Summer is a natural!

Continued from: Summer stayed the Night

"Mistress tells me you would like a more slender waist, some development of your hips and a more rounded butt?" 

Summer, matter-of-factly said to Andrew, her first male client.

"Yes Miss Summer", he squeaked out in shame. 

"Mistress also tells me that you want a more feminine figure to fill out the sissy clothing she forces you to wear?"

Andrew blushed deeply and said, "Yes Miss", and knelt at Summer's feet. 

"Ahhh, very good. You two have met". Mistress Andrea proclaimed, as she clicked into the gym. 

Andrew quickly moved his lips from Summer's knee socks and planted them on Mistress' high-heeled boots. 

"Mmm, good boy!" She purred. 

Mistress kept him down in a kneel and used his back as a seat. She began talking to Summer as though he wasn't even in the room. 

"Summer, Andrew here first booked a session with me about six months ago. He has proven to be very devout and loyal. Five months ago I started to ween him off orgasms with his penis, when I introduced a chastity device. He hasn't had an orgasm in about three months. He is aware that if he doesn’t obey your every command, he’ll be in very deep trouble with me and get another month added to his chastity sentence. 

He already earned an additional month for fussing when his hair and make-up lady came over a few weeks ago. 

"Here, hold his arms Summer. I’ll pull down his pants and show you his locked up little clitty. We need to get him into a more appropriate workout outfit anyway".

Summer inspected the device curiously, looking at the two different locking mechanisms. 

"Does it hurt him Mistress?" 

"Not really, only if he tries to get an erection, which it appears might be occurring now. The device discourages erections and prevents him from masturbation, cumming and penetrative sex".

Both women giggled. 

"I'll leave you to it Summer. There's a female workout outfit in the locker over there, along with some other helpful items you may like to use on him".

"Certainly Ma'am", Summer excitingly declared. 

"First things first young man, get over my lap right now!" Summer barked. 

"If you're suppose to be in female workout attire then I expect to find you that way, not waste my time having to change you". 

Summer spanked quite hard for a small-statured woman. She had his cheeks glowing red in no time. 

"Get the outfit from the locker and put it on". Summer ordered in a no nonsense tone. 

"Ohhh Miss Summer no!" 

He pleaded with her, when he saw the two-piece spandex and knee socks. 

"That's better!" Summer said while chuckling. 

"What else did you see in the locker Andrew?" Summer hissed. 

"Please Miss no! 

"I asked you a question", Summer spoke, now becoming irritated. 

"It was a strap-on harness, with a realistic looking dildo Miss". 

He pleaded with Summer as he fell to his knees".

"There should be some high-heels in your size also. We need to work on your walk and teach you how to sway your butt like a girl". 

"Would you like the cock first, or the high heels Andrew?"

Summer didn't let up, she didn't allow him room to breathe. He was faced with the predicament of having to select his own humiliating form of training. He knew if Mistress found out that he disobeyed Summer, he'd definitely have another month added to his chastity sentence and likely receive a severe spanking. 

"The cock Miss". He mumbled out. 

"The cock what? Ask me nicely!"

Ohhhh Summer was good, she was a natural at dominating pathetic men!

"May I please have your cock Miss Summer?" 

"You certainly may my little slut", Summer taunted. 

Mistress Andrea walked in to check on the progress. 

"Oh what an eager little cock slut!" Mistress gleefully chirped. "Do you wish that was a real cock my sissy gurl?"

Andrew responded with some gagging head bobs and tried to say, "Yes Mistress".

"Summer don't forget to fuck our gurl in her sissy pussy". 

"Yes Ma'am", Summer replied. 

Summer attached a ballgag into Andrew's mouth and forced him to watch himself in the mirror, as she slid her cock into his ass. 

She fucked him good and hard, before getting him into a doggsytle pose on the weight bench. 

"Are you ready to walk in high-heels for me now, you little bitch?"

"Yaash-plause Mich", as he did his best to respond through his gag while Summer continued to violate him. 

Summer finished up with her strap-on and got the poor sissy slave onto the treadmill. The dildo attachment slipped into his ass with ease, having just been fucked. The dildo post held him in place as Summer helped him step into some high heels. She then attached a bondage yoke and stood back to enjoy and giggle at the spectacle. 

"Good girl", Summer praised. "Sway your hips just like that, wiggle your butt". 

Poor Andrew was now sobbing from the humiliation and drooling from his gag. Summer had officially broke him, or perhaps just broken him in. She set the treadmill for 20 minutes and went to sit down. 

When the timer ended and the treadmill stopped, Summer put the sissy Andrew in timeout in the corner, leaving the gag in and the heels on. She called Mistress to say their first training session went well and that they were all done. 

"Finish up anything you have to do and shower up Summer, thank you for your time and your help". Mistress praised. 

"Leave the sissy where she is, I'll come get her later. If she moves, another 20 minutes on the treadmill please". 

"Yes Mistress Andrea", Summer replied. Andrew heard the full, embarrassing exchange from the corner.

Summer finished up parts of her own workout, before hitting the shower. 

The sissy slave spent about 45 minutes in his cornertime position. Spanked, feminized, degraded, humiliated and fucked. Little spider strands of pre-cum dripped from his chastity cage as the tears dried on his face. 

Summer, was an absolute natural at this, it came easy to her. She was starting to love it!.  

Continued in: Mommy's Sissy gets a new Name

Summer Stayed the Night!

I am sure this will not come as a shock to anyone who read the details of my first training session with Summer, but she ended up staying the night. Train the Trainer. Score!!

She didn't know this yet but she owed me a debt. She orgasmed four times while I was fucking her tight pussy in the gym, five if you count the additional one in the shower. 

That means she owes me TEN! Orgasms. I maintain a 2:1 orgasm ratio for female submissives, a 5:1 ratio for male submissives and sissy slaves might never orgasm with their little peenies ever again, while under my control. 

These are the rules of my "facility". My clients need to understand that they are a vessel for my pleasure, and should be quite grateful if they receive any pleasure of their own. 

Summer, however, is very different than most. Although she is slightly submissive, I do not consider her to be one of my "owned" slaves nor is she a client. She looks at me like a protector, dying to be praised by me and have her beauty and sexuality qualified.

Summer is a Flight Attendant, which means she is no stranger to looking sexy, no stranger to hosiery and heels. If you have ever had the pleasure of seeing a crew of Flight Attendants, power-strutting through a terminal, in tow behind the pilot, they absolutely ooze sexuality and femininity. They might be walking behind the pilot, but there is a feminine dominance about them, their strut, their attire, the way they command the cabin and "mother" the passengers on a flight. I was thinking about all of these factors while Summer was going down on me. I might ask her in the morning, if she wants to be trained as a Dominatrix, under my tutelage and control. 

But for now, lets get back to our evening together. 

My cute little pet asked permission to peel me out of my high heels. When she did, she cradled my hosed foot in her hand. She nibbled on my earlobe and asked if she could start at my toes! What a little doll! It is usually all the silly boys and sissies who lick and suckle on my feet. It will be nice to feel a soft, female mouth against my stockings.

I could feel her little button nose, run the length of my hosed foot, taking in the lingering scent of my recently removed stilettos and the lotion I use on my feet. Her tongue was magical and delicate, as she licked the pads of my foot, followed by my tender arch. This sent shockwaves directly to my clit. 

I ushered her down into more of a submissive posture on her hands and knees, so she could kiss the tops of my feet and my burgundy, painted toes.

I asked that she remove her bra and panties, to which she eagerly replied, "Yes Ma'am". 

She was learning. 

I was dropping little hints all the while, teaching her about her potential, future role. I was coaching her on how I like my feet pleased and positions suitable for chastity boys, making sure they can see what they lust for, but cannot have. All of my sissy slaves are pussy free, straight males, who are kept in chastity 24/7. They get my feet and asshole only. If they want a taste of my pussy, it will be off the cock of one of my male slaves, who has just been inside me. 

"Does my asshole look pretty Summer?" I purred to her, giving her a good vantage point.

"Ohhh yes Mistress!" She groaned, with my nylon covered toes still in her mouth. 

"Would you like to taste my asshole Summer?" 

"Oh fuck Mistress, may I please Ma’am!?” 

Summer massaged her thumb into my pussy while her fingertips grazed my clit. I could feel her warm breath on my anal opening, right before she gave me a lovely French kiss, directly onto my asshole. I gasped, as goosebumps consumed my entire body. She continued to kiss and lick, eventually plunging her tongue deep inside my bottom hole. 

"Good girl!" I hissed from my lips. 

I laid her on her back and continued to enjoy the sensation of her tongue up my butt.

Pretty soon I would be reaching for my Hitachi wand to orgasm onto her chin. I love cumming with a tongue up my ass. I love to clench and squeeze a pointy tongue with my cute little pucker when I cum!

Gawd! It felt so good. 

When she upgraded to my pussy she was just as skilled and eager! I continued to praise and verbally reward her. 

I gave her some attention and edging too, until she was begging to cum, but I didn't allow it. I heard her whimper, likely pouting, as she huffed in frustration, puffing air onto my soaked pussy. She had been previously warned that she’d be sleeping in a cage beside my bed tonight, if she came without permission.

Jesus, she was so delicious though! Summer's pussy tasted like gummy bears! 

I edged her with my tongue and fingers until she could barely stand it. I continued to deny her orgasm, while she had given me a total of four, in a variety of positions. I even counted the Hitachi orgasm with her tongue up my butt, as one taken away from her debt. 

While I was soaking in the tub afterwards, Summer dutifully got back to my feet, and rolled each of my toes between her soft lips, gently sucking them.

"You still owe me six orgasms young lady!" I teased. 

Summer giggled onto my toes which tickled and caused me to wiggle them. "Yes Ma'am, of course".

"Are we doing more gym training in the morning Ma'am?"

"Yes sweetheart. I'm going to show you a nifty little addition to my treadmill, to help train the sissies how to walk in high heels. It's quite the predicament". 

I visualized in my mind, how sleek and sexy Summer will look on the treadmill, as we finished up my bath and slipped back into bed. 

"Like predicament bondage Ma'am?" Summer pillow talked-me. 

"Something like that huni, yes. There is a dildo-shaped object that holds you in place by your pussy". 

I visualized how hot this will be to watch. That juicy, figure-skater arse of hers, swaying with the motion of her strides. All while being tormented and impaled on the dildo attachment. 

"I look forward to it Mistress. For the sissies I assume this goes up their bum right?”

“Yes Summer. They are forced to walk in heels for me, dressed like frilly little girls, with the penis-shaped object up their ass”. 

Summer let out a devious little chuckle and snuggled in beside me.

“Goodnight Ma'am".

"Goodnight sweetheart", as I kissed her on the lips.

Mistress Andrea

xoxo

Continued in: Summer is a Natural

 

  

Train the Trainer

 Mistress Andrea certainly keeps herself in top physical condition, it is a bit of a requirement for her unique work as a Dominatrix. However, she was noticing that some of the husbands and boyfriends of Willow Creek were a bit doughy. They definitely will not be able to fit into the feminine and frilly clothing she has planned for these silly, sissy boys. That being said, Mistress went and found herself a 25-year old, ex-figure skater with Mommy issues, the cute and bubbly Summer Holiday!

Look at this little sniper!

Before Mistress could unleash Summer on some of her clients, she thought a familiarization session should be in order. This was Mistress' home gym yes, but it had some special features. It was no ordinary gym when you look closely. 

Summer certainly had the aggression level for her new role. She just wasn't 100% sure about the new types of motivation Mistress was telling her about. Whipping, spanking, cock and ball torture, feet and ass worship...this was all new to her. 

Summer went on to try some of the other equipment, all while glancing around the room and noting that some parts of the equipment had been sexualized, or bondage implements added. 

When she saw the electo-sex prod and the single-tail whip, she started to understand what would be required of her but didn't know where to start. 

Summer, using her most cute and submissive tone, politely asked Mistress if she would run her through a workout session using some of the new "stations". She said it would help her understand what the sissy male slaves would endure. 

"Of course sweetheart", Mistress happily obliged. "Let's start with the deepthroat trainer. You would use this station to humiliate the silly boys and giggle at them while they struggle to please you. Remember to rate them on their cocksucking abilities and belittle them about how much they love sucking cock”.

"If their nose can dab the pressure plate at the base of the training dick, the device will record this. You may wish to reward a slave for a high score", Mistress went on to describe. "If their nose can't reach the plate, you may need to ah-hem...motivate them. Would you like to try Summer?"

"Ooooo yes please Mistress!"

Summer eagerly got down on her knees, like she's done this before, and took the training cock into her hand and guided it into her mouth. 

"It looks like you could use some more intensive training also Summer", Mistress snipped. "Your nose needs to hit the counter to record a successful suck". 

Summer gagged and wretched loudly. "Mistress I can't reach it", she panted, with slobber cascading off her lips.

"Perhaps YOU need some motivation? Go kneel by the mirror and get those pants off. Hold the riding crop in your palms for me", Mistress commanded. 

"That's a good girl!" 

Summer could feel those words electrify and caress her pussy. Ohhh how she loved being called a good girl. 

Mistress gave Summer twelve lashes of the riding crop on each bare bottom cheek, which she made her count aloud. 

"Is this how you want me to motivate your clients Mistress?" Summer yelped out as her whipping concluded. 

"Absolutely!" Mistress Andrea replied. "Now lets try the exercise ball. I can see your pussy has started to provide the lubricant already". 

Summer blushed deeply but Mistress was right, something about the vulnerability of this situation, the embarrassment, giving up control and the pain...it was making her so aroused! Summer slipped easily onto the exercise ball and groaned out loud when the dildo entered her. 

Mistress helped to press on Summer's shoulders so the bouncing action provided her with a good fucking.

"Now remember Summer, when you're doing this with the sissy boys, the training cock will be right up their ass. Be prepared for a lot of whining and crying", Mistress coached her. 

Summer moaned out and gasped, "Yes Mistress, my gawd I'm so turned on!!" 

"Can we start back up in the morning Mistress? I need you to FUCK ME so bad right now!"

"With pleasure sweetheart". Mistress purred, as she reached for her strap-on. 

Mistress took Summer around to every piece of workout furniture available, and fucked her on them.  Summer was ravenous, high energy and had cum three times so far. 

The two of them were actually breaking a full sweat now, Summer was quite the little handful. 

After Summer's fourth orgasm Mistress pulled out. They were both out of breath, painted in sweat and smiling from ear to ear.

"I think I'm gonna like it here Mistress", Summer said, still breathing heavily. 

"Time to hit the shower huni?" 

"Yes Ma'am, just don't forget the strap-on". 

Mistress shook her head in disbelief. "What a little wildcat!” 

Until tomorrow...

Continued in: Summer Stays the Night