We have strengthened our moderation systems and processes to more effectively address illegal content.
Every report is now publicly tracked with its complete resolution history so the community can see exactly how it was handled.
We rely on the Motherless community to keep the platform safe. If you see any violating content, please use the report button.
[View Audit Log] | [June 2026 Update]

Board Posts

6
Anonymous
@confessions
28 Dec 2016 6:20PM
• 975 views • 1 attachment
[ − ] thread [ 3 replies ]

Bombshell, my girlfriend brought up that she wanted to see me get it on with a guy, she has said this drunk before but was legitimately bringing it up again while sober. I have always been a little bi-curious (not attracted to men but watch ladyboy porn etc.) but never really thought of it as something I would really do. So when we talked about it more it led to her joining in, and also having women threesomes as well...wtf!

Needless to say I was pretty excited but honestly I am nervous. Neither of us have ever done this before. Also, it seems she wants a guy and I to "start" and then she will join. Is it worth me having my anal cherry popped for more kinky sex with 2 women to happen in the future or is this just my penis thinking? Also, how the hell do you even get a good fuck buddy/girl? Any advice Motherless?

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
9
Anonymous
@confessions
19 Jul 2014 11:00AM
• 1,761 views • 1 attachment
[ − ] thread [ 5 replies ]

Since my fiance and I broke up, I got really into prostate massage and got some toys to help out. I would sit for hours and watch porn and just slowly milk myself before letting my self cum. I got into a lot of shemale and ladyboy porn in the process and eventually started jerking off to femme bois and some crossdressers as well. I even mail ordered some lingerie to wear while I do it and started to shave my legs since I have a stocking and garter belt fetish. After a while more I wanted more than just toys in my ass. I wanted to have a real life encounter but didn't know how to do it but figured a gay bar was the best bet because I could likely find someone for a casual hook up who I could let fuck me in the ass. But without the lingerie I'm just not as into it and I wasn't sure if I could really do it. I put on a pair of panties, a garterbelt and some stockings under my jeans and went to a gay bar last weekend, but chickened out because I don't know much about gay culture and don't know what they think about crossdressing. I looked at a few guys and wondered what it would be like to suck their dicks but got scared, went home and jerked one out instead. Last night I tried it again and hooked up someone. He didn't seem to mind my stockings. We sucked each others dicks for a little bit, and then I let him fuck me in the ass. It was different than milking myself, but I really liked it. Now I want to do it again, but this time I want to suck more cock and actually swallow someone's load. Some people on here will call me a fag, but whatever, I bet they'd still let me suck their cocks too.

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
4
Anonymous
@confessions
06 May 2016 4:52PM
• 4,573 views • 1 attachment
[ − ] thread [ 15 replies ]

I confess that I have spent pretty much my entire day today while I've been "working" from home, actually researching for my first trip to Thailand later this summer. I'm young, single and have had an obsession with ladyboys for as long as I can remember and can't wait to finally take the plunge. I have been reading up on the various ladyboy bars and also using the escort services. Thinking I will avoid the street hookers. Perhaps make a trip for a couple of days from Bangkok to Pattaya which sounds like a great spot for the beach and ladyboy nightlife. I really want to be a bottom though also want to try sucking ladyboy cock and fucking them in the ass too. So any tips from guys who have gone before for a first timer on this sort of sex vacation such as interactions with the "girls", how I find out if they will fuck my ass, how not to get totally scammed or ripped off? I am booking my flight and hotel later tonight and am already shaking with excitement!

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
-1
Anonymous
@random
13 Sep 2016 12:15AM
• 109 views • 0 attachments
[ − ] thread [ 1 reply ]

You're now chatting with a random stranger. Say hi!
Question to discuss:
Guy with small dick needs a daddy? ;)
Stranger: lol
You: Is this a question or a request.
You: I am sure somewhere a guy with a small dick needs a daddy
Stranger: i think a request
You: That would not explain the question mark
Stranger: idk lol
You: I wish he gave more detail.
Stranger: right
You: I like slender girly guys with small dicks
You: but a fat guy with a small dick would do nothing for me
Stranger: im not into guys but you like what you like
You: Would you fuck a guy if he were really cute?
Stranger: maybe a m to f trans
You: Yes, those can be so hot.
Stranger: sometimes
You: Best $2000 I ever spent was on a ladyboy in Las Vegas
Stranger: lol
You: Gorgeous little tits and an ass that would not quit
Stranger: nice
You: Very feminine but with a cock
Stranger has disconnected.

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
4
Anonymous
@chicks
31 May 2012 5:24AM
• 1,359 views • 4 attachments
[ − ] thread [ 7 replies ]

Check out this ladyboy in my hometown. She posted these photos on Craigslist trying to find a guy or a couple to play with. I emailed her and will hopefully get some more photos and maybe even go fuck her :P

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
3
Highlandfucker
View posts View profile
@confessions
09 Mar 2023 3:18PM
• 402 views • 0 attachments
[ − ] thread [ 4 replies ]

So my confession,
I’ve been in s relationship with my partner for a long time and I love her. But as soon as she’s out the house on holiday, I turn into a little male slut and use the opportunity to do all the nasty things I want to do to myself.
She went on holiday and i used the time to cum in my own face, swallow several of my own loads, i made myself a rice dish with rice cooked in piss. I had a dirty bath (I went for a bath and shat in the water. Sat there with my shit floating next to me).
I whored myself out. A guy payed me £50 to suck him off. I even got fucked by a ladyboy escort!
I love my girlfriend but I also love being a slut! She’s at work tomorrow and I have the house to myself in the morning. I’ve already got the buttplug and lube ready!

More than happy to chat with anyone. Happy to show off as well :D
reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.
2
Anonymous
@confessions
09 Sep 2013 4:38PM
• 2,091 views • 0 attachments
[ − ] thread [ 8 replies ]

I confess I'm a straight guy and have sucked a transexual's dick and they came in my mouth.

I spent over half a year in Thailand within the last 12 months.
Whilst I was there was in a relationship with a white girl, but she wasn't there with me. I went to plenty of bars and thai girls (girls, really.) would be all over me because I'm young and I'm white.

One night I got pretty drunk with some friends and went to a ladyboy bar, I knew they had dicks, but they were pretty hot and had their tits out. One drink led to another and by the end of the night I had 5 of them sucking my dick in the middle of the club, but I suffer from sexual anxiety so I was soft as a wet sock. My 2 mates were watching with their eyes open and we eventually got split up.

I was feeling pretty rough by this point, and a little adventurous so I took one of the 'girls' to a room and bought a condom (they were TINY) and as she was sucking me off I couldn't get it up. She kept asking "aren't you horny? don't you wanna fuck my tight ass?" but I just couldn't do it.

So instead of leaving with my tail between my legs I thought I'd at least try something I'd never done before so I started sucking her off. I used techniques that I've always wanted my gfs in the past to do to me, good hand work, lots of tongue, you know, each to their own, and within maybe 2-3 minutes she shot a load right in my mouth. I wasn't expecting it so soon so I spat it out pretty quickly, she showered, got dressed, and told me to not bother paying because I had already paid her in one way.

What happens in Thailand stays in Thailand, unless it's a ML confession.

And no, I wouldn't do it again, it's not my thing.

reply favorite add to gallery permalink Share
Quote Strike
Anonymous
Anonymous

Attachments are disabled for system maintenance.

note, attachments may take a moment to show up.

Nude Vista Content

Ladyboy Monster Dick Fucks Guy During Massage

06:29 13.5K

Good Try Of Ladyboy Bottom Fuck Guy

05:08 15.6K

Top Ladyboy Fucks Older Guy

06:17 3.5K

Ladyboy Witch Fucks Guy POV

06:08 19.5K

Ladyboy Fucks Guys Ass Roughly

05:30 13.2K

Ladyboy Fucks Guy During Massage

05:46 12.3K

Are you 18 years of age or older?

You must be 18 years or older and agree to our Terms of Service to access and use this website. By clicking ENTER below, you certify that you are 18 years or older and that you accept our Terms of Service.