Category: Sissy training

Spoil Me, Sissy Boy

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The reason I play with other boys Daddy is because I have to. You know that itty bitty dickie of yours isn’t enough to satisfy me. Other men can make me scream, but no one spoils me like you do Daddy. I think you like it, don’t you? Seeing me gag on big, fat cocks must make you jealous though. Does it ever bother you when I play with them wearing the cute outfits you bought me? If it does, I don’t ever plan on stopping.

It’s so much fun seeing you stroke your tiny clitty while you watch me play with real men. I bet you wish sometimes that you were one of them, but you’ll never be like them. No matter how hard you try nothing will make you less pathetic or make your pencil dick grow. Just accept it. You can still make me happy by showering me with attention and gifts. That’s all you’re good for anyway. I’m the perfect Princess and your my little toy.

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Consider yourself lucky. I don’t get bored with you like I do with the other boys. That’s because you provide me with constant entertainment. Any guy with a massive rod can make a girl cum, but they can’t make me laugh the way you do Daddy. I’m happy as long as I’m amused. It’s not even that much fun hooking up with men if you aren’t there watching and looking so pathetic. Even if it throws some guys off, I don’t care. I just love degrading and humiliating you that much. It’s so hot to watch you squirm while my tight holes get stretched the way they should. I’ve been thinking about letting you fuck me with a strap on, but even that might be too good for you. Your cock should be locked up, that would make it better

Ms Piggy Sissy Day

panty boy phone sex sissyOur own Tinkerbell Transvestite had another Sissy Day. I would have never guessed just how much Sissy looks like Ms Piggy when she puts on a snout and piggy ears, the only thing that was missing was a curly piggy tail to make our Piggy Pet complete. One thing is for sure, if Ms Piggy ever needs a stunt double, our cross dressing Fairy Fag can stand in for her.The pink dress was perfect, in fact Ms Piggy actually has the same dress. How adorable is that? And did you see the cute little business cards that Princess Levi had made for our Little Dicky Sissy? They are such a pretty pink and Sissy looks so cute on them.sissy training buss card I think Sissy should have to pass them out on her Sissy day and offer her services for parties. I would love to see Ms Piggy Sissy be the entertainment at a cross dressing drag queen’s birthday party. You know instead of a clown or a magician, they could hire Ms Piggy Sissy. That would be one way for our Blackmail Piggy Pet to earn extra money to give to Princess. Princess could be on the phone telling her Sissy what to do. Wouldn’t it be funny if Princess made Ms Piggy Sissy do a lump of shame in her panties in the middle of the party. Everyone would smell Stinky Sissy but no one would be able to see that Little Dicky getting hard because that lump of shame is bouncing around in her pretty frilly panties.crossdressing phone sex bacon Of course Sissy would have to record the entire thing so she could show it to Princess and be critiqued on her performance. I am sure it would take several parties and several tries before Sissy got it just right to Princess’s satisfaction. In the mean time we could all watch Sissy perform for us. And if Sissy made Princess mad, Sissy might find the videos on you tube like those pretty videos of spa day!  In fact there very well may be something in this blog that is linked to the video of those beautiful long eyelashes being applied. What a bid smile Sissy had on her face in that video! Happy hunting I know your going to look for it so you can watch the video.hot phone sex sissy

Incest sex with Nephew Gets Kinky

Incest sex was only part of the bargain between my nephew and me. One afternoon I noticed a camera set-up in the bathroom “hidden”, and approached Mick about it. My nephew had been staying with me for a while off and on. Well, he has been recording me in the bathroom to jerk off too.

As the fair Aunt that I am, and well the therapist in me I wanted to sit him down and discuss some stuff. However, I decided to turn the tables a little. I set a camera up in my bedroom. That’s right I did catch him! Mick had taken to my panty, and lingerie  drawers when I was away. He had become fond of dressing up like a little bitch and jerk off to the feed from my bathroom.

Incest Sex

It appears I have a little Sissy bitch to deal with. My sister and her husband would certainly not want to see what I have caught on video. Looks like I have some leverage and about to have my own personal slave. Well, I cornered him good while he was undressing in the shower. In fact I caught him red pantied and his cock was raging hard.

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One of the best times to corner a guy about blackmailing him, is when he is in his most vulnerable state. I walked in on him wearing my panties and rubbing his throbbing cock. He was excited and shocked/ surprised that he creamed my panties. I motioned for him to remove the panties and hand them to me. Hesitantly he handed his cum soiled panties over.

“Get on all fours” I commanded Mick, and he did obey. I walked over to him and shoved the panties in his mouth. In turn I slipped my panties off and put the crotch on his nose. I then slid onto my bed and called Mick over like a dog and commanded him to lick my pussy. He obeyed well and I must admit I did like how big his dick has gotten. I would really like to take that for a test drive, and I did.

Needle Dick Bitch

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Whenever you’re out in public and you hear people laughing I bet you think they’re laughing at you. Before you were probably just paranoid, but now because of me it’s probably true. Remember that picture I took of you in a pair of frilly panties Daddy? There’s no way you forgot about it because you begged me not to share it with anyone else. It was only because that one little picture bothered you so much that I decided to send it to everyone you know.

Don’t worry Daddy I did it from your phone and sent it to all your contacts too and a few from my list as well. My good friend Damon loved the picture too. At first he thought it was a girl, but when he realized it was you he loved it even more. Your sad little clitty is nothing compared to Damon’s thick, 9 inches. He’ll be here soon so you don’t just have to take my word for it.

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When you first Damon I want you to be a good little bitch. Greet him on your knees and beg for his big black cock. While he is our home, you will treat Damon like a welcomed guest and will do whatever you are told. Any one of your three holes or maybe even all of them belong to Damon. If you’re luck you might just get to watch your little Princess get filled by his massive fuck stick too, but honestly I’ll probably just watch you suffer.

While you’re being used and abused by Damon I’ll be taking pictures for our scrap book. Maybe one day when I’m feeling bored I’ll upload every last one of them to the internet and a video too! If I wear stockings you’ll probably cry because you have a perverted stocking fetish. You’re such a big baby that you can’t stand being teased with them sometimes even if it’s only for a second. That’s okay Daddy go ahead and cry if you want to. I’m sure most people already know how pathetic you are, but just case anyone ever questions it I want to have proof.

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Mother / Daughter Phone Sex Strap-on Fun

mother / daughter phone sex incest familiesMy baby girl Morgan and I love to share men together. We have been sharing cock since she was just a little girl. Daddy’s dick. My brother’s cock. School boy dick. Even random stranger’s cock. But, sometimes we just like to play alone, especially if the dick is small. When she was growing up, it was often just us in the house because daddy traveled so much for work. In the beginning,  our relationship was just oral. I could spend hours tasting that sweet little cunnie, and she had no problem licking her mommy’s pussy either. We could make each other cum so hard.

As she grew older, and I got hornier, we incorporated sex toys. A trip to the  adult bookstore one rainy afternoon, and we came home with a strap-on that would forever change our lives. When I first put it on, Morgan’s eyes got so big. “It’s even bigger than Daddy’s cock,” she purred. When I instructed her to suck it like a good girl; she used even better oral technique than I had watched her use on her daddy. “I love you more than daddy,” she would giggle. She really did love pleasing me. Still does.

kinky phone sex family funThe first time I used the strap-on for her baby girl pussy, I was so wet just thinking about it. I lubed it first with some flavored gel for cocksucking. My sweet girl has always had a sweet tooth. She deep throated the passion fruit lube right off my strap-on too. I had her apply some more so I could fuck her pretty pink puffy holes. I got her up on my lap reverse cowgirl and lowered her inch by inch down my cock.  She pressed back into my body as she moaned “Ohhhh Mommmmmmy. ” I reached around to rub her swollen clitty as she continued to bounce up and down. She even fucked my strap-on better than she did her daddy’s cock.

Daddy popped her cherry, but my strap-on took her back door before any man did. Most young girls would want you to go slow on their ass; get them use to the discomfort, but not Morgan.  She was bouncing her ass on mommy’s pretend cock like a champ. I fingered her sweet bald pussy the entire time. We were both so wet  with excitement. When she started convulsing and shaking, I panicked for a second thinking I used too much force and hurt her bottom. That was not the case at all. She was having an assgasm! Her sweet pussy and ass drenched mommy. It is still a memory I masturbate too.

cheap phone sex specials kinky mommyNow Morgan uses it on mommy too. We love strap-on play with each other, and others. Not a week goes by that we don’t bring a sissy or a tiny dick loser home for a little kinky fun. Some of them know what we have in store for them, because really, what loser would get lucky with a hot mother/daughter duo? But some live on fantasy island and actually believe we would let their worthless cocks touch us. Morgan and I use a big strap-on with each other for a reason! We know we deserve pleasure! We prefer strap-on play with one another than a real dick that is pathetic.  We might let you watch if you got a teenie weenie, but understand, if you are packing a short stack, we fuck you, not the other way around!

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Sissy’s Easter Surprise

Sissy phone sexSissy is going to be hopping down the bunny trail with a basket full of goodies and her cotton tail. This is the one year anniversary of my wonderful idea for Sissy to dress as a bunny. Her costume is so tight and revealing and it shows off her wonderful legs.  She is going to be so cute Princess Levi is going to make her hop around in her pretty pink bunny outfit with her panties full of poo like a good poo poo pansy. Bouncing around in her lump of shame. A pretty little sissy for the world to see. Her gold hoop ear rings bouncing as she skips to the jingle jangle of her pretty bracelets. Sissy is so happy in her Fairy Fagot world, humming her favorite song “I’m A Poo Poo Pansy”  a tune she wrote all by herself for her Princess.Mommy sex I think for Easter Sissy should write a new song to the tune of  “Here Comes Peter Cotton Tail” for us. I have to say the bunny costume is the best idea I have ever come up with. It doesn’t seem like it’s been a year since the first time she put it on and was so nervous about going out in public like that. I believe Sissy was told to get a Piggy costume next, to show everyone that she is a Piggy Pet as well as a Tinkerbell Transvestite. I want to see Sissy dressed as a dolly with a pacifier and a diaper and a baby bottle and a big rattle for her next Sissy day. She should have to go out in public for the entire day and have to stay in that diaper all day and not be allowed to go to a regular bathroom till the end of her Sissy day. She should wear a bonnet and a little sissy dress that is real short with her frilly panties showing from under neath. I know that would get a lot of attention! Happy Easter Sissy, it has been a year full of wonderful Sissy days, I can’t wait to see what this year brings…..

 Sissy training

Little Dickey

sissy phone sex sissy1My little Harley/ Hailey loves our Sissy Mascot. She tells me so all the time. Making me take her to Sissy’s very own Fuckalicious page so she can look at all the pretty pictures of Sissy and read all the stories about her. That is where she saw all the songs that our Sissy Fairy Fag has and she begged me to write one for her. So I wrote a wonderful nursery rhyme for my sweet little sissy, Harley. Of course since it was inspired by her idol, Sissy, how could I not share this with her? After all Harley is going to grow up and be just like her some day. All dressed in frilly dresses with big gold hoop earrings, feeling so pretty.  In fact I have been thinking about giving Harley sissy days just like our Tinkerbell Transvestite. Sissy loves going out in public, the attention, people taking pictures, pointing and laughing at her. Harley wouldn’t get that reaction just yet. She is to young, no one can tell she is really a boy when she dressed up like Hailey and goes out. But when she gets older she is going to be just like our very own Piggy Pet. I know for Sissy her sissy days are part of her humiliation and shame, but somewhere out there among all the laughing adults is a little boy that wants to let his little girl out and he is looking at sissy with the same admiration that my Harley does. So here is the debut of the Little Dickey nursery rhyme, Harley’s first and one of many that Sissy has, enjoy~Mommy Darla loves you girls!

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 Little Dickey

Rub, Rub , Rub your clit

Little as can be

Merrily merrily merrily

Squirty squirt for me

Twirl twirl twirl around

Pretty as can be

Prissy prissy prissy

Curtsy once for me

Curtsy curtsy curtsy low

Knee to the ground

Sissy sissy sissy

Open up your mouth

Prance prance prance around

Skipping as you go

Bouncy bouncy bouncy

Go your lovely locks

Rub rub rub your dick

Little as it may be

Tiny tiny tiny

Pinch it once for me

What is that between your legs

A dick that you can’t see

I think you are a girly girl

That is why you love to twirl

I Miss Sissy

sissy fairy fag6It has been such a long long time since I have written about Sissy. And even longer since I have heard her sweet sissy voice. I know that Princess Levi has been keeping Sissy busy and has been dishing out humiliation and shame just like Sissy deserves. I saw this t-shirt and thought of how pretty Sissy would look in a tight fitting t-shirt like this with a cute little mini skirt, a pair of heels and big hoop earnings. It  made me think that Sissy should get some glitter and the next time Princess gives her a Sissy day she should have to wear the outfit I described. When Sissy gets home, if she is a real good girl maybe Princess will let sissy be a PooPoo Pansy and play with her little tiny clitty covered in poo. But Sissy would have to buy some glitter and cover her clitty in glitter so that it mixes with her poo and she can say that her new shirt is accurate. That our Fairy Faggot does actual poop glitter. Princess might even be nice enough to let Sissy squirty squirt . Just thinking about it makes me giggle. What a sight that would be! incest phone sex darla

Sissy Training with Princess Tori

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Daddy looks so cute walking around the house in my panties. He looks so good doing it that now I make him wear them all the time. Of course Daddy isn’t very happy about it, but when has that ever mattered to me? I even made him go out and buy me new panties so he could have all my old ones. It probably isn’t hard to believe that they all fit Daddy perfectly. With an itty bitty dickie like his he actually looks like a girl if you don’t look at the rest of him!
Sometimes just to add to poor little Daddy’s humiliation I make him wear a training bra with my panties. It’s even better when they match! If I’m feeling especially cruel I’ll make him wear them both under his clothes all day, even when he goes to work. No matter what Daddy has to wear my panties under his clothes. He knows the rules, but sometimes “chooses” to forget them. I don’t buy his petty excuses and that’s why now he’s wearing my old training bras more often.
If Daddy argues too much or refuses to buy me something that I want I punish him even worse. I make him wear a matching bra and panties, then get on cam. I love playing with Daddy when I know hundreds of people are watching me degrade him. Sometimes I even put on my nice, 10 inch strap on and stretch out Daddy’s poor little asshole. Don’t feel bad for the bratty little faggot, he knows he was asking for it. Daddy probably only acts like that because he secretly wants it but he’s too much of a bitch to admit it.

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Family Fucking with Madison and Morgan

family fucking mother daughter sexMy baby girl Morgan and I have long celebrated family fucking. And we are not stingy with our love; we play with other family members too. A few weeks ago, my nephew visited. He was only suppose to be here for a weekend, but a blizzard trapped him with us for over a week. I had hoped him and Morgan would have some fun together. He is cute with a nice cock. I fucked my cousins when I was their age. Honestly, I think all cousins fool around at some point together. Morgan was excited to get her greedy little mouth on his thick cock. That was until she came out of the shower to find her cousin trying on her panties and this frilly pink dress she sometimes wears for daddy. Crap. My nephew was a sissy. Perfectly good waste of a nice cock I thought. Morgan informed me, we could still make him part of our family fun time. My baby girl is so smart.

I have trained my share of sissies in my life, but most don’t have such nice dicks, so it made me a bit sad. One day when he was here, Morgan and I brought home a playmate. A well hung older man, very alpha. I told him about my sissy nephew; he didn’t seem to care that he would be around. I guess I was silly to think it would mind. He was going to fuck the world’s hottest mother daughter duo, so any guy would put up with a sissy! He wanted to fuck me first. As I was on all fours getting his hard thick shaft forced up my ass, Morgan got all dominant with her cousin. Ordered him between my legs. She called him all sorts of humiliating names.  Turned him on too, because his sissy stick grew pretty big. When our fuck toy shot his load up my ass, I pissed it out into my nephew’s mouth.  “Who’s the sissy fairy cum guzzling clean up bitch of this family,” I cooed?

sissy phone sex mother daughterMorgan laughed her ass off, but my nephew ate it up, literally! I loved pushing that cum into his ass. Watching Morgan and I humiliate him, made our plaything hard again. Of course this time he fucked my baby girl’s ass. Once Morgan’s tight asshole was filled with spunk, she sat on her cousin’s face and force fed him his treat. Sadly the snow melted and he went back home, but my baby girl and I sure had fun feeding him cum once we realized his true nature. Next visit, we are going to dress him up and use him as fluffer bait! Having a sissy fag in the family just makes family fucking more kinky!