Category Archive: Sissy training

Sexy grandmas love humiliating sissies!

sexy grandmasSexy grandmas love little sissy boys, they’re always so amusing! Little Jeffy is a boy like that, he is very effeminate and weak so whenever I see him I make him into my sweet little girl. He always tries to protest but deep down he knows that I am right for doing it. He is very small in stature and skinny as hell, plus he has the smallest dick I have ever seen so really he’s more woman than man anyway. Besides, once I get him all dressed up and shove a dick in his mouth he is the happiest little sissy I have ever seen! He loves sucking dick and eating cum, he’ll take it any way he can get it… even if he is completely humiliated along the way!


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Bernadette

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Mommy Phone Sex Rape Fantasy

mommy phone sexMommy phone sex can be sweet or mean. It really is against my nature to be anything but a sweet, loving and nurturing mommy because that is how I am with my son and daughter. I raised them to enjoy sex with me and each other. Being a phone sex mommy, however, is sometimes different from real life. I get quite a few unruly boys. I’m not just talking about stealing mommy’s panties to jack off in; every boy does that. Some of my phone sex boys like to get rough with mommy. I had a mommy caller last night who failed to tell me he had rape phone sex fantasies. I am no taboos always, however, I am not exactly submissive. I am somewhere right in the middle of submissive and dominant. When Roy tried to surprise mommy my forcing her down and shoving his cock in her warm wet hole, well this mommy fought back. This mommy turned the tables on him. I’m stronger than I look, especially when pumped full of adrenaline. I pinned him down, handcuffed him to the bed post and gave him a dose of his own medicine. Turns out Roy loves a big dildo shoved up his asshole. Sometimes mommy thinks you want her to do exactly that when you sneak attach her. Mature women are not known for being submissive naturally. We get dominant and better with age like a bold wine. Roy was liking my dildo so much, I put the strap on I use with my little lesbian charges. I ravaged his ass like I ravage their little bald cunnies. Roy came hard with his ass being violated. Afterwards, he was all apologetic and scared that it made him gay. I explained that what I essentially did was massage his prostate so he would have a mind blowing, ball draining orgasm. If you boys want your prostates massaged, all you just need to ask!


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Victoria

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Training You to be an Obedient Sissy

Sissy Training

Forcing you to your knees, I make you wait patiently as I taunt and tease you. You’re my little sissy bitch, and you will be going through some extensive training to learn how to properly please your mistress. How humiliating it must be, to be dominated by your little sister. Wearing a sexy, tight dominatrix bodysuit, I have you stick your ass in the air with your head to the ground. If you lower your ass at all, I’ll punish you. You must withstand the lashings without moving an inch. Taking a tasseled whip, I lash your cheeks, harder and harder. Yelping like the sissy you are, you tuck your hips in on the sixth strike. I grab a small butt plug from my drawer and jam it inside your hole. Gripping your face in my hands, I hold your face close as I snarl at you to keep still. I continue with the whipping, and again, you try to tuck your tail-end between your legs like a pathetic animal. This time, I take a bigger butt plug and replace the first one. I love hearing you cringe and wince as it splits through your ass. I lay your back this time, and if you scrunch up your legs and torso, even a little, to protect your balls, there will be consequences. With my trusty whip in hand, I lash your cock and balls. This time on the third strike, you move from fear, like a pussy. Now you must really face the music. Taking a big strap on, I rip out the butt plug and fuck your ass hard. I can hear the pain in your sniveling whimpers. How pathetic. Looks like we will need a lot of training before you can please me properly.

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Aimee

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Sissy Mommy Phone Sex

mommy phone sex

Mommy phone sex is not predictable when you call me. I am a mommy switch! I can be a sweet loving mommy or I can be a mean mommy. I can even be a sissy mommy. I think all the pussy I have been getting lately has changed me. I feminized my son this week. He is home on summer break. I am not sure what came over me, but I suggested he put on a pair of my panties. Once I saw him in a pair of my pink panties, I got aroused. I wanted to see more of him looking girly. I had him put on a matching pink bra. From there, it got out of control. I put a garter belt and stockings on him, which he seemed to like. He said it centered him.  Next came the wig and the high heels. He clearly loved the whole look. His cock and balls were bursting through my panties. Pre cum even stained the front.  Dressed in lingerie like he looked like a little Lolita, all I could think about were my hot teen lesbian charges licking my pussy and making me money. Of course, I had him worship my pussy. He was the first pussy licker I trained. As he was between my legs I just kept thinking about how much money I could get off a feminized sissy boy ass. He clearly enjoyed being dressed up in my sexy undergarments. I wonder if he might like getting fucked in his boy pussy for money while mommy watched? Would you enjoy such a thing? You could be his first client or maybe I can feminize you too and pimp your boy pussy out too. I may be a dirty bisexual mommy, but I like sissy phone sex too.


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Victoria

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Family Fucking with Mommy, Daughter and a Sissy Boy Nephew

family fuckingFamily fucking is what Morgan and I specialize in. I get calls all the time asking me if I have a son. Sadly, I only have a daughter. As great as my little fuck slave girl is, I do wish I had a little boy to play with; and Morgan always wanted a brother to fuck. She got her wish this week; well sort of got her wish. My nephew Tyler has been staying with us. My sister is out of town on business and her husband is gone too, so Aunt Madison to the rescue. Tyler is younger than Morgan by several years. He is in high school still. Morgan was all excited for some kissing cousin action. I must admit, I was hoping to watch them fuck too. All allusions of sister fucking went out the door when Morgan caught Tyler dressed up in her sexy lingerie with her dildo up his ass. Tyler was a sissy boy. Not that there is anything wrong with sissies, we love sissies; but when a sissy has a good sized rod on him, it is disheartening. We like big cock more than sissies! But, Morgan and I have no shortage of big cocks in our life; sissies, however, are harder to come by, at least in the real word. What did we do? We gave my nephew some much needed sissy training. Morgan gave him a complete make over. Hair, nails, full body wax and dress. I masturbated watching her transform her cousin from a boy to a sissy. I already had the strap ons out; one for Morgan and one for me. As Aunt Morgan, I was going to take my nephew’s back door pussy. Morgan got to thrust in and out of his mouth. He is still here for a few more days, so we have some real men coming over to give our little sissy boy the real thing.


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MorganMadison

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Naughty sissy needed training from Grandma!

sissy phone sexMy naughty little sissy boy was caught in my panty drawer again! It was bad enough when he was getting all his squirties in my dirty panties but to try and mess up my clean ones too? Oh hell no! I am tired of doing extra laundry just because this little brat won’t leave my stuff alone so I had to punish him so that he would learn a lesson! I forced him into the sluttiest outfit I could find and made him do chores while I called up several friends to come help me punish him. He was expecting me to call a bunch of women over… I’m sure that he had visions of strap on cocks fucking him all day long but that was not what he was gonna get at all! No, I invited over several big black men and I made that sissy suck every one of their cocks… and he had to let them fuck his little boy pussy too! He cried and whined but I really think he learned his lesson… and if he didn’t I will just bring over more men next time!


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Bernadette

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Daddy The Sissy

Sissy phone sex DawnMommy, Daddy and I have a dirty family secret that no one else knows about, do you want me to tell you? Okay well here it goes, Daddy has an extreme Sissy fetish! Not only that, but he demands that Mommy and I are the only ones who take care of him and tend to all of his needs! Ever since I was just a youngster, Daddy has always acted like a Sissy. He gets in these bratty, cry-baby moods and that’s when he decides that he wants to engage in his humiliating fetish! Mommy and I feel very embarrassed for him, in fact it makes me cringe even having to talk about it and confess to such a monstrosity of behavior, especially from my Daddy! At this point though, all Mommy and I can do is laugh about it! We have learned to deal with it and put up with his erratic ways and fantasy! Daddy has a special room in the house set up that’s fully dedicated to his Sissy fetish. Inside the room, he has all sorts of toys and stuffed animals to play with, a cute little twin bed with silky pink bedding, and of course lots of miscellaneous items to help aide his wild fantasy! Daddy has a closet full of little girl clothes too, the more fluffy, frilly and princess-like the clothes look, the better! He loves dressing up and getting all dolled up as though he’s about to participate in a little girl’s beauty pageant. What I find most laughable out of all of this is that Daddy loves to wear diapers and suck on pacifiers as well! How ridiculous, right?!?! A grown ass man wearing diapers and soiling them, then having me and my Mommy clean him all up! He loves having his cock and balls played with while we give him a diaper change, especially when we suck all over and lick it so that it’s extra clean for him! Daddy doesn’t use his words to communicate, instead, he cries and whines like a little toddler. To shut him up, I shove the pacifier into his mouth so that he can suck on it and be satisfied! He loves to cum in his diaper too and he does it a lot! It’s a constant mess and constant clean up with Sissy Daddy!


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Dawn

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Prissy Sissy Loves Makeup

Sissy phone sex DawnHere she is everyone! This is the sassiest, prissiest, fruitiest fag sissy that you ever did see! She is the biggest whore too, isn’t that crazy?! She loves to come over to my house and have me help to turn her into the sexy little tinkerbell transvestite that she loves to be! This teenie weenie sissy loser loves to get all glammed up with makeup and having her hair done, it makes her confidence rise tremendously! She knows how much of a pathetic crossdresser she is, and loves to be humiliated while wearing a full face of sexy ass makeup, the more that she can cake on to her face, the better! All the girls on the site laugh and make fun of her for how fucking ridiculous she looks and acts, I can’t help but join in on the laughter! I mean come on, it”s hilarious, just look at her! The tight skimpy little feminine outfits paired with a full on beauty drag queen makeover is absolutely horrific! Prissy Sissy make me take her out in public after we get her all dolled up so that we can show her off, the more stares and laughs people make at her, the more she is turned on! She’s such a slut! She deserves every ounce of humiliation and mean remark that she receives!Sissy training Dawn


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Dawn

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Sissy phone sex

kinky phone sex

Look at this cutie with a fine little booty! This is our biggest house sissy whore! Can you believe it? I mean out of the whole whore house- she is the biggest one! I mean who could refuse her? Especially when she wears pink and acts like the little sissy fag that she is!

She is needing a good penetration! She gets all dolled up, only to get laughed at! She is so pretty right? Such a little fairy fag princes. I mean look at those legs, they really are a knock out. She just could dance around forever dressed like that with her being a little teenie weenie loser that she is.

She needs a big spanking on that pale little ass of hers! I want to just laugh at her as she “unladylike” bends over and her panties show! Spank that little ass you sissy slut! We need to plug her up with a fat dildo and then have her pull her panties up under her dress and make her walk around town strutting that ass dildo.

I mean I am sure she can tuck it away like she tucks away her, tiny little camel toe! I love giggling at her. As cute as she looks in heels and bent over like a perfect little bitch, she just brings such laughter to me. Especially when I picture her bare little booty wiggling around in the air.

She is such a pansy sissy! Now, enough jabbing and get to stuffing that back door pussy full so that we girls here can laugh our asses off! Haha the irony right? Not everyone can pull off those silky white panties, now can they?

Yes she truly is really gifted at being a prissy sissy little fruity fag. Dress up more for us you tinkerbell transvestite!

sissy phone sex


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Belle

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Mommy’s boy toy

Family fuckingI was at karate class with my daughter today and I had the weirdest experience. So they have an older class and there was this cute younger guy in there, he kept eyeballing my titties and I know he was fantasizing about fucking my tight little pussy too. Anyways after class was over he brushed my and grabbed my ass, I turned and he winked. I mean this is a younger guy. I was like ok, so I smiled back and pushed my titties together a little bit to flirt back. This little shit was waiting at my car when I walked out of the building, I could see his rock hard cock, his mom ended up calling him over to leave. Let me tell you, I would have fucked the shit outta this guy. I would have made him call me mommy and show him why! I bet his big fat cock would feel so amazing sliding in and out of me.


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Sherri

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