Dollyanne's Chastity Journey!

OMG, Miss D...sissy obsession time! Dollyanne has been trying to be a good gurl, but she is sooo horny! Chastity seems to change everything. Dolly milked herself like a girl this morning, just as You describe, Miss D. Dolly almost did it from nipple rubbing alone, but touched herself with one finger like a girl and had such a hair trigger, dollyanne had a "half" cummie in her pink panties in less with only a couple of rubs! Dolly was wearing a panty liner so it didn't mess up her pretty panties too much. (Dolly actually wore those same panties to the gym later!):bad-girl-0009:

At the time, dollyanne was looking at some old boi porn she wants to get rid of--sorting it out so to speak. But, what took dolly over the top? Dolly is embarrassed to say it was this real ad from a CD looking for a cuckoldress:

"Bi CD looking to be your cuckold. I will support you and your quest for black cock and your fantasies. I will watch you and your lovers and take pics or videos if you wish. I will also clean you up afterwards Long term relationship or short term its up to you. Serious only. Vicki."

There were several pictures of lipsticked Vicki reclining and looking sweet all dolled up in heels, hose, mini, garters, bra, earrings, polished nails and wig! Dolly went over the edge while staring at these pictures and imagining she was vicki!:slut:
:manga_heatwave:

dollyanne

 

Dollyanne's progress has been slow on this, Mistress Watchful, so dolly is not in a big hurry. Dollyanne thinks You should definitely assign priority to taking care of those estate matters! That sounds quite exciting! Dolly has been wondering: Does Your new role mean You won't have a dungeon in the new place?:anim_03:

Curtsey,:butterfly:
dollyanne

 

Phase II--The Ring

Phase II: The Ring

Dollyanne noticed that all the cb-xxxx devices came with a selection of clitty rings, with the largest being 2 inches in diameter. So, the question was: Will dollyanne fit into a 2" ring? To find out, dolly replaced her pink hair scrunchy with a 2" diameter rubber ring.

The ring was larger and more rigid than the hair scrunchy so it was a good test for the chastity device. The result was that dollyanne learned how to put the ring on, learned that she could indeed fit into a 2" ring, and that it was quite close to the correct size. She realized that a slightly smaller ring would probably be more ideal to help prevent tessie slippage.

During this time dollyanne also tried fitting into a 1.5" ring, but had major difficulty. The ring was really only able to fit around dolly's tessies, maybe making a good "stretching" device.

So, from all this, dolly reasoned she would need a ring that was somewhere between 1.5 and 2 inches, probably around 1.8".

Dollyanne feels this was a good thing to do, to narrow in on the ring size and build her confidence that she could indeed fit into a chastity device with a 2" ring. It also continued to train dolly for wearing something around her tessies as well as continuing to toughen up the skin with her tessies exposed. This is a step dolly can recommend!

:manga_bath:

dollyanne

 

Sissy obsession continued!

This morning dollyanne continued her sissy obsession per Miss D's directions! When dollyanne awoke, she didn't feel especially horny at first. But then, thoughts of sissy obsession mingled with thoughts of cuckolding made dollyanne's clitty engorge in her panties! (Cuckolding seems to be on dollyanne's mind a lot lately and dolly has posted more stories in the fiction section with that theme.)

So, dollyanne looked at more sissy porn with a cuckolding theme. It didn't take long, maybe 2 minutes of nipple rubbing adding only a few seconds of 1-finger clitty rubbing in a clockwise motion and dollyanne trickled in her panties. It felt more like an all over body cum than just localized to dolly's clitty. It was a warm feeling that made dolly's leg and tummy muscles twitch and flutter!

This was the picture and thought that put dollyanne over the edge:

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Could this be dollyanne in her pink chastity watching her wife cuckold her?:yes1:

Dollyanne sat at her computer this morning with the feeling of warm sissy cum in her panties. What a :slut: dollyanne is becoming! What will happen when dollyanne's chastity goes back on? Dolly feels guilty about it, but thinks she'd better enjoy this decadent sissy gurl lust while she can! It is definitely teaching dolly how to cum more like a gurl!

Curtsies and Huggs,enisdance:
dollyanne

 

LOL @ Mistress Watchful! Sorry, Mistress Watchful, dollyanne will try to post more modest pictures (like the one below!). But, dolly was certainly turned on by the cuckolding one! Dolly likes Your idea of a bondage playroom and is turned on by that too!:gen085:

And, a special thanks to You also, Miss D! Dollyanne's obsession with cuckolding (and the sissification that springs from it) is definitely growing. Dolly even visited several cuckolding sites she hasn't been to in a long time and is getting more and more turned on by it. Dolly feels she is a natural born sissy cuckold! Thank You for approving dollyanne's sissy obsession time!:yes1:

BTW, dolly forgot to attribute the picture above. It came from the Sissy and Chastity forum of CuckoldPlace and is of sissy cuckold Teresa and her wife Dee cavorting with her lover, Rich. They are apparently a real couple and have some great pics there! Dolly hadn't looked at them in a while, so when she did she got turned on all over again!

While dollyanne was surfing she came across something called "Presets", which are a series of picture slides accompanied by audio for the purpose of training and hypnotizing. Several of these are oriented toward sissy training so dollyanne has been watching them--especially the sissification ones--and they are making dollyanne horny. Dolly hopes to be able to make her own custom "Preset" for her training as well.

Dolly has been craving to get back into her chastity and expects to reach a saturation point for sissy obsession! Anyway, dolly's latest sissy obsession resulted in a little sissy cummie in her hot pink bikini panties while fantasizing about this picture from a preset called "Fem maker":



Dolly has never been in this position, :smilies_xxx06:but just the fantasy of it took her over the edge! Somehow, sissification, chastity, cuckolding, and the idea of being a sex toy all go together! It just needs to be a pink chastity like dollyannes!

Curtsies and Huggs,:manga_bath:
dollyanne

 

Wow...thank You, Miss D! Yes, these are slutty pictures and dollyanne will be sure to save them. Perhaps dolly can incorporate them in a slideshow for training herself, along with a suitable femming audio. Viewing them will remind dolly of her sissy obsession and will no doubt cause her little sissy clitty to leak profusely! enisdance: Dolly just needs another 20 or so pictures like these!

Curtsey,:manga_bath:
dollyanne (pantysexual :slut

 

Dollyanne has been aching to get back into her chastity, and expects to soon. Meanwhile, she has been wearing her chastity panties. Here she is with chastity panties under a tight stretchy mini:



Dollyanne's sissy obsession continues as she rubs her nipples and trickles cummy juice into her panties. Dolly watched "Fem Maker", a hypnotic sequence of slutty sissy pictures one after another that brought her sissy clitty to the peak and over the edge.

Dolly, the sissy :slut:, sat with sticky cum in her panties for at least 30 minutes!

Curtsies and Huggs,:manga_bath:
dollyanne

 

Thank you, lauren! Dollyanne misses you too! Dolly doesn't know how much longer she will be able to take pics. She is in a little bit of a "hot water" situation right now. Dolly could end up wilting on the vine rather than blossoming into a gurlie flower!

Huggs,:manga_bath:
dollyanne

 

Thanks for your concern, respectful. Dollyanne is trying not to panic, but if you knew dollyanne, you would know that's not possible! Dolly is a first-class panicker! As dolly mentioned to lauren, she is trying to extricate herself from a "hot water" situation she got herself into. Dolly's very sissy lifestyle may be in serious jeopardy! Stay tuned.

Huggs,:butterfly:
dollyanne

 

Thank You, Miss D! That's a perfect image of dollyanne, though it would make dollyanne's cheeks turn an embarrassing bright red. Dolly has had the experience of swishing past construction workers carrying a purse and wearing short shorts. She got lots of stares, but no cat calls that she could hear. Maybe because she wasn't wearing heels and a bra. But dolly's pace definitely quickened as she became self-conscious!

Dollyanne desperately needs heels, but because of the situation she is in right now, that may not happen. Hopefully, dollyanne can get back into her chastity soon and her life can return to being a "normal" slutty sissy gurl!

Curtsey,:manga_balloon:
dollyanne

 

Thank You, Mistress Watchful, for Your concern! (And thank you too, respectful!) Dollyanne does not plan to disappear at the moment, but it looks like dolly will have to become a "stealth" sissy, no longer prancing about the house in her pink miniskirt. Dollyanne's spouse has suddenly decided that she wants to be the girl who wears pink and wants dollyanne to "shape up" and stop shopping in the woman's section. She is like a conventional vanilla bean straight-laced person, while dollyanne is like an unconventional wobbly grapefruit. :anim_03:

She also wants dollyanne to grow her body hair back. This is a disaster for a sissy! Whoever heard of a hairy sissy!

So, dollyanne is very sad at this turn of events and has been pouting.:sad0002: Dollyanne does not want to upset her spouse, so she is trying to figure out how to comply with the demands while still following her natural submissive femme sissy gurl path. This may prove to be very difficult. Any suggestions from others in a similar situation would be welcomed.

Meanwhile, dollyanne has been longing for her pink chastity. So, this evening, dolly took a bubble bath and re-attached it. It has been a few weeks so it is VERY tight! Dollyanne had a difficult time putting it on and it is squeezing her now as she types this. Dolly plans to wear it at night until she is re-adjusted to it and things stretch back to accommodate it so she can wear it more often. (The chastity can be stealth because dolly sleeps in her own bedroom at night, and can wear it easily under her boy clothes during the day.)

Dollyanne also had a medical scare, but it appears at this point that everything is all right. Still, there will some more tests in a few weeks for dollyanne to worry about!:anim_48:

Dolly will report more on her situation in the coming days as she tries to navigate the "stealth" sissy path. Will she have to "purge"? Will she have to move out? Will "she" have to become a "he"? Anything could happen. Stay tuned. Any suggestions or thoughts anyone has for dollyanne's plight are welcome!

Curtsies and Huggs,:manga_bath:
dollyanne