Sophie's Girlie Day - Part 1: Shopping for My Office Outfit with a Note from Mistress

Those of you who took part in my World Cup Chastity Game know that I asked players to submit ideas for a Special Reward that they would receive if their team won the Cup. This was the time to ask for something other than the spanking, chastity, edging, etc. that was already part of the game, and my own subs were allowed to submit items for which they would not normally ask me. A reward would be individually designed for each winner based on the ideas that they submitted. In other words, it was a golden opportunity to fulfill a fantasy under my supervision. 

Only sophie earned this reward. One of her ideas was to:

Go and buy a girl's outfit, such as a secretary or school girl's uniform. Tell the sales girls I lost a bet with some female friends and I have to dress up for them in this kind of outfit, and ask if they could they help me choose. Perhaps Mistress could write a letter out as though I'd lost the bet with her and include ideas of the kind of things she wants me to wear, so I can hand it to the girls and it looks like I have been sent.

sophie had another leg waxing at the girlie-named salon scheduled for her upcoming day off in a week and a half or so, so we decided that she would wait and make a day of it. She would go shopping first, and then take her bags with her to salon, like ladies do, and perhaps someone there might even ask her what she bought!

I decided that I liked the idea of her dressing as my secretary, to serve me. Of course, the note said that, as part of losing the bet, she would have to switch roles and serve the girls in the office for the day! :-) 

I must admit that I had a LOT of fun writing the note, and enjoyed thinking of what I like to do to certain men while I was doing so. 

We sent several versions of the note back and forth. At one point, I even had her copy it out by hand, as I thought it would reinforce what she was about to do. ;-)

However, I decided that it needed a few more changes. She didn't have time to copy it out and send it to me for approval again, so I allowed her to take a copy of the last version, printed in pink!

Below is the first part of her report, describing her Sissy Shopping Trip:
*

After discussing and agreeing with Mistress, she decided that it would be good for me to dress as her secretary. I was to go with a note from Mistress, saying that I'd lost a bet in the office and had to buy and wear the outfit at work the next day. I have been shopping for women's clothes before, but I have never involved any of the sales ladies before, apart from paying at the tills.

After a few drafts, Mistress sent me the note that I had to show to the ladies in the shop. It said I was to buy:

• a pencil skirt 
• a ladies' feminine blouse/shirt 
• sheer tights
• a lace-trimmed padded bra and
• accessories to compliment my outfit, such as a belt and necklace.

I had decided that I would go to the city centre, and which shop I would go to, as they seemed to have a lot of things and are generally not too expensive. I got up early and had a shower and shave (face :-)). I had managed to get to sleep most of the night, but did lie there for a bit wondering what would happen on my shopping trip.

I traveled in to the city on public transport. There were lots of ladies who were going to the office, wearing their nice smart outfits, and I thought to myself, that's what I will be buying soon: ladies' office wear! I felt very sissy thinking about it, how smart and nice they looked, and if I would look as nice. I arrived at the shop about ten minutes after it had opened.

The shop, having just opened only had a few customers. "Phew!" I thought. I wondered around the shop a few times, looking for the items Mistress had specified in her note. A young lady at the till asked me if I needed any help, so nervously I said yes. I felt excited and nervous, I was about to tell a lady that I was being made to buy and wear ladies clothes by my female colleagues! I nervously explained I'd lost a bet with the girls at work and handed her the note, printed out in a pink font!

She read it and said, "Oh, you need to pick out an outfit!" She turned to her friend and said she was going to take me around the shop.

She asked me to follow her. She had the note and started reading the items on the list out. She wasn't exactly whispering!

She took me round for the skirt first: She looked at a few on the rails and then asked another girl if there were any more pencil skirts. As I followed her round, she picked one and asked me which size I wanted. I told her and she took one off the rail. She then went out the back to talk to some one. She took the note, and shortly came back. I don't know what she said while she was in the back with her friend.

Black Textured Wave Pencil Skirt - http://www.newlook.com/shop/womens/skirts/black-textured-wave-pencil-skirt_284348001

Next, she started looking for a feminine blouse, and picked one out. She then found another, and again she asked her friend which one looked best. They both decided the second one looked more feminine.

Cream Sleeveless Shirt (Mine has two pockets.) - http://www.newlook.com/shop/womens/tops/cream-sleeveless-shirt_303231513

Next, she took me upstairs to the jewelry. While we were in the lift, she said "It's a nice skirt, isn't it" to which I replied yes, it was. I felt like such a girl, talking about how nice skirts look.

We arrived on the second floor, and she took me over to the jewelry. She looked around and asked another girl about necklaces and bangles, and which colour would go with the skirt and blouse. They agreed gold. (Note this is costume jewelry, not proper gold.)

They started picking a few necklaces out, saying which ones they thought went with the blouse and skirt. They thought a nice drop one ( I think that's what she called it) to sit in the open neckline of the blouse. They picked three out, and we chose one. Then they talked about bangles, again looking around and picking a few out.

Gold Chunky Chain V Necklace - http://www.newlook.com/shop/womens/jewellery-and-hair-accessories/gold-chunky-chain-v-necklace_303066793

Bangle - I can't find it on the website.

Next, we started looking for a bra. Her friend looked at the note and said it needed to be padded, so she started showing me them. She explained the padding, and how it gives it "more". The second lady started talking about back sizes and saying their sizes were different from those in a proper bra shop. They looked at the note and said she wasn't sure if they had any in the cup size on the note.

I said I didn't know about cup sizes, so she got two different ones off the rail and said "it means the cups are bigger", showing them to me them for comparison. We found a nice pink one with black lace, which I said I liked. ("Did I just say that?" I thought to myself!) The first lady agreed it was nice, but the second lady carried on looking through the rail and found some cheaper, so I settled for those. (I think they had forgotten about it being suitable colour for under the blouse, but perhaps being women they just know that kind of thing.)

[Ladies do know these things. Since it is a cream-colored blouse and you have light skin, a white or nude bra like the ones you purchased would be considered appropriate. The black lace on the pink one might have shown through in a fashion that would not be acceptable for the office. ~ M]

2 Pack Nude and White Push Up Bras -
 http://www.newlook.com/shop/womens/lingerie/2-pack-nude-and-white-push-up-daisy-print-bra_305608372

The second lady then said "If you're not sure on sizing, you can try them on if you like." I was too nervous to take up her offer, and we continued. "What's next on the list?" she asked.

The first lady said I needed a small clutch bag, so we made our way over to where the bags were. The second lady said that a belt would be better. Then a third lady asked, "What's it for?" and they had a discussion about whether you would wear a belt with that skirt. They held the skirt and blouse up, and demonstrated tucking the blouse in for me. "An elasticated belt would be nice," the second lady advised. I agreed with the belt, just in case the skirt didn't fit.

"He needs tights next, silky sheer ones." the first lady said, so the three of us went over to where they were. The second lady asked which colour. They had dark or tan, and they then again had a little discussion about what colour you'd wear with the skirt and blouse. They advised a light pair would be best, and the second lady started explaining the differences between the shades.

Nude 10 Denier Shade 2 Sheer Tights - http://www.newlook.com/shop/womens/accessories/nude-10-denier-shade-2-sheer-tights_282314712

The first lady then took me back down stairs to find a suitable belt. She picked one off the display. It was elasticated and has a gold coloured metal bar. "This one is nice. It's gold coloured, to match the necklace," she said.

Belt (not very good pic on website) - http://www.newlook.com/shop/womens/accessories/gold-wide-metal-bar-stretch-waist-belt-_314307701

"I think that's everything, on your list" she said and we went over to the till.

I tweeted Mistress that I had completed my shopping task and then went for a coffee.

I went into the coffee shop, ordered my drink and sat down, putting the bag of ladies clothes on the chair next to me. I replied to Mistress' tweet.

I didn't notice that the bag was open slightly when the lady brought my coffee over! I don't know if she saw any of my outfit.

After finishing my coffee, I went for a look round the shops before I made my way to the salon for the next part my girlie day: another full leg wax at the girlie-named salon.

*
Next:
Part 2: Getting my Legs Waxed Again at the Girlie Salon

Part 3: Wearing my Secretarial Outfit While Working From Home (With Pics of my New Outfit)

World Cup Chastity Game Rewards & Punishments: Punishment Report by submissive geek

As readers of my Male Service blog and Twitter feed know, I ran a "little" Chastity/Spanking/Edging Game for the World Cup. Among the players who weren't My subs, submissive geek was by far the best*, and we've been talking now about his Applying to Me.

*To Me, this means following my instructions regarding the Rewards and Punishments, including performing and reporting them in a timely and respectful manner, regardless of whether your team won or lost.

Those who played the entire game and won in the Final got an individually-designed Reward from Me, based on the Special Request ideas that they submitted privately as we began the Knock Out Rounds. This was their opportunity to ask for something extra special, new or different.

sophie was the only one who won this. Her request was to be sent to shop for a feminine outfit with a letter from me to give to the salesgirl. Yes, she got to enjoy every sissy's fantasy! 

She had a full day today of shopping (pic at right) and going to the salon, and her report is coming soon. 

The losers of the Final had to buy and wear black ribbons as cock rings in honor of the winner (Germany), and edge once while wearing it. 

That's jezi's hairy, censored, teeny peenie at left! (LOL!) 

submissive geek's somewhat more impressive pic is below. Since I'm considering whether I want to officially put him Under Consideration, I had him submit a detailed report. Besides, I knew many of you would be curious about how these last World Cup Rewards and Punishments went, and that he would probably welcome having his published. 

Enjoy! ;-)
*

My day started amazingly with a message from Mistress that, to my amazement, contained a recording of Her voice. It was so wonderful to hear Mistress Magick. I listened to it many times and it drove me crazy! Especially every time she said my name, mmm :)

Having been driven to new levels of horniness (on my seventh day of chastity!), I tied a black ribbon around my cock in honor of Germany. I wrapped a yard of silky black ribbon around my cock and balls quite tightly to make a cock ring effect and finished it off with a bow. I took a picture for Mistress. I then took the one edge Mistress had allowed me. It was very hard to stop wanking, but i managed to force myself.

Then it was time for my spankings: I owed Mistress 250(!), including interest, for backing Brazil in the game for 3rd Place. I decided to do them in sets of 25, alternating cheeks.

The first hundred weren't so bad, but after that they were landing on already sore skin and completing each 25 was very painful. I took a few pauses in between sets and managed to make it to the full amount. My butt was glowing, as was evident in the picture i sent to Mistress.

It was quite a pre-work session, and really hard [pun intended? ~ M] to just get dressed and head out without cumming. I was a horny mess all day at work and found it hard to focus.

The ribbon felt lovely though: the ends tickled and it held my package tightly, making it rub around more than normal. I made several visits to the restroom to tighten it up - i really liked the feel when it was nice and tight. It was a wonderful reminder of Mistress throughout the day.

Mistress was kind enough to IM with me that night, but primarily due to issues my end, it lasted less time than i would have liked. However, after much begging, i was allowed an orgasm! I removed my ribbon around 7pm, but unfortunately didn't have the privacy to cum, so had to wait another night and came in the morning instead. I tied my ribbon on again while i masturbated. i thanked Mistress Magick as i orgasmed, afterward licking up my cum from my hand as directed. i really am very grateful!

Mistress has decided to place me in chastity again, hopefully it won't be for so long this time! :)   [Don't tempt me, silly boy! ;-)]