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