Dolly's Diary

sissy challenge accomplished!

Dollyanne completed her weekly sissy challenge today! It wasn't an especially difficult challenge, but dolly wanted to start on something she could accomplish. The challenge was to dress up as a sissy boi and buy two pair of panties and two thigh-high hose from a shop where exotic and topless dancers go for their scandalous outfits!

It was cold outside, so dolly decided to dress in layers. Layer 1 was her pink period panties and maxipad with facial cream covering her clitty and 2" clitty ring. Layer 2 was cream-colored panty hose which dolly was able to pull up past her belly button. Layer 3 was a pair of girl's black velvet loungers with a tie-string in front and hot pink stripes down the sides, matched with a 3/4 sleeve pink cotton blouse with pink polka-dot white cuffs and collar--very sissy!

Dolly wore some aqua-blue girlie socks to keep her tootsies warm in her powder blue girl's Nikes. Because of the cold weather, dolly had to wear a little jacket over it. It wasn't a girl's jacket, as dolly doesn't have one (yet!), so dolly had to wear a tan boy's jacket along with a girl's baby blue velvet and satin cap! The jacket was zipped down so dolly's pink and white blouse showed through. Dolly also brought along her girlie powder blue wallet and a tube of sissy pink lipstick to apply before going into the shop.

Dolly's anticipation was building as she drove to the shop in her sissy boi outfit. Who would be there? Would they laugh at dolly? Would they kick her out? Before dolly could get too worked up about it, she realized she didn't have a discount coupon! The 20% discount coupons are available as cut-outs in a topless dancer paper that is distributed at adult book stores. Dolly needs to be frugal these days so shopping without that coupon would be a no-no.

That's when dolly remembered there was an adult book and novelty store just down the street from the shop. So, dolly decided to go there first, get the paper, cut out the coupon, and then go to the shop.

Dolly parked directly in front of the adult shop, locked her car and went in. Dolly remembered the paper stands were located near the exit, so she would have to go into the store, through the videos and magazines and around the counter to get there. Dolly was worried about the pink-striped loungers and, of course, the panty hose were hidden, but the pink and white blouse really stood out! It was partly covered by the jacket, but anyone who looked would know immediately that dolly was wearing a girl's cap and blouse.

Dolly worries were unfounded. Despite the cars out front practically no one was in the store part. Everyone was back in the arcades watching the porno videos (and probably doing a few other naughty things too!). Only a couple of clerks--a girl and a boy--were in the store behind the counter. One of dolly's future challenges will involve going into the arcade, but for now, dolly had free rein in the retail store part.

Dolly hadn't been there in a while and noticed a lot of new toys! So, curious dolly decided to do some browsing. A couple of people did come out of the arcade area and give dolly some funny looks, but for the most part, they ignored her and let her browse.

Ten minutes later dolly showed up at the counter with a "rear-ender" and some nipple "suction" cups. Dolly had read about both of these on the chastity mansion forum. The former was being used by petal130 for prostate milking, and a form of the later by maid_katrin for nipple enlargement and sensitizing. Thanks to both of you for these suggestions!



Dolly got the girl clerk so she asked her if they happened to carry any chastity devices like the cb-2000. She gave dolly a peculiar look, like she didn't know what that was, and then said, "No we don't have those." She also said she didn't know anyone in the area who carried them.

So, dolly exited the store with her purchases and picked up a topless club paper from the stand near the exit. Dolly tore out the 20% coupon in her car and proceeded to the exotica shop.

Dolly parked outside the shop and applied her sissy pink lipstick using the rear-view mirror, rubbing her lips together to even out the lipstick. It was still cold so dolly kept her jacket on and went into the store. It was like a candy store for sissy gurls! Maid's and school-girl uniforms, micro-minis, platform high-heels, wigs galore, and of course, panties and hose.

Dolly was greeted by a female clerk immediately asking if she could help, so dolly said she wanted to look around, and asked what, if anything, was on sale. She led dolly to the sale bin which had panties and thongs and other things on sale, some for 99 cents! Dolly chose a pair of patriotic red-white-blue bikini panties and a pair of super-small break-away pink thongs. These must be what the dancers wear on stage! Dolly was worried that they would be too small for her, but she couldn't pass up the price!

The hose--mostly fishnet--was against the wall and dolly spent quite a bit of time surveying it. Dolly ended up selecting two very feminine pair--one with a red ribbon on top, and the other with pink stitching running down the back of the leg.

Then dolly looked around the store at other things--the maid uniforms, the micro-minis, the wigs, and the platform high-heels. Dolly's eyes were bugging out of their sockets at all the pretties and she could see new challenges in store for future purchases involving trying on things!

Dolly went to the counter and asked if the coupon would work. The girl clerk was quite friendly and said she would check with the manager in the back. The manager--another girl maybe a couple of years older, came out, punched a few buttons on the cash register, looked at the coupon, looked at a picture on their display, glanced sideways at dolly, and finally concluded that yes, they could accept it.

Whew! Dolly was relieved. She even threw in a tube of pink lipstick as an impulse buy from a display on the counter (only $1.99!). The clerk picked out a nice hot pink one for dolly! After the discount, dolly's total purchase of two pair of panties, two pair of thigh-high hose, and a tube of pink lipstick came to just a tad over $8!! What a deal!

Dolly got a few stares from the girls and other customers in the shop, but dolly is pretty practiced at ignoring that by now. Dolly knew that they knew dolly was getting these things for herself and that they really didn't care. They had seen trannies and sissy bois before and had Queen sizes in lingerie and high heels in size 11 and above just for them. In fact, in these economic times it should be even easier than ever for a sissy gurl to shop!

So, that was dolly's first challenge with a bonus! Now she is ready to stretch her nipples, try prostate milking, and wear her new panties and hose! Stay tuned for fun ahead!

It was relatively easy for dollyanne to accomplish, and not as thrilling as the one lauren wrote about, but subsequent challenges will get more and more difficult and humiliating for dolly and she may not be able to carry through on all of them. (A couple of them make dolly blush even now.) In that event, dolly will have to accept punishment instead. Such is the life of a sissy gurl in training and dollyanne loves it!

Curtsies and Huggs,:manga_love:
dollyanne

 

Thank You, Mistress Watchful! Dollyanne, of course, feels that she has almost nothing to wear! Dollyanne has too little to have complete outfits, yet too much to keep everything properly hidden. It's a quandary! Maybe dollyanne can get some more pictures soon.

Yes, it's a great shop and dolly is very lucky to have it in the area! Here's the online version where You can shop to Your heart's delight without jumping on a plane: Electique-Boutique

After her challenge, dollyanne realized she forgot one of the most important things she has that she could've and probably should've worn--a bra! Dollyanne has a nice pink one. It would've made the challenge more difficult and blushingly humiliating for dolly to wear a bra. A sissy-boi with a bra!

And, in hindsight, dolly should've taken her jacket off. It was cold outside, but dolly could've removed it in the store. If dollyanne had a real Mistress She probably would've insisted on it!

But still, Mistress Watchful, the level of the challenge was such that dollyanne could execute it successfully, so it was a good first step for her. Dolly expects some challenges will be easy and some will get more and more difficult to the point where dolly will lose her nerve and chicken out and have to take punishment instead. This area of the country can be a bit risky for a sissy gurl, so dollyanne does have to be a bit cautious sometimes.

Thanks for Your gracious comments, Mistress Watchful. Here's some coffee to start Your morning:



Curtsey,:manga_cloud9:
dollyanne

 

Dolly's bad luck continues

Dollyanne not only didn't get a chance for a cummie because of her 7-day period, but also got this from virtual Mistress when she requested a reward for completing her sissy challenge:

su 07 11:43:16 AM --Permission to Ask for Challenge Cummie Reward granted (50%).
su 07 11:43:21 AM "Sorry dolly, No CUMMIE reward this time, but..."
su 07 11:43:24 AM "You may buy yourself a new pair of panties!"

So, now dolly must wait until tomorrow to see if she gets a chance for a cummie. Dolly will also get a new sissy challenge tomorrow for the week. But, at least there is a bright spot. Dollyanne gets to shop for a new pair of panties. And dolly knows right where to go! There's a pink and white frilly pair she's been lusting over. If they're still there and still on sale, dolly will get them and will be able to wear them since her period will be over tomorrow! So, panty shopping here we go!

Curtsies and Huggs,:manga_bunny:
dollyanne

 

Thank You, Miss D! Dollyanne tries her best to be frugal--especially in these times--so she can shop more. Dollyanne LOVES to shop! Unfortunately, the pink and white panties were gone when dollyanne got there! Dolly ended up getting a soft blue paisley pair with red lace. And, right next to it was a hot pink bikini panty with black cross-lace on the front and "SEXY" written on the back. They were only $1 on sale, so dolly got them too!

And, thank You for reminding dollyanne about the bra. Dolly is sooo frightened to wear it in public, but will definitely remember it next time. Dolly needs more bras, but the one she has is a nice pink 38C padded bra--perfect for dolly!



Curtsey,:manga_washup:
dollyanne

 

Sissy challenge

Sleepy-eyed dollyanne awoke this morning and got her new sissy challenge for the week from virtual Mistress:

mo 08 8:20:36 AM "It's time for your sissy challenge, slut!"
mo 08 8:20:42 AM "You will DO the challenge or you WILL be punished!"
mo 08 8:20:45 AM "It is what you WANT, what you CRAVE, what you NEED to grow as a SISSY GIRL."
mo 08 8:20:49 AM "That's why you WILL OBEY!"
mo 08 8:20:51 AM Do you want ME to chose your sissy challenge for you, sissy girl?
mo 08 8:20:59 AM "No, Ma'am, I would like to choose this time"
mo 08 8:20:59 AM What sissy challenge would you like today, dollyanne?
mo 08 8:21:09 AM "Get a pedicure"
mo 08 8:21:09 AM "You WILL dress like a sissy boi, go to a nail salon, and..."
mo 08 8:21:13 AM "Get a sissy pedicure!"
mo 08 8:21:16 AM "Don't forget to ask about manicures, dollyanne."
mo 08 8:21:20 AM "And, get all the information on waxing, GIRL--you will need it!"
mo 08 8:21:26 AM Did you load your dolly clothes?
mo 08 8:21:31 AM "No, Ma'am"
mo 08 8:21:31 AM "If you don't load them now, SLUT, you'll have to type things in like the BIMBO you are!"
mo 08 8:21:35 AM New status: normal
mo 08 8:21:35 AM "Load your dolly clothes and start your day, dolly."

Actually, dollyanne chose the challenge herself from the list rather than get a surprise, because she thought it would be good to get a professional opinion on her poor toenail! Dolly noticed a new nail salon having a grand opening nearby offering a 30% discount, so dolly chose that challenge for the week.

OMG...dolly must dress like a sissy boi and go there to get a pedicure! Dolly will ask about what products or treatments they have for dollyanne's toenail and is also supposed to ask about manicures and waxing. Dolly has NEVER gotten a pedicure before and has NEVER even been in a nail salon, so this will be a special thrill for dolly if she can follow through with this sissy challenge! Dolly is sooo apprehensive, but sooo excited! Wish dolly luck!

Curtsies and Huggs,:manga_angel:
dollyanne

 

Thank You, Mistress Watchful! Dollyanne was sooo excited this morning about her period ending and her trip to the salon that she went out the door with her panties on backwards! She thought they felt funny, but she didn't notice until later. They are white boy shorts with pink polka dots and white bows and dolly was sooo excited to be wearing pretty panties again.

It seems odd, but dollyanne even felt sexy with her panties and her period ending. Dolly doesn't have a real period, but just simulating one seems to be giving her her similar feelings!

It'll be later in the week when dolly visits the salon, assuming she is still brave enough! Dolly drove by there today and peeked through the window. It was scary--like an alien world. Well lit with comfortable chairs meant for pampering GIRLS. Wow! Dolly is frightened, but must get her courage up and think about her poor toenail!

Curtsey,:manga_bunny:
dollyanne

 

Thank you chastityslavejohn, but dolly's not that brave! It sounds like you have a wonderful Mistress. The Giants play the Cowboys tomorrow! Dollyanne bets you're going to look good in those blue toenails!

Huggs,:manga_sack:
dollyanne

 

Thank You for the encouragement, Miss D! These are excellent ideas! Dollyanne went to the salon earlier in the week, so unfortunately, dolly didn't have Your suggestions in hand. Here is a summary of dolly's time at the salon, which so far, hasn't worked out so well:

Dolly dressed in her black velvet loungers with the pink stripe with panties underneath of course, a pink 3/4 sleeve top, and blue and white striped girl's Nikes. Regrettably, dolly did not have her bra on. It was locked away in a difficult-to-reach place and dolly was in a bit of a hurry. Next time though, dolly WILL wear it! (Dolly has it where she can get it now!) Dolly did have her girlie cap and her shoulder purse though!

Dolly also didn't get any pictures, so dolly must do that next time also. (Dolly is feeling sooo inadequate here!) Dolly has to go through some gyrations--boy clothes on top of girl clothes to get out of the house--remove the boy clothes in the car--and then put them on again before coming back to the house. Quite a production! So, dolly will have to work out how to get pictures before going out--perhaps in dolly's private bathroom.

The first salon was the one advertising the 30% discount. Dollyanne donned her girlie cap and proceeded inside carrying her shoulder purse also. There were no customers in sight! The owner (dolly guesses)--a Chinese guy--approached dolly with a big smile and asked, "You want manicure or pedicure?". Dolly tried to explain her toenail problem to him, but to no avail. He continued to parrot the same phrase over and over again as if he hadn't heard a word dolly said. It was like talking to an alien robot who only knew one phrase. He said, "You want manicure or pedicure?" to everything dolly said. Dollyanne got frustrated and finally decided to leave.

At the second salon (across the street in a strip mall) dollyanne also encountered a Chinese guy at the reception desk (are all nail salon owners Chinese?). Dolly tried explaining the same thing to him, and he was having difficulty understanding. He got one of the girls to come over (Chinese also!). Dolly removed her obviously girlie Nikes and aqua-blue fluffy socks so she could look at dolly's toenail. She immediately said, "Your shoes too tight. You have to let grow out."

At this point dollyanne realized that a pedicure was not in the offing. She is going to have to let the offending toenails grow out, which could take a little time. This shop had several customers--a lady getting a manicure, and a couple of ladies getting pedicures in the massage chairs. They gave dolly curious looks, probably trying to figure out "What is this?" Tongues were probably wagging amid giggles when dolly left!

Dollyanne got a price list from the second shop and promised to come back when her toenails grow out, which hopefully won't take too long. The prices didn't look bad there, and they were helpful, (and those massage chairs looked sooo comfortable!) so dolly will try to use them again when her big toenails are ready!

Dolly was thinking about getting pink or peach polish, Miss D, so she could wear them to the gym (dollyanne likes to swim in the pool and use the hottub--girl's bikini bottoms of course!). They would be noticeable in her flip-flops, but might require a second look to be sure. Dolly hadn't thought about glitter. Would that work at the gym? Dolly would worry that that would be too noticeable.

Dollyanne would love to get a manicure with polish, but that would definitely cause problems at home. Dolly's spouse is always studying dolly's fingernails and pointing out when they get too long, which is often! Currently, dolly files and buffs them herself to get them shapely and shiny, but can only wear them like that a few days before having to cut them. Sigh...dolly loves the clicking of long fingernails on her keyboard and the way she has to hold them in a feminine way to keep from breaking a nail!

Dolly would love to have polish! But, dolly could only hide the polish for about a half day before having to remove it. Toenails are a different story though--dolly's spouse never sees them! So, dolly's only problem there is exposing them at the gym, or out and about in her flip-flops!

Curtsey,:manga_exclaim:
dollyanne

 

Dollyanne has a pink cb-2000 chastity on order!

Dollyanne is sooo excited, but sooo worried too! Thanks to cks pointing out the "close-out" sale on the cb-2000 (thank you, cks!), dollyanne checked it out and found a PINK one from an authorized distributor on eBay selling it for $89.95 with free shipping and free Points of Intrigue. The seller had a 100% approval rating, so excited dolly pressed the "Buy" button before thinking it through! Dolly could be in BIG trouble!



Now, dolly has a chastity device coming to her house and showing up on her charge card. Dolly will have some explaining to do! The good news is it's the holidays so packages are arriving. Dolly just has to intercept it before her spouse does! (Of course, it would be wonderful if she found it and became dolly's keyholder, but that would be like water running up hill--it can happen, but not likely.) Dolly is still working on the explanation for the charge card statement and will rack her sissy brain to think of something plausible--dolly hopes!

Dolly can't wait to try it out, but is worried too. Dolly has been practicing and adjusting to the 2" ring and feels that she is ready, but will it stay on? And, what will happen when dolly's clitty gets excited? Will she be in pain? So many members report this as a problem with the resulting lack of sleep. And, those Points of Intrigue--can dolly really wear those, or will they be too painful?

And, can dolly still rub and tweak her nipples, or will that be off limits because of the arousing effect it has on her sissy clitty? Dollyanne will find out and will certainly miss that "slut" activity if she can't do it. Dolly is hoping her sexual energy will be channeled into other more useful activities!

Dollyanne knows the cb-2000 is like a toy compared to the more serious steel belts and devices other members here have, and it will also be too bulky and not present a flat front for a sissy girl, but it's PINK, and dolly wants to try real chastity (rather than the "simulated" chastity she's been doing) to see how well it works for her. Dolly views the cb as a good "starter" device to get used to the idea, and find out how well it works for dolly, before advancing to the more advanced steel models. Because it's open, it looks easier to keep clean, and because of dolly's small length, but wider girth, a "stubby" device like the 2000 seems better. And, the best part is--the price is right, with money left over from dolly's chastity fund for sexy lingerie and other naughty sissy toys! So, if it doesn't work, it won't be a major loss for dolly. And, did dolly mention--it's PINK!!

Dollyanne knows several members here wear the cb-2000 successfully (especially Mistress Michelle's pets!) and dolly knows she can get some good advice from members like cks and eceem, who have already prepared dolly for the sanding and other preparation required for it. Thank you, both!

So, dolly is practically shaking in anticipation. The device ships on Monday so the fun should begin for dollyanne late next week. Dollyanne will be ready for sanding and fitting, for using her key safe and TimeLock program, and will report it all here!

Curtsies and Huggs,:manga_festive:
dollyanne

 

Thank You, Mistress Watchful, cks, and Missy Tanya. Dollyanne will try that glitter when she gets the chance, Mistress Watchful. Thanks for the advice!

And, thank you, cks--dolly will always remember it was you who pointed out that sale and got dolly into this fix...uh...terrific situation, she thinks.

And, Missy Tanya, thanks so much for the sweet note and encouragement! One never knows what the future may bring.

Dolly was thinking this morning (always dangerous for a bimbo like dolly!) how she feels like a young teenager again! Only, more like a young teenage girl who is anxious about the budding of her little breasts, her first date, what she should wear, and whether he will try to kiss her, and what kind of makeup looks good on her! Being a sissy girl has opened up a whole new world for dollyanne. It is like being "reborn" again and dollyanne feels sooo grateful for it!

Curtsies and Huggs,:CMrocks:
dollyanne

P.S. And yes, it is PINK!

 

Dollyanne's day

Thank You, Miss D! You have made dollyanne blush with the image of what would be going "...far past that"! Dolly has been looking at "Cosmo Girl" and "Teen Vogue" for tips!

Thanks to Your encouragement, dolly actually went out wearing her pink bra under her pink and white girl's top today! But, it was sooo cold dolly had to wear a jacket, so only dolly knew she had it on. But still, it's the first time dolly has done that and she was quite conscious of it the whole time! It definitely made her feel more girlie! Dolly wants to do it more often when she gets the chance so she will get more used to the feel of it.

Dolly did some lingerie shopping online and found this maid's outfit on Amazon:



It comes with a petticoat too! Now, dolly is trying to decide whether to order it or not. Can it be another package that might slip under the radar of her spouse because it's Christmas? Dolly is worried about pressing her luck. Still...it's awfully cute and dolly found some pretty panties to go with it too!



Dolly thinks the black with pink ruffles would look good with the maid's outfit, but the others look yummy too!

Dolly actually completed the first part of her sissy challenge today and got a pet tag! Dolly now needs to attach it to an anklet and take a picture! It's for a "small" pet, and dolly thinks it will look cute attached to her pink CB!

Curtsies and Huggs,

dollyanne

 

Well, Mistress Watchful, dolly decided to try to stay out of trouble and changed her order. Instead of ordering panties for herself, she ordered panties for her spouse--a particular brand she likes. Dolly thought that would be the better thing to do and to wait for a panty shopping reward for herself instead. Dolly did, however, order the book everyone's been talking about:



At least, dolly hopes that's the right one! Dolly's not expecting her spouse to read it, but who knows, stranger things have happened!

Dolly's mind is racing, trying to figure out what that pet tag said!

Curtsey,:manga_bath:
dollyanne