A Very Personal Assistant Pt. 03 - The Conclusion

This story series has been about a company CEO, Katie who had hired Hannah as her personal assistant. Their relationship evolved into a sexual one. Katie learned that Hannah was very naive and inexperienced about sexual matters, and was raised in a strict home. Katie has been teaching Hannah different ways of enjoying sex. Recently, Katie and Hannah had gone to a couple of their friends, Alison and Kelly. There, Hannah enjoyed a foursome for the first time. She also got a glimpse into Ali and Kelly's surrender and control play. This had piqued her interest. Reading parts 1 and 2 will help the reader see how things have developed from the start.

*****

As they drove home, Katie asked Hannah what she and Kelly were discussing.

"Stuff about last night. About maybe going back again."

"And do you, do you want to go back?" Katie asked. "Try some more new things?"

"I'm not sure what that would feel like. I mean how I feel about that." Hannah turned and looked out the window because she didn't want Katie to see that she was blushing. But Katie knew what Hannah meant. There would be another visit to "Paradise Estates" and soon.

About a week passed and Hannah finally got the courage to tell Katie about her interest in the blindfold and surrender that Ali and Kelly did. On Monday, at the weekly lunch together, Hannah quietly admitted, "Katie, when Kelly and I were talking that morning, I found myself aroused by the talk of being blindfolded. I think want to talk to Kelly about another visit to their place."

Katie said, "I thought that's what was going on, but didn't want to push you into something. Now, realize that's not my thing. But, who am I to stop you from trying something new? In fact, I think I will leave that night for just you and Kelly."

"You sure? I mean I don't want you to think I'm cheating on you. You wouldn't be upset?"

Shaking her head, Katie said, "Oh no, honey. I learned that's not my thing when Kelly first blindfolded me. I thought I might be interested, but it didn't turn me on. But, I know that talk got you wet. If I thought you were cheating, I wouldn't be encouraging you to go."

Hannah's face turned bright red. "I didn't want you to know then. But I guess it was pretty obvious."

"Sure was," Katie nodded with a large grin on her face. "When we get back to the office, why don't you call Kelly and arrange another visit? Let her know it will be just you coming, and cumming and cumming."

So when they got back, Hannah called and left a message for Kelly about wanting to talk about stuff. She spent the rest of the day as horny as could be. But at the same time, wondering what she was getting herself into.

It wasn't until Hannah was home that Kelly called her. As soon as she heard Kelly's voice, that warm tingle of arousal made its way through her body.

"Hey Hannah, it's Kelly. So, you'd like to come to 'Paradise Estates' and try some new things, is that right?"

"I want to, I think."

"Okay, first, this is just playing. It's a game we play. I promise I won't cause any real pain. I don't leave any lasting marks or bruises. I will not humiliate you. You will surrender completely to me. You will do what I say. I will do to you whatever I want, within the limits we set. With me so far?"

Hannah said, "Yeah."

"Okay, we start the game when you tell me, 'I've been naughty, Miss Kelly.' Once we start, we only stop when you have had too much or when I say we're done. Now, saying no during this game doesn't mean game over. We use a safe word that means game over, which is 'red light'. If you need or want to stop, just say "red light" and I will stop immediately, game over. I will never go farther than you can handle."

"So, what all happens, I mean when we play?" Hannah asked.

"You will always address me as Miss Kelly. You already know about the blindfold. I think you realize that restraints are also involved. And you already understand there won't be real pain, maybe mild discomfort. But beyond that, you will have to wait. Part of this game for you will be the uncertainty and anticipation of what's next. But, I promise orgasms are guaranteed. If you aren't sure, we don't play. You have the stop button."

"I'm pretty sure I want to do this," Hannah said hesitantly.

"That's not a convincing answer. Think about it and decide. Then let me know using the words 'I've been naughty, Ms Kelly.' Do you understand?"

"Yes, I understand." Hannah had gotten thoroughly aroused by the discussion. She was glad Kelly was on the phone and couldn't see her.

By Friday, going to Kelly's was constantly on Hannah's mind. She wanted to call her but could not make up her mind about it. By the afternoon, Hannah was having trouble keeping her mind on her work. She was totally distracted thinking about surrendering to Kelly. Katie noticed her lack of attention to detail she was usually so good at.

Katie opened her office door and asked Hannah to come into the office. "What going on with you? It's almost like you're wasted. You're just spaced out. This is not like you." Katie was a little irritated.

Hannah blushed, "I'm sorry, I just have a lot on my mind. I will stick to work."

"This has to do with Kelly, doesn't it?

"Uh-huh," Hannah whispered.

"Have you called her?

Hannah shook her head no. "But, I want to."

Katie smiled and pointed to the phone, "Alright, call Kelly and tell her you want to play. And you might as well go home. You're not getting anything done here anyway.".

Hannah called and when Kelly answered, she simply said, "I've been naughty, Miss Kelly."

"I see, come see me tomorrow afternoon at the Estates and I will take care of that naughtiness."

Hannah disconnected and shivered with anticipation. "I don't know what I have gotten myself into."

Katie said, "From the arousal you're showing, I think you're going to enjoy yourself immensely. Now, go home, just don't make your pussy sore from the wand."

"What makes you think I'm going to go home and get off with the wand?"

"Really?" Katie chuckled and kissed Hannah and said she should call her after she gets home from Kelly's and she should plan on spending the night.

*****

When she arrived at Kelly's, Hannah had butterflies in her stomach. Her heart was beating faster than normal. Plus, she was already somewhat aroused.

Kelly answered the door and invited Hannah to sit and have a cup of coffee. While they sat, Kelly went back over the rules and the use of red light. Hannah nodded that she understood. Kelly said, "Use your words. Say it."

Hannah took a deep breath and said, "I understand the rules and how to use red light. I want to play the game. Miss Kelly, I have been naughty."

"Well then, little Missy, I have to do something about that." Kelly got up and took Hannah by the hand and they went upstairs.

Hannah walked into the master bedroom and she could see the wrist and ankle cuffs, the blindfold on the bed, and a small table with things on it that were covered. She wondered what she had gotten herself into. But on the other hand, she could not deny the wetness forming in her panties.

Kelly sat on the blanket chest at the end of the bed. "I want you to take off your clothes except for your bra and panties for now. Can you strip in a sexy way?"

"I will try, Miss Kelly." Hannah started trying to mimic what she had seen in porn movies but didn't know what Kelly wanted. She undressed slowly and soon Hannah stood before Kelly in a sports bra and cotton panties. Even though she wanted to cross her arms, she left them at her side.

"Okay, we will have to teach you about getting undressed in a sexy manner. But it's alright because you tried." Kelly pointed to the floor directly in front of her and motioned Hannah to stand there. "Now, tell me Missy, how were you naughty?"

Katie told Hannah how to answer the question, so Hannah said, "I called Katie a bitch."

Kelly responded with mock indignation. "Well come here, you need a spanking," Kelly instructed Hannah to lie across her lap. "Since this is your first offense, you will get just ten spankings. Count them as you receive them.

Hannah felt Kelly's hand smack against her ass. "One." She thought it wasn't too bad.

Kelly reached back and slapped the other cheek, just a little harder.

"Ow...two.

"SLAP, SLAP, SLAP SLAP." The spanks came in rapid succession with increased intensity. Hannah's ass was stinging and she had trouble focusing on counting them. She was distracted by the arousal the spanking was causing.

Kelly peeled her panties down and started rubbing her ass cheeks. "You have a nice pretty ass, especially since it's nice and pink for me. Like your pussy." Suddenly Kelly's hand came down quickly and firmly in quick succession for Hannah to feel some real discomfort. "You stopped counting. Do I need to start over?"

Her ass stung but she wasn't sure she wanted her to stop. "No Miss Kelly."

"We're up to six." With that Kelly administered four more spanks, two on each cheek.

Hannah dutifully called out, "Seven, eight, nine, ten."

Kelly gently rubbed the now bright red ass on her lap. "Now that wasn't too bad, was it Missy?"

As Hannah stood up, she answered. "No, Miss Kelly."

"Now take off your bra and step out of those panties and give them to me." Kelly took the bra and tossed it aside but took the panties and took a deep breath inhaling the scent of Hannah's arousal. "Lie down on the bed in the middle, use the pillows to prop your head."

Hannah got as comfortable as she could, not knowing exactly what awaited her.

Kelly came over and said "First thing is the blindfold. You won't be able to see what's happening." With that Kelly slipped the mask over her eyes.

Hannah expected it would be like closing your eyes, but then you can cheat a little. This was a completely different feeling. She couldn't see anything. The anticipation seemed to make every part of her body tingle.

Kelly just stood there silently to allow Hannah's tension and anxiety to rise. But before it got too much, she leaned over and flicked her nipples several times.

Hannah jumped and her whole body flinched in response.

"We can't have you jumping around like that. I guess I will have to restrain you. Spread your arms and legs out." Kelly went around and attached the cuffs to her wrists and ankles as well as to the restraint system under the bed. She adjusted it so Hannah was still able to move some, but just a little.

Being completely helpless was a different feeling. Hannah relaxed some as she got accustomed to these new feelings. Just at that point, Kelly flicked her right nipple, then the left. Then it was a steady back-and-forth rhythm. Hannah's nipples got harder and harder and she started moaning in pleasure.

Then Kelly stopped, picked up a long feather, and brushed it against Hannah's face. "Are you ticklish, Missy?"

Nervously Hannah answered, "Uh...a little."

"Let's find out." With that Kelly began to stroke Hannah's neck lightly. Then she rubbed circles around her breasts. Hannah started laughing and squirming. Kelly moved to her underarms.

Screeching Hannah cried. "Oh god no....!" Her laughter filled the room. She tried moving away from the feather but was held in place by the restraints.

Kelly tickled her way down across her belly. Then teasingly skipped over her pussy. She touched her inner thighs, observing Hannah's wetness dripping onto the sheets. She continued downward until she got to her feet. "Are your feet ticklish?"

"No, please, not the feet!" Hannah begged.

"Okay, since you asked nicely...NOT."Kelly began tickling the soles of Hannah's feet. Hannah started squealing and thrashing about. When Kelly saw Hannah was laughing so hard that she had trouble catching her breath, she stopped.

Hannah lay there, beads of sweat covering her forehead. Her face was red from laughing so hard and it seemed she was even more aroused than before.

Kelly put the feather down. She intended to bring Hannah to the brink of orgasm several times, before having Hannah bring her to orgasm with her tongue. So she laid next to her and asked Hannah if she wanted to cum.

Hannah begged, "Oh yes, please, I am so horny. Please, Miss Kelly."

Without a word, Kelly took her fingernails and traced them down Hannah's body. When she reached her pussy she said, "Oh my look how wet Missy has become." She traced her finger without touching Hannah's clit, down between her slit. She started back up again and asked "Do you want to cum? Have you learned to not call Katie a bitch?" She had no intention of letting Hannah cum yet.

"Yes, Miss Kelly."

But when Kelly simply touched Hannah's clit, her body could endure no more and a climax hit like a firebomb. The bomb was deep in Hannah's body, the trigger was Kelly just touching her sensitive clit. It ignited her pussy and blasted its way throughout her body. When the blast reached her brain it set off an explosion of pleasure. "Holy Shit! Oh my god!" she cried as the pleasure flew back to her pussy and set off another explosion of delight. Her whole body shuddered and shook. The orgasm seemed to last forever, even though Kelly had removed her finger at the start of the climax.

While Kelly did not intend to let Hannah cum, she smiled knowing how aroused Hannah must have been to cum that fast. But she also saw an opportunity to let Hannah have another experience. While Hannah recovered from her orgasm, Kelly took out the flogger.

"Hannah, you broke one of the rules. Miss Kelly always cums first." Kelly tried to sound stern but wasn't too successful. "You need additional punishment."

"Another spanking?"

"No, something else." With that Kelly dragged the strips of the flogger across Hannah's face. Unsure if Hannah knew what it was, Kelly said, "This is called a flogger. It has 9 strips of leather on it. I am going to use it to punish Missy here for cumming first."

Hannah stiffened, "Uhm...I...I'm not too sure about this." In her mind, she contemplated saying red light. She knew how much pain a flogger could inflict.

Kelly said, "Remember the rules. I said no real pain, no bruises or lasting marks. Also, don't forget you know how to end the game."

Trusting Kelly, Hannah said, "Okay, let's keep going." Hannah tried to relax.

At first, Kelly simply dragged the strips across Hannah's belly. "See, not too bad...yet."

Hannah heard what Kelly said but started to wonder.

Kelly gently swung the flogger so it slapped across Hannah's belly.

Hannah grunted a little. She thought that this wasn't too bad.

After a couple of very gentle slaps, Kelly gave her a harder slap, one you could hear in the room.

Hannah whelped, "Ow!" She received several more slaps, each one causing a stinging pain. Suddenly, Hannah discovered with the pain came a strange sense of pleasure. She hoped Kelly would keep going.

Kelly watched Hannah's face turn from agony and pain to one of pain and pleasure. Some minor red marks were appearing on her skin. After a few more slaps on the belly, she moved to slap Hannah's thighs.

Hannah flinched as each stroke hit its mark. There was both pain and pleasure. It was unlike anything Hannah had ever felt before.

Kelly realized Hannah was becoming uncomfortable so she stopped and said, "Take a couple of deep breaths, you are doing fine. Focus on your pussy. You seem to becoming very aroused again."

After pausing for a couple of moments, Kelly swung the straps back and forth, so that each time it came forward, it brushed against Hannah's pussy. She didn't slap, just swung the flogger back and forth. Kelly knew that as aroused as Hannah was, this would be almost excruciatingly pleasurable. "Don't cum until I tell you." The flogger continued swinging and grazing Hannah's pussy.

For Hannah, it seemed like every nerve was buzzing. Her pussy was throbbing, her clit erect, her nipples were sticking out like knobs. Her forehead was covered in sweat. With every stroke, the flush on her face slowly made its way down until her whole chest was red. She was on the absolute brink of orgasm. At that point, Kelly stopped. Hannah sighed in disappointment. She was this close to cumming.

"That's enough Missy. Now, I will give you the honor of pleasing me."

Kelly removed the cuffs from Hannah's wrists and ankles. "Close your eyes." as she removed the blindfold.

Hannah closed her eyes as Kelly removed the blindfold. She blinked several times as her eyes adjusted to the light again. "Thank you, Miss Kelly."

As Kelly climbed on Hannah's face, she said, "I am sure you know what to do here. Pleasure me and you will be rewarded."

Hannah eagerly started lapping at Kelly's pussy. She gave each of her lips some attention, by licking and then sucking on them one at a time.

Kelly, who was already very aroused from taking charge of Hannah, was shaking and grinding against Hannah's face. With each lick and suck, Kelly's moans grew louder and more intense.

Hannah responded to Kelly's moans by sliding her tongue between her lips and began tongue fucking her. In and out with her tongue, until she couldn't thrust any deeper or faster. When Hannah could feel Kelly on the brink of climax, she wrapped her mouth around her clit, and reached up and pinched Kelly's nipples.

As Hannah ate her out, the pressure inside Kelly grew and grew. When Hannah pinched her nipples, Kelly's orgasm hit like a summer storm. Lightning flashed in her eyes, thunder rolled throughout her body. A whirlwind brought her to the peak of pleasure which then rained down like a flood. It was so intense that she fell onto the bed. Kelly twitched and moaned for some time before calming down.

"God damn. That was one hell of an orgasm. Did Katie teach you to eat pussy like that?" Kelly said as she was panting, trying to catch her breath.

"Kinda. I just know what feels good for me and tried to make you cum."

"Well little Missy, it's time for your reward. I want you to prop yourself up with these pillows and simply enjoy." With that, Kelly began to lick at Hannah's throbbing pussy. She wanted to build it up but she knew Hannah was already on the brink. She gently pushed one finger inside her hot tight pussy.

Hannah simply sighed as Kelly started tenderly caring for her pussy.

After inserting one finger, she slid a second one inside and began a leisurely fucking motion. "Hannah, you are so hot. I just love your tight pussy. Squeeze down for me."

Hannah clenched and let go a couple of times. Each time, the sensations brought her nearer to climax. She started that animal-like growl she did when close to cumming.

"Tell me how bad you want to cum."

"I want to come so bad. I need to cum." There was a desperation in Hannah's voice.

"Remember, you can't cum until I say so." Kelly stopped finger fucking Hannah.

"Please Miss Kelly, please let me cum!"

Kelly started shoving her two fingers back into Hannah's throbbing hole. She took her clit into her mouth and gently bit it. "Cum for me, Hannah. Cum for Miss Kelly." As she felt Hannah's climax begin, she reached up and squeezed her nipple hard. And the climax hit.

Hannah's orgasm hit like a dam breaking. The intense flood of sensations quickly overflowed her brain. It boiled as it struck her hot pussy. Her entire body swayed as wave after wave continued back and forth. Finally, the flood receded and she could think again.

But Kelly wasn't finished. After giving Hannah a moment of reprieve, she started again. Fingers thrusting deep, nibbling on her clit, grabbing Hannah's whole breast and squeezing. "I know there's another one hiding in there. Give it to me, cum again for Miss Kelly"

Hannah felt the crash of another flood of pleasure course through her body. She trembled and convulsed. She grabbed at the sheets. This orgasm put the last one to shame as pleasure blinded her. Her clit began to be so sensitive, it began to ache. "Please stop, no more. I can't take any more." Then she remembered the rules and cried out, "Red Light!"