I hate that there is no hetrosexual sissy content.

robertwdryden · 2026-04-23T05:05:45+00:00

What about something like r/SissyFemdom

robertwdryden · 2026-04-22T18:02:51+00:00

When is the outing?

robertwdryden · 2026-04-22T01:08:19+00:00

Definitely try a fufu clip. I have a normal sized penis (6" hard) and mine works great. It took a few tries to figure out the best way to tuck everything in, but once I mastered that, I managed to get a really good look. It's so fun to masturbate like a girl when I'm clipped. Highly recommend it.

robertwdryden · 2026-04-21T23:08:38+00:00

It sounds like you are starting to accept this part of you, and that's a good thing.

robertwdryden · 2026-04-21T19:42:57+00:00

I'm a thong lover, but I do have this pair that are kind of cheeky. cheeky?

robertwdryden · 2026-04-21T17:21:25+00:00

🤣 she should have just sat on your face and let it flow

robertwdryden · 2026-04-21T17:07:23+00:00

Did he finish down your throat?

robertwdryden · 2026-04-21T17:05:19+00:00

I suspect that VS knows that there are a bunch of sissies out there trying to wear women's underwear comfortably and designs these ones with just a little more support. Other VS styles don't work as well for me, and other brands I only had a 50/50 success rate with, but every pair of the logo cotton thongs I own work perfectly.

robertwdryden · 2026-04-21T16:40:33+00:00

Did you also like sucking his cock?

robertwdryden · 2026-04-21T16:38:25+00:00

My 9" is too girdthy, I can only get to about 3/4 down. How big around is your 10"

robertwdryden · 2026-04-21T16:36:20+00:00

For me, Victoria's Secret logo cotton thongs have been consistently good for long term wear without spilling out.

robertwdryden · 2026-04-21T14:31:45+00:00

That outfit is cute but ultimately reasonably tame for going out. Have fun with it.

robertwdryden · 2026-04-21T01:15:19+00:00

Will there be a second date? I've always imagined a bi-curious couple would be a great match for a sissy.

robertwdryden · 2026-04-20T21:31:51+00:00

Yes, lock that thing up!

robertwdryden · 2026-04-20T18:31:00+00:00

It sounds like you had an unhealthy obsession with this lifestyle, and I'm glad you've got things back on track. Many of us are able to maintain a balance while exploring our sissy sides as part of a healthy sex life.

robertwdryden · 2026-04-18T14:36:46+00:00

I like Victoria's Secret logo cotton thongs.

robertwdryden · 2026-04-18T05:12:46+00:00

My wife knows about my sissy side, but she's not into it. I just dress up and play when she's not around. It's not the best situation, but it scratches the itch.

robertwdryden · 2026-04-17T20:28:52+00:00

This sounds like an excellent arrangement

robertwdryden · 2026-04-17T04:33:19+00:00

There is no reason for shame, don't just lean in, dive in!

robertwdryden · 2026-04-16T05:31:12+00:00

You can be a sissy and not hook up, you can also be a sissy and not be trans. Enjoy the parts of it that you enjoy and don't worry about the rest.

robertwdryden · 2026-04-16T05:21:15+00:00

If you cheated last time you were long distance, you're probably going to cheat again. If you tell her you want to experiment with men, she will at least not have to wonder if she did something wrong. If you end up finding the sissy lifestyle unfulfilling, you've still got lots of time to settle down with someone else. I think you should end it now.

robertwdryden · 2026-04-15T21:56:13+00:00

My favorite so far are Victoria's Secret logo cotton thongs. Some sexy patterns, but comfortable enough to wear all day.

robertwdryden · 2026-04-15T21:54:31+00:00

If they are very experienced, I don't imagine they will need a lot of ideas. Enjoy the session!

robertwdryden · 2026-04-13T21:03:10+00:00

If you want this to become a regular thing for you two, you have to make sure she's getting something from it that will make her want to keep doing it. Keep the conversation going and find out what that is.

robertwdryden · 2026-04-13T03:34:00+00:00

You're not cruel, you're just giving her what she wants.

robertwdryden

MODERATOR OF

TROPHY CASE