Category: Sissy phone sex

He Wanted His Big Sister

Sissy Phone Sex

One of my favorite clients was into being made to be a sissy. He wanted his older sister so badly, but couldn’t bring himself to make a move on her. So I helped him work out some of those frustrations. When he came in for his session, I pushed him onto the couch and made him watch me rub my clit in little circles. Getting wet, I let out little moans. I could see his boner ready to rip through his pants. That little bitch got down to his knees when I told him to eat his big sister’s aching pussy. Licking my sensitive clit, he groped at my body. I smacked him across the face before shoving him to ground, straddling his mouth, forcing him to keep tonguing my slit. Grinding my hips, I gripped my hands in his hair as I came harder than I ever had before, my juices dripping down to his neck. Since he was so good for his big sister, I crawled backwards so I could let him slide his throbbing cock inside my drooling cunt. I pinned down his wrists as I rode my little sissy brother’s fuckstick. Making him beg me to let him cum, I smacked his face a few times and made him ask louder. Finally, I stuck his cock up my ass as I let him fill me with his hot cum. My perfect, slutty little brother!

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.

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!

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!

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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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!

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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.

Kinky Phone Sex Therapy For Pervs

Kinky phone sex therapy is what Dr. Lynn is here for. I’m really excited to assist in some twisted and dark desires that you may need to work out. Maybe the daughter of your Girlfriend is always teasing the shit out of you in her innocent playful ways. I know you need to get something off on this one, and maybe even have a hot scene of family fucking.

Some of the hottest scenes we can play out include incest, K9, family fucking therapy, and mommy issues. I am a opened minded therapist and very hands on. One of my sessions once included me assisting a man with his burning desire to fuck his sister. We did up a scene where I was visiting and he decided that he was going to take advantage of me while I was asleep.

I was in bed and my bro comes into the room and starts jerking his cock off standing over me as he slid his hand up my nighty. I was stirred awake and forcibly face fucked by him before he got me so fucking wet I let him penetrate and fuck me.

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Cucky Humiliation

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What’s that? You want to see me get fucked? You want to see Mommy and I taking cock after cock while you sit over in the corner with your wimpy little dick? I bet you do. I bet that’s all you think about with a pathetic excuse of cock you have there. If you’re lucky I’ll make you our little playboy bunny baby. You can be my little cocksucking whore, you can clean out my pussy and enjoy every drop of that real man cum. Do you like being a cucky loser watching the two hottest girls you’ve ever seen get rammed? Our holes are going to be stretched to the max – clearly something you could never do. We’re going to laugh at you and humiliate you just like you deserve! A great mix of my bratty voice and Mommy’s dominance will have your itty bitty dickie squirting in no time. Silly cucky, don’t you know we only take real man cock? You’ll soon learn.

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Sissy Maid Training with Darline

Sissy trainingMy favorite girl from Sophisticated hotties picked us a wonderful new little sissy slut boy for our new maid!

Darline had the little sissy slut by the hair, grinding her face into my wet, hairy, hungry cunt. The little maid, nearly ripping herself free of her latex outfit, eagerly lapped and suckled at my puffy pussy. It didn’t take long before my hips bucked and ground my clit to an orgasm all over her pretty little maid face.

My turn to direct our new little toy. Her next mission, was to finger her other mistress, Darline, into an even more powerful orgasm than my own.

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I held Darline’s legs open wide, placing my freshly dripping, post-orgasm cunt over her face while the little sissy bitch finger fucked her beautiful bald pussy, and suckled at her clit. She’d been such a good little slutty maid, I decided to give her a treat and jerk her cock off.

I got her to shoot a nice load all over the floor at the same time as Darlene squirted a perfect orgasm all over his sissy little fucking face. And of course, we made her clean up all our drippy messes from the floor, with her tongue. Our baby brother is such a good little maid!

I do believe this is the beginning of a wonderful working relationship.

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