Dating Boys!

[mandonlym]

So hey, the guy I've been dating and I had a long talk last night about him finding out I'm trans. He wants a couple of weeks on his own to think (he's a serious one and wants to figure out if he can handle it in the long-term) and has given me permission to go out on dates in the meantime. So I reactivated my OkC profile and scheduled four dates this weekend. Let's talk about dating boys.

The schedule right now is as follows:
Friday afternoon - drinks date with a doctor.
Friday evening - seeing a play with a massage therapist.
Saturday night - going out dancing with a tech entrepreneur.
Sunday - brunch with a guy who works for a charity that does disaster relief.

It's winter here so I dunno if I can get away with a dress. I might just wear a tunic and tights on Friday and then wear lots of layers on Saturday that I'll check at the club, and wear a sparkly tank and high-waisted jeans. Then I have a cute brunch dress on Sunday that I can pair with boots.

Makeupwise I'm really basic these days. I just do liquid eyeliner, curl my eyelashes, put on mascara, then lipstick and lip gloss. Sometimes I wear foundation if I'm feeling blotchy and I might wear more dramatic makeup for clubbing since it's going to be dark. Thank goodness there's been a bleached eyebrow trend so I can be lazy and not color in my very blonde eyebrows.

I'll report back with any new insights and events, and post outfit pictures if I have time (Is it too much of an invasion of privacy to post pictures of the boys? Probably). In the meantime, feel free to ask any questions about post-op dating. Maybe a couple of you veteran daters out there can join me in sharing experiences.

[stephaniec]

sounds great. Have a good time and share the stories.

[Jodi.LP]

Oestrogen has made me finally realize that men have cooties

[mandonlym]

ha ha we all have cooties. but maybe men do have a few more of them. i adore them though. i mean, i adore women too but i guess i prefer men.

[Joanna Dark]

Your outfits sound great! Where I'm at spring is coming or here, so I can finally wear all my holey skinny jeans/capris and cute open necked form-fitting tops. I wear tons of stripes.But I have two really cute scoop necked print tees that I just love and show make my body look amazing so I'm so glad winter is over. Plus, I bought this super cool fitted waist leather jacket and I look a pretty badass bitch in it lol

But I have been tlking to this one guy, he's sorta a we bit older than me at 45 but he's cute and we seem to be hitting it off. Buy I broke up with my BF in mid-February so I kidnda feel like maybe I shouldn't. I just hung out with him today and he said he doesn't want to be in a relationship with anyone right now so if I'm not willing to be just friends than I should prolly walk away. I won't lie I hope he changes his mind and he does a lot and ya know he does still always touch me all the time and is always leading me a long cause I walk slow, but I should't read into things. He's really supportive though and he's a great friend so I pretty much have to be okay with it since I want him in my life. I wouldn't have made it this far without him. The one thing he said a couple weeks ago was that if I started dating another guy from him if he wanted to date me again would I break up with the guy. And the thing is I would.

So Im' stumped on that one.

But I am going to see where things go with this guy so I guess we'll see. But good luck on all your dates! That's a full schedule. My self-esteem is through the roof right now cause every guy I passed today, well almost every one, or a lot, were all "hey little mama" or het sweetheart how's it going?" lol I've been really down on my looks so I really needed that.

But if you wanna talk about men, that's one thing I love talking about. They're kinda like subway trains, if you miss one, another comes along in ten minutes and ya just hop on that one for a ride lol hehehe

[jussmoi4nao]

Its funny cuz everybody always says dating as trans is like so hard, but really I haven't had any trouble, tbh. I get about 90 messages a week on average on OkCupid, aand I spill T on my profile...first paragraph. And its not like they're ->-bleeped-<-s either, soo.

I've been dating this one guy for a while. He's really cute and we have fun, but I'm not really looking to label it. We're just kind of hanging out and going with it. I talked to him tonight, and we decided we were going to try have actual sex next time we hang out..I was soo glad when he asked cuz I'm very much ready, haha. I've actually never let a guy do that before, I always just give them oral, but I've reaally wanted to, this time.

Then there's lots of other guys who want to take me out, and you know a lot are cute, but kind of macho seeming so I always get turned off by that because I try to be very very careful with who I go out with now. There's another guy I reaaally like..like a LOT, but he lives too far to really date

Anyway, when I date I generally wear my usual makeup. Foundation, concealer, lashes, mascara, veeery light liquid liner, and blush (sometimes bronzer). I don't wear much eye shadow, just usually a clear shimmer. Then for clothes it depends on weather, time of day, etc. For coffee if the weathers nice, a cute dress with a hgh hemline is good (like polka, I loove polka dot). For dinner a sweater (short or long sleeve depending on the weather) and skinny jeans are always sexy but classy. Then for going back to his place for a drink, a sexy low cut or off the shoulder top and a mini skirt or short shorts is the way to go

[Janae]

Wow you have em lined up don't you..lol

Sounds like fun I hope you have a great time. The guy who has you waiting better act fast you might be off the market at the rate your going.

Have fun and spray on some extra perfume for good luck.

[mandonlym]

Its funny cuz everybody always says dating as trans is like so hard, but really I haven't had any trouble, tbh. I get about 90 messages a week on average on OkCupid, aand I spill T on my profile...first paragraph. And its not like they're ->-bleeped-<-s either, soo.

The secret of course is to be young and hot. At 25, the last time I did online dating, I couldn't keep track of my messages even back when not that many people were doing it. Now at 38 I still get about 30 messages a week and that's more manageable. I find though that not being so glammy means people tend to be more serious when they message me.

[mandonlym]

Sounds like fun I hope you have a great time. The guy who has you waiting better act fast you might be off the market at the rate your going.

Ha ha, no he's the one. He knows it and I know it, which is why he's scared s**tless. Not saying there couldn't be others out there but I've been dating for 13 years now and have never felt as strong a connection as I do with J. But because the connection is so strong, he has to deal with pressure that other guys I've dated haven't dealt with, as in, can he spend the rest of his life, make all the sacrifices, etc., to be with me. I've never been the marrying type but I want to marry this guy, and maybe even take up my sister's offer to surrogate for me someday (eek).

But hey, I can also have my freedom and it'll be just as much his loss as mine if he ends up giving up on us. And I may not feel the same way about anyone else in the future, but it doesn't mean I can't fall in love and build a life with someone else too.

Omg, I'm growing up.

[jussmoi4nao]

Ha ha, no he's the one. He knows it and I know it, which is why he's scared s**tless. Not saying there couldn't be others out there but I've been dating for 13 years now and have never felt as strong a connection as I do with J. But because the connection is so strong, he has to deal with pressure that other guys I've dated haven't dealt with, as in, can he spend the rest of his life, make all the sacrifices, etc., to be with me. I've never been the marrying type but I want to marry this guy, and maybe even take up my sister's offer to surrogate for me someday (eek).

But hey, I can also have my freedom and it'll be just as much his loss as mine if he ends up giving up on us. And I may not feel the same way about anyone else in the future, but it doesn't mean I can't fall in love and build a life with someone else too.

Omg, I'm growing up.

Woww, did anyone ever tell you you're a really amazing person?? I mean, you're like my new role model, here. I feel like if I were in love with a guy and he tried to leave my entire world would come crashing down. I know you're only 38, but you still seem very wise

[mandonlym]

Woww, did anyone ever tell you you're a really amazing person?? I mean, you're like my new role model, here. I feel like if I were in love with a guy and he tried to leave my entire world would come crashing down. I know you're only 38, but you still seem very wise

That's super-nice of you to say! You know you remind me of me at your age. We've been fortunate to have been dealt a good hand in the attractiveness lottery and you're just coming to terms with that. Over time you'll see that the trans stuff is just a tiny part of how people see you, and that you will love and be loved by many people. Having myself been in the position of letting go of people who have been in love with me for various reasons (and regretting it later in one case), I think you come to realize over time that not everything works out and that's okay, because eventually something does.

It's funny because I've been contacting exes recently asking them how they came to terms with me being trans, since I've never asked them before. I've asked three so far and they all say the same thing: "You know, I forgot that you're trans until you asked me." People are much more likely to interact with the person you are rather than your history, and it's really fascinating to know how differently others perceive you compared to how you perceive yourself. Btw, one of those exes was someone I dated pre-SRS. Sex was fun and not really an issue for us. We just broke up because we figured out that we're much better as friends than lovers.

[jussmoi4nao]

That's super-nice of you to say! You know you remind me of me at your age. We've been fortunate to have been dealt a good hand in the attractiveness lottery and you're just coming to terms with that. Over time you'll see that the trans stuff is just a tiny part of how people see you, and that you will love and be loved by many people. Having myself been in the position of letting go of people who have been in love with me for various reasons (and regretting it later in one case), I think you come to realize over time that not everything works out and that's okay, because eventually something does.

It's funny because I've been contacting exes recently asking them how they came to terms with me being trans, since I've never asked them before. I've asked three so far and they all say the same thing: "You know, I forgot that you're trans until you asked me." People are much more likely to interact with the person you are rather than your history, and it's really fascinating to know how differently others perceive you compared to how you perceive yourself. Btw, one of those exes was someone I dated pre-SRS. Sex was fun and not really an issue for us. We just broke up because we figured out that we're much better as friends than lovers.

I'm so flattered you say that because I've been reading your posts lately and you seem so centered and self aware. And like you have such a stunnning and unique beauty and seem to have had so many diverse experiences. I really think it's inspirational!

And yeah, the funny thing is everything in my life is sort of beginning to take shape and color and it's a bit dizzying and confusing atm. I'm getting more attention than I expected in general and people are nicer than I'd expected.

The interesting thing is being transgender is basically losing it's big dealness. Like a lot of guys are interested in me atm, and most of the time it never even comes up expect for me to say "you sure you're okay with?" mostly they just say sweet things like "you're like a dream girl" lol. Then one guy basically told me when went out he frequently forgot I was even trans, haha.

I think it helps that I stick to college/artistic etc type communities. I get the feeling the same is true of you.

[mandonlym]

I was working at MIT when I transitioned and science guys are surprisingly wonderful and rational about stuff like this, along with my artist friends. The biggest mistake I made during that period was letting men's attraction for me define my self-esteem because, like you, it felt amazing that my expectation of being rejected didn't end up happening. So I feel like during that period, I slept with people to boost my ego, which is not a good reason, especially when some of those people were jerks who just saw me as an object. I'm just as sex-positive these days, but I sleep with people because I like them and I derive pleasure out of sleeping with them.

Are we derailing this thread? Feel free to pm me any time if you'd like any information or advice!

[Janae]

Ha ha, no he's the one. He knows it and I know it, which is why he's scared s**tless. Not saying there couldn't be others out there but I've been dating for 13 years now and have never felt as strong a connection as I do with J. But because the connection is so strong, he has to deal with pressure that other guys I've dated haven't dealt with, as in, can he spend the rest of his life, make all the sacrifices, etc., to be with me. I've never been the marrying type but I want to marry this guy, and maybe even take up my sister's offer to surrogate for me someday (eek).


Omg, I'm growing up.

Awww I know how you feel. I've been in love with the same man I met when I was 19-20 for the past 11yrs. We've been off and on over the yrs because he had similar hangups as your guy. But now that he's older and more mature he's in a place where he's let a lot of those things go. We've been through everything possible already to hurt each other, but we can't stay away from each other. I broke up with him in 2009 and we just got back together last month. We've been discussing marriage and he's ready.

Love is crazy, but when it's meant to be things just fall into place.

[mandonlym]

Awww I know how you feel. I've been in love with the same man I met when I was 19-20 for the past 11yrs. We've been off and on over the yrs because he had similar hangups as your guy. But now that he's older and more mature he's in a place where he's let a lot of those things go. We've been through everything possible already to hurt each other, but we can't stay away from each other. I broke up with him in 2009 and we just got back together last month. We've been discussing marriage and he's ready.

Love is crazy, but when it's meant to be things just fall into place.

Omg don't tell me I'm going to have to deal with this for another decade! I wanna have cute babies and I'll be sooooo old by then. Seriously though, I was just telling jussmoi4nao over pm that this is totally the kind of situation where I can see him possibly only coming around when I'm with someone else, and how awful that would be because I really lack any willpower to resist him. But maybe I've just been watching too much Grey's Anatomy.

[mandonlym]

Ok here's a picture of the outfit and a rather boring picture of my makeup... sorry about the quality and lack of full-length mirror. Getting ready at my mom's:



The top is from bebe, which I snagged from my little sis. I forgot that since I lost weight we're the same size again, so I raided her closet. I'm wearing it with black tights and a black half-boot. Makeup is Neutrogena Foundation, Urban Decay Liquid Eyeliner, Maybeline Mascara, L'Oreal Lipstick, and YSL Lip Gloss. Don't do lip liner anymore even though it looks good because it makes me look too high-maintenance and I'm really not. I also don't wear black mascara a lot these days but I decided it goes with this outfit.

Here's a closeup of my face:



Notice me rocking the strong brow, he he.

Tonight's agenda: going on a drinks date with L the child psychiatrist at 5:30. He's 36 (I'm 38) He sent me a really nice text and I'm getting excited for that. Might want to squeeze in a proper dinner date with him this weekend if we get along.

Dinner and a play with J2 the 30-yo massage therapist starting at 7:30. Calling him J2 because there's J the guy I'm smitten with who wants us to take a couple of weeks off so he can process whether he can deal with me being trans. I've gone out and had fun with J2 before. He just texted me and said he just got his room painted and I should see it. We all know what that means!

Will update tomorrow!

[stephaniec]

you look great. have fun

[mandonlym]

Thanks Stephanie! Just got back home after my museum and dinner date with A., and having spent the night at J2's place, and I realize I don't want to call him that so I'll just call him by his actual name, which is Josh. We don't have the immediate spark that J and I have but it was still lots of fun to be with him, and the sex was really good. I feel like I can definitely continue dating him and let the relationship evolve if J decides not to be with me. I had some doubts about whether I can take him seriously because he's six years younger than me, but he showed a sincere and loyal side I hadn't seen the previous times we've hung out. And even though he's straight he has already explicitly referred to trans friends and has shared trans-rights related stuff on Facebook so I don't think disclosure will be anywhere near as hard as it was with J. Also when I told him my birthday was in June he said it might be fun to spend that weekend at his parents' place in Connecticut because they have a swimming pool. That kind of indicates that he probably wants me to stick around for a while.

The museum date with A was fun but I'm thinking the vibe is more friends than dating long term. I also had that drinks date with L Friday after work, which is also really promising. He's a highly accomplished doctor and seemed a little on the arrogant side from his online profile, but was actually super down-to-earth aside from being hot and smelling really good. We already have tentative plans to have a proper date next weekend so looking forward to that.

So life goes on even though I'm still a bit heartsick over J having such a hard time with me being trans. On my walk home I kept thinking of all these things to say to him and I was tearing up. Then I remembered how wonderful being with Josh was and that what we have has the potential to grow into something substantial, and that there are other really nice people who are interested, so things aren't so bad. That said, I still really hope J comes around.

[stephaniec]

it's fun to hear your updates

[mandonlym]

Thanks Stephanie. I'm trying to figure out how to make these threads more helpful but not sure. I guess I kinda wanna show that it's possible to lead a relatively normal even if a bit challenging life post-op. Hopefully they serve that function.