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 hereSexy, Shapely & Whore, Jeanine, #02
Joey has gay sex with his brother, Bill.
Sexy, Shapely & Whore, Jeanine, rewritten and continued from #01:
Jeanine smiled while pondering the thought of having incestuous sex with her brother.
"I don't know, mom. With me only here for the summer before returning to college to finish my master's degree, it would have to be an intensive course of sex," said Jeanine with a laugh. "If he's as clueless as he seems to be, he's probably never even kissed a woman," she said. "No doubt, he's probably never French kissed a woman and made out with one."
She laughed.
"He's probably never touched or felt a woman through her clothes while making out with her. Other than seeing women online, I doubt if he's even seen a woman in her bra and panties, topless, and/or naked woman," she said with a laugh.
Jeanine looked at her mother.
"That's something that you can do, mother, while watching his reaction to seeing you without your clothes. While pretending that you don't know that he's at home, you could dress with your bedroom door wide open. You could show him what you look like in your bra and panties. You could walk around the house topless, and/or naked and allow him to not only see you but also catch you," said Jeanine.
Audrey laughed.
"Oh, Joey," said Audrey. "I didn't know you were home. Mommy always vacuums naked when alone."
Audrey laughed.
"In the way that I've seen him lusting over you, I'm sure that he'd much rather see his twenty-four-year-old big sister in her bra and panties, topless, and naked than his fifty-year-old mother," she said.
Seemingly thinking about having illicit sex with her brother, Jeanine looked at her mother.
"Other than the ones that he receives from his brother, I'm sure he's never even had a hand job, forget about a blowjob. Never mind making love to a woman and fucking her, I'd have to teach him all that he needs to know. In the short period of my summer school break, I'd have to teach him everything about having sex with women. I'd have to catch him up on years of missed, erotic opportunities," said Joey's sister with a laugh.
While thinking about having sex with her brother, Jeanine looked at her mother with interest and curiosity.
"I don't know mom. I don't want to ruin the close relationship that I have with my brother with sex," said Joey's sister.
# # #
Jeanine looked at her mother again while pondering the thought of seducing her brother for forbidden sex. She imagined how she'd go about seducing him. She envisioned teasing him by flashing him. She visualized showing her brother all that he shouldn't see of his sister.
"Do you really think that would help him if I did that for him and had sex with him? Or would that make matters worse with his sister soliciting him for sex? Moreover, would he want me to do that for him," she asked of her mother?
She paused to read her mother's reaction to her questions. When she didn't respond, she continued.
"After having had gay sex with his brother, Joey may feel more ashamed than excited to have illicit sex with his sister. He may think that he's perversely perverted to not only have had sex with his brother but also to have had sex with his sister, too," she said nodding her head at her mother. "With him emotionally sensitive, I may damage him more than help him," said Jeanine.
She paused for a moment while pondering the thought of having sex with Joey.
"Certainly, him having sex with his sister may prove to be a much bigger deal for him than it would be for me to have sex with my brother. You know me. I'd have sex with practically anyone, even daddy," she said with a dirty laugh and a shrug. "I'm as much of a whore as you are mother," she said with a dirty laugh.
Audrey laughed, too.
"I'm sure your father would love to have sex with you. You have my permission to have sex with your father anytime, as long as I can watch," she said with a laugh. "Perhaps we could have threesome sex," she suggested with a dirty laugh. "He'd love having his naked wife and daughter in bed with him."
Jeanine not only pondered the thought of having sex with her brother, Joey, but now pondered the thought of having sex with her father, as well as having threesome sex with her mother and her father, too.
"Like you have said, I've had sex with plenty of men, what's one more," she said? "As long as it will help him blossom and put him on the road to have sex with women, I can have sex with Joey."
Jeanine laughed and shrugged
"Especially after having had a few drinks, you know me, mother, I'd have sex with anyone," she said with another laugh. "If I'm having sex with my mother, and considering having threesome sex with my father, I definitely could have sex with my brother," she said laughing again.
# # #
Audrey smiled at her daughter.
"There's no one who knows as much about women, sex, and dating than you," said her mother. "You would be the perfect teacher for him. In the way that he looks at you, he's always staring at you while undressing you with his eyes. He's as sexually attracted to his big sister as I'm attracted to my beautiful daughter," said Audrey with a laugh. "It wouldn't be hard for you to seduce him."
Jeanine nodded her head in agreement.
"You're a great teacher. Besides, as you said, you're as big of a whore as I am," said Audrey with a loud laugh. "Think of all of the cheerleaders that you've tutored, especially some of those who you've bedded," said her mother with a dirty laugh.
Jeanine smiled and nodded her head in agreement.
"You're right, mother. That's something I should consider. I've tutored all those girls with more than just cheerleading. I've helped them with dating as well as with sex," pondered Jeanine with a laugh.
She smiled at her mother.
"Let me think about it and we'll see what happens. Of course, without him suspecting me, I'd have to find the right moment to solicit him," she said with a laugh. "I need to be alone with him. I could start by flashing him to see his reaction to him seeing something that he shouldn't see and has never seen of his sexy sister. If he develops an erection, I'll take it from there," she said with a dirty laugh.
She looked at her mother and smiled.
"Even though I'm still a little horny, I'm tired," said Jeanine with a yawn. "I need to get some sleep. I'll consider taking Joey under my wing," she said. "I'll think more about it tomorrow."
Audrey kissed her daughter good night and returned to her bed before their sons returned home to find them in bed together.
# # #
Sexy, Shapely & Whore Jeanine, #02
Comforting his brother while having gay sex with him, Bill has sex with his brother, Joey.
It was another typical Friday night. I had been out drinking and trying to pick up women with my friend, Jack. As usual, not getting lucky, I came home early before midnight. My mom, dad, and sister were already asleep in their beds. I was half drunk, upset, depressed, and thoroughly pissed off at Jack.
We are running buddies and each other's wingmen, or so I thought. We're an odd couple of friends because we're so different. I'm tall and skinny, wearing thick glasses, and quiet, while Jack, on the other hand, is shorter, around 5'6, stocky, athletic, boisterous, and outgoing.
Together since we were kids, childhood friends, despite our differences, we've grown to be best friends. That is, except for when it comes to women, then we're rivals. Although compared to his skills with women, I'm not much of a threat. Pushing our friendship aside, he left me for women that he had just met and hoped to bed.
Wishing that I could be more like him, I don't understand how he continually attracted all of the women. When seeing all of the other guys who have an easy time attracting women, and with me taller, and much better looking than them, if I say so myself, their success with women made no sense to me at all. Why can't I get the attention of, at least, one woman when Jack has adoring and interested women vying for his undivided attention?
'They must have big dicks. Yeah, that must be it,' I thought. 'Because most guys that I continually see getting lucky are all assholes. None of them are very good looking,' I'd tell myself to protect my ego and to make myself feel better about never getting lucky.
Assuring myself that my solution to my failure with women was because the other men had big dicks was as ridiculous as it was untrue. When first meeting them, how would women know if the men they meet have big dicks? Maybe, they just figured that they do because they're so confident.
Yet, I knew that wasn't the case with Jack having a big dick. I've seen him in the shower before at the gym, and his dick was average, at best, about 5". I certainly wasn't going to ask him how big his dick was when erect. That would be queer. It would have to be some other reason that I had not discovered at the time why other men have such an easier time picking up women. Hell, even though I knew my prick was above average, my dick was bigger than Jack's average cock!
Like so many times before, when Jack had picked up a couple of women, I was his wingman. He always promised me that I would get lucky with one of them but I never did. On this particular night, with him selfishly greedy, both women were very attractive, big breasted, and sexy.
As he always does, he dominated the conversation. He made them laugh. He showed them a good time. Their attention was focused solely on him. As if I was in the way, Jack dismissed me as if I wasn't even there. Then, when he was leaving, he said that both of the women were going home with him.
# # #
"Sorry buddy. I'll be sure to get one for you the next time," said Jack, which is what he always said.
'Yeah, right. Asshole,' I thought. 'How many times have I heard that one before? Greedy when it comes to women, he's never shared a woman with me, or helped me pick up a woman. He's supposed to be my friend, my best friend. Yet, he's not much of a friend when it comes to women.'
Needless to say, with him always promising me that I'd be getting laid, I was once again disappointed and on my own. Yet, with the pressure off of me to be alone with a woman, too nervous to make a move on her, just as well, I wouldn't know what to do if I did manage to pick up a woman. With me clueless, I know more about aliens than I do about the opposite sex.
I'm even wearing my dad's English Leather cologne. I'm tired of being alone and lonely. I'm tired of having no one to talk to and/or to have sex with. I felt as depressed as I felt horny. I hated going home early and alone again while everyone else was having a good time with women.
I was pissed by the whole situation, and with Jack in particular. Especially since he left me to pick up their entire bar tab, again! Then, again, with me still living with my parents, unless Jack invited me to his place, or a woman invited me to her place, I had no place to take a woman for sex.
'Still, that's not fair. That's not right,' I thought to myself. 'With him growing distant, as if he's embarrassed to be seen with me, especially when it comes to women, he hasn't shown himself to be much of a friend. If he's anything, selfish and out for himself, especially when it comes to women, Jack is a fair weather friend.'
Even though it was still early, not having anywhere else to go, I went home. Not being in the best of moods, it would be a better idea to be in my own bed rather than to do something stupid, be passed out drunk somewhere on a park bench, and get arrested. Tired, frustrated, and upset, still a little drunk, as soon as I walked home, I went straight to bed.
'Why me,' I asked while feeling sorry for myself? 'Why can't I get lucky? Why can't I get a woman? Why can't I get laid? Why aren't women attracted to me? What am I doing wrong? Hell, forget about having a steady girlfriend, I've never even dated anyone. Once a virgin, always a virgin,' I thought. "I'll be a virgin until the day I die."
I continued feeling sorry for myself. I curled up under the covers and tried to sleep. Usually, and eventually, I fall asleep while dreaming about seeing my mother and/or my sister without their clothes. I dream of having sex with them.
I hoped that I'd feel better in the morning. Even though I was still quite horny when thinking about those two women that I had seen earlier with Jack, tired of playing with myself over the thoughts of my mother and sister naked while having sex with them, I was too upset to masturbate.
# # #
My name is Joseph but no one calls me Joseph. Everyone calls me Joey or sometimes, Joe. I'm 21-years-old, 6'4 tall, skinny about 150 lbs., and wear thick glasses. Considered a nerd before the word nerd was coined and had become popular to describe someone like me, unfortunately, ashamed by the fact, I'm still a virgin. While hoping that my friend, Jack, would take me under his experienced wing and help me get laid, even though he promised that he would, all talk and no action, he never did.
With us what they refer to us as Irish twins, even though we're not Irish, born 13-months apart, my brother, Bill, is 20-years-old, 6' 2" tall, and weighs around 180 lbs. He's decidedly gay, or at least bi-sexual. Because our birthdays fell during the school year, he was 2-years behind me in school, weird how that happened, even though he's only one year younger than me.
Something that I'm embarrassed and ashamed to tell women; I still live at home with my parents. With Jack having his own place, even if I got lucky, unless he invited me to his place or the woman invited me to her place, I have nowhere to take a woman for sex. Hoping that Jack would invite me to go home with him when he left, he didn't. Women don't want to date a man who is still living at home with his mommy and daddy. Not that I blame them, that's just lame.
I also have an older sister, Jeanine, she's 24-years-old. She's, 5'9 tall, very fit, and athletic. Too tall and too heavy to be a cheerleading flyer, the one that's tossed high in the air, not that she's overweight, but she's not a 90 pound, petite woman that they normally throw up in the air and catch. With Jeanine about 130 pounds, my big sister is as shapely and curvy, as she is pretty. While wishing that I could meet a woman who looked like her, indeed, Jeanine is sexy as all hell.
With them thinking that I don't know, just in the way that they look and interact with one another, I've always suspected that my sister had, or is still having sex with our mother. Unable to think of my mother and sister as incestuous, bi-sexual lesbians, with my sister and my mother very sexual women, I wouldn't be surprised if they're having threesome sex with my father, too. Only, I have a hard time thinking of my sister as a whore. She's so nice to me.
To be honest, while wishing that one or the other would have sex with me, I'd be willing to have sex with my mother and/or my sister to know what it's like to be with a woman. Something that I can't stop doing, I continually masturbate over my mother and my sister while imagining them in their bras and panties, topless, and naked. Only, in the way that I'd love to have sex with either of them or both of them, even though they may be having sex with one another, they'd never have sex with me.
# # #
A cheerleader in college during her undergraduate years, quitting cheerleading to concentrate more on her studies to earn her master's degree in technology, she's very popular. Everyone loves my big sister. I wish I had her personality and sense of humor but with me being more reserved, shy, and quiet, I find it hard to break out of my shell. I find it impossibly difficult to talk to women.
With her home for the summer, something that I wished that I had, my own apartment, she has a student apartment across from the college campus. Even though she lives with and shares the monthly expenses with three other women, other than going to dorm parties, she has someplace to take a man if she gets lucky. I'd dare say, in the way that my sister looks, and with her bi-sexual, whether with a man or with a woman, she's always getting lucky.
Blessed with our good Scandinavian genes, my father, my mother, my brother, my sister, and I, all have blonde hair and blue eyes. My brother, Bill, even though I'm a year older than him, has always been my personal tormentor, and my emotional and physical abuser. He's constantly teasing me and picking on me. Too introverted to get his mean spirited jokes, I'm sometimes clueless, and that makes him laugh at me even more.
With me shyly reserved, he's much more outgoing than me. He's as popular as my big sister is. They both have lots of friends. They are always going somewhere, and doing something with their friends.
Opposite to them, I keep to myself, and have very few friends. Most times, with me working from home coding for a software gaming company, I'd rather read, write, and/or play video games than to be around other people. Always alone, not into sports, and too fair skinned to be out in the sun, I stay in my room a lot, probably too much.
Even though he's younger, my brother, Bill, seemed to have done everything first. I knew that he had gay sex with his friends and, possibly, when searching for his preferred sexuality, even had sex with a couple of women, too. He's definitely not a virgin like me.
Yet, I don't recall ever seeing him with a woman. However, there was one comment he made when we were younger and that still disturbs me to this day. He called me a loser. I'm not a loser. I'm just different from him.
# # #
Later that night, sometime after 2 am, and long after everyone had gone to bed, I heard my bedroom door slowly open. While wishing that it was my mother or my sister ready to give me sex, my brother quietly snuck into my bedroom, crawled into my bed, and snuggled up behind me. This was something he hadn't done in a long time. Instead of kicking him out of my bed, I whispered.
"What are you doing?"
Bill lightly touched my shoulder and, teasing and tickling me, he slowly slid his hand down my back.
"I saw Jack leave with two women and leave you behind to take care of the tab again. I felt bad for you and I knew you'd be upset tonight. I thought you might need someone to talk to, or me to comfort you," he whispered. "You are my big brother after all."
Bill never passed up an opportunity to tease me, make fun of me, and/or make me the butt of his jokes. Yet, for some unknown reason, tonight with him in my bed, making me feel all gooey inside, he seemed to actually care about my feelings. Unlike him to do so, seemingly, he felt sorry for me.
With me always sad, alone, and lonely, I'm becoming a loner. I'm a self-imposed hermit preferring to be left alone in my room than to be the one ridiculed and taunted in public. Staying alone in my room is not only how I keep myself occupied but also how I protect myself from being rejected and hurt. It's not so bad. I have my work to do and video games to play.
# # #
"Joey," he said. "I know I'm not much of a consolation, especially with me always being mean to you, teasing you, and making fun of you," said Bill. "If you're okay with it, I'd like to do something for you that you may need tonight."
Spooning me, he snuggled closer in behind me. Again, with him touching me in such a thrilling way, I wish it was my mother or my sister in bed with me. I'd rather have sex with a woman than with a man. I'd much rather have sex with my mother and/or my sister than with my brother. Yet, with any port in a storm, Bill was the only one offering me sex, albeit gay sex.
Surprising me as much as he excited me, he reached around and caressed my cock through my underwear. Clearly, my brother wanted to have sex with me. Always horny, I immediately developed a big erection. As much as he seemingly wanted to have sex with me, I wanted to have sex with him, too.