning quickly..." The woman pushed his feet back so his knees were near his shoulders and he knew he was fully open and on display to her in this position. Once he was in the position she wanted, she opened a drawer and pulled out two pieces of rope and quickly tied his wrists to his ankles so that he was trapped in that position. Then lifting his right foot higher to expose even more of his behind, picked up the heavy meter measuring stick and proceeded to start spanking him with it. She was using her whole arm and putting her body into the strikes and David screamed into the cloth gag in his mouth, but little sound came out, tears streaked his face but even worse, when he glanced at the door, he could see three girls looking through the window, all with big smiles and he could hear laughing.

As she continued striking his behind, she calmly talked to him, "You know I really hate boys and men who act like little 'goody two shoes' but are really dirty perverts; I just don't get to do anything about it very often; so you will be a great relief to my pent-up frustrations." David moaned, whimpered and occasionally screamed, but she didn't stop. "Ah! You see my office girls do you? Well don't let that concern you, I have 18 girls who work in the office part time and all of them will see you at one point or another. Who knows, I might even let them help me from time to time with you." She said as she shifted her strikes to the underside of his thighs, leaving red marks and getting even louder muffled screams from him. After about ten more strikes to his thighs, she released his foot and stopped. "That should hold you until the principle gets back! Now just stay right there and maintain position until she returns." She ordered, then removed the gag and calmly walked from the room, leaving the door open.

For the next two hours David lay there on the desk crying and in pain, his rear and thighs on fire, unable to even rub the pain, due to being tied up. He knew it was two hours due to the class bells. Even worse, he would periodically hear giggles from the conference room and knew the 'office girls' were looking at him through the doorway. No matter what else might happen his life was now turned to shit and he could see no way out. Finally, the Principle returned and found him spread as ordered on the desk.

"Good, I see you and Mrs. Carter have gotten acquainted," she said with a smirk, then walked over and inspected the new welts on his thighs and butt. "Yes she does have a talent for dealing with miscreants..."

"Please Ma'am, what have I done to deserve this?" he whimpered.

"Well now David, for starters you are male and men have abused women since time began; next, the whole town thinks you are a wonderful and very responsible boy who really is just another sick little pervert; and last because you managed to get yourself into a situation were you have no choice but to comply with whatever we think is appropriate punishment for all of the above. Really, naked sissy maid to a bunch of old women and girls? What did you think would happen? So I and some other feminists and our daughters and relatives will turn your little perverted life around for you."

David had no logical reply so he just lay there crying before the smiling woman.

"Now David, I am going to untie you, but you are to lay on the floor beside my desk in the same position. If you are good, I'll have one of the girls bring you lunch. If not; well you wouldn't like what would happen... So I would strongly suggest you just lay there and be quiet while I work. After lunch we will introduce you to my Art Classes, then it should be time for you to go home. As I understand it you have a babysitting job this evening with my granddaughter, so you wouldn't want to be late."

She removed the rope ties and David gingerly got off the desk and assumed the required position on the floor beside her desk, his behind towards the door as directed and for the next hour and a half lay there. His legs were cramping and trembling from being in the awkward position. During that time six girls trooped in and out of the office, carrying papers in or out, all of them giggling or smirking at the naked boy, with the well spanked rear on display for them. Finally the Principle had one of the girls bring him a sandwich and he was allowed to break from the horrid position while he ate it.

When he had finished his sandwich, Mrs. McMaster told him to get up and handed him his new schedule and told him to study it. In addition to all of his academic classes being changed to one that met in the morning, he saw that on Monday, Wednesday and Friday he had Art classes scheduled in the afternoons and on Thursdays he was scheduled for 'Home Economics' which she hadn't mentioned before. She then unlocked the storeroom door and told him to go in and put his schedule in his pants pocket. As he did, she handed him a key, "This will open the hallway side of this room. From now on, you will come in from there, undress, leave your clothes in here and then come into my office." She then handed him a towel and just said "follow me," opening the hallway door almost before he could wrap the towel around himself.

David found they were in the hallway adjacent to the 'Art Department' rooms and he was quickly lead two doors down the hallway where she stopped at a door and opened it, directing him inside. "We need to get you ready for my class," she explained as he stepped inside. David looked around a saw a raised platform with two posts and a box like seat between them. Around the platform arranged in a semi-circle were 12 desks with wide slanted fronts, obviously made to hold drawing materials. David was lead to the platform and told to stand between the posts as she removed the box. Before he knew what she was doing, his left wrist and ankle were secured to the post on that side with leather straps and after pulling his right ankle out wide, it too was secured, then his right wrist. "Excellent! Just like DaVinci's 'Vitruvian Man,' I like it!" she exclaimed as she stood back and looked at him from the floor.

Not ten minutes later, the class bell rang and soon, students trickled into the room all but one were girls and all in his class. Each of them stood at the door when they saw him and either giggled or laughed as they recognized the nude boy tied in place on the stage. David burned from head to toes in shame as he heard whispers and giggles knowing they were talking about him. The worst were not so quiet "kind of small in the male department" and "No hair! Wonder if he's gay like Bruce?" Bruce it turned out was the only boy in the class and was openly checking out David's body with a leer on his face.

When the bell rang again, all of the students assumed their seats and got out drawing pads and charcoal sticks. "Attention class," Mrs. McMaster said loudly and all quieted down. "For the rest of this year, we will be working on Life Drawing and David here, will be our model. This week we will be recreating your interpretation of the 'Vitruvian Man' pose; then we will move on to other poses; any questions?"

"Can we enhance the body? He doesn't have much in the equipment area." A girl David had always thought was cute said with a snicker. His opinion of her turned 180 degrees as his face burned in embarrassment.

"Yes, I said YOUR interpretation, so you may modify the image as you see fit." The Principle responded; "Now let's begin..."

For the next hour David stood there spread wide, his cock and balls hanging down for all of his classmates to see as they began drawing. Occasionally one of them would get up and come close to get a better look at the details of his body; Bruce even took the opportunity to reach down and lift his cock and give his balls a little squeeze, while his own body blocked the view as to what he was doing. "Nice" he whispered, which just caused David to blush again.

Two of the girls saw what Bruce had done, and since he got no reprimand from their teacher took the opportunity to also explore his anatomy at close and personal range. One was Sally the girl who'd ask about enhancement. Her comment was devastating to him; "And to think I thought all these years you were cute; you need some definite enhancement there David, small doesn't get it..."

When the bell rang to end the class, David looked pleadingly at Mrs. McMaster, "Could I sit for a few minutes?"

"No David, but I have something which will help you. It's called a 'posing stand' models use it to help maintain position; but yours is special." She then went behind a screen and returned with a metal adjustable pole mounted on a square base; but atop the pole was attached a rubber cock like device. Without comment, she stepped behind him and used some kind of lubricant on his rear, then whispered "Just relax" as she worked two fingers into him and a minute or two later pressed the dildo up into him, slowly raising the pole as the device entered his rear. When it was all the way up, so that he could feel the wider base, she locked the pole and shoved the base directly under him. He was now not only tied spread eagle, but impaled on the rubber cock in his butt. Tears were flowing down his cheeks as the next class of students entered. This group were all a year older than him and included two boys; all of them walked close and looked him over, openly laughing at his predicament and laughing before assuming their seats.

The class began as before, but this group had no hesitation to walk up and run hands all over him, including his still limp cock and low hanging balls. One of the girls turned to one of the boys while she was holding David's cock. "Kind of limp here; hey Tony maybe he needs the REAL thing?"

Tony smiled back at her, "I'm willing, I like smooth twinks!" and everyone laughed while David's whole body blushed and trembled in shame.

"Perhaps next week if you're willing Tony," Mrs. McMaster replied surprising the student.

"No Problem Mrs. McMaster, I'd do that anytime..." he smirked in reply.

"Maybe in the mean time we should get a vibrating one for him. We'll see what we can arrange, maybe Bruce from the previous class will help out too," the teacher observed.

"I'm sure he would, he likes little smooth bodies too," Tony replied serious this time, "would you like me to talk to him?"

"Go ahead, three models together could be interesting..." she replied.

By the time the class ended, David knew he was going to be fucked at the least by one boy during next weeks' classes, maybe two in front of a bunch of girls his own age or slightly older; could it get any worse?

When he was finally untied, he walked forward to get the dildo out of him, his ass felt like it was wide open enough for a semi-truck to drive into it. Covering himself with the towel he was lead back to the storage room by Mrs. McMaster's office, with her following him. Inside the office, he was told to assume his position on the floor and she looked him over. "You did well today David, I think you are going to have a VERY interesting year, now as a little present for you being so good, I have a present for you," she said as she stepped to her desk and opened a drawer, and withdrew a flesh colored device. "This little butt plug will keep you ready for your posing stand on Wednesday, I want you to wear it until then, except when you go to the bathroom of course," she said with a very girlish giggle. With that said, she inserted the device and David could feel the 'T' shaped base along the crack of his ass. "Now go get dressed and you can go home when the bell rings." She directed and allowed him to get up.

On the way home, David discovered that the butt plug had an interesting effect when walking. It rubbed inside and hit a very good feeling spot and by the time he got home, he was hard as a rock and dripping pre-cum; so much that he had a wet spot on the front of his pants.

David had just entered the house when his sister arrived and immediately noted his hard-on and the wet spot on this front. "Interesting day David?" she asked.

"Horrible! The worst day of my life!"

"How so?"

And David recounted his entire day to her, the beating, schedule changes, Art classes, everything, ending with tears flowing down his cheeks.

"Poor David, let me see your behind," she responded stroking her fingers to wipe away his tears.

David turned around and lowered his pants, to show her the red welts on his rear and thighs and the plug in his rear. Jane gave the base of the plug a twist and got a groan from him, "Does that hurt?"

"No I just feel VERY full, and when I walk it rubs inside on a spot that makes me hard."

"Interesting effect. Change your pants and eat something, you are due at Becky's in an hour."

"I'll hold off for a couple of days but it's my income too. So deal with it however you have to, because I have plans for that money."

David just nodded and headed to his room to change pants.

Connie's Time

David was apprehensive as he approached the Petry house, it had been a long and hard day and he wondered what new humiliation he was facing inside. He'd no more than pushed the doorbell when it opened to a smiling Becky. "Hello David, right on time, please come in," she said with a smile, noting his hard-on, tenting his pants out and knowing the cause was a butt plug; then stepped to the side to let him pass. Once he was inside, she closed the door then moved around him and turned to face him. Without warning, she slapped him backhanded then drove her right knee into his crotch as hard as she could. David initially reached for his cheek then as the knee contacted doubled over and dropped to the floor on his side, gasping for breath as he clutched his aching balls.

"That was for all the babysitting jobs you've stolen from me over the past two years, you asshole!" she yelled, as her foot sought to kick his balls again, while he lay on his side.

"I...I'm sorry..." he choked out between sobs and winces at the pain in his groin.

"Not as sorry as you're going to be!" she yelled, then quickly shoved him onto his stomach and pulled his hands behind him as she sat on his back. Seemingly out of the air she had a rope and tied his hands together behind his back as he still was trying to breathe after the knee to his balls. By the time he recovered somewhat, his shoes were off and his pants were down to his knees, effectively trapping his legs. Using scissors, she cut his shirt up the back then both arms and removed it. Reversing position facing his legs, she then cut his pants off, leaving him only his socks. Using his belt, she started slapping his already striped rear while yelling at him about stealing her jobs. David couldn't move, she was as big as him and sitting on him with his hands tied, all he could do was squirm under her, crying out as each strike landed on his butt and thighs. Finally she stopped then looped the belt around his neck and pulled, choking him as she yelled for him to get up.

David managed to get to his knees, when she pulled the belt, leading him waddling on his knees like a dog leash. "Move it asshole, you belong to me tonight! After all, I hired you." she said jerked he belt. Once around the corner, they reached the living room and David saw a large metal cage sitting in the center of the room. It was the type used for large dogs and the grate was open. "In the cage!" Becky yelled, shoving him forward, her foot kicking him forward. David resisted but soon found himself inside the cage, only his ankles and butt still outside, when a foot on his butt pushed him further in, his head was bent down, it was the only way he could fit. Hands were on both ankles and he quickly discovered that Becky's sister Connie had arrived and both were tying his ankles to the sides of the cage, hands then reached in and looped ropes around his knees and they were pulled outward and also tied to the cage. He was now in a metal mesh cage, spread wide, his rear at the only opening, his sore cock and balls dangling between his open legs.

David was crying and pleading but neither were listening as he whimpered in the cage.

"What's that in his rear?" he heard the younger girl ask.

"A present from Grandmother," Becky replied, "She beat his butt at school today then made him model nude for her art classes, and put that in him before he left for home." As if to demonstrate, Becky pulled the plug out and showed it to her sister, then pointed at how his hole gaped open, almost winking at them, then jammed it back in, getting a yell from David.

Moving to the side of the cage, where David could see her, Becky smiled at him, "Comfy David? I hope so, because you are going to be there all night, until I get back from my date. Mom and Dad are out of town and won't be back until Wednesday."

"Plea...Please Becky don't do this..." he whimpered.

"Oh poor Davy, well you are here to watch my sister, but I can't trust a pervert like you with her young body, so you will watch her but from in this cage. Connie, on the other hand has permission to do anything she wants to you short of killing you."

"Please..." David whimpered, then seeing no reaction, just dropped his head to the bottom of the cage and cried as his body shook from pain and humiliation.

Becky rose and left the room while Connie just sat by the cage, reaching inside to feel his body, paying particular attention to his balls and cock hanging free and available. When Becky came back she was wearing a tube top and mini-skirt with high heels and looking very sexy. "Wow you look really hot!" Connie exclaimed as her sister walked to the head of the cage.

Meanwhile Connie kept playing with his privates and he was hard in her little hand, she stroked it up and down, milking him and soon he was dripping pre-cum, when he was right on the edge of cuming, she stopped and in a bored voice, said, "I'm hungry, think I'll get something to eat," and left him there straining but unable to get his cock to rub anything which might allow him to climax.

Connie had just finished making herself a couple of ham salad sandwiches when the doorbell rang. Carrying her plate, she went to the door and David heard it open. "Hi Sherry, Hi Buster come on in, Becky is gone for the evening on a hot date. Stay down Buster! Stay down! Good Boy!"

Sherry nearly fell down when she saw David crouched and tied in the dog cage!

"This is David, he's being punished by my sister for stealing babysitting jobs." Connie explained, "Come on in." she said leading her friend and her dog into the room where she could see better.

"Wow!" Sherry exclaimed, still shocked. She dropped the leash and put both hands up to her blushing cheeks. She managed to recover some as her eyes locked on to David's exposed rear end.

Buster a large German Shepard bounded right up to the cage, sniffing around between David's open legs and stuck his wet nose right against his plugged asshole. That nearly sent David through the roof but the girls were pointing and laughing hysterically.

"Looks like Buster found himself a new friend. Look at him sniffing around," Connie chuckled.

"Please get him away from me!" David pleaded as the dog kept sniffing him with obvious interest.

Suddenly Connie got an idea and took some of the ham salad from inside her sandwich and smeared it on David's behind. Buster didn't hesitate, he immediately licked the meat spread from David, once the dog had cleaned it, she got another idea and pulled his butt plug out the put a big glop right on his open hole and shoved her finger inside as she smeared more around the hole and then some down his crack and also coated his cock and balls with the greasy sandwich spread.

Buster didn't need to be told anything, the immediately nudged Connie's hand out of the way and licked at the hanging cock and balls seeking the tasty meat spread and it's greasy residue, then up the crack of his ass and around the hole.

"Please get him away from me, He'll bite me!" David pleaded, but Connie wasn't paying any attention, and pushed another big glob into his asshole leaving some outside to point the dog in the right direction. Then smeared more on his cock which was hard and straining from both her earlier manipulations and the dogs licking.

"Oh shut up you big baby!" she shouted at him, "or I'll let every dog in the neighborhood have a go at your pathetic ass." Then slapped his sore butt to make her point.

Both girls laughed and clapped their hands as the dog licked every drop of the ham salad out of David's squirming ass. When he was done, Buster continued licking all over his cock and balls getting every last taste of the meat, then returned to his open ass in search of more, forcing his tongue deep inside, causing David to squirm and twist his hips, as the tongue worked inside him. Tied as he was, there was no way David could avoid the dog all he could do was whimper, as the dog continued to probe him, licking his chops and whining.

"Here you go Buster we have more," Connie said as she took another finger load and spread it up and down the crack then took the remaining meat from her sandwich and shoved it in David's open hole and again coated his cock and balls. "That should keep him licking for awhile," she observed and both girls laughed as they watched the show.

Both girls watched and cheered as Buster dove right back in, cleaning the cock, then licking from the base of David's balls right up the crack, over and over, before dipping into his hole again with his long tongue. They giggled as they watched David squirm in vain to avoid the dog's tongue and taunted him when Buster put his paws on David's back and started thrusting his hips. The girls both noticed that the tip of Buster's red penis was visible between the dog's legs.

"Looks like Buster's found himself a new girlfriend!" Sherry snickered, and both laughed as they realized what was about to happen.

David realized it too, to his horror! He felt Buster's paws clamp around his waist and felt the thrusting of his furry legs against his backside. "NO! NO! GET HIM AWAY! PLEASE!" David was frantic. He was twisting his hips in desperation but he was tied wide open and helpless to stop what was happening. He felt the tip of Buster's penis rubbing along the gully of his ass. The angle wasn't quite right for penetration but Buster kept at it, trying to find a hole...

Buster was lifting his hind legs one at a time and practically climbing up the back of David's thighs in search of the correct angle. His tail wagging madly as his hips thrust. The girls were nearly hysterical as they encouraged the dog. "Come on Buster! You can do it! A little higher!... That's it! He's waiting for you... get it in there!"

Suddenly David felt the tip of the dog's penis pushing at the edge of his hole as the dog continued to thrust and maneuvered to get the right angle, then without further warning, he was in at least an inch and still thrusting madly.

"NO! NO! GET HIM OFF! PLEASE GET HIM OUT OF ME!!" David screamed

Buster was now going deeper and deeper with each thrust of his hips and was soon all the way buried into David. David was sobbing uncontrollably, tied, open and vulnerable, he heard the two girls laughing as they watched him getting fucked up the ass by a dog!

"Look at him go! Go Buster! Wag that tail and pump your girlfriend! HaHaHa!" Sherry cheered and Connie clapped, then got an idea and ran to her room for her camera. When she returned, Buster was still thrusting away his tail wagging as she took shot after shot of the boy being dog fucked.

"Please, get him off me! PLEASE!" David's voice shook as he sobbed and pleaded.

"Look at me!" Connie demanded, <click> "That's it!" <click> <click>

"Please get him out of me!" David sobbed. Buster's paws reached around his waist and touched the front of his thighs as the dog rode, his naked and bound body, pistoning tightly in and out of his asshole in short fast strokes. Just then Buster reached his climax and began pumping his load into David's ass.

"Ohooooohhh! STOP IT! STOP IT!" David sobbed as the dog wiggled and pumped. David could feel the hot spray against his insides as the dog's paws held him even tighter.

Both girls paused to watch this climax. They seemed to be holding their breaths in disbelief as the dog's thrusting finally slowed, then stopped. David's body shivered. Buster withdrew from his ass then the dog immediately ran and hid under the kitchen table. David lost it and just passed out totally exhausted and humiliated. David woke to the feel of his balls being pinched hard between small fingers and could see it was Connie sitting between his legs behind him. "Ooooohhh" he whimpered.

"Bout time you woke up!" she said then slapped his butt hard with her open hand. "Don't worry Buster's gone, it's just you and me... He's a very good dog you know and he sure gave you a lot of cum, it's all over your butt and down on you balls here." Just then she jammed the butt plug back in and got another yelp for her effort.

For the next hour Connie sat behind him alternating between spanking his behind with her hand and milking his cock or squeezing his balls. She never stroked him long enough to cum and he was hard throughout, moaning and pleading her to let him cum.

Finallly, he heard the door open and Becky was saying goodnight to her boyfriend on the porch, then reappeared in the room. "So David, did you two have fun tonight?"

David just whimpered, he was too far gone to talk.

Connie on the other hand recounted the evening's events including Buster's new girlfriend and pointed to the dog cum all over David's backside.

"Wonderful! I hope you've learned your lesson here David, I get first pick on all babysitting jobs from here on out or you will have another visit from Buster! Are we clear on this?"

"Yes Becky...." He whimpered, "Please... Please let me go..."

"Certainly David, it's time for you to go home anyway," then reached down and untied his knee and ankle on her side while Connie untied the other side. David slowly and painfully backed out of the cage, and rubbed his cramped arms and legs when she untied his wrists. Dried dog cum was everywhere, his balls were covered with it and his stiff cock had a crust of it.

"I can't....can't go out like this! I'm naked and it's three blocks home!"

"Sure you can! Now go!" she said shoving him outside, "I'd stay in the shadows if I were you though," she added with a giggle as she slammed the door shut and he heard the lock click.

It took him almost 45 minutes to make it those three blocks, having to hide in bushes each time a car approached to stop from being seen. One group of bushes were roses and he added numerous scratches to his already long list of injuries. He ended the trek by having to climb into his bedroom window, as he couldn't enter the house via a door since his parents were still up watching TV.

After a shower and douche of his behind using his mother's bulb to clean dog cum from his insides, he crawled into bed and cried himself to sleep.