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! :)