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Sissy Shopping and Sucking with Mistress (part 2 of Chastity Locks, Adam and His Cock, and Sissy Smocks)

Hello, Horny Readers! As promised, I’m back to recount the second part of My Summer-so-far highlights. This episode concerns a sissy shopping trip in search of the perfect dress for Jamie. You remember Jamie, don’t you? S/he’s the sissy I invited over for some face-sitting last Summer, just as I was coming out of a period of illness. The plan was that W/e would have a girly spa and shopping day, and then finish the evening putting O/ur grooming and shopping fun on display for Adam.Miss Rachel loves to take sissy shopping! 1-800-356-6169

This was the first time Jamie had gone somewhere other than straight to Our house during the day and girl-dressed, so it was a momentous occasion. A new dress, and some sexy time with Adam and I at the end of it all, was the incentive to get he/r to step out of he/r comfort zone.

Now, while Mikey is one of Adam’s favorite fucks (refresh your memory as to why in part 1), Jamie is one of His favorite cocksuckers. As you recall, I found out last Summer that s/he’s surprisingly good at pussy worship, but I’ve always known that s/he was particularly good among Our slaves at cock worship. S/he loves to fuck as well, but can’t take it quite as hard or for quite as long as Mikey can.

Miss Rachel loves to take sissy shopping! 1-800-356-6169Jamie could endure a rough throat fucking all day, however, and be looking around for another one at the end of it all. I like to joke with he/r that s/he’s got a clitty down he/r esophagus as well as between he/r legs.  So as you can imagine, the prospect of cock worship while wearing a gift gleaned from a Mistress and sissy shopping and spa day was an effective carrot and stick, he/r obedient nature notwithstanding.

W/e dress simply for sissy shopping and spa day!

We began O/ur girls day out at Juut, a division of Aveda. If there are any in your area, I recommend that you give them a try! They are welcoming toward the non-binary (at least in O/ur area), and both their products and level of service are delicious!

When W/e’re having a Summer day out, both My sissy and I will dress simply in a little sundress and thong sandals. This Winter, I’d instructed Jamie to start growing he/r hair, because it really is beautiful–dark brown, thick and shiny–and if a gurl can get away with it, I really prefer s/he be able to style he/r natural hair. Jamie works from home, so luckily, s/he could easily get away with it, and by O/ur sissy shopping and spa day, it was long enough to be pulled up into a small ponytail at the nape of he/r neck. S/he looked adorable, and he/r cheeks had a natural glow of sissy humiliation and delight as W/e walked from My car to the salon.

W/e were greeted by the staff with bemused friendliness when W/e entered. Other patrons reacted much the same, and perhaps with more than a little curiosity. Maybe some uptight blue-hair was scowling somewhere, but W/e were tingling with so much endorphin that all W/e saw were the smiles as W/e were ushered to O/ur first stations.

W/e both got a full body massage, waxing services, and mani-pedis. O/ur hairMiss Rachel loves to take sissy shopping! 1-800-356-6169 was washed, deep-conditioned, and trimmed. Jamie had he/rs styled as well, and the finished product was the most adorable pixie-bob you ever did see! When s/he was turned toward the mirror to see the results, I dare say that pleasure contributed to the color of sensual humiliation in he/r cheeks.

W/e didn’t get our makeup done, as W/e knew W/e’d want to do that closer playtime, so after pampering, it was time for shopping!

Jamie the Sissy Shopping for the perfect flirty dress!

What makes sissy shopping for a dress different than that of any other femme? Well, it’s not necessarily different in general. It depends on the sissy he/rself, and the purpose the dress will serve: casual wear, a formal event, embracing a professional image as part of a sissy secretary or assistant role, or as in Jamie’s case, to look like a sexy little tart who’s about to get a throat-full.

Mistress loves to take sissy shopping! 1-800-356-6169I suggested something short, to show off he/r gorgeous long legs, now silky smooth from the wax job. W/e’d already selected a spindly little pair of silver mules from h/er wardrobe to show off he/r freshly-painted bright red toenails.

W/e headed off to Nordstrom’s for their wide selection, sure that W/e would find something that fit the bill in Jamie’s usual size 12 Women’s. It was a weekend day, and busy, but surprisingly most people seemed preoccupied with their own shopping and didn’t pay much attention to U/s.  Jamie cuts a femme figure, even at a bit over 5’10 and muscular in a wiry sort of way. Especially with he/r new haircut and graceful walk. Maybe even without makeup and falsies, s/he passed.

It took U/s a good hour of sifting through racks and trying things on to find the perfect dress–a silver metallic satin-esqe spaghetti strap number with an open back and a hem that hit right below he/r pert little ass. I spotted a little red silky thong that I insisted s/he get as well.

Jamie softly objected to the dress at first, at how short it was. I was beginning toMistress loves to take sissy shopping! 1-800-356-6169 think W/e might be able to skip rouge when W/e finally got around to making up O/ur faces because in this as in every stage of O/ur excursion, the color in he/r cheeks deepened.  Just the same, I know Jamie well enough to realize that he/r objection wasn’t sincere. S/he was just feeling shy, and needed some encouragement from Mistress.

“Jamie,” I whispered in he/r ear “You are going to look like such a shameless little emasculated cock-hungry tart in that dress that Adam might fuck your mouth pussy twice out of sheer arousal.”

Of course that convinced he/r, and a smile curled the corners of he/r mouth. S/he lowered he/r face, tickled pink up to he/r gleaming blue eyes, and folded the selection over he/r arm.

I induced he/r to give he/rself away a little bit at checkout, requiring he/r to speak to the clerk. Jamie’s boy voice is a deep baritone, and sissy voice training doesn’t mitigate that much. The clerk was surprised, but as fate decreed for O/ur whole day, not disapproving. S/he even called he/r “Miss” during their interaction, though not without a teasing look, and I thought Jamie might faint from pleasure and embarrassment.

S/he attempted to make a b-line for the exit when W/e left Nordstrom’s, but I insisted W/e stop at Sephora. “Mistress,” s/he whispered, “I have plenty of makeup packed.”

“I know, Jamie, but I want to get you something special. An extra little treat.”

Mistress Rachel loves to take sissy shopping! 1-800-356-6169I scanned the displays as Jamie hung back, he/r shoulders creeping up toward he/r ears. A clerk approached to ask if I needed help finding anything, and I made sure to speak loudly and clearly when I asked if they carried their lip plumper at this location. She found it for Me quickly, and after I paid, s/he pulled out a bag. “No thank you,” I said. “S/he can put it in the bag s/he’s already got,” and handed it to Jamie.

S/he couldn’t get out of the store, or the mall, fast enough. “Mistress . . .” s/he whined plaintively. But it didn’t escape Me that s/he’d lowered the shopping bag to he/r waist to hide the tent in he/r sundress.

Sissy shopping and spa day complete, and now stud cream for dessert!

When W/e arrived at My place, Adam was at the gym. He’d shower there, and pumped with testosterone from pumping iron, would arrive ready to have His balls drained. I texted Him to tell Him there was a cum-thirsty sissy slut waiting for Him. He texted back a photo of His full balls, with a message that He intended to fill up he/r stomach and mess up he/r pretty makeup.

I showed it to Jamie.

Immediately clutching he/rself and dancing from foot to foot like a kindergartner who needs to Miss Rachel loves to take sissy shopping! 1-800-356-6169use the potty, s/he begged to be allowed to masturbate in the shower. I told he/r no, of course, because the desperation s/he felt would contribute to he/r giving better head. S/he knew this, but decorum and the sissy cocksucker libido are often at odds. I showered with he/r to make sure s/he behaved, yes, but also to revisit the surprising talent I’d discovered in he/r last Summer. *wink*

Soon, W/e were primped, blow-dried, moisturized, cooled, fed a light snack, made-up, dressed, and waiting. I selected something in body-hugging black lace, and a black thong to match. Jamie’s eye make up was smokey blues and silvers, with plenty of black eyeliner and mascara. She wore he/r lip plumper in copious amounts, accenting he/r DSL’s with bright red lipstick. Applying it kept he/r mind off of he/r arousal, and soon enough My phone pinged with the text that Adam was on His way in.

I suppose you want to know what happened next?

Well you’ll have to listen in for that.

Miss Rachel loves to take sissy shopping! 1-800-356-6169

Click here to listen to what happened next!

xoxo

Miss Rachel, your sissy shopping guide!

1-800-356-6169

 

 

 

11 comments to Sissy Shopping and Sucking with Mistress (part 2 of Chastity Locks, Adam and His Cock, and Sissy Smocks)

  • Pupslave

    I’m pretty sure I’ve had some dreams like this, Goddess. Only, they tended to have more chains, a collar with a jingling bell, and the word “whore” written in lipstick across my face.

  • princess

    That was sooooooo Worth the wait!! I Loved the sissy shopping trip and trip to the salon. I’m not sure i could perform as well as your sissy slave but…. What i wouldn’t give to be on my knees pulling Adam’s monster past its zipper! There is just something magical about holding a thick long cook like his in my hands and eagerly bringing it to my lips!….Thanks for such a HOT post….and that photo of you is to die for!

    • Rachel

      I have endless faith in you, princess, so I bet you could give Jamie a run for he/r money in the cocksucking department with the right training! *giggle* 90% of any endeavor is attitude, and you’ve got the right attitude to be the best little cockwhore going!

      And glad you like the photo! I haven’t shared it before because, well, even Mistresses sometimes have insecurities, and I think My ass looks too big in that photo. But I decided to embrace My fat butt! lol

  • Wow, that sounds like such an exciting day. I’ve done the mani pedi but never the full girly day of beauty and shopping but would absolutely love to. Topping it all off with Cock sucking sounds like the best day ever. ☺️

  • violet

    Wow ty so much for this hot blog Mistress, and i must agree the photo is amazing, i love your butt also looks perfect to me !!!

  • Gem Sissy

    What a great blog! I’d love to be taken on a day like that, leaving my restrictions behind to go full girly!

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