Girlish

(A love story)

by Karen Singer

 

Chapter 2

 

I had finally gotten off the phone with Mom shortly after I got Jill's second shoe off. As I was struggling with the zipper in the back of the dress, Jill walked in again and said, "Here, let me help you." Then she stopped. "Wait a minute," she said, "what are you going to put on after you take this off?"

"I have a new pair of pajamas in my suitcase," I told her. "I don't usually wear them to bed, but I thought they might be a good idea for here. Looks like I was right."

"Let me see them," she said. So I pulled one of my suitcases up on the bed and dug through it and pulled out the pajamas, still in their package. "Yuck!" she said. "You're not going to wear those!"

"What's wrong with them?" I asked.

"They're awful!" she said. "Here, wait a minute. I've got something better." Then she dug into one of her drawers and pulled out a nightgown with small flowers all over it. The nightshirt she was wearing wasn't nearly as feminine looking as this one.

"I can't wear that" I said.

"Yes you most certainly can," she told me. Then she turned me around and unzipped the dress, pulled it off me and unfastened the bra for me since I was having trouble doing it myself. I was soon left standing there in just my underpants again. Then she pulled the nightshirt over my head and left me to put my arms through it while she hung up her dress. I guess I was doomed to spend the rest of the night dressed like a girl too. "Aren't you going to unpack your stuff?" she said at last since I was just standing there like I didn't know what to do with myself.

"Oh, good idea," was all I could think to say.

"When you're done, just put that package of pajamas back in your suitcase before you take it all downstairs to storage. I really don't want to see you wearing them – ever!"

I was just about finished putting everything away when Aaron knocked lightly on the door and then just walked in carrying a piece of rope and a plastic zip lock bag. I was very embarrassed to be seen standing there in that nightgown, especially when he smiled at me. He threw the zip lock bag, full of what looked like little plastic pieces, on Jill's desk and told Jill that she could expect a call from his friend sometime tomorrow morning.

"That's great, Jill said excitedly.

"I see that you've got Stephanie well in hand already," he said. "Let's see if we can help you with that other problem now." Did everyone really have to keep calling me Stephanie? I didn't say anything about it though. I was wearing a rather feminine nightgown after all. Maybe the name did fit – for the time being anyway.

"Great," said Jill. "How do you want to go about doing this?" she asked getting up off her bed.

Aaron turned to me and said, "Hold out your hands."

"Huh? What for?" I asked.

"We're going to do a little magic," he said to me. I don't know why (yes I do – it's because I'm stupid sometimes), but I held my hands out to him. He slipped a loop he had made in the rope over my wrists and tightened it, then without warning, he suddenly pulled my arms up high over my head and propelled me backwards up against the half open door. He pulled the rope over the top of the door then said "Up on your tip toes" while he pulled harder on the rope pulling me to my toes. He spent a moment on the other side of the door then walked around to my side and pushed me backward until the door was closed. I was stuck hanging there standing on my toes with my arms stretched as high as they could.

"What's going on?" I said suddenly very confused and a bit frightened. "Let me down!"

"In a few minutes," he told me. Then he went over to the desk and grabbed the zip lock bag. "Hold his nightgown up," he said to Jill. And with that, I suddenly found my underwear exposed again as Jill raised the nightshirt up out of their way. Aaron came over to me again and said as he was looking at my underpants, "Doesn't really look like there's much to bother with down there does it." And then with one quick move, he yanked my underpants down to the floor. "Looks like I was right."

I couldn't see what he was doing, but I felt him playing around my cock and it felt like he was attaching whatever was in the bag around my cock and balls.

"Watch closely," he told Jill as he showed her exactly what he was doing. Then he finally finished by saying, "Then you just put this lock on here and you're done. He can't get it off."

"Amazing!" said Jill. "He really can't get it off?"

"Nope," said Aaron.

"What do you mean, I can't get it off?" I asked. "What did you put on me?"

"Just a little device to make sure that you won't be causing Jill here any distress," Aaron told me.

"I wouldn't do anything like that," I said.

"And now, we know you won't," Aaron said to me. "And I'm sure that Jill will sleep a lot easier for it." Then he pulled my underpants back up into position. "See," he said to Jill. You can hardly tell it's there.

"No," Jill said. "I've certainly seen bigger packages in a man's underwear. But, in his case, it's actually making him look like he's got a lot more than what's really there. I'll tell you what I really wish though, I wish there was someway that we could make his whole thing disappear altogether, so that there's no bulge in his underwear at all. Make him look more feminine there."

"Hmm," said Aaron "an interesting idea. I like a challenge. Let me see what I can come up with."

"Take that thing off of me," I said angrily. "And let me down!"

"Oh, we're certainly going to let you down now," Aaron said, "but that device is staying on you. Jill here now has the keys and it will be up to her to decide when that thing comes off of you." Then he moved right up to my face and said, "So if you ever want any relief, if you know what I'm talking about, then I strongly suggest you do whatever she tells you to do." Then he turned to Jill and said, "Let me know if you have any trouble." And with that, he slowly opened the door pushing me forward on my tip toes as he did it. He untied the rope from the other side and pulled it back over the top to the inside letting my arms down. I was so relieved to get that pressure off. As he pulled the loop off of my hands, he said to me, "Oh one other thing, you can probably manage to pee standing up if you really try, but you'll find it much easier to sit down to pee from now on." Jill started laughing delightedly. Then with a smile, Aaron said "Chow," and left.

"What did he put on me?" I asked angrily as I pulled up my nightgown and pulled down my underpants to take a look. I didn't care how I was exposing myself at that point. My cock was encased in some kind of plastic cage. There was a plastic ring that went behind my balls and over my cock that the cage was attached to. I pulled every which way I could on the darn thing, but I couldn't get it off. "Please unlock me," I asked Jill finally. "I don't want to wear this thing. I promise I won't try to ever even touch you. I'm not that kind of person."

Jill had been watching me delightedly the whole time. "I know you're not, but that thing is staying on you. So if you know what's good for you, then I suggest you do whatever I tell you to. It's that simple. Now, let's take your stuff downstairs. I'll help you."

Reluctantly, I pulled my underpants back up and picked up two of my now very light bags while Jill picked up two smaller ones and I followed her down to the storage lockers in the basement. I felt very ashamed walking through the house in that nightgown, especially now with that device locked on me underneath. Fortunately, the only other person we saw along the way was Brenda who just stared at me. I'm fairly sure she was doing her best not to laugh.

A little while later I learned that it was definitely much easier to pee sitting down. I could manage it standing up, but I still had to pull my underpants completely down and then I would have to stand way over the toilet. Sitting down was really the only practical way.

In bed that night I also learned that it wasn't really comfortable to sleep on my stomach anymore. The hard plastic dug into me and hurt. I woke up in the middle of the night in a bit of pain. My cock had started to get hard and was being stopped by that device which didn't let it expand enough. It didn't take much before I had shrunk back down to being comfortable again. I would have to watch myself very carefully. I was used to masturbating every day either in bed at night or in the bathroom and I knew that eventually I was going to have a problem. I'd just have to see how things sorted themselves out. It was a long night.

The next morning, Jill "insisted" that I wear her pantyhose again as I got dressed for my first day of classes. At least no one could see the pantyhose since they were hidden under my socks and pants. I was concerned about that device showing through my pants, but Jill assured me that it couldn't be see at all. "In fact, you look more normal now," was how she put it.

 

 

INTERLUDE

 

As Jill came out of her first morning class for the day, her cell phone rang. "Hello," she said.

"Jill, this is Aaron's friend. He asked me to call you."

"Oh, wonderful!" said Jill excitedly.

"Are you free for lunch today?"

"Sure, I don't have any classes between 11:30 and 2:30"

"Then meet me at my office at 12:30. Go to the Curriculum Advisor's Office and ask for Ms. Carter. I'll tell them to expect you."

"Great! I'll see you then." The first day of classes was usually a wash and boring for Jill and her first class had been no different, but now things were definitely looking up. "The Curriculum Advisor's Office?" she thought to herself. That was interesting. She could hardly wait.

 

At 12:25 she was there introducing herself to the student worker at the front desk. "Yes, she's expecting you," the worker told her. You can go right back. It's the third office on the left."

"Geez," Jill thought to herself as she walked to the back office, "she actually is a school advisor. I hope I'm not going to get into trouble for this."

The door was open when she got there and she saw a middle aged woman seated at the desk inside. Before she could knock, the woman looked up, smiled at her and said, "Are you Jill? Come on in and have a seat. I'm just finishing up some paperwork. Oh, and please close the door."

As Jill sat down, she saw that Ms. Carter was a very attractive woman, probably in her early forties.

Ms. Carter finished the papers she was working on, threw them into a basked on the corner of her desk and looked up smiling. "Hi Jill, I'm Ms. Carter, as you know by now. I'm very happy to meet you. Aaron has told me a lot about you."

"It's nice to meet you too," said Jill.

"Before we talk about any… other things… that we can get into more over lunch, I took the liberty of pulling your file. I see that your previous advisor was Mr. Wilson."

"That's correct," said Jill wondering where this was going.

"Since Mr. Wilson is no longer with us, would you mind if I had you transferred to my list?"

"Not at all," said Jill surprised.

"Good, that way it will be easier if I need to help out and I can keep a closer eye on your situation. Just so you know, I've also taken the liberty of assigning Stephen to my list too."

"Oh, Ok," Jill said wondering where all this was going.

"Now, Aaron told me a little bit on the phone last night, but I want to hear it straight from you. What is it you're trying to do?"

"Well, I've been thinking about it all last night, and really, what I'd love to do is to make Steve as absolutely girlish as possible. I know it sounds silly, but if you could have seen him in my dress yesterday and if you just knew a little bit of what I felt when I forced him to wear it… well, wow! It's like I can't get enough of it."

"I see," said Ms Carter, "and just for the record, I think I do have some idea of what you're feeling. By the way, Aaron told me he was going to put a cock restraint on Steve last night. How did that go?"

"Oh my God!" said Jill, "it was great! You should have seen it. He can't get the thing off. And this morning when I asked him to wear my pantyhose to class, he just did it. I could tell he wasn't happy about at all, but he didn't say a word. He just put them on."

"Ah, so you've got him wearing something feminine under his clothes to class already."

"Yeah, I figured that no one could see it so it shouldn't be any trouble for him."

"That's true." Ms. Carter just looked at Jill for a moment then said, "Now, if I agree to let you do this… and if I agree to help you… then there's some things that you will absolutely have to agree to. Is that understood?"

"Yes," said Jill tentatively. She was a bit confused by the sudden change in direction.

"Now, for one thing, Steve was a late acceptance. Not that we don't think he can't handle the school work, but some of his scores were not quite as high as we would have liked, particularly his writing and math skills. You on the other hand have outstanding grades from your communications and math classes. So I expect you to make sure that his grades don't ever suffer. I don't want to ever see less than a B in his classes. Is that understood?"

"Sure," said Jill surprised. "I'll be more than glad to help him."

"Ok. Next… This is not something that he asked for or even wants and school life is about a whole lot more than just learning stuff from books. I want him to have a good social life. No ifs ands or butts. And don't worry, I know that not everyone will want to be around him, that's normal, but he absolutely must have a good relationship with at least some of the other students. I intend to keep a very close eye on him and I want to see him happy, despite what you're going to do to him. If I see any indication that he's being totally ostracized from everyone then I can guarantee that I'll not only put a stop to this, but I'll come down on you like a ton of bricks too. Understood?"

"Yes, sure," said Jill. "I guess that's only fair."

"Good," said Ms. Carter. "Now that we understand each other, are you hungry?"

"Yeah, starving," said Jill surprised again by another change in attitude and direction.

"Good, how about the Burger Barn. I'm buying."

"Great. I love that place."

As soon as they got into Ms. Carter's car, Jill noticed another personality shift take place. Suddenly, Ms. Carter was no longer business like and totally opened up and became quite chatty. "I just love turning men into pretty feminine playthings," she said gaily as she drove out of the parking lot. "I've been doing it since I was in college, and don't ask me how long ago that was." The rest of the trip Jill spent listening to a little bit of her history and experience which Jill soon realized was a lot.

The Burger Barn was a good 15 minute drive from the campus and by the time they got there the main lunch crowd was beginning to thin out. "Do you mind sitting out on the patio today?" Ms. Carter asked. "It's a nice day and we can talk easier there."

"No," said Jill, "that's fine."

As soon as they had been seated and had placed their orders, Ms. Carter looked at her watch, then took out her cell phone and made a call. "You know who this is. What's your status? Good! I'm at the Burger Barn seated at the patio outside. Find me, ten minutes!" Then she hung up. "I have a number of people that I take care of professionally, so to speak, and that was one of my newer ones. He's in his car and not far away, so I've just given him ten minutes to find me for a diaper check."

"A diaper check?" said Jill totally astonished wondering if she heard her right.

"Of sorts, with some of my subs, I punish them by putting them into diapers for a week. The only problem is that once I get them into diapers, they find it usually takes a whole lot more than a week to get out of them."

"What do you mean?" asked Jill.

"Well, I have a lot of rules and I'm very strict about enforcing them. I keep tabs on every one of my subs so that I usually always know where they are and what they are doing. And sometimes I either show up unannounced or more often, as you just saw, I call them and make them come to me. All I have to do is rub my hand over their bottom and I know if they are wearing a diaper or not and if it's wet.

"And I know that you're dying to hear some of the rest of my rules for them so basically it goes like this. They initially get put into diapers for one week. During that time, they have to label in permanent marker every diaper they wear with the date and the time they put it on. Then whenever they change themselves, they have to mark the time they took it off then fold the diaper so that the information can be seen. All their diapers have to be saved for me in a plastic bag until I can inspect them. I allow them time for a shower or bath, but otherwise, the times on the diapers all have to match up. I require that they have at least 5 diapers every day. At least one of those diapers must have a bowel movement in it and every single diaper must be pee soaked enough for my satisfaction. I don't want to see any dry or even barely wet diapers. I like to see them soaked. For every day that there's no messy bowel movement, they earn another 5 days in diapers. For every diaper that I don't think is wet enough, they earn another 3 days. Usually, during the first time I look over their diaper collection, they earn themselves about another two weeks stuck in diapers. They quickly figure out after that that if they ever want to get out of diapers again, they can't relieve themselves anywhere but in their diapers and they have to get used to them being really wet.

"Then just for fun, or in case I think they need some extra punishment, I pick a day – usually on a weekend, and increase their required number of diapers for that day up to seven or eight. Let me tell you, in order for them to meet my requirements for that day, the only thing they can think about for that 24 hours is finding ways to keep wetting their diapers, over and over again.

"By the time their diaper punishment is finally over with, every one of them is ecstatically happy to throw away all of their ugly male underpants and replace them with pretty panties – which they are then happy to wear permanently.

"The person that should be here shortly is now in his third week of this and is coming along very well. He's learned that he has to do whatever I tell him to do, no matter what that may be."

"Wow," said Jill, "but is all that really necessary? I mean, I'm sure that the diaper thing works great, but Steve has to room with me, and I'm not really interested in having that kind of mess and especially the smell around all the time."

"Of course not," answered Ms. Carter, "that's just something I do with some of my subs. What's really most important is for you to get Steve to do the things that you want him to do. You say that you want to feminize him, then that's the direction you need to be heading, and I think that you're off to a really good start. The biggest piece of advice that I can give you at this point is that you have to be strict, but fair with him. Reward him for doing something right, but also punish him for doing anything at all wrong. Don't be afraid to use your imagination. And you might want to go slow with what you're doing to him. You don't want him to be so scared he drops out of school.

"If I may be so bold, may I offer some suggestions for you to think about?"

"Please do," said Jill, "that's the biggest thing I need right now."

"Well then, I suggest you get yourself a notebook with a calendar in it to keep track of things. Such as what his punishments are and when they're supposed to be over. You might want to also keep track of a budget in there for Steve too. You're going to have to get him some new things and you don't want to abuse his money situation too much. Also, keep in it kind of a diary of your thoughts and ideas as things progress, not just what you did for each day, but also your ideas and wants for the future. By the way, you might want to have Steve keep a diary too, one that you can read, that expresses his thoughts about everything too. Don't punish him for his thoughts, but let him know that he can be free to express his real feelings there. That way you can track any mental progress toward where you want him to be.

"One thing that came to mind for me earlier is that you've already got Steve into pantyhose. Make him get more, and make him start to learn about different brands so he can develop his own sense of what type he likes. Also, in these situations, subs are usually started out in panties first so you may want to consider them as your next clothing item to tackle.

"And finally, since you've already taken a big step and gotten a cock restraint on him, you need to use that to your advantage. Set up a weekly relief session for him. If he's been good, then he gets to masturbate, if not, then he has to go another week. But when he does get to relieve himself, make it under your terms, not his. If he doesn't like it, then that's tuff. It should always be under your conditions.

"You might want him to write an essay before each session. If the essay isn't up to your standards, then he has to keep working on it till it is. He doesn't get any relief until it suits you. Possible topics might be things like: 'Why I Like To Wear Girls Clothes,' 'Why I Hate Boys Clothes,' 'Why I Want To Be A Girl,' 'Why I Hate Pants.' You get the picture. Mix the ideas up all the time, but make sure they're always pointed toward your goals for him. The idea is that over time, he will gradually convince himself that these are things he really wants too."

Just then, a young man hurried up to the table. Before he could even say hi, Ms. Carter saw him and said to him in a very no nonsense voice. "There you are. It took you long enough. Come over here." The man didn't say a word, but looking very embarrassed, stood close to Ms. Carter and allowed her to run her hand over his pants, front and back, to feel the diaper underneath. "Good enough," she said at last. "Now get out of here."

"Thank you, Mistress," he said giving her a small polite bow. Then he turned and hurried away.

Jill was astonished, but also let out a small laugh. "That was absolutely precious."

"Yeah, he's still embarrassed about it in public, which is something I like, but he's learned to trust me and to do as he's told."

At that point their lunch finally came and they spent the rest of their time together discussing details for Steve.

  

  

  

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