Sindy's first date

[sindystilleto]

Girls had to share my my experience from this Saturday with you all!

I've recently made contact with a another trannie locally and we arranged to meet for the first time on Saturday ( this was my first ever meeting with any body else!).

I invited him to my new flat for a girly night of trying on clothes a glass of wine and a giggle.

When he arrived I was a bit surprised as he was a very good looking macho type of guy, I was fully shaved fully made up inc long red nails and in my best black Basque thong & suspenders with a long black silk dress gown on top.
After he came in and I gave him a glass of wine and chatted I asked if he wanted to go & get dressed but he suggested instead that I get dressed and he would take me out on a proper date. I don't know what came over me he was a stranger I had only exchanged a couple e-mails with but I agreed.

I put on a black leather mini dress tight red jumper and knee length black 4" boots and over it all a full length leather coat. Apart from some walks late at night this was Sindy's first time out in public en-femme. It was such a thrill to hear my heels as we walked to his car and when he held the door open for me and I slid in very lady like I couldn't believe this was really happening.

We arrived at a local tranny friendly gay club and as we walked to the entrance he slipped his arm around my shoulders I thought I might faint with excitement!!

The rest of the night was a like a dream, he bought me drinks lit my cigarettes asked me to dance (not that easy in 4" heels I found) I powdered my nose in the ladies (that felt so good). Then it was time to leave and as we walked to the car he gently touched my arse and then held my hand. All I could now think of was do I continue the night and invite him in to the flat!

As we got to my front door and fumbled in my hand bag for my keys he gently grabbed me and kissed me passionately French kissed me and he caressed my arse. Just as I thought things were going to go further he broke of and said he didn't want to rush me into anything and he would like to take it slowly until I was ready and he didn't want to scare me off as he would like me to be his regular 'girl friend' and would ring me on Monday.

as he drove off I was left standing there weak at the knees and wondering what to do next.

He had earler confessed that he very rarely dressed himself but had wanted to meet a tranny girlfriend and was sorry for deceiving me but it was very hard to meet trannys in the area where we both live.

I would appreciate any advise on where to go from here girls as aim really confused as i had such a great night and it felt great to be treat like a woman and to be kissed by a man but the next step!!!!

hugs to all

Sindy

[dawnmcdaniels]

sindy, clearly the next step is to take pictures when you go out for all of us to see. You must have looked awesome for a cd to give up a night of dressing for a date. Even though hetero I understand the temptation you must have felt being a woman to even kiss a man. I dont believe I could have gone past arse touching. Follow your heart girlfriend but understand the consequences. Take it slow. And take lots and lots of pictures !!!!Black leather mini and boots....Thats Hot!!!!!:D

[Julie York]

Most amazing. Do tell us more. Where did you 'meet' this date? Have you ever been to that club dressed before? You said it was the first time you had been out properly. So you had quite an unbelievable evening all in all?

[Abby Lauren]

What a story, Sindy!!
Until very recently, I never considered having anything to do with a man. I still haven't done anything and don't plan to---yet. I do find your story intriguing and will be looking forward to your future advetures.

[Stelli]

Very nicely put as well. Hope you have enjoyed. It is all about experience. What you can do?
Do not spoil the excitement. Take it easy one step at a time. Maybe second date.
And write it down for us. I have enjoyed this story.

I am sure many of us have shared this moment of yours in our dreams.

[Deborah_UK]

Most amazing. Do tell us more. Where did you 'meet' this date? Have you ever been to that club dressed before? You said it was the first time you had been out properly. So you had quite an unbelievable evening all in all?

Funnily enough my thoughts exactly. What an unbelievable dream all round.

[sindystilleto]

thanks for all your comments / suggestions girls

since i last posted things have moved on a bit, Tony the man in my life (sounds strange saying that!) has rang and e-mailed a few times and we have agreed to take things slowly he suggested that we stick to kissing and cuddling until or if i want to take it further.
But i have agreed to go another date at the club with him on Friday, i've allready took the day off work to prepare but iam allready feeling more nervous than last time as it was all spur of the moment on our previous date and i did'nt really have time to think about it!!

i allready cannt decide what to wear and have covered by bedroom floor with possible outfits.

thanks again darlings

luv


Sindy

[Phillis]

Good luck on your date. I hope everythings goes well for both of you.

[Christa]

There's nothing that makes me feel more girly than being held by a man! Enjoy the second date and please keep us posted!

[Chelsea]

Hey Sindy, has Tony got a brother for me? :O) I'm so Jealous !

[Lindahexi]

Nice post Sindy, I think lot's of us girls woud feel as you do about attention from a man, it's all part of feeling like a real woman, and by the tone of your thread you really enjoyed it. I think you should follow your instincts and make the most of the relationship.

Good luck girl, hugs,

Linda.

[Christina Nicole]

This thread, from start to end, is one more nail in the coffin of every CDer who tells his wife, "Most crossdressers, like me, aren't gay." Then they come here and learn differently.

From all of us to all of you, a very heartfelt "Thanks."

Christina Nicole

[Shelly Preston]

This thread, from start to end, is one more nail in the coffin of every CDer who tells his wife, "Most crossdressers, like me, aren't gay." Then they come here and learn differently.

From all of us to all of you, a very heartfelt "Thanks."

Christina Nicole

Dear Christina
Just because A few may be gay dont get upset
We have a whole spectrum of people here and Im sure a lot of variation in thought and sexuality
I think there are enough people here to educate anyone who thinks most crossdressers are gay
There is probably a poll somewhere

[Christina Nicole]

I'm not upset, Shelly. But no crossdresser should ask his wife or girlfriend to go on-line or to view this forum to learn something about his crossdressing unless he wants to reinforce the impression that crossdressers are gay. It would be very, very counterproductive for him.

It's not an issue for me. My wife has her mind made up. If I did want to give her more reading material, I would get items written by experts and published through reputable channels. Sending her on-line would be a big mistake because of threads like this one. When trying to change someone's mind, you don't give him or her information that reinforces that person's prejudices.

Regards,
Christina Nicole

[Lindahexi]

Christina, the majority of CD's do claim to be 'straight' but many have openly stated that when fully dressed and made up, they would enjoy the attentions of a man; I don't think this necessarily means that they are gay; it is simply a further extension of the powerful femme feeling that some have, BUT ONLY WHEN DRESSED en Femme. If you look back through some early threads on this site you will find others views.

Linda.


I'm not upset, Shelly. But no crossdresser should ask his wife or girlfriend to go on-line or to view this forum to learn something about his crossdressing unless he wants to reinforce the impression that crossdressers are gay. It would be very, very counterproductive for him.

It's not an issue for me. My wife has her mind made up. If I did want to give her more reading material, I would get items written by experts and published through reputable channels. Sending her on-line would be a big mistake because of threads like this one. When trying to change someone's mind, you don't give him or her information that reinforces that person's prejudices.

Regards,
Christina Nicole

[Darlena]

I love being held & kissed like that myself. I feel secure & wanted that way. Mmmmmmm! More feminine feelings seem to rise up. Have a good time tonight! Love+kisses,

[Abby Lauren]

I have to agree with Linda. I did consider myself straight and heterosexual but, when thinking of myself more and more as Abby, the thought of being with a man only reinforces my femme feelings. I would never be interested in a man as a man. So, what does that make me? I used to think I was a lesbian because I was only interested in girls. Now I guess I can be called "confused" or perhaps I'm bi as a woman and straight as a man.
Still curious about Sindy's progress.

[sindystilleto]

Apologies girls for the delay in updating you all but I’ve been out of the country for a couple of weeks for the Xmas holidays
Sorry still haven’t got round to getting a digital camera and taking some photos I will soon promise!

If any thing I was more nervous this time as I was for the first date, as if you remember I didn’t know I was going on a date the first time!

I had the day of work so I the whole day to decide what to wear and get ready. After much deliberation I finally got dressed my outfit was a back corset & bra, tight black control knickers (my bits neatly tucked) black seamed hold up stockings and on top a recently bought pair of skin tight black leather trousers boot cut with a tight black crew neck jumper which showed my large false breasts of lovely! Black pointy toed ankle boots with a silver 4” heel and a large silver belt round my waist completed the outfit. Heavy makeup, long red nails , lots of jewellery and my favourite long blond wig in place I was nearly ready.

By now I was getting really nervous so a nice bottle of white wine was going down rather well.

I was just finishing the wine when Tony rang the bell I opened it to be greeted by a kiss on the lips!! I slipped on my full length imitation black leather coat (charity shop £25 looks real leather though) picked up my handbag and got into his car. A 20 minute drive and we parked just around the corner from the same trannie friendly gay club as the first date.

After the bottle wine at home I was now quite tipsy so after a couple of Jack Daniel’s & cokes I was well on my way to been drunk. After a few dances and drinks we managed to find a quiet dark booth to sit in and I was now really into been Sindy chatting & flirting with Tony. When he slipped his arm round me and passionately French kissed I thought wow!!! the next second we were all over each other kissing, and cuddling his hands were all over me and it felt really great.
By now it was getting late so we decided to go, we got in the car and after a couple of mins we were out of the city centre and in quiet back roads. Then I heard myself say to Tony pull over into a darkened car park. As soon as we parked I was all over him passionately kissing and cuddling when all off a sudden I found my long red nailed hands un zipping his fly and seconds later I was performing a oral sex act on him ( It felt such a natural thing to do).
As he drove me home I had sobered up enough to think to myself I had made a big step that night and it was best to get my mind round what I had already done and not to invite him in as I wasn’t sure what else I would allow myself to do as I was feeling so turned on. When I told him this he was a perfect gentleman and said he understood perfectly and wouldn’t pressure me and had really enjoyed the night.

He put his arm around me and walked me to the door after another kiss and cuddle we arranged to meet up in the new year as I was going abroad for a few weeks over Xmas.

Sorry girls I’ve waffled on bit I’ll let you all know when I see him next.


Hugs & kisses

Sindy

xxxxx[/COLOR]

[lil red]

Sounds like a smashing good time. Keep having fun in the new year!

[KathrynW]

Oh boy...here we go again. Where have we heard this same story before?
Next, I suppose you'll tell us you're still 100% straight hetero? ;)

[Billijo49504]

Do we all get an invite to the wedding?:)

[Methos]

wow sounds like you had a really good time. Can't wait to hear details on the next date. Also did you enjoy performing orally on him or did you regret it afterwards? Also hope to see pics soon

[randi_789]

After reading all the replies to this thread I felt compelled to reply. In another thread I asked if dressing was sexual or not. There were many different responses to that question, but Sindy's story I can understand. Just because you give head to a guy and want to be with one when dressed doesn't mean you are gay. Bi, maybe, but not gay. When i am enfemme I fantasize about being with a gentleman, and recently have met with someone I met online. It was heaven to be treated like a woman, even to the point, as Sindy did, giving him oral sex. But when I am not dressed I consider myself hetero. I look at women, but maybe not in the way a strictly hetero guy would. I lust after them, but at the same time, wish i could be them. Being a CD is not to be narrowed down to one blueprint for all. Each and everyone of us is different, with different needs and desires.

[KathrynW]

When i am enfemme I fantasize about being with a gentleman, and recently have met with someone I met online. It was heaven to be treated like a woman, even to the point, as Sindy did, giving him oral sex. But when I am not dressed I consider myself hetero.

You can also consider yourself to be Kermit the Frog, or Imelda Marcos, but just saying it, doesn't make it so.
Bottom, line...if you're giving some guy head, dressed or not dressed...
you are *not* hetero. :nono:

[JoannaDees]

To Kathryn and Christina ................ why do you care?

That said, one does need to be wary of the SO's personality before directing her here, and one does need to eventually accept who they are with or without labels.

[Tamara Croft]

I'm curious as to why Sindy is actually being questioned about being hetro? She never actually said she was. More to the point, a lot of CD's on this forum are single and are free to see whoever they please. I don't see an issue with having gay, bi or whatever label you would like to hand out members on this forum and as I am a GG member (partner of a CD) here, why on earth would it put other GG's/wives off joining? Is it now wrong for a CD to be gay or bisexual? What a crock of crap that is....

I just can't believe some of the issues that keep coming up on this forum regarding sexuality, if you're bisexual even in fantasy, deal with it, if a member on this forum is gay, get over it, they aren't going away, they belong here as much as the next member who claims to be straight..... so puh-lease, give it a damn rest already, because it's getting tedious.

[Deborah_UK]

Sindy - reading your post I guess you're from the UK, I was wondering where in the UK you are? Because its always nice to know the name of a tranny friendly bar if one is ever in the vicinity. What was the town and the name of the bar please? I do a lot of travelling so could add it to my list of places to go.

Thanks

[Diann]

I have to agree with Linda. I did consider myself straight and heterosexual but, when thinking of myself more and more as Abby, the thought of being with a man only reinforces my femme feelings. I would never be interested in a man as a man. So, what does that make me? I used to think I was a lesbian because I was only interested in girls. Now I guess I can be called "confused" or perhaps I'm bi as a woman and straight as a man.
Still curious about Sindy's progress.


I like to think Diann is a Lesbian.... NOT that there is anything wrong with being Hetro!:)

[KathrynW]

To Kathryn and Christina ................ why do you care?
Personally...I DON'T CARE at all what anyone does with their life. It's a free country.
I DO CARE when cd's come on this forum and talk about their sexual adventures with men and say "I'm still 100% HETERO...".
enough said.

[ReginaK]

That last date seemed quite awesome. :eek:

Just make sure you use some protection before any other encounters.

[Marlena Dahlstrom]

Um, Kathryn, neither Sindy nor Randi_789 never said they were 100% hetro...

I do understand you point about people not being completely honest about their sexuality, but to me it's the (self-)deception that's a problem, not their sexual orientation. Frankly a lot of the CD organizations aren't completely honest about CD sexuality (and it's variations), which I think it ultimately self-destructive. But as Tamara said, as a member of group that's discriminated against, you'd think we'd show a little more tolerance toward others who don't fit society's definition of "normal."

Incidently, it's worth remembering the difference between fantasies (stuff that intrigues you but you'd never actually do), desires (stuff you want to do, regardless of whether you've done it) and actual behavior. A lot of "normals" fantasize about stuff they'd never actually do. Both sexuality and gender are spectrums that society chooses to think of as dualities.