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.

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.

Jamie 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 hair 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.

I 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 to 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.”

I 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 use 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.

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Goddess Rachel loves sissy shopping and cocksucking! 1-800-356-6169


Miss Rachel, your sissy shopping guide!