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Showing 1 - 37 Videos

Sole Mates video from Morgana

Sole Mates by Morgana You take Morgana on a date for Valentine's day. You have something you have been really wanting to ask her. You both get seated at the restaurant and then she starts complimenting on the nice place. She's beautiful in her brand new dress. Her eyes sparkle in the candle light. You swallow hard and finally get the courage to ask her. She's beaming with excitement. She's been waiting for this day for a long time with you. Or so she thinks....you come out and say that you have a foot fetish! A ton of bricks are lifted from your shoulders and now just the anticipation on waiting for her reply. At first, she looks at you and is surprised. Then she admits that she isn't wearing any shoes and she wants you to cum to her feet. You can't wait to cum to her little feet. She teases and says you will forever be her foot slave. She gets you to cum in the restaurant then you hurry and get the check so you can go home and have a lot more fun!

^$5.00 Add to Cart

Tinder Date Transforms You Into A Sissy video from InfinityWhore

Tinder Date Transforms You Into A Sissy by InfinityWhore [This was a custom request] You've just got back from a successful Tinder date, at least, she invited you back to her place so you assume it went well. However, when you get there you quickly realize that something is wrong. She immediately tells you that it's not going to work out between you because she's after a real alpha man. She noticed your stuttering when you spoke to her and your sweaty palms while trying to eat and quickly realized that she intimidated you. You're not a real man - you're a beta male who doesn't deserve pussy. She humiliates you for thinking that you had a chance with a woman like her. While you try to process this information, she's already pulled out some pink frilly underwear and encourages you to put it on. You have always known your place deep down... but you're hesitant. So she teases you with the chance of seeing her tits. Put the bra on and you might be allowed a peak. You're such a simp and she is so hot so you slip out of your male clothes and into the pretty frilly bra. She laughs at you - you look ridiculous - but she keeps up her end of the deal and shows off her perfect tits. You could never have a chance with her. She even suggests that she might invite a real man over to fuck her while you're on clean-up duty. She teases you again with her pussy and you are so hard. She notices your hard cock and tells you that it would look better clad in matching frilly panties. She throws them at you with an evil smirk and sits back to tell you what a pretty girl you are becoming. You truly feel like the beta male you are now as you watch her show off her pussy and tell you that only real men get to see how perfect and wet it feels. You could never get her wet looking as pathetic as you do right now. One final touch... some pink sheer holds up to finalize the look. All sissied up - you watch the Goddess before you bend over and tease you with her holes. She reminds you again and again of your place until you truly realize how pathetic and beta you are. You were meant to be her sissy pet. She wants to collar and own you while you clean up after her and real men. She slips a buttplug into her arse but then quickly removes it and spins around to make you clean her arse off the glass toy with your mouth. You savor the small taste of her but she wants to stick the plug somewhere else. If you're to be a true sissy bitch, you must learn to take cock in your virgin hole and to cum without touching your pathetic cock. She encourages you through the process of the plug sliding into you for the first time. You're so tight but it feels good to be filled... especially knowing it's been inside a Goddesses arsehole too. She instructs you to very gently stroke your cock while the plug is in your arse - but to remember that over time she will train you to never touch that pathetic little worm again. Anal only for sissy bitches! As you near orgasm, she pushes the glass plug into your arse with her fingers and tells you to imagine it's another man fucking you because you have clearly never deserved pussy and will never get pussy ever again. You're her little sissy pet now.

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Date Night Fuck Machine 2 video from Blaze Fyre

Date Night Fuck Machine 2 by Blaze Fyre Wearing a sexy red dress after a night out. I had such a fun time with you. Do you want to have some fun? I have a surprise planned. Maybe you'd like to watch me play with myself before you fuck me. Fingering myself in bed as a warm up, followed by a strip tease. I play with my pussy and then I get out my fuck machine. I lay down on the bed and let it fuck me from behind. Lots of little moans and dirty talk throughout. My pussy lips vibrate from the vibrator. Close up angles mixed in. I orgasm twice, once in prone position and a 2nd time in missionary.

^$35.00 Add to Cart

Telling you About My Date JOI video from Eevie Lain

Telling you About My Date JOI by Eevie Lain I just got home from a hot date, and being the cuck you are, you can't wait to hear all about it. I strip out of my robe and begin to tell you about how the date went; what I wore, our fancy dinner, the foreplay, and how he fucked me afterwards. Through all of this, I tell you how to stroke your cock, what to imagine about my date, slowly stripping off the rest of my clothes. I end with a cum countdown and send you to clean yourself up.

^$7.00 Add to Cart

After Shower Sex with Girlfriend video from Adria Nite

After Shower Sex with Girlfriend by Adria Nite You got back from work a bit earlier than usual. You hear your girlfriend taking a shower so you just sit down in the kitchen to wait for her. She walks in, wearing just a towel, ready to start cooking dinner. When she notices you she laughs a bit scared and surprised. She kisses you and says she wasn’t expecting you this early but since she’s already here almost naked, dinner may as well wait. She drops the towel and starts kissing you. You immediately get hard seeing her body. She talks to you about how much she wants you, how your cock inside of her would make her happy. She spreads her legs and you put your dick in. She moans loudly in pleasure, it’s hard for her to decide if she is your loving girlfriend or a slut. She just may be both. You fuck her on her side and then she rides you to show you how passionate she is about you. When you’re close, you get up and cover her tits with your cum. She thanks you for fucking her, now it’s dinner time.

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CUSTOM Hotel Date P1: Jerk-off, implied video from Lorena Brink

CUSTOM Hotel Date P1: Jerk-off, implied by Lorena Brink Just arrived at the hotel where we are gonna have amazing sex tonight! but first we need to cool off at the swimming pool. you can’t wait till tonight so i give you a quick handjob to get your mind at ease. to be continued...

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Date Night video from Madisyn Wood

Date Night by Madisyn Wood I had such a nice time on our date! Now I want to show you some appreciation for being such a great boyfriend. I rub my ass on your cock before getting on my knees and sucking on you. Then you titfuck me on the bed and throat me before I ride you front and back. As I cum on your cock riding, I beg you to fill me. We have the best date nights!

^$8.00 Add to Cart

Date Time With Jasmeen video from Sophie Ladder

Date Time With Jasmeen by Sophie Ladder Jasmeen Lefleur and Sophie are getting ready to go out on a date, but Jasmeen is looking so beautiful that Sophie can't help but resist taking some time then and there. Makeouts move to Sophie going down on Jasmeen, and then Jasmeen going down on Sophie. The two then fuck in a variety of positions with Jasmeen on her back, side, and in doggy.

^$15.00 Add to Cart

Passionate After Date Fuck video from Fiona Dagger

Passionate After Date Fuck by Fiona Dagger (This was originally filmed as a custom video and the name Ben is used throughout) You and Fiona make yourselves comfortable on your bed, and she tells you how much of an amazing night she's having so far. She says this is the best date she's been on in ages, and admits that she asked your mutual friends to arrange a party so she could meet you, as she kept hearing them talking about you and it got her really curious! She says that once she looked you up on social media and saw your pictures she knew she had to meet you, and she was so thrilled when it worked out and you asked her on this date! You kiss passionately before she strips down to lingerie and stockings, then kneels before you to worship your cock with her tongue, paying you lots of compliments about what a nice cock it is and how happy she is that the date is going so well! You cum in her mouth and she swallows it gladly, then you quickly tell her don't worry, you'll be able to go again in no time! She's thrilled, especially when you tell her it's now her turn, and you peel off her panties to eat her pussy. While you're licking her, she confesses to you that after she met you at the party last week she went home and touched herself thinking about you, and made herself cum 3 times! You bring her to orgasm with your tongue, then she says she needs you inside her right now, and begs you to fuck her. You fuck her in missionary, taking it slow and sensual at first and then gradually building up the rhythm, then flip her over into doggy to keep pounding her. She cums hard on your cock, then gets on top of you to ride you for a few minutes, before you flip her back into missionary to finish together, giving her an earth shattering orgasm as you empty your seed into her!

^$13.00 Add to Cart

DON'T BE SHY, COME INSIDE video from Ellie Idol

DON'T BE SHY, COME INSIDE by Ellie Idol Ellie has invited you inside after a wonderful date. You're shy so you almost drove off afterward. It's a good thing you stayed. Once in her room, she takes the lead and since you are nervous, you're thankful for her assertiveness. After all, she's beautiful and you clicked so well...it'd be a shame not to take it a step further. Just let her lead the way down the path of pleasure. Let go of your fears so you can feel her mouth on your shaft. This is the warmup you need, her melting away your worries with every slurp. Soon, she'll be riding your fuck-stick begging for a hot load inside her silky tight pussy! Don't be shy, CUM inside now... ;)

^$11.00 Add to Cart

First Date Workwear & Panty Piss video from Sammie Cee

First Date Workwear & Panty Piss by Sammie Cee I arrive at our date a bit late after a very busy day at work, I'm still wearing my work clothes, a tight fitting blouse and a pair of smart trousers, I've been in meetings all day and not had a chance to go to the bathroom. You notice I am desperate for the toilet so I let you into a little secret of mine, I love having a full bladder, feeling so desperate to pee, and then sometimes just pissing myself while I'm still wearing all my clothes. I can see this excites you, I open my legs a little and start pissing myself there and then, you can see it trickling through my trousers, soaking them and pour off the chair onto the floor. This turns me on so much, I show you my wet trousers and panties underneath before pulling them back up and masturbating in front of you in my piss soaked clothes.

^$13.00 Add to Cart

A Very Taboo Date Night With Mommy video from Jayne Melons

A Very Taboo Date Night With Mommy by Jayne Melons *This was a custom video and includes a name a handful of times throughout Mommy comes home from a date, you notice she seems a bit upset, she tells you how he fat shamed her throughout the meal and she couldn't even enjoy her dinner. Like the perfect, loving son you are, you offer to make her a full meal all by yourself for her. After your date with Mommy, she introduces you to all the benefits of boyfriend and girlfriend...that's what happens after a date isn't it? And you and Mommy had an amazing date, which always ends in a kiss... Heavy taboo themes, family roleplay, mom/son

^$17.00 Add to Cart

Full Video - Sheer by Design video from Lily Mae Exhib

Full Video - Sheer by Design by Lily Mae Exhib In my latest video, Charlie and I hit up a couple of cocktail bars. I wear this ultra-sexy dress that a fan bought me. The entire top half is sheer! My full tits were extremely visible, but no one seemed to mind! Oh yeah, I wore crotchless panties as well. It was an exciting night!

^$15.00 Add to Cart

Fucking after our date video from Brea Rose

Fucking after our date by Brea Rose This whole video I would love it if you never leave a bubbly, sweet, extremely cheery tone. Even though you say and do sexual things, you never act seductive or even coy. It’s all very straightforward and matter of fact, and always cheery for the entire video. In fact, as much as possible, I would love it if you could minimise your sexual sounds and facial expressions and replace them with general happy and joyful expressions as if you were thinking “Wow! Isn’t sex fun?”. POV in your living room. We arrive at your place, you dressed in sweet but casual clothes, and you mention how happy you are that I decided to come over. We sit on the couch and chat for a minute about the date we just had (dinner and a movie, or something simple like that). “I know we’ve only been on a few dates, but I like you, I think you’re really sweet. Oh, no, don’t worry. It wasn’t too forward of you to come over. I had a great time tonight. I don’t know if you’re still hungry after dinner, but if you want dessert, I have ice cream, or I could suck you off.” I’m surprised by your offer which itself surprises you a little. Since I came over to your place, you assumed I wanted to have sex. “Of course I’m serious. Do you not want me to? Well alright then, let’s get those pants off.” You give me a blowjob for a couple of minutes, then you ask if I want to fuck you. The rest of the video is a handful of virtual sex positions.Towards the end, you say it’s okay to cum inside you, you’re on birth control. “Did you like that? Oh good!” “You can go ahead and clean up if you want. The bathroom’s down there. I’m just gonna finger myself until you get back. Then you can eat me out if you’d like, or you can fuck me in the ass if you’re up for it. See you in a minute. I’ll be right here.”

^$10.00 Add to Cart

KitKatFeedee Our First (Blind) Date video from KinkyCurvyKat

KitKatFeedee Our First (Blind) Date by KinkyCurvyKat Setting the scene: Your friends have set you up on yet another a blind date, this time with their "gorgeous, laid back" friend named Kat. If you're being honest, your hopes aren't very high seeing as the last couple haven't gone as well as you'd been wanting. After a quick back and forth via text, you and Kat settle on Italian. She's already sitting down when you arrive, and your immediately drawn to her easy smile and sapphire eyes. You can tell she's nervous, but despite the awkwardness of a blind date, the conversation comes as easily as her smile. You start with a round of mozzarella sticks, but find yourself amazed as she eats them all. You're used to girls picking at their meals on a first date, but Kat has an appetite and you can't look away. When the entree comes, you're shocked that she can still be eating. When Kat finally stands up, you can't hide your shock (and excitement) to see her in a white dress that shows off every inch of her body, and you suggest taking the rest to go at your place.

^$6.00 Add to Cart

Daddy Daughter Date video from Gigi Sweets

Daddy Daughter Date by Gigi Sweets You've asked your daughter to pretend to be your hot young date to a party a coworker of his is hosting. She giggles but agrees to do it. The night comes and she's getting ready, you haven't seen your daughter look as hot as she does tonight. Don't let her catch you staring! The thought of all your coworkers not being able to keep their eyes off of your hot daughter gets you so hard. . I wonder if you can convince her to let you have a taste..

^$25.00 Add to Cart

Enslaved by my Oiled Up Breasts video from Auriella Faen

Enslaved by my Oiled Up Breasts by Auriella Faen After a date, I take you into my room where you sit and focus only on my breasts as I oil them up and tell you to stroke. I take my top off, then my bra, oiling my big boobs up the whole time. When you shoot your seed all over my tits, you will then be enslaved by my tits and have a cage put on your cock. Life as you knew it is over.

^$10.00 Add to Cart

Date Laughs at Your Small Dick video from TheLunaBabyy

Date Laughs at Your Small Dick by TheLunaBabyy You've had a great night with Luna and she has asked you to come back to hers. She encourages you to get your trousers off but realises you're shy. She tells you to not be worried, she wont judge.... then you take off your trousers and she can't hold her laughter in! She is laughing at how small your unerect dick is... until she realises you're actually getting off on this! This makes her laugh even more. Luna can not believe you really get hard on this. She keeps mocking you and then tells you don't worry, you can both still be friends! But there's no way she can fuck you now. (Name used: Chris)

^$6.00 Add to Cart

Asian comes back from her date horny video from Mvngokitty

Asian comes back from her date horny by Mvngokitty So horny from my date, and didnt wear any panties... Find out if i squirt ! 7:47 mins

^$18.00 Add to Cart

Cute Cemetery Date video from Calyx Bielke

Cute Cemetery Date by Calyx Bielke Cory (QueerGalxo) and I go on a really sweet date - in the cemetery. This a super sweet video with hand holding, kissing, running around in the colorful fall leaves. Though we are worried people will see us and think it is weird that we are jamming a camera in a tree to catch us being publicly affectionate with each other. Then I'm really on the lookout when I publicly flash my boobs, bush and ass. There is nothing hardcore and no sex in this video - just know that you get to be a voyeur on our little adventurous (REAL) date!

^$8.00 Add to Cart

CUSTOM Hotel Date P3: Our Special Night video from Lorena Brink

CUSTOM Hotel Date P3: Our Special Night by Lorena Brink Finally after all that waiting we are gonna have some real fun! Starting with showing off my sexy body, then getting some booze and spilling it over my body and making you lick it all up. After that I make your cock nice and wet so you can finally fuck me, but you can’t cum yet! You have to cum between my tits, giving me your load over my chest. Now it’s time for a good night...

^$30.00 Add to Cart

Sloppy Head After Date video from Ava Luna

Sloppy Head After Date by Ava Luna I love it when a nice guy takes me out on a date! I try and repay the best I can... even when the dick is HUGE, but I know I'll always try my best to please... *Preview audio is quieter than video*

^$9.00 Add to Cart

Fucking Girlfriend's Sister video from Cattie

Fucking Girlfriend's Sister by Cattie Cattie comes barging into her sister's room looking for an opinion on her dress. She's got a BIG date tonight and she's nervous but, of course her sister's not home. However, YOU are... So she looks to you for an opinion. You tell her you'd "fuck her" but, her dress needs to be shorter. Brushing off your creepy remark, she hikes her dress up a little but, you tell her it needs to be shorter. She pulls it up to where it's hugging the bottom of her perky ass. This is too short! Right? She bends over and sure enough... her pussy is exposed... Embarrassed, she straightens up as you joke about her not wearing panties. But Cattie's on a mission to get dick downed tonight and panties will only get in the way. Even though she's trying to be somewhat modest, she has needs and wants tonight to go perfectly! She doesn't have someone she can fuck whenever she wants like you and her sister do... You go on to tell her you'll fuck her again. Throwing Cattie all off... She imagined you saying that right? Yeah, she thinks you're cute... but... you're like a brother to her... I mean, you are dating her sister... But in her desperate state... She considers. Show her your dick and MAYBE she'll go for it... As you pull out your cock, she now understands why her sister keeps you around! But she doesn't have a lot of time to spare so, she makes the hasty decision to go for it! If she's lucky... maybe she'll get fucked twice tonight!

^$11.00 Add to Cart

Blind Date with a Vampire video from Saint Lilith

Blind Date with a Vampire by Saint Lilith You've been looking for a freak, but are you ready for this one? Are you so desperate to get your dick sucked you'd risk a little nibble... or more?

^$20.00 Add to Cart

Calyx Plays Both Parts video from Calyx Bielke

Calyx Plays Both Parts by Calyx Bielke You ready for some gender bending roleplay? Want boy/girl action? Oh, I can give it to you - while playing BOTH PARTS! I play the guy and the girl in this video. Watch me go on a date with myself while flirting and teasing. Then whisk myself away to offer a blowjob in the hallway of the restaurant and try to not get caught. This was so much fun to make, and I hope you enjoy!

^$8.00 Add to Cart

Naked Cooking Vol 1. video from Ava Nikki

Naked Cooking Vol 1. by Ava Nikki Come hang out as I cook dinner for the two of us in a sexy outfit that slowly reveals more as we go along.

^$7.00 Add to Cart

POV Missionary video from Katherine Pine

POV Missionary by Katherine Pine Your date with Katherine has gone really well! Things have been amazing, so she wants to take things up a level. She wants to get serious with you. She entices you into fucking her. She starts by playing with her soft tits in front of you, she knows this is the best way to make your cock hard. She rubs her clit to make herself wet for you. You slide your cock in and watch her titties bounce up and down with each thrust. She is flexible and folds herself up while you rail her with your cock until she begs for your cum. TLDR: date night roleplay, POV missionary with a dildo, implied creampie This video was originally created as a custom video. I love making customs, I would be happy to bring your particular fantasy to life. Please feel free to contact me so I can create a special video for you! TAGS for this video: brunette, curvy, big tits, big ass, bouncing tits, bouncing ass, bouncing boobs, big boobs, huge tits, giant tits, body piercings, piercings, nipple piercings, tongue piercings, pussy, dirty talk, dirty talking, cute talk, Katherine Pine, katherine pine, kat pine, katherinepine19, katherineepine, body piercings, gothic, slutty, slut, whore, titty play, tits, ass, date, dating, date night, GFE, GF, girlfriend, girl friend, sex, missionary, dildo fucking, dildo play, pussy play, fingering, feet, legs in air, flexibility, POV, point of view, virtual sex VS, roleplays, cute talk, dirty talk,

^$12.00 Add to Cart

Tinder Date is Pregnant video from AnnaBubbly

Tinder Date is Pregnant by AnnaBubbly You matched with a girl on Tinder and show up to the first date only to discover she is heavily pregnant! I notice you are disappointed, so offer we just hook up because I understand not wanting to get so serious on the first date, and I am so horny anyways! We quickly and quietly hook up in the closet, where you cum inside my pussy.

^$4.00 Add to Cart

Cancelled Date: Draining Your Cock video from Lily Littles

Cancelled Date: Draining Your Cock by Lily Littles I was all excited for our date until something came up and you had to cancel. You didn't think you could get rid of me that easily though, did you? I've been thinking about this all day. I'm still going to have my way with you and drain the cum from your cock. GFE styled JOI. Mutual Masturbation.

^$20.00 Add to Cart

SPH Humiliation Date video from Cazzy Kush

SPH Humiliation Date by Cazzy Kush I am so fucking horny I can't stand it anymore so I grab your hand and bring you to the bedroom for a little private time.

Thinking your all about it too I tell you to drop your pants and show me your cock but then you begin to act real funny and that made me instantly think you had something to hide!

It took some doing but you finally gave in and drop them ugly ass pants to reveal something even uglier!

I could not believe my eyes, I was in total shock and then began to laugh as I could not hold back, I was super excited to get my pussy pounded by a nice, rock hard, huge cock but instead what you have well it looks like your testicles are giving a teeny tiny thumbs up.

Showing me that nubbin really destroyed my mood so instead I took to making fun of that cocklet because hey I needed something to do since I can not fill up both of my holes like I was planning on and you lied about so yeah it's time for your punishment you dickless fuck!

2018 Panther Productions Entertainment

^$9.00 Add to Cart

Date Night Public Cum video from Victoria Skywalker

Date Night Public Cum by Victoria Skywalker We meet for a date at a nice restaurant where we are served wine, but before we order our food, I tell you how I came with no panties and that I want you to watch me play with myself under the table. Want to watch me cum while fingering my hairy pussy under the table, while trying to keep quiet, surrounded by all the other patrons? ;)

^$15.00 Add to Cart

Secret Slut video from Jude Ryan

Secret Slut by Jude Ryan We've been on a few dates, and I thought perhaps we should spend some time getting to know one another a little more. So I invite you in, and tell you I want to take things slowly all the while thinking to myself how badly I want your cock. There seems to be a secret slut within me just begging to come out. Before I know it, I'm sucking your cock...and then riding you...and then taking your load in my mouth! Why would you take advantage of me when I said I wanted to take things slow?

^$13.00 Add to Cart

One Night Stand video from Victoria Skywalker

One Night Stand by Victoria Skywalker We happen to meet while on a boring weekend trips for work and decide to end the weekend with something much more exciting and naughty than business meetings. I enjoy sucking you, and riding you, and licking you clean. I hope we meet again some day. (LOTS of dirty talk! And i'm rockin' a small bush in this one.) ;)

^$15.00 Add to Cart

Let The Date Not be Over video from Adria Nite

Let The Date Not be Over by Adria Nite You walk your date back home. You both had an amazing time and you're planning to meet for the second time. She thanks you for the evening and says goodbye. She is not really optimistic about it though so you ask her what's going on. She is a bit embarrassed but confesses that for a couple of hours she has been super horny and finds you extremely hot. You feel the same way which surprises her. She invites you to her bedroom still in disbelief that this is happening. She starts sucking your cock and immediately feels relieved and even hornier. You continue fucking and she realises that she is indeed a slut and not necessairly a good girl. You fuck passionately, she rides you and you fuck her missionary and creampie her pussy. She feels the most satisfied she has ever felt. Staying for breakfast?

^$5.00 Add to Cart

Valentines Humiliation With Dream Domme video from InfinityWhore

Valentines Humiliation With Dream Domme by InfinityWhore You've finally taken out the girl of your dreams on a date and you invite her back to yours, expecting some fun - only she begins to degrade and humiliate you as soon as you get alone. She reminds you what a loser you were back at school and tells you she was embarrassed to be out on a date with you. What's more? She knows that you are married and begins to threaten you with that. She knows you haven't made your wife cum for years... so why would you think you could handle this Goddess? She tells you all about the alpha men that she lets touch her while she strips down out of her dress to tease you with her body. When she notices you are hard, she teases you about the size of your cock before denying you the sight of her perfect pink pussy (because you're such a loser).

^$13.00 Add to Cart

Date Night video from Blair Glass

Date Night by Blair Glass I know I know, meeting up in person is just not possible, but that doesn't mean we cant have some fun on a little online date! Its nice to see you and you've really been getting me so worked up. Its only fair I return the favor c;

^$7.00 Add to Cart

Frisky Frolic video from Avalon

Frisky Frolic by Avalon Let's go on a date - and get a little bit naughty. Enjoy this girlfriend experience video as we explore the Gardens together, with plenty of cheeky flashing, as I tempt you to take me right here, right now. With a short summer dress, no bra and crotchless panties, it could be so easy to have a little fun out here amongst the beauty, birdsong and rushing creeks of Nature. Watch me as I pleasure myself - stifling an orgasm - hidden amongst the bushes, or as I flash you along the paths. Enjoy Aussie forest and natural bird sounds, spot a dragon in the background, or just enjoy huge natural titties begging to escape from my little dress.

^$10.00 Add to Cart