Family Business & Sexual Adventures

"Baby, we getting together Saturday?" Jim asked his girlfriend Jan.

"Sure. You got something in mind?"

"Well, my brother has his eighteenth birthday. You know, he's kind of shy, not like me."

"That's for sure. And ...?"

"You like him don't you?"

"Yeah, he's even better looking than you," she said with a smirk. "Of course, you're both studs. But he is rather shy."

"Yeah, well, he's only eighteen but ready to officially grow up. You get what I mean?"

"You mean he's a virgin? Never had any pussy?"

"Yeah, that's what I mean. Think you would like to do something about it?"

"Come on, Jim. Spell it out. You want me to fuck your baby brother? Sure, I'll do it. Will be fun. Does he know?"

"Nope, it will be a surprise. A big surprise, no doubt."

"Yeah, yeah. You know, I really love your big cock. Best part about you. Did your brother inherit the same attributes from your dad?"

"I think you will be pleasantly surprised. He and I are the same size. Your challenge will be to show him how to use it."

"How come you know so much about his cock?"

"Jan, we've been brothers for a long time. Plenty of times we have seen each other. So will you do it?"

"Yeah, you bet."

****

"Hey, little brother. How are we going to celebrate your birthday?" my brother Jim asked me.

"I don't know. Go out for pizza and beer? Maybe you have a better idea?"

"Well, you only turn eighteen once. Saturday you are legal."

"What do you mean by that? I can't get a drink in a bar for three more years," I responded with a frown. Three years is a long time.

"Dummy, I mean sex. You know, girls, pussy, fucking."

"Yeah, well I haven't had any yet, legal or not, and having a birthday isn't going to magically change that. How old were you when you had your first pussy? No, don't tell me, I know. You did enough bragging. Sixteen, weren't you?"

"Yeah! But left up to my own devices, it would have been much later. Could I help that a sexy coed had the hots for me? Well, anyway I thought we should do something special for your big day. How about you invite some of your pals over, I'll spring for the pizza and beer. Any girls you want to come?"

"Yeah, Mary and Jean would be fun. And maybe some of the guys will bring a date. Good idea."

Really bad timing. Most everyone I knew was tied up, family stuff, tickets to the game, whatever. To hell with it. Jim and I will just drink some beer together. He is my brother and best friend, one year older.

My birthday arrived. "OK, Bobby, I'm headed out for the beer," Jim yelled at me. "Here's twenty for the pizza. Should be coming in about fifteen minutes."

The pizza and Jim arrived at the same time. "Look who wanted to come celebrate your birthday," he announced. His sometimes girlfriend, Jan, followed him through the door.

"Hi, Bob, big day, huh?" She kissed me on the lips. "Oh, the pizza smells good, I'm so hungry."

Jan positioned herself on the sofa between us as we watched the game and consumed the pizza and beer.

"This is fun. I'm glad Jim asked me to join in. Two handsome guys and one girl, my kind of odds."

I got up to get more beer from the refrigerator. Jan came up behind me and grabbed me by the waist. "Mm, you smell good, Bob," she whispered in my ear. "Oh, and what tight abs you have," as she reached around with her hands, pressing against my back. "You and your brother are such studs. So good looking and athletic. You know, I like shy guys, plus of course your brother. He's definitely not shy," she said with a giggle.

I turned around with a beer in each hand. She cupped my face with her hands and kissed me hard on the lips. I pulled back with surprise but she pulled my head towards her, mashing our lips together.

"Damn, Jim, your brother needs some lessons in how to kiss," she said with a laugh.

"Yeah, I think he needs lessons," Jim said from the other room.

I was still standing by the refrigerator, beers in hand. I figured Jim was going to be pissed at his girlfriend.

"Bob, your brother says that I can be your teacher. You want some lessons?"

I looked from him to Jan and didn't know what to say. What was going on?

"Speak up little brother, my girlfriend wants to make this a very special day for you."

Jim had a big grin on his face. Jan again cupped my face in her hands, kissing me gently. "Come with me," as she took my hand and led me to my bedroom. I looked back at Jim, who nodded and motioned me to get along.

God, is she going to seduce me? Did my brother set me up with his girlfriend?

"Jim said I will be your first. Is that right?' she said as she started unbuttoning her top.

Yes!

"Ah, yes. I've never done anything with a girl except kiss. Well, maybe a couple of blow-jobs." Did she intend for us to just play around some or maybe even fuck? The idea excited me but also made me very apprehensive. What did I know about fucking? This could be embarrassing.

"Sit on the bed and watch, honey." She removed her top and bra. "Do you like?"

I was at a loss for words. My first real breasts and tits! And they were beautiful. She moved closer to me and took my hands, placing one on each breast.

"Well?"

"They are beautiful, Jan. So soft. Perfect."

"Feel them, Bob. Squeeze a little, not too hard. Now use your fingers to feel the nipples. Good."

I massaged her breasts for short while and then she stepped away, unzipping her jeans and taking her shoes off. I will always remember the color of her panties, pink. She turned to show me her backside, bending over so I could see the gap between her legs.

"Would you like to take off my panties, Bob? Come over here and kneel down. Take them off."

I reached at her hips and slid them down her legs. I was face to face with a beautiful pussy!

"Stand up and take your clothes off. I want to see your cock."

I was proud of my cock. Growing up I knew it was bigger than most. I had heard Jan brag about my brother's cock. Mine was the same size.

"Damn, guy, you may only be eighteen but that's a real man-size tool you got. Looks to me about the same as your brother's. And he's the biggest I ever had. This is going to be fun. Now sit on the edge of the bed, I want to suck you."

She knelt in front of me and took my cock into her mouth. It wasn't my first blowjob but she was the best. I lasted only a few minutes before blasting a load into her mouth.

"I hope you can recover as fast as your brother. Let's get on the bed."

We lay side by side. Jan was fondling my now limp cock.

"Play with my breasts. Yeah, that feels good. We'll get this beautiful cock going soon. You know, your brother asked me to do this but he didn't have to ask twice. You are so handsome, if Jim wasn't my boyfriend I would have seduced you long before now, legal or not. I love being your first fuck."

A few minutes later my cock was hard. Jan pulled it to her pussy and rubbed the head up and down the slit. She continued doing this for at least a couple of minutes. Then she put the head at her pussy hole. "Push in, but just a little." My cock head disappeared between her lips.

"Now back out. Now push in, just a little. Back and forth. Yes, like that. Good, really good. You don't want to just shove it in. We girls like our men to go slow.

"Ok, now go a little deeper each time. Yes. You about half way?"

I looked down. I was really doing it! My cock was half way in her tight pussy.

"Now let me feel your full length but don't shove. Go slowly. Oh, god, that feels good. What a great cock you have."

Instinct took over and I started a rhythmic thrusting, keeping it slower than I wanted but trying to follow her directions.

"OK, honey, I'm getting close and I expect you are too."

"Uh, huh. Real close."

"Speed up. Fuck me. Fuck me hard."

I doubled my tempo using almost the full length of my cock. My cock head was becoming super sensitive and every thrust added to the intense feeling. I pushed hard into her pussy and stayed deep as my cock pulsed, filling her tunnel.

"Oh, baby, I can feel you filling me up. Oh, damn. Oh, fuck."

She grabbed my ass and pulled me to her, keeping me embedded in her hot pussy. I felt a hot warmth surround my cock as she came. A minute later she released me and we rolled on our sides, panting.

"Honey, I really didn't expect much from you, first time and all. Other guys would have shot their wad way before I would be ready. You did great. Fabulous. You are going to have many happy girlfriends."

She yelled out to my brother: "Come on in here, Jim. I want your cock too."

He joined us on my bed. "Well, how did my little brother do for his first time?"

"Like a champ," she responded, giving me a big smile. "I sucked his cock and then we fucked. He made me come! And you were right, his cock is just as big as yours. He did great but we will need to do lots more practicing. If that's all right with you?"

"Sure, just so long as I get my share of your pussy."

"You will, starting now. Get down there and clean it up. Your little brother pumped a big load in me."

Jim had a puzzled look on his face. "You want me to eat your pussy full of my brother's cum? Why would I ever want to do that?"

"Well, because I asked you and then you get to fuck me. You've never had sloppy seconds, have you? Come on, Jim. It can't hurt. You've tasted your own cum before."

Jim looked at me. "A couple of months ago after we fucked Jan pushed my head down to her crotch. She spread her pussy lips to show some cum starting to leak out. After much persuasion I ate her creampie. I was drunk. Now she wants me to do it all the time."

"Bob, he did such a good job and afterwards he was ready to fuck me again. Come on, Jim, get your tongue into my pussy. Your brother's cum probably tastes just like yours."

Having protested sufficiently, my brother scooted between her legs and licked.

"Doing a great job, Jim. Keep going, make me cum."

Jim reached over and put my hand on his half-hard cock. I rubbed and stroked it to full hardness and then leaned over and licked the head. Jim moaned as I took more into my mouth.

"God, what are you doing, Bob? Oh, god, that is so bad. You're sucking his cock!"

She pulled Jim's head into her crotch, mashing his mouth to her pussy and bucked against him three or four times, then explosively climaxed.

I continued to suck on my brother's cock until he pulled away from her pussy. He turned Jan over onto her tummy and shoved in his hard cock, bottoming out in one thrust. Jan grunted with each thrust, pushing back against him.

"Oh, baby, oh baby. So good. Oh, I like fucking you. Go deep. Give me all of that huge cock. Fuck me hard."

He did. I watched as his hard cock thrust into her pussy like I had just done. A foamy fluid coated his cock and oozed past her pussy lips. They were swollen and reddish compared with when we started. I assumed, correctly, these were all signs that she was getting turned on and might climax soon. A minute later Jim pulled his glistening cock out of a well-satisfied pussy.

Jan went to the bathroom; Jim and I dressed and went into the living room.

"Well, that was certainly an experience," she exclaimed as she returned.

"Definitely the most exciting sex I have ever had. I got to take your cherry, Bob. And, Jim, I loved when you ate your brother's cum from my pussy," she added as she looked at Jim with a big smile. "That was a real turn-on. But neither could compare with the shock of seeing Bob suck your cock while you were eating me. Did you know he was going to do that?"

"No, it was just spontaneous. I wanted to fuck you as soon as I finished eating you but my cock wasn't hard. I put his hand on it to get it going."

"Bob, you didn't hesitate to take his cock, almost like it was something you had done before. Had you?"

Jim and I looked at each other, then Jim finally spoke. "Yes he has and so have I."

"Oh, I need to hear this. Go on."

We looked again at each other and Jim nodded his head. "Growing up, my brother and I shared a bedroom. Separate beds. Neither of us had done any dating yet, no pussy. But the hormones were making us horny. Anyway we started playing with each other, which quickly led to sucking cock. We did it lots back then."

"God, what family secrets! I must admit, after getting over the shock of seeing your cock in Bob's mouth, it really turned me on. I came immediately, you probably noticed. Well, growing up is a time for experimentation. But I had absolutely no idea you guys would be that adventurous. Did you like doing it?"

"Of course," I finally spoke up. "It felt good and much better than jacking off like I did all the time."

"You're the only one who knows, Jan," Jim added. "Please don't say anything to anyone. People would easily get the wrong idea. You know how much I like your pussy. And your blowjobs are exquisite. And my brother did a good job of fucking you, considering it was his first time, right?"

"Yeah, I get it. And I have my own secrets. I had a really good girlfriend and we did things together. It was fun. She's since moved away or I would suggest she join us. And there was another girl, but I've lost touch with her since I moved."

"Too bad. You've been here about a year, Jan? Where did you live previously?"

"San Antonio. You guys really want to hear about me?"

"Sure, why not?" We were very curious.

"Well, I had a boyfriend and going hot and heavy. I was young and stupid, he was twenty-five and very sophisticated. Or so I thought. Anyway when I turned eighteen he brought over a friend and they both had me. I only did it because he wanted me to. They both fucked me twice and my pussy was dripping. Larry, that was my boyfriend, took some pictures of me and my gaping pussy. He said he wanted to show me off to his friends.

"He did more than show me off. Most weekends he would invite several over. He wanted me to dress really sexy. I didn't have much so he bought me new underwear and cover-ups. All rather revealing, of course.

"I would serve them beers and snacks while they watched a football game. One or two stayed after the game and that's when the fun would begin. Larry would have me suck their cocks. That's how I got so good at it, Jim.

"Then they would fuck me. Larry would be last, calling me his slut. He would take pictures and tell me he would spread them around if I didn't cooperate. So I did. I would have anyway since I liked the sex."

"Some of the guys were very good fucks. Some just ok and a few were simply terrible. You know, the stick-it-in-and-cum type. I figured if Larry wanted me to fuck, I wanted to at least enjoy it. So I made him drop the duds from the invitee list. Then there were just a few guys plus Larry who were good at turning me on. My pussy was filled with cocks and I liked it.

A couple of the guys brought their girlfriends, the two girls I mentioned. The guys encouraged us to eat each other's pussies, usually after they filled us with cum. The three of us became the center of attraction at these gatherings.

"Anyway, our parties continued for about six months. Then suddenly Larry disappeared. I heard roundabout that he had some problem with the cops. The parties stopped without him but I still got calls from some of the guys wanting to hook up. The two girls and I continued to have fun together but even that became boring without some good cock.

"I decided to get away, to start over. My reputation wasn't good, as you can imagine. I moved up here, started using my middle name, Jan, and soon met you guys.

"Jim, I was afraid to tell you all this. I was a slut, just like he said. But I've grown up a lot in the last two years. I've left all that behind."

Jim and I stumbled over each other to tell her it was alright. "And besides, Jan, now I know why you're so good in bed. How many different guys?"

"God, I don't know. Maybe thirty or more. Many just once, a few were regulars. I was nineteen and well-fucked."

"Well, it sure didn't hurt your pussy. You're the tightest I've ever had. Did you also do lots of cock sucking?"

"You really want all the details, don't you? Yes, I sucked lots of cock. Even more than I fucked. Even a couple of black guys. And before you ask, yes, they had big cocks. About like yours. And I started taking on two guys at once, sucking and fucking. And since you didn't ask, no, I didn't do anal. No one seemed to want it and I didn't volunteer."

"Would you have?"

"Yeah, I'm sure, provided the guy's cock wasn't too big. You two would tear me up, if that's what you are thinking."

"I've never been one for anal," Jim responded. "What about the girls? Did you like eating pussy?"

"Very much so. Girls know just how to do it. Most of the time our pussies were full of cum so the taste was a combination of girl juice and cum. Now that I think of it, it was just like what you just did, Jim, eating me out after your brother fucked me."

"Yeah, that was pretty adventurous for Bobby's first time, wasn't it? He's no longer cherry but one good romp doesn't make him an expert. It took even me weeks of concerted practice to be the stud you see before you."

"In your dreams. But since you apparently don't mind me shifting my amorous interest to your brother, that's what I will do. Assuming you want me to," she looked at me.

"I will be a most willing student," I quickly accepted. "When is the next lesson?"

"We only have six weeks before you head off to college. I suggest at least twice-a-week study sessions combined with lab work. Starting tomorrow?"

The remainder of the summer flew by. At least twice a week I bedded Jan, each time learning more about the female body and sexual clues. She showed me most of the reasonable sexual positions. My favorite was doggy style. She loved being on top. That was ok with me too.

The third time we were together Jan wanted me to eat her pussy after we fucked. I had actually expected her to ask before then. I lapped away, sucking all my cum from her stretched pussy. I was plenty familiar with the taste of cum so that didn't faze me a bit. And it seemed so adventurous, so deviant. Jan cautioned me that many girls would likely find it too weird and be turned off. Others, the more exciting ones, would love it.

Our parents are fairly well off, having some property and condos. They also own a river rafting/outfitting company in mid-state. Jim and I work there each summer. We enjoy the outdoors. Our dad taught us about business, finances, and how to treat customers. We made decent summer money and buffed up with all the exercise.

I started university that fall; Jim was a sophomore.

Fresh from my expertise gained with Jim's girlfriend I looked forward to school. My friends regaled me with stories of hot freshmen girls ready to spread their legs. I discounted 90% of the stories but figured there must be some truth to it. Jim confirmed that with the right approach plenty of pussy was to be had. He was a master at small talk and closing the deal.

My first success was Janice, a girl I had in English 1. If truth be known, she was the one who was the aggressor. But I rather quickly got the score. We went out twice, the third time I took her back to our condo. She seemed rather forward but I was surprised to discover that she was very inexperienced. Only one boyfriend who had fucked her a few times before they broke up.

I quickly downplayed what experience I did have and we got along beautifully. She was a nice girl and we dated on and off through the school year. She hoped to reconnect with her boyfriend after school ended. I had my doubts.

Jim was still the go-to guy for hustling girls but now I teamed up with him. He said that was actually an advantage since girls tended to go in pairs.

We double-dated a number of times. Most of his dates were his age or a bit older. That meant most of my dates were a year or two older than me. Although I was initially nervous I quickly understood the advantage. These girls had experience and were lots of fun.