Jizz

My boy[f]riend said I was too shy to do this

gonewild

skinny shy college boy

manlove, MaverickMales

I'm a bit shy, but my boy[f]riend encouraged me to post this here.

GoneWildPlus

Average ger[m]an skinny boy. Im kind of shy, convince me to post more.

ladybonersgw

I have started hanging out with a boy recently and watching movies. I desperately want him to kiss me.. But he is shy. How should i go about earning his a(f)fections? Apologise for poor quality <3

gonewild

I'm a little shy...can reddit make me [f]eel better? (Request from boy in math)

gonewild

I'm still a little shy. :( Sorry boys I like girls ;) [f]

gonewild

I'm 19 today, what do the gals and guys here think of this shy birthday boy?

ladybonersgw

Any love for this shy Mexican boy?

ladybonersgw

(F)eeling shy. But I've got a whole album waiting for you dirty boys. I'll need some likes first :)

gonewild

This subreddit has helped me get over me being shy and a bigger guy. Thanks boys.

gaybears

I'm not shy. My boy[f]riend didn't break up with me, and I don't need a self esteem boost. Frankly, I just want to share this lingerie with you.

gonewild

Any love for a shy college boy? Pms welcome!

ladybonersgw

If shaggy-headed beach boys is your thing, don't be shy.

ladybonersgw

I'm shy, but boys tell me I'm pretty and I have big boobs. Here's a tease.

GoneMild

By request, freshly flogged and fucked. You boys and girls wanted to see my full face. And the obligatory bra/cleavage. Comments and PMs get me off, don't be shy!

GoneWildPlus

Hi Reddit! Posted before but got shy because I wasn;t received well ;( Maybe this will be better? PM me boys AND GIRLS :)

gonewild, GoneMild

[F]irst post from work, also going to start gendertagging posts, so you boys and girls who are gun shy know that I have tits, not a dick. Comments and PMs are awesome, I respond to the good ones, try to be clever. ;)

GoneWildPlus

the boys and the Chief fresh out the wrapper. I hope you like what you see :) If you would like to see more, all suggestions are answered with private PMs of the act so don't be shy :P

Balls, penis

my boy[f]riend told me to stop being shy, so hi everyone!

gonewild

Hey! Disabled Little boy right here. Are there any other disabled Littles around here? I am super shy but it seems that I will be accepted here even though I am pretty much mute.

littlespace

Why are straight boys always so shy?

Scally

Hey boys, I dont post much here. I'm a bit shy ???

GuysFromBehind

I know it's not exactly GW, but I wore this out last night trying to impress all of the shy, skinny, artistic, nerdy boys

AsiansGoneWild

eastcoast shy little girly boy want to get to know someone

sissypersonals

Still a shy big boy

ChubbyDudes

Kinda Shy Korean Boy

GaybrosGoneWild

24yo boy toy came over this morning before a busy day. Shy at first but he is starting to embrace. Sent this to husband at work :)

Cuckold

If you like shy + skinny boys

ladybonersgw

She goes wild when sucking a 19 y.o delicious cock! Nothing gets her cunt wetter than a horny slim, shy, smooth boy!

Hotwife, GWCouples

Don't be shy baby! Show everyone if you've been a good boy today!

diaperpics

A once shy and timid Asian boy after three months of female hormone therapy

traps

“You heard me, white boy. Don’t be shy now. Spread your legs like your girlfriend and beg me to fuck that pussy.”

straightturnedgay, ManSex, GayBBC, BBCsissies, MaleCall_LegsUp, BlackOwnedSissies, u_oubilette2

Don't be shy, You Know you wanna eat these Groceries Boy! (Link in Comments)

AssholeBehindThong

Showing the shy ‘straight’ boy that the only place as a sissy bitch is under my foot with a dick in his ass.

straightturnedgay, StraightToSissy, Sissy_humiliation, sissycaptions, Sissies, u_exoticpeache, u_ArabExplorer, u_ExoticEngineer564, u_Perusing-your-wears

“Drop the shy straight guy act. You said you wanted to try being my slave, so do it. Go ahead boy, worship me.”

straightturnedgay, submissivemen, GayKink

Teaching the cute shy straight boy how to spread his legs and use his new pussy.

straightturnedgay, BBCsissies, BlackOwnedSissies, GayBBC, BBCSluts, gaynsfw

“Bro, we both know you liked it. No need to play shy anymore. Be a good boy and go bend over the garage table. I’ll be out once your mom leaves.”

straightturnedgay, jockstraps

Don't be shy, be a good boy and send your whole paycheck to me.

u_Ambergoeswild, findommistress, cashslaves, FinsubTeamwork, dommes, findom, Findom_Elite, skintimate

Yoga boy's Not Shy

AsianGuysNSFW

“That’s a good boy. You’re already down there... Don’t be shy now… Pull them down and give it a kiss.”

straightturnedgay

You started off as a shy ‘straight’ boy. Now he’s got it so you’ll do anything to keep him happy.

straightturnedgay