Release Date: November 13, 2011
Playboy.com is on set with Sydney Barlette to shoot her exclusive pictorial. Get to know more about Sydney Barlette by watching our behind the scenes footage and the complete nude version available exclusively on Playboy Plus. Watch the video as Sydney Barlette reveals all her little secrets, adventures, fantasies, along with her fun & wild experiences. Release Date: April 18, 2012
Release Date: April 18, 2012
It’s Mash-Up Monday, and this time around, six of our sexiest Cybergirls get together for some of the hottest girl-on-girl action you’ll ever see. Natural beauties Victoria Winters and Cristy Nicole have one hot date, and they can’t wait to get home and leave each other’s best clothes all ov er the floor. Sweet brunettes Erika Knight and Justine Miller make with the holiday spirit with a string of Christmas lights and very little else, and busty Sydney Barlette gives in to beautiful Tiffany Crystal’s romantic advances. If beautiful girl-on-girl is your thing, then look no further – we’ve got the hottest girls kissing, touching and sharing some very intimate moments, right here on Playboy Plus. Release Date: December 2, 2013
Your one-time girlfriend is now your daddy’s trophy wife! How humiliating! Tessa used you to seduce the big boss of your company and the true man of your house. Now, they’re married – which means your ex-girfriend will be making you do chores, monitoring your masturbatory habits – and sending you to your room for time-outs and spankings! She’s even gonna make you call her M-M-M… LOL @ You! Release Date: January 18, 2012
Release Date: 2016-03-12
Release Date: 2016-03-14
Release Date: 2016-09-26
Release Date: 2016-09-27
To remind you that you no longer have ‘boyfriend’ status in her life, your ex-girlfriend has gotten you a sissy maid uniform. You’ll wear your unform and a pair of high heels when you come over to clean her condo and wash her new boyfriend’s laundry during their love-making sessions. Now, then. Change into your uniform, give Mistress a curtsey and say, ‘Thank you, Miss Tessa.’ Release Date: January 1, 2012
Release Date: Sep 11, 2016
Release Date: Dec 13, 2016
Release Date: Dec 13, 2016
“How hilarious. Even tho I’ve banished you from our bedroom, even tho the only sex you get from me is sexual humiliation, you’re more puppydog for princess than ever. Aren’t you? Well, cuckie, here I am in my bikini. Why don’t you pull that pair of my stolen hamper panties over your face and show me who still owns you.” Release Date: July 2, 2012
Cruel, dominant Tessa cooly and calmly applies her makeup and ignores your crybaby blubbering as you beg her not to cuckold you. The more you beg and grovel, the even less of a man you are to Tessa, silly wussy. So you might as well just take your place in Tessa’s closet and piddle your cucky tears into your ex-girlfriend’s sexed-up panties. You pathetic little reject. Release Date: January 8, 2012
“You’ve been in chastity for me for nearly a year now. You’ve lavished me with presents, made me laugh at you, and humiliated yourself in front of me, with the hope that I’d take pity on you. Well, you are pitiful. But I am ready to release you from chastity. Right after you answer one little question for me…” Release Date: July 9, 2016
Tess has decided to send you on a punishment assignment to show you exactly what she thinks of you as a man. Your humiliation begins with a snug pair of pink sissy panties tugged tight around your laughable little package. Strip and put your panties on while Tessa tries to contain her laughter. Once you’re properly attired, Tess is going to send you on a public sissy punishment assignment! Release Date: November 13, 2011
Tessa was hanging out at the pool with her girlfriends when she snagged you peeping at them. Tessa confronts you and dares you to show her what you were about to do with her dirty panty bottoms and body lotion. Whatsamatter, jerkyman? It’s not so fun being stared at and disrespected, is it? Maybe after Tess gets done sexually humiliating you in front her girlfriends you’ll learn to control your nasty urges. Wimp. Release Date: October 16, 2011
Goddess Tessa has found a way to put your puppy dog lust for her to use. Crawl into Tessa’s bedroom on your hands and knees, lucky loser boy, because Tessa is going to let you be her lowly outfit tester. Tessa is going use your sputtering boner to help her decide which sexy dress to wear for the date she has with her man. If you do a great job, Tessa will let you take home the panties she’s wearing! Release Date: January 29, 2012
“Youve only been in your chastity cage for a week but it gets tighter every time you think of me. Does it hurt even worse for you to have to see me in a bikini? You look like you’re about to cry. Would crybaby like something to dry his tears? How about a pair of my warm, moist panties to wear over your face?…” Release Date: October 13, 2014
"I didn’t think you’d show up at our school reunion after what I did to you at the prom all those years ago. I guess I’m going to have to put you in your place all over again. You know what’s really funny? The meaner I am to you, the more you fill your fist with love squirts for me. You disgusting, pathetic dweeb…" Release Date: July 26, 2012