Comforting the boss
Kit and Baloo stretched and yawned as they got up after a good night's sleep. They put their clothes on and went downstairs. Then just as they were going down the wooden stairs, the front door in the Higher-for-Hire building went up and Rebecca stepped in and had a huge smile on her face.
"Good morning you two, I have brought some bread and I will make some coffee, and then we will have a nice breakfast together." Rebecca said cheerfully and then stepped into her office where the coffeemaker was.
Baloo whispered to Kit with a smirk on his face: "Looks like someone got laid last night." Kit blushed and tried in vain not to picture Rebecca naked and getting fucked. He felt his penis slowly emerge and he had to tuck his green sweater to cover it up while they sat down and had a nice breakfast together.
Rebecca noticed how Kit looked uncomfortable and tried to avoid looking at her. Baloo noticed too and decided that he should distract Rebecca to give Kit some time to compose himself. "So, I take it from your smiling face that your date last night went well."
Rebecca beamed and said: "Oh it was such a nice evening. He was sweet and gentle and he promised me that he would call me today at work."
"That sounds great Becky." Baloo said and smiled back at her. "So are there any deliveries I have to make."
"There are some crates with umbrellas that have to be delivered to Mist Island. I expect it to take most of the day but feel free to relax at Louis' after it's done." Rebecca said cheerful.
"Wow, your date must really have shown you a good time last night. Well then I'm off, later Becky, have fun at school, Kit." Baloo said and made his way out the building.
"I better get going too. But I have arranged with a classmate that I stay with him after school so I am going to be home late." Kit said. "You just have fun Kit." Rebecca said smiling and then was left waiting in her office for her date to call.
It became late in the day when Kit returned to the Hiigher-for-Hire building. He figured Rebecca had gone home for the day and Baloo was at Louis' so he would have the building for himself.
He went inside and was surprised to see the lights were on. He thought maybe Mrs. Cunningham might be there working late, so he went to her office.
He was shocked to see her sitting at her desk where he left her many hours ago looking absolutely heartbroken. He decided to softly ask: "Mrs. Cunningham, are you alright?"
Then the floodgates opened; she put her hands to cover her face and then she began crying. Kit, naturally shocked hurried to get behind her desk to put a comforting arm around her. "Its okay, its okay, now tell me what has happened." Kit said and tried comforting his sobbing boss.
"He sob never sob called. Sob sob. He sob said sob he would sob call me back sob but he never did. Rebecca said and then began crying again.
Kit kept gently stroking her back and said: "There, there, I am sure he just forgot or got caught up with some work."
Rebecca was calming down, but was still crying. "No sob he didn't forget sob this is the third time in just two month that happened sob. Why do I even bother looking for a husband anymore sob I am too old and no man wants me."
"I want you." Kit said and was surprised you hear the words coming out of his mouth, not that he didn't mean it, because he did but because he confessed to his inner feelings. Rebecca was surprised as well, but then gave him a sad smile and a quick strong hug.
"Thank you for wanting to cheer me up Kit but I don't think you understand. What I need is an adult who will love and care for me, not a school child." Rebecca said in a sad tone.
"But I love and care for you!" Kit said defiant; the hug had emboldened him. "I know what you mean you want a mate to share the rest of your life with and I... I want to be that person."
Rebecca looked shocked at her young employee who was basically proposing to her. She composed herself and said: "Listen Kit..." but before she could continue had Kit taken hold of her head and pulled her in for a kiss.
Rebecca was shocked and managed to push Kit away. "Kit, no." She softly said before being pulled into another kiss. She fought a bit back but then closed her eyes and enjoyed the kiss,
It lasted for a moment before Kit pulled away and looked remorseful. "I am sorry Ms. Cunningham. I didn't mean to... I am sorry." He muttered.
But Rebecca wasn't angry she rather looked pleased. "It's okay, Kit. In fact we can do it again."
"Can we?" Kit said looking hopeful and smiling.
Rebecca smiled back and said: "We can, but this time when you kiss me try to open your mouth a bit and let your tongue enter my mouth."
Kit nodded and once again pressed his lips against Rebecca's. They both closed their eyes and Kit felt Rebecca slightly open her mouth and press her tongue against his. He opened his mouth a bit and let his boss's tongue enter it. It felt pleasant as it played with his own tongue and he decided to try to duplicate what she was doing.
They continued kissing and while they were kissing they let their hands gently caress each other's arms and backs. Kit then moved a hand to one of Rebecca's boobs and gently squished it. Rebecca was surprised and pulled back from the kiss.
"I'm sorry. I thought I could." Kit said looking ashamed. Rebecca smiled at him and then pulled off her purple jacket and tossed it aside. She then guided his hand back to her breast, now only covered by her white shirt and bra. They then resumed their kissing with Kit now gently rubbing Rebecca's tit and her murmuring in pleasure into his maw.
As they kissed their hands began to roam a bit more. Rebecca let her hands stroke Kit's cute face and his torso above the waistline. Kit shifted between hands he was using on his boss' breast and one he used to stroke her face and down her back.
Kit then wanted to get further so he broke the kiss and asked: "Mrs. Cunningham, can I, Can I see your breasts?"
Rebecca was a bit more hesitant this time to let the youngster see her topless. She then looked down at his lap and saw his pecker had emerged from his sheath and became a bit flustered. "Kit, I can see your thing."
"Oh sorry, it becomes like this sometimes." Kit said and covered his crotch with his hand.
"No, no, don't hide it, it's beautiful." Rebecca said as she removed his hand from his crotch and admired the cute size of his boyhood. "Does it become like this a lot?"
"Yeah it kinda does. When I wake up it's almost always hard, sometimes during the day and often when I think about you." Kit said and blushed at the last remark.
"So you think of me a lot and get hard, I'm flattered." Rebecca said and gave him a warm smile.
Emboldened Kit continued: "Yeah, I often do, sometimes I have to go to school covering my groin because I think about you."
Rebecca smiled at him, and then she took hold of the hem of her white shirt and pulled it off and tossed it aside. She let his eyes linger at her white bra and amused herself at his cute virgin expression of lust. She then reached behind her back, unclasped her bra and then tossed that aside as well.
Kit stood and marveled over her beautiful naked breasts and Rebecca amused herself over how cute he looked and how stiff his penis had gotten. She then gently took hold of his head and guided it to one of her tits. Out of a natural urge he immediately lashed on to it and began sucking and linking at her dark brown nipple.
Rebecca murmured happily since it was the first time since Molly had stopped breastfeeding that somebody had sucked her breasts and she liked it. Rebecca then sat down on her office chair and guided Kit to sit on her lap where he continued sucking on her tit. Rebecca then let her hand down to his pecker and began stroking it gently. She suppressed a giggle when she felt him hump up against her hand and she began jerking it a bit harder.
This continued for a while until Kit let go of Rebecca's breast and said "You better stop I feel like I am going to pee." But Rebecca didn't stop but said: "I don't think its pee, Kit, so let it out, let it all out."
Kit closed his eyes and did just that, but it didn't feel like pee when it came out and when he opened his eyes he saw that it definitely wasn't piss that covered Rebecca's hand but a thick white substance.
"It is called cum and when a man gets exited he shots it, and it can be used to make a woman pregnant." Rebecca said and Kit answered with an "oh" because he was embarrassed on his ignorance in sex. "Do you want to try to make me cum?" Rebecca asked and Kit's face lit up since it gave him a chance to prove he could be a good mate.
They both stood up and then Rebecca pulled down her pants along with her underwear. Kit marveled at the pretty slit but soon got a better view as Rebecca lied back on her desk and spread her legs. She then said: "Now here is what you are going to do; you are going to use your tongue down here and just follow my instructions, understood?"
Kit nodded and got his head between her legs. "Oh yes Kit. Right there. Try also licking the knot at the top. Oh you're a natural." Rebecca moaned as Kit tried his best to please his boss' pussy. He himself also licked the experience as he thought the liquids that began dripping from the hole tasted rather well.
It continued for a couple of minutes before Rebecca held Kit's head tight against her pussy and began to cry out: "OH YES KIT. Keep doing it, keep doing it. I am going to cum!" kit soon felt what she was talking about as she began bucking her waist up against his face and began spraying his muzzle with her pussy juices.
She then let go off his head and collapsed on her desk while she panted heavily. Kit was however not done yet and dove right back in to lick up more of the delicious nectar.
Rebecca soon had enough of that as she pushed Kit's away and arose to her feet. She pushed papers, pens and her table lamp away from her desk and then guided Kit to lie on his back on the desk. She looked hungrily at his semi-erect cock and Kit was a bit confused since he had never seen her look like that, but his worries were soon put to shame as Rebecca enveloped his prick with her soft lips and he felt quite blissful.
"Oh! Ah! That feels good Mrs. Cunningham. Please don't stop." Kit moaned out but Rebecca stopped anyway. Once the cock was hard and slick she let it go from her mouth since she felt it was ready for the next stage.
Kit was about to complain but Rebecca's movements made him stop and watch. Rebecca had climbed up on the table, taken hold of his cock and was lowering her hips towards it while she faced him. It made contact to her lower lips and she slowly let herself impale on the shaft. Both groaned out loudly as the penis went deeper inside her pussy until it could go no further. Rebecca then began rising and lowering her hips along the length. Kit gasped and moaned as it felt like a wet velvet glow rapped itself around his shaft.
Kit saw how her breasts jiggled each time she went down and felt the urge to once again touch them, so he did. Rebecca felt his small hands on swaying tits and leaned forward to allow him better reach while still continuing to drive herself down on his stiffness.
"Oh Mrs. Cunningham, I am going to cum again." Kit announced as he was rapidly nearing his breaking point "Hold on just a bit longer, Kit. I am almost there too." Rebecca said in between moans.
Kit managed to hold on just long enough to feel Rebecca's pussy tighten around his shaft as she climaxed. She groaned out loudly and her whole body shuddered as a powerful orgasm rippled through her body. Kit came when he felt the tunnel tighten around and began ejaculating his rich sperm deep within her.
They stayed like that for a while; him still unloading and her pussy milking his cock for more seed, until she rolled off him and lay next to him on her desk. The panted for a while longer while trying to catch their breaths and then Kit said: " Pant. WOW. That was fantastic. Pant."
Rebecca smiled at him but just realized the serious nature of what they had just done "Yeah, it was great, Kit, but we can't ever do this again."
"What? How come?" Kit said heartbroken.
Rebecca saw devastated Kit looked but continued:"Because what we did was wrong; a grown woman shouldn't have sex with a cub of your age."
Kit: "But it felt so good and it felt so right. Please, can't we do this again some other time?"
Rebecca gave him a soft smile but then said:"You are a sweet boy Kit and some day you will make some girl very happy. We can't however never do this again because as I said, that it is wrong for a person at my age to sleep with someone your age. Do you understand?"
"Okay." Kit said disappointed. Rebecca used her hand to lightly squish his shoulder as a sign of appreciation of understanding. She then stood up and put her clothes back on. She did it quickly since she now felt slightly embarrassed about being seen nude by her employee. After she had done that she sent Kit a reassuring smile that they were still on good terms and then she left.
Kit knew that Baloo probably wouldn't be home until the next morning so he had the place to himself. He did his homework and then went to his bed where he beat off twice about what had happened before falling asleep.
The next morning Kit woke as he heard Baloo coming home and slamming the door behind him. He then heard Rebecca's voice faintly from downstairs. Kit noticed that he had morning wood and thought that it would be best to rub it off rather than go to school while it slowly shrank. He began beating off but then heard Rebecca's voice. "Kit, are you awake? You have to wake up and go to school."
"Yeah I'm awake." Kit answered back through the door. He was annoyed that he couldn't give his aching cock some relief but got dressed anyway and made sure to tug his sweater down to hide his erection.
"Hi Kit, I see that Baloo didn't wake you up. He came back from Louis' just a moment ago and I have sent him out on another errand which will probably gonna take him a few hours." Rebecca said to Kit as she saw him coming down the stairs.
"Okay." He said shortly as he picked up his school back and headed towards the door. He was a little uncertain about the relationship between them now. He did what he always did and hid his erection but he might as well just let it show since she had already seen it. He however got the feeling from last night that she wanted to go back to the status quo before they had sex.
"Just a moment Kit." Rebecca said and Kit turned around to face her. "Are you feeling okay today Kit?" She said concerned but Kit didn't answer. "I would just like to apologize for what happened again and hear that you do understand that it can never happen again."
Kit gave her a comforting smile but then Rebecca noticed his unsheathed pecker. "Oh my, Kit."
Kit tried tugging his green sweater down but the damage had been done. "Isn't this what you talked about yesterday, about how uncomfortable it is to head to school with a stiff penis?" Kit nodded.
"Well, that simply won't do." Rebecca said and went down on her knees in front of him and took hold of his wood. "I can't simply allow you to be seen in public with this so I'd better help you get rid of it." Then she took the almost erect cock in her mouth and began sucking it.
"Ungh-Oh." Was the response from Kit and other moans soon followed as Rebecca blew him. The older bear wanted more of his sperm that she briefly tasted yesterday. Kit had not been the only one masturbating at the events the day before as Rebecca had put Molly to bed early so she could quickly return to her own room, where she would make herself come no fewer than six times. One of her favorite thoughts had been to suck Kit's cute pecker.
It didn't take long for Kit to climax and shoot a healthy dose of cum down Rebecca's throat. She swallowed each and every delicious drop and then stood up. "You better get going if you don't wanna be too late for school. I also want to urge you to get some pants or else I have to take care of you every day before you go to school." She winked at him and then she went back to her office.
Kit then went to school in a delightful mood and promised the universe that he would never wear pants.