The story of how I built my harem of lawyers. Still twelve years ago... Diana continued.
One thing I quickly learned about Diana was that when she set her mind to a goal, there was no stopping until she was the very best at it. She took this attitude towards everything in life from her studies to sex. So while my beautiful Latina trainee was relatively new to the kink world, she had poured so much effort into learning about the lifestyle that it was hard to believe that she was still pretty green. Her energy and desire to learn were infectious. Giving her new experiences and testing her boundaries became my top priority for Diana's training.
One of my training techniques was giving Diana homework to do on the days I was out of town. I would typically give her an assignment on a Monday when I left and she would complete it by my return on Thursday. Homework was never easy especially because Diana started her summer internship at a lobbying firm on K Street the week after my acceptance of her as my trainee.
That week, her homework was to be able to put her cuffs and collar on within 5 minutes. She obviously liked my assignment because she texted me begging to be allowed to cum from masturbation several times a day and sent me pictures of her in her collar or wet fingers in her cuffed hand to thank me for her orgasm. Needless to say, there were more than a few times that I had to stay seated in the conference room I was camped out in until my erection died down to avoid any HR complaints.
The favorite of my assignments was to learn the twelve slave positions I utilized for my protocol play. By that point, I had modified my orgasm control rules to allow my horny trainee to jill off whenever she wanted but to thank me for each orgasm to avoid too much distraction during the day. I got videos of her practice sessions on Monday with 2 "thank you's". On Tuesday I got pictures of each position taken throughout the day including positions 3-7 that were taken serendipitously during her time at her internship. The best part of that day was getting post-orgasm "thank you's" when I knew she was at work.
On Wednesday she had one of her kink friends, Baby, over after work to do another practice session. Around 5 PM Pacific Time Diana called me. "Papi, Baby is being such a good study partner. I am so horny, can I play with her? Pretty please, Papi," she begged.
I knew Baby before I met Diana. Baby was her scene name, coming from both her diminutive stature and she was very much a "Little" at heart. In the kink world, "littles" are generally into age play and paired naturally with Daddy/Mommy type Dominants. When we met, she was in a long-term relationship with a Daddy. After their break up we never dated but enjoyed a cuddle at munches and parties now and again. She was a tad too bratty for my tastes for a partner but a sexy little girl by any account.
"You have been such a good girl, I'm going to say yes but I want to hear you have your first orgasm. Put me on speaker," I ordered. When she complied I said "Baby, I want you to rock her world for me. Can you do that?"
"Oh my God, Sam. I will do my absolute best," was Baby's reply.
At that point, I heard the sounds of kissing and the rustling of clothes. Then came Diana's signature moan that let me know that Baby was sucking her nipples. That was followed by a deeper groan from my Cuban pet and Baby's exclamation, "You are so WET!"
Diana confessed, "Doing the positions for you got me so turned on I thought I was going to cum if you made me do number twelve again. AY SI!"
"Tell me what she is doing to you Dee," I said.
"She is fingering my little pussy, Papi," she narrated. "Ay Dios mio, now she is licking my clit." I could hear her groans getting louder and more frequent. Frantically she asked, "Papi, please may I cum?"
"Cum for me, Dee," I replied and my little screamer went into overdrive. My ears rang from the yells and grunts that poured from my earbuds. Then I heard the sounds of kissing again. "Where are your manners, little girl," I asked
Diana quickly recovered "Thank you, Papi. Thank you, Baby."
"Better. I'm going to let you ladies have your fun now without me, " I told the pair. "Dee, for having to be reminded about your manners you only get one more orgasm tonight. Baby better get as many as she wants. Is that understood?"
"Yes, Papi" Diana replied. I could almost hear her pouting on the other side of the country.
Laughing, I said my goodbyes and hung up. An hour later I got a "thank you" from Diana along with an "I miss you, Papi".
That Friday night we attended a party at a local rope studio. It was the perfect opportunity to test my trainee's true competence in her slave positions. Early in the night, I had her take off her panties so I could have easy access to her pussy all night. I used every opportunity I had to tease my gorgeous partner a few times, shoving her against the wall and using my fingers to get her right to the edge.
I stepped up the edging by giving Diana a wireless remote control bullet vibrator to put in her pussy. Throughout the night, I took the opportunity to keep her on her toes by turning on the bullet while she was talking to someone and again as she browsed a vendor's table. The Latina's eyes would get wide and she bit her lip as she suppressed a moan. When I would turn off the vibration, she would turn to me a shoot me a withering stare.
It was too much fun toying with my trainee. To switch things up, I asked Diana to refresh my drink and snuck the remote into the hand of Baby, who arrived at the party about an hour after we did. The look of shock on Diana's face when the buzz deep in her pussy started despite my hands being empty, made my week. Watching her scanning the room to figure out who had the remote was worth the price of admission.
When she finally figured out it was Baby, she ran up and bit her on the shoulder. "You bitch," Diana yelled and Baby just laughed. What Dee didn't know at the time was that Baby and I negotiated and planned out this scene together.
"Dee, is that any way to treat a friend," I asked.
"No, Sir," she replied looking down.
"Well then, little girl, I think we need to make it up to Baby. Don't you?"
Diana nodded sheepishly. "I think it is time to do our scene and Baby is going to help me. Aren't you, Baby," I asked. Baby nodded and giggled in affirmation. "Get her naked, Baby," I ordered and soon Diana was standing before me with just her collar and cuffs on.
I took a bundle of silk rope and tied a basic hishi karada body harness on my petite Latina trainee. The harness looks like a rope bodysuit with a series of diamond-shaped sections running down the front. I added a twist to this harness by tying square knots that lined up just above and below her clit. When I was done, the rope was tight between her legs and cut between her sexy Cuban booty like a thong.
With my tie done, I turned to Baby "Time to test Dee's knowledge of her positions. You are going to call out random position numbers and she will have 5 seconds to get into the proper position. Since you were Dee's practice buddy this week, if she messes up she gets one strike from my crop but you get two. Now take off your skirt and get down on all fours in front of Dee."
Baby dropped her skirt and handed me the remote so she was now standing in front of me in her black tank top and cheeky black boy shorts. She handed me the remote and I directed her to start quizzing my trainee.
"2," called out the little pixie. Diana dropped down with her knees on the ground, ass up, chest pressed to the ground with her arms stretched in front of her. The little gasp she made getting into position let me know that the happy knots I tied in the rope splitting her legs were doing their job.
"Oh no, Dee! An error in your first position! Your palms should be facing down, not up," I reprimanded. My crop came down with a crack on her perfect ass.
"One! Thank you, Sir," she responded.
"Now look at Baby," I ordered. Diana raised her head and looked at Baby's green eyes. I brought down the crop on each of the diminutive blonde's ass cheeks in quick succession. Baby cried out then sucked in air between her teeth, she was also a bit of a pain slut.
Diana was determined not to mess up again but as she went from position to position the happy knots would through her neat pink pussy lips and over her clitoris. After 8 position changes, I could tell my little trainee was having trouble concentrating. She slipped up in her positions 3 more times prompting me to discipline the two lovely girls at my feet. Compounding issues for Diana, my crop strikes were turning her on even more. I needed to find a way to get Diana to cut through her physical pleasure and concentrate to complete the task at hand.
"STOP," I commanded. "Baby, stand up and turn around. Look at what your mistakes have made me do to poor Baby's behind. Do you want Baby to hurt more," I asked my trainee.
"No, Sir," Diana replied.
"Good because from now on I'm calling out positions and if you mess up, Baby is going to get all of the punishment. If you don't mess up we are going to make you cum so hard. If poor Baby here gets punished for you, I'm going to make it up to her by giving her orgasms tonight while you sit in a corner and listen," I told her.
My beautiful trainee stood before me wearing only her collar, cuffs, and the red silk hishi karada harness. Her b cup-sized breasts were framed by the rope. They were capped by her thick milk chocolate hardened by her arousal. I could see the determination in her eyes when she nodded her understanding of my terms. I turned on the remote bullet buried in Diana's pussy and went to work.
