Experimenting sexually

Does anyone here have stories about experimenting sexually and if you regret it? Specifically hooking up with the same sex. Or stories about trying it out, deciding it's not for you, but being okay with it?

I have a crossdressing fetish and have considered hooking up with a guy while doing it. But there aren't many guys I ever see where I'm like "hey that person looks sexually appealing," I'm always attracted to women.

Should I try it before it's too late or am I always going to be scarred by it?

Attached: IMG_5784.jpg (2100x3150, 269K)

I've only browsed /b/ and Jow Forums for 5 years and I've read enough gay hookup regret threads to fill a couple magazines

I take life advice exclusively from Jow Forums and /b/. you should see my basement.

I'd love to
But seriously I would suggest avoiding gay anonymous hookups, if you're going to experiment then know your partner. Or else you might catch some weird shit or find out mid-pummeling that you don't like being a fucktoy

yes. know your partner and be careful of stds.

that last part sounds hot though
>find out mid-pummeling that you don't like being a fucktoy

Yeah that would be a challenge. I mean, I can get to know someone over a period of time through a website, but going out and cruising the local gay bars is going to guarantee I run into someone I know. And then it wouldn't be me seeing how I feel, now a disaster in my life.

I personally have no regrets with my experiments in bdsm. I've read plenty of sissy/trap regret threads from Jow Forums though.

I guess I'll keep checking Jow Forums.

Assuming I decide this is a bad idea then, how do I permanently shake the crossdressing and sissy porn thing? I've been jerking off to the idea of being the woman for way too long now, and have even looked at hookup site for this kind of thing for almost 10 years now.

If I'm not gonna do it, I need to go about my life normally.

How did you find a partner for your experiments? Asking for a friend, obviously.

Attached: 1456616285682.jpg (512x349, 44K)

I have all sorts of experiences hooking up with members of the same sex while also enjoying regular sex with members of the opposite sex.

The only thing I regret was not being more of a complete asshole in high school and college, saying FUCK YOU to all of the haters, and doing what the fuck I want with my body.

I have a deep sense of loathing that I allowed the pressure of my family, my church, and my society to make me feel less than human because of my preferences. Fuck those people. I wish I could go back in time and suck dick in front of them just to fuck with em.

Get AIDS

Lmao wtf I just had one earlier. I was too horny and decided to fucking experiment inserting something inside my pussy. I saw a toothbrush and decided to use its bottom. I saw that there is some kind of tiny edgy part of the bottom but decided to continue anyway. As I was masturbating on an increasing speed, I felt kinda weird. I pulled it out and I saw blood. Blood. 17-year-old virgin me panicked and adrenaline just rushed fuckingfnajdhjsnjdjsb hell. It was just small blood but I was too scared. I don't want to masturbate anymore ;-;

Idk, around. I have a social life and it includes girls.

Probly broke your hymen. Lel@taking your own virginity with a toothbrush.

Most of my friends would be shocked but supportive if I were to “come out.”

My parents, I don’t know.

I’m just concerned I’m going to feel violated as all hell at the end of this, especially because the guys I’ve met online in the process of thinking about this have been creepy as fuck. I mean, I don’t know what else I should be expecting but everything jumps from “let’s experiment” to “come be my live in sissy maid and take hormones and live your life as a woman.”

One dude even tried to blackmail me.

I am straight but tried to hook up with a gay guy once. We just traded blow jobs and jerked eachother off. I wasn't even able to cum, but I made him cum.

I retrospect, not something I'd do again. Is cock was small and uncut, which kinda weirded me out.

I discovered that I'm bi around 12 years old. My best friend ended up topping me for the next year or more. Got a boyfriend in high school and switched off, although he was more of a bottom. I've had some mind-blowing sex with him, and we've been fucking on-and-off ever since (about 13 years).

That said, I've had many hookups as well and very rarely have I enjoyed them. However, this could be a result of being the bottom. Almost every single hookup partner I've had will promise to stay the night, go multiple times, ensure we both finish, and cuddle a bit. What actually happens is he will strip within seconds of arriving, pump me until he cums, then promptly get dressed and hit the front door before I even have time to get back up on two feet.

I would certainly advise trying it out, but be extremely selective of who you do it with or you're setting yourself up for a disappointing first experience. You can generally tell how committed the other guy will be to making sure you have a good time too in the preliminary conversation just by how forward he is. Also, if he is demanding pic after pic after pic of you without offering any of his own, then move it on down the road.

That's kinda what I want though... the idea of being cuddled and relationshippy doesn't fit with my narrative.

Do I want him to just use me as a four minute fleshlight? No... but the idea of looking for any kind of love here sounds uncomfortable. I don't want to make myself unsafe either though.

I don't know if you're still around to reply... but evening bump too.

> be eternal virgin 24 yo
> Get my first smartphone
> Try out grindr
> Lose my virginity
> Find a boyfriend
The end.

> taking sexual advice from Jow Forums
You'll either get bitter stories of deep regret or borderline erotica roleplay, both of which are much likely pure fiction.
Either venture into the new and unexplored or don't. That's a decision you have to make. There's no middle ground and there are countless ends, good and bad, for both ways.
Stasis or change, what would be better for you? Strangers on the internet cannot tell you this.

I honestly think I'm almost hoping for bitter stories of regret. The lucid, sober, not-horny me imagines me awkwardly sitting in some pudgy old guy's apartment while I uncomfortably apply makeup and he tries to convince me to wear diapers.

The part of me that hasn't jerked off in a week and has had eight drinks imagines looking like Taylor Swift and sucking a dick while going through sissy hookup sites.

You're actually into this "sissy" shit? Well bad for you. I suppose if you wanted conventional sex it would be easier, but if you're going into weird fetishes, you should expect weirdness from it. And yes, pretending to be a girl to get off is weird shit.

"Sissy" shit isn't the right specific thing I'm into, like I don't like the weird lolita style dresses or whatever. But I am into BDSM and being dressed like a girl, so I don't really know where to find an intersection of it.

I'm aware it's weird shit. Like I said in the OP, I don't really find men conventionally attractive. I'm more attracted to the idea of being a girl, but not in the sense that I think I was born in the wrong body or anything. Just that if you gave me the chance to press a button and switch, I probably would.

You probably need a psychologist more, to deal with that borderline dysphoria there.

Yeah, I don't think I could ever face a therapist talking about it. I already have one that I talk to about work stuff, but I've kept this closed off. I don't think she's equipped to help me with this.

Unfortunately I can't justify the cost of paying someone to talk to me about who I do or don't want to fuck.

Enjoy your aids faggot

If I were to guess things about you, the first would be that you spend too much time on the internet.

Eh...

I’m a straight dude.
My best friend is a gay chick, I’d hangout at gay bars a lot.
I’m kind of a natural flirt, especially when I’m drunk.
One day I just got drunk and made out with a guy, because why not... felt pretty meh. More empty than even my shittiest kiss with a chick. Did it a few more times when drunk as heck after that, always the same shit.

Unrelatedly I’ve actually talked with a few different gay friendsabout how they figured out they were gay, often their straight experiences sound about as empty and non-exciting as my own dabbling in the homosexual ones.

Makes sense to me, so no curiosity or interest for more. No regrets either, just is what it is.

Underage b&. Lucky I'm on mobile and can't report.

Yes. Made a thread about it last night.

Lmao. You're gay. Just in Denial.

Tip: straight guys don't just make out with other guys you fucking fag