- What's your favorite sexual position?
- Doggy style, from behind.
- I'm gonna go with 21.
21 people have been your little doggy.
(group laughs)
(mysterious music)
- [Interviewer] Who are you?
- I'm Winston.
- [Interviewer] Winston, welcome.
- That's right.
- [Interviewer] So today you're gonna be guessing
how many people each person has slept with.
- Yes.
(group laughs)
- [Interviewer] You nervous at all?
- Yes.
As someone who is not very sexually experienced,
I feel like I might not have a great read.
So I'm gonna try.
- [Interviewer] So everybody gave us their numbers.
And we printed them out and you have to assign them.
- Oh god.
Well right off the bat, I can see I'm gonna be calling
someone a virgin.
So that's fun.
Okay.
21?
(laughs)
35, okay, these keep going up.
No.
(group laughs)
- Is this real?
- [Interviewer] Yeah, it's real.
- Okay
- How's it going man?
- Good, what's your name?
- Cue.
- Can you do like a slow twirl?
- Sure.
- Slower.
(group laughs)
Okay.
I'm gonna try to just base it off of your appearance
and the way you carry yourself.
I see some confidence.
We're making a lot of eye contact.
Maybe you're attracted to me.
I'm not sure.
I don't think you're a virgin.
But your not too high.
I'm gonna give you a three.
Did you choose this outfit?
(group laughs)
- Wow.
(laughs)
- Well, yeah... - Yeah.
- You did? - Yeah.
- Good choice.
- Oh my god, thank you.
- [Interviewer] Did we cover how many people
you've been with from the beginning?
- I have slept with one person.
- [Group] Aww.
- Why is that cute?
(group laughs)
Yeah, I'm gonna give you 30.
- All right.
Why middle of the pack?
- The way you dress kind of implies that you're busy.
I don't know if you have time for 1500 people,
entering you.
(group laughs)
Or you entering them.
- I'm Tom.
- Nice to meet you.
What's your favorite sexual position?
- Doggy style, from behind, me penetrating.
- Yes, okay.
How hard?
- Usually, if that's what's happening, pretty hard.
- God.
I don't think you're the 1500 one.
- Why don't you think I'm the 1500 one?
(group laughs)
- The 1500 person might be someone who could attract anyone.
I think maybe you're someone that would attract
a smaller subset of people.
You're not a virgin,
unless you've been doggy styling your bedpost or something.
(group laughs)
I'm gonna go with 21.
21 people have been your little doggy.
(group laughs)
- Hey.
- Hello.
I think you're a virgin.
(group laughs)
When I was a virgin,
I also stood with my feet out like this.
(group laughs)
And I feel like there's something there.
I have to get info from somewhere, I mean.
- What, do you expect me to stand like this?
- Well now,
(group laughs)
It's like, kinda sexy, so.
Virgin.
There you go.
(group laughs)
- How many tattoos do you have?
- Probably like 16 or 17.
- Okay, you stopped counting.
- Yeah.
- So you're not 1500?
'Cause that person did not stop counting.
(group laughs)
I'm gonna go with 51.
I think you've gotten up there, but you're slowing down now.
- Thanks.
- You make me nervous.
- Why's that?
- 'Cause you're tall and you have nice eyes.
(laughs)
Um...
Yeah, I mean, you've had sex.
I'm gonna go with 60.
- Why 60?
- I just think you're a very attractive person.
I could see you pulling a lot of honeys.
- Alright.
(group laughs)
- You've been standing... - Do you want me to spin?
- Kinda.
- Yeah, okay.
Should I go slow or fast?
Put my arms out.
- Something just popped.
I think your hip.. - Yeah, it's my hip.
(group laughs)
The way you spun, despite the hip popping,
I think you're confident in your sexuality.
So, I give you 35.
- Alright.
- Can I ask what you do?
- I'm in school.
- Okay.
(group laughs)
Apparently, you've slept with 1500 people.
Say this number's true.
Or say it's not true.
Would you be offended if someone told you that
you look like you've had sex with 1500 or more people?
- Kinda, yeah.
- Okay.
- [Interviewer] How did that feel?
- I feel like I just used all of my brain power.
I'm curious to find out how I did.
- [Interviewer] With a raise of hands,
who did Winston get right?
- Oh.
Okay.
I thought I was only gonna get one right.
(group laughs)
I'm just, I'm happy for him.
(group laughs)
What did I originally guess you as?
- Three.
- Okay.
I was a newbie at the time.
- Yeah.
I get it.
Does this surprise you for me?
- Yes.
Do you think you have approached most of the 51?
- I mean, yeah.
A lot of guys shoot the shot at me out here actually.
- It's cause you're cute.
- Thank you.
- Hi Winston.
- 60.
- Mm hmm.
I started when I was about 13,
and I got into kinky stuff when I was about 15.
- What is kinky?
Like not doing your homework,
(group laughs)
and having sex instead?
- God, can you say that slower and more like a teacher?
Did I not do my homework Winston?
(group laughs)
Winston, am I a naughty student?
- I'm scared.
(group laughs)
Holy shit.
(group laughs)
How do you define sex?
- For me, this is every activity I've done with somebody,
with the intent of an orgasm, whether there was one or not.
- Okay, so not always penetrative?
- Correct.
- So you obviously enjoy sex, right?
- Yeah.
- What makes you like it so much?
Is it purely physical?
- For the most part.
For a lot of queer folks and a lot of gay men especially,
sex and love are very removed.
I was having sex long before I fell in love with somebody.
So like to associate love and sex, came much later.
And even still to this day, making love is way more weird
than just like sucking somebodies dick.
- Right.
- Like totally.
- You should write a book.
(group laughs)
So zero?
- Yeah.
- We've all been there.
Do you want to not be there?
- So I'm saving myself.
- For?
- Marriage.
- Marriage, okay.
Have you ever had any doubts about that?
- No, I'm pretty confident about it.
I'm proud to be a virgin for it.
I have no breakups and stuff.
I'm not crying for someone.
And even if I do bad in my sexual life,
there's only one partner who'll complain.
(group laughs)
- 21.
What did I give you?
- 51.
- Okay.
Could you imagine yourself having had sex with 51 people?
- Oh, absolutely.
Yeah.
- So number doesn't really matter to you?
- It used to.
I was raised in a fundamental religion.
I didn't come out until I was 36.
- 36?
- Yeah.
- Are you 30? - Seven.
(laughs)
- Okay.
How many of these have been in the last year?
- Two.
- Only two, okay. - Yeah.
And there was like a period of time
where I did some experimentation.
Both male, female, couples, sex clubs.
- Wow.
- Yeah.
- 30.
- Did I give you 60?
- You gave me 60?
- Have you enjoyed all 30 times?
- No.
(group laughs)
No.
- Are you single right now?
- I am.
- When was the last time you had sex?
- Last week.
- Who was it with?
(group laughs)
- This is wild.
Friends with benefits?
- Yeah, definitely friends with benefits.
- Okay.
- Yeah.
- Hey, it's me again.
- What's your work?
- I'm a dancer.
- Exotically?
- Yes.
- Okay.
Quick question, have any of these 35 people been found
while at your place of employment?
- Yes.
- Yes, okay.
- Yes.
- Are you aiming to increase this number?
- I'm in a relationship and I think
this one, I'm gonna stay with for a long time.
- That's good.
- Yeah, so sex is great.
So shout out to you.
- [Interviewer] Shout out to who?
- Shout out to the boyfriend.
- [Interviewer] You're not even gonna name him?
- Donovan.
(laughs)
(group laughs)
- Nice job Donovan. - Shout out to Donovan.
(laughs)
(drum roll)
- [Interviewer] What's changed in the course
of doing this video?
- Knowing that he's at 1500 plus and the different ways
in which he defines sex is pretty eye opening, I would say.
- [Interviewer] Do you want more sexual partners?
- Well I think this has made me realize that
I'm not shooting for a number.
I'd like more experience.
I think it probably gets easier as you go up.
- [Interviewer] Does everybody agree with that?
- [Group] Yeah.
- It's a rollercoaster.
It's a rollercoaster, there's some highs and some lows.
You learn some things.
You evolve.