What naughty fun have you been up to this fortnight? (Aug 19th

I'm traaaaaaaaaaans! Started estradiol and spironolactone last week. They say it takes like 10 days to a month to notice things, and so far I haven't seen a reduction in sex drive or alertness beyond my usual ebb and flow. Hair loss hasn't changed either, but my facial and body hair is thinner and softer, improving the feeling after a shave. Finasteride or dutasteride would do the same thing, but I'm hoping for eventual total feminization if possible. (I'm fine with having a dick, but I'm a bottom so I don't need it.)

I'm fascinated with women's fashion, and my makeup collection now fills a purse. Between Goodwill and Amazon I've accumulated a fairly complete wardrobe. It's mostly slutty stuff of course, and it's always slightly disappointing that I don't yet have titties to fill the tops. I really dig the schoolgirl look. A cosplay set I bought comes with a microskirt that feels like a 26" non-elastic waist (I'm 30", maybe women's size 5 or 6) so the thing rides really high and exposes my junk. UwU I'll be replacing it with a better fit when I go out in public. Hoping to get groped by a stranger on Halloween or something.

Congratulations!! You have all our support here ❤️
♥️ welcome and congratulations!! This sounds like it has been and will be quite a journey!
Congratulations, and welcome to womanhood! On the boobs, and the "yet", we don't all get 'em. I am a woman who has always lived in a female body and at no point in my life could I fill a boob- focused shirt, not even while nursing. It's not a requirement, you can look very feminine with tiny tits, and very sexy, just gotta choose the right outfits.
- Thanks for the encouragement. My mother is flat as well, but even the slightest hint of breasts is a strong signal to some heterosexual males. I don't see myself as a woman and most others don't either, but at some point I expect the woman switch to flip.

I visited a theater friend of mine in Queens one morning before work. He likes giving me head usually at my place, so it was fun to see where he and his partner live. He gave great head as usual, and I helped him cum by sucking his cock and playing with his hyper-sensitive nipples. He made coffee too, so it was nice to hang out and catch up afterwards.
I had a second date with D, which had no anal but did include a sleep over and playing with my favorite Tenga masturbation sleeve. We both came a couple of times and had a lot of intimate fun and a little horsing around, too. I put the whole (long) story in a new community I made: [email protected]. Please share feedback to help me become a better writer.
I had some more fun (solo) with the same toy later that day.

That's a nice long story with lots of twists and turns. There were a couple of minor grammatical errors and the improper use of double quotes near the bullet points. I like the cute/naughty organization as it helps me find my place without overcomplicating things. It sounds very vanilla tbh, but I guess D is that kind of guy. To me, dad body jerk-off isn't exactly the sexiest thing, but I'm sure to some people it's really hot. (I didn't watch the bonus video but I'm sure people will appreciate it.)

Had some pegging planned that had to be postponed. Goddess took pity on me though. She let me out of my chastity cage, then put on Star Trek TNG. She lubed me up, and teased my cock throughout with her hand. She went back and forth between really working the sensitive parts of the head and basically just holding the shaft, not stroking it. I was straight up whimpering after the second episode started and asked her to really edge me, which she did, got 3 phenomenal edges in and then on the 4th I fucked up and didn't tell her in time and a little bit of cum came out 😖

I wasn't punished, thankfully! But it was a good reminder of an area I can improve.

Do you remember which episodes of TNG? Or were you too distracted to pay enough attention? To do that for almost an hour without getting tired she must have great hands.

I have a friend that wants to suck my cock while we watch Star Trek lol.
- I was paying attention at some times! I went a tad soft during a part or two 😅 it was The First Duty and Cost of Living. The First Duty was not sexy at all, then we get to Cost of Living and it had a few sexy bits juuuust a bit after I came. Whoops!! They were just the next 2 episodes in our rewatch y'know.
  
  You better cherish that friend! And let them do it 😆

A lot of nothing. Been watching a little porn here and there, plus some quick stroking. But outside of that the life has been dry.

What naughty fun have you been up to this fortnight? (Aug 19th - Sep 1st)