Author Topic: Trapped (Read 39403 times)

DaraJaney · « **on:** November 26, 2008, 03:24:01 PM »

After his Granny died, Ian moved to her house with his mother. She had kept his mother’s room just as it was when she was a girl. Many of her dresses were still there.

Since he reached puberty Ian has noticed certain feelings when he sees a pretty dress. He often wonders what it would be like to wear one. He tried to dismiss such stupid feelings but he can’t help it sometimes.

He wandered into his mother’s old room. He sneaked a look in the wardrobe. Hanging there were her dresses, protected in transparent plastic covers. He listened to hear if his mother was near before reaching up under one of the covers and feeling the lace.

“Like it?” he heard his mother say suddenly from the doorway. He jumped back. “S-s-s-sorry.” His face went red. His mother looked at him curiously. “Seriously, do you like it?” she asked, looking at the yellow dress. Ian was flustered. “It’s ok if you do”, she assured him. He looked at her uncertainly wondering if it was a trick. “Some boys do”, she said. “There’s nothing wrong with it.”

Ian couldn’t admit it but he was reluctant to deny it either. He wondered would she possibly mind if he tried one on but there was no way he was going to ask that.

“Would you like to try it on?” she asked. His stomach wrenched. His little member started to swell as it always did when he thought of this. He couldn’t bring himself to say yes but when she reached into the wardrobe and took out the dress and held it up to him, he didn’t back off like most boys would.

“I think you’d look lovely in it. We kept all these dresses but I’ve never had a chance to dress a daughter up in them”, she said wistfully. “Why don’t you let me dress you up a little. It’ll be our little secret.”

Ian’s member was expanding exponentially. His mother took his lack of protest as consent. She put the dress on the bed. She went to a drawer and took out a pair of white knee high socks and then fetched a pair of black t-bar shoes. “Go on”, she said. Ian was embarrassed that she might see his erection. “OK but I need to do it alone first”, he said at last. “Fine”, she chirped and left the room. “Call me when you’re ready.”

His stomach was churning as he put on the dress, shoes and socks. He looked at himself in the mirror. He looked like a boy in a dress but he loved it. He swished the skirt around, walked back and forth studying himself in the mirror.

“Ready?” his mother called from outside. He braced himself. “Yes, Mum.” She came in. He stood most uncertainly in front of her, expecting her to burst out laughing. But she just smiled and said “lovely”. “Walk up and down a bit.” He duly obliged.

It was clear he was in no hurry to take it off so she said nothing and he continued to wear it around the house. He ended up wearing the dress for the rest of the day. It was a dream come true. But when he undressed he found his briefs were saturated from the effects of his erections during the day. He hid them at the bottom of the laundry basket.

DaraJaney · « **Reply #1 on:** November 28, 2008, 06:27:21 PM »

The next morning his mother came in and suggested he wear another dress. He didn’t object. This time he wore a blue dress. She suggested a pair of plain white panties. Again he was mortified that he wanted to wear them and couldn’t say “yes please!” like he wanted to. But she knew the story and left them on the bed for him.

He loved wearing the dress all day but his testicles were aching by the end of the day due to all the stimulation.

“You can continue wearing dresses all the time, as far as I am concerned”, his mother told him. He smiled and nodded. Once again he carefully hid his panties in the laundry basket.

The next morning he was still asleep when his mother came in. He was barely awake when she threw back the covers. “I’ve noticed that you’ve been making a mess in your panties”, she said sternly. He was too embarrassed to say anything. “Never mind. This will solve it”, his mother said.

She took a plastic tube and pulled it over his limp pen-is. He watched curiously. She put a plastic ring around behind his ball sacs and he heard a click. When she took her hands away, he could see a little padlock. She had locked his equipment in a short, thin plastic tube that curved downwards and had a hole in the end. “That’ll do it”, she said.

She pulled him from the bed. “I think we can make you look even prettier!” Ian was excited. She took a pair of white tights. He thought girls looked so stupid and sissyish in white tights but he was curious to wear them to see what they felt like.

His mother pulled the tights on him. Ian felt excited at the prospect but he was not getting the usual stimulation. He felt his member pressing again the sides of the plastic tube. His mother flapped out a pair of frilly pink pettipants. Ian nearly drooled. She pulled them up over his tights. But he could only feel numb down there.

Then his mother produced a pettislip. Ian had never seen one before and was mesmerised. She pulled it over his head and fluffed out his petticoats. Then she selected a pink polka dot dress with an attached pinafore with starched lace trimmings.

She pulled it over his head and zipped him up. She carefully arranged the skirts of his dress so they fell evenly over his petticoats. Ian couldn’t believe that this was happening but his excitement was completely numbed by the device on his member.

His mother pulled out another drawer and produced a pair of ankle socks with delicate fluffy lace around the tops. She pulled these over his tights and buckled on a pair of t-bar shoes with a three-inch heel.

Ian tottered slightly when he tried to walk. He had to push back his petticoats and stick his foot out to be able to see the lace on his socks. His mother gave him a pair of lace-trimmed white gloves and he pulled them on. Then she handed him a large doll.

He stood in front of the mirror. He looked like a six-year-old girl visiting her doting Granny. He couldn’t believe that he was wearing a pretty pink dress over petticoats, tights and frilly panties.

Before his interest in this developed at puberty, he would have thought a girl like this looked like the dumbest thing in the world. In fact, he still did but for some strange reason it thrilled him to look like this.

But it was very considerably dampened by the restraint on his member. He was so absorbed by the clothes that he didn’t fully appreciate that he was getting no sexual satisfaction from this at all.

DaraJaney · « **Reply #2 on:** November 30, 2008, 02:11:03 PM »

He kept hoping that an erection would come but it was clear that the device was going to keep his tights and panties dry by denying him any stimulation at all.

He turned to his mother. “Do I have to wear that thing?” He was too embarrassed to explain why he wanted it removed. “Absolutely”, she replied. “I can’t have you staining my lovely old clothes. Now let’s do something about your hair.”

She took his hand and brought him somewhat reluctantly to the bathroom. The longer it went on, the more he realised that he wasn’t really getting much satisfaction from this at all.

She sat him on a chair, put a towel around his neck and washed his hair. Then she rubbed stinky lotions in. “What are you doing?” Ian asked, getting frustrated now. “Wait till you see!” his mother said excitedly.

She started winding his hair around metal rods. He wasn’t in front of a mirror so couldn’t see precisely what was going on but he wasn’t happy. “Here”, she handed him an old catalogue of girl’s dresses from her time. He was fascinated. “Ow!” he cried out as she pulled his hair too tight. “Sorry! No pain, no gain.”

He was engrossed in the catalogue and distracted enough to stop crying out as his hair was tugged this way and that. Then he noticed his head getting warm. “What’s going on?” “This is the last bit”, she assured him. He went back to the catalogue.

After what seemed like an age, his mother started unwrapping the rods. She took two pieces of thick pink ribbon. “Perfect.” She pulled him up out of the chair and turned him towards the mirror.

His jaw fell open. His hair was twisted into dozens of tight ringlets. They were tied up on either side with the thick pink ribbons tied in big bows. He now looked like a four-year-old! In one way it was enthralling but he was getting no thrill from this at all because of the device.

“Mum, can I please take the thing off. It’s hurting”, he lied. It was uncomfortable having his member press tightly against the plastic but it didn’t hurt. It was just completely dulled.

“No. It’s locked on there as long as you’re in dresses and I’m keeping the key.” Ian sighed. “Well, I don’t think I want to wear dresses anymore”, he protested. “Don’t be silly”, his mother dismissed him.

He looked in the mirror. The complete sissyness of his pink dress, pinafore, petticoats, tights, frilly panties, frilly socks, high heels, ringlets and ribbons should have had him reeling but he felt nothing. Just stupid.

“I want to take this dress off”, he decided. “Nonsense”, his mother responded. “I’ve just given you a perm. Those ringlets will be there for two weeks at least.” He was shocked. “What?” “Well you said that you were happy to continue wearing dresses.” He sighed. He did, didn’t he? And now he didn’t want to anymore.

DaraJaney · « **Reply #3 on:** December 02, 2008, 06:12:04 PM »

“I still want to take this off and put on my trousers”, he insisted. “Ah well, that could be a problem”, his mother said somewhat sheepishly. He looked at her curiously. “Why?” “Well, you said that you were happy to stay in dresses.”

He glared at her. “What have you done?” She looked at the floor. “I gave away all your boy’s clothes.” “You what?!” “You SAID”, she reminded him.

“But I didn’t mean permanently!” He looked down at his dress. “I’m sorry”, she said. “I seem to have misinterpreted.” “Misinterpreted!” he shouted. “That was some misinterpretation!”

He thought of the frilly dresses in the wardrobe. They were all he had to wear now. The previous day that thought would have filled him with excitement but he felt nothing now but humiliation. His member pressed desperately at its tiny prison and he got no thrill whatsoever. “I don’t believe it.”

“Mum, I beg you, can you take off this device?” “I told you, it stays on as long as you are in dresses”, she insisted. “Which is permanently”, she added.

He was speechless. He was going to have to wear pretty dresses permanently now and get no pleasure from it at all.

“It’s nearly time for Church”, his mother reminded him. He looked down at his dress. “You can’t seriously expect me to go out like this!” “Why not? You have to wear your prettiest dress for Church”, she insisted.

“I’m not going anywhere dressed like this!” “Oh yes you are young lady”, she insisted as she took his arm. “The last service is in 10 minutes and you have to go. There’s no time to change anyway.”

She opened the front door. He tried to dig his heels in but he stumbled in the three inch heels and she pulled him outside. He desperately tried to turn and run back in but he heard the click of the door closing. “Please no!” he begged. He stomped his foot and she smiled at the way his ringlets danced and his petticoats shook. She started walking down the path.

He couldn’t stay where he was. People would come past. He had no choice but to follow her. “Please Mom. I look like a four-year-old. People will wonder what’s going on.” Just then a couple came out of the next house.

Ian had to stop talking. He didn’t want to be identified as a boy in this sissy outfit. His mother continued walking and he had no choice but to follow her, right towards the other couple. They looked uncertainly at Ian and then obviously stifled a laugh. “Well hello”, the lady said. “You must be our new neighbours. What a pretty dress.”

“That’s right”, his mother said. “This is Susie.” Ian was mortified but he had no choice but to play the part. He smiled shyly and wrung his hands. They walked on.

As he tottered along in his heels trying to keep his petticoats down in the wind he realised that he had no choice but to be a sissy girl now. All he had to wear were his mother’s pretty dresses and the neighbours all thought he was a girl. There was nothing he could do. He was trapped in dresses and his member was trapped in a device that made sure that he got no pleasure out of this at all.

At church his mother went right up to the front row. Ian could feel everyone’s eyes burning holes in his back. He fiddled continuously with his unfamiliar petticoats. He was highly conscious of his dumb tights, frilly socks and ringlets. He desperately hoped that people couldn’t see his pettipants but he knew the dress was very short.

He tried to feel arousal from down below which he normally would just thinking of dresses but there was nothing but numbness.

Outside the church his mother chatted away to anyone who would stop. Ian shifted from one foot to the other, his heels beginning to give him pain, while everyone filed past and took a good look.

That night before he went to bed he examined the chastity device. A hard plastic ring was fixed behind his ball sacs with a plastic post running through it to prevent it being opened. That post was locked to the plastic tube that went over his pen-is. He shook the little pad lock in frustration. He tugged at the various bits but they were securely held in position and there was no way he could play with himself while this was locked on him.

He lay down and thought of the ultra-feminine clothes he had worn that day – and would wear the next. His member started swelling until it almost immediately met the confines of the plastic tube. No matter how much he thought of the frilly panties or the petticoats, he could get no more arousal. He squirmed in the bed, pulled at the hard tube and tugged at the lock again but it was hopeless. He lay there for at least another hour in total frustration.

DaraJaney · « **Reply #4 on:** December 05, 2008, 06:41:25 PM »

The next day his mother put him in a lavender dress which had layers of netting underneath. He fidgeted all morning. “What’s wrong?” she asked sternly. What was wrong? Only that he was condemned to wearing dresses while his boy’s member was completely neutralised.

“This netting is very uncomfortable”, he protested. “It’s like sitting on sandpaper.” “Even through your tights?” she asked. He nodded.

“Well why don’t you go outside for a walk then? That will save you having to sit on the netting.” He frowned. He really didn’t want to go out. “Go on. You need the fresh air.”

She made him go to the front door. He fiddled with the netting under his dress which was sticking out awkwardly since he stood up. “There’s nothing to do out there”, he protested. She handed him his large doll, opened the door and pushed him out. “Don’t come back until you’ve walked around the block.” The door slammed behind him.

It was breezy so he placed a steadying hand on his dress, clutched his doll tightly and walked reluctantly down the path. He looked over his shoulder and saw his mother check out the window that he was doing what he was told.

Walking round the block involved going through the village. He braced himself and tried to walk quickly but his three-inch heels forced him to take little steps.

He passed two girls, about 10 years old playing on a swing. He heard them titter as he passed. “Oh my gawd”, he overheard. “She’s supposed to be sixteen!” “Looks more like six, hee hee hee!”

The other side of the village he turned right past the football field. There were boys kicking a ball around. They stopped when they saw Ian. He heard wolf-whistles. He started to scamper quicker in his heels and they laughed.

So his miserable existence continued. He had no idea how to dress or act as a sixteen-year-old girl so he had little choice but to follow his mother’s instructions. He knew she was dressing him and making him behave as if he was half that age but what could he do? The fact that his member was so thoroughly neutralised seemed to have also knocked any fight out of him.

His mother was quite delighted with the turn of events. She smiled out the window seeing him sitting on the garden bench working on his embroidery. She had taught him to sit demurely with his back straight and knees together. His high heels forced his feet at a dainty angle. His new tights with pink hearts down the side were very pretty.

She too reckoned that keeping his member tightly packed away made him more compliant and she had every intention of keeping it that way, despite his regular pleas. She loved having him in pretty dresses but that would be ruined in her mind if she knew he was sporting erections underneath those frilly panties. But this way she knew that he was getting none of that disgusting stimulation.

She smiled as he brushed his ringlets away for the umpteenth time. They constantly got in his way when he bent his head to peer closely at his embroidery.

So he spent the rest of the summer in pretty dresses and his member remained unable to respond in any way. His mother had complete control over him and was able to dress him any way she pleased. Any remaining resistance had been stifled in him. She somewhat guiltily took advantage of this – like putting him in a frock that was hopelessly too short to conceal his pink pettipants for example.

He would endure the taunts stoically and simply scamper along as quickly as he could, clutching his doll a bit closer for comfort.

[concluded]