I Was Their Babysitter Pt 01

Disclaimer: This is a work of fiction, and it was created solely by me as the author. All characters are over the age of 18. Any similarities to characters, real life people, or things are all happenstance, though my appreciation to those who have

inspired

my works is immense. YSI, my treasured friend.

Author's Note:

This is the first part of a series I've created about some experiences I envisioned once upon a lifetime. As it is a first for me in

this

category, I hope you'll find yourself wanting to check out the rest of my works while you wait to see what else I've got to share! Please *follow me* so you'll be the first to know when the next parts come out. I know you'll want to see what happens!

Questions and comments are welcome. Please take the time to rate this story also. I hope everyone will be kind.

I Was Their Babysitter - pt. 1

"So, how's college going?" Connie Dartmouth asked me as we walked around the mall. I'd known her since I was nine years old, had just moved into the neighborhood, and had been watched after school by her. Then, when I was eleven, almost as if in a week's time, I became her kids' babysitter.

"It's different, that's for sure," I answered. "I sure appreciate your offer to take me out for some shopping. It's nice to hang out with you a little more than the usual couple of minutes before and after I babysit for you."

"Well, the kids don't need a babysitter all that often anymore, but we sure enjoy your company. You're part of the family, you know?"

"I love your kids as if they were my own," I answered honestly. I always thought about what-if situations, and if something happened, God forbid, to Mark and Connie Dartmouth, I'd fight like hell to remain in their lives and be their guardian if at all possible. I was young, sure, but determined as hell.

"That's why you still get called now and then to stay with Chrissy," Connie reminded me. Janet, Jack, and Chrissy were the three kids I'd been babysitting for eight years now. They were some of my favorite people on the whole planet. Oh, their names? Weird, right? Especially for this era. Well, their parents were obsessed with Three's Company, and to pay homage, to pick names no one else would use (anymore), and because each name was in the family tree somewhere, those are what they went with.

"Well, hey," I stated as I stopped near the stairs. "Would you like to stop for lunch? My treat, too," I offered. "You really didn't have to pay for my outfit earlier, and it's nice to spend some time with you. With my job at Diamond's, I can pay for things like that. It was from babysitting for you guys so often that I was able to buy my first car!"

"OK, just this once," Connie gave in. "But you really don't have to do that. I suppose here in the little food court, it won't put you out

too

much. But I still have another couple of shops that I want to take you to, and those will be on me. When you finished high school, we sent a gift over, but I really wanted to get you a few more things. That's part of this shopping trip's purpose."

"Well, I can't wait to hear what else you've got in mind," I shared and took her arm to make our way down to the lower level.

As we sat and ate our food, Connie gave me her perspective about how I had come into their lives as a young lady and grew into a beautiful woman. It was so nice to hear, but taking compliments wasn't always my strong suit. She touched my hand a few times and assured me that it was true.

"I remember the first time we had you babysit," she reminisced. "You were a little nervous, but we knew you'd do great, not to mention the fact that your parents were two streets over. When we came home, you were asleep on the couch. I think that's the only time we ever found you that way."

"Yeah," I admitted and covered my face. "I remember waking up and feeling like I had failed because I hadn't stayed awake!"

"Oh, nonsense," Connie argued and laughed. "Mark took you home, and you just kept coming back."

"Well, I had a pretty good gig with you guys," I responded with a shrug. "You tended to stay out pretty late, so I got to put the kids down at nine, and I had the house to myself for a good five hours, usually."

"Mmm-hmm," Connie replied with a smile. "And, while we've never talked openly about it, we don't exactly have the

usual

things to do or look at or watch at our house." I began to blush and look down at my food. I mean, I knew what she was talking about, and she'd only mentioned it once as a laughing point when getting ready to leave years earlier, but otherwise, I was well aware as to what she was addressing. "And you've explored the many options, yes?"

"I always snuck a peak in the bathroom," I confessed. "I mean, I was basically sheltered when growing up. I couldn't even talk to my mom about some things, but I was curious, and they were right there, so..."

"You can admit it," Connie encouraged. "We're friends, Steph. If you're comfortable talking about it, I'd like to continue asking you about it."

"Well, as long as you're OK with me blushing," I answered and shook my head. "For as much as I know, I guess you could say, I'm still a bit, um... inexperienced."

"Oh, that's OK," Connie assured me. "So, did you watch the channel?" I nodded remembering all the times I'd scoped out the naughty channel after the kids were asleep. "Ever watch any movies?"

"On the channel?"

"No, in our collection?" Connie corrected and patted my hand.

"Oh, yes," I confessed and smiled. "I remember wondering as I explored all those sexual positions, encounters, and different pairings if they really happened in real life."

"Not all of it," Connie answered nonchalantly, "but yes, most of it. A lot of that stuff is for the movie to make it hotter, stand out... you know, unique. Anything in particular?"

"Well, there was one where they were outdoors," I explained. "I was surprised that people could just do it like that on a tree, or..." I continued and gasped. "This one? The girl was on roller skates, and the guy picked her up, turned her upside down, and..."

"Oh, yeah," Connie acknowledged and laughed. "Again, probably more for show," she clarified. "But, um, did you enjoy those?"

"Yes, but I never watched them until I knew the kids were asleep," I promised. "You're not mad, are you? You seem more interested than upset."

"Oh, I'm definitely interested," Connie assured me. "I'm certainly not upset. They were right there in the living room," she added. "I knew there was a chance you'd get curious. I told Mark we should probably have put them away, but by the time we noticed that one was not where we'd left it the last time we'd checked the cabinet..."

"Busted," I murmured and covered my face again. "I got really curious and pulled a bunch out so that I didn't have to keep going back and forth. I probably rearranged them. That was a rookie move, huh?"

"Actually, I'm glad you were watching them, especially now," Connie offered. "Hearing that you didn't have anyone to talk to about it makes me sad. I wish... well, nothing we can do about it now. But, well, from now on, Steph, please know that I'm incredibly happy to talk to you about anything."

"Thanks. I really appreciate that. In fact, I feel really comfortable talking to you about it."

"That's what I was hoping for," Connie shared with a nod. "Well, let's keep talking about this and head up to the next store. I definitely have some things to buy you there."

"Oh," I breathed when Connie led me to the fancy lingerie store. "I, um..."

"Let's sit here on the bench for a second," she suggested and pointed to a little spot nearby. "I want to explain." Once seated, Connie continued. "You know we love you, Stephanie, and we want you to feel comfortable around us. Here's the deal. I am going to share something with you, and I need you to understand that we won't be offended or hurt if you say that you aren't interested. I did take you out today for this reason, but I want to continue doing this with you no matter what. You're a dear, family friend, and I don't want this to change that."

"I'm listening," I promised. "And I can't imagine anything changing that, Connie. I love everyone in your family so much. We even exchange Christmas gifts! I have three of them on my list for today!"

"That's wonderful, sweetie," Connie responded and seemed a little relieved. "Mark and I love you very much, too. In fact, we'd like to include you in on a little something. The kids and I will be heading to my parent's place in Michigan for the holidays. Mark has to stay home for work."

"Has he ever missed the holidays before?" I asked as I sipped my drink.

"No, but we were up there for Thanksgiving. His work gave him the time off to take that trip so that he would be available to work over the Christmas season. He's not thrilled, per se, but we came up with an idea that might work out. Would you like to hear it?"

"Absolutely," I answered. "I just don't get what that has to do with me. He'll be home to take care of the dogs and the mail, so what could I do to help?"

"Mark and I would like for you to keep him company some of the time that the kids and I are away," she answered slowly. "I don't want to tell you to

lie

to your parents, but..."

"Oh, forget them," I answered and waved away her concerns. "They don't pay attention to what is going on. If I say I have to babysit, they are glad to see I'm making money. They don't keep track of what other families are doing these days. Mom is all about the dinner and taking care of the boys and Grandma. I won't have to lie. I'll just say I'm working for the Dartmouths, if that's what I'm doing. I'm still not sure what's happening."

"Well, you've stayed overnight before," Connie reminded me. "It'd be like one of those scenarios, presumably. Again, that's if you'll want to do this." I nodded agreeably for now. I still wasn't sure what she needed me to do. "I didn't know for sure, but since you confirmed that you're a virgin, we were wondering if you'd like to have your first time with someone who knows what they're doing and would give you a memorable experience."

"But, like... who? Does Mark know someone who wants to have sex with me?" I whispered as I moved in closer to her.

"Actually, Mark would like to do that, if you'd like that," Connie explained and watched my face as the realization surfaced. While my eyes grew, I searched her face for the seriousness or joke of the matter.

What?

Mark would have sex with me? Did I want that? Did I... was I dreaming? I'd fantasized about him a lot, but did I ever think it was possible?

"Mark wants to be my first?" I asked and leaned in more. "Mark wants to have sex with me? But, wait. No!" I whispered harshly. "I wouldn't do that to you. Why would you..."

With a hand on my knee, Connie scooted even closer. "Steph, no!" she stated reassuringly. "Honey, I

want

this for you, for the both of you, really, I do. It will make me so happy to know you're being shown how to be with a man in a proper and safe way. I promise, it will be done responsibly which is something you can't count on with boys your age." She paused. "What do you think?"

"What about, um... protection?"

"Are you on birth control?" Connie asked and slipped her hand gently up a little farther above my knee. It wasn't inappropriate, but there was intimacy in her touch. I'd never felt anything like it. I could tell she cared, and I knew I was safe. This was all just so... unexpected. Oddly though, it excited me.

"Yes, I have seen a gynecologist since I turned sixteen," I confirmed. "Mom didn't want me to suddenly come home pregnant and burden her with a problem. I was having some period issues, so it actually calmed them down, not that Mom cared about that. She just wanted all bases covered."

"Good," Connie answered and then turned suddenly. "Oh, not about the fact that your mom was so crass about it, but that you're protected. I should have asked sooner. I know your mom on a friendly level, I suppose, but we have never been close enough to talk about such things. I'm sure you see her quite differently than I ever would."

"I appreciate that," I replied sincerely. "I have always loved that you called on me to babysit regularly. It was always nice to escape my house to be around people who liked me a little more than tolerated me."

"Well, here's what I'm thinking," Connie stated with finality before getting ready to stand up. "Let's go in this little shop. I'm going to suggest a few things for you. I want you to tell me what you think looks nice, too, and I want you to ask questions. Let me know if you wonder about certain items. I'm happy to answer any questions. And I'll be paying in here. Don't you worry about how much something is or how much the total bill will be. In fact, you'll come sit back out here when I get ready to check out. I want to do this, and you can't stop me from splurging on you. Let's have a little fun."

I looked at my older friend and pondered how bad it would really be to have this experience. Was it a little strange to have this experience? Well, yes. I had to presume that not many people were asked if the man they've babysat for could take their virginity. I had to also suspect that the wife of that man didn't usually not only condone it but want to dress up that person with gifts of lingerie as well. Well, none that I knew, anyway. Would it hurt to have this experience? You know what? I was going to go ahead and see what happened in the store. I was quite possibly on board for this.

"You know what?" I answered and nodded. "Let's do this."

"Really? No argument?"

"Nope," I answered and took her arm. "I've decided to trust you which is what I should have done when we first sat down."

"Well, it's not a usual request or suggestion," Connie confirmed. "But I love this attitude! Let's go have some fun."

I saw lacy, silky, thong, tiny, bigger, colorful, and crotchless styles of panties, front-clasping, wired, push-up styles of bras, and some garters, gowns, and cute little cozy (and kinda sexy) pajama sets. Nothing was off the table, and the more I expressed interest in the items, the more excited Connie got about our shopping experience.

"I am certain that Mark will love to see you in these," Connie declared and held up a pair of panties. "Now, I have to ask," she continued and reached for my hand, "do you shave?"

"Actually, after all the 'research' I've done from all that I saw when watching the movies at your house, I found that waxing was my preference. I love the 'clean and smooth' presentation. Plus, it makes it that much easier to wear a swimsuit. Having a pool means I'm in one often, so no cleanup around that area just made life simpler."

"Wow," Connie reacted with a slight nod. "Did you ask your friend to take you, or... Well, I mean, I know you wouldn't have asked your mom," she added decidedly.

"Actually, I had a cousin who goes, so I just asked a few questions, looked up a few common questions, and made an appointment. The girls were all surprised that I didn't jump or act nervous. I guess I have a high pain tolerance, but I love to go and get it done. I'm on an every six weeks plan. I especially enjoy the first few days afterwards. I feel... tingly. Does that make sense?"

With a hearty laugh, Connie squeezed my hand. "Does it make sense? Oh, Steph, you don't know how much sense you're making! Hell," she added quietly, "I'm feeling rather tingly myself, just thinking about it." We giggled together and let go of one another as she dropped the pair of panties into her basket. It was rather full, her collection of items. There were so many that I wasn't sure what had been selected for me or for her.

"Now," Connie announced, "scoot on out to our little bench out there. I'll be out in a few minutes. In fact, why don't you get us some yummy dessert drinks? I might pick out a few more surprises. I'll meet you out there shortly."

"OK," I answered knowing any arguing would be met with a disappointed look. I hated to disappoint her, so I did as I was told.

"Alright!" Connie sang as she walked out with two large and rather heavy-looking bags. "Let's head out," she suggested after having handed me one bag so she could drink her treat with the free one.

On the drive home, Connie explained how she envisioned things happening. She explained that there were some rules, but she had a good feeling that I would have no issue with them.

"Mark is my husband, and that won't change," she affirmed. "I am fine with and actually excited about you having sex with him. Because I'm fine with it, the idea of an 'affair' doesn't even get entertained. Does that make sense?"

"Surprisingly, yes," I replied. "Weird, because if I hadn't been informed in the way you presented it at the mall, I probably would have worried about that. I don't want to take him away from you. In fact, that's not even an idea to entertain from my standpoint. He's your husband and the kids' father, and I know this experience will be quietly handled. No one will know, but you're good with it, I'll no longer be a virgin, and Mark will be happy to have helped me to accomplish that. Yes?"

"Quite," Connie confirmed. "Mark will reach out to you to invite you over. Treat it just like babysitting, and an overnight might occur if it works out that way, and if you're OK with it. I'll secure any other details with you via text."

At their house where my car had been left, I got out and hugged Connie not only to thank her for the shopping trip and bag full of goodies, but for the experience and discussion. She invited me in to see Mark for a short visit since the kids were still at school for another two hours.

"Steph!" Mark greeted me and brought me into his arms for a hug as he usually did. "How was shopping?"

"Steph and I had a lovely chat this afternoon," Connie explained as she took a seat and began pulling out one piece of lingerie at a time to cut off the tags & put them in a pile to be washed, presumably. "It seems that she's willing to come over during Christmas break while the kids and I are away."

"Really?" Mark asked and held me to his side with a hard squeeze. "Well, won't that be nice. See, honey? I told you it would work out. I won't be alone all that time after all. And you were worried," he accused.

"I just don't want you to be lonely, babe," Connie argued. "I think that Stephanie will be exactly what you need to get by until we get back."

"I'm looking forward to it," I assured him and nodded. "Well, listen. I had better get home. Finals are next week, and then I have to get myself set up for working full time for the month before school starts again."

"Full time?" Mark questioned. "Will you have time to come over to spend some time with me? You won't be too tired, will you?"

"I think we can work things out," I responded and hugged his side again. I walked over to Connie who stood up quickly. "Thanks again. It really was such a nice day today."

"Yes, it was," she agreed and then began to hug me. In my ear, she whispered, "Take that bag home, cut off all the tags, and wash them first in a delicate-only load. Take some time to look at the pieces and try them on. I'll be in touch soon."

After squeezing her tightly, I nodded in reply and made my way out to the car to head home, I had some work to do before my parents and siblings were home for the evening.

***

"We would like for you to come babysit* on the 23rd (Christmas party) at 6pm, 27th overnight from 5:30pm - 10am the next day (night shift for both M/C), and NYE from 6:30pm until the next early morning (party)."

As I read the text, I felt a sudden jolt in my belly. The schedule had been set at work, and I had passed it along to Connie as requested. She must have sorted through it to see when it would work best to go spend time at their house. I wrote on the family calendar the three times I'd be needed over there, and then went to my room to add them to my own calendar.