That Time of the Month by sophie

I've been thinking about trying to restart my blogs, and what better way than with the newest report, included below, from sophie. She's always been a wonderful sissy girl,and I'm really glad that she's back in my training. 

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Hi Mistress, please find my report attached, for my period training. Thank you for training me to be a girl.

I had been sorting through some of Sophie's things and found a packet of sanitary towels, that Mistress had sent me to buy a few years ago. As I remembered​ going shopping for them, I started to feel a little submissive and girly. I took a photo of the packet and tweeted it. Mistress saw it and tweeted back that it was appropriate timing and after a few messages she kindly agreed to put me on my period. 

Now as a male I am obviously never going to experience having a real period, and I know they are not pleasant and not something women would choose to have if they had a choice. So not exactly the nice part of being a girl - not like wearing make up, dresses and heels are - which sissies tend to focus on.

As a sissy I want/like to do and feel things that girls do, so I was curious about what it is like to have no choice but to wear them. As a submissive it allows Mistress to train, control and feminise me; giving me instructions/rules, she decides when my period starts and stops, how often and when I need to change my pads. Thankfully I wasn't required to change when I was out, that would have meant having to carry a spare pad with me and change in public loos, which I know that girls have to sometimes do.

[She'll need to do that next month, starting a few days in advance of when her period is die so that she isn't "surprised".  ~ M]

Mistress sent me my instructions and told me my period had started, so I had to put a pad in a pair of my plain knickers (she didn't want my pretty ones getting messed).

Obeying Mistresses order, I took out my knickers and a pad out​ of the packet. Laying the ladies underwear on the bed and opening the yellow wrapping the pads come in, unfolding it and seeing the pattern that they have on the top side and then the sound of peeling the sticky side away from the wrapper (they're designed to stick to your underwear) and then positioning it to provide appropriate coverage, wrapping the wings around and underneath the crotch of my knickers.

With the pad in place I put my legs through and pulled my knickers up, I could feel the soft pad between my legs and as it went up the front, cupping my sissy balls and clitty (depending on where it was pointing). The pads added a little extra bulk and firmness to my knickers, so I was always aware that I was wearing them. However I got used to them and they get a little flatter as you wear them through the day, they were more noticeable whenever​ I changed to a fresh one. I would say that it is like wearing padded cycling shorts, except your wearing them all day and night for days.

I felt girly and submissive when putting pads in my knickers, having ​to have a fresh one for over night and the morning. Mistress also made me look at my pad and check it whenever I went to use the loo, this was an extra reminder​ I was wearing ladies sanitary towels and I guess is what girls have to do, so I would also have to do it.

[Yes, we check to see how heavy our flow is and if we need to change it. If it's heavy, we might have to change it every time.]

I would feel the pad between my legs and constantly be reminded that I was on my period and under Mistresses​ control, and she was making me into a girl. 

I wondered what the ladies in the super market or street that passed by would think if they knew I was being trained to be a girl and made to have periods and wear sanitary towels. Would they be sympathetic? "Aww, you poor girl" and give me advice on what they do to ease and get through theirs; or laugh at me, call me a big girl and tease me; or even worse would it be like the changing room scene in Carrie?

Mistress also messaged me to listen to the singer Seal for half an hour, as that was what she was listening to. I guess it helps her relax and get through her time of the month.

[I was being all mushy and emotional - being on your period can do that to you! I started out listening to "Kiss From a Rose" and just kept going.]

I have to admit that when Mistress said that my period was finished, I was a little relieved, as while I kind of enjoy being trained to do girly things, it was becoming a bit of a chore, and as we'd had very hot weather here things were a little sticky. Of course a lot of ladies will be saying, "Tough! What do you think we do?" which of course is true. Ladies don't have any choice, so why should a sissy girl like me? My training was very good and I learnt what it is like to have to wear sanitary towels for almost a week, just like a girl.


Thank you Mistress,

Sophie

Going Out Dressed En Femme for Halloween by Sissy Tiffy

Halloween is the perfect time for sissies in countries where adults dress up for the holiday to go out dressed en femme, and while Sissy Tiffy was still very new to my training, I decided that she shouldn't miss the chance to do so. We didn't have the time for her to get a costume (a french maid's outfit would have been ideal) so she just dressed in the girlie clothes that she already had. She was required to go out and walk around for at least 30 minutes (preferably an hour), but was not required to interact with anyone. I gave her a release as her reward for getting up her guts and doing the assignment even though I knew it made her very nervous. 
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Part 1 - Day Dressed En Femme

After waking up, while I'm interested in being full en femme right away, I know that I have to switch my computer over to my other Skype to get ready for work. After a quick message, I can start. Using my body trimmer/shaver I religiously remove all my body hair. It's not quite shaving or waxing, but it gets the job done. Shampoo, conditioner, body wash, and a sugar scrub to help soften the skin, and I'm ready to start playing.

Unfortunately, my cock ring did not want to play nice. I tried just a bit of silicone lube, but it made it difficult to pull the skin of the scrotum through, and then my balls started to retreat as well, maybe from remembering the pain from a couple of days ago.

[The seam on her inexpensive metal ring was rubbing, and 2" seems slightly small. Tiffy has ordered a 2 1/8" ring from a quality manufacturer in order to correct the issue.]

My outfit consisted of a set of black comfy panties, tight but not skin tight feminine jeans, blue v-neck top, front-closing 50b nude/beige bra, and a cowl neck beige sweater (really soft).

About 10 minutes after getting dressed, I was then able to work with the cock ring and apply it all the way. I did have a concern of getting aroused often with it on though. However, this time I used a little bit of silicone lube so hopefully it won't catch onto the skin or anything.

Next was a wig, kind of light brown and very long, also sort of distracting while trying to get work done. (Wig was put on after I ate breakfast, still not competent in eating while having long hair yet.)

During this time it made me wonder what kind of things we would agree on in terms of changing appearance to please you - would you want me with long hair? Short? Would you encourage me to pierce my ears? Wear toenail polish at all times? All sorts of fun things ran through my mind.

I didn't have too much of a problem with getting aroused during all of this except slightly during putting on the lotion and the cock ring once it was on.

However, once I put on the lip gloss and I could smell and taste it, I started to get hard inside my panties and could feel myself throbbing and pulsing - definitely looking forward to an orgasm at this time. I haven't mentioned this before, but I do have a slight lip fetish, or lipstick/lip gloss fetish.

Of course, now it was time for work, so I focused on that.

After work was mostly done, as agreed, I dressed normally except for leaving on my panties and cock ring, as I waited for dusk and the treat or treaters. I was really tempted to start edging but I knew that touching wasn't allowed until I completed my task. The whole "kids coming by for candy" turned out to be mostly a bust and just left me snacking on chocolate. I should have realized that this area has very few families.

 Now I was left with a dilemma - originally I wanted to get full femmed up around 9pm, and probably take a walk around then or around 10pm. But I was so aroused after playing and talking with you, and being all dolled up from earlier, that I wanted to do it sooner so I could have my orgasm, yet late enough that I wouldn't be noticed. Another small part of me thought it would be super hot to just do the en femme thing, come back and do a whole bunch of edges with no orgasm and please you by being chaste - even though I would have no idea when the next time I would get permission to cum again.

[NOTE: Not cumming when I have ordered you to cum doesn't please me, as you are NOT following orders. Staying chaste longer than I want you to is usually about your own ego, not about pleasing me.]

During this waiting period I also became hesitant and thought about backing out too. I had a lot of strong mixed feelings about everything. Then you called, and I really felt connected to you and a lot more owned than before.

Part 2 - Going Out
(and Typing with a French Mani Now)

Around 9pm, I decided to get fully dressed again. I chose a different pair of panties - this type a thong as I thought it would be a good idea to feel a bit naughty doing this assignment.

Once dressed, I went ahead and did my nails, which took the most time overall. At this time I also decided to drink 4 cups of water. Finishing with my bracelets, wig and lip gloss. Once all done up, definitely felt aroused, then reached for the door.

I'll be honest Mistress, I held that doorknob for what felt like 5 minutes. I felt major apprehension. I felt like just telling you I did it, and lying. I felt scared. Since I live in a big apartment complex I started listening to people outside of my door - was it clear or not to go out without being seen? Was getting hard to tell.

After a bit of surge of adrenaline, I opened the door, and quickly locked it behind me. While walking away from my complex only one person looked at me, but we didn't make eye contact. I quickly walked over to the area where I planned on walking around, a nearby area with a small lake. I had to cross one main road, but other than that I stayed around the lake. During this time, I was pretty warm - probably the adrenaline still running through my body. I was hyper aware of everything - my thong riding up, my tight jeans, my soft bra, my wig constantly making its presence known, and my tasty lipgloss on my lips, with the wig sometimes sticking to it - I understand now why girls might not like sticky lipgloss.

Originally I wanted to stay out for an hour to impress you, but around 45 minutes out I could feel a little pain with my cock ring, and starting to get cold - the adrenaline of this activity was starting to wear off. I started to make my way home, coming to the realization that I'll have to brave my apartment complex again. Once arriving back, I had no incident, making my way into my warm apartment, letting out a huge sigh of relief.

Part 3 - Orgasm

Now that the adrenaline had worn off a bit, I felt tired and maybe that I should skip my orgasm and edges. I waited a bit, and thought about it. Could I go another week without orgasm? Would you make me go even longer than that? Would you make me edge constantly? What really made me want to have an orgasm though is being able to say the mantra that you gave me. I also wanted to orgasm and think about eating my own cum. I've never done it, but you wanted me to, and you wanted me to start develop the habit. It's a bit of a hard limit for me, and if/when I do it, I think it would make me have a really strong bond with you.

Of course, masturbating with a french nail set on is no simple task. I have to be gentle and can't really touch myself like I'm used to. 

Provided that it's also been 2 hours since I drank the 4 cups of water, would make edging difficult/fun.

Unfortunately I had to remove the cock ring. With it hurting while walking, I knew I might run into problems with it on while hard and aroused. But removing it with nails on, my goodness - it took a bit of patience to avoid pinching myself a bit.

Getting to the edge while thinking about all we've done, and the pictures I'm sending to you, and the fact that I'm typing all of this with my nails, still wearing my delicious lip gloss, and my wig, bracelets and thong - well it took very little time at all.

Thinking back to the last time we talked, I quickly approached the point of no return, repeating and thinking of the mantra over and over. Once I started  cumming, I was glad I was kneeling because I think my legs might have buckled underneath me, it felt so powerful. Once I came, I almost felt like falling asleep immediately for a brief moment. Relieving myself after felt really good as well. (I typically don't do anything with my bladder in terms of sexual satisfaction, but it was interesting to play with it a bit.)

[The bladder play was all Tiffy's idea... as if she didn't already have enough going on! LOL! ]

Notes and Feelings:

I could really feel a connection to you as I had my orgasm and did a bit of edge play for about 15-20 minutes, specifically when I would repeat the mantra. I liked dressing up en femme at home as well, and talking with you is always nice. The assignment really helped me overcome my fear a bit, at least in terms of going outside fully dressed and made up as a woman. With that said, I didn't like the going out part. Not because it was cold, or the clothing felt uncomfortable, or anything like that, but I didn't feel any "relief" of doing this, it just made me a bit uncomfortable. That said, I think I prefer just dressing up at home - it's a safe environment and dressing up is just - fun. I like the feminine nature of just being care-free, a little bit frilly, and trying on new things, similar to maybe most people's experiences with dress-up. Other than that - wow, what an orgasm, it was very intense. What an assignment too - I feel a bit worn out from all that, certainly a lot of things that I've tried this past week, my goodness. Thank you Mistress for helping me discover myself and really have a connection to you throughout all this. I hope you enjoy the pictures! :)

Pre-Halloween Pumpkining Report by cuckypantyboy

Yes, I made you wait a week for this, but the anticipation is good for you! ;-)

Continued from cuckypantyboy's Pumpkin Shopping Report

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This morning, I finally completed the pumpkining assignment. I could barely sleep last night in anticipation! I haven't had any release in about three weeks and haven't even stroked all week so I was very ready!

I waited until I had the house to myself then went to my truck to get the pumpkin that had been waiting for the last couple days. I took it into the house and cut one hole in it. Wouldn't You know it, this morning we had the first frost of the season and the pumpkin was quite cold! I wanted it to warm up a little so I left it sitting on the counter and took the time to put my panties in the laundry - another thing I have to do on the rare times I have the house to myself. I was so excited that I was shaking and my little dick was at least half-hard the whole time.

Once the laundry was started, I took the pumpkin into the bathroom and got naked. I didn't care if it was cold, my little boner was standing straight and I couldn't wait any longer! As I slid my penis into the pumpkin I was surprised at the feeling. Other than it being a little chilly, it felt quite good.

I laid it down on the floor so I could really start to pump it. The more I pumped the better it felt. The outer shell provided a rough friction while the inner seeds were delightfully tickling my head.

After just a couple of minutes I could feel myself getting ready to cum. I didn't want it to be done so quickly though. So I slowed down, grabbed my phone and took a couple pictures for You. I imagined You there watching me as I violated this pumpkin. The thought of You looking down at me laughing as I pleasured myself was too much to take and I started to squirt inside the pumpkin. The cum acted as a great lubricant and my orgasm was so intense. It felt like I squirted a gallon!

Once I recovered, I pulled out of the hole. One last drop of cum dripped from my shrinking penis. Without thinking, I knelt down and licked it off the pumpkin.

I feel a little foolish saying this, but I really enjoyed doing this assignment for You. Thank You for the opportunity to serve You in this way, Mistress.

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So...who's next? ;-) 

E-mail ForMistressMagick at yahoo dot com and volunteer for the Pumkining assignment.