My Halloween Fantasy: Dressed As a School Girl by simple twist

If you have been reading my Male-Service.com blog, you know that I'm challenging the boys and gurls out there to dress as their fantasies for Halloween. 

My new boy, simple twist, volunteered to dress up as a school girl for a Halloween party this weekend and then to let me share his report with you. I'm very proud of him as this was his first time going out in public dressed!

I'm hoping his report will inspire more of you to take a step outside your normal comfort zone and use the rare opportunity that Halloween gives you to dress as your fantasy - whether it be as a girl, a puppy, a baby - whatever your heart desires. Send your reports to me at: ForMistressMagick *at* yahoo *dot* com, and maybe I'll include them in my blog.

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Mistress Magick,

I decided to dress as a girl for my Halloween party earlier in October, shortly after You had told me that You often make it your Halloween assignment for your boys to dress as their fantasies. You hadn't specifically told me to do it, but I knew it was something You'd like so I decided to do it on my own.
[Good boy! I like a boy who thinks ahead about ways that he might please me. ~ M]

I decided to go as a school girl and started looking online to piece together a costume. I soon found a pink, short plaid skirt, a white blouse, white tights, black high-heeled Mary Janes, and a blonde pigtail wig.

I was afraid of going too far with the costume, as people would begin to wonder how much of this was something I wanted to do even if it wasn't Halloween. I decided the tights and heels would make me look very feminine, but it would be offset by my beard and the campy ridiculousness of the wig.

The big night came, and You were generous enough to arrange your schedule so that I could get dressed for the party on cam for You. I felt very vulnerable dressing for You. My sissy fantasies are the ones I have the hardest time coming to terms with, but it also made me feel very submissive to You when I was on cam dressed like a girl.

I could tell that there was going to be quite a contrast between my lower half and my upper half. From the waist down I looked very feminine, with my legs encased in white tights and given a nice feminine form with the high heels. Above the waist I had a beard and a flat chest, but if I looked any more feminine, I don't think I would have been able to get up the nerve to go out in public.

After checking me out full over, You finally sent me on my way to the party. The first thing I realized that I had underestimated was driving in heels. It was a bit awkward at first, but I got the hang of it within a few blocks. When I arrived at the party, I took a deep breath and walked up to the house. Before I could talk myself out of it, I opened the door and walked in to see all my friends. The initial shock was priceless - no one saw my costume coming! People were even more shocked when they realized that I wasn't only wearing a skirt and tights, but heels as well. Another friend of mine was also dressed as a girl, but he wasn't nearly as feminine as I was. While he was simply a guy wearing a girl's Halloween costume, at least from the waist down I was dressed like a sissy - in a short pink skirt, white tights and shiny black high heel Mary Janes.

Everyone got a kick out of the costume though, and soon I was able to relax, have a drink, and start having fun.

There was one woman at the party who was younger than most of the people there, and she seemed very much pushed out of her comfort zone with me dressed as I was. She couldn't stop staring at me, and whenever she walked by she'd say she couldn't get over how much I looked like a girl. I assume she meant my legs.

One of the girls looked at my shoes and told me that in an hour I'd have regretted wearing them. She wasn't kidding either. After a while my feet began to hurt, but I did my best to keep the heels on for as long as I could. But after being in them for almost 3 hours, I had to make a change. For the last hour that I stayed at the party, I was in my sneakers instead of my heels.

I got home around 1:30am, and decided to stay in my costume and put my heels back on as I relaxed. I ended up laying in bed still wearing everything, and fell asleep that way. It wasn't until I woke up in the early morning that I finally took the shoes and rest of my costume off and got into bed proper.

Going out like this definitely pushed me well out of my comfort zone, but it was thrilling at the same time, and felt good to put myself on the line like that for Your pleasure. I'm glad I was able to make You proud. I joked to a friend the next day that I'd have to keep the shoes handy, and next year I could "go as a French Maid or something". Who knows, maybe that'll happen.

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So noted! ;-) 

The First Night in My New Chastity Device by simple twist

My new trainee, simple twist, ordered a new custom-made chastity device just before he started training with me. It's a Queen's Keep (very appropriately named) from Mature Metal.

The device arrived last week, and I supervised via cam as he put it on for the first time. He has past experience with both plastic and metal devices, but this is his first custom-made device and it seems to be doing much better than any other chastity device that a boy has worn for me. Below is his report after his first night of wearing the device.
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Mistress Magick,

Last night was my first night sleeping in my new Queen's Keep chastity cage. I had it on for a few hours before going to bed, and everything remained as comfortable as a chastity cage can be. But I wasn't sure how I'd do sleeping in it, and thought it might wake me up throughout the night as I tried to get hard within the confines of the cage. That ended up not being an issue. I didn't wake up at all until about 6:30 in the morning, and that was simply to use the bathroom.

After getting back to bed and looking down at the cage, I did start to swell and fill the cage and feel it get very tight, but was able to fall back asleep because I was still pretty tired. A few hours later I did wake up as my morning wood tried to take over, but instead of getting hard it just stayed very tight in the cage. I lay in bed, feeling the tightness, and feeling incredibly turned on. I was able to drift in and out of sleep like that, however, so it wasn't keeping me awake any more than a normal night of not being allowed to touch. If I were unlocked but still under Your No-Touching Rule, I'd have been going through the same thing in terms of sleep: waking up a few hours early, feeling incredibly turned on but resisting the urge to touch, and drifting in and out of sleep until I had to get out of bed.

All in all, I'm impressed with this chastity cage, very impressed. So far, even without the Anti-Pullout Pin in place, it seems as escape proof as it can be. I'm not sure if I'd be able to slip out of it, but if I were able to do so, it seems like it would be a fairly painful experience. Like I said, it's a comfortable as one of these can be, and I can see why these are the ones that are recommended for those looking for long-term wear. When I grow and shrink within the cage nothing seems to pinch, and it isn't out-of-hand painful when I try to get hard in the cage.

Also, when I do try and get hard in the cage, the confine of the small space puts a stop to that, but it doesn't stop me from trying. When I'm locked up and turned on, I simply stay as hard as I can, filling out the cage as much as it will let me, which keeps me teased and horny without the ability to do anything about it.

Hopefully Yours,

simpletwstfate
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I must say that I was surprised that he didn't wake up several times throughout the night. I'm not sure how much of that is attributable to his past experience with chastity training, and how much is due to the custom nature of the device. I think it's likely a combination of both. 

Most of my past experience as a keyholder is with the CB-X000 line of devices, so I'm enjoying learning more about custom metal devices. So far, the Queen's Keep seems far superior in regard to comfort and wearbility, and I've heard similar things said about Mature Metal's Jailbird as well. 

Panty Shopping Report by Simple Twist

Simple Twist already had dozens of panties, all of which he purchased online. However, he had never shopped for panties in a real lingerie store before, and was very nervous about the prospect of doing so. Buying and wearing panties for me is one of the first things that I have any pantyboy or sissy do so, of course, it was his first training assignment - and first real test in applying to me. 

Enjoy!
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I woke up this early this morning, well before the mall opened. I was already frustrated, having now gone two days without an orgasm and under Your strict no touching rule. But, making matters worse, I couldn't stop thinking about my panty shopping assignment, and what it would feel like going into the stores to buy myself panties for Your pleasure.

Thinking that I'm making You happy is what gets me through it. As I lay in bed, I kept thinking how I want to be Your boy, and have it be Your cock, and have it exist for Your pleasure, and I knew that going shopping for some panties was a small price to pay in order to please You.

The mall opened at 11, which is about the time I left my house. I had already looked up the mall directory online and parked near the entrance closest to the Lane Bryant store. I wondered around the lingerie section, admiring all the pretty panties, looking out specifically for ones that I thought You would like. One thing I noticed is that there didn't seem to be anything in size 12, which is the smallest they carry on their website. So I started picking up 14/16's and they looked like they would fit.

Nothing was jumping out at me as panties I knew You would like, and eventually a sales girl came up and offered her help. She asked if I was looking for underwear to which I replied that I was. She asked if I knew the size and I said 14/16. She then asked if I was looking for cotton or not to which I replied I wasn't. The alternative to cotton was a nylon/spandex material so that is what we started browsing. I told her I was looking for stuff in blacks and dark purples.. She asked if prints were ok, and I told her they absolutely were not.

Then she pointed out these plain black brief panties with lace trim around the legs. They wouldn't have been my absolute first choice but I did like them, and I know you like black. So I told her that those might work and were a good start. Then she told me that they were on sale if I bought 3, and showed me some other options.

Then she held up another pair in black, but this time pintuck boyshorts with white lace along the legs and on the top. [Also see the picture above, from the Lane Bryant website, for a better view of the pintucks.] The contrast was a bit more feminine, which I thought You would like. I told the salesgirl that so far we were doing well and she said that we should find one more pair so I could get the special price.

I hadn't noticed any purple ones that I thought You would like, most of them were in prints and or just cotton. That's when the sales girl asked if red was a good color. I said that could work and she held up one more pair of boyshorts, this time red with red lace on the legs and the top. I said those would be great and took all three pairs of panties. (I couldn't find these anywhere on the website) I thanked her for her help and went up to pay.

 All in all it was an easier experience than I expected, though I was still a little nervous and felt vulnerable surrounded by all those panties.

I went back to my car, knowing You said just going to one shop would do for today, and I could go to another at a later time. But as I was driving out of the parking lot and tracing along to the other side of the mall to go home, I had a change of heart. I parked my car again and decided to go back in to check out Victoria's Secret.

When I got there, there was a really sexy and pretty pair of panties that I thought You would love just by the front door. It was a purple satiny material, with the rear and front portions connected by a thin strip of fabric. On top of the solid black in the front was a very pretty black lace design, blending well with the dark purple. Unfortunately, they only came up to size large and these looked like they would still be too small for me. Disappointed, I moved on to the rest of the store. When I got home later and went online I found they were the Cheekini panties included in the Limited Edition Seduction panty and push up bra set.

My first time around I noticed there wasn't anything in extra large anywhere I looked. When I doubled back to the front of the store a sales girl asked me if I needed help and I asked her if they even carry extra larges. She said they were limited and usually sold out the fastest, so it wasn't surprising that I couldn't find any. But, she said many styles run bigger in large and even have stretch to it so it was worth looking around. I showed her the panties that caught my eye first and asked if these would come in an extra large. She told me they didn't even make those ones in that size. She could tell I was still interested in them and then asked if I would be interested in the matching bra that came with those panties. This is where I was caught off guard and fumbled my words before getting a "no" out there. I think then she might have realized I was shopping for myself. But I took a deep breath and moved on.

She then directed me over to what were their Cheeky panties. These ones were very pretty, and the large seemed to have a decent stretch to them so I thought they might work. She told me that if I got three of these they were on sale for $30.

I looked through the drawer of larges and what first caught my eyes was this purple lacy panty with black lace trim on the legs and top. (The link doesn't show the color I got, the midnight leopard ones are the closest in color, but mine are less blue and more of a royal purple.) They were see through lace all over but the dark color and design seemed to make them not as revealing as they could have been. I decided to buy them thinking they might be just what You were looking for on me.

I looked around through the drawer some more and found a similar panty, purple with black lace trim but this time the main part was solid purple in a shiny nylon material that had a satiny feel. These also seemed perfect to wear for You so I decided to take those as well.

For the third pair I selected the same style as before, but this time in solid red with black lace trim.

I waited in line and paid for my panties, and once again the experience was easier than I had built it up to be.
My only concern was that the panties from Victoria's Secret might be a little too small.

When I got home I took the pictures that I'm sending You and tried on each of the panties. The ones from Lane Bryant fit perfectly, even being one size larger than we had considered last night. They held everything in place without being too loose.

Next, came the Victoria's Secret panties. I tried each one on, and while being on the small side, were definitely wearable. They didn't offer much wiggle room down there, but weren't really any worse in that regard than some of the lacy bikini panties I already own. They were also tight on my ass and felt like would give you a good view. All in all I was happy with the purchase.

I can't wait to model them for You, Mistress, and I really hope You approve.

Hopefully Yours,

simpletwstfate