Seeking helpful advice - first date!!

[shemaleluv86]

Hi all, as title suggests -

I'm going on a date with a trans women I met online tomorrow. This will be my FIRST date with a trans women, and I'm feeling very nervous.

We're going for drinks.... And I'm hoping it leads to more afterwards.

If anyone can give me some advice to a newbie it would be so greatly appreciated. Things I'm generally conscious of are the DOS and DO NOTS, what sort of questions are inappropriate, how might a trans women feel about going on a date with a straight inexperienced guy, etc.

And just in case we end up in the bedroom - I need a WHOLE load of advice!

Thanks in advance!!

[Laphroaig]

Treat her like any other woman and don't expect sex after a first date.

[shemaleluv86]

Thanks for the response Laphroaig.

Both should go without saying!

[Will Riker]

Treat her like any other woman and don't expect sex after a first date.

Totally agree with Laphroaig, and if you are fortunate to end up in bed with her, treat her like a woman would like to be treated, before and afterwards.

[shemaleluv86]

Thanks Riker.

I guess it's more the gritty details. From a trans women's perspective; what are the typical things inexperienced guys do or say on a date that are frustrating, annoying, or maybe even offensive that you wish they wouldn't.

And in the bedroom - although I don't expect to go that far - what are vital bits of advice you can give a newbie straight guy? What info/advice would you have appreciated if you where in my shoes...

[Fitzcarraldo]

Not too helpful, I know, but "woman" is singular and "women" is plural.

But I figure you're already out on your date by now, anyway.

[Niko166]

What site did you meet her on? Any good?

[Lorca81]

I guess it's more the gritty details. From a trans women's perspective; what are the typical things inexperienced guys do or say on a date that are frustrating, annoying, or maybe even offensive that you wish they wouldn't.

Here's are some things you should not bring up and/or ask about first . . .

1) her dead name (i.e., the name she was given at birth)
2) her operative status
3) how long ago she transitioned
4) her sexual role (i.e., bottom, verse, top)

Here are some words and things not to say . . .
1) "tranny," "shemale," "ladyboy," "newhalf," "t-girl" "travesti"
2) "best of both worlds"
3) "you know what men want since you were one"
4) "real women" or "regular women"


And in the bedroom - although I don't expect to go that far - what are vital bits of advice you can give a newbie straight guy? What info/advice would you have appreciated if you where in my shoes...

1) communicate: if things get physical, straight up ask what she is/is not comfortable with. is point, you can probably use terms like "bottom," "verse," or "top." But be aware that some transwomen hate using those descriptors because the more or less come from gay male vernacular. Also, if you're not experienced with transwomen, also say that; assuming anal sex is involved, novices - whether they're the top or the bottom - require special care.

2) Be aware that some, but by no means all, transwomen have a tenancy to sleep with men sooner than ciswomen generally do. This is because some transwomen (sub)consciously seek validation of their femininity from men or feel that if they don't put out a guy won't like them. The stereotypical trannychaser, on some level, knows about this phenomenon and take advantage; don't be that guy!

[shemaleluv86]

Ha, all help is welcome.... Even grammatical!

[shemaleluv86]

Here's are some things you should not bring up and/or ask about first . . .

1) her dead name (i.e., the name she was given at birth)
2) her operative status
3) how long ago she transitioned
4) her sexual role (i.e., bottom, verse, top)

Here are some words and things not to say . . .
1) "tranny," "shemale," "ladyboy," "newhalf," "t-girl" "travesti"
2) "best of both worlds"
3) "you know what men want since you were one"
4) "real women" or "regular women"

Thanks you for the pointers, they re-enforce some things I thought were correct behaviour.



1) communicate: if things get physical, straight up ask what she is/is not comfortable with. is point, you can probably use terms like "bottom," "verse," or "top." But be aware that some transwomen hate using those descriptors because the more or less come from gay male vernacular. Also, if you're not experienced with transwomen, also say that; assuming anal sex is involved, novices - whether they're the top or the bottom - require special care.

2) Be aware that some, but by no means all, transwomen have a tenancy to sleep with men sooner than ciswomen generally do. This is because some transwomen (sub)consciously seek validation of their femininity from men or feel that if they don't put out a guy won't like them. The stereotypical trannychaser, on some level, knows about this phenomenon and take advantage; don't be that guy!

Great advice. I didn't appreciate that certain terminology comes from gay male vernacular - and I can see how they could be offensive!

I wasn't aware that some transwomen feel that way. I'll definitely bear that in mind, the last thing I want is to become a guy to take advantage!

[shemaleluv86]

Thanks for the advice above! I thought it was only fair to return to let you know how my date went (for those curious)...

I booked a small apartment in the city she was staying for the night, so I could enjoy drinks and not have to worry about travelling home late at night. I thought if the date fell through I could have a nice time in the city on my own anyway.

Early on Saturday morning I let her know when I'd arrive and when I'll be free, however, she didn't respond for hours. When she did she said that she had lost her purse and was unable to go out. Alarm bells!! She did explain that she would still like to meet, but that I'd have to visit her. This may be feel really uncomfortable, and I started to overthink this and was paranoid (being not only my first date with a transwoman, but my first ever online date!)..... my actual thoughts where "is this a scam?", "am I going to get mugged?", etc.

I nearly called the whole thing off. However, I'd come this far and after weighing up the options - and despite the risk - decided to met her. As we arranged she straight out said she "wasn't up for sex", and not "the best moment for it". I reassured her that that I did not have expectations for that, and sex wasn't all I was after.

She was staying just outside the city, an hours bus ride from where I was staying. Man I was a nervous wreck during the journey. My plan was to be cautious and prepared for the possibility of being mugged. I promised myself that if I turned up and had ANY doubts then I'd merely turn around and leave.

However, I arrived at the address and the person who greeted me was the one from the pictures. She was very smiley and friendly. W said our hellos, and I consciously scanned the place she was staying for any possible danger, etc. There was none. I had entirely over-thought and exaggerated everything. As it turns out, sh genuinely did lose her purse the day before, and although she didn't lose any money - she had spent the whole morning in contact with the bank to cancel cards, etc. After we had introduced ourselves, I came clean about what had gone through my mind and apologised - but she was totally understanding.

Okay, the unimportant and paranoia episode now out of the way....

First impressions of her was that she was quite tall, very slim, and had a sexy and attractive appeal. I was relieved she looked like her photos. She was very effeminate, but not completely convincing. For instance, I would tell she was a transwomen if I saw her in public. Her hands were large (compared to a ciswoman) I suspected she did have to shave her facial her, and I wasn't sure if she had breasts. She identified as transgender (as opposed a transexual).

She was very nervous too (all afternoon I was worried about meeting her, but I now realised how much of a risk she had out herself in). She offered me a drink, and we got to talking. We chatted and chatted... life, music, family, interests, etc. I liked her, she was fun. I think she found me attractive. As the night went on we ordered food, and continued to drink. I informed her that I had to be careful of the time, with the last bus home due just after midnight. She looked disappointment that I said this (I think she wanted me to stay, either longer or all night). I told her that I preferred to stay if she okay with this. I was aware I was getting a little drunk, and I wanted to remain respectful (remembering the advice from here about how some transwomens may sleep with a guy to (sub)consciously seek validation). She said I could sleep in her bed, while she took the guest room. At around 2 am we had a polite kiss goodnight (not a romantic one) and went to bed.

When I woke up early in the morning, and lay there in thought. I liked her, but didn't want to overstep my mark. After a while I got up to grab a glass of water and sat in the living room to contemplate what to do. She must of heard me, as she got up and came through to see how I was. As we were both tired, she asked did I want to go to bed...

We went through to the bedroom and cuddled. Eventually I asked her if we could kiss, and she obliged. Things went from there, and we fooled around. She has a very sexy body, smooth and slim, with an amazing ass! She liked having me stroke her cock, which was pretty big. She was versatile, but preferred to bottom. She stroked me, gave me blowjob, then lubed me up - and I fucked her cowgirl. During this she came on my stomach, and afterwards I got her to lie beside me and kiss me while I tugged one off and came everywhere too.

Afterwards we laugh for a bit and chatted, we laughed and enjoyed it. I had to leave after a while as I needed to check out of the apartment. She told me that she wanted to see me again, and I told her the same. We said our goodbyes and I left. Later that day I told her that I had great time, and that I hope she didn't regret having sex. She responded to say that I was very respectful, and that she really wanted to.

[Lorca81]

Out of curiosity, did you ever see this girl again?

[shemaleluv86]

Out of curiosity, did you ever see this girl again?

Sadly not, although we've kept in touch - we weren't able to find a date/time we were both free. I hope to meet he again though.