Dollyanne's Chastity Journey!

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  1. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Thanks, mike! Dollyanne hopes your optimism is catching!

    Huggs,
    :butterfly:
    dollyanne
     
  2. lauren1fem
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    lauren1fem Gurl

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    Well one thing that springs to mind... and it might eventually be viewed as a benefit to your wife (that would solve two problems, yes?) I suggest that you do more around the house - and maybe you already do this, but even the most fastidious person can always do just a bit more.

    Examples: Make the house sparkle!. :chores012: Have a proper dinner all ready for Her. Do spring cleaning, clean out the garage, :character0174: get dirty. But don't make a big deal out of it, just hope that you do lots of tasks that in time She will notice.

    Inside your own mind, you'll be doing this because you're serving your Mistress as a proper sissy, but all she will see is the sparkle - at least in the beginning. You'll get the benefit of being "productive" and you will get the benefit of "secretly" serving Her. You'll be performing sissy maid service (productive) and the serving may offer some kind of slutty kink for yourself too - no reason you can't clean in your sexy attire if you're all alone and maybe your mind will drift off into a slutty fantasy when you clean out a closet or vacuum under the guest bed. You can always take a quick mental sissy-slut-break and slip off into slut delirium. :slut:

    In the end, maybe, just maybe your wife will enjoy the new productive (sissy slut) partner. In time, maybe she'll find some cruel way to punish you if you don't keep things spotless. :manga_snooze:

    In the meantime you can dole out your own fantasy punishments. Go clean a room as "maid dollyanne", then pretend to inspect said room and if "that maid dollyane" missed a spot you can spank her or make her do sissy tasks that make her feel humiliated or whatever.

    ** As I type this I'm reflecting about the fact that I've been doing this myself for many years. I've just never thought of it this way. I've done things like this in the past as enticements to get something completed. Lauren speaking sternly to self: I expect you to have all your Chemistry homework done within the hour or you will march right upstairs, lean over the edge of the bed, hike up your skirt and spank yourself 20 times for being a lazy gurl! But if you're a good gurl and get all your work done then you may secretly wear your favorite pink bra when you go to class tomorrow morning.

    I end up "winning" no matter the outcome, but it does make me focus! All the while I've frenzied myself up in the process. It's loads of fun. But you know I'm a bad girl :slut: for taking these things to such extremes.

    Anyway that's my present :gift-060: thought to you sweetie. What do you think?
     
  3. Mistress Watchful
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    Mistress Watchful Dont believe the hype ;oP

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    Oh I'm sure you haven't enjoyed thinking about that at all have you dollyanne!

    On a more serious note, I do see what you mean, but I'm sure you can be very discreet with your pink girlieness.

    I really would love to come shopping with you and lauren btw... I still say we should hit Vegas!!!
     
  4. chastityslavejohn
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    chastityslavejohn Mistress Irianna's pet

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    O/our lives have changed and Mistress and i are together almost all of the time...so i get a huge rush out of doing chores within Her eyesight. but last year when Mistress was working at Her old job i was alone all day...and very sad. to cheer up i would pretend that Mistress was watching me work and scolding me for my transgressions. maybe this would work for Dollyanne, as lauren suggested.

    Mistress Watchful, vegas is O/our 2nd favorite place and W/we own a timeshare there. (Paris is O/our favorite place!)
     
  5. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Lauren, thank you for the ideas! Dollyanne thought her spouse would like the help, so dolly did so (dressed partially en femme), but it backfired! Dollyanne tried cooking, cleaning, doing the laundry, etc., but dolly's spouse DIDN'T like it! It seems she felt that was HER domain and dollyanne was not to try to take it over. She did seem to like the cooking best, but the other things were a problem for her to accept.

    As for the pretend Mistress, dollyanne has tried something like that also with the virtual Mistress program. The program assigns tasks to dolly, which she must do, or else receive a punishment. This works similarly to what you describe. Dolly needs to work at perhaps revamping her VM program to accomodate her new circumstances. The fantasy world is probably the best one for dollyanne to pursue so far. Thanks for the ideas, lauren!

    Huggs & Kisssses,
    :manga_bath:
    dollyanne
     
  6. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Wow...what a picture--dollyanne and lauren guided through Vegas with Mistress Watchful! That will be in dollyanne's dreams tonight!

    Curtsey,
    :butterfly:
    dollyanne
     
  7. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Very nice thought, chastityslavejohn! Dollyanne needs to learn how to please her pretend Mistress better, like you describe!

    Dollyanne envies you to be able to go between Paris and Vegas!

    Huggs,
    :manga_washup:
    dollyanne
     
  8. Respectful
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    Respectful Chaste by choice

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    You are always expanding my definition of cool dollyanne.

    Hugs and respect :)
     
  9. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    In steath mode. Little dollyanne is tight and smashed in pink. Two inches of freedom! No escape possible, no cummie allowed!

    Curtsies and Huggs,
    :manga_bath:
    dollyanne
     
  10. Respectful
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    Respectful Chaste by choice

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    Awww! :manga_bunny:
     
  11. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Dollyanne had a good day in deep sissy stealth. Dolly is still chaste and is getting quite adept at cleaning her chastity with the power shower and applying neosporin and lube with Q-tips!

    Dolly was also able to take a long walk in her chastity with no ill effects, so the re-adjustment period was only about three days. Dollyanne is back in the chastity saddle again!

    Dolly's chances of having a sissy milkie in her tighter chastity appear slim. What a difference two millimeters makes! Dollyanne isn't even leaking yet, so more time is needed. Last time took nearly a month before dollyanne was able to have a sissy milkie in her chastity!

    When the going gets tough, sissy gurls go shopping! So, dollyanne found this darling babydoll with pink polka-dot panties on sale and just HAD to get it! As you can see, the wider gusset contains dolly's chastity quite discreetly!

    pink polka dot panties and nightie 2.jpg

    Curtsies and Huggs,
    :manga_bath:
    dollyanne
     
  12. sophia
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    sophia Senior Member

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    The ultimate shoppingcar for Dollyanne?

    resized.jpg
     
  13. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Thank you, sophia--that's a beauty! Dollyanne would love to doll it up with these cute seat covers:

    pink car seat covers.jpg

    Huggs and Kisssses,
    :manga_bunny:
    dollyanne
     
  14. sophia
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    sophia Senior Member

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    to be honest Dollyanne, if I exposed my Wife to all that pinkness I think she would kill me! You are a very brave gurl. Be careful!

    Don't you think that ugly black stearing wheel in your car need a more pinkish tone. It kind of destroy the nice pink attitude?

    Sophia
     
  15. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Dollyanne didn't want to take off her pink chastity, so she went to the gym today wearing it, and swam laps in the pool! :character0180: It was quite an experience--dollyanne with her pink and white towel, pink flip-flops, pink lock, pink panties, and pink chastity! Dolly wore her black girl's swim bottoms along with her pink panties to keep the chastity in place and hidden. Dolly had a second pair of purple panties in her gym back to wear afterward. Dolly swam, got in the hot tub, showered, stepped briefly into the sauna (with her pink towel around her), and got dressed. That was the hardest part--slipping on her panties under the towel to hide the chastity!

    Dolly suspects the chlorinated water is not good for the plastic chastity, spacers, and joints. And, the hot tub is probably full of bacteria trying to get under the rings. So, when dolly got home she took a quick bubble bath to clean away any remaining chlorine residue. If dolly finds herself swimming often she may want to consider the impact of this. Has anyone else experienced a problem with swimming in a chastity device with respect to wear and tear or otherwise--especially a plastic one like the cb-xxxx series?

    Curtsies and Huggs,
    :manga_bath:
    dollyanne
     
  16. dar
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    dar Sub

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    Dollyanne:

    You certainly are a daring and darling gurl ;)

    --dar, who will try the Lori tube again soon
     
  17. lauren1fem
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    lauren1fem Gurl

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    Dolly dear, you are being a very brave gurl at the gym - and in Texas to boot! I should think someone might banish you from the boy's locker room with all that pink gear in tow. Since there is no "gurl" locker room you may find yourself in dire straits...

    Tread carefully in public, sweetie! We would all feel terrible if something was to happen to you - even a raised eyebrow can be devastating to a vulnerable sissy. Hold your head high dear, but please be circumspect. :manga_lolly:
     
  18. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Dollyanne goes to the gym in her chastity again!

    Dollyanne just doesn't want to remove her chastity so back to the gym to swim went dollyanne again! This time dollyanne found a nice pair of lavender goggles to use (no pink ones were available!). It was a little more crowded this time, so dollyanne had to use her best stealth techniques to hide her chastity. Dolly wore her purple panties underneath her girl's swimsuit, so it helped to hide the device, though if anyone looked closely they could've seen the familiar chastity bulge.

    It feels different to swim in a chastity device--the clitty feels like it's cool and floating!

    After the swim and hot tub, dolly showered and dressed in her pink panties! Just another day for a sissy gurl at the gym!

    Curtsies and Huggs,
    :manga_bath:
    dollyanne
     
  19. lauren1fem
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    lauren1fem Gurl

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    I tend to agree with Dar... Lauren's boy-half is a bit confused by all of dollyanne's visits to the gym in her suggestive clothing. I have to say that I've been hit-on by guys more times at the gym than anywhere else - and it's always very disturbing for me 'cause I'm not that way (though a bit flattering). Lauren/boy-half doesn't go to the gym to meet anyone. But what can I say - gay guys find my slender form attractive and who can blame them? Lauren is a hot :jumping0039: little number even if she's a he on the outside... (LOL) [Okay so Lauren is a boastful bitch today]. (I'll warn you that I'm listening to the Velvet Underground/Lou Reed right now. Those songs paint such a nice raw picture for me - perhaps tainting my view of this situation.)

    Methinks dolly is taking trips to the gym to get outted. In all her pinkish gurly garb is she hoping for a chance encounter? Is she thinking she'll find a cucky man to bring home? Poor dear is taking chances in order to find her place. She'll be all locked up and won't be able to get off, but she sure could blow "the right man" if he came along, no? That was a New Year's Resolution for our sweet dolly.

    Pink panties - what a tease! She's a naughty chaste sissy that wants some slutty action. If she isn't careful she may get more than she bargained for. :confused0086: Even if there's no action for dolly I bet she comes back from the gym all worked up and steamy just from flaunting her gurly self in front of her potential targets. Does dolly swish, saunter and mince her way to the steam :chores036: room if no one's watching?

    What say you dolly? Are you the slutty gurl I'm making you out to be? Is this one reason for the visits to the gym in your sexy attire?
     
  20. Respectful
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    Respectful Chaste by choice

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    Confused

    Hi Dollyanne;

    Having read Lauren's eloquent analysis I think I agree with everything she said, including her (and his) self boasts for illustrative purposes :)

    What do you think dollyanne?
     
  21. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Thank you, lauren and respectful! (And, thank you too, dar, for your compliment!). So, hottie lauren gets hit on a lot at the gym?! Hmmm...maybe lauren is sending off sissy gurl signals like phermones attracting predatory males! Dollyanne is not as luscious as lauren so dolly is not hit on as much--in fact, not at all for some time.

    In boi mode dollyanne doesn't have a gay bone in her body--it doesn't even cross her mind. But in sissy gurl mode, dolly's whole mindset changes. She envies the girls--their long hair, smooth legs, and figures--and lusts like a slut after the boys--the big muscular masculine types (who, dolly knows, might turn out to be gay!). The latter, not so much to have sex with, but to give pleasure to, as dollyanne, the sissy gurl.:slut:

    Dolly knows that most gay guys dislike cross-dressers--they ruin their reputation! So, in dollyanne mode, dolly fantasizes about non-gay masculine men who lust after the fantasy of a sissy gurl like dollyanne.

    So, what you say may in fact be the case, lauren, and respectful. Perhaps dollyanne is escalating her pink sissiness at the gym to guarantee that she will eventually be outed. Maybe dollyanne is really looking for a boyfriend to be a sissy gurl slut with!:bj:

    Dolly has imagined how she might respond if someone catches her, for example, with her pink chastity. She has a story ready. She goes into the sauna with her pink and white towel. Three men are there. One laughs and rips dollyanne's towel away. "Whoa, what's that," he says, looking at the pink chastity. "A chastity," dollyanne says, trying to get her towel back. "Whadda you need that for?" another man says. "Doctor's orders," dollyanne says. "To prevent orgasm before having a PSA test." The men snicker and one says, "Never heard of such a thing." "Me neither," another says. "Your doc didn't say WE couldn't have an orgasm, did he?" the third one says. Dollyanne looks down, "No." The men look at each other. "Your body is shaved," one says. "Yeah, you look a little girly," says another. "All pink." Dollyanne blushes. "You want your towel back, then down on your knees girly." "Yeah," another chimes in, "Nothing says you can't give us orgasms!"

    So yes, dollyanne does get worked up at the gym, and whether she is in reality or in her fantasy, she is definitely a sissy gurl slut in the men's locker room! She wonders what she would do if someone said, "Get on your knees now, sissy gurl!":smilies_xxx10:

    Dolly is basically shy, but can get herself into risky situations. Perhaps dollyanne should tone things down a bit and go slower. Dolly is ready to paint her toenails, wear a pink cap (along with the other pink things), don sexier gurly panties with lace and frills, and a more obviously gurly swimsuit--maybe something with pink polka-dots! Any one of these things is a thrill on its own, but put them all together and they could spell trouble for dollyanne!

    So, thanks for your concern, lauren, dar, and respectful. Dollyanne will take things slower and get her thrills in small, hopefully safe, increments!

    Huggs and Kisssses,
    :slut:
    dollyanne
     
  22. PuppyMastersPet
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    I must be the exception to the rule lol. I think what you said is true to a certain degree though and its a shame. I have one rule, as Im from a minority group myself I cant allow myself to discriminate against any other minority group that would make me a hypocrite.

    When Ive been out to gay clubs and I even went out dresses once you even found other trans groups discriminating against each other. When I went out dresses once I could see the more flamboyant transvestites looking at me with a disapproving look. It seems such a shame.

    Looks like I decided to catch up on your diary at the right moment. I havent had a chance to read many diaries for quite some time.
     
  23. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Dollyanne woke up this morning in her new nightie, a little disheveled, but feeling good!

    Waking up with her chastity poking a tent her new panties:
    nightie black pink 7.jpg

    Rubbing her nipples, beginning to squirm and moan with her chastity playing peek-a-boo:

    Until her little clitty was straining against the bars of her chastity cage!

    Though dollyanne didn't achieve a sissy milkie in her chastity, this little sissy gurl morning exercise made her feel good all day! As good as sex! Well, maybe not quite THAT good, but sissy sex anyway, and it definitely got her adrenaline pumping!

    So, later, dollyanne decided to go to the gym and swim again in her chastity. This is dolly's toned-down sissy gurl swim kit:

    swim kit 4.jpg

    It consists of: a pink and white modesty towel, pink lock for dollyanne's locker, pink flip-flops for the pool and shower, lavender swim goggles for laps, pink cap to keep dolly's hair covered, pink stretch (Victoria's Secret) panties for afterward, and girl's black swim suit bottoms!

    The pool and locker room weren't very crowded so dollyanne had no problem getting dressed and undressed with her chastity on this time! Dollyanne is getting this down!

    Dollyanne is getting close to being able to paint her toe nails pink! This is exciting to dolly and she can't wait to do it!

    Curtsies, Huggs, and Kissses,
    :manga_bath:
    dollyanne
     
  24. dollyanne
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    dollyanne Sissy who loves pink frilly things!

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    Dollyanne's lock obsession

    Dollyanne found a new lock! This one is called, "Wordlock" and has over 10,000 combinations of four-letter words! And, it's available in pink!

    wordlock pink 1.jpg wordlock pink 2.jpg

    Hmmm...anyone have any ideas for some good four-letter words for dollyanne to set this to for use on her gym locker?

    Curtsies and Huggs,
    :manga_bath:
    dollyanne
     
  25. unruffled
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    unruffled Zen Master

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    It's human nature to have an "in-group" and an "out-group". It's how we've evolved. Better educated people tend to overcome this part of our nature, but not always.

    Evolutionary psychology is a wonderfull and fascinating subject.

    -- Unruffled.
     
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