f0xmail: I Want To Lose My Virginity on Grindr! Help!


I’ve been stalking your blog for about 2 years now but I never comment, but I love your blog and the advice you give so now it’s time for me to ask for some advice for my self.

Some background about me, I am 18 years old and I live in London and I am attracted to females and males so I guess I’m bi and I guess I’m DL because nobody knows about it, but right now I’m thinking of experimenting. I’ve been curious for a long time but now, I’ve had sex with a girl and I’ve watched gay porn since like a few months ago and I like it but bare in mind that I’ve been curious for a very long time, like probably since 13 years old. However, now, I want to take my curiosity to the next level…

I want to try sex with a man.

Recently, I downloaded Grindr ( I know, bad move) but it’s seemingly the only place to find someone who wants to get down and where I live I’m sure there are gays but the girls come out more than boys. It is interesting to see who uses it though because I’m seeing people who you wouldn’t think are gay and I’ve actually chatted to one – he told me he was “straight-acting” , but was out to his boys, i just found that interesting, like you know those type of gays are around but not until you actually see it for yourself, its fascinating. Anyway, I am aware of how bad that app can get, I don’t trust anyone on there, I don’t act a fool and stupidly send pics to everyone, like I don’t know if I could be talking to the killer so I’m very conscious about who I’m talking to, but obviously you never know because people are very good actors.

I’ve got the usual DL worries, I’m scared that someone will see my messages or this guy I’m currently talking to will tell other people about me, at this time of writing, we have not exchanged face pics but we have described ourselves to each other and I like the sound of him, there is a spark. But, I‘m scared that I may be going in too fast and acting like I’m ready when I’m not, you know? It’s annoying because me being ready fluctuates – sometimes I am and I feel to try the dick and sometimes I’m like maybe not now.

As slightly previously mentioned , I’ve met this one guy on Grindr and we seem to be clicking, we’ve moved from Grindr to iMessage and I’m literally talking to him as I type this and (UPDATE) – he’s just given me a time frame of 9 days to “get some”, as he mentioned that his “head game was crazy”, and I said that “I want some of that” – messy I know.

So basically Jamari, my questions to you are:

1) Do I continue using Grindr to explore my curiousity (in terms of having gay sex), becasue the main thing I want to try is sex with a guy
2) Any tips with using an app like Grindr?
3) Am I rushing into things, I only started using Grindr however at times I feel like 100% ready then at times my confidence comes all the way back down and I don’t feel ready at all
4) Any tips to prepare for sex with a guy?

I’m sorry if this seems long and messy but I am hoping for your advice really soon, I am a fan and I love your work on here. Congratulations on your recent job position by the way, it’s nice too see your growth on here and how you broadcast it.

Help me, Jamari!


first off:

2 years in the shadows!
i appreciate the love tremendously.
thank you for being a loyal foxholer.
thank you for the well wishes on the job.
can you believe it’s been a whole month already?

ya know,
i lost my virginity to someone off a chat site.
a random.
he was fine af tho.
he worked in the government (or so he told me).
i had just got let go from a job and was feeling vulnerable.
i violated on my aunt’s bed.
i know.
long story.
all i remember is:

“this needs to be done before she gets home.”
“this fuckin’ hurts!”

i didn’t even do it all the way.
i refused to let him bang me like he was trying too.
my first time was “eh”.
i got pounded ferociously later on by another wolf.
did he fuck my brains out.
another long story.
at the time,
i was also on the dl.
i was scared,
but i was also horny and wanted to lose my virginity to a wolf.
star fox (rip) was out there fuckin,
but i was being father joseph.
my main thoughts was similar to yours.
getting on the site,
i didn’t want to put my face due to “who will see me??”.
i stayed on private,
and when i trusted the wolf,
i unlocked my pictures for him.
those days are long gone.
everyone is on chat sites looking for their next hook up.
they love to know they will be taking a fresh virginity too.
i’ve never been on grindr.
i know jack’d tho.
i’m sure it’s the same story.
i’d say:

take your time

you want to fuck.
 porn making sex look glamorous.
if you are dl,
your vetting process needs to be much more careful.
you could be talking to anyone.
hyenas and jackals put pictures up of attentionistos.
many aren’t who they say they are.
as a dl,
no one should be giving you a time limit either.
you have to be careful as those sites have a lot of trash on them.
your “flip flopping” is due to nerves.
it’s okay!
we have all been there.
it is a big deal to lose your virginity.
we aren’t vixens in wanting it to be “special”,
but we should always be making sure we are safe.
if you aren’t ready,
don’t do anything you aren’t comfortable doing.
i was lucky to meet someone who was patient,
knowing that i was a virgin.
we never spoke again after he took it,
but i was already talking to new wolves.
so my advice if you want to go the “chat site” route:

a) take your time in vetting out potential candidates
b) get evidence it’s really “them” on the other side
c) set up a google voice so they don’t have your real number
d) always meet in a public place
e) never bring anyone to your home or go to theirs
f) if you’re old enough to fuck; you’re old enough to get a hotel
g) ( x follow this foxhole guide to prepare for sex )
h) condoms, condoms, CONDOMS!

…but you are 18.
as cliche as it sounds,
you have a whole life ahead of you to have sex.
i don’t trust chat sites anymore after all the news about them.
it’s the one of the only ways to meet “us” nowadays.
college might be better.
you’ll be around others who are curious as you are.
whatever route you choose foxholer,
please be careful out here.
if your spirit isn’t sure; listen.
keep me posted!


lowkey: my safety,
along with my pleasure,
cums first.
i don’t give a fuck about some pineapple and his raging hormones.

7 thoughts on “f0xmail: I Want To Lose My Virginity on Grindr! Help!

  1. I want to talk about your comment about porn making sex look glamorous and its nothing like that in real life. I mean it can be fun and amazing like that but real life its legit a lot of things going on inside and out. I remember sneaking around and thankfully nothing happened but the way things are be extra careful of exposers, flakes, crazies and the weirdos. Like take your time on losing it tbh.

  2. Aw I remember being 18.. (I’m 20 now). Back then I was already hooking up with big muscular guys lol. I started pretty early.. (with girls&guys). I lost my V at the same age that I started masturbating which was 14. I know, bad. I was a really curious teen so don’t follow me young man. By that age I was already about 6’2 so I easily passed for an 18 year old so it wasn’t that difficult for me to get laid. Plus girls threw themselves at me back when I was in school so losing my virginity wasn’t a challenge on both sides. It was just something that happened I guess.. Initially I wanted it to be with “somebody special” but that wasn’t the case. Funny enough all the people who I’ve had my first sexual experiences with have called me after that to meet again but back then I felt uncomfortable so I never did. The first guy who topped me even told me that he loved me and dude has contacted me for years after that trying to get back with me. One thing I wish I told myself back then was DON’T let anybody make you feel pressured into doing ANYTHING that you DON’T want to do! Saying no is OK.

  3. Jamari, your advice to that young man was absolutely beautiful, Well said, my friend. However, how the hell do you meet curious or dl guys in college, especially the athletes? It seems so damn difficult to even suspect it, muster up enough courage to start a conversation, and then go in for the kill. It’s crazy just thinking about it. What are the signs to know a guy is checking you out? I’m going bananas right now ’cause I’m attracted to this Latino dude in my class and I think he low-key stares at me.

    1. ^thnak you rr!

      wolves with some kind of “power” over others pick you.
      you don’t pick them.
      if you catch his radar,
      he will stare because he is attracted to you.
      he is also trying to decipher if you’re gonna be messy.

      if he’s someone you want,
      but you can’t have,
      simply ignore him.
      ignoring is a powerful tool.
      it lets him know that he needs to come to you,
      rather than you going to him.
      it starts the chase because let’s face it,
      wolves love the hunt.

      hope that helps!

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