Tag: sissy training

Sissy training for my big brother gets hot

Sissy training

Sissy training for my big brother is always so hot when mommy gets involved.  Brandy sissy girl says no men allowed! But this little worthless citty having guy does love incest. Mommy busting him for wearing her panties and bras starts everything off.  Mommy loves to hide secrets like these from us girls. I know she thinks we are too young to understand about sissy fags. But we fuck each other and we know about big brothers’ ass-play. My baby sister and I already know there is some sugar in his tank! 

Let the women in your life be your sissy Trainers

My brother needs a tongue or a finger up his ass when we are having sex. Mommy thinks it is because he was born with a cute baby-sized dick. We know it’s not only that but that he has been doing some drugs that make it shrivel and shrink. So that pee-pee is worthless now. And it makes so much sense that he is sneaking into mommy’s room to model her sexy underthings. And when she finally let us in on his cross-dressing we know just what to do. The strap that mommy uses on us girls to train our pussies is the perfect fit for our sissy incest phone sex!

Dr Aimee Introduces Rosa to her inner Bitch!

Submissive phone sex

My client Rosa Meets her inner Bitch! 

I have a client Rosa who wanted help with Submissive phone sex. So, I called her and her crush into my office for quite the experience. I love helping a woman live up to her amazing dominant self.  and doing this 2-girl style is super empowering. 

He had no idea what he was in store for when he walked into my office. There she was standing in the middle of the room wearing black leather thigh high boots, a black leather corset and black leather skirt. His eyes were huge as she lifted her arm pointing the tip of her flogger at him and told him to get on his fucking knees. 

I could see she was nervous, so I came behind her whispering in her ear. Together we made him a whiny little bitch. I taught her just how to make a man worship her and love every single second of it. I love couples therapy sessions.

 

Sissy Training How I was trained to be a Sissy Trainer

sissy trainingSissy training all you little bitches and your sweet, naughty little pussy’s, is mama’s specialty.  I love my little sissy boys! Nothing makes mommy squirt more cum out than making a big muscular man resort to submitting to me on his knees in his pink ruffled dress, white cotton stockings, and shiny black dress shoes. How did we get here though? I believe it started with my youngest brother.

Realizing at a young age, I had a lot of control over the younger siblings, I took a particular interest to my youngest bro.  He was a Mommy’s boy but our mom was always busy.  However, there was one problem with our relationship.  I prayed my mom would give birth to a girl when he entered this world. Unfortunately for him, I didn’t let it go that my mom brought home the wrong gender.  I would take him everywhere with me, dress him in the pretty dresses from the attic that I would go get out, put little girlie wigs on him, dress him in stockings, dresses, jewelery, fancy little girl shoes, and even put on our Mommy’s makeup. My parents were too busy to notice that he spent entire days dressed like this.

As I got a little older as he did, I started noticing how hard his cock got when I would get out the dress. Being intrigued, I would get a little more extreme.  I made him have a girls name, tell me about his girl parts.  I frequently made him get on his hands and knees and serve me as he was my little sissy bitch. I invited friends to dress him up.  We were both getting off on it and I had no idea why, I just kept doing it.

One day after I was done dressing him up all day, he took off the dresses as I was also unchanging and I looked over at him and told him, does your pussy get hard now sissy cunt? That bitch sissy had a monster rocket coming out of it, enough to make this sissy (as in sister-me) wet my panties a bit.  I asked him if he needed a kiss on his sissy pussy and he nodded.  I demanded he lick mine too.  His bitch little tongue sure got my juices up and I got his pussy lubed up in return.  I couldn’t believe how horny my young whore self got over the control I had over my brother.

Now that we are older, he still asks me if we can have a few days a month to play dressup.  I never turn it down as I can’t say no to family. I also like giving his pussy a nice long, fat kiss for old times sake too.  Would love to hear your sissy stories or get you in line like I did my little sissy brother, all those years ago!

Dr Aimee and Her Twink loving slut!

Sissy training

I just finished up a session with a patient I will refer to ass Twink Lover .

Twink lover craves Naughty little twink type bois yet at the same time has a special place in his heart for Big Shemale Cock. That right boy’s and girls this Whore wants it all, and  really needs Some good old fashioned Sissy training.

Twink lover has yet to have his Cherry popped but wants and needs that dick bad, So Dr Aimee has set up a very special surprise session in which she has flown in 2 massive Tranny Cocks do do the job well.

Ms. Zula and Ms. Zena have been waiting weeks to feel Twink lover from the inside out and to not only pop that cherry but to breed him like the little bitch he is.  Pretty soon My sweet little friend will have she cock juice dripping from all his little whore holes.

I cant wait!

Aimee Has a New Kinky Beau!

Kinky phone sex

Dr. Aimee met a boy that checks all her naughty boxes, this boy could be the key to all of her Kinky phone sex fantasies.

Aimee’s new guy is sexy and hot and loves to dress up for her in stockings and heels. This makes Aimee’s heart go pitter patter and her sweet little pussy get very wet.

Aimee wants to explore every long hard inch of her new guys oversized massive clitty. She wants to lick and suck it while riding his face in a super-hot 69.

Aimee wants to dress up in lingerie together and head out to swingers’ clubs basking in their mutual sluttiness.

Aimee wants to treat her new Beau like a whore.

You know who you are baby!

The Closested Client

Sissy training

The Closested Client

I have this particular client that likes to pretend like he is not there for Sissy training although his fantasies are clearly all about his obsession with cock. 

Every week he sits with me and tells me all about how he loves to watch his wife fuck and suck all these different men. He really tries very hard to make it seem like it is about watching her be a dirty little slut and not that big throbbing cock. Of course, there are some cuckolds that just love to watch the pleasure, but this client goes into details about each of their dicks. 

Seriously, his denial was getting to me! So for his visit today I put out several giant dildos. Ones that looked just like real cock. Veins, balls mushroom heads, and long glorious shafts. Watching his mouth water as he sat there confirmed what I knew. He is a little sissy bitch! 

Sissy training with me; taught my cousin everything he knows

Sissy trainingMy Cousin Tiff is a faggot because of my Brother.. My brother used to molest him when he was younger… It wasn’t like tiff ever screamed bloody mercy.. Tiffany enjoyed having Incest sex with my big brother and getting her prostate milked by him. She literally would beg to have sleepovers at my house.. literally throw tantrums! My brother was in his late teens so his hormones were raging and he was never the kind of guy that attracted girls, anyway. If he wasn’t such a geek, girls would have a field day with his 8 inch cock.. I love blowing my brother, his juicy cock is what taught me how to be such a great Cock sucking whore. Tiff always knew about me and my brothers dirty secrets, he saw his Sister fucking my brother before too…

My brother is actually the only boy cousin, the rest of us are girls from this generation. I guess the odds were pretty high anyway for Tiff to turn out to be a cock craving slut. When Tiff gets filthy drunk she doesn’t care who is around she will act like a total whore and make sure she gets what she wants, a load. I am 4 years older than her, so she looks up to me. Plus, if it weren’t for me normalizing her behavior by giving her makeovers when we were young, she wouldn’t be who she is today.. Sissy training with dawn is what taught her how to be the sexy slut she is.. Long blonde Ginger hair paired with her green eyes look so fucking hot on her.. Nobody can even tell she was born a boy.. 

Sissy Training Tagteam

sissy training

Sissy Training A Gym rat with Sexy siren Ariel is sure to put you on your knees sucking a big fat BBC! We had no idea that The muscle-bound sexy trainer really had the small pee-pee in the rumors around the Gym. Isn’t it always the case, a sexy man with a  great personality and fit as a fidel? Aren’t they all either gay or have a small-ass shrimp dick? I already knew from peeping in the locker room a couple of times that Our Target, let us call him Sebastian because I’m sure he doesn’t want the whole world to know what a little dicked, submissive cock sucker he really is! Let me give a little backstory to this sissy phone sex blog!

When Sebastian was a teen he discovered that he was much smaller than his classmates during a sleepover, the boys told the girls and his high school years were spent with everyone knowing he was a little too small in his jockeys! So when Ariel came to work at the Gym, I knew I had to show off this sexy yet small dicked man! We surround Him in the shower asking why he wore his tidy whites in the shower and why we couldn’t see an outline of a cock. That’s when he admitted that he had a fit of jealousy over the swinging cock all around him.

Then when Ariel and I pants him, right in that shower we began laughing so hard at his Vienna sausage dick! It wasn’t long until our Domination skills took over and we had Sebastian licking and suckling our toes. But we had another surprise. Since our small dickie muscle man was so jelly of big cock we would give him some to suck on for us! If you need Mommy and daughter or just teen and Milf Domination phone sex check Ariel and me out for a good time! Well, a good time at least for us sexy ladies!
sissy phone sex

Sissy training from your big tits aunty

I love a good aunty brat who needs Sissy training. You were caught wearing my panties last time you were over, and I bent you over my knees and spanked your ass. But you love it, it got your clitty hard having aunties pussy by your face while getting spanked had you excited. It made this aunty cunt wet knowing I could do anything to you and you would let me. It didn’t take much for me to be able to take your panties off and spread your legs. I use my pussy juices to lube my fingers up. Since you are being punished, I just forced them hard into your boypussy. I pumped my fingers inside your sissy pussy hard and you begged for aunty to fuck you. This only told me you are ready for some Incest sex. It wouldn’t be hard for me to find a big dick daddy to fuck my sissy nephew. I knew that his daddy is a big dick freak, and it would be easy to convince him to give us some daddy cock.

Sissy training

My boyfriend forces Sissy training on his little brother

Sissy training I regularly have a threesome with my boyfriend and his brother.. They have been at it for ever and I am the lucky girl who gets to watch the two of them give one another a prostate milking while I massage my cunt! It turns me on to see how freaky they get when they have Incest sex.. I was able to turn my faggot boyfriend out. I sensed he had some tang in his tank and honestly I am an addict for anal; giving and receiving that is!

The first time we fucked we were wasted.. I fucked him right in the bed of my dads pickup truck. Literally, I fucked him! He begged me to finger his asshole, lucky for him I dropped his denims to his ankles and had my dildo in my purse.. I bent him over the bed and tucked his stiff dick between his legs.. Sucking the shaft of his cock while giving him a rim-job at once, I began pressing the head of his dick into his asshole.

His precum lathered his ass and I pushed the rubber dick into his asshole. Ripping him by his hair I dominated the fuck out of him.. The way he batted his lashes and whimpered had me coming back for more. The next time we met up at his place and that’s when I was introduced to his transgender brother. I soon learned my boyfriend had been offering Sissy training to his little brother for a while. He enjoyed his brothers big dick so much he was transitioning to try and hog his big dick for himself..

There was no way I was going to let that happen  so I started teaching the faggot how to properly do his hair and nails.. I even brought him shopping! We began tag teaming his brother, the two of us taking turns riding his dick with no rubber.. Whoever was lucky enough to make his cock burst inside of them the other was lucky enough to slurp it out.. We would then swap his cum back and forth while he stroked his limp dick stiff again. haha, we were so addicted their Sister fucking walked in on us once and we didn’t bother stopping.. She was too young to process what was happening in the first place!