The Confession Pt. 05: The Island

Story Info
Donna weekends with her Boss and his friend on an island.
8.9k words
3.74
19.4k
15
12
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

The Confession Part 5: The Island

So, after my weekend sex adventure with my boss, Larry, work went on as normal. Busy, obnoxious customers, drama with the staff. Early in the morning Larry called me into his office. My stomach lurched with nerves. He'd told me on our boat ride that I have no secrets from the people I work with. They already knew about the worst thing that had happened to me, and all they did was gossip behind their hands.

This would just add to the noise.

Larry's office is tiny. He leaned past me to lock the door and I crowded as far away as I could get into the corner. He stayed in front of his desk at the other side of the cramped space.

"Donna, you were remarkable the other day," Larry leaned awkwardly against his desk. "I've never had sex like that before. And you came so hard, it was amazing. You're special."

I smiled at the compliment. I thought I knew what was coming. Despite our agreement not to have an affair, he would propose some arrangements. I'd have to say no, and then we would get awkward at work.

"Did you tell your husband about our boat ride?" Larry watched me like a cat watches a mouse. Just waiting for my tail to twitch.

"Yes..."

Larry's eyes hooded with lust. "Were you excited to tell him what we did?"

I swallowed hard. "Y...y...yes..."

Larry's probing had the same effect as if he was rubbing my pussy.

"Will you tell him about the next time we have sex?"

I just nodded my head. I tried to keep my cool, but it had left.

Larry leaned into me and kissed me.

My good intentions disappeared as I opened my mouth and melted into his arms. His erection pressed hard at my stomach. His hands rubbed my breasts and butt. Even through all my layers of clothes his touch fed the fire in my pussy. I grabbed his cock and rubbed it through his pants.

He pulled at his belt. I undid my jeans and pushed them down. He pushed me to lean over his desk. I grabbed the far edge when he slipped his cock into my soaking wet pussy.

I wanted to cry out in pleasure, but I bit my hand as he pounded me harder and harder. His desk shook under us. Then Larry stiffened and his cum jetted into my pussy. I clamped down hard as my own orgasm peaked. I grunted and Larry laid across my back for a moment.

We laid their gasping, with his hand still tweaking my right nipple and his big, thick cock slowly softening. When it finally slipped out of me, he stood up and pulled up his pants. I wiped at the mess between my legs with a napkin before I pulled up my pants, knowing I'd be walking around for another couple of hours with his cum sloshing in my pussy.

I started to panic "We can't do this. We said no affair."

"I know. But this is fun, right?" Larry rubbed his fingers through his hair. He wasn't the type who people said 'no' to, but I did. Well, I tried to.

"I'm going to walk out of this office and people are going to guess we just had sex."

"No, they won't." Larry tried to smile.

"That's the way our minds work. Plus, I'm going to be walking funny with your cum in my pussy."

Larry just looked at me. What was he thinking? Was he going to fire me, now?

I took a deep breath. The panic receded a bit. I firmed my voice up. Not angry but like I was talking to a child who didn't want to follow the rules. "We said no affair. That means no affair. No sex at work. No sneaking around to motel rooms or each other's houses. You don't get to call me into the office and molest me while my co-workers talk about me fucking the boss. Do you understand me?"

Larry nodded. "But I thought you just..."

I waved it away. "This is naughty and dirty, and it turns me on. But I can't keep doing this. But ask me nice if you want me go on another boat ride. If I want to, I'll go. If I don't, I'll tell you." I opened the door. Kathy ducked around the corner. She'd probably heard the whole thing.

****

Three days later...

When I got home Dave was already there. I undid my jeans and pushed his hand into the mess between my legs.

He grinned at me. "You've been a bad girl."

"Yeah. Larry."

"Did you tell him 'No' again?" Dave pushed a finger into the slippery mess in my still tingling pussy.

"Yeah, after we did it. I'm a slut."

"Did he tip you again?"

I rummaged in my apron and pulled out the two folded hundreds that Larry must have stuffed in there. "Yup. I'm a whore. Pretty sure the rest of the diner knows it."

"Why?"

"Kathy sent a trucker over to talk to me." I looked Dave in the eye. "He started chatting me up while I was doing my checks."

"That happens. Why do you think Kathy sent him?"

"She was watching when he offered me fifty bucks to go to his truck with him."

Dave grinned at me some more as he felt for my g-spot. "And..."

"I told him I wasn't a lot lizard."

Dave looked at me. He knew there was more.

"Then I said he couldn't afford me. He didn't like the answer, so he huffed off. Kathy didn't miss a minute of that. She ran over and asked me what happened."

"Did you tell her?"

"I told her I don't work parking lots."

"But you didn't tell her you weren't taking money for sex."

"I'm not a whore."

Dave picked up the two hundred dollars. "It's OK with me. As long as you're having fun with it. I'd prefer you didn't undersell yourself, but charge for it if you want."

I turned beet red and looked away from him. I didn't want him to see what I was thinking. Larry's 'tip' for sex had been more than I'd made the rest of the week. Dave's hall pass could pay a lot of bills if I was careful.

"Larry wants me to go out with him and a friend this weekend. Do you know what that means?" I had to watch his reaction. I couldn't believe I was telling him something like this.

Dave shivered and bit his lip. "That means he wants share you with his friend."

"Yeah. He's already sure I'm easy and willing to trade sex for money. He likes me, but if he's going to use me like a party favor...."

"Did he offer you money for sex?" Dave took on that look he had when he wanted to argue a point.

"No. He just said he had a friend who wanted to come out for the weekend." I mumbled.

"Did he say what he wanted from you?" Dave licked his lips. He wanted something explicit to think about while I was gone. The pervert...

"He said he wanted me to cook for them. And keep them from being bored when they weren't fishing." I looked away again. "He said there was a guest room for me or I could sleep with him."

"So, he doesn't expect to share you with his buddy?" Dave sounded a little disappointed.

"Do you want me to have sex with two men at a time this weekend? Isn't one boyfriend enough?"

"You never know, you might enjoy being with two guys at once..." Dave kissed me.

I shuddered because the thought of having two sets of lips, four hands and two cocks straining for me raised my temperature. My inner slut liked the idea.

"Christ, I hope not. Having you and Larry is bad enough."

"It's not like we haven't had sex four or five times in a row."

"Not the same thing," I grabbed him. "That's you. I love you."

"You did it three times with Larry on the boat trip" Dave grinned at me in his infuriating way. "And with me every day after."

"Yeah well." My cheeks flushed hot.

"Didn't break, did it?"

"No. But it's getting tender."

"And how many times have you and Larry done the nasty at work?" Dave found my G-spot and I groaned.

"Stop that..." I didn't mean it and he didn't pay attention. I pulled him to me. "It's been every day this week and twice on Tuesday."

"He definitely likes you."

"Yes, I suppose he does...." By the time I had this revelation, my clothes had reached the floor. Dave lifted me onto the waterbed and settled between my legs, his hard cock sliding into my messy pussy with ease. He started a slow rhythmic slide, in and out of my pussy with his cock pulling almost completely out at the end of each stroke.

I moaned and dug into his back as he pushed my legs over his shoulders. The improved access took him to my G-spot, and I started clenching. "Oh gawd....."

Dave's stamina is remarkable. He kept going as I thrashed and moaned. The cum and pussy juice already lubricating my pussy made obscene slurping noises as he thrust in and out. His crescendo built until we both seized and cried out.

****

Dave:

The next day I came home at lunch. Donna had the day off. A pickup was parked in our driveway next to her Grand Am. My cock had a good idea what was going on. Nearly constant sex for a week was making both of us a little lust crazy.

I went to our bedroom window. I could hear them going at it before I got there. The rhythmic pounding of the headboard on the outside wall made it clear what was happening. As I got closer, I could hear Donna moaning loudly. I leaned against the window and could see her, on her back with Larry's big hairy body between her legs and his ass pumping up in the air.

I didn't like Larry. He was an arrogant asshole. But Donna liked him well enough to fuck him, so watching them was a weird mix of jealousy and satisfaction. Very hard to get my head around. So, all I could do was watch with my cock straining in my pants.

She had her arms and legs wrapped around him and met his thrusts with her hips rising. I could imagine the sloppy sound of his balls slapping her pussy, her pussy pulsing around his dick as she came. Then Larry stiffened and groaned. He jerked and buried his cock deeper into her as he spewed cum.

They shuddered and kissed, then he rolled off to go to the bathroom. Donna looked at me, looking at her through the window, and waved at me to go away. She got up and put a robe on.

Our kitchen is just past the bathroom with a window I could easily see through. I watched as Larry kissed Donna by the sink. The kiss deepened quickly. It was obvious the passion hadn't lessened between them. Larry's hands slipped inside of Donna's robe to stroke her hard nipples the way that drives her crazy and Donna undid his pants and pushed them off of his hips.

Larry's substantial cock sprang free like he hadn't just cum in my wife, and he turned Donna around. He fit his cock between her legs and pushed it all the way into her well lubricated pussy. They stood there, thrusting frantically at each other until Larry stiffened once again. When he was done, he pulled up his pants, and kissed my wife long and hard. When the kiss finally broke, he stuck his hand in his pants pocket and pulled out some folded bills. He pushed these into Donna's hand and went to the door.

I waited for Larry's truck to start and leave before I went inside. Donna was still leaning against the counter, red faced with streaks of jizz running down her legs.

"Still want me to have a hall pass?" she said.

"This is more than a hall pass. You've got a business venture going here. I thought you were taking the day off."

"Larry wanted to make the arrangements for the boat trip. It's getting more complicated."

"What do you mean?"

"He wants me to spend the night with him at the motel by the boat dock. As well as fix meals for them on the trip. And wear a bikini or less all the time. I'm supposed to supply the eye candy. He's got an island where we can camp on Saturday night. He intends to fish Sunday morning and have me back to shore by dinner time."

"And the whole time you're going to be servicing both of them?" I asked, my cock aching harder.

"Larry's paying me to cook. I told him I'm not going to whore myself out. It's not happening." Donna looked at me hard. "And he agreed."

"And he's not going to want to have sex?" I didn't believe it.

"The only reason I'm going is to have wild monkey sex with Larry. He still makes me cum so hard." Donna blushed.

"So, you aren't going to fuck the other guy?"

Donna looked at me with a sad introspective look. "This thing with Larry has been crazy sexy. Throw another guy in the mix? Depends on the guy. I don't know if I want to just fuck somebody. I think they'd have to be attractive and a nice person. But not two at a time. I'm not a whore."

"Larry's a nice person?" I found that statement hard to believe.

"He always has been with me." Donna searched my face for some sign of my reaction.

"I love you." I leaned in and kissed her. Mimicking Larry from half an hour before I reached inside of her dressing gown and cupped her breast. Her eraser shaped nipple hardened under my touch. Our tongues danced. I could smell Larry's aftershave on her. She dug at my belt and unfastened my pants, pushing them to the ground over my steel hard erection.

Then I lifted her up and sat her on my cock. I slid in with no effective resistance and she clamped her legs around my back. I leaned her onto the counter and started pumping her hard. The combination of fantasy lust and Larry's jizz all around my cock brought my orgasm on fast. I don't Donna's had stopped from having sex with Larry. She clenched at my cock all the time I pounded her.

My cock pulsed streamers into her pussy. I shot more cum than I thought possible until her pussy overflowed and dripped on the counter and the floor.

We staggered as I got her to her feet and pulled my pants off of the floor. She slipped into the bathroom to clean herself.

I made a cup of coffee and a sandwich.

Was this going too far? Larry was at my house, fucking my wife and paying her to go on a camping trip with him and his friend. I munched my sandwich, and rubbed my, once again, rock hard cock. Despite what Donna said, Larry was paying for sex. What would happen when she realized he did think she was selling sex?

Donna came out of the bathroom, red-faced and smelling of soap. I offered her the rest of my sandwich and fixed her a coffee. We sat at the table and stared at each other, the pile of Larry's money in front of us. I counted the roll while Donna ate. Larry had left $600 in twenties and fifties. He must be impressed.

"Do you want to do this?" I asked her. "I think Larry thinks he's paying for sex."

"I dunno. This is more than a little naughty. Just the idea of being with two men is overboard. But getting paid? Been there, done that, don't want to go back. I'm not property to be bought and paid for." Donna squeezed my hand.

"So, are you going to go? Despite the expectations?"

Donna bit her lip. "The sex has been good. Larry is a passionate lover."

"Best you ever had?"

Donna blushed. "I wouldn't say that, but he's new and hot and it's so bad what I'm doing..."

"I got a rush watching you with Larry today. Brings a whole new level of visualization to your stories and to thinking about what you're doing. I'll miss you this weekend, but I can imagine you with your legs in the air or bent over a bench getting pounded. And I hope you'll have something left for me on Sunday night."

Donna blushed, then she squeezed my leg and kissed me. "I need to get packed before the kids get home from school. Larry expects me there by six for dinner."

****

Donna:

I was a bad girl. I ditched my kids with Dave to go away for the weekend with another man. I was a slut. My first husband had called me a whore and a slut, and he was right. If Dave was right, and Larry's gifts sure made it look that way, I was a well-paid slut. Thank gawd my second husband loved me doing whatever I wanted.

I rolled into the Landing where Larry kept his boat and parked by the little motel and restaurant. I still wasn't sure what I wanted this weekend. We were meeting in the restaurant for drinks and dinner before heading off to the room. To have sex, I expected. But what about tomorrow and his friend? What did I want?

I got out of my car and locked it. I'd dressed special for Larry, tonight. My dress was dark and translucent, while not quite form fitting it followed my curves. Per Dave's suggestion I skipped the bra, so the gauzy material tented over my erect nipples.

Larry must have been watching the door when I walked in. His eyes never strayed from me as finished sipping his beer and set the glass down.

"Do you want a drink?" He said when I came up to him.

"Jack and Coke," I sat on the stool next to him. I was tense. A weekend date with another man was a big enough step. But bringing a friend along?

"Are you OK?" Larry asked, when my drink arrived.

I sucked in a big gulp. "Not really."

"What's the matter?"

I looked him in the eye and tried not to think about all the times he'd had his cock in me since last Saturday. "I'm not a whore. It's not like I want to screw a bunch of random guys. I have a stupid crush on my boss. The rest is all you. And my husband doesn't mind if I have an adventure or two so..."

"We said 'no affair'. That means it's a business proposition." Larry took a long pull on his beer.

"To you it's business. But you know what happened with Gerald. I won't be trapped into being a sex toy." I held Larry's hand. I liked sex with him, but I dreaded the idea of guaranteeing some random stranger's access to my pussy. Larry pressed a roll of bills into my hand.

"That's for this weekend. You came out because I asked you to. You don't have to do anything. Not with me, or with Doug, my business associate. I'll even get a cot to sleep on tonight so you can have the bed."

"Thank you for understanding," I kissed him. "I know I'm being a terrible slut and a bad wife, but what little self-respect I have is based on not doing what Gerald and Mac made me do."

"I understand. I respect you, and I know this is just for fun with your husband. You're not the only couple around here that has that kind of relationship. You're just the most honest." Larry ordered me another drink. "I just don't want to fall in love with you because that would make my life very complicated. So, I pretend you're an employee."

"I am an employee. Just not a sex employee."

"I get it. I'm serious. You don't have to sleep with me tonight, or at all this weekend, or ever again. I can make other arrangements and we can sleep separate tonight." Larry gave me his sincere businessman's face, like I've seen him use with his business partners.

"I should call you on that one, but I didn't come down here to sleep alone tonight." I dropped the 'gift' in my purse and drank my drink. At least Larry understood I wasn't for sale.

****

The next morning Larry and I prepared the boat for our overnight trip. We were in our bathing suits and tee shirts since the temperature was pushing 80 by seven o'clock. By 9 o'clock Larry greeted his friend on the dock. He looked younger than Larry and leaner with an infectious smile.

"Donna, I want you to meet Doug."

Doug looked me up and down. My oversized tee shirt hid most of my modest attributes. He smiled at me like he expected me to melt, "Hi Donna. Glad to meet you." And held out a hand.

His hand was dry and rough, like he worked outside.

"Hi Doug." I bit my lip. "Glad to meet you."

I looked at Larry who was industriously loading supplies in the cabin.

Doug climbed down into the boat, and I handed him my backpack and purse. "Please put those under the middle seat, in the storage area."

Larry had come out of the cabin. "Can you get the lines?"

"Sure." I unhitched the bow line. Larry started the big V8s that powered his boat.

I unhitched the stern line and climbed into the back of the boat. Doug leaned over the side and pushed us out from the dock as Larry engaged the drive and idled us out of the harbor.

Sweat made the tee shirt stick to my back as the wind, when we picked up speed, slapped the cloth against my skin. I looked over at Doug, who was apparently studying the river and the nearby islands. He wasn't staring at me, so I felt a little more comfortable. Larry was driving the boat. I pulled the tee shirt off and hung it on the cabin door. Now I was in my bikini, showing a lot of skin. I got the sunscreen out and started rubbing the cream into my skin.