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thebearwannabe

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thebearwannabe posts

Posts: 537 Files: 4245
thebearwannabe post Had some fun with the husband over the weekend and we though..

Had some fun with the husband over the weekend and we though..

Had some fun with the husband over the weekend and we thought it would be fun to share. I honestly love sucking cock and eating ass more than penetrative sex most of the time - There is something so intimate and sexy about it, and you get to really control how good that other person is feelin.

thebearwannabe post “Bless me, Father, for I have sinned. It has been three mont..

“Bless me, Father, for I have sinned. It has been three mont..

“Bless me, Father, for I have sinned. It has been three months since my last confession.” Father Augustine coughed lightly and shifted in his chair, the only movement in response being a small sign of the cross. The man on the other side of the screen held his breath for a moment, collecting his thoughts before letting the words escape at last. “I have been lustful. Unfaithful to God.” “Continue," Fa...

thebearwannabe post Happy Monday! Another throwback - One of my first times tryi..

Happy Monday! Another throwback - One of my first times tryi..

Happy Monday! Another throwback - One of my first times trying to do a professional daddy look (I miss having this amount of space in my old apartment...)

thebearwannabe post Happy Saturday! I know back in the day I used to have a Disc..

Happy Saturday! I know back in the day I used to have a Disc..

Happy Saturday! I know back in the day I used to have a Discord channel, but I sadly removed it due to being a little overwhelming to keep up with and maintain. I thought I'd keep something easier, and am super proud to present my new (free) telegram channel! https://t.me/+4NOcC731QhEyMTQx Use this special onlyfans-only (heh) link to gain access and check out my daily videos, behind the scenes and random lewds ...

thebearwannabe post (Turns out I forgot to caption this. Ass? Ass.)

(Turns out I forgot to caption this. Ass? Ass.)

(Turns out I forgot to caption this. Ass? Ass.)

thebearwannabe post Urgran groaned as the cock slowly pushed its way inside his ..

Urgran groaned as the cock slowly pushed its way inside his ..

Urgran groaned as the cock slowly pushed its way inside his hole. His knees pressed into the uncomfortable cobblestones, the coolness offering some semblance of comfort. The mercenary chuckled, pushing to the hilt and allowing the Orc to take every inch. "No wonder you came so cheap... You may not be much of a hired warrior, but you’re a good hole, aren’t you?" The human's words stung even more than h...

thebearwannabe post Happy Monday! Throwback to one of the first photoshoots I up..

Happy Monday! Throwback to one of the first photoshoots I up..

Happy Monday! Throwback to one of the first photoshoots I uploaded to OF 💖 I feel like I've improved so much since taking these photos.

Happy Friday! I took this video right after I got out of the..

Happy Friday! I took this video right after I got out of the shower (And took those pics you saw from a few days back lol) and wanted to try something new. Have some daddy ass shaking 💖

thebearwannabe post Thought it would be fun to take some photos in the shower an..

Thought it would be fun to take some photos in the shower an..

Thought it would be fun to take some photos in the shower and I had NO fucking clue how wide I've gotten recently 👀 Would love to sit on some cute faces and see how far you could eat this hole.

thebearwannabe post An uncomfortable silence fills the sleeper cabin as the burl..

An uncomfortable silence fills the sleeper cabin as the burl..

An uncomfortable silence fills the sleeper cabin as the burly trucker studies you through his dark sunglasses. The smell of staleness lingers in the confined space, making you wonder how anyone can spend so much time here. With the doors closed, all external noises—chatter, air brakes, and machinery—fade away, leaving only the two of you and the quickly growing sexual, primal tension. The trucker clears his throa...

thebearwannabe post I'm getting too big for this shower 🥴 (1/2)

I'm getting too big for this shower 🥴 (1/2)

I'm getting too big for this shower 🥴 (1/2)

Happy Friday! I hadn't jerked off in a few days and thought ..

Happy Friday! I hadn't jerked off in a few days and thought it would be fun to bust out the VHS camera for some vintage daddy play

thebearwannabe post Grant didn’t seem to mind having a roommate, I think. I paid..

Grant didn’t seem to mind having a roommate, I think. I paid..

Grant didn’t seem to mind having a roommate, I think. I paid my rent, and my part of the utilities and generally stayed out of the way while he was leaving for work or coming home late. In some ways, I felt like I was his wife or something; I would clean up the house and even cook dinner for him on occasion if I knew he had a rough day. Of course, I couldn’t deny that I wanted him to notice me. I often fo...

thebearwannabe post New outfit arrived 👀

New outfit arrived 👀

New outfit arrived 👀

thebearwannabe post Non-noodey but I felt extra daddy in the greenhouse 💖

Non-noodey but I felt extra daddy in the greenhouse 💖

Non-noodey but I felt extra daddy in the greenhouse 💖

thebearwannabe post Eli, your best friends Dad leads you out of his house and in..

Eli, your best friends Dad leads you out of his house and in..

Eli, your best friends Dad leads you out of his house and into a nearby detached garage, the sunlight dazzling you for a moment as you follow the carefully maintained stepping stones. You can’t help but feel like the mood has been a little deflated - Usually your visit would mean getting right down to business, but all your conversation and foreplay didn’t get anywhere. “I thought we could try something new.â...

Tomorrow is my Friday and I want some dicks to rate. Send me..

Tomorrow is my Friday and I want some dicks to rate. Send me some nice pictures and I'll tell you what I'll do to 'em

thebearwannabe post Took some excellent pictures of my tits today.

Took some excellent pictures of my tits today.

Took some excellent pictures of my tits today.

You where looking through some old home movie tapes and come..

You where looking through some old home movie tapes and come across something... weird. Do you tell anyone?

thebearwannabe post I’m delighted to see you here with me again, human. It was s..

I’m delighted to see you here with me again, human. It was s..

I’m delighted to see you here with me again, human. It was so lonely here without you. I require… payment before I can grant you any favors, you understand don’t you? Good. You’re sitting and comfortable. Start to grab at your crotch. Yes, just like that. Excellent. Increase the pressure as you work from the base of your cock to the head, just letting the tips of your fingers do all the work for now. It m...

thebearwannabe post You make your way to the meeting spot arranged beforehand - ..

You make your way to the meeting spot arranged beforehand - ..

You make your way to the meeting spot arranged beforehand - The local trucker rest stop, behind the gas station in an alleyway just secluded enough for some fun. As you enter alone, you press yourself against a slimy wall, feeling a mix of nervousness and excitement. For a place with such a notorious reputation, it's surprisingly underwhelming. You work away your disappointment as you massage your crotch, working...

Happy Friday! My amazing husband offered to join me, and I c..

Happy Friday! My amazing husband offered to join me, and I couldn't stop thinking about how sexy it would be to just... make out on camera and tease one another. Intimacy is sexy for me, so I hope you enjoy 💖

thebearwannabe post Happy Thursday! Your internet Dad wishes you good vibes and ..

Happy Thursday! Your internet Dad wishes you good vibes and ..

Happy Thursday! Your internet Dad wishes you good vibes and boners 💖 I'm recovering after a particularly hard week, but the weather is getting nicer and I'm looking forward to doing more photoshoots

thebearwannabe post Lysander couldn’t recall how he had even stumbled into the i..

Lysander couldn’t recall how he had even stumbled into the i..

Lysander couldn’t recall how he had even stumbled into the inn room, let alone paid for it. His typically pristine robes lay abandoned on the floor as he pushed himself against the burly Orc, slamming them both against a nearby wall. In the dim candlelight, Lysanders fingers fumbled and snaked between the openings of his partners leather armor, relishing every inch of warmth he could find before attempting to remov...

thebearwannabe post My husband @themoonunit is 6'5, absolutely towers over me, a..

My husband @themoonunit is 6'5, absolutely towers over me, a..

My husband @themoonunit is 6'5, absolutely towers over me, and is a huge, huge bottom. They had never been eaten out until we got together almost a decade ago, so I always make sure to give them extra attention when they request it 💖 Videos of me eating out his delicious ass going up tomorrow!

thebearwannabe post Happy Wednesday! My husband @themoonunit is a photogenic sex..

Happy Wednesday! My husband @themoonunit is a photogenic sex..

Happy Wednesday! My husband @themoonunit is a photogenic sexy creature, and I'm always so happy when they offer to help me make some content! We have some great things planned for the next few weeks 💖

thebearwannabe post “That’s why they call me the master!” The garage was hot and..

“That’s why they call me the master!” The garage was hot and..

“That’s why they call me the master!” The garage was hot and uncomfortable as I sat there with XxFelineM4sterxX69, AKA Jeremy to most people who have the distinct pleasure of knowing him IRL. He giggled, turning his screen towards me to show his quickest speedrun yet. He was cute, I’ll admit- Maybe that’s why I ended up visiting him so often back when I was in my early 20’s. “Phiew, it’s hotter than...

thebearwannabe post Sorry about the quiet-ness this week, was having some bad me..

Sorry about the quiet-ness this week, was having some bad me..

Sorry about the quiet-ness this week, was having some bad mental health days, but things are turning around 💖 Your internet Dad hopes you have an excellent Friday, and reminds you that you are loved, and I'm thankful to have you here 💖

thebearwannabe post Dave cleared his throat and looked around the sleeper cabin ..

Dave cleared his throat and looked around the sleeper cabin ..

Dave cleared his throat and looked around the sleeper cabin of his semitrailer, making sure one last time that every window was shut and every door locked. His laptop was open and ready, and soon enough the familiar, warm excitement in his cheeks and in his crotch came back. Camming in front of gay men, in a company truck no less, isn’t what the trucker expected to be doing on his slow nights at rest stops. The at...

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