I'm a 24 old male student, mostly straight but wanting to try new stuff.
I answered to an announcement on internet about a 58 y.o. man looking for a young boy to do some roleplay: I'm gonna dress up as a secretary and he's gonna be the boss. Then of course we will start playing.
We are going to meet tonight at his home's and I'm really excited about it. Never did crossdressing before but the idea of doing it together with the roleplay really makes me horny.
any perspective on this?
>>6268634
Well, I'm surprised 24 counts as a young boy to him...
>>6268878
He was looking for an under 30
>mostly straight
not anymore you ain't
>>6268893
Yeah I get what you mean but I keep being attracted to girls. I already had a gay experience (a man gave me head) but I couldn't even get hard lol
The thing which really turn me on is dressing up as a woman and then be touched and licked as he said, I don't really feel attracted by male's body.. it's more a narcissistic/exhibitionist stuff
>>6268684
I'll give you my weird perspective/experience with this:
>start meeting up with older divorced guy (psychologist, not mine) at his house
>when we have sex it's always in his daughter's room. just figure he doesn't want sweat/cum on his regular bed. Daughter is away at college.
>one day after he's fucked me we're laying there talking about fetishes
>he admits to me that he's always fantasized about fucking his daughter. that's why we use her bed since he can smell her in there
>kind of weirded out, but whatever
>one day he asks if I'd wear her panties. I'm OK with that
>do this for a few weeks
>his daughter comes home to visit and leaves a bunch of her clothes there for dad to wash (how considerate)
>he asks me to dress in them when we have sex. panties, bra, dress
>he is an absolute mad man that night. fucks me harder than ever
>starts to become a routine. when I go over there I immediately have to change into her clothes
>he even buys me a wig that looks like her hair style
>can't imagine what's going through his mind as he plows me while I'm dressed in his daughter's clothes
>>6268634
>>be 7
>>had a few friends that were girls
>>trying on their clothes and they do my makeup
>>their parents catch us, and tell my dad
>>get yelled at for 2 hours
>>6269004
woah that's crazy.
I'm not sure I will go anymore. We're messaging via mail and this man is seriously creepy. He looks creepy from his pictures too.
Fuck this, I think I'll stick to chicks.
>>6268901
>The thing which really turn me on is dressing up as a woman and then be touched and licked as he said, I don't really feel attracted by male's body
You're not gay, you have a submissive fetish. There are women out there who'll fuck you.
>>6270472
OP here. As I said in the post above, I don't think I'm going to the meeting. The thing is really creeping me out and I think you gave me a correct description of what's going on in my mind.
>>6269004
hot
>>6268634
take it slow, remember what you wanted, ask for money after to get home GG
>>6270584
He explicitly said he didn't want to pay for this. I also told him to stay clothed while I was naked and he agreed on that, so that would even be safe. I think anyway that this fantasy would be better realized with a woman tho
>>6270402
I think you should just be smarter about this in the future. Maybe you're bisexual with a kink for crossdressing and stuff. Not a big deal. Just be a little smarter going forward. Don't try to bang ugly old guys, find a nice well adjusted man closer to age range whose willing to dominate the hell out of you. They exist and will satisfy you much more than some soft old fart whose so deep in the closet he's found lingerie to throw on his boy toys.
>>6272528
This guy knows what's going on
