Her Terms

by Ronni

 

The day it happened I thought I would really like it. I had been cross dressing for quite a few years and had an extensive wardrobe. My girlfriend, Lisa, knew about "my secret" but had never seen me nor expressed any interest. In fact, quite the opposite, she said specifically that she really didn't need nor want to know.

Until that one fateful winter's day.

Lisa came in the door and greeted me as usual, "Hi, cutie!" We kissed hello, and moved into the den, where I had a nice warm fire going and an open bottle of wine. I poured us a couple glasses while we warmed up by the fire and chatted about each other's day.

"So, Ronni, I've been thinking." says Lisa

Strange, I thought, she's never called me Ronni before, always Ron or cutie. I wonder what's going on. I replied with a question "oh, what about?", and took a sip of my wine.

"You're 'hobby'"

"Which hobby, and what have you been thinking about it?"

"Your dressing hobby. I'm thinking that I'm finally ready to participate. But under my terms, and I get to say 'what' and 'when'."

"Really?" I was shocked, surprised, excited and in complete disbelief of what I just heard. We'd been dating for a few years and, although Lisa knew about my penchant for women's clothes, we never really talked about it and she certianly never expressed an interest in seeing me cross-dressed. Until now.

My mouth dropped to the floor. I didn't know what else to say, I just kept repeating myself "Really?"

"Yes, but you have to do everything exactly the way I say, and when I say. If you don't, then we go back to how things are now." She had that little smile that usually tells me she's up to something. I was still so in shock though that I didn't think anything of it at the time. "Think you can do that?"

"Sure, when and how you say. No problem." I was still dazed. Her smile grew bigger.

"Good, lets get started then. Lets go get you changed." And she got up and started upstairs. I followed, still wondering how i could be so lucky.

Lisa had me get out of my men's clothes. They weren't all mens, the jeans I was wearing were Gitano's, size 14, but who could tell? She told me to show her my panties, so I opened the top drawer of my dresser. She just nodded her head and smiled. "Well, go ahead, what's next?" I opened the drawers in succession, but hesitated on the bottom one, that's where some of my toys are. "Open it, cutie."

When I did, she quickly grabbed the butt plug I have in there and said "You didn't tell me about this! What other toys do you have?" She picked up the two movies in there, "Disgusting, these have to go. Ok, next."

Next was that she found my hypnotic trance cd 'Elegance', "Oooh, this is interesting, I think you'll listen every day from now on, maybe twice a day." Great, I thought, I like that cd but I'm not sure what long term use would really do to me. Guess I was about to find out.

I then showed her my corsets, waist cinchers and camisoles in the other dresser. Then came my closet. I already own 5 dresses (one really ugly and two way too small.) A number of skirts, plenty (I thought) of jeans, pants and shorts. And a few (too few) shirts. And 9 pair of shoes.

"Well, I'm glad your wardrobe isn't better than mine. What's in the box?" Shit! I was hoping she wouldn't notice that. That's where my maxi pads, tampons, dildos and kinky movies are. I tried to brush it aside, "I don't think I'm ready to share that just yet."

"You agreed, when and how I say. Get it down here and open it or this ends now." What could I do? I didn't want to end this, so I obeyed.

"Curiouser and curiouser. How often do you use this stuff?" Lisa asked.

I sheepishly replied. "Well, the pads almost every time I dress. The other stuff not quite as often."

"Show me." She commanded.

I grabbed a Kotex, while Lisa got out a matching bra and panty set. I put the panties on, with the pad, and tucked my prick between my legs, nestled in the pad. When I pulled my panties all the way up, I had a nice smooth front."Thats good, now the bra." She'd also found my padded inserts, and handed them to me after I hooked my bra. "I'm impressed, you hooked that without any effort. Ok, now your corset, I'll help you lace it up."

I was starting to feel a little embarrased, and said so. "Well, we can quit now then. Is that what you want?" It wasn't, so we continued.

"OK, now some pantyhose for you."

She had me wear panties, with a maxi pad, a bra, pantyhose and a corset all weekend. I wore women's jeans and t-shirts fairly often so she said I should continue to wear them as my "male clothes". Except, no sneakers. "Only pretty shoes for you, Ronni." She'd said.

After she took an inventory of my closet, she said we should go shopping, and handed me a purse, from my closet. It had the contents of my wallet, transfered to a women's wallet, complete with a spot for change. Plus some lipstick, a compact, a maxi pad, a tampon, a condom and a brush.

We went to get more pants, tops and skirts. We started out at Marshall's, figuring they'd have some fashionable clothing at a reasonable price. Lisa led me around the garment racks looking for pants, skirts and tops. All the pants had zippers either in back or on the side.

After finding a couple pair of pants and a nice flowing silky print skirt, a sales lady came around asked if we needed any help. Lisa volunteered "Yes, we're looking for some cute outfits for Ronni here. We already have some slacks and a skirt, but a few more, and matching tops would be great. Show the nice lady what you have already Ronni."

I was mortified, but also terribly turned on (and glad my little sissy clitty was well tucked away). I also knew better than to protest, so I showed the sales lady, Anne was her name, the slacks and skirt. "Oh, I know just what you're looking for." she said and took off, we followed.

She set me up with about 8 different outfits and Lisa made me try them all on in the store, showing her and Anne each one so they could check the fit and styling on me. I don't remember how I got through modeling any of it, much less the skirts, I was in a trance.

After I had paid for them, Lisa picked out a pair of navy pants that zippered in back, and a cream ribbed sweater, then asked Anne if I could wear them home. I just about died right there. Of course the sales lady, with a big smile, said that would be fine. Before we left, we also found a nice women's winter coat, not too feminine, and I wore that out as well.

Lisa laid out the rules when we got home:

I wasn't allowed to play with myself, ever - she'd found my "The Curve" chastity cage and locked it on using her own lock.

I would always sit to pee (a side effect of the curve is needing to sit to pee anyway.)

I would from now on always refer to my penis as a 'little sissy clitty'.

Furthermore, from now on I was to always wear:

panties with some type of feminine pad

a bra

either pantyhose or stockings

pretty women's shoes.

 

I would always carry a purse.

She would pick my outfits from now on. Nothing that I wear will ever again really be men's.

I would never be allowed complete masculine attire (which means at least something I wore would always be obviously feminine.)

Every day I would do the following:

listen to the 'Elegance' CD at least once but no less than 10 times a week.

pluck one eyebrow from each eye

shave my face with yesterday's razer then with a new razor

use only women's hygiene products (soap, shampoo, deoderant, razors etc.)

file my fingernails to smooth them but still allow them to grow

brush and floss my teeth

use a feminine body cream all over, especially my legs

always wear cherry chapstick (or lipstick), refreshing it frequently

use a feminine hand cream after every time I wash my hands

drink at least 64 ounces of green tea

drink at least 8 ounces of OJ

take my multi-vitamin

write at least a page in a journal exploring my feelings on being feminine

do at least 30 minutes of women's aerobics

Sex with her would be only after I'd agreed to a further dressing requirement (I also had to agree to clean her up with my tongue afterwards.)

Other rules to apply as Lisa deemed them necessary.

 

What was I getting myself into? To quote a famous song, "This could be heaven or this could be hell."

 

The First Week.

Every morning I would check my email to see what Lisa wanted me to wear (unless we happened to be together, then she'd just tell me.) Since I work from home, she had me wearing a skirt every day that first week. She also came by at unexpected times to inspect me. After a few days of that, she made me install a web cam so she could check on me more easily during the day to make sure I wasn't cheating. If I cheated, I would not be allowed releif for at least a week from the day of the infraction.

So every day that week, I did my required tasks. By the end of the week, it was becoming somewhat routine, but I still had to check off on my list what I performed each day so I could remember. I'm not sure if it was listening to that CD or all the other things I was doing, but I was definitely starting to feel more feminine, and submissive.

At the end of the first week, in order to have release from my Curve, I agreed to keep my toenails painted at all times. We then had some of the best sex we'd ever had. I ate her to three orgasms before she finally let me put my 'little sissy clitty' into her. I was still only allowed to cum when she told me to, and that would only be after she had another orgasm. I was desperate to cum, but knew I'd better now. Finally after what seemed like an hour later, she finally told me to cum, but by then I'd been concentrating on NOT cumming that I couldn't! After a few minutes of trying she said she was too sore and to please stop. So I got no relief. I still had to lick her pussy clean from her own juices.

 

The second week

The following week, she wasn't as tough on me. Most of the outfits she picked for me hid my bra and she allowed me to wear my jeans fairly often.

I of course kept up with my daily tasks, adding painting my toes to it. I found I was getting into a routine with it where finishing one task automatically let me to the next one.

We went out with our friends a few times that week. I had gone out somewhat dressed previously, so this should have been no big deal, but I was still very self conscious. Fortunately, none of our friends mentioned the purse I was carrying.

I kept my journal, which Lisa would periodically peruse, but never comment on more than a simple 'interesting'. I found I was writing about how I enjoyed the clothing, especially the undergarments. I was finding that having a routine actually made getting other things around the house done easier as well. I felt really good about myself and thought I was really lucky to have such a caring girlfriend.

At the end of the second week, I agreed to shave my underarms everyday in order to have relese again. I was again required to eat Lisa to three orgasms before entering her. This time however, I was able to cum when she said to. I had probably the biggest load ever. Lisa was very proud of me, then told me to get to work cleaning it all up. I had fantasized about this many times, but doing it was another matter. I gagged a couple of times, but managed to clean up all our combined sex juice. "Get used to it." was all Lisa said as she drifted off to sleep.

 

The third week

Went much like the second, mostly jeans and slacks with shirts that hid my bra. I was getting somewhat comfortable with dressing and I think she caught on to that fact.

That weekend she told me she had a surprise for me. She had me dress in some nice lingerie, a matching lacy white bra and panty set, a garter belt and nude stockings. Then a pair of cream slacks that zipped in back and had a flat panel front with no pockets. A red mock-neck ¾ sleave shirt, tucked in of course. And a pair of women's "tobacco" penny loafers. She also told me to put my diamond stud earings in (I had my ears peirced a few years prior to meeting her, so this wasn't a big deal either.)

We got in her car and she drove us to a strip mall. She then led me to the beauty parlor, and I was starting to get nervous. Inside there were a few women either getting their hair or nails done. Lisa talked to the receptionist in low tones that I couldn't hear. The receptionist checked her appointment book and nodded, smiling. I was really getting frightened.

Lisa waved me over to where she and the receptionist were talking. "Cutie, this is Amanda. She knows what I want, so you don't have to worry yourself about it, just do as your told and I'll make sure you're rewarded when we get home. I'll be back to pick you up in a couple hours. Have fun!" And she was out the door.

Amanda told me to follow her as she started towards the back. We went into the waxing room. "Strip" With great embarrassment, I did. "Nice lingerie, cutie" I could feel the heat in my cheeks. "On the table" I lay down on what looked like a doctor's office exam table. "Feet in the stirrups." I hesitantly complied, feeling very vulnerable and exposed. Another lady joined us and after Amanda introduced her has Jody, left.

Jody was an attractive mid-30 something. Nice pert breasts and a cute little ass in tight jeans. "Hi, you must be Ronni. I'm going to do a complete body waxing today. Just lie back and try not to cry out." She then proceeded to apply the hot wax and strips of cloth to my legs. I was not prepared for the first rip and let out a big "OW!" "Oh, that's just not going to do," Jody said, "we can't have you screaming for the next couple of hours. What can we do? I think I have just the thing." She left the room for a couple of minutes and when she came back was carrying something in her hands, "Close your eyes and open your mouth." I closed my eyes, but didn't want to open my mouth, until she pulled another strip off my legs that is. When I opened up to scream again, in went what must have been her panties as they were quite warm, a little damp and quite musky. "There, that should keep the noise down a bit." With that, Jody got to work with gusto.

After my legs, she waxed my privates (around the chastity cage), then my butt, my arms and finally my eyebrows (I don't have much hair anywhere else.) Finally, she smoothed some soothing cream all over me. My little sissy clitty tried to get hard, but the cage prevented that, mostly.

"Ok, all done, you can put your clothes back on now." Jody said "Oh, and give me back my panties." as she pulled them from my mouth. My jaw ached from being forced open for so long.

I was led back out front where I was seated at a manicuring station. My nails had been growing the past few weeks so they were fairly long by now. They were shaped and some slightly pink polish was applied. At a quick glance you couldn't tell, but anything more than a quick glance it was obvious I was wearing pink nail polish.

Lisa came back just about the time I was sitting to dry my now feminine nails. "Oh, Cutie, you do look so adorable. I love your nails, you're going to have to keep them like this for me all the time!" I just nodded, I was so embarrassed at this point, I couldn't say a word.

We left and went to get a bite to eat. Lisa had me pay, which forced me to dig in my purse for my wallet. I couldn't find it and with the waitress waiting, Lisa said "Cutie, why don't you just take the items out of YOUR PURSE until you find your wallet? It would be a lot easier and its what we girls have to do from time to time." Red faced, I consented, pulling out lipstick, a couple maxi pads and tampons, a condom, a hairbrush, a compact, some mascara, keys, cell phone, extra pantyhose and finally my wallet. The waitress was in stitches laughing and the tables around us were chuckling as well.

When we got home, she had me immediately change into a skirt. Then I ate her pussy while she watched television. That night, she released my from my cage and told me I could jerk off if I wanted to, she wasn't in the mood for sex with me. I was horny as hell, so I started to grab my sissy clitty. "Hold it, before you do, there are three things you need to know. First, you'd better make this last because the next time you're allowed to jerk off you'll have to do it in less time. Second, you need something in your sissy pussy before you can start jerking off. I don't care what it is (besides a tampon) but, each time you jerk off it will be at least the same size, or larger. It also is going to stay in you for at least 30 minutes after you've cum. Third and finally, you need to catch all your cum and eat it, a plate will work best for that, but its up to you. OK, now you can get the things you need and have at your little sissy clitty."

I was a little bewildered, but I meekly went and got a plate from the kitchen and a small vibrator from my toy box. I lubed the vibrator and worked it slowly into my sissy pussy. This, of course, wasn't the first time I'd done this, but it was the first with an audience. Lisa started s timer as soon as I grabbed my little sissy clitty (and stopped it each time I let go.) I alternated using the vibrator to hit my prostate and slowly jerking my little sissy clitty. When I began to leak cum, I caught it all on the plate. Finally, after about 10 minutes, I exploded all over the plate, covering it with a weeks worth of built up cum. After I recovered, I started to remove the vibrator but a quick swat of my hand and a stern "No, leave that in for another 28 minutes" I left it there. "Lick your plate, and don't swallow until the plate is clean and I say you can." I did as I was told, holding my cum in my mouth until the plate was clean. "Let me see" so I opened my mouth and showed her the cum pooled there. "Nice, ok, swish it around your mouth a few times, then you can swallow it." It was gross, and coated my teeth, but I did as I was told. "very good, another 25 minutes and your little buddy can come out."

I must have fallen asleep, because it was dark in the room and much later than it had been. I still had the buzzing vibrator in my bottom, but found that my panties were back on, as well as my Curve. My hands were tied at my sides, and I couldn't reach the vibrator to get it out. I was stuck until the morning when Lisa would release me. I tried to fall back to sleep but it was a restless night thereafter.

The next morning Lisa released me and told me that I should douche my sissy pussy before I shower, and to do so every morning from now on. So I did, and I added it to my list.

 

The fourth week.

Each day that week I would wake up, douche my sissy pussy, then shower, shaving all over to make sure I stayed nice and smooth. I was only using women's razors, shaving cream and body wash. After showering, I would put cream all over, then check for any stray eyebrow hairs and pluck them as needed. I brushed my teeth then put on cherry chapstick. Finally, I'd put my panties on, some type of hose and the outfit that Lisa had picked out for me that day - always something feminine, sometimes more so than others, but those were (usually) on days where I could stay at home.

I found I wanted to wear pretty matching panties and bras. On really cold days a nice pair of pantyhose was quite welcome as well.

When her period came this week, she decided I should have mine too. I was to wear a tampon and change it every 4 to 6 hours. And I was to douche after each tampon came out, before inserting the new one. Then it seemed as though she made sure I had some errands to run that week that would force me to change my tampon in a public restroom.

In the evenings that week, I would do 30 minutes of aerobics to the exercise DVD Lisa had me get. Then I would paint my finger and toe nails. If Lisa and I were together, I would do her fingers and toes as well, after giving her a good foot massage. I would of course still lick her pussy whenever she wanted.

The end of the fourth week had me agreeing to always wear mascara in order to be released from my Curve prison. Lisa had me lick her pussy but she just wasn't getting off. So she grabbed my "medium" sized vibrator and had me use that in her pussy while I licked around it as I pushed it in and out. She finally came and actually squirted around the shaft of the vibrator into my face. After she came down she had my gently lick her clean then told me to finish myself off, with the same vibrator.

So I took off my panties and slowly worked the vibrator into my sissy pussy. I was so horny, I didn't care if she saw how excited it made me. I worked the vibrator in and out, occasionally hitting my prostate, gently carressing my fingernails up and down my little sissy clitty. I'm not sure how long I did this, but I do recall having at least one spasmatic orgasm before I finally shot my cum all over my hand. It must have been less time than last week though, since Lisa never told me to stop. I pushed the vibrator back in as far as I could to wait out the required 30 minutes, then I licked my hand clean of cum.

Again, I must have fallen asleep, as I woke once again to find the Curve back on and the vibrator still buzzing away in my panty covered sissy pussy. My hands were of course tied so I couldn't reach it.

The next morning Lisa released me and told me that I should insert my butt plug after I shower, and to do so every day from now on. So I did, and I added it to my list.

  

  

  

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