Tag: Sissy phone sex

Sissy Fantasy Mom

fantasy momFantasy mom? Do you need a mommy? I am not your typical mother. Yes, I love to nurture little boys, let them fuck mommy and learn all about sex from me. But, I like to be a sissy mom too. Think about it. Not all boys born into this world will grow up to be macho men. Some will be sissies, and some will be homos. I don’t believe a mother should blow smoke up her son or daughter’s ass. For example, have you ever watched one of those talent shows where a potential contestant swears they can sing like and angel because their mother told them so. Then they sing on national TV and your head explodes? Those mothers lied to their offspring. I won’t lie to my little ones. I have one son who is not like the others. He has a small cock. He is a teen boy; he is as big as he is going to get. I can’t tell him he is going to be a lady’s man like his older brother, because he is going to be a cuckold at best. I believe people are who they are from part nurture and part nature. I am nurturing my son to be sissy fag to bring out his nature. I have been pegging his ass for a year now. I have him wearing panties instead of boxers too. Recently, a friend of mine told me he fancied sissy boys. My son has not yet had a real cock. He was overdue for a real cock up his ass. I told my friend that I had a sissy son who needed more than my strap on could provide. I could see the wheels turning in his head. Last night, it was like one of my sissy phone sex calls came to life. My son got a real cock up his back door pussy. He loved it too. His sissy training is just beginning.  Are you a well trained sissy yet?

sissy phone sex

Sissy Phone Sex, Dress Up Time

sissy phone sex By the end of our sissy phone sex session, this is how you will be dressed.  Well, maybe with a few added accessories lol! Remembering back when you were young and you used to sneak into your mom’s drawers and try on her panties and bra?  Slipping those silky thigh highs up your legs and sliding into a pair of mommy’s high heels made you feel so pretty.  You knew you would get into a lot of trouble if daddy ever caught you though.  You’re a sissy, just accept it and let’s begin some basic sissy training.  Trust me, I  know what you want, and what you need.  First off, you need someone like me to tell you that it’s ok to crave a big black cock.  I NEVER met a sissy who didn’t.  See?  I already know part of your little secret.  With me, you can become the beautiful butterfly you were meant to be.  We can play dress up and maybe even try on a little makeup.  Turn you into the woman you want to be.  We can come up with you a new name to match your new persona.  I won’t tell anyone that you’re really a sissy.  I may even let you play with your little clitty and have you shove something up your little man pussy 😉

My Phone Sex Site is No Limits

phone sex siteMy phone sex site is an anything goes sort of site. I have no limits. I am usually shock proof, but I will never say never because sometimes my callers surprise me. Last night, my youngest son shocked me. I walked in on him getting butt fucked by his little friend. His little friend was not so little where it counts. My son has never demonstrated any interest in dick or he has been in the closet. I have men friends who would gnaw off their arm to fuck my baby in the ass. He thought he was in trouble when I busted him. I rubbed my pussy watching his little ass take a pounding. I was picturing all the things I could do with his ass as I masturbated and enjoyed the show. I have strap-ons to peg his ass. I have many friends who love little boys too. After Ryan left my son filled with his jizz, I pegged his ass.  His little rosebud was gaping open. This was not his first ass fucking.  His little dick got hard as I pegged him. He begged for more. My youngest one wanted a hardcore ass fucking. I wore him out in a good way.  Later in the evening, I called up this old guy I know who loves little boys. He is a neighborhood P man. He has been arrested for liking young boys, but his money always gets him out of trouble. His money would also get him in my son’s tight little boy ass. My son clearly likes dick in his ass. I was just profiting off what he likes. I watched this dirty old pervert fuck my son’s ass. It was my boy’s third ass fucking of the day. Damn, if I had only known he was a little butt fucker before now, I could have bought a new sports car. Never too late.

Forcing You To The Glory Hole

domination phone sexYou’re gonna do what the fuck I say!  You may address me as Madame or Mistress.  I’m really feeling very domme today.  If you’re willing to totally submit to anything I tell you to do, then domination phone sex is a must!  Today, you will be my slave.  I will turn you into the little bitch boy we both know is lurking in the shadows.  We are taking a little excursion today.  Wanna know where to?  Just a sec.  First we have to get you dressed, well barely.  You will wear the slave outfit I’ve carefully picked out.  You’re lucky I didn’t make you wear a cock cage.  Now you’re ready.  Is the suspense killing you?  Ok, I’m dragging your sorry claims to be straight ass to a glory hole.  We both know what you really want and today, it’s happening.  I’m gonna stand behind you with a crop and instruct you while you suck that cock poking through that hole in the wall.  Don’t even begin to try and tell me no. I will smack your cock balls and ass with this crop.  Then, I will out your wanna be sissy ass to your coworkers, family and friends.  You’re not just sucking one cock, oh no, I would never make it that easy faggot.  That’s what you really are.  Today, I’m gonna prove it.  You’re gonna suck every cock that comes through that hole and whenever I choose, you will turn around and offer up that slutty boy cunt.  Got your dick hard didn’t it?  I knew it.  Be who you really are.  I doubt you have the balls though.  If you’re really good, I may let you jack your cock for me.

Good Piggies Get Rewarded For Jacking It My Way

Guided Masterbation

I love coming right up to you and putting my cunt in your face. It’s nice and bald with fat plump lips. I like teasing you and then denying even touching you, I love lying in bed next to you and open my lips so you can all the pinkness that you want your dick in. I won’t let you have it, you will take that dick out and stroke it for me with my permission. I will get up close and look right into your eyes and tell you spit down on that prick and make it hard. I love watching it grow in your hand. The head is my favorite part, I love telling you to stroke it all the down slow to your balls and cup those kind of like you would my breasts.

I love coming up behind you while you are doing that and surprising you by licking around the rim of your asshole. I want you to stroke up and twist, stop when you get to the head and squeeze hard make it purple. I come back over by you and open my pussy up and act like I am going to back onto that cock but I don’t I want you to cup over the head while looking at my box and think about it squeezing that fat mushroom. Go back down and up, go faster and harder, don’t come until I let you. I am going to count down from 5 but I like to torture you. I start counting and tell you to stroke as fast and hard as you can and don’t come and don’t stop. I can hear you breathing hard and moaning. I finally let you release and it squirts all over my ass and starts dripping down to my bald pussy. Your reward for being so good is cleaning me up all dry.

Dirty Phone Sex Best Friend

dirty phone sexDirty phone sex is the only kind to have with a woman like me. My experiences and lifestyle are a far cry from vanilla. I don’t do vanilla well. A friend of mine asked me to be his faux date for a fancy work thing. He is a closeted gay man, but that would hurt him at work. So, I step in and play the hot girlfriend, so he can get cock up the ass and still get promotions. I don’t judge. Sexy mature women like me always have a posse of gay friends. His boss has the hots for me. In fact, his boss grew up jacking off to my porn because his daddy was a fan. At first, we were afraid my sexy past would hurt his career advancement, but his boss is a total pervert. He is just a homophobic pervert. He has no issue with his right hand man dating a whore as long as he doesn’t suck cock. I have been struggling though to rebuff his boss’s advances. He is aggressive and hot as fuck, even if narrow minded. I hate homophobes usually, but this one is rich, handsome and hung. How do I know he is hung? Because he has been sending me dick pics for months now. Last night I caved. I fucked my gay bestie’s boss in a supply closet. Here is the kicker though. I needed some insurance to protect my BFF’s job. I gave the boss a prostate exam with the end of a mop handle. Yes, you read that correctly. I sodomized the homophobic boss with a mop handle. And, I recorded how hard his dick was and how hard he came. The homophobes are usually closeted fags or sissies. I wasn’t sure what to make of this guy, but I knew if my friend’s job was ever in jeopardy for sucking dick, I had blackmail material I would use in a heartbeat. I created a monster. The boss has been sending me pictures all day of things that would make my sissy phone sex bitches blush. He is coming over tonight, so I can fuck him with a strap on.

sissy phone sex

Mean Phone Sex for Small Dicks

mean phone sex Do you like mean phone sex? I deliver mean woman phone sex! Clearly, I am too old to be the bratty princess type; however, I am a size queen when it comes to adult men. The young boys I fuck, well, they are still growing. When I see a grown man with an itty bitty dickie, I go all mean girl. I’ve done porn. I have fucked some of the biggest cocks in the industry. Plus, my adult son I bore when I was a teen girl has a 9 inch cock. My late husband had a 10 inch cock. I am a cougar in the height of my sexual prime, which means I love to fuck. I just don’t love to fuck small dicks. I do love shaming little dicks, however. I was at the strip club I feature at a couple times a month last night. There was this big spender who wanted the VIP room with me.  When guys shell out his kind of money for a private room, I know what they want and it’s a lot more than a lap dance. My club doesn’t care if we take money for sex as long as we don’t brag about it and we tip out. Since there is no strict policy, we don’t have to do any guy we don’t want to. Most girls don’t want to fuck old geezers or creepy greasy dudes. All I care about is money and cock size. But, a guy can have all the money in the world and I still won’t fuck him, or even blow him, if he has a shrimp dick. Alexander paid me $5,000 to fuck. He was handsome and rich, but that was not enough for a turtle dick. He had a dick so mall it could only be called a micro penis. I tossed his money in his face and laughed at him. I hurled about 100 tiny dick loser slams at him. Get this. The loser came. He came without touching himself; without me touching him. He gave me the money and thanked me for my honesty and integrity. I wish it was always that easy to make five grand.

Well, boys you want to stare or fuck?

Dirty phone talk

A friend of mine came to pick me up at the office. We had plans to get lunch and catch up, but when he arrived he had another guy friend with him. The two of them standing in my office was like way too much hotness so I felt the need to join. I asked the guys to bring the big planter I just bought from my car into my office, a big tree starting to grow so pretty heavy. Anyway, while they stepped out I stripped down to nothing and perched myself on my desk and took a provocative pose. As the guys hauled in the plant and set it on my floor, both of them let go of the plant to stare at me. “Well, boys you want to stare or fuck?” I said, and there was about 1.2 seconds of thought before they were both naked and cocks hard. I took them into the back part of my office that has basically a place to sleep and eat, I work a lot of hours so it’s convenient. I take a seat on the bed and ask them both to stand in front of me for inspection. With both cocks in my hand, I look up at them with a dirty smile. “You two are going to fuck each other while I watch,” I said and they looked at one another and shrugged with an alright gesture.Sissy phone sex

I don’t think either was a bottom or a top, they sucked each other off and they decided between themselves who was going to get fucked. The new stranger friend decided he was going to do the fuck, which left my friend to fuck me. We tried every position known to man and there was cum all over the place! Toe curling orgasms from fantasy bisexual fun and two very hot men fucking me in the mix.

I know you love that strapon

Sissy phone sex

One of my regular clients called, he loves pegging and being called a sissy. He asked for a session with me and asked me to be creative as possible when I meet up with him.
I walk into his work place looking like a plain old person, no sparkle, but I didn’t want to call too much attention to myself. I made my way to the TV area and found my mark. He was speaking with a customer, but when I cleared my throat he turned and looked at me, smiled and did a quick double take. He was either really shocked I was there or looking plain jane, may have been both. I walked around a little until he was finished. He came to me “Hello Maam.” I smiled and told him to find a back room. Once we were there I told him to strip slowly so I could watch. I quickly put a video camera where he couldn’t see it, and hit record. He turned around and finished removing the last piece of clothing and told me he was ready. I sat down on an office chair that seems to have been abandoned. “Stand there and get your cock hard, I want to watch.” Not too shy about it he starts stroking his cock.

Taboo phone sex

“Is your asshole ready?” I asked as I pulled out a rather large strap on. His eyes got wide but sparkled with the sight of the big cock that was going to get rammed up his ass. I put my cock on and told him to come and sit on my lap cowgirl and ride my cock like a sissy. I let him ram it up his own ass and he fucked that dildo like it was the last he’d ever have. I reached around and started to stroke his cock. He leaned back and started grunting at my stroking while the big cock was in his ass. “Yeah, take the whole thing you sissy, you’re just like a little sissy bitch for me aren’t you?” It wasn’t too long before he was shooting his load all over himself. When he was finished and he was getting dressed, I ask why he wasn’t nervous about someone walking in. “I’m the only one that has the keys to this back storage room.” I gave a nod in understanding and stood up, grabbed the video camera. When I had it in my hands, he asked where I got that from. I told him I put it right “over there” to record the whole thing. He face went white. “What are you going to do with it?” Well, I told him, I am going to hold onto it and he was going to be at my beck and call or I would get one of his co-workers to play the video in the store on all the TVs during the busiest time of the day. I have a new slave, and I have all kinds of things in store for him.

Pegging to the Brink of Crazy

Sissy phone sex

I guess sissy phone sex is in a category all by itself simply for the complexity of the playing, but one thing I know. I love pegging a man to the brink of crazy. I want you moaning, groaning, and begging me to cum. I want you writhing with how much pleasure you are feeling. Feel that cum creeping up your shaft needing to explode.
Sitting on your face, I lean over and start playing with your nice cock. Covering your balls in licks and taking your whole cock deep into my mouth. Hard as a rock I see, I love that. I climb off and walk to my walk-in closet and find my drawer with my entire collection of strap on cocks. I pick the medium one for you. Is this your first-time baby? I hope I make you a pegging slut all just for me. I grab your raging hard cock and start thrusting my cock, first just the tip getting you used it. Once you are relaxed and enjoying the light pushing, I slide it all the way in balls deep. Stroking your cock and fucking you in the ass seems to be your sweet spot. I fuck your ass harder and harder. You shoot your load out all over. I guess you liked that.