Jessicas first date

[Jessica G]

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 .

I invited him to my 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 astranger 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. 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. It felt so good. 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 'girlfriend' and would ring me later this week.

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

He had earlier confessed that he very rarely dressed himself but had wanted to meet a tranny girlfriend.

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!!!! I never thought about myself as gay. But now I wonder :)

hugs to all!

Jessica
<3

[Alice Torn]

Nice and easy does, it, not wise to rush into full sex.

[Kate Simmons]

Sounds like it could be the beginning of a wonderful thing. I agree with him, take your time but fully enjoy being a woman. You will know soon enough if it's a relationship that will last. :)

[jigna]

Be careful with the strangers.

[Nikkilovesdresses]

I can't not say it- you were incredibly foolish, and extremely lucky - in more than one sense.

Have fun, but for god's sake don't take that kind of chance again with a total stranger.

[carhill2mn]

Go slowly, learn what you can about him. Decide what you really want and what you will be comfortable doing with him. I have met a nice man several times and his ideas/hopes were different from mine. I told him what I would be comfortable with. At one time, I suggested that I was not what he was looking for. Later, he accepted what I suggested. We enjoy having lunch once in a while.

[Tracii G]

You seem to like living on the wild side and thats fine but be careful please.

[cheryl reeves]

sounds like he wasnt being truthful about being cd,more like a " admirer of tg's" and using being a cd as a cover story. but if its something you might enjoy go for it. as for me if a guy ever kissed me he might not like the results.

[Jenniferathome]

...I never thought about myself as gay. But now I wonder

I think you can stop wondering.

[Lorileah]

she can still wonder. They didn't have sex. It could be, as I suspect a majority of people here who fantasize about having sex with a man while dressed, she could freak out and run away. Fantasy is always better and safe than real life. When it comes to contact....Most CDs would run

[Donnagirl]

I think you can stop wondering.

Yep.... I agree wholeheartedly

[Lorileah]

amazing how people here associate dating with sexual preference...Note, she didn't sleep with him... she didn't get naked with him...she didn't have sexual relations with that man. You all can tell her to quit wondering when she spends the night with him and he cooks breakfast. At least HALF the CDs here fantasize about dating and having sex with a man...yet they AREN'T gay. And when it comes to touching certain parts of the anatomy of a man or actually doing sexual acts, they wouldn't do it

[Sandie70]

As someone who tore through the 1970's and 80's with a vengeance, I might not be the one to give out advice. And since I'm bi, I partook of both worlds equally (maybe I should edit this - I make myself sound like such a ****). Anyway, it sounds like you had a wonderful time and I would hope it turns out great for you.

However.

The part where he said something about wanting you to be his girlfriend? After one spur of the moment date? Over the years I've had many one night stands, but not once did I ask someone to be my girl/boy friend after a single evening - and I was never asked. He sounds like a terrific guy, but be very careful.

[Donnagirl]

Not sure where you draw the line Lorileah, but French kissing a man in a passionate embrace and being left excited and weak at the knees kinda defines it for me...

[BLUE ORCHID]

Hi Jessica, I can't add anything that hasn't already said, But the way you wrote that
story it's like I was watching it unfold right before my eyes.:hugs:

Please do keep us informed. :daydreaming:

[Badwolf]

I don't know if it makes you gay but it definitely bumps you a few points on the Kinsey scale in that direction.

Being weak in the knees about the event can be a false positive since the excitement of just being out could do the same, liking the kiss just a tad less of a false positive though. You are at least apparently ok with being in sexual situations with people of the same sex that you identify as.

In the end though remember that even if you just discovered you are bi - monogamy is still an option. Evaluate your choices and make one that works for you and your situation before you take this any farther.

[Jenniferathome]

... At least HALF the CDs here fantasize about dating and having sex with a man...yet they AREN'T gay. ...

Come on Lorileah. It isn't just about sex and you know that quite well. Look at the description written. "...he gently grabbed me and kissed me passionately French kissed me and he caressed my arse. It felt so good." That's not a fantasy. It's a gay man wanting to get it on with another gay man. There is no reading between the lines here.

[Jorja]

Well my dear, if you want things to progress further, ask him to be tested for HIV/Aids and STDs. If he passes those test it would be time to make a decision. Are you ready for that?

[Badwolf]

Come on Lorileah. It isn't just about sex and you know that quite well. Look at the description written. "...he gently grabbed me and kissed me passionately French kissed me and he caressed my arse. It felt so good." That's not a fantasy. It's a gay man wanting to get it on with another gay man. There is no reading between the lines here.

I think you have it just a tad confused. The male on the "date" is definitely interested in having relations with a man dressed as a woman. No doubt about that. Wether he views her as a transexual, or a man does effect the definition of that person as a "gay" man in this situation. I still think it's clear because he looked for someone who fit the very specific category of man dressed as a woman, that the man part is at least part of the attraction. In less kind terms he seems like a tranny chaser.


Jessica G had one encounter so far, and it did not go as in "oh wow I'm gay I don't like women, I never knew". That is the point I think Lorileah is trying to make.

So far we know Jessica G had a wonderful time on a pseudo date in her eyes where she was treated like a woman. What part of that was at the core of her excitement isn't guaranteed to be a realization that she is purely Homosexual as "gay" would suggest. The way she describes some of the situations does appear like at least bi-curious as a potential and maybe more. Either way its up to her to say it and so far her words are "But now I wonder".

Let's not speak for her.

[Vickie_CDTV]

The biggest risk of all was letting a total stranger into your home while you are alone. Did you ever talk to him, or did he know any friends of yours that said he was ok?

He might have just lied to you about dressing just to get a date, did he even have any clothes with him? It was really presumptuous of him to assume that you would be ok with him French kissing you, or fondling parts of your body, without asking or talking about it first. Maybe it is because I am a "wimpy" guy, but I would never assume I would have some kind of license to do those things after one single date with a GG.

As far as being intimate with him, if you are not comfortable going there... you probably shouldn't go there. It might not live up to expectations, and you may regret having done it later.

[Pat]

That's not a fantasy. It's a gay man wanting to get it on with another gay man.

Um... I suppose they could be gay, but that wasn't revealed. I would have assumed bisexual on both their parts. Since I'm also bi, I suppose that could just be me imposing my "normal" on them. At any rate, it read wonderfully steamy to me. ;)

As far as the Stranger Danger warnings, perhaps we should presume she was monitoring the situation as it unfolded and was using her best judgement.

[Lorileah]

Come on Lorileah. It isn't just about sex and you know that quite well. Look at the description written. "...he gently grabbed me and kissed me passionately French kissed me and he caressed my arse. It felt so good." That's not a fantasy. It's a gay man wanting to get it on with another gay man. There is no reading between the lines here.
Really? It's a person, who is presenting as a woman who is describing a romantic encounter. Here is an excerpt I wrote about a man and a WOMAN

“Come up with me.” She asked him, “I don’t want to be alone tonight.” He felt conflicted. Yet here was the most beautiful woman he had ever known asking him to come up to her room. He smiled and nodded. She reached into her purse and handed him the key to the door. She pulled him up the stairs to her door. There she fell into his arms again and kissed him harder and more passionately than before. She felt him press her into him as if to consume her. She pulled away and opened the door pulling him into the apartment.


Now tell my that is any different than what was written above...Mine is two heterosexual people, meeting for the first time. The OP is a man dating a Transgender woman...who feels female for the first time. Nowhere did the OP say anything about male to male contact. Do you consider kissing, a man and apparently a woman , as a gay act? My writing is fantasy, fiction, made up in MY mind. She isn't gay... Read the threads that state how many CDs "DREAM" of being seduced, being taken, being kissed. And yet most of those will NEVER have male to male sex.

Beyond the fact that people CAN be BI and not be homosexual (How people here can stick with the if you ain't this you're that concept I have NO clue).

[Jenniferathome]

Lorileah, If you can't see a difference between "dreams" or "fiction" and actual acting out, I'm not gonna convince you. Jessica's own words are clear. I don't care if Jessica is gay or bi but I simply find it comical that one can "wonder" after writing a clear definition. Equally comical is the effort to explain that what was written does not mean what was written. This place will never cease to amaze.

[Vala]

Girls? Please stop this discussion you are having. If you what to discus what makes someone hetro, gay, bi, pan, etc. Sexual then please start a new thread. Don't use jessica's story thread.

With that said. Jessica it read likes you had a wonderful evening and I'm happy for you but I must say that I do find it a little risky to invite someone you hardly know into your home, it could have gone bad really fast. I always think it is wiser to first meet someone in a public place with lots of people and have a nice cup of coffee or soda.
If this story continues then please let us know cause the beginning is very interesting.

[Jessica G]

Hi!
Thanks for all comments. I was a bit thrilling to read them :) Love you girls.
The guy called me on the phone last night and we talk for an hour. It was really nice. He seems to be a serious guy and he hadnt been dating a cd before.
He said he think Im nice and cute and that he want to get to know me better :) I told him I want to see him again. Then he asked me out on a date on friday night :)

Hugs to all!
Jessica
<3:o

[paulaprimo]

hi jessica, congrats to you. sounds like you had a wonderful time and i want to thank you for sharing such a personal
experience. my take on the situation is that 2 consenting adults went on a date and had an awesome time. whatever
happens next is up to you and your business. just take your time, follow your heart, be safe and above all be happy!! :)

[TinaZ]

Dear Penthouse Forum:

I always believed your letters were fictitious until THIS happened to me ...

[TrishaLake]

Jessica it sounds like you had a great night. Good for you. I would not worry about labels just go with what you think is right. If this feels right then allow yourself this indulgence and always be careful. I am happy you are happy.

[jenn]

Congrats Jessica,

It sound like a dream come true. I am very Happy and envious of you.

Jenn

[Kaitlyn Michele]

I'm glad you had fun. Gay straight or bi or not who cares!!

Lorileah your arguments around gender identity and sexuality tend to eliminate the meanings of words that we all know such as fantasy and reality.

[Sissy_Michelle]

Jessica,

Congrats on a wonderful evening. I am not like most gals here... I don't live in a bubble nor will I. I fully believe in "no risk, no life, no life, no risk". You can be that person that later in life has said "I wish I could have done that, but now I am too old" or "boy that was stupid, I shouldn't have done that" each tells a story and a lesson learned. But the experience to help someone else later with an issue is far greater. I don't poke fun at the ones that don't take chances nor do I chastise those that have taken chances. To me it sounds as if you trusted him enough to meet with him and allow him to take you out. You had a wonderful time don't let anyone taint those wonderful memories.

However I do agree with Jenniferathome "I think you can stop wondering". Either you were caught up in the moment and we're just curious. Or your desire for him was real enough to for you to allow the wonderful time you had. Either way I I am happy that your evening turned out as wonderful as it had. Please keep us posted

@--}---
Michelle

[Dana Nichole]

You only live once. Explore. Have fun.

[Maria 60]

Iam very sorry if I come across the wrong way or rode. Lesson number #1. Never meet a person you barely know in your home, meet them in a public place. Be aliitle more careful in the future you just don't know who's going to show up at your door. Let's say you got lucky this time and let's hope he just doesn't show up unannounced. I don't want to be mean about it but a few years back I wanted to drive around dressed in a quit commercial area and I posted my intentions and one feed back was telling me if I was born yesterday and why drive at night in a quit area with nobody around, instead why not use have my brain and drive in a busy area and be safe. He was right and thanked him and lesson learned. Have fun be safe and let us know how it goes. You know us ladies love the gossip.

[CrossKimmy]

That is such a sweet story. I am straight, but I would be lying if I said I haven't entertained the thought of being treated like a lady by a respectable man as you did. I would have been weak in the knees as well!

xoxo

[jeniinnylons]

At least HALF the CDs here fantasize about dating and having sex with a man...yet they AREN'T gay. And when it comes to touching certain parts of the anatomy of a man or actually doing sexual acts, they wouldn't do it Totally agree. For some reason lately I have had that feeling of wanting to "feel like a woman". I don't think if the situation actually happened though I would do it.

[flatlander_48]

Lorileah, If you can't see a difference between "dreams" or "fiction" and actual acting out, I'm not gonna convince you. Jessica's own words are clear. I don't care if Jessica is gay or bi but I simply find it comical that one can "wonder" after writing a clear definition. Equally comical is the effort to explain that what was written does not mean what was written. This place will never cease to amaze.

Remember that this thread, to this point, represents ONE data point. Not saying there won't be others, but ONE data point isn't even a trend. Extrapolate this at your peril.

Now, I believe that the prose that was written is an accurate reflection of events and interpretations. But, corroboration is needed. Let's see how this develops...

DeeAnn

[docrobbysherry]

To back up Lorileahs point, when I began dressing out of the blue 17 years ago, I had plenty of fantacies that included sex with men. I was sure I had turned gay over nite. It took a couple of years to figure out they were fantasis about me becoming a woman. And, that I was not attracted to men. Yet, on occasion I have quite enjoyed being treated as, and feeling like, a woman by men. Sex being a completely different matter! Which brings me to my point.

There is no mention of sex in Jessica,s post. So, I believe everyone is jumping the gun. Whether they will get that far is pure speculation. If they do, will it be oral or otherwise? Will they both like it? He seems hesitant. Maybe its his first time with a male, too.

[Kaitlyn Michele]

Words once again have no meaning
From the OP

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. It felt so good. 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 'girlfriend' and would ring me later this week.

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

Its only a fantasy in a fantasy land where people call things that actually happened fantasy..
sorry making out and grabbing arse is sexual activity..

and who cares?
people that go through with this kind of stuff are often living out their true gender identity and calling it straight or gay is besides the point

its ignored around here all the time how much cd/cd sex goes on in the "community"

[Lori Kurtz]

Whether the label is "gay" or "bi" doesn't really matter. But you might as well acknowledge that you were very ready and eager for some sex with a guy. I've had one experience that was a little bit similar to yours, except that I was the one who was dressed as male. I was a bit shocked by my own feelings, and I was afraid to meet up again to go further. At this point, many years later, I have to admit that I'm a little sorry that I didn't find a way to do more of what happened that day. So as long as you keep in mind the advice of the sisters who raise the safety issue, I think you should enjoy whatever you enjoy about your femininity, and not worry about what to call it.

[MissTee]

Sounds like a journey of discovery. Why does it matter to have a label. Don't throw caution to the wind, but do have fun.

[Jessica G]

Hi!

It had been to long since I updated.

I have dating this guy all the summer now and Im still thrilled about. He seems to like me alot. After the fourth date I inveted him in for the and it ended up in bed. I someway I hadnt step up from it yet :)
It feels good to be his tranny girlfriend. And if it makes me gay. Im proud of being that too :)

Hug to all!
Jessica
<3

[Dana P]

Jessica

Loved your story. I've been about as far as your weak in the knees part 1, but I was the one who 'ran'. Never been through a summer of dating, but that to me would be a dream.

Curious-do you see him also when dressed in drab? The thing for me is that I can NOT see myself hanging together while i'm in male mode. I truly have no interest in that-I want to feel, look and be treated like a woman. The general view in here is that is gay...the most I can get to is 'bi' if one has to put a label on it. Also curious if the bedroom activity was as you hoped or expected?

In any event, sounds wonderful and I would be thrilled to have such an experience. I will also add that you were pretty lucky that this didn't turn out to be a dangerous situation....agree with the all the 'caution' warnings in general.

All the best
Dana

[I Am Paula]

What is gay? what is not gay?
When you find the person you can't wait to get home to, their sex becomes irrelevant.

[Kelsey21]

Well, the labeling has somewhat overshadowed something here. Wasn't the original intent of the date to dress and enjoy some wine and giggles? Has he ever dressed with you? Or was the "trannie" ploy used to just get his foot in the door? I'm glad that everything worked out alright for you as there's enough haters and freaks out there that this story could have been a tragedy.

[Tracii G]

Its all good if you two enjoy each others company.
Paula makes a very good point I think.

[AngelaYVR]

It was like the Taster's Choice ads all over again. Unlike those, we actually got a conclusion!

[Alexis08]

Edit: It was just meant as a joke. lol

[OCCarly]

Hi!

It had been to long since I updated.

I have dating this guy all the summer now and Im still thrilled about. He seems to like me alot. After the fourth date I inveted him in for the and it ended up in bed. I someway I hadnt step up from it yet :)
It feels good to be his tranny girlfriend. And if it makes me gay. Im proud of being that too :)

Hug to all!
Jessica
<3

Good on you that you found happiness. IDK if this relationship makes you a gay crossdresser or a straight MTF transgender, but I don't think it really matters as long as you are happy.

[ReineD]

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!!!!

Are you seriously asking whether or not you want to or should go to bed with him?

Maybe I grew up in a different world (I'm in my 50s), but the consensus among women of my generation is, if we invite a man for a glass of wine and we are dolled up with long red fingernails and are only wearing lingerie under a silk dressing gown, it most definitely sends the message that we want sex. If we don't want sex, then we wear clothing that does not have easy access to our bodies and that is not designed to excite men. This is "Dating Principles 101". lol



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 astranger I had only exchanged a couple e-mails with but I agreed.

You hesitated about going out in public on a date with him because he was a stranger, yet you had him up to your place for wine dressed the way you were? It just doesn't make sense.

Don't get me wrong, there's nothing wrong with dressing this way if you want to have sex with him and there is nothing wrong with having sex with him (just make sure you protect yourself for STDs) .. I have dressed like this too for my SO, but don't you know that we communicate our intentions with our clothing, even when just going out on a date wearing tight leather mini dresses and knee-high leather boots with 4 inch heels.

So I'm calling you on this. lol. I think you know what you want to do and you're just here showing off. :D :D :D