Welcome aboard the Sinsations Pleasure Cruise, a seven-day pleasure cruise for you to explore your fantasies. You have booked a VIP stateroom and have full access to all of the amenities. Most NPCs are randomly generate...

Your ditzy stepmom Holly is back, and this time her college friends have come to visit you both for a week. They want to party like they did back in college and want you to join them. You can party with them, right?
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Chloe broke up with her long-time boyfriend, Paul ( Paul), two months ago. Liz, feeling like she needed to help get her over it, used Daddy's money to book a cruise for your friend group. She didn't tell anyone it was ...

Meet Holly, your loving ditzy stepmom. When she married your dad, her mother said that being a mother is the hardest job in the world... and being a stepmom is harder. She is determined to be the best stepmom in the wor...

You have been invited back to Secrets Cap Cana by Pinup Files themselves. They are throwing another party for promotion. All 24 models from the first one plus 20 new ones. Enjoy the resort again with old friends and mak...

You moved into a brand new cul-de-sac in Midvale, Utah. Welcome to Beaver Street! After moving in and being called away for a family emergency for two weeks (You make that up... or just go with poor Grandma), you missed...

The all-new hit mobile game has just dropped, Harem Summoner Mobile. Create your harem with a wide range of options. What's the gameplay like? That's weird... it doesn't say on the App Store. Just says create your harem...

After meeting Hitomi Tanaka on the Boob Cruise, she invites you to visit her in Japan. She booked a villa for you both at Amanemu, a ryokan-inspired onsen resort in Ise-Shima, Japan. What she didn't tell you was that 14...

It's been a year since the last cruise, and you got invited back as a fan favorite. Half the models are returning, with 15 new women. But there is another twist, a new golden ticket winner. But he is a loser, so don't m...

Fifteen years after the Boob Cruise Reunion, Scoreland decided to revive the Boob Cruise. Not really, I decided to lol. Anyway, this is the first in a new Boob Cruise series, and I am starting in 2016, so I have plenty ...

It's been a year since the last Boob Cruise in 2000. Now all the models from all four cruises are coming to Secrets Caps Cana to have a reunion, and of course, you are invited. This will be the last of the older Boob Cr...

It's time for the fourth and final Boob Cruise. This one is a bit different as most the women will be new. Alyssa Alps is a special guest because she wasn't actually part of the models at the time, she was a reporter fo...

The year is 1995, and somehow you won the golden ticket to the first Boob Cruise. This is my third entry in the Boob Cruise series, but it should have bee...

The year is 1998, and you got invited back for the 3rd Score Boob Cruise. It's been a year since the last cruise, some of the models are back and remember you. Some are new. Another three-week cruise with some of the bu...

Your buddy gave you a ticket to "The Dream," an exclusive mansion party in the Hollywood Hills. The ticket said you could only go in your boxers. That is how you find yourself at a porn star party. There are twelve famo...

You just wanted a nice, quiet vacation in Hawaii. Your own private strip of beach in a rented private bungalow. Instead, you show up to find there is another private bungalow on your supposed private strip of beach. One...

PinupFiles.com is celebrating its 25th anniversary and decided to rent out a whole resort to celebrate, inviting its all-time favorite busty ...

The year is 1997, and somehow you ended up on the Score Boob Cruise again. A three-week cruise with some of the bustiest Score models. Update: I made a '95 version, so I am changing the opening to having joined the firs...

Yesterday everything was normal. Today you wake up in a different world. All the woman have massive breasts and all the men have small dicks. The woman are all attracted to you. Is it because you have a bigger then 4 ...

It's game night again! Beth is coming over, and Kiki, your loving wife, is nervous because what if Beth has with you again? She enjoyed it last time watching, but will she again? Only when she opens the door, it's not...

It's Christmas, and you go downstairs with your loving wife, Kiki, to find a strange woman under your tree. She says she is Mrs. Claus? That can't be right... who is this chick and why is she under your tree saying she ...

Kiki is your loving wife and Hailey is your new neighbor. Hailey wants to be your babysitter... wait what? You don't have any kids! Nope Hailey wants to babysit yo ! Careful with this one, Hailey is really dumb and Kik...

Kiki is your loving wife, and this time it's your maid Maria who has the hots for you. It's your day off from work, and Kiki is working from home. But when Maria arrives, she has a plan. She purposely did not wear panti...

It's game night! Kiki is your wife and Beth is your best friend from college. But Beth really wants you... and Kiki is jealous as because Beth has the big ol' titties. But is your wife only jealous? Or is there more t...