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This isn't the first time you've had Giselle Palmer in your cellblock. She's back on a public lewdness charge after getting picked up for fucking someone in a nearby park. Giselle has been giving you the eyes during your cell checks and there is some serious tension. The warden is out of his office today, so it's your perfect chance. You tell the other guards that you have to conduct a full body cavity search of prisoner 0069 and you might not be back for some time. Within a minute of being in her cell her jumpsuit comes off and she begins begging you for your hard cock. Will you get shit-canned for fucking Miss Slutty Demeanor here on prison property? Probably. Is it worth it to have Giselle's tight pussy lips wrapped around your cock? Absolutely.


Davina Davis has been training for her upcoming MMA bout for months but hasn't been making much progress due to her bad luck with personal trainers. She doesn't quite have her right hook down, but she does look damn sexy in her fighting gear. Davina's fighting style is quite unique, no armbars or rear-naked chokes, but she's got plenty of other naked moves in her arsenal. Once she flashes her pussy at you, it's only a matter of time before you submit. Maybe she is ready for The Octagon after all.


There's a Halloween myth that Mrs. Love over on Elm Street picks one trick or treater to fuck every year if they come to her door with a magnum condom. Just an urban legend right? You've got some time to spend so you throw together last years costume and give it a shot. Within 5 minutes of knocking, you've got her going down on you like she's bobbing for apples. This festive Cougar isn't holding back and immediately after bringing her to orgasm, she demands that you fill her up with your hallow cream.


You're not that happy with your girlfriend, Alina. A couple of days ago when you were casually discussing sexual fantasies, she brought up a gang bang. Not entirely comfortable with the idea, you went ahead and brought her some toys, just to see how she'd really take it. But she quickly realizes that your's is the only dick that she wants, and she wants it bad. Show Alina that sometimes one dick is better than 3. Make her cum all over your cock and beg for you to shoot your hot load across her face.


Your son is getting married to Penny Pax. You will never understand how he bagged a busty redhead like that, he's the kind of guy that works out 6 times a week, shaves his chest, and plays by the book 24/7 - he's a bit of a pussy. You on the other hand, regularly skip work, and slam loose women. When Penny comes to you before her wedding night and complains about issues in the bedroom, she confesses her DILF fantasy to you. She hasn't felt a hard cock inside her for a while now, so she's keen to get every inch of you inside her before she ties the knot. You're going to hell anyway, go for it.


You're back in Chicago for your twenty-first birthday and your old friend Cadey Mercury has popped over for a visit. You've been in the friend zone for years despite making your crush on her pretty obvious. Something's different about her today though, she's missed you while you've been away at college and she's come over dressed as a present, ready to be unwrapped. Cadey doesn't have a cake for you, but how does a birthday cream pie sound?


One of the beauties of VR is that it allows you to step into someone else's shoes. Today, you're Lexi Belle's lesbian lover, Alana Cruise. You're sunbathing by the pool when Lexi struts over and reminds you of her strict no clothes by the pool policy and proceeds to strip off your bikini. Hiding just out of view from the rest of her party guests, she fetches her strap-on and puts it on you. She wants to be fucked and you're the only one who knows how to truly please her, so go ahead and be a good pussy pal and make her cum over and over again.


You decide to check on your house sitter, Brook Logan, over the hidden nanny cam and are surprised to see her in barely-there white lingerie. Brook suddenly notices the camera. She knows you’re there! She starts teasing and peeling away her lingerie, talking to the camera, then decides to look around for more ways to entertain you. She gets mischievous and looks through your wife’s closet, and finds all her sex toys! Brook starts going deep with her dildo, and then near orgasm with her vibrator. Edging her climax just for you, she discovers another toy, Tommy Torso. It’s of those “substitute guy” types of toys. She asks you to imagine this fake-dude is you. It seems strange at first, but once she takes the cock down to the root and starts grinding, you’re rock hard and dripping. It’s better than porn! You’re not distracted by some other guy’s dick, or his breathing and grubby hands. It’s just you, Brook, and her peaking orgasm. She better be ready when you get home!


The last thing you remember is your car slamming into a telephone pole. The accident sent you into a 3-week coma and your prognosis wasn't good. When your fiance Nina comes to see you, things go from bad to worse and as you flatline, she is obliged to break out the defibrillator. After the shock, Nina notices something hard under your gown. Hey, it's a sign of life, right? In a desperate bid to resuscitate you, she strips and mounts herself on your comatose cock. She cums twice before you even wake up and when you finally stir, Nina's ass is pressed against your cock - she's ready for more.


Emma Hix is one of your favorite students. Her sense of rhythm and timbre have improved considerably and she's started dressing more and more slutty each lesson which is obviously a nice bonus. But today she seems distracted. Some girls at school have been giving her shit about her bald pussy, so she asks you to take a look. Whether she waxes it and just wanted an excuse to flash her twat, or has pussy-localized alopecia, it looks pretty fucking good to you. She insists on showing you more so you decide to put the piano on hold and give her a skin flute lesson instead.


It's Monday night - karaoke night. Your girl Norah Nova loves to sing, so you take her to the local bar every week, even though you fucking hate karaoke. You just wanted to stay home and watch sports tonight, but Norah has devised a way to persuade you to come along. After stripping down and revealing her perky little B cup tits, she wraps her prehensile feet around your dick and puts you in her mouth. Feeling your cock in her throat gets her so wet that she can't help herself but ride you into a wave of orgasms.


When you read Ella Knox's resume, you knew she wasn't the right fit for the position you're interviewing for at your startup. No relevant experience, typos everywhere, and a handful of BS office skills. But she also attached a photo of herself. "Might as well give her a shot", you thought. Within 2 minutes of being in your office, she begins to show you her real qualifications. After grinding her pussy on your leg and blowing you, she puts you between her huge tits and rides you right there in your office. You just have to find a way to justify this to HR...