The day she left, Jan told me that she had just run into Jenny at the grocery store, home on a break from school. She said, “I’m sure Jenny could probably watch the kids the night you need a sitter.”
I never had told Jan about the spanking I had given to Jenny, the last time she sat for us. I felt a little guilty about just how often I thought about that event, and I was quite apprehensive about calling Jenny. Though she had seemed to appreciate the spanking at the time, several months had passed, she was now a college freshman and I imagined she might have some regrets about that night, and may not even want to hear my voice.
I tried to think of other options, but soon realized we did not know anyone we could trust a much as we do Jenny. Jan, of course, had no knowledge of the “help” I had given Jenny, so since she suggested I use her, I pretty much needed to make that phone call.
I made myself dial Jenny’s cell number. After several rings, it went to voice mail. Either she could not get to her phone in time, or she saw it was me and did not want to answer. I left a message, “Jenny, this is Mr. Mann, I hope you are doing well. I am in need of a babysitter tomorrow night and I understand you are home on a break. Please call me if you are available.” I tried to sound as friendly and upbeat as possible, but worried that my nervousness may have come through in my voice.
For the next hour I wondered if I would ever hear back from Jenny at all. If I did, what would she say to me? Does she think I’m an awful old man, or what?
My phone rang, I looked anxiously at the number to see that it was indeed Jenny. My hand shook so hard I was fortunate just to hit the accept button. I took a deep breath to calm myself and said, “Hello Jenny.”
“Mr. Mann, I was so happy to see that you called, sorry it took me so long to get back to you, I’ve just come out of a movie. Do you still need a babysitter tomorrow?”
“Yes, I sure do Jenny. I would need you to pick the kids up at day care by 5 PM, feed them and get them down for the night. I should be home by 11.”
“That sounds great to me, Mr. Mann, I’ll take good care of the kids and look forward to seeing you, whenever you get home.”
What a relief, I hung up and took a deep breath. The call was uncomfortable for me to make, but Jenny sounded like she was truly happy to hear from me.
The next day went along as expected. I had a good dinner meeting with our client, which ended early enough for me to get home by 10:30. Driving home, I again felt some nerves wondering how awkward my seeing Jenny might be. I just tried to remind myself of how friendly she sounded on the phone, but still, this would be just the two of us for the first time since I had given her a spanking.
Jenny was cleaning the kitchen, when I walked in. She was wearing nice form fitting jeans and a white blouse with some decorative lace. The blouse was open just enough to show a bit of cleavage, as she leaned over to wipe the counter off. She looked even prettier than I had remembered and she seemed happy to see me.
“Hi Mr. Mann, you got home early, that’s great.” She said with a friendly smile, “How did your meeting go?”
“The meeting went very well, Jenny, thanks for asking. How were the kids tonight?”
“Oh Mr. Mann, you have the best kids. After dinner we played a couple of games and when it was time for bed, I read them one story and they were out. I really have to thank you for letting my watch them again.”
“Jenny, I can’t tell you how happy they were to find out you were coming. I’m glad you still wanted to watch them for me.”
“Mr. Mann, of course I always love to watch your kids, did you think I wouldn’t?”
“Well Jenny, I was a little concerned that you might not want to come over here again, after the last time.”
“Mr. Mann, are you thinking I would not watch your kids again, just because you had to spank me that last time?”
“I guess I wasn’t so sure that spanking you like I did, was really the right thing to do Jenny. I thought you might be a little upset or embarrassed about it, after all of this time.”
“No sir, Mr. Mann. If you only knew how much good that spanking has done for me. Every time I start to lose my concentration or focus at school, I just remember the things you told me while you were spanking me. It really is helping me to keep focused better than I ever was before. You gave me a really good spanking which I needed, when I needed it. I’ll never forget that.”
“Wow Jenny, it means a lot to hear that from you, really a big relief. I guess I was feeling a little guilty not just about spanking you on your bare bottom, but that I can’t seem to stop thinking about it. I really enjoyed lifting up your skirt, pulling your panties down, then feeling and spanking you on your lovely 18 year old bottom. Plus, I had a pretty good view of your pussy, when you spread your legs open for me.”
“Mr. Mann, now you are making me blush a little. I want you to know that while I really do adore your wonderful children, I have always had a pretty big crush on you. I think you’re a very handsome man. You are friendly, intelligent and have always treated me with kindness and respect. Yes, even when you were spanking me, you made me feel like I was really important to you.”
I looked at Jenny, both surprised and amazed at what she had just told me. I also realized that at some point between finishing up in the kitchen and sitting in the family room talking to me, one additional button of her blouse had worked its way open. I had no idea if she was aware of this or not, but I now had a pretty good view of more than a little cleavage as well as a good bit of her lacy white bra. I tried to keep from being obvious, but I guess she noticed where my eyes were being drawn. She looked down and seemed surprised at the open button.
She said, “Mr. Mann, I’m so sorry, I guess my button must have just come undone. Is that what you were looking at?”
“Jenny, you are such a beautiful girl, I can’t lie to you, I was looking a little to much where I should not have been.”
“Oh that’s OK Mr. Mann. I really do like you, so I’m flattered that you are starring at my blouse.”
While starring back at me, Jenny slowly moved her fingers down to the next button and kind of played with it, as she spoke. She then lowered her eyes to watch as her fingers opened that button. She raised her eyes for just a second to look at me, then lowered them again as she opened the final button on her blouse. She looked up at me kind of shyly, (With the buttons open but the blouse held closed by her hand) and asked in a soft voice, “Mr. Mann, Do you like watching me open my blouse for you?”
“I do Jenny, yes I really do.”
“Good” she replied, as she let the blouse fall open and pulled the remaining material from her jeans, providing me a perfect view of her lovely thin white lacy bra.
“Mr. Mann, do you like my bra?” She asked.
“It is a beautiful bra you are wearing Jenny, and you fill it out very nicely.”
“Thank you Mr.
“You look amazing Jenny, you truly do.”
“Is there enough light for you to see my nipples through the lace, Mr. Mann?”
“Yes Jenny, your nipples are kind of hard now, so they are poking through the lace very nicely.”
“I will take off my blouse now, Mr. Mann, so you will have a better view.” She said as she gently pushed the material off of her shoulders, allowing the blouse to fall to the floor.
“Is that better, Mr. Mann?”
“That is better Jenny, so very much better.”
She looked down, cupped both of her hands under the lower part of her bra and gently squeezed and bounced her breasts up and down a few times, smiled at me and winked.
“Would you like to help me take this bra off now, Mr. Mann?”
“Yes I would very much like to help you remove your bra Jenny. I really do want to see your tits.”
Jenny sat next to me on the love seat smiled and gave me a nice kiss. During that time, though my fingers were shaking with excitement, I was able to unhook the back of her bra. She pulled back from me just a few inches to let me slide the bra straps off of her shoulders. She then allowed her bra to fall away from her magnificent, naturally full round tits. Her nipples protruded 1/2 an inch as I sucked and fondled them for several minutes. During that time, I noticed that Jenny’s right hand was now on my lap, gently brushing against my cock through the material of my dress pants. As I let loose of her breasts, she looked down at my pants, grabbed my belt and worked it open.
She then said, “Mr. Mann, when you were spanking me, I did feel your spanks, but I was even more aware of what I felt growing underneath me pussy. The more you spanked me, the more I knew you had a really big man sized cock. One that I needed to see, feel and suck. So now, I have to pull your pants down because I need to look at your big dick.”
With that, Jenny unhooked the top of my pants, pulled the zipper down and pushed my pants to my knees. She then put the fingers of her right hand inside the front elastic of my underwear lifting the waist band up and over, exposing my throbbing cock. She immediately placed her right hand around my member and expertly rubbed it.
She looked up at me with a giant grin and said, “Mr. Mann, you have a huge cock, I need to suck it now.”
Jenny then slid down onto the floor to give me the blow job I could only have dreamt about. This beautiful 18 year old cheerleader, had my cock in her mouth as I watched her head going slowly up and down over and over and over again. It was all I could do to keep from coming in the first few seconds.
After sucking me for several minutes, Jenny held my cock tightly in her right hand, looked up at me with her big brown eyes and said, “Mr. Mann, I want you to cum on my face.”
That was all it took, as she gave my dick a few more tugs pointing it directly at her open mouth just a few inches away. I let loose with a barrage that amazed even myself. Most of the initial blast found Jenny’s mouth, the next few ended up mostly on her nose and cheeks. Jenny then sucked and liked all she could from the head of my cock. She then wiped all she could find off of her face and licked her fingers clean.
She looked up with the brightest smile I have ever seen and said, “Umm you taste so good, Mr. Mann.”
“Jenny, that was the most amazing blow job I have ever had.”
She surprised me again by saying, “Mr. Mann, I’ve been a very naughty little girl tonight, haven’t I?”
“You have been a very bad girl, Jenny. I’m glad you know that.”
“Do you need to punish me before I return to school tomorrow, Mr. Mann?”
“I think you understand that I will need to give you another spanking, don’t you Jenny.”
Little Jenny was now standing next to me. Her firm naked young breasts with still hard nipples were right at eye level. With my right hand I reached around her to pat and grab the back side of her jeans. I said, “Jenny, you will need to take your jeans off now.”
While I continued to fondle her jeans covered bottom, Jenny looked down and slowly opened her belt buckle, unsnapped her jeans and pulled down the zipper. She began to push her jeans down and I could see that her lacy white panties matched her bra which was laying on the floor nearby. As she stepped out of her jeans, I told her I thought it was nice that her bra and panties were such a pretty matched set.
She said, “I’m so happy you noticed Mr. Mann, they are really comfortable as well. It looks like my panties have gotten a little bit wet, doesn’t it, Mr. Mann?”
“Let me check that out Jenny,” I looked closely and felt the front of her moist panties with my fingers. “Your panties are pretty wet Jenny, but that just makes it easier to see the outline of your neatly shaved bush as well as your cunt, through them.”
“Are you going to pull down my panties, Mr. Mann, or do you want me to do that for you?”
“I would like to watch you take your panties off, if that is alright Jenny.”
Jenny immediately obeyed, pushing the wet lacy panties down her legs, until they fell to the floor and she could step out of them.
As I studied her pussy, Jenny said, “I’ve been a very bad little girl, Mr. Mann. I need you to give me a really hard spanking tonight.”
With that, she bent over and laid across my lap. I helped to get her totally naked body into the proper position. I rubbed her pretty little ass very lightly as she spread her legs open as far as possible. She turned her head back and said, “Mr. Mann, I want you to have a good full view of my pussy during the entire spanking.”
I began to give Jenny a steady stream of crisp hard spanks on both cheeks. Her legs began to kick with a good amount of energy almost right away. I built up the speed and firmness slowly and as she continued the kicking, she began loudly yelling, “Harder, harder spank my ass harder Mr. Mann, I need you to spank me harder!” As the spanking got pretty much as hard as I could do it, I noticed Jenny had slipped her hand underneath her pussy and she had inserted two fingers well up into her cunt. She was working them feverishly as I tried to continue the spanking. Finally I noticed a third finger had worked its way into her clit. She was thrashing about so out of control that all I could do was try to keep her from falling off my lap. I ceased the spanking and just held her the best I could.
I heard her yell, “I’m coming Mr. Mann, I’m really coming.”
I just held her in position and watched as she worked her hand and fingers well up inside of her cunt. She finally erupted with loud moans and gowns that seemed to go on forever. Finally, Jenny came to rest, still panting at first. She was eventually totally spent and just laid still across my lap for several minutes, while I gently rubbed her well tanned bottom and told her how amazing it had been to watch her come like that.
Finally recovered, Jenny got up off of my lap, picked up her cloths and took them into the bathroom. Fifteen minutes later she emerged, looking as sweet and innocent as anyone ever did. She said, “I really enjoyed baby sitting your kids tonight Mr. Mann. I have to go back to school tomorrow, but I’ll be back home for spring break. If you need a babysitter, please call me.