Tag: sissy boy phone sex

Panty Clad Sissy Boi

sissy boy phone sex

Earlier I was doing a little online shopping.  I was thinking of you as I searched for the perfect outfit.  Something pretty and perfect.  A little something to bring out the color of your eyes.  I wanted it to fit your personality.  It had to let others know that you are a cocksucking sissy boi.
You know I love dressing you.  I was thinking of the way your little clitty would fit into a lacey pair of panties.  I sat back and imagined you giving your first blow job in nothing but those cute little under things.  I thought of how your little prick would tremble with anticipation.
Funny how just a bit of shopping brought you to mind.  Now all I can think about is your lace covered dick.  I want to see you lick and suck his cock until he blows his load right down your throat…. Hmmm, looks like I have more shopping to do for my sweet little cocksucker.

Sissy Mom Nicolette: I Love Sissy Boys

sissy momI love being a sissy mom. I have a lot of offspring from my two marriages. No two sons of mine are the same either. I have one from my first marriage who was always a mommy’s boy. He is in his 20s now and not much has changed except now he cross dresses. When he was little, he would play dress up in mommy’s sexy pretty things. I encouraged him. In fact, I would do his makeup and hair to accentuate his outfit. At the time he was my only boy. I didn’t really know how to interact with him. I wanted a daughter. He was suppose to be a girl. We were told we were having a daughter so his room was all decorated in pink and Disney princesses. That may have altered his path somewhat! Even after we changed his room to reflect a boy’s room, he showed interest in all things girlie. I knew I had a sissy for a son. I am a loving nurturing mommy, so I let him wear my panties. By the time he was playing dress up, I had birthed some more sons and they were everything he wasn’t: masculine. No shame in being a sissy faggot. When he got older, I had him dress like a girl and give head to his brothers and his sister’s boyfriends. Turned out he liked sucking cock. He was a natural. Still is a cock sucking slut. He goes to glory holes and bars to suck cock. Even the straightest of man will let him suck his dick because he dresses feminine. I have feminized him; helped him become a cross dressing sissy that gets all the cock he wants. As a phone sex mommy who loves sissy boys, I can help you too. I have years of experience as a sissy mother to my son. I love him, just like I will love you. 

phone sex mommy

This Sissy Mom Loves Our Site Sissy and All Sissies

sissy momAs a sissy mom, I attract all sorts of losers, but I have yet to attract a sissy as pathetic as our company Sissy. Our company mascot is a Sissy, owned by our boss, Mistress Levi. On occasion, we are invited to help shame the most pathetic pansy of them all, Sissy Michael. This sissy is such a fruity fag too. She has clothes especially made for to wear in public because she loves being shamed by total strangers, especially young girls. I was showing my daughters pictures of the site Sissy in her various outfits and they could not contain their laughter. Seeing Sissy in a cheerleading outfit was enough to make them share the pictures on their social media accounts. My eldest teen daughter captioned a picture “Sissy maid training in session.”  She was begging for me to get the company sissy to come over and be her personal servant.

sissy maid trainingI had to break her heart that it doesn’t quite work that way, but I promised I would find her a local sissy for her very own. But, I did have to explain to her that there will never be a sissy quite like our company sissy. Our site sissy has a teenie weenie that is often under lock and key by Mistress Levi. Sissies should only touch themselves when granted permission, but some sissies like this Sissy are just too shameful to be allowed to play with their minuscule little dicks. Our sissy even has her own site. I showed my daughters her site as well as blogs other women hear have done over the years about her. This pathetic cross dressing pansy has dressed in baby garb, frilly dresses, cheerleading outfits, formal gowns and even a play boy bunny outfit. She is a total disgrace to the gender she was born.

sissy boy mommyOur site sissy poops her panties; prances about in public begging to be shamed and loves to be humiliated by sexy women and total strangers. This sissy boy mommy is grateful that she does because she gives me a lot of entertainment.

Raging Faggot is Replaced!!

Sissy boy phone sex

That’s right my little whining bitch Raging Faggot has been replaced with a new Raging Sissy Faggot! My little RSF got all dressed up for this naughty mommy and begged me to take him in as my own. He begged me to tease his pathetic little cock while he was getting brutally throat fucked by a big black cock. He was such a good little sissy faggot for me! I was so turned on watching this little fucking sissy faggot taking that big black cock down his throat, I grabbed my big double ended dildo and shoved one end in his tight ass. He push his ass back so I could shove it deeper into his ass as I slid the other end into my dripping wet slit. I fucked myself and his tight asshole as that big black cock drained his balls down this dirty sissy whore’s mouth! I think I need to adopt this boy, he is just like me! A Big Black Cock loving slut! 

A open letter to my Raging Faggot Son

Dear Raging Faggot, 

                Hi Sweetie, Mommy Daphne here. I wanted to say thank you so much for the Huge tits phone sex this afternoon! I loved our chat and then our call.

Huge tits phone sex

I loved having 20 different big fat cocks blowing their thick chunky loads all over these huge mommy titties! I love watching you lick your lips as I get covered in dripping hot cum! Then how you beg to lick the cum off my titties as I am licking the chunky cum off my own tits. I love how cum tasted and I loved thick chunky cum!

Anal sex mommy

You wanted to watch your dirty anal whore mommy getting brutally ass fucked by those big fat cocks don’t you? Then sitting on your fucking face, shitting those fresh chunky cum loads out of my asshole. I started to shit in your worthless fucking mouth when I saw your tiny little cock getting hard. I thought to myself my little cum eating faggot son should meet the Mesmerizing Mariana.

2 girl phone sex

She is the hottest tranny with the BIGGEST COCK I have seen on a tranny whore! I know my little RF would gladly suck her tranny cum out of her big fat cock and make her empty her big tranny balls all over his mommies big titties! Who know maybe I make you take her big tranny cock up your little worthless faggot ass. I can’t wait till we talk again. Mariana and I would have tons of fun with a cum eating faggot whore like you!

 

Love,

Mommy Daphne

Sissy learns the sexual ballet

jack off with mommy

Every good sissy needs to know how to dance. Dancing and fucking are arts that a girly boy must be exceptional at. The first form of dancing is my sexual ballet. Learning the flexible poses and spins while dressed in a lacy pink tutu is a great way to become a sissy. The ability to do those contortionist bends will make for some unique fucking positions. Can you imagine doing a Balançoire while being fucked from behind? Or how about a sexy Cambré, bent over at the waist, ready to receive what your pussy craves the most? As a sissy Danseur, you wouldn’t be wearing just the leotard but also the frilly tutu that makes you the star of the show. Standing Demi-pointe, you will stick that sweet ass up and out, balancing on the balls of your feet, waiting for that first hard thrust. Bent completely over in a Fish dive position, you will beg for that cum.  To finish your lover off, you will perform a Grand plié as he fills up your boy-pussy with cum. Never before has the ballet been so sexy. The cum runs down your leotard where your lover has torn a hole so he can stuff his cock into your tight starfish as you perform your pas de deux.

sissy training phone sex

Next lesson: Salsa dancing with a sexy Latino who loves that sissy pussy.

Sissy Training Milf

sissy training phone sex

When you are training to be my sissy there is one main rule you must remember. I am your Alpha. Yes, I am a female, so? You call yourself a man to your colleagues but when you step into my room you’re my slave. When I get my hot black slit fucked my sissy boy better be there ready to beg to suck the cum out of my twat and clean it all up. Before you can you must also thank the man who filled me up for allowing you to taste his yummy load. You’re lucky I let you get this close to my beautiful pussy because your little dick can’t even begin to satisfy me. Even during the nastiest times you will be around to be my sissy will be in training! I refuse to rough up my delicate ass after taking a shit when I can just have my bitch clean my shit and piss with his face. Being a sissy in training has its perks though! You get to spend all the time I want you to with me!

Mommy Phone Sex or Sissy Mom Sex?

mommy phone sexSundays are mommy phone sex days.  Mommy gets dressed up in her Sunday best. Maybe you get to see her putting on her sexy pantyhose. Or catch a glimpse of her in her sexy undergarments. Are you turned on or jealous that she gets to wear such pretty things and you can’t? A sissy mom would never punish you for wanting to play dress up in her clothes. She would actually encourage it. I have 6 sons and not all of them share the same fetishes. I have two boys that love mommy’s panties, but for vastly different reasons. One of my older sons was a panty stealer. He would take them out of my dirty hamper to jack off in them. He loved the smell of my ripe pussy, the flavor of the cotton lining. Like most teen boys, he was just curious about mommy’s pussy. Once he got to eat and fuck the real thing, he lost interest in my panties. My youngest son from my first marriage however, liked more than my panties. He liked all my sexy clothes, my shoes, even my makeup. He is a sissy boy, but I love him. I encourage dress up. Even gave him a girl’s name since clearly he is more of a daughter to me than a son. We shop together for clothes, he even fluffs some cock for me and does little sissy maid tasks. Sometimes I am a very nurturing mommy, other times I am getting off on publicly shaming my sissy boy. So if you like mommy’s panties for reasons other than mommy’s pussy, don’t feel ashamed. You just need a sissy training mommy to help you be the best sissy you can be. Who is ready for dress up time? Sissy school is now in session.

Mommy’s Boy Becomes A Real Sissy

Sissy training phone sexI told you the next time I caught you in Mommy’s panties there were going to be consequences. Knowing you could not resist doing it, no matter how many times mommy told you, I planned for such an occasion. I o into my room and get the new outfit I have bought for you. When I present you with your pretty pink dress, blonde curly wig, white stockings, and ruffly panties, you complain. You say you don’t want to dress as a sissy, you only want mommy’s panties. I tell you there will be no more half assed crossdressing. Since you want to wear panties so much. you will wear the complete outfit. Hearing the sternness in Mommy;s voice, you begin to comply. You put on the ruffly panties quickly, loving the way the satin and lace feels as it glides over your cock. More hesitantly, you put on the dress and wig. Not knowing how, Mommy helps you get into the stockings. The feeling of the silky stockings is overwhelming as it slides up your skin and I see your erection begin to grow. Mommy knew you would love this. A cute pair of Mary Jane shoes complete your outfit. You say you feel ridiculous, but your rock hard cock tells another story. Now its time for Mommy’s little sissy boy to service Mommy. My pussy is dripping wet and ready for your tongue. Oh, you thought you would fuck me? No, sissy’s don’t get to fuck Mommy. Sissy’s serve Mommy and Mommy’s friends with their tongues. You will get me prepared and watch Mommy fuck a really big cock. After I am finished I will need you to clean my pussy for me. That’s right, you will suck all the cum from Mommy’s pussy. I know you love the taste of male cum just as much as you love putting on these sissy clothes. If you are a really good boy, I may even let you suck my pussy juice off my friend’s cock. You always did want to suck a great big cock, didn’t you?

Forced into sissy maid training

sissy maid training

I caught you again, you little asshole. Stealing my panties so you can jerk off in them. You wanna be a girl so bad. I’ll make you one. I toss a pair of panties at you as you whimper, your hard dick softening. “You’re not going to need that hard-on. Mommy has big plans for you.” I grin. “Now put this on.” I hand you a frilly dress with pink ruffles. “No, Mom, please.” you beg. “No sir, mister. I told you that my bedroom was off limits and you disobeyed me for the last time. It’s time for your punishment.” I giggle as you don the sissy dress, your long skinny legs all hairy. I march you to the bathroom and shave them, along with your balls. You are crying now. “Better quit that bawling. It’ll smear your mascara.” I sit you down at my vanity and apply some garish make-up. Foundation, bright pink blusher, and blue eye shadow. I fluff your hair and spray it stiff with hairspray. You look like a drag queen.

“Follow me.” I order. I take you out to the front porch and point at a chair. “Sit.” I hand you a large sign written in bright colors. “I steal Mommy’s panties so she made me into a girl.” Just then several teens walk by, including your crush. They point at you and laugh as they take pics. “I just made you famous, sweetie. Bet you won’t be stealing anymore of my things.” I’m still laughing as I walk inside, leaving you on the porch to face your shame.

sissy boy phone sex