Marta led me to the cedar chest at the foot of the bed. She didn’t have to order me to kneel, just the pressure of her hands on my shoulders was enough to cause me to slowly drop onto my knees.
I watched her tie a cord to the hasp where a large padlock hung, then she quickly ran the cord through the hole in the end of the cock-gag that protruded from my stretched lips. I could feel the straps pulling at the back of my head as she tightened the cord.
Naturally this caused my head to be pulled down until the cock-gag was resting directly against the metal hasp. With my wrists cuffed to the rings on the leather collar that circled my neck I knew that there was little hope of me escaping now that my head was effectively secured like it was.
As this position only allowed me to see the floor directly below my head I was unprepared when she kicked my legs open and I dropped heavily onto the top of the wooden chest. It only took her a minute or so to fasten the metal spreader bar between my nylon covered ankles.
She tied a cord to the ring in the center of the bar then ran the loose end underneath me and up to the same hole that was tied to the metal hasp. She tugged on it several times which pulled my feet under me more causing my hips to angle up into the room at a sharper angle.
Marta and I had been living together for three years, ever since we had graduated from high school, but she had been tying me up, or down ever since we were kids. The first time I was 8 and she was 10 and she tied me to a tree in her back yard.
Once she had me bound so I couldn’t get away she tickled me until I wet my pants, then she left me like that all afternoon, not releasing me until it was time for me to eat dinner.
She now stepped back and looked me over. “Your such a pathetic little panty-waist!” She said, her voice tilled with disdain. ”I could to do anything I wanted to you right now!” She added.
As she had forced me to do ever since we were 11 or so I was dressed up in some of her clothes. A mid-thigh pleated skirt and a white linen blouse covered the lacy bra, feminine half-slip panties and nylons I was wearing under them.
I felt the back of my skirt move up my thighs and I knew that she was peeking under my skirt. “You look just like a real girl!” She exclaimed as she rubbed her foot along the smooth crotch band of my panties.
A strict leather penis harness held my tortured member back between my legs so my panties were smooth and flat like they were designed to be and it did make me look just like a real girl.
I inhaled sharply through my nose when she lightly kick her foot up between my legs so it landed squarely against my imprisoned balls. I heard her laughing as she watched my diaphragm tighten when my tummy was gripped by several sharp cramps.
“Oh I like doing that!” She chuckled then she kicked me again only harder this time. My breath was driven out of me and my abdomen spasimed as my quite severe cramps rippled out from my groin up into my chest.
As he struggled to catch his breath he thought of the first time she had made him wear some of her clothes. They were in his basement and she had talked him into removing all of his clothes and then putting on a pair of her lacy girls panties. Once he had done that she forced him to put on one of her old bras as well.
Looking at him in her lingerie she shook her head. ”Your a nasty boy for wearing girls underwear!” She said, adding, “You should be punished for wearing girls clothes!” After she had tied him over an old stool Marta found a wooden yardstick and she decided she should use to punish him.
SMACK SMACK SMACK SMACK SMACK SMACK
The loud popping of that stiff wooden yardstick landing across his bottom just barely drowned out his wails and cries as she continued to rain blow after blow on his pantied bottom. “Go ahead and yell!” She shouted knowing that both his parents were at work.
SMACK SMACK SMACK SMACK
She couldn’t stop swatting him and by the time she did stop he was sobbing real tears. She could feel her juices running down her thighs as her panties were to saturated to hold all that flooded out of her and she stood and starred at his bright red bottom for the longest time.
Finally she teased him about crying just as if he were a real girl. “Just think what the rest of the kids would say if they knew that you dressed up in girls panties and that you even worse a bra!” She suddenly said, her voice filled with glee.
“Please don’t tell them Marta. Please! I’d die if they found out!” He begged.
“I don’t know.” She answered. ”Maybe I should leave you tied down while I go out and bring a couple of them back her so they could see you for themselves!” She suggested.
She watched him struggle to try and get free as he was flooded with panic. ”No! They can’t see me! Let me go!” He yelled as he yanked and pulled at the cords holding him.
“Maybe I should call a couple of my girlfriends and tell them to come over here! I bet they’d enjoy looking at you and I wouldn’t have to leave at all!” She added with a chuckle.
James was on the verge of crying as he vainly struggled to get free. “No…….please no…….” He wined. “I’ll do anything you want only don’t do that! Please!” He begged.
Marta snickered. ”Anything James?” she asked. Without thinking he promised her that he would do anything a second time. “Hmm. Lets see. Well, since your a sissy from now on you’ll wear girls panties all the time!” She said gleefully.
He caught his breath. “I can’t do that!” He protested. “What if somebody finds out?” He asked in a worried voice. Marta shrugged and started for the wooden stairs.
“Well I gave you a chance.” She said, adding. “Your phone is in the kitchen isn’t it James?” She got to the third step and he was yelling for her to stop and saying that he would do what she wanted.
“I’ll wear girls panties! I agree!” He shouted in near panic.
“Good girl!” Marta told him moving in front of him. “But for being bad and giving me a hard time about it. The panties you wear are going to have to be your sisters. Your going to have to steal them from her dresser!” She told him.
“What if I get caught?” He asked.
“Then you get caught! So be careful” S he said.
Worried that she might tell some of the other kids he did as she wanted. Every day he would wait for his chance to dash into his sisters room and quickly grab a pair of her panties out of the drawer where she kept them.
It didn’t take him too long to decide that it was to nerve racking doing that every day. So on washday, after their mother had washed and dried most of the laundry he waited until all of her panties that had been in the wash were neatly folded and stacked with the rest of the clothes, then he took almost half of them and hid them in his room.
It took his sister about two days to start wondering where her underwear had gone but of course no-one suspected him of taking them.
Now that school had started again every day before classes Marta would take him behind the brick school building then make him show her the panties he was wearing.
She wouldn’t let him just unzip his pants either. She insisted that he open them all the way and then push them down to his knee’s so his panties would be completely exposed.
If his dick was hard she would take her hairbrush out of her purse and use it to spank his ass cheeks while she told him that he was a naughty girl for being hard. Several times he had trouble sitting in his chair once he was in class she had paddled him so hard.
One rainy morning he was standing with his jeans down around his ankles while she blistered his pantied bottom with her flat wooden hairbrush. She kept swatting him even after the school buzzer sounded and when she stopped she pushed him down onto the grass, then she pulled his jeans completely off.
“There! Now what are you going to do?” S he asked as she danced away so she was out of his reach. He begged her to give his pants back before someone saw him but she just laughed and threatened to leave him there like that.
“Oh god no Marta! No please! Let me have my pants back!” He pleaded.
She smiled. “Ok but only on one condition!” She said. “I know you like wearing girls panties so much that I want you to start wearing one of these all the time too!” Marta smiled as she held out one of her lacy bra’s.
He froze solid like a statue and his eye’s doubled in size. ”I can’t wear a bra!” He said not believing that she would even suggest such a thing.
Marta forced it into his hands. “It’s cold and rainy and you can keep your coat on all day.” She said, then added, ”And no matter what you say your going to wear it! And that’s that!” She didn’t seem very willing to discuss it.
“You better hurry up and put it on or you’ll be even later for class then you already are!” She warned with a wide grin. Partly because he wanted to submit to her and partly because he was afraid of what she might do if he didn’t he yanked his coat off then pulled his thick sweatshirt up over his head.
As quickly as he could he slipped the straps of the bra up his arms and then struggled to fasten the hooks. Once he had done that he put his sweatshirt and coat back on.
“See you can’t even tell you’ve got it on!” She told him as she looked him over. Once he was dressed again they both ran to class. Marta laughed when their teacher suggested several times that James might be more comfortable if he took off his coat.
She could see him squirming in his chair with worry that the teacher might order him to take it off, but he didn’t.
James was never happier then he was when school was over, but his torment had really just started. It seemed that the more outlandish things Marta made him do, the more things she thought up.
That day after school she tied his wrists to a pipe in his basement so his arms were stretched up over his head. With him hanging like that with nothing but his panties and bra she made him suffer through two full hours of her torturing and abusing his sensitive balls.
She squeezed them, punched them, pinched them with pliers, kicked them and she even hung a gallon paint can from them which she kicked so it swung in a big arch between his legs. When she finally stopped his small balls were purple and blue and he could hardly move his legs. But she rewarded him by stroking him through his panties. “You liked me doing those things to your ugly balls didn’t you?” She asked as she masturbated him. ”Admit it!” She yelled.
“Ye…Y..Yes.” He finally mumbled.
She shook her head. ”No, say it or I’ll stop!” She threatened.
His face turned a bright red as he gasped. ”I liked you hurting my balls.” He said quickly.
“That’s it!” She told him pumping her hands up and down his cock. “Say it again, louder!” She ordered.
“I liked you hurting my balls!” He yelled. She made him say it again just as the first spurt of pearly white sperm squirted into his feminine panties. ”Again!” She commanded as she milked the sticky fluid out into his panties. He did as she asked and by the time the final squirt of come shot into his wet panties he was thanking her for doing what she had done to his testicles. She released him then she gathered up his clothes and told him that he was going to have to go from the basement to the house wearing only those two items.
“Outside in a pair of panties and a bra?” He asked. She just smiled and nodded, then she gathered up the rest of what he had been wearing and quickly disappeared out the side door. James could feel the cold air on his bare thighs and back as he dashed across the corner of the back yard to the kitchen door. He started pounding on it when he found that it was locked while Marta stood on the other side and laughed at him for what seemed like hours before letting him in.
Then right there in the kitchen Marta made him use his mouth and tongue to suck and lick her pussy. She had taught him how she wanted him to do that and he was getting quite good at it. Her pussy juice flooded out of her, then down over his face as she shook from her strong climax. Then she made him use his tongue to lick her crotch dry. ”I want you to meet me at my house tonight at nine.” She told him as she pulled her panties back up where they belonged. “And I want you to be wearing my red dress and those high heels I gave you!” She added.
“How will I get out of the house wearing a dress?” He asked.
She told him that that was up to him to figure out. ”But you better be there and you better be dressed like I said or I’ll tell all the other kids about the things I’ve done to you!” She warned. Since it wasn’t a school night he lied and told his folks that he was spending the night at a buddy’s house. He waited in the garage after leaving the house and at ten till he put on the dress over his panties and bra then made his way down the alley to her house. At nine sharp he was standing in Marta’s back yard beside her bedroom window. He waved when she looked through the glass pane to see if he was there and a couple of minutes later she joined him.
“You look so pretty in your red dress James!” She said sarcastically as she looked him over. When she saw that her comment had made him blush she smiled. ”You like looking pretty don’t you James?” She taunted. He answered with a meek yes. After grasping one of his hands she held it very tight, then she pulled him over to the square playhouse her father had built for her years before. It was only four foot square, but it did have two windows and a real door, a door that she pulled shut after they had passed through it.
“I never would have guessed that you would end up enjoying being a sissy as much as you do!” She teased him in an obvious attempt to embarrass him. ”Lift up your dress and show me your panties!” She demanded. Like a well trained slave he bunched his dress up around his waist so his bright yellow panties were exposed. “You naughty girl, showing people your panties like that!” She exclaimed. She pointed to a padded kind of footstool thing and told him to lay over it face down. Submissively he did as she ordered and he remained like that while she tied his legs and arms to the four legs of the stool. He could tell by how tightly she had tied him that he couldn’t get free. “I’ve got a really special surprise for you James!” She said in an excited voice. “I stole this from my sisters dresser drawer!” She added holding up a rubber dildo.
“It’s what big girls use to make themselves come!” She told him. “But since your such a little sissy-girl I’ve decided that I want to use it on you!” His whole body began to shake. Marta had put her finger into his bottom numerous times before and he had found it kind of pleasant. But the thing she was holding up looked as thick as his wrist. “Girls have to get used to something this big being inside of them, so I don’t see why you shouldn’t have to as well!” She said. “I’ll just lift up your pretty dress so it’s not in the way.” She said teasingly then added, “And then pull down the backs of your cute panties.” He tensed up when he felt the pointed end press against his tiny hole. He wanted to yell for her to stop, to not do it, but he knew that his punishment for doing something like that would be worse then just letting her go ahead and do what she wanted. He couldn’t help crying out when he felt the intense stabbing pain flood through him when she thrust it forward. “Not so loud!” She warned. “You don’t want my dad to come out here do you?” She asked.
He gasped that it hurt and begged her to take it out. She told him that it was only in an inch or two as she moved in front of him. He watched her remover her panties which she promptly stuffed into his mouth. “That should quiet you down some!” She said with a nod.
After moving behind him again she began to shove and twist the rubber cock again and again until it had almost completely disappeared into his hole.
James was gritting his teeth from the pain that felt as if he had been ripped in two. ”You look sexy with a toy cock inside you like this one is!” she told him. ”I knew you could take most of it!” She added.
After letting it sit where it was for a while she began to slowly push and pull it in and out of him. ”I’m fucking you just like a real girl would be fucked!” she told him as she increased both the intensity an tempo of her fucking.
“You should like the way it feels.” She said. “Every girl does!” She was now fucking him hard enough at he was being forced forward an inch or so each time she thrust it into him. The painful thrusts were causing tears to stream down his face. “Does this make you feel like a real girl James?” She asked, moving one of her hands down onto the portion of his panties that was covering his cock. ”Do you like getting fucked like a real girl?” She asked as she started to stroke his dick through his panties.
Almost at once his hips began to move in rhythm with her hand moving over his dick. “Do you enjoy being a girl for me James?” She teased.
Much to her surprise he gasped that he did. “I love being a girl for you Marta.” He admitted, his words muffled by her panties. She pulled them out of his mouth, then made him tell her how much he enjoyed being fucked and that he wished he was a real girl.
“I’ll make you into a girl James.” she told him. “DO you want me to make you into a girl?” She asked. Hearing him tell her that he did want her to turn him into a girl caused her first climax to start gripping her tummy. ”I will James. I’ll make you into a girl and then I’ll fuck you like this every night! Is that what you want?” She gasped. She almost fainted when he told her that he did. “Wonderful. Then that’s what I’ll do.” She panted trying to recover from her orgasm. She really let him have it working his sissy pussy over for a good half hour. It was raw and sore looking when she finally let him come into the fronts of his panties.
“Something else is special tonight!” She said as she removed her necklace that had her name in small gold letters. She stood behind him and used a lighter to heat up the name part. “Don’t yell or my dad will come out!” She said and just as he was saying OK she pressed the hot name tag against one of his ass cheeks.
“Awwww…..” He started to yell but managed to stifle it half-way through as a soft hissing sound replaced it. When Marta pulled her necklace away there was a perfect brand of her name where the hot metal had touched him.
“I said for you to be quiet!” She scolded him as she brought her knee up into his balls. She quickly forced the dildo back into his pussy and after pulling his panties up and pulling his dress down she moved to the door.
“Now you’re going to have to stay like that all night just because you yelled!” She told him as she stepped through the door. “Maybe I’ll come down later and make your balls hurt some more since you enjoy it so much!” She snickered.