What have I been up to? Well keep your panties on (or don’t) and I’ll tell you! In short, two things.
#1 Working on a sissy hypno video and all the learning curve that comes with that whole process. It’s taking a long time but it’ll be worth it. (This one isn’t mine - but I love it)
#2 Preparing for the ultimate sissy week
I won’t reveal too much about #1 until I’m ready to release it. I do want to tell you all about #2 though! It’s so exciting to me.
Where to begin? In June, I decided to plan an all-out sissy week where I could spend a full week dressing up, getting professional sexy pictures taken, and (gulp) setting up a date with a man and maybe taste my first real cock and cum. I know some of you are under the impression that I’m a mistress. Sorry to burst your bubble but I’m a full on sissy bitch! ;)
I’m also a sissy virgin, meaning I’ve never actually met up with a man (as a sissy or otherwise) and performed any sort of sexual activities. It’s all been alone in my room and with me, my insatiable dirty thoughts, and my toys. I’ve gone through a lot of introspection and back-and-forth on it and have come to the conclusion for myself. I wanted to try it. I wanted it. I needed it. But the conditions had to be just right.
And to turn that fantasy into reality required a lot of work and preparation - especially if you value safety and discretion. And once I knew I wanted an actual man to desire me, touch me, and ultimately fuck me like the cumslut I am - I set out to make it happen.
Travel and hotel arrangements were taken care of. I’d be in downtown San Francisco. All I really needed were:
1. Clothes 2. Wig and makeup 3. Toys 4. A safe, clean, sane, hopefully handsome man
Clothes - I ordered some things online where I knew for certain they would fit me (panties, bras, stockings, shoes, etc - yes I measured myself). For other items of clothing, I planned a shopping trip (Old Navy, Ross, Sears, Macys - department stores are the best since they don’t really bother you in the changing room - grab clothes from women’s section and take them to the men’s fitting room).
Wig - I visited a local wig store where a really nice lady had me try on different ones and I ultimately bought two of them. One brunette and one blonde. I was thrilled with them. Wigs are expensive tho. They looked kind of like this as the blonde hair was shorter.
Makeup - I still can’t believe I did this. I went to a MAC store (Sephora was closed) and like a proud transvestite I asked about makeup and what would look good on me. They sat me down and taught me all about it. I was terrified the whole time but I ended up leaving with a lot of makeup, basic makeup knowledge, and an empty wallet.
Toys - just a visit to the local sex toy store. Simple enough. (Jewel butt plug, dildos, slutty lingerie)
A man - this was the really tricky part. How would I set up a date online with a man that wasn’t going to murder me, would actually like me, be 100% disease free, and would be trustworthy, horny, fun, and private enough to be with?
I posted on a few different dating sites (tranny, sissy, gay, etc). I received a lot of replies but they were all weird, short, sketchy, or just awkward. Then I received one message that seemed promising. After a few exchanges, he asked me to chat with him on the phone.
That was hard for me. Talking on the phone? Using my voice? Talking to a man under the context of being sexual / romantic? It was a weird feeling and I wasn’t sure what to make of it at first. But he was very casual and didn’t pressure me at all, which made it easier.
To make a long story short, we talked on the phone several times afterwards and I got a strong vibe for what sort of man he was and how we would interact in person. Plus, in his pictures, he looked tall, fit, and handsome which didn’t hurt. We made a date.
Sparing you the details, the day finally arrived for me to depart on my Ultimate Sissy Week. I had sketched out a rough schedule for myself and what sort of activities I’d like to do. I had done research on what types of sexy places I’d visit when I came. I also set a few goals for myself - what would be most fulfilling for me during this trip?
My goals were:
1. Finally suck cock and really taste it. Lick the balls. Just let myself enjoy it.
2. Taste and swallow cum. I wanted it shot on my face and into my mouth. Savor it. Finally become a real cum guzzler.
3. Go on a date with a man. Flirt with him. Have fun! Tease him. And submit and let him fuck me silly. My ultimate fantasy.
4. Get quality pictures of myself in full girl mode. I’ve done selfies and self-timer setups but have never had any quality pictures come out of them. I wanted some great pictures so I could relive it in the future.
5. Be safe in everything, leave if there were any signs - no matter how small - of danger, physical or disease-wise.
I will continue my story in the next post of what happened when I arrived, how the date went, what friends I made, and some pics of yours truly. Until then, be safe (but also slutty)!
