I just accidentally slept with a ladyboy

[BelowAverage]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

 

[Johan]

dnr

 

[green_fn_2033]

gay nigga

 

[beniman]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

 

[hej1377]

am 100% straight,

I blew...her

 

[javen1384]

Jeet advantures in pattaya

 

[Laqi]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

GAY ASS NIGGA

 

[BelowAverage]

GAY ASS NIGGA

Ladybody sucked me first cancels out any gayness

 

[Laqi]

Ladybody sucked me first cancels out any gayness

Did you suck her?

 

[BelowAverage]

Did you suck her?

Ofc favour needs to be returned not gay tho

 

[bourgeoizyzz]

For contextual purposes: I am 100% straight

Not anymore, nigga

 

[IliaTopuria]

 

[BelowAverage]

Not anymore, nigga

Sucking off another man is the purest form of masculinity

 

[bourgeoizyzz]

Sucking off another man is the purest form of masculinity

Standard looksmax.org belief

 

[throwaway2]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

@MaxillaSlayer ts you?

 

[BelowAverage]

Standard looksmax.org belief

Half of the faggots here would suck gandy off just for a small part of his dna

 

[Panchitosbroncs]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

dnr but u're a gay niggerrrrr

 

[bourgeoizyzz]

Half of the faggots here would suck gandy off just for a small part of his dna

Half the faggot here would suck off the dude in an "are they looksmatched?" thread

 

[MaxillaSlayer]

@MaxillaSlayer ts you?

What the actual fuck, I don’t ladyboyMaxx tho

 

[throwaway2]

What the actual fuck, I don’t ladyboyMaxx tho

yes we do

 

[iblamexyz]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

@RealSurgerymax type of experience

 

[nestivv]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

 

[cloak]

NIGGA BLEW HIM

 

[rj_0616]

I am 100% straight

I did find something exciting with ladyboy porn

its legal now bhai

 

[Cash💸]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

Fag

 

[MaxillaSlayer]

yes we do

Yeah I know bro, I’m sorry I lied, WE ladyboymaxx

 

[enlightful]

Stopped reading after the title

 

[narcissuscurrycel]

there are no accidents

 

[Instagram]

Ladybody sucked me first cancels out any gayness

keep coping you utter faggot

 

[michael skelton]

For contextual purposes: I am 100% straight, very comfortable with my sexuality and up until now thought that sleeping with a ladyboy required someone to be gay. I would never kiss a guy and the idea just seems unfathomable to me. My brain is just not wired to like men. Having said that, I did find something exciting with ladyboy porn, specifically ladyboys with real women. I'm not desperate for sex and am very comfortable around women. I've had many fantastic relationships.

I was travelling through South East Asia and met a girl online. She was really cute, and I was wary that someone could be a ladyboy in this region, but she seemed to check out. We arranged to have dinner.

When I first saw her in real life, I did suddenly think...hmm what if she was a man. She did have slightly chiselled features and a husky voice. She said she had a cough, thus the voice.

We had a great dinner and lots of chemistry. She told me about her ex boyfriend and generally about her life. To make sure she wasn't a ladyboy I gave her a recount of how my friend hooked up with a ladyboy by accident in Asia, and she seemed shocked. I asked more directly and she was offended I was asking the question, so I played it off as a joke. All seems to check out...

We had a kiss then hit the clubs and had a good night out. The next morning she came over to my hotel. I was still tipsy. We were making out on my bed. I had some warning signals where she wanted to be on top a lot and go down on me, but really shy when I tried to finger her. Previously she said "I hate being fingered", so I thought ok maybe she really dislikes it.

Then she said "do you want to fuck my arse". ... Now, I love anal with girls, but girls never really suggest that straight off the bat. I was more confrontational and said "did you use to be a boy". She finally admitted "yes".

I was very confused. I was attracted to her physically, as a woman. But she had a penis. Awkward boner alert.

I'd like to say that I stopped there and ended things, but ... somehow we got into it. I blew...her? And fucked her. Twice. I couldn't quite comprehend why I was so aroused by the juxtaposition of being attracted to the female side, but not being completely turned off by the something extra.

I was visibly shaken after and she asked if she should leave, to which I apologised profusely and said yes.

This has made me question the construct of gender and sexuality. If we define gender by genitalia, then I should not have been attracted to her, as again, I wouldn't even kiss a 'man', no matter how effeminate. She was effectively a girl from a young age, and lived life as a female. I was attracted to that.

Yur just gay

 

[aidenltn17]

How the fuck was this an accident besides not knowing she was a ladyboy when you met. You’re gay

 

[Coolman788]

This was not an accident bro