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One night in 2009 while coming home from a night of clubbing I walked up the stairs to my apartment and encountered my neighbor Darren. I freaked a little because I was still "in the closet' and only going out in my Melissa mode on weekends or when I was on vacation. Darren is a handsome black man with a great build, sexy eyes and a wonderful smile. Up until that night I had seen him before but we never said more than "Hello!" to one another in the breezeway or parking lot. He said "Hey, I didn't recognize you at first. You look great!" I felt myself blushing but I was also excited and flatter… Read more

I have never been involved in a relationship with a rich woman, and Ms. Cat definitely qualifies as wealthy. A multi-million-dollar house in an exclusive neighborhood (she also bought the lot in back so nobody builds to block the view), three luxury cars, a vacation home, commissioned art, a personal chef, personal trainer, gardener, cleaning staff, designer clothes, jewelry, First Class plane tickets, etc. And that’s just the stuff I know about. There is nothing cheap about anything she owns…well, maybe except me. She makes a fortune from her law practice, but I get the feeling she has other… Read more

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her holes will be open for business. schedule an appointment or join one of our parties.… Read more

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Sexy Sissy Jenn discuss why a sissy should always let men bareback her ass pussy and the benefits and thrills associated with shoving a naked cock into a sissy slut and cumming deep in her ass. https://soundcloud.com/jenn-love-715790452/barebacking-your-sissy https://soundcloud.com/jenn-love-715790452/barebacking-your-sissy… Read more

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In her latest podcast Jenn talks about the power of sissy porn in helping men realize what real women are, helping fags transition to faggothood, helping early stage sissies realize what they are and helping the world understand that sissies are the future of womankind. https://soundcloud.com/jenn-love-715790452/sissy-porn?fbclid=IwAR0Ave0mJoBmfpmzFfItJ9x_owa0Qh_zQuA5XdevNGqXSllU6g8bijgMU7I… Read more

Late in the summer of 1985 my older sister went away to college at Ohio state. I didn’t go back to school for another 2 weeks so I finally had the house to myself to do what I want. I wasn’t allowed to have freinds come over but I was able to go over their homes. My mom and dad worked 730-530 so I had the whole house to myself. I had been going through my moms drawers for the last 4 years anytime she’d go grocery shopping, etc, and I would put her satin white slips on and walk around the house feeling like a little girl. Now I was able to go through my sister bras, panties, and clothes so I wa… Read more

Just about to get started on another busy to be Sunday. Sundays usually start off waking up somewhere with a a guy or two. Then I have to rush home to meet my friends that like to cum over early. Once I take care of them I hop online to chat on social media to meet new people that might want to mix with some of my regulars that enjoy group sex. Most of my TOP friends enjoy the party and watching other men shooting there cum loads into my sloppy hole while I am sucking off someone else. I have have a huge pump bottle of lube by my bed but on sundays I never seem to need it...hehe. The only time… Read more

I love to cruise the adult book stores especially if they have an arcade to watch gay porn. I like to find the guys that are already horny and ready to go so when I get there their I can just find the men who have their doors just open a little so i can slip in and get on my knees and do what I do best..use my tongue rings up and down that shaft and make it squirt in my mouth. Sex in the book stores is great too. I can't get enough sex lately. I find myself at the gay arcades a lot lately. I need to get my cock and the good things they give me. I love the taste of precum when it squirts out fi… Read more

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Sexy Sissy Jenn explores the way so many bois slip u*********sly down the tunnel of sissyhood and travel the stage to wrongly thinking they are attracted to bio twat to becoming sissy twats that only desire cock. https://soundcloud.com/jenn-love-715790452/slipping-into-the-sissy-hole… Read more

Mistress Aim Broke Me Until I Became the Dedicated Crossdressing Anal Whore I am Today. I have been with my dominatrix the Queen of Whores, Amy, For over three years now. Amy is now 57 with long curly and well dyed red hair, a perfectly curvy body and beautiful face with a sensually wicked mouth. As it happens she has gained a little weight since I met her, but she wears it well. It’s the kind of thing that happens when you are in a relationship, even if you don’t admit that you are in one. Currently I live with her, renting an upstairs apartment in her house where I am on call as a slave wi… Read more

It took longer than I thought to get the arrangements made, but my double Domme session finally happened last Sunday. It was everything I had hoped for and more. Both ladies were skilled and sadistic, and I experienced a long afternoon of sensations and emotions that ran the spectrum. I think what made it so special is that they were very different in their approaches to domination, yet they both worked so well together. Mistress Natasha is an older woman with more than 20 years of BDSM experience. She is a master of the psychological aspects of D/s, and Her goal is to snake Her way into your… Read more

I was referred to the holytrainer site by an online fan of my submissive lifestyle on my profile. I love CD and anal play. I had a CB-6000 chastity device that I would occasionally use while I played dress-up and fucked my tight lil ass with a variety of toys. When my girlfriend discovered my kinky submissive side and didn't freak out and dump me, I entrusted her with all the keys to my chastity cage, and asked her to be my key-holder. The first night, she tormented me for hours teasing and taunting my encased cock while she toyed her pussy with a vibrating dildo and wore the keys arou… Read more

Looking back, I didn't really know it as cuckolding, but I've always enjoyed fucking other people. The first time I did it, I was 16 and in a relationship with a boy that was a little rocky. We'd had a row and I said something like "If you're going to act like an idiot then don't come back here and expect me to suck your dick like nothing's happened. You'll probably find me sucking someone else's." And that's where it started. He said I wouldn't dare. I said I wouldn't think twice about it if he continued to be a dick. Anyway, that night we went to a party and he was being a dick as usua… Read more

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In my latest podcast I explain why it is the essence of every sissy to service cock in any way, any time, any where. https://soundcloud.com/jenn-love-715790452/sissys-duty-to-serve-cock… Read more

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I had just gone back to high school after spring break my senior year. I had just had my first sexual experience dressed with a guy, my neighbour Kevin. All I could think about was having the opportunity to do it again. I had no idea that chance was gonna be the very next weekend. It was then that I realized what a CD slut I truly was... it was about 2 in the afternoon Saturday in early May. It was a cloudy cool rainy day. I had spent the afternoon hanging out with my girlfriend, till about 4 pm. While she was over the phone rang and it was my neighbour Kevin. He wanted to know if I wanted to… Read more

We are a cuckold couple! We are totally into assplay! We are really into forced BiAssLicking, BigTitty Rimjobs, RimGang, and NipplePlay!!! Hubby loves watching me smellfuck and rim random strangers! He loves watching me stick my nose deep up a strangers butthole. He loves sucking on my big toes while I eat strangers assholes. My big toes are so sexy and sensitive. When he sucks them really good dirty nasty I just rim that much better. I make sexy slurping noises while I suck rancid ass! I have HUGE tits. You like BigTittys? You wanna a BigTitty Rimjob? I am a 40 something blonde with a P… Read more

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Master instructed me to be ready and dressed as a trashy whore. Once Master arrived, he attach a leash to my collar. He then dragged my pathetic worthless sissy ass to his favorite club and then hand the leash to any man or woman who wanted to take me to the restroom and use me. I was under strict orders to do anything they tell me to and if I refused it will result in me being punished severely. I was told condoms will be optional and up to the user. Being at a club most men would used me as a urinal and then a blow job cum receptacle. With the occasional one violating my ass pussy. Most wome… Read more

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During my last travel i have been in thailand and i offer my sissie self to thai ladyboy them used me as sexy toy i try around 10 ladyboys have been fucked so nicelly , them love to fuck white sissies and never say to them to fuck softlly them just doo the opposite and fuck you hard I have find a sexy one and she enjoyed to fuck my ass and load all her cum in both holes Then day always started by a deep troath fuck i was luck her dick was normal size i was so wet of precum running out of my mouths She start to play with my ass ring fingering me i was feeling so lesbian that way 1 and… Read more

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I’m Jason, I started whoring my wife out after I discovered she cheated on me with her boss. I caught him fucking my innocent wife in the back seat of his car in the parking lot behind the store they worked in. He was pounding his cock in and out of her pussy and she was taking it like a cheap slut! After watching my wife pushing her hips and her twat up so her boss could get his cock deep into her cunt, I decided the my innocent wife was really made for fucking. I told her I saw her being unfaithful and letting her boss use her pussy for his pleasure and if that’s what kind of girl she was… Read more

The first time I ever took it in the ass was at 19 from my first wife I was 17 she was 20.after a year of mind blowing sex she wanted to try anal sex se we did she loved it and then on my 19 Bday she wanted to do me,now in the back of my mind I wanted to try it but never told her that. so we did it and it was bad real bad but we tried it again and again until we got it right and it was on after that.it was like a contest at who could take more.yea she always won but I did take her whole hand and loved it.anyway that lasted 7yr's.second wife was already into it so game was on with her.she loved… Read more

Years ago, I was in a booth at an adult bookstore, and as usual on my knees sucking cock. One of the guys left the door ajar and I could see a couple of guys watching, which got me even hotter. Then one guy asked the guy I was sucking, "A good cocksucker?" The guy I was sucking said, "Like a good faggot." I was on fire. When the guy who asked took his turn in the booth, I reached for his zipper, he stopped me, grabbed me by the hair and pulled my hair back. He said that he wanted more than a suck job. He was very hot looking, and had on some military garb including combat boots, which is a tur… Read more

Or, “How To Turn Your Tight Little Anus Into a Gaping, Sloppy Loose Ass-Cunt”. Let’s face it, if you are a man, straight, gay or whatever, you no doubt see the kind of fun women have getting penetrated. Probably even makes you a little jealous. But at the same time you also love putting your cock in one of those wet holes to be found in the human body. I admit, there is a stigma attached to it, like, only gay men like it. No, I’m not and neither is about 30% of the straight guys here that enjoy penetration. Some just enough for prostate massage and some so ruined they can be double fisted, and… Read more

Videos like this is what encouraged me to go ahead a ruin my balls completely. He not only orgasms after castration, but also without a head on his cock! It has been completely removed, and good job, too. Looks like he never had one. Here's what I'm talking about: Now seriously, you can't help getting horny even if you're straight. Let alone consider getting rid of your nuts. Yes, it took him awhile, but that's part of the pleasure, infrequent but very pleasurable orgasms, well worth waiting for, in my opinion. And easier… Read more

I know you are eager to learn my many ways. I don't have protocols, although I do have expectations. Rule 1: Always refer to me as Mistress or Goddess. Rule 2: Always Greet me before opening dialogue. Rule 3: Never use the word "cunt" or "twat". Rule 4: Read the "news" before chatting with me, you may want to know what type of mood I'm in first Rule 5: Respect me always Rule 6: Obey my every command. Rule 7: Disclose if you serve others Rule 8: Communication is a must Rule 9: Must be well groomed at all times Rule 10: Devotion is a must! Rule 11: A penalty if a… Read more