Family Business & Sexual Adventures Pt. 02

Story Info
Bobby and ski bunny hook up, have fun.
5.5k words
4.38
10.7k
7
0

Part 2 of the 2 part series

Updated 06/09/2023
Created 03/11/2019
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
NerdySex
NerdySex
787 Followers

"Take my clothes off," Cathy asked. I lightly kissed her on the lips and then helped her pull off her white turtleneck. No bra. Two perfect B cups proudly poked out at me. I placed my hands on them and tweaked the nipples with my fingers. Bending over I licked first one nipple, then the other for a minute.

I unbuttoned her designer jeans and she shimmied out of them. Her panties were blue and low-rise. I knelt down and pulled them down her legs. My face was inches away from a young and beautiful, bare pussy. Sliding my index finger between her legs, I rubbed it along her pussy slit. She was already dripping.

"Now you." I pulled off my ski top and t-shirt. She knelt and unzipped my jeans, pushing them down my legs. My underwear was tenting.

"Looks interesting, Bob," she said as she pulled them down. My hard-as-a rock cock sprung out.

"Oh, beautiful. What a great cock you have. I was hoping I wouldn't be disappointed. It's just as big as Stan's."

I hated to hear that. I guess I wanted to think that ol' Stan had some little nub. Oh, well.

"What do you like to do? Would you like me to suck your cock?"

"Actually, I would love to eat your pussy."

"Oh, that will be wonderful. Stan rarely does it to me."

I licked and nibbled my way down her body and snuggled between her legs. I gently stroked along her pussy lips with my index finger, back and forth.

"Tell me about your other lovers," I asked as I nudged apart her lips with the tip of my tongue.

"The first was about two months after I met Stan. We were at this fancy hotel in Budapest. A friend from school days met us and we spent the evening going from bar to bar. By the time we got back to our room I was in a giggly mood, rubbing Stan's crotch and playing up to his friend. I was horny.

"Anyway Stan sat in a chair and watched his friend undress me. His friend wanted me to suck his cock. I had never done that before but knew what I should do. I must have been pretty good as he came in my mouth a few minutes later. I wasn't ready and choked a little.

"Then Stan stripped and shoved his cock into my pussy. He fucked me harder than usual and some minutes later filled me with cum as I also climaxed. I lay there for a minute, catching my breath. Stan pulled out and his friend pushed his cock into my sloppy pussy. I guess because he had already cum in my mouth he lasted a long time and I had two small climaxes."

While Cathy was talking my tongue was dipping into her pussy hole, then out and up and down her slit. I would give a lick at her clitoris, the back down between her lips. She had a nice clean taste. I lapped and sucked and nibbled, sucking every drop of her juice from between her lips. I continued to flick my tongue up and down and back and forth, alternating with thrusts into her tunnel and quick flicks across her clitoris.

"Oh, Bob, that feels so good. You have such a talented tongue. Yes, that's good. Oh, baby, you are making me feel so good.

"Anyway, I remember everything about that night. It was so exciting to have two guys want me. And I was happy that I sucked cock for the first time . . . Oh, honey, oh baby. Oh, I'm getting close. Go faster. Oh ..."

I held her hips as she bucked up against my tongue. A burst of juice covered my face. I was pleased and relieved that I could make her climax.

She placed her hands behind my head and mashed my face against her pussy. She climaxed again.

"Oh, damn, that was the best ever. No one has ever eating me so well. I think I came three times. You really know how to satisfy a woman. You ready to fuck me?"

I rubbed my cock head up and down her slit. I pushed the head into her pussy hole, then back out, continuing to slide it up and down between her lips. Each time the head would go in a bit deeper. I was teasing her with my cock.

"Damn it, Bob, put that cock in me. I want you. Do it."

She was very tight. I pushed and half of my cock entered her tight hole. The second thrust and I was fully buried in a very snug pussy. The walls of her pussy gripped his cock so hard I knew it wouldn't be long before I came deep inside her.

"God, Cathy, your pussy is so tight. I love how it makes my cock feel."

I took it slow, wanting it to last. As I sensed her growing excitement I increased my thrusts.

"Come inside me. Fill my pussy with your cum, baby, please. I want it so bad."

She lifted her hips off the bed to meet me. Within minutes I felt her pussy clamp down on my cock and I came a few seconds later. Not bad for first time together.

We snugged on the bed, enjoying the afterglow of good sex.

"You are as tight as a virgin, Cathy."

"That was some time ago," she giggled. "But thanks. I do vagina exercises. Stan likes me tight too and took me to a physical therapist who showed me how to keep my pussy toned. I guess it works. Now do you want to hear more about my exploits?"

"Sure, if you don't mind sharing."

"I don't mind. In fact, I like talking about it with you. I think sex is really fun but I never told anyone else other than Stan.

"That was the only time Stan shared me. A month later Stan was out of the country for two weeks. He gave me permission to have fun and I called a guy I knew from high school. We had been good friends, never lovers, but I did have a crush on him. After making arrangements by phone, I flew down to meet him.

"He was naturally surprised to hear from me, much less fly out to see him. Pizza and beer, and then I seduced him. He was always rather shy and was still pretty inexperienced at sex, especially compared with me. Initially I was rather disappointed, however."

"Why's that?"

"His cock was only two-thirds the size of Stan's. It felt ok in my pussy but didn't fill me up the same way. But I had always wondered about anal sex and thought his might be a good one to try. Some of my girlfriends tried it with mixed feelings. Anyway after we fucked I played with his cock and then sucked him back to hardness.

"I told him I wanted him in my ass. That was obviously his first time and it took some doing but we got it in. Unfortunately, he came almost immediately. The next day we tried it again. I played with my pussy and clitoris and came even before he did. When I went back home a week later I left him with some great memories.

"That's the only time I've had anal sex.

"There were two other times over the next year and a half where I took a lover while Stan was gone on an extended trip. He always asked what I did and I would give him a detailed recap. He told me he liked to hear about guys' cocks sliding into my pussy, that sort of thing.

"Of course most of the time I was with Stan. I told you he has a big cock, like yours. And he knows how to use it. We fuck all the time, sometime twice of day. You and I can fuck like that, if you like. Oh, I almost forgot. Stan told me that if I liked fucking you we could get together when he gets back. All three of us. It would be only the second time he has shared me, so very special. Would you be interested?"

"Absolutely. That would be fun. Really fun."

"And you wouldn't have a hang-up being close to another guy in bed? I would think some guys would."

"My brother, Jim, you haven't met him. He's a year older. Anyway he and I have double-teamed several girls. Sometimes we also double-date and swap back and forth in bed."

"Cool! I just had a feeling that you were pretty liberated. It's getting late, how about you going to your place and bring back some stuff? You can stay here until Stan gets back."

The next morning, I awoke with Cathy gripping my half-hard cock. She rolled on her side and I spooned against her back, my growing cock nestled between her ass cheeks. It was early and we were both still half asleep.

"Good morning."

"Good morning. What's that thing pressing against my ass?"

"I don't know. It has a mind of its own."

"Well, I need to pee," Cathy said as she rolled out of bed, not before shaking hands with my cock.

When she returned I made my trip to the bathroom. Cathy was nude, wearing only a big smile.

"Come fuck me, Bob. Does anyone call you Bobby?"

"Yeah, my family."

"Do I know you well enough to call you Bobby?"

"Honey, you can call me anything and I'll come. Bobby would be nice."

I rubbed my hard cock up and down her slid to get the head lubricated. A few gentle pushes and I was deep in her snug pussy. I kissed her as I started stroking in and out. Last night was heavy sex. This morning was gentle loving. What a beautiful girl.

Some minutes later I climaxed, pumping a big load into her pussy.

"Oh, Bobby, can you keep going? I'm not quite there."

My cock was already shrinking. Damn. But I had a solution, something I had done with a few other girls. I pulled out my cock and placed my tongue into her still gaping pussy.

"What are you doing, Bobby? I'm all messy down there... Oh, that does feel good. Never mind. Bobby, you are full of surprises. Oh, my. Oh, damn. Oh ... "

My face was wet with her juices and my cum. "Come here, Bobby. Kiss me."

"I taste like pussy and cum, better not."

"I want to taste. Come here."

We took a shower together and got dressed to go skiing. As we rode the first lift Cathy turned to me. "No one has ever done that to me. Did you like doing it?"

"Yes, absolutely. I felt bad that you didn't cum with my cock."

"You've done it before? Other girls?"

"A few special times."

"Isn't that kind of a gay thing, eating your own cum? I mean, I loved what you did, but damn, guy, that's unreal.

"I don't think of it that way. To me it's just a part of making love to someone very special."

"So I'm special? That makes me feel good. Do you like the taste of your cum? When I suck cock, to me it's just ok. Something I do. Guys like it when I swallow."

"I've never told anyone else but my brother and I used to mess around. We sucked each other off. So I've tasted his cum and mine. It was just something we did."

"Really! And do you still do things together?"

"Not that way. As I said, my brother and I have double-teamed a few girls and even done some double swapping. Once I ate his girl's pussy after he fucked her. And he did mine. I think we were both kind of drunk at the time."

We skied that morning, broke for lunch, and skied until closing. We took quick showers in her palatial suite and then fixed margaritas. We both got a little tipsy and decided it would be better not to drive somewhere for dinner. We ate at the resort, which was certainly not a come-down.

Two hours later we were back in bed with Cathy sucking my cock. I was getting close but she pulled off and told me to fuck her. She was wet and my cock was hard. But I knew I wouldn't last long. And I didn't.

She giggled. "Damn, Bobby, you came way too soon. I was just getting started."

"Your fault. I almost came in your mouth. And then a couple of minutes in your tight pussy was all I could take."

"Well, you know what you have to do, don't you?"

She grinned and pushed my head lower. "Guess you'll just have to eat me. Cum and all."

"You devil! You give me a hard time about eating cum, then you set me up to do it again."

"Of course. It felt way too good to be a one-time thing. Get started."

Stan called the next morning. Cathy reported that he would be headed home in two days and was looking forward to some sex. I overheard Cathy ask him how come, hadn't he been getting laid. She laughed and said Bobby was filling in quite nicely for him.

"Yes, I'm sure. Yes, uh huh. Won't be a problem."

"What was that about?"

"He wanted to know, firstly, if you were good in bed. And then asked if I thought you would be up to a threesome, you, me, and him."

The next two days were delightful. I wanted to beg off ski instructor work but Cathy suggested I give her private lessons. She said Stan would pay. We had spirited sex, followed in the morning by some loving.

That evening I moved out of her suite. Stan arrived late morning the next day and Cathy skipped skiing so she could meet him at the airport. They spent the day together fucking, I assumed. Later that evening she called me to ask about getting together to ski. Stan wanted to join us and see how she had progress on the moguls.

I was very apprehensive. I had been fucking his girlfriend the last several days and he knew it. I wasn't used to guys who so expansively shared. Stan was all smiles and we shook hands. Cathy hugged me.

"Cathy tells me you are an excellent instructor and she learned a lot from you."

I assumed his comment was heavily double-entre. "We had a good time, as I think she expressed to you."

"That she did. There are times when my business necessitates travel and young girls shouldn't be alone to just watch TV. I would very much like you to join us for drinks and dinner tonight."

"Yes, I was hoping for an invitation."

With that we put on our ski equipment and headed to the lift. Stan and Cathy rode together and I followed. Stan proved to be an exceptional skier, smoother in style than me. I was more aggressive in the bumps so it evened out. I was proud of Cathy. She handled the bumps very nicely, always staying in control. She beamed as Stan profusely complimented her progress.

I was picked up in a limo at 6 PM. "George" drove, the other fellow in the front passenger seat. Stan, Cathy, and I had the spacious rear section. Very nice. A person could get very used to this. I realized as I had that thought that it also applied to Cathy.

We had reservations at Nadia's, "the" place in town. The maître d was effusive in greeting Stan. I didn't think he was known in town but obviously someone had passed the word. As might be expected, our service was excellent and the food superb.

"You can come back to our place, can't you?" Stan asked as we re-entered the limo. I nodded. Cathy beamed at me. Oh, my, what a good time was coming.

And it did. As we undressed, I couldn't help checking out Stan's equipment. He and I were the same size. Big. Since Stan didn't like eating pussy I was drafted to do the deed. Cathy bragged as to my expertise. Next Stan had her roll onto her tummy and he entered doggy style. I moved to a chair by the bed to watch. I had seen my brother in action but Stan's technique was a little more sophisticated.

It was obvious that they were long-time lovers. Their moves harmonized and they came simultaneously. Cathy rolled over, a satisfied smile, and Stan kissed her. "You are the best, honey. I'm glad you're back." Good strategy, I thought.

Then she looked at me with a gleam in her eye. "Bobby, come over here."

I positioned my cock near her pussy, ready to enter her sloppy hole.

"No, not yet. I told Stan what you did. You know, eating me after you fucked me. He wants to watch."

I looked at her with surprise, then at Stan. He motioned for me to proceed.

"Cathy, that was my cum in your pussy. You want me to eat you out with Stan's cum in you?"

"Sure, why not? You told me you and your brother sucked each other off. Can you believe that, Stan?"

"Cathy told me, I thought that was so erotic. I'd like to meet your brother sometime."

"Come on, Bobby. Do me. I'm sure Stan's cum tastes about like yours. Or your brother's."

Truth be known, I wanted to do it, to show off. I scooted between her legs. She held her pussy lips open, showing a small amount of creamy cum. I stuck my tongue between her lips and lapped up the juices.

"Here comes some more," she warned me as she pushed out. "Stan, is there more there?"

"Yes, a big glob."

"Get it, Bobby, lick it up."

I lapped away and then placed my mouth on her pussy, sucking out any remain juices and cum. I suddenly stopped and shoved my cock deep into her on one thrust. Cathy instantly climaxed. I fucked her hard for about ten minutes, during which time she had several small climaxes. Finally, I filled her hot pussy with a huge load of cum.

"Oh, my god, that wonderful. Did you see, Stan?

I left shortly thereafter after getting an invite for the day after tomorrow. "Tomorrow is just for us," Stan explained. I certainly understood.

The winter season was just underway and I had already had more and better sex than any other. During the next two months I had invitations to join them two or three times a week. Cathy also took several more private lessons which gave us opportunity to catch up on things.

All good things come to an end, and they did. Stan and Cathy departed. I doubted I would ever see either again but I had fabulous memories. The downside, I later realized, was that I would forever compare other girls to her. So beautiful, so young, so sexy.

Summer came and I was now assistant manager for our parents' three outfitting companies. Business was good and my brother and I had introduced some new technology. I also continued part time as a ski instructor that winter and the next. One change: my brother Jim was now working part time in ski patrol. On our days off we skied together.

Jim and I continued to perfect our ski-lift seduction technique: eight minutes to say hello, exchange names, where from? what runs are you doing? how about we do a run together? The next lift moved on: where going to school? with friends? how long here? etc.

The girls had come to have fun so they played along.

By the next summer our parents wanted to retire so they helped finance the purchase of our companies by Jim and me. We focused on management issues and no longer handled the river rafting operation.

I looked up from my desk at a young girl standing in the doorway. I was shocked. It was Cathy.

"Cathy? I can't believe it's you. What are you doing here?"

I hugged her and she hugged me. There were tears in her eyes.

"God, Bobby, it's so good to see you. I did some on-line checking and was so pleased to see that you and your brother are doing so well."

"Yes, the last eighteen months have been good. Here, come and sit down. Our parents retired and Jim and I own the companies. We have doing some modernizing and adding technology. I still do some ski instructing, but less and less. What about you? Tell me."

"Stan and I split up two months ago. He was a good guy. If it hadn't been for his legal problems we might still be together. Anyway I'm on my own now and I wanted to look you up. I was afraid you would be married with five kids."

"No, haven't met the right girl yet, at least not around here. Actually since our parents retired we have been so busy. And a bad thing about young guys like us, the local girls all have their hooks out. Some are so obvious. And besides, no one could compare with you."

"You mean as a fuck buddy?" she said with a laugh.

"Well, yeah," I said with a smile. "And also as a person, a friend. Sure, we had some really good times together. The sex was fabulous. But you have always been the same person, beautiful, smart, gracious."

"Don't forget "great personality'. That's always the worst description for a girl."

"Yeah, great personality. Hey, what are you doing for lunch?"

I was dying to find out what happened between her and Stan.

"Well, you know Stan was always involved with big deals. International stuff."

"Yeah, he obviously had money. And how many guys go around with two body guards?"

"Well, he never took me into his confidence. Said it was better if I didn't know anything, and he was right. The FBI arrested him for currency exchange violations. They questioned me and finally decided I was just some young bimbo who didn't know anything. Anyway, he's out on multi-million-dollar bail, awaiting trial. Knowing him, he will beat the rap. But he sent me on my way, said I needed to get on with life without him.

"You know you are very special to me. We only had three months but I felt a bond that I never felt before. Since then I only bedded Stan but you were never out of my mind. I am hoping that you might be able to fix me up with a job. And that we could be friends, maybe more."

NerdySex
NerdySex
787 Followers
12