The Perfect Pair Pt. 01

"Well, it's not just what I want, although it does excite me. It's what you want, isn't it?"

Dennis thought for a minute, "yes, I suppose it is. Like I told you, I have been dreaming of that since I was a teen-ager."

"And you haven't done much about that fantasy, have you? Well this is your chance. And I will help. I can help you experience being a girl. I must admit I like the idea. It will be fun for me too. You'll be like my old Barbie dolls."

Her enthusiasm surprised him, and he looked at her like he was trying to figure her out.

"What?" She said, "I love you and want to have fun making you into that lesbian lover I fantasized about. Remember?"

"Umm, OK," was all he could think to say to that statement, although his cock was certainly reacting, positively to the image.

He decided to move on. "OK, let's see the list again."

Brooke pulled her laptop back over and rested it on the arm rest slash table between their seats, so they could both see the screen.

"If we're going to be locked up in our chastity belts, aren't panties a little redundant?" He asked.

"Perhaps, but all proper women should wear sexy panties, and that's what we're shooting for, right?"

"I guess."

He nodded before continuing, "I do like the thought of you going commando, and of you naked all of the time," he said, and when she looked at him, he licked his lips, suggestively.

"Even though I'll be covered by the belt?" She giggled. "I thought you'd like that. I don't think I mentioned that I've always liked the thought of showing off my body, being an exhibitionist. I guess it's really an aspect of my bimbo fantasies."

"Bimbo fantasies?" Dennis asked, very interested.

"Well, yes. I've always been such a bookworm, and a nerd, I never really tried dressing sexy like some of the other girls in school. They seemed to get all of the guys, and have all of the sexual escapades. I was always jealous, and used to fantasize about going all slutty, like those broads."

"Well, I used to dream about those foxy girls when I was in school, but I never had the chance to date any of them. I'll be happy to hang out with bimbo Brooke. I like the sound of that adventure!"

She laughed, delightedly, "I'm not sure if it will be 'bimbo Brooke' or 'Brooke bimbo.'"

"Whatever. I'll be happy to go out with you." Dennis laughed,

"Good," Brooke replied, "but will you go out with Brooke bimbo while you're dressed as my lesbian lover Denise?"

That line stopped him dead in his tracks. Not the lesbian lover part, but the thought of going out in public, in drag frightened him terribly.

"Honey, that scares the hell out of me; going out in public, dressed as a girl. As 'Denise'."

"Dennis, we'll make sure you can pass. I'm sure we can. I'm confident we can make you look great as a woman. And if we can't, you'll just spend more time locked up."

She smiled as she delivered that threat.

He looked at her and just shook his head.

"I'm not taking it off the list." She said, authoritatively. She then just moved on to the last items on the top list.

"All right," he said pouting, but then he brightened up, "but I have an idea for another item to add to the list. I'm sure I'd like to see you spending more time as bimbo Brooke, around the house; for my own enjoyment. What if you earn a point for every 24-hour period you spend as a bimbo? You can even double dip. I won't mind."

She thought for a moment, "OK, I kind of like that idea. But how about a 12 -hour period?"

Now it was Dennis' turn to play hard-ball, "nope, 24. Remember you can double dip, so this has to be a bit more of a challenge. And, it does support your fantasy."

Brooke knew that she owed him one, and she was happy that he was contributing to the list, so she nodded, "OK, I'll add it, for the 24-hour period. But what about at night?"

Dennis smiled, "just like for Denise. Makeup and wig. Oh, and bimbo lingerie, too."

"Alright, sounds fair. I'll add it to the list. But you realize that it interferes with my going nude."

"I'll accept that."

Dennis reached over and kissed her on the cheek, pleased with himself for adding to the list. And one he was sure to enjoy, at that.

Brooke giggled. "So, you haven't mentioned the butt plugs."

As she said it, she realized that he hadn't read down the list that far.

Confused, Dennis quickly looked back at the list displayed on the screen. When he read the next item, he didn't know what to say. More like he couldn't say anything!

"Well you're the one that mentioned anal sex. Since that was your fantasy, I added it to the list. This is the preparation part. My bimbo persona kind of likes the idea, but I'll have to get used to the feel and get stretched a bit if we're going to try it. And, fair is fair, if this woman is going to wear a plug, Denise will too."

"Oh God," Dennis said, "I never dreamed of wearing a butt plug."

"Well, since I'll be wearing one, you should too."

"I'd be OK dropping that one from the list," Dennis said hopefully.

"Nope. For two reasons. First, bimbo me kind of likes the idea, and second, the fewer challenges we have on the list, the harder it will be for us to earn the points needed for release."

She paused and Dennis nodded, reluctantly. He was agreeing, mainly because Brooke seemed so enamored with the whole anal sex thing.

"And what's with this 'Denise' name?"

"Well, when you're dressed as a woman, you have to have a woman's name, and that works out so very well. Doesn't it?"

"I guess," he mumbled, but he did kind of like it.

When he read the next one, he was convinced that she really was planning on anal sex and he got excited. But then he read the last one and panicked!

It was all he could do to control himself and not scream, "What the hell is this last one? I have no intention of ever taking it up the ass! I told you, I'm not gay. Delete it!"

Having expected his reaction, Brooke was prepared. She grabbed his arm and held onto him as she spoke softly and reasonably.

"Honey, relax. I know you're not gay; that you're not interested in men. But you have to keep in mind that all of the things on the list are designed to reward us for kinky behaviors and motivate us to do them in the first place."

She paused, hoping he was calming down and listening to her.

"Like I've told you, I'm interested and willing to try anal, even though I've never been crazy about the idea. I could never figure out why a guy would want to stick it in my ass, when I have a perfectly good pussy. But I put it on the list, for me, to push me into taking a stab at it." She giggled for a moment at her own wording, before continuing. "That's why I set those tasks to award 2 points for the deed. To really encourage me."

She looked at him and was pleased to see him nodding, slowly.

"I guess I added it to the list for you, partly to get a rise out of you, and partly because fair is fair, and if it's on my list I want it on yours, too." She said, now convinced by her own arguments that she had been right to add it to the list, for both of them.

When he gave her a dirty look, she smiled back, and batted her eyes, like a flirt, "hell, you never know, Denise might want to try it, and we could use a fake cock, a dildo. I'd never expect you to get it on with a guy. So, let's just leave it on the list. You can forget all about it, I'm certainly not going to force anything on you."

Dennis sat for a minute, before just nodding and mumbling, "oh, all right."

Brooke, relieved to get past that issue, smiled and kissed him on the cheek.

"Great, thanks. If we can dream up any more to add, we should. Each one makes it easier for us to get out of our chastity belts."

"I understand, you're right." He said.

"OK, that's the first set of challenges. The rest are more like rewards for good behavior."

Dennis nodded, and started reading.

Brooke receives 2 bonus points per week for remaining hairless (entire body).

Dennis receives 2 bonus points per week for remaining hairless (entire body).

Brooke receives 2 bonus points per week for each bra size she increases her breasts with implants.

Dennis receives 2 bonus points per week for each bra size he increases his breasts with implants.

Brooke receives 2 bonus points per week for each body piercing instance, with approved jewelry.

Dennis receives 2 bonus points per week for each body piercing instance, with approved jewelry.

"Wow, these are real body mods," Dennis says as he studies the list. Not only are they big changes, but they also terrify him.

"I understand, that's why they're extra credit and recurring. They will get us our release much faster, and more often. That's good, right?"

"Yes, kind of," he replies, but doesn't seem convinced. "I've already agreed, more or less, to hair removal on my groin, but all over?"

"Why not? Some guys are practically hairless, while others look like Brown Bears. Most women prefer the former to the latter. And swimmers and weight lifters often shave their entire body. They look great."

She paused for a second, "And, Denise will look so much better, and more convincing if she's hairless."

Brooke paused again to give him time to think, and then continued, "look, hon, this is another one of those items where if it's good for me, it should be good for you too."

Unable to argue the fairness or dispute her arguments, he just nodded his acceptance.

"Good. Now you can't complain about the next one. As I told you, I've always dreamed of having bigger tits, and it will be an important part of my Bimbo persona, so I'm going to get implants as soon as we get home. I'm thinking of going for D-cups."

She reached over and punched him on the arm. "And what's good for me, will be good for you."

Dismayed and frightened, Dennis whined, "how can I possibly get implants? They might be fun when I'm dressed as a woman, but I can't possibly walk around in my normal guy clothes with boobs! That one just won't work!"

"Wait a minute! Now listen to me. Small implants, that would take you to a B-cup, can easily be hidden under your man clothes with a sports bra. No one will ever see them. The coolest part will be when you're cross-dressing. With a padded bra you can look like you have C-cups and you'll be amazing. You'll have a wonderful woman's chest. It will make it a lot easier for you to pass. Think about how cool that will be."

By the time she had finished with her speech, she was leaning over and looking intently at Dennis, face-to-face.

He was shocked by the forcefulness she displayed. It was kind of overpowering.

Still staring into his eyes, she spoke quietly, "and I will love having another pair of breasts to play with. You see, this is for you as well as for me. Please do this for me, and for Denise."

Dennis couldn't resist, even though he wanted to. The thought of having real breasts turned him on and Brooke's request added to his arousal, so he sighed and whispered, "yes. I'll do it for you; for us."

Her face lit up with a huge smile, "I love you so very much. We're going to have so much fun."

She sat back, then, still smiling, "now how about the last ones? These were your idea."

Dennis slowly looked at the last two items on the list.

"Piercings?" He asked, unsure.

"Yes, silly. You told me how fascinated you are with pierced women, so I added it to the list. Here again, I think my inner bimbo came out when I added them. You see that the more piercings we get, the more points we get and the faster we'll earn our release."

Dennis was admittedly turned on by pierced women, so the thought of Brooke with piercings got him excited, and incidentally took his mind off of breast implants. He started day-dreaming of Brooke with a pierced navel with some dangling jewelry, and with pierced nipples with big rings,on the tips of D-cup breasts. As he sat there hugely aroused, he started reaching for his crotch.

Brooke sensed his feelings and slapped at his hand, "stop that!" she whispered, giggling.

Dennis jumped, and blushed as he realized what he had been doing.

"You can see that you will also be getting piercings, right?" She asked.

"Oh shit!" Dennis mumbled. His mind was back in a muddle.

"What did you have in mind for me?" He asked, apprehensively.

"Well, I did give that one some thought. I won't grant myself any points for my already pierced ears, but you can start with that. By the way, I consider piercings that come in pairs to be a single instance, like ears, or nipples."

The mention of pierced nipples got Dennis distracted again, and he just muttered "OK".

When he pulled himself back to the conversation, he realized that they'd reached the end of the list.

"No more?"

"That's all I came up with. Do you have something to add?" She asked, chuckling.

Dennis thought for a minute, "No, I can't think of anything more, I think that's enough. But I do have a couple of questions on them. Consider them clarifications."

"OK, shoot."

"Well, when I'm dressed as a woman, what does that mean? Makeup, wig, dresses and heels?" This was an exciting point. It was, of course the main aspect of his cross-dressing fantasies, so he wanted to concentrate on it for a few minutes.

Brooke replied, "yes, of course, all of those and polished finger and toenails, and jewelry, and stockings, and above all else, only dresses and skirts. And those must be above the knee, and feminine if not just plain sexy. There will never be any slacks, jeans or shorts of any kind."

Just hearing the requirements so defined got Dennis all excited, again. Brooke could see it, and giggled, "sounds good, doesn't it?"

"Yes; and at night?"

"In bed you'll wear a very feminine negligée, of course. But only in bed. No flouncing around the house in only your night gown. And you'll wear a wig and light make-up. I want to be able to see you as a woman when you're in bed with me."

"But it will be a mess by morning," he said, concerned.

"Not if we get the waterproof and smudge-proof kind."

He smiled and nodded.

"OK, what else? Any other 'clarifications'?" Brooke prompted.

This time it was Dennis' turn to smile, devilishly, "let me tell you what Bimbo Brooke will wear."

Brooke nodded excitedly, "OK, shoot."

"Bimbo Brooke will always wear heavy makeup like she's going clubbing; she will wear only short skirts or dresses, at least 3 inches above the knee. Her tops will reveal her massive cleavage. She will wear nylons and a garter belt. I'm afraid our chastity belts will prevent corsets, but she'll wear a waist cincher if she can. Her shoes or boots will have 5-inch, spike heels. Her nails will have long extensions, and her long wig will be brassy blond or perhaps deep red. Of course, she won't ever wear a bra or panties."

"Panties are somewhat superfluous, though aren't they?" Brooke said. It was really a rhetorical question so no answer was expected.

Now the both of them were deeply aroused, and they could each see it in the other. It made them giggle like a couple of kids.

"Ohh, that all sounds wonderfully kinky." Brooke gushed.

"Yes, it does, doesn't it?"

"I may have to wear a support bra while my surgery heals, will that be acceptable?"

"Yes, that will be allowed, but only until you're healed."

They sat quietly for a few minutes, each lost in their fantasies.

Finally, Dennis spoke up, "next question. What cup sizes did you have in mind?"

"Well for you, as I said, I thought you'd go for a B-cup, that could be hidden under your man clothes."

"OK, I guess." Dennis replied, surprising both himself and Brooke.

"And for me, with a D-cup, we'd each earn 4 points per week. We'd reach our release goals in no time."

Dennis nodded acceptance, "alright. I guess," shaking his head, astonished at what he'd just agreed to. "Next, please explain what does 'out in public' mean?"

Brooke looked at him a bit confused, "It means just that. Out shopping, or to a restaurant or a movie, or whatever. Out doing things like two married people do."

Dennis just had to ask, "like a lesbian couple?"

Brooke smiled, "yes, at least sometimes. You could decide to forego the points and go as my man. Just like I might decide to go as just plain old me, although I can't see myself passing on the points, or the opportunity to go out as bimbo Brooke."

Dennis smiled, happily at her answer. He was really excited about bimbo Brooke.

"OK, one more question, not really a clarification, though. Can I not do the butt plug? I don't need to practice for anal sex. I'm really pleased and excited about trying it, but..."

He trailed off as he saw Brook's reaction. He knew what she was going to say before she even opened her mouth.

"You will do the butt plug if you want the points, and if you want me to try anal. Remember, if you pass on those points, you'll delay your release, and will be subject to the loser's penalty."

Dejected, Dennis surrendered, "alright, I'll think about trying it. Fair is fair, I suppose."

He paused again before he continued.

"If we go with that scoring plan, it could take weeks or even months to earn those 50 points. I think that's way too long, to wait for relief. Looking at the ways we can earn points, especially until we start earning the recurring rewards from the second set, it could take months to accumulate 50. I can't wait that long."

He stopped, and reached over placing his hand on Brooke's thigh. "I simply can't. I'll go crazy."

Brooke laughed, "that's the whole idea with chastity belts, silly. Keeping you horny and building up to a huge release. I think you're being a drama queen. You won't go crazy. You'll survive. I bet in your fantasies you imagined yourself going for months without cumming. Admit it."

Dennis, sighed, "yes." But remained dejected.

Seeing his reaction, she hesitated and thought for a while, while he waited, hopefully. It didn't take long for her to realize that he just might be right. That probably was too high a mark, especially without the points they'd start accumulating after their piercings and implants. She didn't want to spoil that fantasy for either of them.

"Oh, all right. It might be a good idea to ease into it." Brooke said.

Dennis let out a big sigh of relief.

"OK, what if we start with only 30 points for the first goal, and then add 5 points each time we make our goal from then on. It will be another aspect of the game. The longer we play the game, the harder it will be to earn relief. I like it." Brooke said with glee.

"But we'll stop at, say, 40, right?"

Brooke thought for a moment, "I think 50 would be better. After that we'll have to talk about it but I think it might be fun to keep increasing it by 5. Perhaps to 100."

"Oh wait. That scares the hell out of me!"

"Don't worry, honey, we'll have plenty of ways to earn points and get our release. And the longer it takes to hit our goal the more delicious it will be when we do get there. This is all about enforced chastity, after all."

"I suppose." He said. He was terribly aroused by the whole concept, but also very frightened. It was one thing to fantasize about being locked away with no sex for weeks on end, but a whole different thing to actually go through with it.

Dennis then leaned back in his seat and closed his eyes while Brooke began entering in the adjustments and notes from their discussions.

Analyzing the various rules of the game in his head, he came up with a couple more complications, that he wanted to talk about.

"What about when we have to fly somewhere? TSA will give us a load of shit about our belts. It will be awfully embarrassing."

"Well, we'll just have to deal with it," Brooke replied. But seeing that Dennis was still not happy, she continued. "OK, I'll tell you what. Let's award a bonus point for each flight, to soften the blow. How would that be?"