Showing posts with label sissy. Show all posts
Showing posts with label sissy. Show all posts

Thursday, November 5, 2015

Two Dommes and Three Subs








Back in August. I went to a BDSM Playparty. Just a small gathering. Myself another Domme Miss Rose and 3 male subs. It was held at her house. Her subs I will call sissy M and sissy T. I took along Freddy with me. I arrived with Freddy and they were already dressed the sissies already serving their Mistress in many ways. Freddy and myself went to the bedroom and changed . Having a few kisses and cuddles while we changed. This was Freddys first play party and judging by his erect cock he was very excited. The panties id put on him were straining in the front. We went to join the others in the living room and Freddy immediately got on his knees and started to pleasure me. So, the scene you should have in your mind is myself and  Miss Rose sat on the sofa. Freddy between my legs, Sissy M between hers and Sissy T suckling her breasts and sometimes coming over to give mine some attention.
After a couple of orgasms and some wine we decided to take the play to the bedroom.
Freddy and Sissy M lay next to each other on the bed. We began by wrapping their cocks and balls and torturing them just a little. Then I did a demonstration of sounding on Freddy. She wanted to learn so I spent a little time teaching her. ( she has since bought a sound and now uses it on her subs ).
Then they were ordered on their knees and were spanked. Naughty boys and Sissys need to be spanked. Then she swapped Sissys and Sissy T got on his knees and we both spanked him. Then I put on my gloves and gave some to her. She had never done a prostrate massage. So another demonstration was needed. Then we used some anal toys on them. She had an interesting inflatable dildo with an adjustable vibration control. I tried it out on Freddy and it drove him wild. I loved it. I have since purchased one .Then with Sissy M's help we put on our Strap on's. It was quite a sight us stood next to each other wearing them. Then we both entered our subs asses at the same time. Freddy had wanted to try something but was really nervous. Hes not bisexual, but feels bi-curious . He wanted to have a man stroke his cock. So, when he was kneeling there at my mercy I told him Sissy M was going to stroke his cock. I could feel his body tense up immediately but he allowed him to do it. He just did it for a minute or two. Freddy admitted after it was a weird experience to know a man had his erect penis in his hand. ( in the near future Freddy wants me to take his hand and have us stroke a mans penis together).
Then we washed off the dildos and changed subs. So,she was with Freddy and I was with Sissy M. It was such a turn on watching her enter Freddy and he admitted he was aroused watching me enter Sissy M.  ( this at a later date turned into a chat about getting together with swingers. That's another story or two or three ). Then she ordered her sissys to play with each other while we watched. They are both bi. They stood in front of us sucking each others cocks and fucking each other, while we lay on the bed and Freddy gave our pussies some attention. Then it was time for Freddy and myself to leave. So I pushed Freddy onto his back on rode his lovely cock. Her subs either side of me suckling my breasts. It didn't take long for him to explode inside me. When we were dressing after he said hed never had sex in front of other people and was surprised how exciting it was having people watch.
Ive been invited to a big Play Party on November 14th. So, stay tuned for that .

Monday, August 10, 2015

Pantyboy Joe


Picture is from http://panty-boy-illustrated.blogspot.ca/




Pantyboy Joe is one of Mistress Anna's online subs. He contacted me through my blog about 6 months ago. He had an interest in being a pantyboy but didn't have the courage to begin. Mistress Anna sent him out shopping as his first mission to buy panties. It took him a couple of tries but eventually he bought then. Then he had to put them on and take photos for me. Poor pantyboy has nothing to put in the thong. His cock is so tiny and useless. Its more like a girls clitty. He really does look like a sissy. He was given further missions to masturbate and cum for me on demand and other times told to be either chaste or sometimes able to touch but no orgasm. He knows his cock and cum belong to me now.

Over the past few months he has progressed to also wearing a bra and hose and last month he had to eat his own cum for me. I think my sissy pantyboy is making wonderful progress

Sunday, July 5, 2015

Sissy Talk

The other day,i was chatting with db and we got into a different scenario in our role playing.Normally i don't allow db to touch me in a sexual way.But,yesterday i allowed him a  rare treats.To suckle my breasts .
Normally i don't allow him these liberties since he's my sissy sub and i like to just dress him up all girly. Then humiliate him and tease and abuse his  anus and cock.
This an outfit like one i might wear when i bathe db .Before dressing him in her pink silky panties and dress.Transforming him into my sissy.





Interesting book by Colin Milton you may want to read.

http://www.amazon.ca/Mummy-Me-Colin-Milton-ebook/dp/B005GHMF00

Thursday, May 7, 2015

Taking freddys anal cherry




Today was the day freddy had been waiting for. It was the day Mistress Anna would finally take his anal cherry.
 We embrassed warmly when we met and as always he likes to pleasure his Mistress orally to a number of orgasms before she does anything to him.
After,he'd finished I restrained him spread eagled to the bed and began with some erotic teasing with the ice and heat. This was followed by the needling. Today, though was also another first for freddy. His first C & B torture. I promised to take it easy on him. I poked his cock and balls gently with the needle. He was pulling hard against the restraints and I'd constantly take him to point where he could take no more then stop. Then I'd rub his C & B with ice to cool them down and numb a little before doing it again. Then I took my cane and slapped his inner thighs and a couple of gentle ones to his cock.After I felt he'd been sufficiently punished I released him from his restraints and told him to sit on the edge of the bed. I went to the bathroom and returned wearing the strap on.

I ordered freddy to his knees and told him to suck my cock.I told him to take it deep in his mouth. I told him he was a cock sucking slut and pulled his hair as I told him to take it deeper into his mouth.
I ordered him to get on his knees on the bed and I restrained his arms to his legs so his ass was nicely presented to me.I lubed up my fingers and the cock. I slowly used my fingers to penetrate freddy until I could easily get four fingers up him. Then I placed one hand on his hip and used my other hand to guide the cock into his ass. I told him he was now my anal slut bitch and I owned him. I grabbed both hips with my hands and penetrated him deeply. I could hear him moan and gasp as I did it. Then I reached around and started to stroke his cock. We did this for some time , but I always stopped before he came.
Then I released freddy from his restraints. Turned him onto his back and straddled his erect cock. I rode his cock until we both cum. I don't normally get quite so intimate with my subs. But, I was having a sexual relationship with freddy before we started the domination so I'm comfortable incorporating both.

Thursday, April 30, 2015

More Intense training

I've been seeing freddy now for 5 weeks. I must admit it has been going amazing. Far beyond my expectations. He was nervous and a little resistant when we began. But, after Saturday's session he's now begging me to do things.
On Saturday I decided to intensify the training. I started by blindfolding and restraining him on his knees with his hands restrained behind his back. I began with the ice. Firstly his lips, then his neck , then slowly all over his body.But, not his cock . Instead his inner thighs and the area between his balls and anus. I followed this by heat and then back to the ice. He was getting so aroused I had to grab a towel for the floor. The pre cum was running out of his cock like a stream.

Then I introduced freddy to needling.( pricking the skin with a sharp object ) He later told me this part was very intense and he wants me to do it harder next time. Then I started slapping him with a cane I'd purchased the previous day. I spanked his bottom, thighs and even a couple on his shoulders.
 I released freddy from his restraints and led him blindfolded to the bed. I pushed him onto his back and restrained his legs to his arms so his genitals and anus were on full display for me. I began by using the ice on his cock and balls. then I took his cock in m y mouth to provide the heat. I did this a number of times before moving my attention to his anus. I used my gloved fingers to penetrate him. Going in as deep as I could with four fingers. Then using fingers I began to stroke his prostrate. My other hand then continued with the ice and warm mouth. I have never seen a man spasm and ejaculate with such intensity. He told me after that was the single most erotic intense orgasm he's ever experienced in his life.
Now freddy wants to experiment with everything. In our next meeting he is going to finally take his Mistress' cock.

Mistress Anna with her cock







Tuesday, April 14, 2015

Disiplining db

 
 
 
 
I felt that lately I had been a little lax in db's discipline. So, i decided he needed to be taken in hand and reminded who was in charge. I ordered him to strip naked and to go and stand in the corner facing the wall. I left him stood there for 10 minutes. I sat in a leather armchair dressed in my black lingerie and stockings. Then he was commanded to crawl back from he was stood, kneel in front of me and masturbate himself. But , he can not cum. I just wanted a little amusement. I could tell by his hand rhythms that he kept slowing down obviously trying to stop himself from having an orgasm. It made me smile.

I instructed him to seize touching and return to the corner. This time I left him there 15 minutes.
After 15 minutes I stood up and grabbed db by the ear. Pulling him by it to the bed. I put a pillow under his bottom and pushed his legs back. I put on my latex gloves  applied lube to his anus and onto my fingers and thrust them deeply into him. My fingers penetrating deeper and opening him up. My smiling thinking the feeling of ownership he must be feeling knowing I'm inside him. I continued for 10 minutes then stopped. Removed my gloves and told him to put on his panties. No orgasm for you today db.

Sunday, March 29, 2015

Dirty Panties

Now, you saw Mr. Wonder featured in an earlier post wearing my panties


 
 
Well he got very aroused wearing my panties and got the crotch wet with pre cum
 
 
 
 
So, I rubbed the pre cum covered crotch over my nipple
 
 
Then I made him suck it off my nipples
 

Wednesday, March 25, 2015

Men In Panties










Henry was 50 years old. He'd always had a fetish for wearing ladies panties. He had 2 pairs. A pair of pink silky ones and a black lacy pair. He would wear them under his work suit when he went to work and under his jeans when he had leisure time. Henrys only problem was that his girlfriend didn't know. He was always careful to take them off and hide them when he knew she would be visiting.

This arrangement worked perfectly until Matilda brought up the subject of moving in together.  Henry had a plan to hide the panties in the garage and just wear them when Matilda was out. This worked well until one day Matilda came home early and caught Henry admiring himself in the bedroom mirror wearing them. Henry was very red faced and Matilda at first shocked.

Then Matilda grabbed him roughly by the hair and dragged him to the kitchen. She made Henry stand there whilst she took a wooden spoon out of the drawer.  She pulled out the kitchen chair ,grabbed Henrys hair and pulled him over her knee as she sat down.. She then proceeded to spank Henry with the wooden spoon. Telling him he was a naughty Pantyboy for putting on panties without permission. Henry's bottom was so red and painful. Every spank sent fiery pain throughout his body.

Matilda then ordered Henry to go upstairs strip naked and sit in the corner of the bedroom. Henry sat there a long ,long time not knowing what to expect. Henry heard Matilda go into the bathroom ,then she summoned him. On entering the bathroom he saw something in Matilda's hand. She said Henry your a sissyboy and only real men have pubic hair. So,
she proceeded to shave Henry bald, then commented that now he looked like a slutty sissyboy and that he was hers to use as she pleased. The next morning Matilda told him he had to dress in her used dirty panties. Your just a dirty slut Henry and so you have to wear dirty slutty panties. So, Henry did that day and every other day after.


Mr Wonder wearing my Panties

Wednesday, March 18, 2015

Mommy Anna's Big Baby Boys


Now i know some you would like to be my big baby boy and have mommy take care of you.
You'd like mommy to bathe you in some warm soapy water washing every little inch of you. Then lying on the bed while mommy rubs lotion on you and powders your cute little bottom. Then mommy will wrap you in your comfort blanket , put your head on her lap and breastfeed you.
After you feed mommy would dress you in special sissy clothes like the ones in the photos.


Well i found a wonderful site with clothes on it called Christine's Sewing Room. She makes custom made Sissy and Adult Baby Clothing. You can either Google to find or email me for link








Tuesday, March 3, 2015

Sissy Training - Masturbation Schedule

Part of sissy training is a masturbation schedule.

Sissies must always remember that masturbation is a privilege to be enjoyed at my discretion.

I often set db a schedule since we don't live together. He is required to check in and confirm he has adhered to it. Usually he is allowed to climax no more than 3 times a week. Sometimes he is allowed to stroke his sissy cock, but must stop before climax. Other times he must refrain completely. db must always be wearing his sissy girl panties when he masturbates. This is to remind him his cock belongs to Mistress Anna and is NOT his anymore.

Also,db must always pee like a big girl. No standing up to pee like a real man just sitting like a sissy girl. 

Failure to follow the schedule ALWAYS requires me to administer punishment later. My punishments vary from pulling down his panties and spanking him, to making him lick my dirty shoes clean or even violating him anally with a humiliating object like a candle or cucumber.


This is an example of db's current schedule if you sissys want to follow it

Mon, Wed ,Fri -  You are allowed to masturbate and climax
Sat, Sun - You may may stroke your cock but NO climax
Tues, Thurs - No touching

Wednesday, February 25, 2015

Sissy Talk

One  of my favourite things to do with db is to dress him like a sissy girl. I dress him in panties,silky gown ,fluffy pink slippers. Then I put make up on him and a wig. Then of course I call him a girly name. For the post I will call him dolly.
Once dolly is dressed shes then allowed to attend to her Mistress. She can help me to dress. Putting on my stockings and pulling on my boots. Sometimes dolly will be instructed to pleasure her Mistress with her tongue . If she doesn't do a good job I put her over my knee,pull down her panties and spank her with a paddle.

Othertimes shes instructed to massage my breasts with a nice sensous oil. If she gets an erection she knows it will get slapped HARD. She often gets an erection doing this and often starts to whimper when she realises im going to slap her erect cock.

On another subject we have discussed the possibility of getting a chastity belt . We looked at a few on some fetish websites and once we decide on one then we'll need to discuss how to incorporate it into daily lives.