Category: Sissy phone sex

International Condom Day Live Demonstrations: Birth of a Sissy

Tomorrow is International Condom Day, so some of my fellow nursing students and I did some practice demonstrations. We are having school demonstrations  all day tomorrow, so we needed practice putting condoms on properly. We had wooden cocks to use , lube, condoms…. the whole nine yards. I just don’t have much experience when condoms really. I always fuck bareback! We were drinking wine and decided we needed live models. I pulled a few of the hospital staff in. Of course they wanted hot young student nurses playing with their cocks. Wouldn’t you?

We had about 6 guys to help us practice our condom application skills. When we had them all naked  it was clear we had some men in the room, and a few boys! Hell, not even boys. We burst out laughing at one guy in particular. A doctor too. He likely has a Napoleon complex over his dick it was so short. My thumbnail was bigger! I mean there was NO WAY a condom would even fit on his dick. We joked with him. Started calling him Sissy Sally because Saul is a boy’s name, and he has a clit not a dick. We made him help us with getting the cocks hard for our practice round. When he tried to protest, I got all mean girl on him, forced his head down and made him suck some real man cock. Only thing a tiny dick loser is good for is sucking dick and serving me how ever I see fit.

Turns out once he was doing it, he realized he liked sucking cock. A sissy was born today! Once he had a couple cocks hard, I put the condoms on them. Did it perfectly too. I made Sally keep sucking them so they could fill the condoms up with cum, and I could practice the proper way to take them off. I had them line up from biggest to smallest cock. The bigger the cock, the more the cum. The more the cum, the better the man in my book. We had Sissy Sally chug all the cum from the condoms too. Too bad I can’t take her to the school demonstrations tomorrow. I think the best way to demonstrate how to use condoms is with live models!

But Sally was a wonderful discovery. A girl never has enough sissies to shame.

Mean Girl Phone Sex with Lovely Lucy

I made a new friend today. It’s a huge black strap on, and I am going to make you into my mean girl phone sex bitch.

Yes, I love to get fucked, but not by a little chode dick like you have. That silly thing just makes me laugh! Get on your knees, sissy boy. Your license may say you’re a man, but that worthless little pecker of yours says you haven’t come close. I’m going to have some fun with your backdoor cunt but first I want you to fit this whole dick in your mouth. Yours is puny, compared, isn’t it? Hey, actually, before you get on your knees, slip on these pretty pink panties. You’re a good little bitch, aren’t you. Get on your knees, bow before me. I need you to beg for this dick. Tell me how small and insignificant it makes you feel. Tuck your little excuse for a cock between your legs and wrap your faggot lips around this magnificent specimen. I’m going to grab the back of your head and fuck your throat until you choke & gag. I want you gag on my dick until you vomit. And then I’m going to turn you around and use your stomach contents to fuck your little sissy pussy. It’s so tight, but it’s meant for this, you’ll see. I’m going to tear your sissy hole wide open, and you’re going to squeal like a piggy. I’m going to cum hard as you cry out, begging me to stop. I guess I’ll stop, there’s nothing left in it for me after that. You’d better clean us up good though, my friend and me both. Lick my juices and your juices off, and clean yourself up. I’m ready to break your sissy cherry. Call me when you can handle us.

My Little Pony Boy

My pony boy started out as a pathetic panty boy. This dude was like a frigging pansy assed white boy that just didn’t “get IT”. Seriously he was dunce, in fact I started making him wear a dunce cap when we would go to the mall.

On outings with my pansy Dunce boy things were very strict and very public. I made this pansy stand at a “time out” in whatever corner in the mall where we happened to be near. He had to do this every time pansy ass starts playing with himself as he watches girls go into Victoria’s Secret.

So Stewart, that’s pansy ass pony boy, would get really excited near lingerie shops that he’d start getting all Rain Man like with me. Seems pansy had gotten in trouble digging in mommies panties and getting caught. I found out he would be forced to strip, bend over and mommy would insert a pony tail butt plug in poor Stewies poo shoot.

Stewies mommy would take a riders crop out and make Stewart crawl around with his pony tail in and his dingle balls just hanging free in the wind. His mommy would then force her pony boy to beg for some “pony nuggets”. Pony nuggets were special and came from mommy’s nugget hole. Yep those round brown turds that mommy builds up for her sweet pony boy to feast on.

Yep, my pansy pony poop muncher would start mumbling about being a pony and how mommy made pony do bad bad things. He would pace in a circle and repeat parts. I finally got him a My Little Pony costume cut the ass out to better accommodate his hot pink pony butt plug. 

Hot Teen Slut Summer Trains New Recruits

I answered an ad looking for a hot teen slut that I saw on my city’s Backpages online magazine. I am always looking for new fun ways to supplement my income. I have a pretty expensive lifestyle. Between school and my partying, I spend more a month than I bring in. Now, I am luckier than most girls because I have quite a few personal patrons that keep me in the pampered lifestyle I like. But, new experiences, money with no strings attached can be quite exhilarating too. The money being offered was sizable. I was intrigued, so I met with the man who placed it.

I was being offered a very large amount of money to turn this man’s two sons into sissies for his private use. Essentially, he was an old perv, single daddy, with boys instead of girls. He wanted hot teen sluts. He was looking for a girl who could not only transform his sons into pretty sissies, but could train them too. I have turned a few men into sissy faggots before. This was going to be fun. The fact that I was turning his sons into daughters for him to fuck, made it all the more exciting to me.

Summer’s Sissy School was open for business. First thing to do was get them on the proper supplements so their hair and nails would grow, as well their breasts. Some sissies get boob jobs, but you can get a nice natural B cup with the right supplements and diet. As a student nurse, I know a lot of tricks for transforming the masculine into the feminine. Next order of business was  wardrobe. I love to shop. Taking pansies shopping is so much fun. I love the looks people give when seeing a fag transform into a fairy fag princess.  Once you got the wardrobe, it is time to school your sissies in the art of acting like a good teen slut. This includes how to pee like a girl, sucking cock, how to walk like a girl, the art of teasing, hair and make-up tricks, how to shave your body, flirting, serving men and taking it up your back door pussy.

After a few weeks I had them looking like girls. Passable girls. They looked like his daughters, not his sons. The only real thing preventing them from being 100% girl were their dicks. I did my best to make them look like oversized clits. When you are a sissy, that is all you really have anyway. You stop having a dick, and you start having a clit! The day I presented his daughters to him was one of the proudest days of my life, for which I was rewarded handsomely. He was so impressed he doubled the money as a token of his appreciation. His girls service him daily. He tells me they are the best cock suckers. Well, duh! I taught them and few can drain a dick better than me. He also raves about how tight their pussies are too. I showed the girls some special tricks on keeping their back door tight and fresh for fucking. I know what it takes to please a man, especially an older man.

If you want to become a hot teen slut too, you need Summer’s School for Sissies. I work with all ages. You MUST be willing to submit completely to me, however. If you don’t you may not like my tactics for breaking your pansy ass. Regardless if you are just a pathetic loser with a tiny dick that belongs in little girl panties, or a girl trapped in a man’s body, or just a fairy faggot, I can turn you into the perfect pretty sissy! School is in session.

Deepthroat Blowjob Sissy

I was visiting my mother the other day, and reminded why I dislike her so much. She actually pissed me off big time as she had my old boyfriend over. He wasn’t there for me either! She is such a fucking cougar slut.

One reason he is an old boyfriend is simply that he was caught sucking dick. I mean he was seriously deep throating this massive black cock and he swallowed! What a fucking sissy. My mom never heard about that part or about how I had his bitch ass good.

I had my phone in hand and snapped a fucking picture of him sucking that dick and threw up an advertisement for Deepthroat Blowjob Sissy Slut looking for sperm donors. I had him dressed up like a slut and paraded his sissy bbc sucking ass around the mall.

The ad didn’t get published, it was my power over him and I still have that picture. You know all I could do is snicker to myself about my mom’s newest fling. I bet he looks really sweet in mommy’s granny panties!

Hot Teen Slut Summer Can Make You a Pretty Sissy Too

Do you like hot teen sluts? You are not alone. I’m a nursing student and it appears that just about every doctor at the hospital I do my internship at loves a hot teen slut too. In particular, this hot teen slut! I have several doctors who spoil me with attention. They buy me expensive gifts, wine and dine me, provide me with top end pharmaceutical party supplies, even take me on nice weekend getaways. I recently acquired a new fan. But, he is not my typical admirer. He is what you would call a sissy boy.  I mean a grown ass man wearing frilly dresses, talking like a girl, wanting to play with dolls and shit. BIG OLD FUCKING FAG.

I knew he didn’t want to fuck me. Any so called guy wearing panties, doesn’t have anything to satisfy me with. I was wrong. He has a big fat wallet. He is giving me tributes for my time. As he should; if you want my attention on the phone or in person, and you are a sissy, you simply have to pay me in cash or gifts to make me deal with your pathetic loser ass. This doctor has a double life. Brilliant surgeon by day, total sissy fairy fag by night. Wants me to teach him how to be a hot teen slut. Challenge accepted. Money in my purse pocketed. I’m going to have so much fun not only humiliating Dr. Sissy, but dressing her up. Our first session together I transformed her into amprissy sissy nurse. Look how pretty and pathetic she is? Feel free to laugh. All my patients are going too!

Are you a sissy or a sissy wannabe? I can turn you into a hot teen slut too! I think I did an awesome job with Prissy Sissy Nurse Sophia. What do you think?

Sissy Phone Sex with Samantha and Jillian: My First Sissy Encounter

My oldest grandson has a crush on his occasional babysitter, my step niece Jillian. She is a cutie. I caught him one day smelling and jacking off with her dirty pantyhose. It was actually quite a turn on, but I worried he may be a sissy. I decided to talk with Jillian about it. She assured me it was quite normal for boys his age to like a girl’s panties or pantyhose. She said all the boys she babysits for steal her pretty soiled undergarments. They do it to smell her sweet teen pussy. She then invited me to go shopping with her and her special friend. She said she wanted me to meet her friend, so I could rest assured that my grandson was no sissy.

 Jillian told me she met this rather special girl at the mall months ago. Apparently they were both shopping for frilly underwear and pantyhose and exchanged numbers. Jillian said she was a total sissy fairy fag and once I met her I would have no doubt that my grandson was just a normal hot blooded horny teen boy. I met them at the mall and Jillian introduced me to her Sissy Fairy Fag.  I was stunned. I could not help but burst out laughing. She was in a precious baby doll dress, wearing jingly jangly jewelry, and pumps and makeup. She was even in a diaper with one of those plastic protectors on the outside. Now this was clearly a sissy. When she spoke she was quite poised and articulate, which surprised me.

Sissy Fairy Fag wanted to impress me with her babysitting skills in case I ever needed help with my grand angels.  She informed me she has been taking care of her dollies for some time now and felt it was time to be in charge of live dollies. We were in a baby store shopping for some pacifiers and toys for her when she put her Hello Kitty doll on the changing table and demonstrated how to change a poopy diaper and feed a little one. I knew my grand girls would love her. She was a life size doll. A big old pathetic sweet sissy fairy fag.  They could dress her up, put make up on her, do her nails, style her hair, sing songs together, play Candy Land, laugh at her… I felt good confident about Sissy Fairy Fag’s ability to take care of my angels. She was sort of a faggy Mary Poppins. LOL.

Thanks to Jillian, I know understood what a real fairy is all about. My grandson was far more of a man than Sissy Fairy Fag could ever hope to be, despite the age difference. My grandson likes to masturbate his cock with Jillian’s panties and pantyhose, not wear them and prance around the house playing with his little pee pee singling pansy ass tunes. In fact my grandson at his young age has a bigger pecker than Sissy Fairy Fag. She pulled her panties right down in the store to show us what a tiny little clitty she has too. I am still laughing. I’m in awe though of how someone so pathetic could be so comfortable in her skin. She had a great sissy trainer. Jillian told me, Mistress Levi made Sissy Fairy Fag who she is today. Well kudos to her. But I am keeping that hot bitch away from my sons and grandsons! I want real men in household.

Babysitter Phone Sex Fantasy With A Submissive Daddy

He was late coming home from his date.  He has been single for a long time and he needed to get out and away from his sons and daughter.  After a long night of not giving a fuck of what they were into or up to they went to bed.  I kept looking at the clock and it just kept getting later and later.  I had had enough of doing this, I wanted to go out with my friends.  I was stuck in this house with a parental control on the cable so I couldn’t even watch anything other than cartoons.  My brain was going to bleed if he didn’t hurry the hell up.

He came in and didn’t even say he was sorry.  He handed me a whole fifteen dollars and told me to have a good night.  Are you kidding me? Fifteen dollars for six hellacious hours of babysitting? No, no, NO!  I just looked at him and told him that I wanted more than this.  He told me that he didn’t have anymore money, I told him then he better get back out there and tap an ATM or something because I was not satisfied with my pay. 

He told me that he wasn’t going back out in a very stern voice.  What? Nobody talks to me that way, EVER!  I put my stuff down and poked him in the chest and told him, “Listen, YOU are going to get the fuck back out there, and YOU are going to get me more money…NOW!”  He actually shrunk back.  He mumbled, “Yes Ma’am.”  I started to smile and let the anger fade from my face.  I said, “Did you just say yes Ma’am?”  He nodded his head and looked down at the floor.  I said, “Well, well, seems Dear Old Daddy is a submissive pussy.”

He looked like he wanted to cry, but I didn’t care.  I figured if I could not have cold hard cash, then he would have to work it off.  He owed me a lot more than what he tried to give me.  By the time I left he was dressed in some of his wife’s clothing that she left behind begging me to make him my very own Sissy Bitch.  He also had his first taste of man cunt insertion.  He wanted to cum so badly but he isn’t allowed to until he can get me the money he owes me.  I fucking HATE babysitting, but I love Babysitter phone sex, especially when it involves a fantasy like this.

Sissy phone sex with Charlie

I got a new playmate this weekend, and we had so much fun. I ran into this man while shopping and he was looking really embarrassed supposedly trying to buy some lingerie for his “wife”. Right!!! I saw the sizes he was looking at and they were OBVIOUSLY for his girly tendencies he keeps secret.

 

So, I cornered him outside the store and told him he had just won a free Sissy makeover! He was beet red and stuttering, and I loved every second. I told him we were going over to the M.A.C. counter and we were going to make him up like a sissy. Then I was going to make him drive us to a hotel across from the 24 hour gay club.

We got a sleazy hotel room and I got him to dress up and become a Sissy for me. I’m a Princess and only hang out with other Princesses so dress like slutty princess. I escorted my Sissy over to the club and hooked her up with a lot of cock. I had my sissy swallowing cum and had her sweet cherry popped.

Who’s next?

 

My Sissy phone sex slut Daddy

My daddy is completely wrapped around my finger, and is a really pathetic sissy phone sex slut. I like my sissy’s to be pathetic after all their manhood is none existent once they start wearing pink frilly undies.  It all started when I was a young sweet little thing and very mischievous. I would persuade my daddy to let me dress him up and put make-up on him. I would raid my mother’s drawers and make-up to dress daddy up with.

So you see I started shape my sissy slut early on and I love that he still lets me play dress up and make him my sissy phone sex slut. I started the really naughty play a few years ago as I was exploring sex. I wanted daddy to be a part of sexual exploration and he didn’t seem to mind. He was willing to let his little princess use him as I wished to use him. We had gone on a vacation together just the two of us when things took a new level.

While we were in the hotel room taking a nap, well I was napping anyway when he snuck out. Daddy had gone down to a sex toy store and picked up a few goodies. I awoke when I heard him coming in the room. I was half asleep and confused as he put a few shopping bags on the bed. He had also gone to Fredericks of Hollywood and got some things for both of us. I started peeking in the bags and became really excited. Smiling at my daddy asking if we were going to play dress up now. I could see he was very excited also.

Pulling out all the goodies I immediately started sliding my cotton panties off and my little t-shirt off as well. I was getting all giddy inside and found the stuff for me to dress in and what I’ll be dressing my sissy in. Then what really got me excited is the strap on cock I get to use on my sissy phone sex slut. Oh what a good little sissy phone sex slut I’m going to have!!! Look at these sweet frilly pretties I get to dress daddy up in!

We went and had a shower together before we started our dress up fun. I had my sissy phone sex slut daddy sponging my sweet little body clean. I made him suck my clitty and drink my golden nectar while in the shower. He is such a good sissy phone sex slut serving me so well, just as every daddy should.

Once out of the shower we got dried off and daddy rubbed my body oil all over me. I in turn also rubbed daddy down with some pretty scented oil. Daddy then sat on the toilet seat so I could make his sissy phone sex slut face all pretty. I love putting make up on my sissy phone sex slut daddy.

Daddy is all pretty now with his face all made up to be my sissy phone sex slut  and all we need to do now is dress her up. I loved the frilly pink teddy and matching panties for sissy phone sex slut muffin daddy. He even picked up some sexy pink thigh high fishnet stockings to go with her sweet  sissy phone sex slut outfit. Oh she’s so pretty now in all her pink and lace. Such a tasty sweet sissy phone sex slut I have.

I put on the leather bustier and black fishnet stockings with a sweet pair of black lace panties to finish it off there are a pair of black stiletto heels. And my favorite part of it all, my new shiny purple strap on cock which makes controlling my sissy phone sex slut all the more!