Jimmy Shepherd woke up with a smile and a huge morning woody. As of the evening prior, he was no longer a virgin, thanks to his stepsister. With the rising sun filtering through partially closed blinds, Jimmy threw back the covers and admired his eighteen-year-old cock. Admittedly, it wasn't a porn star penis: he was no John Holmes. But it was nice-sized and fairly thick. At least that's what Gail had said. He beamed with joy at the thought of his stepsister's compliment.

His hand automatically gripped his tool and began slowly stroking it as he closed his eyes and imagined it was his sister's pussy once again sliding up and down its length and not his fingers.

Did she ride me just to be nice, a sympathy fuck, or was it something more? Jesus, when we were making out, she was really into it. God, I was so turned on as soon as I felt her tongue in my mouth. I thought I was going to cum right then just from kissing her. I wonder if she really likes me or if she feels sorry for me, her nerdy stepbrother? What if she really has feelings for me? My sister as my girlfriend? So what? She's not biologically related to me. She does take after her mom, especially in the boob department. I wonder if Mom has big nipples like her daughter's? Gail's tits are so wonderful–and huge, especially now that they are filled with milk.

His mind was a whirling Dervish of thoughts firing in rapid succession. As he lay there slowly jacking off and picturing his sister's milky tits, he suddenly imagined his stepmother naked and breastfeeding him. He had seen glimpses of his stepmom's tits, like when he opened the bathroom door as she was getting out of the shower, but just for a second. Her tits were big, for sure. And she filled out her clothing nicely. Her blouses strained to contain those big globes.

I wonder if Dad likes sucking on tits as much as I do? Fuck, all I can think about is sex these days. Gail's pussy was unbelievable. I bet her mom is a nice fuck, too. Dad is always touching her and slapping her butt. I wonder if she is anything like Gail in bed? Like mother like daughter?

These thoughts only heightened Jimmy's excitement, and before he knew it, he felt a familiar urging from deep within his balls. He stroked himself faster, and the image in his brain of his sister suddenly changed to his stepmother. She was riding him, her eyes closed and her big tits flopping back and forth as she moaned in pleasure. That was all it took. A spoonful of sperm formed at his piss hole, followed by several powerful bursts that arced in the air and landed on his stomach and sheets. When it was finally over, he surveyed the damage. His sheets were a mess that he tried to erase with a t-shirt he had thrown to the floor the night before.

Jesus, I must be a perv. I was jacking off to an image of my stepmom. Fuck, that was wild.

Jimmy had always liked his stepmother. After his parents divorced, he was living part-time with both his mother and his father. His mother had become dependent on prescription drugs, which led to a host of other issues and ended in divorce and rehab. She was a mess but doing better now.

Months later, his father started dating Becca, Gail's mother, and Jimmy immediately took a liking to her. Besides having a full figure, she was warm and friendly and had a cute daughter who was about his age. The two sixteen-year-olds got along well despite the typical teenage dramas. Add to the formula that Becca, Gail's mom, dressed skimpily around the house and didn't seem to care if Jimmy was none too sly about oogling her. She flirted openly with her stepson. She knew it drove him crazy, and she loved it.

Consequently, he had a crush on both his stepsister and his stepmother. Gail was cute and funny and just starting to blossom when the families united, but Becca had a figure that begged attention. And when she appeared in the kitchen in her sleepwear and thin robe the first time with her big boobs unfettered, he invariably sported an erection that he had to hide. His stepmom turned him on. He couldn't help it.

And so, like most sixteen-year-olds preoccupied with big boobs, he beat off to visions of fucking her. But now he had the real thing with her daughter...his stepsister. He really did like her, but where could this possibly go? Nobody dates their sister? Do they?

In an attempt to erase thoughts of fucking his sister, he often imagined his cock disappearing inside his stepmother. She would be lying under him, moaning his name, telling him how she liked him better than his father.

Fuck. What am I doing? I'm turning into a sex addict.

********

A week passed and Jimmy received no invitations from his sister to suckle her breasts. He wondered if he had done something wrong, but it seemed like they were on trains going in the opposite direction lately. She was seeking employment and gone most days, and evenings their parents seemed to always be around and preventing them from talking openly. Finally, Jimmy found Gail sunning alone in the backyard and tried to broach the subject. Her two piece did little to hide the swell of her milky breasts.

"Hey, Sis. What's going on? Working on your tan?"

"Oh, hi, Jimmy. Yeah. I'm so pasty, but good news–I got a job. I start tomorrow. I'm trying to make enough money to get a place of my own and move out."

Jimmy's disappointment at the news was obvious. His knitted brows said it all, despite a fake congratulations.

"Oh, that's great, I guess. Yeah, you've been busy. I've missed you."

"And I've missed you. My boobs are sore and need some relief, but I haven't been able to find time alone with you. Mom or Dad seem to be hanging around all the time. If I had my own place, it wouldn't be a problem. But then, I'll probably be dried up by then. I do appreciate your help."

"Any time, Gail. I enjoy helping you out."

Jimmy's shorts began to swell at the thought of his lips wrapped around his sister's swollen nipples. He tried not to stare at the cleavage that commanded his attention.

"In the meantime, Bro, we'll just have to make do. For now, I guess I'll use a breast pump. But be ready if we get a chance to be alone. I'd rather have you than a pump."

A smile erupted on Jimmy's face when he heard that. He couldn't wait to help out his sister.

**********

"Gary, have you noticed anything funny about Jimmy lately?" Becca, Jimmy's stepmom, took a sip of her usual pre-dinner glass of wine. Her serious expression made her husband look twice.

"Hmmm? Jimmy? He seems pretty normal to me for a typical, horny eighteen-year-old. What do you mean? How is he behaving?"

"I'm not sure. He's just different. Both he and Gail seem secretive these days. Ever since Gail started job hunting, Jimmy has been moping around the house. But yesterday I'm pretty sure I heard him jacking off in his bedroom. His headboard was banging against the wall, and he was moaning something out loud. I couldn't understand what he was saying so when I knocked on his door, it got very quiet. Later, when I did the laundry, I found a pair of my panties with what looked like a huge cum stain. It wasn't from you. I never wear panties around you. You always take them off of me."

"He's probably like me when I was that age. I was jacking off all the time, too. I wouldn't worry about it. He's always staring at your boobs, by the way. I think he's in love with his stepmom, the little perv, hence the panties."

"Yeah, he does seem to pay a lot of attention to my chest. But then so do most men. Maybe I should have these puppies cut down to a reasonable size. They're starting to droop more."

"Don't even think that way. I love your tits. If you've got it, flaunt it."

That little conversation gave Becca an idea. She loved to tease, and she didn't have to look very far for a victim. Jimmy would pay a price for stealing her underwear. She felt a dampness forming at the thought of it.

^^^^^^^^

With Gail's new job, she was gone all day long, and Jimmy had little opportunity to talk with his stepsister, let alone nurse those milky boobs. He spent much of the day hanging out with friends, or, when home, locked in his room playing video games. He was doing that when he heard a knock on the door.

"Jimmy, it's me...Becca. Can I come in?"

"Sure. The door's not locked. Come in, Becca."

His stepmother entered, and Jimmy almost swallowed his tongue. She was wearing a thin robe with nothing underneath as far as he could tell. Her breasts swayed and jiggled enticingly with each step. She was holding a jar of something in her hand.

"Sorry to bother you, Honey. I have a special favor to ask. I tweaked my back lifting a heavy box, and I can barely walk. Would you be willing to rub some "Icee-Hot" on my back? It's supposed to help things like this."

"Um, sure. I guess." Jimmy's penis immediately began to swell in his nylon running shorts, and he squirmed to hide it.

"How about if I lie on your bed and you can rub some of this on me. It's my lower back, but my shoulders are sore too. Maybe some lotion for that area. There's a bottle of lotion in the bathroom on the vanity. Why don't you grab it and I'll get comfortable on your messy bed?"

As Jimmy left to retrieve the lotion, Becca stretched out on her stomach after first slipping out of the silky robe and adjusting it so it covered her ass. When he returned with the ointment, he did a double-take. His voluptuous stepmom was all but naked on his bed. Her large breasts were flattened underneath her and protruded from the sides of her bare rib cage.

He sat on the bed next to her naked form.

"Tell me where it hurts."

"Start with the 'Icee-Hot just above my rear end. You might have to adjust my robe so you don't get any of that stuff on it. It's an expensive robe, and I don't want to stain it, if possible."

Jimmy removed the lid and, with two fingers, scooped a dab of the gooey lubricant. He rubbed it around her spine in circles, admiring how soft and smooth her skin was.

"Mmmm, yes. And a little lower and to the sides of my rear end. That's where it really hurts."

Jimmy adjusted the robe, and now the crack of her ass came into view. He could see a fine layer of fuzzy blonde hairs on her rear, almost like peach fuzz. He couldn't believe it. He was actually massaging his mother's ass, or at least close to it.

"Honey, thank you for helping me out. That feels wonderful. You have strong hands, like your dad. He says you two are alike in many ways. Is that true?"

"Uh, sure, I guess." Jimmy desperately wanted to slide that robe off to the side and massage those creamy thighs...and more.

"Go ahead and use the lotion to do my upper back and shoulders, if you don't mind, Sweetie. I'm so tight. You are doing a wonderful job. I owe you."

Jimmy worked the lotion into his stepmother's shoulders and back. He stared at the smooth flesh of her breasts as they protruded from each side. Occasionally his fingers inched closer to them as he worked them in large circles.

"You know, Jimmy, I found a pair of my panties with a large stain on them, and, well, let me just say that if you would like, I have some older pairs that I wouldn't mind if they disappeared. I know boys your age have needs, if you catch my drift.

Becca turned her head and looked up at Jimmy with her big blue eyes. Jimmy looked uncomfortable.

"Don't be embarrassed, Honey. I get it. I know you like my big boobs. I don't mind. I want you to be comfortable around me. You are like your dad. He's a "tit man," too."

She was half turned and Jimmy stared in amazement as her near breast was exposed and a large nipple was clearly visible. Becca realized what he was staring at and giggled.

"Oops. A nipple slip, there. Sorry. No worries, Honey. They're just boobs. In fact...."

Becca turned over and, now on her back, smiled and giggled.

"There, have a good look, mister. Are they what you thought they'd be?"

She squeezed her arms to her sides, propping her breasts back on top of her chest. Then she reached up and pinched a large nub.

"I know. I have big nipples. Honey, don't look so shocked. They are just tits. Go ahead and touch them if you want. They won't bite."

The protuberance in Jimmy's shorts was now unmistakable. He had a raging hard-on that looked angry. Jimmy tried to adjust it without being too obvious.

"I can see you are uncomfortable, Honey. I didn't mean to cause you any embarrassment, Jimmy. I just wanted to let you know that I understand how men your age are horny all the time. And it looks like you take after your father in more ways than one. Why don't you stand up and rearrange that tube in your shorts? It's making ME uncomfortable."

Jimmy stood and tried his best to rearrange his package, but with little success. Becca giggled and sat up. Suddenly and without warning, she reached over and hugged her stepson. Her large bare breasts pressed into his erection and only made it stiffer, if that were possible. She looked up at him and smiled, Jimmy stared in appreciation at her thick nipples.

How about if I help you out there, Honey? I think I know what you need."

She reached up and, grabbing his waistband in both hands, slowly lowered his shorts to the floor. The thick appendage slowly revealed itself, and then suddenly his cock sprang free. She let out a stifled giggle.

"Oh, my! You are like your father. I have just the cure for this."

And with that, Jimmy watched in amazement as his naked stepmother wrapped her fingers around his cock, kissed the tip, and then inhaled half of his penis in her mouth with her lips forming a tight seal around the thick shaft.

Becca had wanted to do this for some time, but she had been able to restrain herself. Her love of sex is what sealed the deal with Jimmy's father, but George wasn't enough for her. Ever since she could remember, she craved sex. Strangers, both men and women, were occasionally the recipients of her pleasure-seeking. She had remained faithful in her marriage to Jimmy's father, but the suggestion that her stepson had a crush on her drove her to distraction. After all, he was only her son by marriage. And he was handsome and muscular with that energy only found in horny teenagers. Becca's preference was young men as long as they were of legal age, and Jimmy was.

And Jimmy was now about to pass out as he incredulously watched his stepmom suck his cock with a passion of which he had not even dreamed. And Becca was a pro. She stroked and sucked him like the women he so often admired in porn trailers, but this was real life. Watching her tongue flick back and forth around the crown and then bury her lips almost to his stomach was unreal.

Before knocking on Jimmy's door, she had applied a fresh coating of bright red lipstick. He now had a red ring around his dick.

Becca occasionally stopped for air and smiled.

"In case you can't tell, I LOVE giving blowjobs, Jimmy. That's probably the reason your father proposed. Although I'm not sure he would approve of this. This is between you and me, and no one else. I hope it makes up for embarrassing you earlier. You're awfully quiet. Am I doing okay?"

"Oh, fuck, Becca. This is unbelievable. But I'm going to have to cum soon."

"Oh, Sweetie! That's the whole point. Yes, by all means, cum in my mouth. You've already salted the mine with your precum, and you taste delicious. Let it go, Baby."

And with that, Becca sealed her red, full lips tightly around the shaft and redoubled her efforts. Her hand blazed with short, quick strokes, and she applied suction that would have made a Hoover proud. Her breasts jiggled with each stroke.

That was all it took.

Jimmy let out a guttural grunt and closed his eyes as a river of sperm raced from his balls to his stepmother's waiting mouth. She gagged at first from the sheer volume of ejaculate entering her mouth, but swallowed most of it and caught her breath. As she held his cock away from her mouth, he pumped several spurts that hit her face. By the time Jimmy was spent, her lips, nose, and forehead were striped with cum. One eye was sealed with white goo.

"Wow, Honey. That was quite a load. I take it you enjoyed your stepmother fellating you. I bet you never imagined anything like this. I don't think I've ever had my face covered in so much cum. And that is only because I couldn't swallow it all. The power of youth!"

Becca reached over to Jimmy's nightstand and grabbed several tissues. She gingerly wiped the cum from her face, occasionally licking a gooey finger in the process.

"Remember, this is our secret, Sweetie. If you can keep it that way, we can do it again. I certainly enjoyed it, and by the looks of it, you did as well."

She stood and kissed her stepson with a motherly peck on...