Bi Guy Meeting Experienced Sissy Advice

[2JST4fun]

I have had a few male bi experiences years back. I as many here find transgenderd girls hot to include cross dressers and sissies but never figured I would get a chance to play with one, much less one with a decent body. I had my prostate removed for cancer a few years ago and it's taken awhile for my sex drive to return. In the last year's or so the wife has been getting hard dick elsewhere with my approval. I can't produce cum anymore and my dick is over an inch shorter from the surgery. I am just now getting a decent errection at times but loose it quickly when we try to fuck. She said I should look around for a couple or a situation where I can get pegged and see if it really works for me before she will go there with me. She just recently decided she's ok with me having bi oral play. I have found a Sissy that's willing to play with me knowing my limitions. I am looking for advice from those here as to what the general norm is for what I can do with her. I don't have a big dick and can't flood her with cum but do think we can have some fun. I wanna be on my game as best I can. Here she is.

 

[2JST4fun]

OK, maybe I didn't pose the questions properly. Are most sissies desiring a submissive role or are they as flexable as anyone else on switching? I very much plan on giving head as well as receiving. Should I refer to it as a clit, dicklet or the usual cock reference? I was surprised to say the least that she's up for play and think it will be fun for us both. I don't have a strong Com nature but have played that role before. I just have to get the right mind set going. I have been in th L/S of swing for years and have been with a transsexual before but she very limited to things due to hormone therapy. It was still a great experience. I know there is a difference between transgender and a Sissy but I would like to go into this respectful in the right manner. Any advise is appreciated.

 

[FullSpectrum405]

I'm only replying to say congratulations on surviving cancer and finding your way back to a robust sex life! That is friggin awesome! Oh, and congratulations also for finding a willing sissy partner! She looks quite fun; I'm super jealous!

 

[2JST4fun]

Thank you, its been a long road and I have almost completely given up on having a sex life more than once. It may not happen with this Sissy but it looks promising.

 

[yukonnights]

There's a lot a factors we don't know about your situation. How long have you been acquainted and how much you have chatted/corresponded being two important ones. Without knowing that it's very hard to jump in a offer any meaningful input.

The main issue to me is; Is this to be an ongoing relationship or a one-night-stand? Obviously the level of communication is very different between the two. I think if it's a one night stand/casual thing it's going to be awkward. Not all "sissies" are total subs, but there is a strong leaning in that direction for most.

On the other hand; If it is hoped that this is to be more than a one night stand, I think the chances are more promising. The reason being; It's all more about the emotional connection than just concentrating on the physical. If you think this is the direction this relationship might go, then it opens up the door for intimacy w/o moving straight to intercourse...which will give you time to talk about things and also allow time for the "jitters" to abate.

There is also a real chance that she is a switch...I would just broach the subject and talk to her (before the big night if possible). I wish you both the very best and hope that something very special comes from it ~

 

[2JST4fun]

yukonnights

Thank you!
This is the kind of information I was looking for. It's hard to say because we haven't met in person yet but we live fairly close to each other and I believe we both hope this can be an ongoing thing. I just want to watch my behavior mostly in communication to not insult or make a reference improperly and offend. As alway maybe I am over thinking it. Again, thanks

 

[yukonnights]

Thank you!
This is the kind of information I was looking for. It's hard to say because we haven't met in person yet but we live fairly close to each other and I believe we both hope this can be an ongoing thing. I just want to watch my behavior mostly in communication to not insult or make a reference improperly and offend. As alway maybe I am over thinking it. Again, thanks

Thanks for the additional info. Since you are in communication, I would simply bring up the subject of the "ongoing thing" and then talk it through. I'm coming at this from my own personal preferences obviously, but I never do casual one-night-stands simply because they are not a turn on for me. Since it sounds like you two are also hoping for a bit more, why not just take you time, talk, get to know one another and see how you click. If there's chemistry and sparks then you can suggest a slower approach, etc. I'm thinking that, due to your recent setback, you would be able to perform much better after getting to know her better. There's plenty of time to talk about likes and dislikes, kinks and fantasies, etc.

Hopefully she is looking for much more than a big cock. That's porn stuff, for the most part and it's become a meme. A feminine male is still a unique individual. The hope is that she is seeking the same kind of relationship you are...and you can only know that after a few dates and lots of talk. There's so many ways to please another person physically...you could use dildo's and vibrators, for example. Again, I really hope she is seeking the same things you are...if she is, there's a good chance it might be a long term relationship. Lot's of talk...lot's and lot's of talk ...and kisses

 

[BiiCuz]

OK, maybe I didn't pose the questions properly. Are most sissies desiring a submissive role or are they as flexable as anyone else on switching? I very much plan on giving head as well as receiving. Should I refer to it as a clit, dicklet or the usual cock reference? I was surprised to say the least that she's up for play and think it will be fun for us both. I don't have a strong Com nature but have played that role before. I just have to get the right mind set going. I have been in th L/S of swing for years and have been with a transsexual before but she very limited to things due to hormone therapy. It was still a great experience. I know there is a difference between transgender and a Sissy but I would like to go into this respectful in the right manner. Any advise is appreciated.

I type in pink I refer to my body parts as fem..clit, ovaries, pussy, I say sir, master, or daddy by which I will be told, I am to obey, be honest, and worship It is not about me as a sissy, but about obedience

 

[SissySalina]

Not all sissys are alike but they all are people, this is where you start. Treat this person as you would anyone else.
As far as expectations, talk. You both need to talk to each other and discuss the situation, get to know each other a little. Main thing is, be yourself. Not knowing the sissy, this sissy will not try to say exactly what that sissy is looking for, as with anyone you need to find out for yourself. Like other people sissys are different in how they see themselves and you should find out how this particular sissy is.
Best advice from a sissy.

 

[BiiCuz]

Not all sissys are alike but they all are people, this is where you start. Treat this person as you would anyone else.
As far as expectations, talk. You both need to talk to each other and discuss the situation, get to know each other a little. Main thing is, be yourself. Not knowing the sissy, this sissy will not try to say exactly what that sissy is looking for, as with anyone you need to find out for yourself. Like other people sissys are different in how they see themselves and you should find out how this particular sissy is.
Best advice from a sissy.