u/sometimes-audrey

▲ 3 r/Sissy

Going for a drive

Hello ladies!
I’m planning on doing my first ever sissy drive! Tomorrow night some buddies and I are going out to see The Mandalorian and Grogu (This is the way🫡), and the showing is at 10pm. I’m pretty sure we’ll be exiting the theatres well after midnight and I’m planning to stop somewhere and change into Audrey to drive back home. I’ve packed my bag already and I’m really excited about it. Audrey’s never been out in the wild (lol) and I can’t wait to just be out and about! What was it like the first time you went out in girl mode? Any tips? I’ll probably report back with a car selfie!! Wish me luck!🫶🏻

~Audrey

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u/sometimes-audrey — 1 day ago
▲ 141 r/Sissy

Finally tried

So about a month ago, after years of fantasizing about it, I gave my very first blowjob. I had been talking with this guy for a few days and turns out he works very close to my place. He was super sweet and very respectful of the rules I had laid out so I just told myself “fuck it”, and gave him my address so he could come over during his break.

I had already been dressed and in girl mode but decided to change only into lingerie. Wig, lashes, breastplate and cage already on, I slipped into an all black strappy lingerie set and waited for him.

When he got here he was really excited. And I was NERVOUS. Soon as he saw me he complemented me on how sexy I looked, and started unbuckling his pants. I had laid out a chair for him so I told him to sit and take his cock out. To which he obliged.

This guy was a grower, cause his average looking cock swelled to about 8 inches long as I jerked him off. Once he was fully hard, I licked his shaft and took him into my mouth. In the moment I was like, holy shit there’s a cock in my mouth(!!!), and I couldn’t believe what I was doing. I blew him bareback for a few minutes just to get the feel and taste of it, then asked him to put a condom on as I didn’t feel ready to swallow cum just yet. He didn’t argue at all and put one on.

I kept blowing him for what seemed like forever. Alternating between sucking and handjob to even deepthroating and face fucking. After maybe 10 minutes of this he came. I got what I wanted which was to feel a cock pulsing in my mouth as he ejaculated into the condom. I gave a short aftersuck, he took off the condom and threw it in the trash, called me a good girl and left.

Now here’s the confession. I didn’t love it. I didn’t hate it but it wasn’t as eye-openning as I thought it would be! For YEARS I fantasized about it, wanting nothing more than to feel a cock in my mouth, have a man squirm as I pleasure him and feel the cock pulsing in between my lips as he cums in my mouth. I got all that and it was just…meh. I proceeded to delete my account (this one’s new), but not before telling him how I felt. He seemed disappointed but understanding which was super fucking cool of him.

Maybe I’m just a crossdresser and not an actual sissy. Oh well, maybe I just enjoy being girly!

Thanks for reading my story!

\~Audrey xoxo

reddit.com
u/sometimes-audrey — 13 days ago
▲ 7 r/sissyquebeccanada+1 crossposts

Allo! J’ai récemment essayer pour la premiere fois avec un homme (donner un pipe) toute en mode sissy/fille. Je ne suis pas certain de savoir comment je feel la situation, si jaime ou pas (jai pas detester mon experience en passant) et j’aimerais peut etre essayer à nouveau pour voir si j’aime vraiment ca ou si ce n’est pas pour moi. Alors tu peu me DM si je pique ton interet et on peu se mettre a jaser un peu!
francais/anglais ca me va!

Edit: si la personne que jai sucé se reconnais, hesite pas a me DM!

reddit.com
u/sometimes-audrey — 16 days ago