Category Archive: Sissy training phone sex

My Son’s friend cums on mommy

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The feeling of that long white man meat tapping on my ass was the best feeling ever. I love it when my son’s friend, Benjamin. Makes those clapping noises when he taps the head of his cock onto my ass as if he is knocking on a door. Then he slides his cock up and down the crack of my ass right before he sticks it into this wet mommy cunthole of mine. He pushes himself deep inside of me and just sits inside my pussy. I can feel his cock jumping inside of me. He is barely 18 but can fuck for hours. It’s funny because he can last so long but with me. Only a couple of pumps and he pulls out and cums all over my ass. He massages that sticky cum all into mommy’s ass like lotion. This Milf still has some good pussy! Come try mommy out for yourself.

I Enjoy Being a Sissy Mom

sissy momSometimes it is fun to be a sissy mom. My oldest daughter is 30. She is from my first marriage and she has a friend who likes to cross dress. He has no mistress or sissy trainer in his life, so I am here to help him out occasionally. He came over last night wanting to dress for me. He had a few items with him, but I let him check out my closest. I have so many pretty things. All sorts of lingerie, sexy dresses and a ton of high heels. He was like a little boy in a candy store. All wide eyed and in awe off all the pretty things. I helped him pick out an outfit to wear for me. He wore a pink laced bra, matching panties, black thigh highs and a pair of black heels. I get a lot of sissy callers being a phone sex mommy, but this is a real sissy. It was like having another daughter. Once she was so pretty, I trained her back-door pussy with my strap-on. I had to use lots of lube because she was tight! Her clitty got huge as I pumped in and out of her sissy hole. This was the first time we had played with her special pussy and she loved it. Next session, I am taking her out to get the real thing. Every sissy should have a mom like me in her life.

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Mommy Has a Period Slave

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My teenage son was sniffing and jerking off into my period panties. I decided that I was going to make him have a period too and be my personal slave to do everything for me while my cunt was bloody. I woke up and was bleeding so I called my boy from his bed to grab me the tampons. I noticed that hard dickie right away and I sat on the edge of the tub. I asked what he was waiting for. Since he loves to pleasure himself with my nasty panties, he can lick my pussy clean and insert that super plus tampon in with his mouth! Only as my son was cleaning me up, I gave him a special surprise of warm piss down his throat too! After Mommy was all cleaned up, I made him turn around and I shoved a super plus Tampon up his ass and gave him two to take to school so he could change them out as needed. Are you a naughty boy like my son? Do you need a period and to clean mommy’s pussy up as well?

From Boy Pussy to Shiny Vagina

Sissy boy mommy

 

I want to cause ruin to your body, babe, just like I did last night. You remember when I had you wearing that cute dainty sexy outfit. Those red panties with the lace fronts and the cotton-tops they make your ass look phenomenal. All of my basketball Buddy’s love for me to bring you around they say your ass is something they could Palm easily. The cheerleaders, they look at you and think because of that body of yours that you drive men insane. I agree with the cheerleaders you do drive men crazy you and your boy pussy. Your little bitty clit of a dick isn’t even threatening. I met you Beautiful I put your beauty on display, and you got to have some of the most exciting times of your life. I’m supposed to be your everything like those red panties and that matching bra. I like you in this particular outfit. You look so sexy when you’re showing those beautiful long slender legs. I’ve always told you that your legs feel like Silk your whole body does. I taught you how to take care of yourself, didn’t I, and that’s why your transformation is so awe-inspiring. Look at you; you’re flawless; your makeup is that of amazing and those thigh-high pantyhose with the lace trimming. Babe, you could have any man you wanted. You like those boots, don’t you, but I want you and something sexier I love for those legs to be shown off. Last night we had a meeting and as you say it overtook you. I love how you prance around showing your sexy ass, but last night you got to show it all. I want you to know that the cheerleaders all said they envy how you can take cocks so well at both ends. You’re a sexy girl now. I can make your pure little boy pussy into a bold new shiny vagina.

Sissy Boy for a Son

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I always knew my boy could be a sissy. Ever since he was a little boy he seemed to always be interested in my make-up and clothes. I would always catch him watching me apply make-up.  One day I even caught him trying on a pair of my heels. At first I did not know how to take the fact that my boy was a Fag. Now i accept it because I do not have a daughter of my own. I always wanted to teach my daughter how to cuck cock and get her pussy fucked. Now i have a son to teach! That is even better. I can teach him how to get fucked in his boy pussy and how to suck a mean dick. I am in love with the fact I have a sissy son. Now that I am a sissy mommy, I can go shopping with my boy and the things we can do is endless. I can not wait to get home and show him this sexy lingerie I got him from the sex store. i wish I had more sissy son’s. I hope a few just fall into my lap. Who knows right?

Let Me Train You

 

Sissy training phone sex

Are you my sissy boy who needs to be trained to be exactly who you truly are? I can help you be the best sissy that you could ever dream of being. I love training hot little faggots I love making all of their dreams come true by making them the perfect girly boys. I am very nurturing I pay attention to you and I listen to your every sexual desire. Believe me, I am the mother of all sissy trainers because I’m naughty I can be dominant but I can also be very kind and welcoming. Let me make you who you really want to be I’ll dress you up in pink panties little cute pink lace bras and I’ll have you shave your legs so you can be smooth and alluring. I’ll make sure that you have the prettiest dresses and make your face up and get your nails and toes done to. I’ll take you to the hairdresser and have her make you over into a beautiful sexy panty whore. You can’t go wrong with me because I know how to make your body feel just like a natural woman. Don’t you want a nurturing Mommy to teach you how to be who you really want to be? I know you might have been born a male but I also know who you really are and that’s a female because gender is fluid and so are you. Don’t live your life in the wrong body when you can have me train you to be oh so right. Let this mommy be your trainer and teach you how to suck cock and take cock in your wet tight booty pussy. I know how you like it because I’ve trained several fag’s how to become sissy girls. I bet you your fat little clit is thumping right now and if it is you know what to do because that’s lesson one.

I have a sissy son so I’m a sissy mom

sissy momMy son said he was sick. I figured it was a Ferris Bueller type thing. He just wanted to skip school and have some fun. I get it. I didn’t take his temp or anything. I just trusted what he said. I stopped home at lunch to see if he was feeling okay. I half expected him to be gone. I got the surprise of my life when I found him sucking the neighbor boy in a pair of my panties. My son was a cock sucking fag? I knew he was not interested in my mommy pussy, at least not like his older brothers. I figured maybe he was just too young and one day he would be a mother fucker like his brothers. I knew the problem then. I didn’t bust him. I did watch him polish that neighbor boy’s knob well. I got to thinking that maybe what I had here was a sissy boy. What woman can’t use a sissy boy son? I left discreetly, but when I came home from work, I had a bag from Victoria Secret’s. I showed my son all the sexy things I bought and gauged his reactions. He clearly loved the sexy lingerie I bought. I asked him if he wanted to try the items on. He looked at me like he just won the lottery. He was a natural in lingerie.  I told my boy he was born to be a sissy. He has been my sissy ever since. So now I am a sissy mom but I love it.

Sissy Mom Pearl Has A Sissy Son

I love being a sissy mom. I have a sissy boy. I knew from the time he could walk that he was not going to grow into a man. I could have forced the issue; I could have gone against his natural inclinations, but where is the fun in that? My son would have hated me, and he would just grow up to be another unhappy person in the world. My son and I have a very special relationship. I promised him if he did well on his first test of the year, I would take him on a shopping spree to his favorite store. Most boys his age like shopping sprees at The Game Stop or a toy store. Not my sissy son. His favorite shop is Victoria Secret’s. He came home with an A+ on his first test yesterday, so we went to the mall. I even let him dress up in a pink dress and Mary Janes to go shopping. He was so happy! I am not ashamed of my sissy boy. We let the ladies know he had $500 to spend on pretty things. I helped him try on sexy undergarments he can where under his boy clothes at school. I hate that I must send him to school dressed like a boy, but the school is not progressive thinking. Now he has lots of pretty things to wear under his boy clothes to make him feel girly. The sales ladies loved dressing my sissy boy as much as I do. Do you need a sissy mommy too?

Sissy Mom

Cuckold Fun

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One of my favorite lovers is an older man.  He is completely taken with me.  Sends me flowers and love letters.  Promises many gifts, if I would just be his.  I’m not ready to belong to anyone, but I do very much enjoy his company.

Now, I’m usually pretty good at keeping my lovers from running into one another.  But one day, I was at my place, entertaining a younger man.  In fact, he was barely 18.  He had made me promise when we met the year before that, as soon as he was legal, I would show him the ropes.  He sought me out just a day after his birthday.

Such a sweet, young buck.   And so easy to make hard!  He was a virgin.  But I felt like the first thing he should learn to love was having his cock sucked.  When I slid that beauty into my mouth, it exploded almost immediately.  I swallowed every drop and I swear, he nearly fainted.

I decided to let him then fuck me on my screened front porch.  He was so excited and felt so daring.  About five minutes into the fuck, I looked over and saw my older gentleman friend peering through the screen at us.  He smiled.  I smiled back.  I began to loudly exclaim how much I loved young cock and I saw he it made his smile even bigger.  When all was said and done, I walked my young friend out to his car, telling him, “Now, don’t you ever settle for less from a lover.”  He kissed me sweetly and drove away.  I looked over and saw that my gentleman friend was in his car watching.  He smiled and drove away.

That night, by special delivery, I received a gorgeous pearl necklace.  The note said, “Thank you for reminding me today that I can’t compare to those young studs, but I’m happy to see you enjoy them.  I’ve been turned on all night.  Please let me know when I can come watch again.”

Sissy For Me

 

Sissy boy phone sex

Let Mommy make you into a faggot sissy whore I know I can make you feel good because I am a great trainer I can make your pussy feel like it’s real that’s right Sissy I call it a pussy because that’s what you want it to be. I want to dress you up like a faggot sissy. I want to make you into my personal sissy slut sex slave. You have the sexiest legs and lips I’ve ever seen. I want to see your legs in the air like a faggot whore I want to see you getting cock drove into you over and over again. I know that turns you want because you love being taken advantage of. You have loved to be a faggot sissy ever since you were a little runt Sissy. I can make your dreams come true, and you know that just as well as I do, I can make you feel like you want to feel. I know what your neighbor did to you, how he touched you and made you feel weak. Your neighbor is the reason you want to be a fucking Sissy, or is it just because it’s in you. You’re so destructive how you want to be tied up and gagged, that’s your fantasy, and I know all about it. I know all about your need to be treated like a helpless victim. I know about when you got fucked by all of those guys and that abandoned house, oh you thought I had no clue, but I know exactly what’s going on. I know that you are a weak bitch, and you want to be taken control of. You are a little week fag, and no one can treat you like me. I’ll bet you you feel like you should be getting fucked everyday buy loads of guys. I think you should get fucked by loads of guys too. I think that you deserve it. I know what happened to you. I know all of the bad things that happened to you that made you like you are today. I don’t feel sorry for you because I think it made you free. You’ve always wanted to be a sissy you’ve always yearned for cock; in fact, you called it in the art of attraction because you wanted it so bad. All of the other little ones used to tease you about your little twist you didn’t pay attention you should have straightened it up. If you had not gotten gangbanged in your life at such a young age, your girlfriend would be dating a man instead of a man who wants to be a sissy woman. I know everything about you. I know all of your torrid activities. Tonight I’m putting on the strap-on, and I’m going to make you into my slave sissy bitch. I hope you’re ready. I think of you as a come dumpster, and I’m going to make sure that when I get through fucking you, my friends will get their chance. You like that, don’t you any way I’m sure of it.

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