tagErotic CouplingsOh Baby! What a Sitter! Pt. 02

Oh Baby! What a Sitter! Pt. 02


Many thanks to those who read and enjoyed the first part of this story. Thank you, as well, for your patience while this second chapter germinated in my mind.

As always, all characters are over the age of eighteen.

If you would be so kind, please cast your votes when you finish reading. Comments and feedback are appreciated. Enjoy.


Six weeks in Toledo. No disrespect to the citizens of that fair town, but it was going to be hell. Not only was it going to take me away from my daughter, but I had just, and at long last, found someone slightly taller and more mature to love. More curvaceous too. Does Murphy's Law apply to relationships?

My first thought was that I would go to Toledo, get settled, then send for my girls. We'd be together, Kelly would get a free vacation (yeah, I know... vacation in Toledo...Oh boy!) and all would be good. That idea lasted about thirty seconds.

I walked into my sumptuous accommodations at the Toledo Holiday Inn...and found a roommate. So much for bringing roommates of my own.

His name was Tony, and he had been brought in for similar reasons. Apparently, John Lewis hadn't been the only one in the car. He had been coming back from a meeting, with another staff member riding shotgun. Tony was here to run their HR department, while I ran the whole show.

Shit. My life had just been changed for the better, then I get sent here. Okay, so we'll make lemonade, and bring Kelly here. Now the lemons are rotten. Shit!

I called Kelly to let her know I arrived safely, and to give her the bad news. She was disappointed, but put her usual, cheerful spin on it.

"Don't worry about us here. We're having a great time bonding. By the time you get back, we'll have the place repainted pink. It'll be a girl's house. How do you feel about a lifesize 'my little pony' on the living room wall?"

"It wouldn't be my first choice," I laughed. She was one of a kind. "Are you sure you'll be okay?"

"I'm not saying I won't miss you," she pouted, "but I do have my trusty vibrator to get me through, and the memory of our Sunday night send off. We'll talk every night, right? Skype for Lynn. I could dress for you, or better yet, undress for you... "

"I'd love that, but I have a roommate, remember?" I groaned. "Kind of hard to watch you without wanting to jerk off. Privacy is a little short around here."

"Right. I don't want to make it worse for you. No x-rated calls or Skype, unless the opportunity presents itself," she giggled. "Agreed?"

"Agreed. I should go, honey," I said. This conversation was depressing me, reminding me what I'd be missing. "I'll call you tonight."

"Okay, baby," she purred, "talk to you later."

I sat there, suddenly feeling very, very alone. The phone in my hand was my lifeline, back to where I desperately wanted to be. My mind wandered back to last night. Oh, what a night.

We knew it would be our last night for quite some time. Thank god Lynn was fast asleep, because we went at it like rabbits, and it wasn't confined to the bedroom. It was like something from a movie, where the lust just boils over, and the characters can't get enough of each other.

We left a trail of knocked over furniture, crooked paintings, and wrinkled rugs, as we fucked throughout the house. On the floor, the couch, standing in the hallway...out onto the deck, back in to the kitchen, dining room, and finally the bedroom. I came three times...once in, once on, and once down her throat. Her orgasms were more than I could count, and seemed to only add to her energy level. Well, I guess she was only nineteen. I felt older than my twenty-six years, but being around her was restoring my youth.

She gave me a wonderful goodbye blowjob Monday morning, and now I was here. Horny as hell, with only my hand for companionship. Oh...and Tony, hence the problem. Shit, shit, shit!


Tuesday morning, Tony and I carpooled to work. I was thankful for the distraction. Last night's bedtime Skype call had been heart rending, with tears from Lynn, then from Kelly and me as well. My little girl didn't understand. Kelly was doing her best to ease the pain.

The Toledo office was pretty typical, with one obvious exception. It had more women than usual, or at least, more than my usual office. More women was not what I needed now, and I certainly didn't need more attractive, friendly women, but that's what I got, from the first step through the door.

"Holy shit," Tony whispered. "I think I'm going to like it here."

The receptionist, Denise, a tall, pretty blonde, with a very athletic aire, showed us to our offices. I was first.

"Mr. Stewart, this is Adrienne, your assistant. I'll leave you with her. It was nice meeting you." Denise turned away, and Tony followed, leering at her ass.

"Mr. Stewart," Adrienne said, extending her hand. I took it. She was a dark haired, slightly Hispanic looking, quite attractive woman. Perhaps a little on the plump side, but she carried it very well, including a positively huge pair of tits. Just what I didn't need.

We talked a bit, introductory chit chat. She learned I was a widower and single parent. I learned she was single, thirty, and had been John Lewis's assistant for six years. I was glad she was experienced ; I'd need her help. The single and thirty bit had me concerned, as she did seem a little too happy to hear I was unattached. Maybe I should have told her about Kelly, and that she was more than just my babysitter. More than she needed to know at this point, I decided.

We got to work, and thankfully, she didn't appear to be actively stalking me. The day progressed quickly, and before I knew it, lunchtime had arrived. My new best friend, Tony, stopped by my office to invite me out.

Oh, what the hell. It beats eating alone, I thought. I didn't know he had also invited Denise.


As it turned out, besides being pretty and the object of Tony's lust, Denise was also a font of information about the ins and outs of the office. I mean that literally. Seems a few of the staff were more than merely friendly. Some were more than friendly with more than one other staff member. Denise said she was a lesbian, but she winked at me when she said it, so it may have been just to get Tony off her trail.

She delighted in filling us in on the gossip, and regaled us all through lunch. Adrienne was a source of concern. Denise said she really liked to fuck, and had an on again, off again thing with her boss. Since that was me for the next six weeks or so, I would have to watch her. I didn't want anything to jeopardize my relationship with Kelly. Otherwise, I would have happily gone back from lunch and bent her over my desk. Maybe Tony would like a shot at her?

The afternoon went quickly, and Tony took the passenger seat for our trip back to the hotel.

"So," he smiled, predictably, "your assistant's packing quite the pair, and likes to do her boss, huh? You gonna go for it?" Funny, he didn't look thirteen.

"Nope," I said. I didn't feel the need to say more.

"Are you gay, married, or just nuts?" he laughed. "I'm going to get all I can. No one will ever know."

But I would, I thought. I guess I'm just not meant to cheat.


"How was work, honey," Kelly asked from the screen of my tablet. She was playing up the domestic bit, fully buttoned and wearing a scarf. I laughed.

"You don't have to wear a disguise, just don't tease me too much."

"Yeah, I'm just playing," she giggled, tossing her head back. The scarf disappeared, and she undid a few buttons. "How's that? Less like your Mom?"

"Yes, thank you. Maybe one more?," I asked. I couldn't see any cleavage at all.

"You're sure? These breasts are pretty powerful. Can you handle them?"

"Oh, you have no idea how much I'd like to handle them right now," I laughed. Her fingers dispatched two buttons, giving me a nice crease to feast my eyes on.

"Where's your roomie?" she asked.

"Downstairs, in the bar, probably hitting on anything in a skirt," I told her.

"Really? So you're alone?" Her fingers opened a few more buttons. No bra to be seen, just smooth round curves. She pulled her blouse fully open. "Wanna play?"

Oh,... what the hell. Tony would likely be hours. I didn't figure to take that long.

I got up and went into the bathroom, propping the tablet up on some towels. Kelly had vanished from view, but reappeared, naked and holding her vibrator, in a minute.

"Do you miss me?" she smiled, leaning back against the headboard of 'our' bed. My view was straight up her body, from between her legs. She diddled her clit with two fingers. "Any pretty girls there?"

"Yes, I miss you baby, and yes, the office is chock full of women," I said. Honesty had better be the best policy, or I'd be in trouble.

"Any you'd like to fuck? If I wasn't around, I mean." Her fingers parted her labia, showing me the wet, pink interior.

Okay, even honesty has limits. I'm not answering that one...quite.

"Maybe," I replied.

"Uh huh," she moaned. "I figured as much. You're such a man. So, I assume she has big tits, right?" Her fingers were busy, dipping into her pussy.

Shit, she's known me for a few days recently, and she has me figured out already? Am I that predictable? Are men that predictable?

"Yeah, she does," I sighed.

"I thought so. You know, I told you I didn't have an agenda, and I meant it," she whispered, turning on the vibrator. It slowly disappeared into her vagina. "If you want...Oh shit, that feels great...if you want to fuck someone else, then do it. It works both ways."

Call me old fashioned, but I didn't expect her to say that. It caught me off guard. I said nothing.

"Todd? Are you still there?" she asked, sitting up.

"Yeah, I'm here," I answered. She read the tone of my voice.

"I'm not telling you to fuck her, just that I'd understand if you wanted to," she whispered, looking into the camera closely. "I'm not going anywhere, baby, and I'm not looking for anyone else. Obviously, I'd like us to be exclusive, but..."

"Then that's the way it will be," I interrupted, without even thinking. My subconscious had made that decision already. I knew the implications, and what it sounded like. So did she. The smile that shone back at me on the screen was breathtaking.

"Really? Already? I feel something for you too. I've just been afraid to say it," she said happily. "God, I miss you so much! I don't know how I'll survive six weeks!"

As if to make things worse, I heard the door to the suite open, as Tony returned.

"Shit!" I whispered. "We're not alone anymore. I think we're going to need to put this on hold. Sorry, honey."

"That's okay, baby. I can wait," she whispered back. "I feel better now that we've committed to each other. Until tomorrow, then?"

"Until tomorrow," I replied. She blew me a kiss, and the screen went black.

Tomorrow, I thought. Tomorrow, I call head office, and amend our arrangements.


Thursday night arrived, and I was looking forward to my call with Lynn and Kelly. I had good news.

Since this was the early call, timed for Lynn's bedtime, I had two faces looking back at me on the screen. They were so cute together.

"I have a surprise for both of you," I said, smiling brightly. For some reason, I continued the conversation as though Lynn could understand all of it. "Daddy called his bosses yesterday and told them that, if they wanted him to do this job, he'd need to make a few changes. It wasn't fair to Daddy's family for him to be away from them for so long." Kelly seemed to know where this was going, and gasped. "So, today they told Daddy that he could come home, every weekend. I will be home tomorrow night!"

On my end, I heard lots of 'hooray, Daddy's coming home' and the like, as my girls celebrated. Kelly put her hands over Lynn's ears, and stared into the screen.

"Oh, you are going to get fucked so hard when you get home!" she giggled. "You'd better call me back when you're alone, because I want to tell you all about what I'm going to do to you."

"Hey baby, you're not the only one who's horny, you know? I've got a few things I'd like to do to you, too!" I growled.

"Ooooooo, it's a date!" she smiled. Her hands came off Lynn's ears. "Okay, Lynnie, my little darling. We should let Daddy go now. It's time for you to go beddy-byes, and the faster you get to sleep, the faster Daddy gets home!" The message worked, as Lynn dropped off screen. I could hear her running to her room. Kelly shrugged, then looked back at me. "You," she breathed, pointing at the camera, "I'll see you later, and I want to see that big cock, hard and in your hand. This isn't a one way peep show, you know?" She giggled, and fluttered her fingertips, then the screen went dark.


Later took almost two hours to arrive. Tony finally went out, with a girl, this time, so he'd be occupied. I went into the bathroom with my tablet.

My dick was way ahead of me, getting hard before I even pushed the button to call Kelly. She answered on the second ring, obviously as eager as I was. Every bit as naked, too.

"It's about time," she laughed. "I have a confession to make. I couldn't wait. I've been playing with my pussy for hours. See?" The camera panned down, showing her fingers, toying with her lips. She was visibly dripping wet, with little strings of fluid sticking to her fingers as she pulled them out. You could hear her cunt making squishy noises.

"Uh huh. I see that. How many times have you cum, you bad girl?" I asked, stroking myself slowly.

"Oh, I don't know...three... seven...fifteen...enough that I'm a train wreck," she groaned.

"I'd better catch up," I laughed, reaching for the small bottle of hand lotion on the countertop. I squeezed some onto my cock. Kelly was watching.

"Mmmmm, that looks delicious," she hissed. "I wonder what percentage of the hand lotion provided by hotels actually gets used on hands?"

"Hey, it's getting on my hands," I replied, "one of them anyway. Just using an applicator, that's all."

"Yeah, well I'd really like to be there to suck your 'applicator', you stud. Jerk that big cock for me baby," she whispered.

"You like to suck my cock?" I prodded, hoping she'd continue the dialogue.

"Mmmm, oh yes," she moaned. "I just love the velvety, soft skin on your glans. It feels so good on my tongue, and contrasts the hot, hard texture of the shaft. It gets me so...Oh, if I was only there right now, you'd see what it does to me. It's almost as good as having it in my little pussy, feeling that huge thing pressing inside me, touching the places that it was made to touch. Oh fuck... I'm gonna cum again!" Her head tilted back, and she wailed loudly. It was great to watch, and I was stroking myself firmly.

"Oh god, I'm going to sleep well tonight...alone, but well," she whispered. "I can't wait until I get your dick inside me again."

"Feels good, does it?" She was stroking my ego, and I was doing the rest.

"Oh yes, baby, but unless you're a closet homosexual, you wouldn't understand. You need to experience it," she said, smiling lazily. "Of course, they use the other entrance. Never really cared for it, myself."

I froze. My hand stopped midway along my cock. Did she just say what I think she said?

"Kelly? You've taken it in the ass?" I moaned.

"Yeah...'taken' is the word. It wasn't my idea, and the guy didn't know what 'gentle' meant. It hurt more than the pleasure was worth." She looked directly into the camera. "Does that interest you? Excite you?"

My hand was a blur. She saw the movement.

"It does! Ooooooo, yes! Okay, baby...my ass is yours," she growled, suddenly energized. "Think of your big cock, stuffing my little asshole full!"

I was way ahead of her. My mind was running amok with images of Kelly's tight little bung hole stretched wide around my pole, while I pounded her mercilessly. I have no idea why the idea was this appealing. I'd never done it before.

"Cum for me baby," she urged. "Let me see that jizz fly!"

I looked at the little inset picture on the screen...the one that shows what she was seeing. The angles looked good, my inner director said. Action!

"Oh shit!" I groaned, as the first spurt shot from the head of my dick. Again and again, I felt the exquisite surge of pleasure, as I sprayed cum across the countertop. I collapsed back to sit on the toilet seat.

Amid my gasping breaths, I heard Kelly moaning and laughing. The moans I understood, but the laughs were a puzzle.

"That was impressive," Kelly's voice said. I had my eyes closed, resting my head against the wall. "Um, honey, are you okay? I can't see you."

I grabbed the tablet and turned it to face me. "I'm here, see?"

"Not really," she giggled. "Check your camera."

That would require focus, something I was having difficulty doing right now. I looked where she wanted me to.

A big glob of cum was dripping slowly down the screen. I had hit the bullseye, right over the little circle in the tablet frame that showed her my end of things. I grabbed a tissue, and cleaned it off.

"Sorry," I laughed.

"Don't be sorry...that was the whole point, wasn't it?" she smiled. "It was like a facial, without the mess. Too bad really...I like the mess. Perhaps you could save some for me? Tomorrow night?"

I did a quick calculation. Flight out at this time, for so many minutes. Get the rental car they were also paying for, and drive home.

"I should see you two about eight," I said. Kelly smiled back.

"Perfect. Lynn ought to last about an hour before she runs out of gas," she whispered, "then you're all mine. Don't skip any meals. You'll need your energy."

Right. Perhaps some Red Bull, just in case.


I pulled into my driveway. It was just before eight o'clock, still light out. I turned the key off, and took a deep breath. I was home...for just less than two days, before going back to Toledo. Still, two days was better than waiting another five weeks.

Today had been a study in contrasts. The workday had been excruciatingly slow to pass, because it wasn't busy enough to distract me. Then everything was happening almost too fast. I nearly missed my flight. Thankfully, I made it just in time, and then could relax. Now I was here, early, and feeling butterflies.

The front door opened, and Lynn came charging out of the house, racing around to my side of the car. I scooped her up as I got out, and held her tight.

"Daddy! Daddy! Daddy!" she giggled, wrapping her little arms around my neck and squeezing. "I miss you Daddy!" She gave me a big kiss on the cheek. Actually, several.

Kelly stood in the doorway, arms crossed, wearing a big smile. She let us have our moment, deferring her own greeting until Lynn was done. She had the patience of Job, and didn't interfere at all.

With Lynn in one arm, and my carry-on bag in the other, I paused at the doorway, and leaned over so Kelly could give me a peck of greeting.

"I don't want to get started, because I might not be able to stop," she whispered. "You two get reacquainted. Can I get you anything?"

"No thanks," I laughed. Lynn was still hugging the stuffing out of me. I could hardly wait for Kelly's turn. "How was your day?" Kelly laughed.

"Oh...you know how they say 'time flies when you're having fun'?" she asked.

"Yes, I've heard that. Why?"

"Well, it sure doesn't fly when you're not," she said. "Lynn had a difficult day. She wanted you to come home sooner, and I know she doesn't understand, so I tried everything to keep her happy. I'm just not her Daddy," she shrugged, actually looking upset that she hadn't been accepted yet.

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