Dollyanne's Chastity Journey!

Meeting Mistress WatchfulPart I (True Story)

Meeting Mistress WatchfulPart I (True Story)

Two messages suddenly came across dollyannes timeline on Twitter:

MsWatchfulsPet
@dollyanne MsWatchful wanted to tell you she is going shopping at a big JoAnns store today

MsWatchfulsPet
@dollyanne she wondered if that was anywhere near you, tweet me if you can

OMG! Dollyanne had been checking Twitter and PMs at Chastity Mansion several times a day all week and there was nothing. Dollyanne assumed Mistress Watchful had come and gone. Now this, from MsWatchfulsPet. And dollyannes real Twitter address is @sissydollyanne. Someone named @dollyanne is going to get a strange message to meet a Mistress Watchful! And, Shes still here at some store called Joanns. Is that JoAnns Fabrics? Google it quick. Only two stores found and none at the Collin Creek Shopping Center. Maybe theres one in the center? No, not found. Searching too fast. Dolly sent a message to MsWatchfulsPet on how to send Direct Messages (DM) so we wouldnt be talking on the public timeline. More messages:

MsWatchfulsPet
hey is this how to do it?

MsWatchfulsPet
Hey, she is there now i believe! Can you get there?

MsWatchfulsPet
I will call her now and ask, wait there. She is desperate to meet you

MsWatchfulsPet
collin creek shopping center

MsWatchfulsPet
Go onto the mansion so i can chat in instant messenger there, its quicker!

OMG, could dolly really go? Was she really going to meet Mistress Watchful? Her spouse was still at home. Dollys heart was pounding. She wanted to meet Mistress Watchful. What story could she make up? Off to Chastity Mansion to Instant Messenger. Then, how to use Instant Messenger. Dolly was flustered and confused by it! Calm down. MsWatchfulsPet told dolly in a CM message to Accept the chat request that has come up on your screen in a pop up box. Dolly did and it worked. Amazing.

Then dollys spouse came in while dolly was chatting on IM. She announced that she was going to go out to shop! Wow, dolly didnt need to make up a storyshe could go. On IM we discussed how far away, where She might be, description of the car. It was like a spy mission! Could dolly go? Yes, dolly could go. It would take 30-40 minutes depending on traffic. Try to get better directions.

Then dollys spouse came in again! Dolly said she was going out too. Oh good, dollys spouse said, we can go out at the same time.

Oh no, make up an excuse. Dollys heart still racing, probably sweating now. No, you go ahead. Ill leave in a minute. Dollys spouse looks at her funny, Youre acting strange.

Finally, dollys spouse leaves, shaking her head. Dolly runs around in a dither. What to wear? Thought of T.S. Eliot "There will be time to prepare a face to meet the faces that you meet." No, there isn't, Mr. Eliot. Dolly was in her cute white panties with pink trim and wearing her pink chastity. Her toenails were painted. Would this be a vanilla or kinky meeting. Vanillahas to be. MsWatchfulsPet said She likes coffee and to take Her to Starbucks. OK. Cant wear boi pants, so dolly put on her velvet lounger slacks with pink stripes. No pockets. Dolly grabbed her black purse. Should she wear her pink jacket? This could be in a public place. Dolly used to work in the area. People could recognize dollyanne. Might be hard to explain a pink jacket and a strange woman. No, leave pink jacket at home. Keep boi shirt on.

Dolly rushed out of the house and started the carhands trembling. As she drove out of her area her mind was reeling with questions. How should dolly act with Mistress Watchful? Should she talk in 3rd person likes she writes on the site? Will Mistress Watchful like her? Will She think dolly is too fat, too old, too ugly, too un-dollyanne-like? Should she have brought the pink jacket after all?

Then dollyanne had a sinking feeling. She realized she didnt know exactly where to go. Its a big shopping center. Many entrances. Is JoAnns in the center or adjacent to it? Will Mistress Watchful be by one of the entrances? It might be like finding a needle in a haystack. Dolly panickedbegan sweatingnearly ran two red lights in haste.

Would Mistress Watchful still be there? Could dollyanne find Her? Is this impossible?

(to be continued)


dollyanne

 

Meeting Mistress Watchful--Part 2 (True Story!)

Dollyanne drove in a trance toward the shopping center where Mistress Watchful was waiting. Paranoid thoughts entered dolly’s mind. Is this the right thing to do? Will dollyanne get into trouble? Dolly had never met anyone in person from the Internet before. This would be a first. She began to have doubts. She tried to focus on obeying the lights and speed limit. Mustn’t get pulled over now!

When dolly got there the shopping center wasn’t where dolly thought! Surely, they didn’t move it! Dolly had to drive around a bit too finally locate it. What kind of car was She driving again? Was it white, silver, or maybe gold? It seemed like gold was mentioned. OMG, which entrance? Dolly’s mind was going. Dolly drove totally around the shopping center slowly passing every entrance—there must’ve been at least seven of them! There were too many cars. This couldn’t be where She was! Dolly wasted at least ten minutes circling the shopping center. Then, it occurred to her, there must be a JoAnns nearby or adjacent. Dolly was looking in the wrong place! Would Mistress Watchful still be there after all this? Dolly drove around the edge again, this time looking for JoAnns. Finally, she saw it as she went past. This had to be it! Dolly turned around and went back to it and went to the entrance. No sign of Mistress Watchful. Had She left? Then dolly saw a car sitting alone near the edge of the parking lot. Could this be Her? The color and model seemed close. Dolly drove up to it and recognized Mistress Watchful immediately from Her picture and She gave a little wave, while fiddling with Her phone. (Dolly surmises She was probably calling Her pet to let him know dollyanne had arrived!)

Dolly pulled alongside with the driver doors adjacent—in the two cops position—hoping no one was watching--waved back, then got out, her heart pounding. A fresh-faced and smiling Mistress Watchful also got out and the first thing we did was hug! It seemed sooo natural to do. She exclaimed how tall dollyanne was, and dolly doesn’t remember what her reply was, but was thinking She was pretty tall Herself. Later dolly thought she should have said something like, “Dollyanne takes a short picture.” But, the truth is, dollyanne was pretty much speechless and was struck by how much Mistress Watchful looked like Herself and how Her accent wasn’t as thick as dolly was expecting, but it was rather nice.

Charlotte had suggested taking Her for a coffee, so dollyanne nervously blurted out something like, “Would You like to go get a coffee?” Dolly knew, or thought she knew of a Starbucks nearby. She said, “Yes,” immediately, so dollyanne said she would be willing to drive. She seemed to think about it for a couple of seconds, then said, “OK.”

Dollyanne was not talking in 3rd person like dollyanne does online, because she thought it would prove too cumbersome in a public place to keep it up, and besides, why not show Her the real “me”, the real “I”, even though it might shatter the illusion that is dollyanne? Dollyanne decided to just be herself. So, that is what dollyanne did. Like the country song says, “I’m so much cooler online!”

This is where dollyanne confesses that her manners went awry. Dolly told Her to “Hop in, and we’ll go over to Starbucks.” Dollyanne didn’t refer to Her as “Mistress”, and didn’t even go around and open the door for Her! For this, dollyanne apologizes to Mistress Watchful. Dolly was sooo addled! If She ever comes here again, dollyanne must correct this, especially if dollyanne chauffeurs Her and pet around! In retrospect, dollyanne believes she needs more training on how to treat a Mistress in real life. All of dollyanne’s training has been online, and dollyanne feels clueless on how to properly treat a real Mistress!

Mistress Watchful called Her pet to let him know that She was with dollyanne and that She didn’t think dollyanne was an axe murderer! When She hung up She turned to dolly and joked that She had left Her axe in the car! Even though that was funny, it was also very clear from the exchange that there was a lot of love between Her and Her pet and pet was doing everything he could to help Her, even though he was across the pond!

Dolly drove in the direction of where she hoped there would be a Starbucks as we had idle chit chat, mostly about vanilla personal things. Dolly was trying to concentrate, because she didn’t want to miss the turn! As luck would have it, dolly was going in the right direction and saw the Starbucks across the road.

When we went in, She decided on a tall pumpkin spiced latte, so dolly ordered two of them. Dolly was still nervous and when she pulled her wallet out of her purse, money went flying! Dolly didn’t even notice it, but Mistress Watchful retrieved it and handed it to dollyanne. Dolly thought She was offering to pay, and turned it down, but then She said, “No, you dropped this.” OMG, dolly was so distracted she hadn’t even noticed this. There was money in her handbag that she used on her morning walks to the store. She probably should have been wearing the pink jacket after all!

Dollyanne managed to finally pay and we took a two person table over in the corner.

We talked while sipping our pumpkin-spiced lattes, and this is when dollyanne started noticing things about Mistress Watchful for the first time. She had very nice silvery nails with little white stars on them. Dollyanne was, of course, envious, as dollyanne’s nails had nothing! She also had a really cute little pink handbag. Dolly would love to have one like that and made a note to take a look at Sam Moons to see if she could find one. And, Her cell phone had a little beaded pink multicolor cover of some kind. Very cute!

She is obviously a full-figured well-endowed Real Woman if you’ve seen Her pictures, and She was fairly bursting out of a pretty blue top, but it was Her eyes that dollyanne noticed the most. They were grayish with maybe tints of sparkling blue or green and would open wide like saucers when She got excited! Dolly noticed this because she had just finished reading Memoirs of a Geisha where the main character, Sayuri, has captivating gray eyes capable of bedazzling men! Clearly, Mistress Watchful could do the same, and while dolly watched Her talking she also imagined Her sitting for portraiture paintings by modern Rubens or Renoir-like artists!

As She talked, dolly also noticed that in addition to being obviously bright and intelligent, Mistress Watchful was a passionate person who could really get into causes She believed in. And, it was quite clear to dolly, that She was really good with people! When She leaned in conspiringly, She made dollyanne feel like she was the only person in the room!

We talked about mostly vanilla things and a little bit about the Fall Gathering, but dolly was so mesmerized that she couldn’t possibly remember all the details. Suffice it to say, that the meeting ended all too soon and She asked to go back to Her car because She had a commitment with the people She was staying with.

On the way back She mentioned that She would like to bring Her pet with Her next time, but that he had a fear of flying. Dollyanne said she understood this quite well, as dollyanne, despite being a million-miler, also has a fear of flying. Dolly tends to calm herself down with Baileys & Cream when flying. Dollyanne hopes that She will be able to return and hopefully will be able to bring Her pet with Her. Dolly knows he would really enjoy it!

We departed with another hug at Her car and dollyanne offered to chauffeur Her around if She were to return. It would make it a lot easier for Her, as the GPS apparently wasn’t that good, and dollyanne knows some great shopping places! She said She would like that and we departed with little waves.

Dolly needed to calm down so she drove to a bookstore to do some browsing. But the truth is the titles were just a blur as dolly’s mind was still replaying the meeting with Mistress Watchful.

Afterward dolly felt like it had all been a dream. Did she really meet Mistress Watchful? And, should dolly mention it on the site? What did Mistress Watchful really think of dollyanne? Dolly wasn’t sure what to do, and didn’t want to mention our meeting without Mistress Watchful’s permission.

Dollyanne sent Her a message on Twitter saying what dolly wished she had said to Her in person:

DM @MsWatchful You are such an open honest trustworthy person, Mistress Watchful, beautiful inside & out, a real rolemodel & inspiration to dollyanne. Dolly thanks You for all Your support at the Mansion & feels sooo honored to have met You in person & hopes Your image of dollyanne wasn't shattered too much! Dolly also hopes Your flight back was safe smooth & comfortable & You (& pet too) will be able to pass this way again soon so dolly can have the honor of being Your chauffeur!

So, in a nutshell that is the true story of dollyanne’s meeting with Mistress Watchful. As it turns out, Mistress Watchful was waiting for dolly to say something on the site and blonde-bimbo dolly was hesitant to say anything without Her permission. Dollyanne apologizes, Mistress Watchful, for not understanding that and for not doing that straight away.

Curtsies and Huggs,:butterfly:
dollyanne

 

Thank You, Mistress Watchful! You are too kind. Despite the nervousness and shortness of time it was still fun. If You pass this way again, dollyanne believes it'll be even more fun!

Thanks for introducing dolly to Sam Moons. Dollyanne's going to start shopping there more often! Maybe she can find a nice handbag like Yours!

Dolly is sooo glad Your trip here was successful and You made it back OK to Your pet and family. They were no doubt overjoyed to see You again!

By the way, dolly checked with TSA and, believe it or not, they said You could carry an axe as long as You check it with Your luggage!

Curtsey,:butterfly:
dollyanne

 

Today, dollyanne was Super Sissy, :character0028: spending most of the day cooking, doing the laundry, cleaning the bathroom, and squeezing in the AMA awards show in between.

Dolly also got a start on her sissy clothes trunk and sorting things to go into it. And, dollyanne is back in her training bra! It feels good to be more feminine again and protects dolly from rubbing her nipples too much.

On the chastity front, dolly's plastic lock broke! The tiny latch part snapped cleanly off! So now it still holds the chastity together, but it CAN'T BE latched! Hmmm...will dolly be tempted? She has been getting VERY horny lately and has been leaking.

But dolly is too tired to do anything about it. It's 1am and dolly is ready for a good night's sleep!

Curtsies and Huggs,:manga_snooze:
dollyanne

P.S. Mistress Watchful, dollyanne understands those impulse purchases all too well! Leave out the sabers, swords, knives, axes, and meat cleavers to make room for the IMPORTANT things (like cookie and cream Kisses!).

 

There's not a lot to report, but dollyanne re-colored her hair and is now even MORE blonde than before!

Dolly also switched back to the Master Lock since the plastic lock broke on her chastity. Since dolly is self-locked she has the key on her key chain. Dolly is still quite horny and hasn't had a squirtie in a LONG time, and is even afraid to have one in her chastity since her "accident".

Dolly is considering a new chastity for Christmas and has narrowed it down to either the cb-6000s or the maturemetal "jailbird". The later has the edge at the moment as it is steel and maturemetal has been very good at answering dollyanne's many questions.

Happy Thanksgiving, everyone!

Curtsies & Huggs,:butterfly:
dollyanne

 

Thank You, Mistress! Your wish shall be done! Dollyanne has been talking to maturemetal and is now considering the "jailbird" from his site. It is slightly cheaper, looks quite easy to keep clean for long-term wear, and has gotten a good review.

The only dimension dolly is still unsure about is the length of the cage. It needs to be VERY short because dolly's little clitty is sooo short. Even 2", which is shorter than dolly's current cb2k, would allow dolly's clitty to have a 50% erection, so dolly was thinking of maybe 1 1/2", which gives dolly a 38% erection, or even possibly 1 1/4" (the lowest his chart goes for cage length) to give a maximum 31% erection while caged! (You can tell dolly was once an engineer in a previous life!) Dolly is thinking this will prevent her from trying to get a squirtie while in the cage and possibly injuring herself again! Plus, it seems appropriate that a sissy should have a very tiny clitty with no significant erections--even partial ones--especially while caged!

Dolly doesn't want to get the wrong length dimension, as it's hard to change once made, so dolly is doing experiments with her cb2k, such as stuffing it with cotton, to see how a shorter cage might work!



Any thoughts You or Your pet (or anyone from the site for that matter) have on this from Your experience with devices would be welcome! Dollyanne hopes You will be pleased with the choice also!

Curtsey,:butterfly:
blondie dollyanne

 

Thank you, cindy. This is definitely something to consider. Maybe dollyanne needs a course on hydrodynamics of penile expansion! Going with the larger one might mean going with a 1.75" or maybe 2" length. The cb6k, which many people seem to be happy with so far, is the same length as the cb-2k, around 2.5". This would allow a 40%-50% expansion, roughly, for the average sized penis. This would equate to 1.75"-2" for dolly's clitty size. Dolly needs to do a little more research before resolving this!

Huggs,:butterfly:
dollyanne

 

Thank you, madamsboy. Dolly has heard other people say this too, that the shorter the better, and that the growth is what is causing some people problems in their chastity. As you say, maybe that's why some people are preferring the cb-6000s, and why it is more comfortable at night. Dollyanne has noticed that once her clitty gets adjusted to the length it automatically stops and doesn't try to go any farther, unless it can expand, like through the bars of the cage or something. It is almost like it "learns" its limitations! Only when dolly tries to have a squirtie in the chastity and tries to force it past the limit does it seem to present a major problem! More food for thought!

Huggs,:butterfly:
dollyanne

 

Thank You, Miss D! Dollyanne will work on a way to do that. The color is more blonde with just a slight reddish tint in it. Dollyanne must be a red-head at heart!

Dolly is wearing her bra every chance she gets. One question dolly has is whether or not to wear her bra when sleeping. Dolly has done it both ways. Many girls don't seem to wear their bras while sleeping, but perhaps sissy gurls should! Dolly wakes up horny EVERY morning and if she doesn't have a bra on she will rub her nipples, sometimes in a delirious frenzy, until her clitty is practically bursting through it's chastity cage! But maybe this unfulfilled delirious frenzy is a good way for a sissy to start the day! Do You have any advice for dollyanne on whether to wear her bra when sleeping?

Curtsey,:butterfly:
pantysexual dollyanne

 

Not much to report, but dolly hates to see her journal pushed all the way to the next page! Cold front has moved in and dolly's freezing her tessies off!

Daily Panty Report: light pink with white lace and transparent mesh rear with little diamond-shaped pink polka-dots.

(Dolly just realized she doesn't have a picture of these panties. Must take one!)

Dolly continues wearing her bra daily. Wearing a bra is a good thing in cold weather! It prevents dolly's nipples from freezing over!

Dolly continues in her pink chastity and is trying to keep the Master lock oiled up so it doesn't rust. A decision needs to be made soon on a Christmas chastity so dolly can beat the rush!

Curtsies and Huggs,:butterfly:
dollyanne

 

Dollyanne removed her chastity and cleaned it in her bubblebath, then shaved her clitty, legs, and chest, and re-attached the chastity. For dolly, the bubblebath is like a clinical environment, so she didn't even think about hanky panky. The chastity came off and went back on very easily.

Then dolly dressed for bed: 38C bra (pink) to make her feel more feminine and to discourage her from rubbing her nipples--especially in the morning--pink tank top, white full-fashion hose with white garter, white on white extra-absorbent panties for nighttime use, and pink micro-mini! Except for the bra and absorbent panties it feels like a honeymoon outfit!

The bra and hose should help keep dollyanne warm on what is expected to be a cold night.

Curtsies and Huggs,:manga_bath:
dollyanne

 

Yes, Miss D, sooo true! Dolly was silly, but they were new and dolly couldn't wait! Now, dolly is wearing them underneath today and loves how they slide up and down her thighs as she walks!

Today's inner gurl: pink training bra, wedding white full-fashion hose and garter, pink chastity, pink panties with transparent pink mesh front and field of pink stars, pink toenails! Outer boi: dull navy lumberjack look! Lumberjack on the outside, gurlie on the inside!

Dolly will switch to her pink satin nightie, Miss D. Thank You sooo much for Your comments, Miss Dthey truly help dolly feminize!

Curtsey,:butterfly:
dollyanne

 

Full-fashion hose are a true engineering marvel and dollyanne is amazed they stayed intact all day slipping and sliding as she walked and swished along!

Dolly is out of her bath :manga_bath: and is clean and relaxed and ready to prepare for bed the way Miss D has recommended--with a silky nightgown. Dolly is wearing the pink satin night gown that is in her profile picture!

Dolly also did a little shopping and got some gray and pink striped thigh-high socks to wear in case it gets cold. The weather will be in the 30s (F) tonight.

In may seem paranoid, but dolly is afraid of totally immersing her chastity lock in the bath for very long. She puts oil on it and also oils a key and puts it inside (a trick from maturemetal), but still she worries about it. So, dolly has taken to replacing the Master Lock with the broken plastic lock during her bath. The chastity stays on the entire time--there is just a temporary lock change. Dolly is amazed at her own self-discipline in doing this (she doesn't have much self-discipline in other areas of her life). The bath (and shower too) are like a clinical environment to dollyanne. Still, she needs to find a small lock that is totally water-proof so she doesn't have to do this!

Curtsies and Huggs,:butterfly:
dollyanne

 

Daily panty report: light pink transparent mesh with black waist trim and black lace bottom trim, and the word "Perfect" embroidered in black at the left hip.

(Dolly just realized her panty album is no longer there! She will need to restore it so friends of dolly can see her panties!)

It is cold here today so dolly's inner gurl is also wearing pink/gray/blue striped thigh-high socks also for warmth, in addition to her pink training bra of course! Outside though, dolly is wearing her dull flannel "lumberjack" shirt with dull navy boi pants.

Dolly is also still in her chastity secured with the Master Lock. It is unlubricated at the moment, because dolly wants to see how short she might be able to go with a custom chastity from maturemetal. (Not being lubricated sometimes causes dolly's clitty to get "hung up" on the cage bars far short of reaching the end.)

Curtsies and Huggs,:butterfly:
dollyanne

 

Thank you, cindy, for your kind comment! Dollyanne is glad to know you are reading and getting something out of dollyanne's journal. Sometimes, maybe because dollyanne is not part of a couple, she feels like she is talking to herself in here. But one thing is for sure, and dolly feels we both agree on it, Miss D's advice on femming is GREAT!

Huggs,:butterfly:
dollyanne

 

Dolly was a slut in the kitchen today wearing her bright red mini-skirt and "Perfect" pink mesh panties with black lace while slaving over a "Mulligan Stew" dinner that took 3 hours of chopping and peeling fruits and vegetables, and then slow cooking. Dolly modified the recipe from a female hormone book and dolly's spouse loved it!

Dolly hasn't exposed her new thigh-high gurlie socks to her spouse yet as she didn't want to possibly spoil the moment. Dolly is pretty conservative when it comes to flaunting her sissiness with the spouse, but eventually she does!

Dolly has also been on the lookout for an enfemme chauffeur's outfit on sale so she can make good on her promise to chauffeur around Mistress Watchful and Her pet should they ever come this way again. If dollyanne can't find one she may have to create one out of bits and pieces.

On the chastity front, dolly is getting comfortable with the dimensions and model she has chosen, and is close to placing her order with maturemetal. There are just a couple of logistical details to work out on shipping and such. Dolly was even thinking (vainly!) that this could be a new model called, "the sissy", or perhaps (humbly!) "the dolly"! It might be something that would appeal to "small" sissies! (Just dreaming!)

Curtsies and Huggs,:butterfly:
dollyanne