Sis-in-law Incentives Ch. 06

Story Info
Another Goal, another hole, and Holly plays pretend.
3.8k words
4.72
274.1k
109

Part 6 of the 12 part series

Updated 10/25/2022
Created 08/10/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Tx Tall Tales
Tx Tall Tales
20,266 Followers

Ch 06: Payments and Play-acting


===========================

Another goal, another hole, and Holly plays pretend

===========================

I looked down at the scale. 202. At goal, minus an extra pound. Jenny owed me. And I was bound and determined to collect. Let me rephrase that. I was determined to collect, while she was bound. Oh, she wasn't bound yet, but after her little game with her friends, tying me up, I was going to make sure I collected in kind.

But fair was fair, and before I did collect I was going to make sure I could pay off my side of the deal. In this case, it was two new clients for Jenny. I'd already arranged for the first, by paying up Holly's training in full. That had turned out to be an incredibly good investment.

As for the second client...

* * *

"So how much do you want to lose, Alex?" I asked my office-neighbor.

"I don't know, probably around 40-50 lbs." He answered. We were at lunch. I was eating grilled mahi, with a side of steamed veggies. The fish was good, the veggies, Ok. His bacon-double-cheeseburger looked a lot more tempting, but the reward on the horizon made the clean-eating decision a lot more palatable.

"Ever thought about a personal trainer?" I queried between bites.

"Is that what you're doing? Must be a helluva trainer." He laughed.

If he only knew. But then again, in just a moment he would.

"So seriously, what would it be worth to you to lose all that weight? Get back in really great shape?" I pushed.

"Shit, the sky's the limit, for a guaranteed lean-mean body, but that doesn't look likely. I mean, I've been on and off diets and workout regimens as long as we've known each other. I must have spent $4000 on gym memberships and dues alone. Never mind another two grand on a 4 month boot-camp, which didn't do much. I even thought about going to one of the full-time camps, using my 10 year sabbatical. Six weeks of forced dieting. Then I saw the price. Ouch. Can you imagine 8 Grand for three weeks? Maybe that lapband thing is what I need."

"Let's just say 40lbs. What's that worth, do you think?"

"Shit, I'd pay 5 grand easy."

"Well, brother, I may have the solution for you," I told him lowering my voice.

* * *

It was late and the house was pretty quiet. Holly had gone to bed a while ago, and I was working in the media room when Jenny got home. I heard her putter around in the kitchen a bit before heading upstairs to her room. Heading down the darkened hallway, she couldn't help but notice the lights on in the media room at the end of the hall.

The media-room was pretty isolated from the rest of the house. It served as my home office, and was a large enclosed room over the 3-car garage. It was at the end of the hall of bedrooms upstairs. The order was: my daughter's room, her bathroom, the first guest bedroom, which Jen was using, the Jack-and-Jill bathroom for the two guest rooms, and finally the second guest bedroom, which was currently empty. Just last year I'd added a door to the end of the hallway, just before the media room, so I could have a little quiet while I was working. I usually just left that door open.

Jenny walked in and said hi, taking a seat on the couch in my room. She sounded a little nervous.

"Hi, long day?" I asked pleasantly.

"To say the least. I don't have that many customers, but I've really got to work on the scheduling. Killer days like today followed by half-full days. Plus the typical slow times in the early afternoon." She was just blowing off steam.

I opened the mini-fridge next to my desk and gave her a beer, which she didn't turn down.

"How's the workout coming?" she asked, after a sip.

"I'm at 201," I told her with a bit of a smirk.

"Wow! I knew you could do it." She was still acting nervous, and took a long drink.

"Now what was our deal?" I asked, slipping up next to her.

"At 202 pounds you'd be at goal, and you get to have me." She answered softly, reaching out and softly touching my leg.

"And what does 'have you' encompass?" I asked her.

"I've been thinking about that. How about if we say my mouth and my pussy are yours?" She looked over at me coquettishly.

"And what did you have in mind for the final goal?" I asked her, reaching out and stroking the side of her face.

"I'm yours. Whatever you want. Your toy. All openings, no rules, no holds barred." She said.

I couldn't believe it, she was blushing.

I was working in sweats and a t-shirt, so it didn't take much for me to drop my pants right in front of her. I wasn't hard yet, but that was easily fixed. I reached forward and pulled her pretty face toward my cock. She opened her mouth and took me inside, warm, wet, eager.

"I'm dying to fuck you, beautiful, but now's not the time. I think I'll just take a down-payment." I told her, sliding my pole between her lips.

She drew away. "How about just a taste? I'll be quiet. We won't count this as full payment."

"What exactly did you have in mind?" I asked her, curious.

"Let me clean up, and get ready for bed, I'll be back in a few minutes." She took a last suck on my cock, then disappeared down the hall.

A few minutes turned into about 20. Then she was walking through the door, and took care to close it behind her. She was wearing a long night shirt, that reached halfway down her thighs. It was almost sheer and it was clear that she was naked underneath.

I was relaxed, sitting on the couch, watching the TV. My pretty sister-in-law didn't hesitate to take up residence between my legs, and went about bringing me back to the state she'd left me in a few minutes before. I just sat back and enjoyed it, watching the sports recap, while this hot young girl sucked on my cock languidly, not working hard to get me to finish, just to pleasure me. I was hard, but not in urgent need of coming, and she kept at it, for at least 10 minutes, until the show ended. God, I was a lucky man. I caressed her head, running my fingers through her hair, enjoyed her warm mouth, and watched the news. Eat your heart out.

I turned off the TV with the remote, and she immediately pulled off of me, climbed onto the couch beside me, on her hands and knees. Her rear-end was raised in invitation, t-shirt hanging down, just barely covering her sweet ass.

God she looked tempting. I flipped the end of her shirt halfway up her back, exposing her ass and pussy. I rubbed the head of my sturdy cock up and down her slit. She was very moist, clearly ready to be filled. With a slow, fluid motion I answered her need, filling her. This was the fourth time I'd been inside of her (counting the blindfolded session as one), and I loved the feel. But I wanted to fuck her, fuck her hard, make her cry out. I'd never been in charge before, and yet I still had to maintain some control. So I screwed her slowly, watching that sexy little butt, picturing my cock penetrating her tight asshole, applying the full length of my cock to her burning tunnel. I wasn't in the least concerned with her pleasure this time. I was just going to enjoy fucking this beauty, until I blew my load inside of her, and thanks to her protracted oral attention that time was coming soon.

She was moaning, but I didn't care. I was close, and brought up the pace, pounding her, holding her hips tightly as I plunged her depths. I didn't even warn her, just slammed deep inside, and filled her with my searing cum. She whimpered, taking it, until I was done, and pulled out. I sat next to her, breathing heavily, as she turned to me wrapping herself around me.

"Thanks," I told her with a kiss, "that was nice."

"Mmmmm," she purred.

I watched as she reached out and delicately touched my half-hard cock. It was messy, and where she touched me she drew her finger away, with a combination of our juices, stretching like a string between us.

"You sure made a mess," she teased.

"Why don't you clean me up?" I told her.

"I'm comfortable, I don't want to get up right now." She pouted.

"You don't have to get up," I told her pushing her head toward my crotch.

"Oh, gross," she said, turning away.

"My cum grosses you out? You've had no problem with it before," I told her.

"It's not just that, it's the whole mess." She answered, leaning forward and appearing to smell me.

That looked naughty enough to cause me to twitch, and she jerked back.

"Suck me Jenny. Suck me clean, then suck me until I cum again." I told her, guiding her head where I desired.

"But you'll probably take forever," she hesitated, allowing her face to be dragged down to my crotch.

"Then you better get started," I teased.

She accepted her fate, and let her tongue reach out and taste me. Flick, hesitation. Flick, more hesitation. Then a longer lick, followed by another. Then she looked up at me as she cleansed me thoroughly, licking away at my cock until it was clean, before she actually went down on me again.

She sucked on me for about 10 minutes, then complained.

"My jaws are getting sore," she said, massaging her chin.

"Then ride me for a while, but I still want to finish in your mouth."

She sucked me for a bit longer, but gave up on getting me to come immediately, and finally lowered her slippery twat over my cock. I enjoyed her for a while, then I felt like I might come soon. I told her, and she quickly slipped off, and took my sticky, slimy cock, once again covered in both our juices, and swallowed it to the root. She bobbed away aggressively, and I enjoyed it, but the feeling of urgency departed. She pulled her mouth back and started stroking me feverishly.

"Sorry, false alarm. I thought I was going to come, but maybe not yet. Your hot little pussy *was* feeling really nice," I confessed.

She took the hint and rode me again. I was in heaven. When I was ready to finish, I told her.

"I'm almost ready to come, but don't stop yet, just be ready." I told her. She bounced away, drawing me onward.

"Now," I told her, pushing her away. She turned quickly and stroked my cock rapidly, her mouth open, wantonly, eagerly awaiting my deposit. She didn't have to wait long, as her actions delivered the desired result, and I unloaded in her mouth. She was careful to capture it all, sucking me clean again.

* * *

My wife is an early riser. Most nights she's in bed by 10:00pm. During the week, I usually go to bed with her, but usually get back up after she's asleep, and work on my side projects until about 1:00am. She's up by 6:00am and takes care of getting our daughter off to school. I used to wait until about 8:00am to get up. With my new exercise itinerary, I was getting up around 7:00, the extra hour spent working out. I'd started making sure I was in the sack no later than midnight.

Although I went to bed when Holly did usually, over the past several years it hadn't meant we'd been having sex. We had sex about once a week, rarely on the weekends, and almost never in the morning. Once the exercise program had started and Holly had returned home, we were going at it noticeably more often. I think the added fitness level was helping a lot, as was our slightly more in-sync sleeping schedule. It had been four days since the hot tub escapade but we hadn't talked about it. It was 10:30pm and I was lying down next to her, but thinking about getting up as soon as she was asleep, and letting Jenny suck me off again. She wasn't home yet, but I imagined she would be soon.

"Blow-jobs, huh?"

I turned with a start. Had I said something, half-asleep? I looked at my wife, looking at me.

"Where'd you come up with a drink like that?" She asked.

I answered sheepishly, "We had that full bottle of Bailey's, and I was going to make B-52's but we were out of Kahlua. Well, a B-52 without Kahlua just happens to be a Blow-job."

"And I'm supposed to believe that?"

"It's true! Of course once I had the idea of making Blow-jobs, well we had to go with the whole drinking method." I told her, almost believing it myself.

"And 'Buttery-Nipples'?" she kept on.

"Jeez! I had the Bailey's out anyway, so I just added some butterscotch schnapps, and voila."

"It was getting pretty wild out there; I'm sad I missed the end. What happened?" She asked. The question seemed simple enough, but the ramifications could be huge.

What did happen? How much could I say? "I suggested going in, but they wanted to finish the last shots..."

"The body shots too?" she asked, interrupting.

"Yeah, they had refilled their shots, then Dawn suggested that Beth be my first body shot, which was a little wilder than the previous ones, with more contact than I expected, and then Beth was done for the night, and headed in." I admitted.

"More contact?"

"Dawn salted her breasts," I confessed.

"That little slut. So she went in leaving you alone with Dawn." She added, pointedly.

"Yeah, and she was pretty much out of control. I mean as soon as Beth was gone, she wanted to do some necking, and stuff, but it didn't get too far out of line, and then I did a last body-shot on her."

"Did you fuck her out there?" She asked, and I didn't know if she was curious, or what.

Luckily I could answer this one honestly. "No. She fondled me a lot. She even talked about doing it, but she said she'd never cheated on JT and wasn't about to start on a night when she was that drunk."

"That's kind of an interesting statement," She laughed.

"I thought so to," I told her. "We got them dressed, and I took them home. Eric blew up when Beth got home, bombed. We obviously didn't tell him anything. Then I took Dawn home. When we got there I thought JT might be a little irritated, but he was more sorry that he wasn't there with us, with you girls skinny-dipping and all."

"You told him that?" she asked, sounding a bit shocked.

"Yeah, but that was all. Although I wouldn't be surprised by anything Dawn told him."

"When we went skinny-dipping, I never thought it would end up like it did." She admitted.

"Are you sorry?" I asked her.

"I don't know. I had mixed feeling afterwards, but during, damn, it was hot. I was really having a good time. I know you were." She confessed, with a laugh.

"If you girls ever get in that pool naked again, we're going to have to invite JT over," I teased.

"Maybe next time we have a 'girl's night out' you should invite JT over to watch a game or something," she said with a smile.

"You know, I think I'll do just that," I answered, bending over and giving her a deep kiss.

All I could think about was the likelihood there'd be a next time. I knew JT and I were up for it, I didn't doubt for a minute Dawn would play again. Now I knew that my loving wife wouldn't mind another round of naked night swimming, and maybe whatever else happened along with it. I hoped we could keep Beth involved. Who knows, maybe even drag in the sister.

The kiss developed into more than a kiss, and we settled into an easy rhythmic session. I enjoyed her, slowly, and she whispered to me, when my eyes were closed, "Which are you thinking about, Dawn or Beth?"

"Neither, honestly, I was just enjoying the moment." I told her.

"If you could have one of my friends, underneath you, legs spread for you, just like this, who would it be?" She asked huskily.

Crap, this was a dangerous line of questioning. I was wondering if it might not take a tangent into the area of her resident sister, which could really unravel things.

"I guess it would be Beth," I admitted eventually.

"Oh! Not the wild Dawn, but the ice queen Beth? So you think you could thaw her, huh? Maybe you could at that."

She thrust up at me, rolling her hips, moaning, with a southern drawl. Quite a decent imitation of our blonde neighbor. "Oh Alex, I've never felt anything like this, you're so big, so hard, filling me. Fuck me, Alex, fuck me hard, with that fat cock. Stick that monster cock up where no other man has been."

I couldn't help it, I was responding to the idea, both of fucking Beth, and of my wife encouraging it. I fucked her hard, "Like this?" I asked her, thrusting deeply.

"Gawd you're good, filling my pussy so tight," she murmured, still effecting the drawl. "Do you like doing this to me? Making me come for you?"

"I love fucking you. I love making you come." I answered.

She pulled me down close, "Close your eyes," she whispered, in her own voice. Once I did she held me tight. "Fuck her, fuck that uptight, silly dope, Beth. Fuck her hard, for me," she hissed. Then in her Beth voice, she encouraged me again, "Yes, fuck me Alex, stretch my pussy with your fat cock, so Eric won't even be able to feel the edges with his needle dick. Stretch me wide. Fuck me hard."

It was pushing me over the top. I fucked her wildly, pounding into her, pushing her legs back, spreading her wide.

"Do you like fucking me? Tell me you love it. I want to hear my name from your lips. Tell me." She was laying it on thick, her voice caressing me.

"I love fucking you, Beth," I whispered into her ear, "I'd love to fuck you all night, sweet, naughty, Beth."

We'd never played games like this before, but it was obviously getting to her as well.

"That's right, who am I? Who is your secret lover, Alex," she moaned, thrusting hard back at me.

"Just you, Beth. Sweet Beth. Hot little Beth. My hot little slut Beth," I groaned.

The last line pushed her over the edge and she was coming underneath me, moaning loudly, "fuck me, fuck me, fuck me," repeatedly, as she came on my cock.

Then I was coming in her, coming inside Beth/Holly, painting her insides with my hot cum. When my thrusts finally slowed, I rolled off of her, breathing hard.

"Whew! That was naughty," she said softly, with a giggle. "I almost thought I was her, feeling your fat cock for the first time, coming for the first time in years." She was quiet for a minute. "I don't want you trying anything bub. Don't get the wrong idea."

"Like that would go anywhere." I laughed.

"Just remember, you're mine. And if, and I mean IF, we were ever going to let you do anything like that, it's my decision."

I didn't know what to say, so the better part of valor told me to stay quiet, and pretend to be falling asleep. While my dear wife considered the possibility of seducing Beth for me. I changed my idea about getting up and letting my sister-in-law suck me off.

What a week.

* * *

The next day I ran into Beth at the local Lowes. I recognized her from behind, and slipped up next to her, falling in step with her.

"Hi gorgeous," I said.

She jumped a bit, then recognized me. "Hi Alex."

We chatted about our shopping, but I could tell she was nervous, and maybe a bit embarrassed.

"Are you thinking about our night-time swim?" I asked her finally.

She hesitated, and then looked down. "Yes."

"I'm sorry if we got you in trouble at home," I told her.

"No more than usual. Everything I do is wrong." She said bitterly.

"Hardly. Everything you did that night was very, very right." I answered glibly.

She stopped, and then looked around and pulled me down an aisle. "What did we do?" she asked me, anxiously.

"What do you remember?" I asked, cautiously.

"I have glimpses, scenes in my head of us doing some pretty wild things, some very naughty things. Some nasty things." She said, clearly embarrassed.

"That's about right." I told her, "and you were incredible."

"Oh Shit. And Dawn was there, wasn't she? I don't remember Holly being there when you were really bad, but Dawn was, wasn't she?"

"Dawn encouraged me to lick you, and she was there when you came on my tongue." I told her, leaning over and speaking softly in her ear.

"Were we really that bad?" she gasped.

"I loved tasting your tits, sucking your hard little nipples, and licking your pussy until you screamed." I leaned in very close, whispering in her ear, my lips brushing against her ear lobe. Facing the shelves, I eased a hand up to squeeze her tit.

Tx Tall Tales
Tx Tall Tales
20,266 Followers
12