Oscar's 1st Time

Oscar was now 16, and he desperately wanted to lose his virginity, but how? His Aunt Steph and Grandma Diane were there all of the time, watching his behavior, and he did not yet know that they were closer to his parents than normal relatives would be. What he also did not know, however, was that his aunt had noticed his sexual development most closely of all of his family, and she really wanted to fuck her nephew, who was, after all, as well-endowed as his Dad. His 8 inch cock would be inside her, she determined, whatever the cost. 

Aunt Steph naturally preferred to have her brother's permission to fuck his son, especially since no one in the "sex group" had fucked any outsiders since her mother Diane had been initiated. This was supposed to be a "swinging circle", allowing people to swap with people they knew and trusted. However, she had defied her brother, and if necessary, in this case, she would accept whatever penalty he sought to impose. She was his slave, and she normally obeyed him, but this was worth a flogging.

She knew that Oscar, being a typical teenage virgin, was masturbating frequently. This was one way to get his attention, by "accidentally" walking in on him in the process, and taking his hard cock inside her before he could refuse her pussy. She wanted to use action, not persuasion, since it worked so well for her brother. Once it was a fait accomplis (fact accomplished), they could all deal with the results and the future. That was her plan, and so she set out to execute it. She carefully observed his behavior for a week, figuring out when he was most likely to masturbate.

One Sunday, while her brother was busy attending a Nascar race, and her sister-in-law was shopping at the mall, she quietly approached Oscar's bedroom, knowing that he was pretending to be asleep, but actually playing with himself. Sure enough, she saw through the peephole, Oscar was stroking himself to near ejaculation, and would soon cum from his own efforts. What a shame to let that semen go to waste, she thought. Now, I've got to fuck him, before he cums.

She abruptly opened the door, on the pretext of trying to awaken him, and caught him red-handed. "Oscar, you bad boy- you're going to cause a mess on your bedsheets, and I'll have to clean it. You need to put your cum somewhere, so put in me!", she announced. With that, while he sat stunned, she went over, pulled up her nightgown, dropped her panties, and straddled his youthful form, taking his cock inside her suddenly. He groaned for a second, as her body weighed a little more than his, but he was obviously starting to enjoy the new sensation of a warm pussy around his cock.

She rode him for several minutes, before his previously manipulated manhood unleashed its load, filling her cunt, and making her cum, too. That wetness on his cock got him hard again, as he realized just how wonderful a vagina felt around a penis.

"Aunt Stephanie, you just fucked me! Why? Aren't you not supposed to fuck your kin?"

"Too late, even if that were true, nephew! We have committed incest, and I want to do it again with you. You're that big!", she taunted him. 

"But Aunt Stephanie, you're my aunt- what if you get pregnant by me?", he asked, genuinely concerned.

"Well, then, we'll have just have to raise the child, won't we? Anyway, I had your Dad's baby, you know? That turned out OK!", she reminded him. 

Oscar's eyes got big, as he realized that the "artificial insemination, womb donor story" his parents, Aunt Steph, and Grandma Diane had always told him was a lie. "You mean that you had sex with dad- your brother! That wasn't artificial? There's nothing wrong with Mom's eggs?"

"Sorry, bud, but yeah, that was a necessary lie, until you were old enough to understand the truth, and now you are. Remember, we told you things like santa existing, which we later said were fibs- well, this is just another fib.", Aunt Steph informed him.

"Oh, well, then does Dad know that you want me?"

"No, dear, but he will."

"I guess Mom knows about you and Dad; are you still fucking each other?"

"Well, yes, actually. You see, your Mom, Dad, me, and your Grandma are all lovers." 

"Mom and Grandma too? Is there anyone else?"

"Well, certainly there is. All of your Dad's employees and their wives are involved with us. We all fuck each other whenever we wish. Normally, we don't fuck more than that number, though."

"Do you mean that you, Mom, Grandma, and other women fuck each other, too?"

"Yes, Oscar, we do, and it's a lot of fun."

"Wow, so they probably won't be upset with you for fucking me."

"I hope not, but I am taking that risk. I want you to have a happy experience as a teenager, and, frankly, I want to have a happy experience myself- fucking you, that is. Your cock is large, just like your Dad's. Lots of women love big dicks like yours, including me."

"So can I fuck other girls, besides you? I mean, if you are fucking around, shouldn't I?"

Stephanie laughed, and responded, "Well, naturally, Oscar, you need to try different kinds of girls, and see what you like. Women have their personal preferences, too, just like men, both as to partners, and different sex acts."

Oscar looked strangely at her, and then asked, "What other kinds of acts, Aunt? How else do you fuck, besides, sticking it in a pussy, eating it, or getting blown by a girl?"

"Those are common acts, the most common, in fact, but a lot of people like to touch breasts, spank each other, and even fuck people in the ass. The last part is especially true of gay men, but not just with them."

"Will you show me how to do these things, so I can make the girls want to fuck me?", he eagerly asked her.

"Of course, I will, Oscar- I love you, and I want you to be sexually fulfilled, and as for any girls who have the good taste to want you, well, I want them happy too. I will see if you can be a temporary member of the group, with the understanding that you will be free to fuck around once your skills have improved. When that happens, though, you will probably be given a choice of exclusion from the group, with full freedom to fuck whomever you wish, or inclusion, meaning that you will have to be faithful to the group."

"Will you be punished for being unfaithful to the group, Aunt Stephanie?" 

"That depends on how much they approve; if I am punished, however, they won't blame you, since you didn't know about it. I don't regret, though, in this special case, because you needed me, and I needed you. I will accept whatever punishment they inflict."

Then, Steph began to suck his once-virgin cock, seeing that fellatio was no big deal when you've already committed incest. "Oscar, you have a deliciously meaty cock! Fuck me again with it, before your parents or Grandma catch us!", Steph urged him, taking his cock out of her mouth. She then lay on her back, spread her legs, and invited him to get on top this time. "Come on, Oscar, take control of your wicked, incestuous aunt!", she teased him.

He eagerly took up her offer, mounting her missionary style, and pounding her forty-something pussy with his adolescent phallus. "Oh, Aunt Steph, you are pushing back against me, and getting me harder- I am loving this- you're wonderful! I want to keep fucking you all day long!"

"That will change, you know, nephew. Most guys tire of the same pussy after a while; don't worry, I won't get upset with you over that- it's the normal human behavior, especially for boys and men. For now, though, I am going to drain you as much as I can! Give me your seed, Oscar- fuck me until I go crazy!"

He ruthlessly penetrated his aunt in this 2nd, and longer, copulation of his life. She squealed repeatedly, evidently thrilled that her well-tanned new lover was giving it to her as rough as he possibly could. rough sex always appealed to Stephanie- it made her feel like a wild animal, mating with whomever asserted himself enough. She simply loved big, hunky guys like her brother and his son, especially if they had suntans and sizable manhoods. 

The feeling of her well-hung nephew's cock inside her cunt was getting her wetter than she could imagine, and about the time he was ready to cum, so do she, causing an unusually mutual orgasm. When he was done with that, she begged him to eat his cum out of her pussy, to "clean it up for your Dad's use". He could not refuse her request, since she was so horny for him, and so just plain hot! So, his first taste of pussy and semen happened simultaneously, and the mixture was incredibly delicious to him. 

"Aunt Steph, this is so tasty! I love a cum-soaked pussy!"

"Good, nephew, because I love to get a man to eat his own cum out of my sex- your Dad does it sometimes, but only as a reward when I behave myself. I guess I won't be getting that privilege from him for a while."

"Don't be so quick to assume that, Sis.", a voice suddenly spoke up.
It was Blair, and he was grinning to see his sister and his son in flagrante delicto. "Joanna and I were going to ask you, or Mom, to take his virginity, but it seems that you beat us to the punch. You know, Sis, it's only logical that Oscar become part of the group, at least for a while, and I couldn't think of a better introduction to sex than to have his aunt seduce him. You were just on the same wavelength, so I don't mind you stepping out on the group and taking some initiative. You care about my son, your nephew, and that's good, so let's just take this a little further.", he stated, as he disrobed.

Soon, he was naked, and Joanna was joining him, also in the buff, having apparently been undressed by her mother-in-law in the bathroom.
Blair grabbed Steph, turned her over, and penetrated her pussy doggie-style, while Joanna started sucking her son's cock.

"Mom, I can't believe that you're giving me a blowjob! You are fantastic!"

"Am I, son, well then just wait until I ride you, and I will!", she replied enthusiastically.

Meanwhile, Blair was hammering Stephanie's cunt with his hard member, and now Grandma Diane participated, sitting on her grandson's face, so he could taste her moist sex. She may be over 60, Blair thought, but she is still a splendid fuck! Lucky young Oscar was eating his grandmother's pussy, while having his cock sucked by his mother.

Blair was fucking Stephanie harder than ever, completely aroused by the 3-way between his wife, his son, and his Mom. Steph was enjoying the sight, too, but her main focus was on the pleasure being delivered by her brother's penis. Once Oscar was on the verge of coming into Joanna's mouth, she stopped, and, just like Steph (although she didn't know it yet), she impaled her own pussy on her son's cock. He suddenly felt the somewhat tighter warmth of his mother, who was not as a good a fuck as his aunt (due to her tendency to fuck more women than men, she was less aware of how please to a guy, but only by degrees- she was still pretty damn good), but quite excited to be fucking him, and clearly passionate about his happiness.

Stephanie tensed up a bit, and then she tightened her vaginal muscles to provoke Blair's semen to release inside her, which it did as he grunted with relief and delight. He then knelt to eat her out, just as she hoped, getting her to another climax from the feeling of his tongue and mouth pleasuring her pussy. Diane then moved over to him, and started giving him a blowjob while he ate Stephanie. This only intensified his determination to munch on Steph. 

As this was happening, Joanna came, followed by Oscar, and she sat on his face, letting him taste himself inside another woman's vagina. She was totally getting off on this particular experience, since it was almost as good to be eaten by a man as it was with a woman. 

Blair now entered Diane, and began to thrust excitedly into his mother's womb, making her aging sex the wettest it had been all day. She still had a nice pussy, even at 65, and her eagerness for his cock made her even sexier. She gladly pushed back against him, while Joanna got herself drenched by her own cum and Oscar's spit.

This orgy got them all sweaty by now, as Joanna 69'd Oscar, taking his cock back into her mouth while she rode his face. Blair came yet again, this time into his mother's cunt, while Stephanie was now rimming her mother's ass. Soon, she started rimming Joanna's, making her sister-in-law cum once more, onto Oscar's face, while this stimulated Oscar's final ejaculation of the day. The group simply lay there, in a trance due to the experience of that day, knowing that for now at least, Oscar was part of the circle, and would be involved in all kinds of sex, as long as he wished to participate.

(Should this be end, or do you want more?)