How would you feel about losing your virginity with your best friend crossdressing?

I don't think having gay sex counts as losing your virginity

Dick gotta go inside that pussy know I'm sayin?

Dude, I don't even know anymore.

>>82208981 (OP)
my best friend doesnt look like that doe

That son of a bitch looks like a linebacker

why would i want to have sex with my best friend? why are lgbtqia2+ers so disgusting

>>82209523
he does. one can only hope he's dressing up like that because he lost a bet during football practice

>>82209523
He is a girl to me, even though it is a man it is still a girl to me

>>82208981 (OP)
If that's a guy he's hot

>>82209720
What if it's just a girl with wide shoulders

>>82209760
It's a guy though

>>82209868
MY COCK IS GOING ABSOLUTELY FUCKING WILD

>>82209868
How is that a guy if they look like a girl?

>>82209868
I'm still not convinced

>>82209942
he looks like a guy in a dress with a girly face

>>82208981 (OP)
id pry kill myself because thats really fucking gay and disgusting

I think losing your virginity should be done with someone you love who loves you and who you are going to have a lifelong relationship with

>>82208981 (OP)
>>82209868
Does she have any where she isn't anglemaxxing? The OP image accentuates legs/hips/thighs and tricks the viewer into perceiving the shoulders/chest/head as smaller. The second image is massively downplaying shoulder width, and you can see her head is definitely also strategically placed to help with hiding the adams apple.
I'm open to the idea of finding a trans girl hot or whatever, but these images are very dishonest.

>>82211187
https://www.reddit.com/r/crossdressing/comments/1mhf2lz/i_think_this_is_my_favourite_look_ive_ever_done/

>>82211220
The full body ones do honestly show off the rather large size of her, but overall definitely top 1% trans girl.

>>82211220
He kind of looks like sydney sweeney

>>82208981 (OP)
do I peg him because he's now the woman or is it regular PIV

>>82211340
Had to look up who that was. Absolutely mid compared to OP's pic

>>82208981 (OP)
I'm 100% straight but why do women legs and feet do nothing for me, but tranny, crossdressser and femboy feet and legs make me hard instantly?

>>82208981 (OP)
This dude has wider shoulders than me after training for 2 years. FUCK it's over.

>>82208981 (OP)
Is it gay if I want his feet on my face and have him jerk me off with his feet?

>>82212656
why the fuck do you insufferable people always have to put some disclaimer about your sexuality. you're likely fucking around but so many people make this disclaimer with complete seriousness. no one gives a shit

>>82208981 (OP)
it's depressing when you start to think about it. the illusion breaks and you realize that you are just fucking some guy who is dressed up like a woman in the ass. it's not real -- it's like eating a tofu burger. cheap imitation of something more desirable.

>>82212656
This is true, my preference is for boy feet

>>82208981 (OP)
my friends are all fat and ugly

>>82209868
it's weird how this guy actually looks pretty good at the right angles but then looks like a total linebacker in other photos.

>>82208981 (OP)
I don't have any friends thoughever.

>>82215142
ok imagine that guy in op is your friend and you one day come across these photos of him

>>82213151
No, perfectly straight.

>>82208981 (OP)
>le AGP smile

>>82208981 (OP)
>>82211220
just looked up his profile and he has a wife
wow

>>82216463
I mean yeah he's tall and manly girls love that shit

>>82216463
Yeah women are disgusting man-hating dykes who hate anything masculine so that's to be expected.

>>82216575
he identifies as genderfluid and plans to start hrt, so she isnt with him because of manliness

>>82216727
What pussy does to a mf. I think incels have more reason to make fun of sex-havers than the other way around.

>>82216463
is that surprising? that he has a wife?

Lots of girls are strangely into the whole crossdressing thing. I didn't think it would be true but I know from experience.

>>82208981 (OP)
I wouldnt touch a tranny with a 10 footpole. That nasaly post pubecent they bullied for shatters any sort of lie their trying to dress themselves as.

>>82216727
>so she isnt with him because of manliness
I mean I'm sure that with his body she married him before she knew about his crossdressing ways

>>82216932
but she stayed with him afterwards

>>82216994
some girls like that sort of thing. like I have a similar body to this guy with MUCH nicer legs though, tall and obviously male but I like crossdressing as well.

my gf knew about it before we started dating, and even encouraged it by giving me her old clothes and she picked my girl name too

>>82217066
are you on hormones?

>>82217125
no and I won't ever do that.

>>82217152
I give it 1 year before you start HRT, egg.

>>82217184
yeah? we making a bet here?

>>82217066
>spoiler
I'm a leg guy myself so props if you do actually have some nice ones.

>>82217152
thats what they all say
good luck on your transition girl :)

>>82217245
I think so! I really like this guys style a lot but his legs are a bit distracting and he likes to feature them hah
>>82217254
ok? is your pic, which is obviously fetish material, supposed to encourage me to become trans like you are?

>>82217323
Are you smoother than his? Slimmer?

>>82209147
it makes more sense. virginity is maidenhood, men don't have it, it only make sense if you pretend to be a woman.

>>82217338
slimmer and smoother. apparently I have perfect girl legs, which is if you stand with your legs together, you should have a thigh gap, a gap by your knees and a gap by your ankles, according to my gf's bestie, which you know is a top notch source

>>82217396
Ugh that sounds really hot. You're making me want to thrust my cock between them so I appreciate you describing them.

>>82208981 (OP)
wait are both of us crossdressing, or just me?

>>82217323
i am not trans, and you are the one who like to present as a girl

>>82217501
no just him

>>82217468
I used to post pics but last time I did I got banned INSTANTLY like fuck wasn't even 5mins.

but I do get lots of compliments on my legs although I've never met a guy with such a leg fetish before!

>>82217511
>and you are the one who like to present as a girl
This is true, anon. why are you so invested in if I take girl pills? you know I'll never meet you, you have no stake in it!

>>82217590
Oh it's no worries anon. I wasn't trying to get you to post pics. Honestly your description was a nice tease to get my cock hard
>although I've never met a guy with such a leg fetish before!
You can thank my high school English teacher for that. Taller woman with shapely, smooth legs and a rack to die for. A lot of the guys had a thing for her but her legs caught my attention.

>>82217590
>you know I'll never meet you,
I just met you right now, Online and Real Life, it's all the same. It's an abomination for you to be as a woman when you are not

>>82217590
>This is true, anon. why are you so invested in if I take girl pills? you know I'll never meet you, you have no stake in it!
because its better if you take them as early as you can

>>82217613
ooo yes it's weird how much our teen years impact our sexuality...during high school spirit week we had a genderbender day, and my gf at the time convinced me to dress up as a cheerleader...the reception I got was overwhelming positive and the compliments fried my brain I think!

anyways it does feel good to be lusted after openly. I didn't have any truly hot teachers though, kind of sad.

>>82217620
>Online and Real Life, it's all the same
not remotely true

>>82217678
better for what? again I won't ever meet you, why do you care!

>>82217692
>better for what?
you will look more feminine if you start earlier
>again I won't ever meet you, why do you care!
i just want to make your happier nona

>>82217707
>you will look more feminine if you start earlier
hmm wow a magic girl pill, incredible. are there any downsides to this??
>i just want to make your happier nona
bit presumptuous of you

>>82217692
>and my gf at the time convinced me to dress up as a cheerleader...the reception I got was overwhelming positive and the compliments fried my brain I think!
Oh that sounds like so much fun. I'm glad you had such a positive experience. It's funny how something as innocent as dressing up as the opposite gender and receiving positive affirmations can have a huge impact later on down the line.
>anyways it does feel good to be lusted after openly.
I'm a bit more expressive since I haven't had a release in a couple of weeks so that's why. Honestly all this talk is probably going to get me to go and blow some ropes tonight.

>>82217782
>It's funny how something as innocent as dressing up as the opposite gender and receiving positive affirmations can have a huge impact later on down the line.
Right? thought it was just silly fun at first, and she was hot so it was for her to tempt a horny high schooler into doing, well anything lol. Even though it was genderbend day and plenty of other students did wacky outfits, we went all out: I let her shave my legs, do makeup, paint my nails, panties the whole 9 yards. I don't think I've ever been as nervous as I was going into school that day LOL fun though

>I'm a bit more expressive since I haven't had a release in a couple of weeks so that's why.
hmm you saving up for any particular reason?? no fap or something? a bit of horny talk is good for you!

>>82217830
>we went all out: I let her shave my legs, do makeup, paint my nails, panties the whole 9 yards. I don't think I've ever been as nervous as I was going into school that day LOL fun though
Man, I wish our school had something fun like that. We were always LAME lol I really am glad you had a nice experience though. You sound like such a sweetheart.
>hmm you saving up for any particular reason?? no fap or something?
Nah nothing like that. I had family visiting this past week and the week before I was sick with a cold for about four days so I'm pretty pent up.

>>82217904
>Man, I wish our school had something fun like that.
yeah the entire spirit week was just all sorts of wacky fun stuff, and there'd be way less schoolwork so it was fun. why was your school so lame though?!!
>You sound like such a sweetheart.
anon ahhh!! thank you, making me blush though! again...after your previous comments about my legs!
>Nah nothing like that. I had family visiting this past week and the week before I was sick with a cold for about four days so I'm pretty pent up.
well I'm glad you're better~ and hopefully you had a good time with family, even if you had to get a little pent up in the process! you could always drop a discord too, if you wanted...because I've got to run for an hour or two

>>82217981
>why was your school so lame though?!!
They had events and things but the staff and students never really seemed all that into it.
>>82217981
>spoiler
Unfortunately I don't use that but maybe I'll catch you around sometime? In the meantime though, I'll be thinking of you and how much I'd love to cum all over your beautiful, smooth legs

>all these responses
got DAMN arcanine is hilarious when they're not trying to be