Online Dating Game

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Online Dating Game: Sister vs. Brother

This story is entirely fictional. The places, characters and events depicted in this story are not meant to have any resemblance to any real places, people or events and any such similarity is purely coincidental. Before you ask me, I’ve never done internet dating. I was contemplating internet dating when my research on the subject inspired me to create this story and the characters. Please forgive any spelling or other grammatical errors, I’m not good at editing my porn writing. Thank you to Literotica for putting my story up on their site.

I enjoy teasing stories with an intense build up that helps to make the characters’ actions seem more realistic. The reader has to earn the physical aspects. Thus making the story, hopefully, more erotic. If you are looking for a quick slam, bam thank you sis story, you won’t like this tale. This story is long and detailed. If you finish the journey, let me know if you enjoyed it.

Why do people cross societal lines of behavior? That’s what interest me about this topic. Why people might cross it. Is it love or the excitement of the taboo or a perversion or loneliness or good old fashion need for sex or simply opportunity? Would you fuck your gorgeous sister if you had the chance?


It’s funny how life can hit you. Wreck you just when you think things are going well. Even when you try to be a good person and do the right thing.

My bitterness was inspired by my recent dumping by my now ex-girlfriend. I had sworn off picking up women in bars. I use to be a big time player and rarely went home without at least a couple of phone numbers from a club. Club rats were no longer my thing. So I started looking for a different kind of women, elsewhere.

I met my ex on a singles hike in the California mountains. She was a fellow lawyer and it seemed so meant to be.

Laura, my ex, was not perfect. After I slept with her on the 2nd date, I thought about dumping her because she had big butt. My ex was very attractive but sizeable asses are a huge turn off for me. I decided to overlook her imperfection.

At 37, I determined that I needed to grow up and judge women less on their physical features. Physical perfection doesn’t last anyway, I reminded myself. Laura was sweet, fun, sexy and seemed so into me that I thought she’d never hurt me. What a wussy I was.

Unlike my usual bad boy ways, I tried to treat her with class, respect and give her attention. Plus, I was too honest with her. I told her I wasn’t wealthy and couldn’t help her career.

Of course, I got dumped. I got too needy and available. And not rich enough. It was the first time I had ever been dumped. I’ve been rejected many times at clubs, coffee houses, etc. but this was first time a woman I slept with said, “Get Lost.” I’m usually the one doing that.

Karma. Pay back is a bitch.

Women want a challenge. After 10 emails and a few phone calls, I knew she wasn’t coming back. Finally, I learned getting dumped stinks. The summer in this part of CA was ending and soon it’d be winter. Just when you need a cuddle buddy most.

A month later I was walking into my parents’ house for a family dinner feeling lonely and sorry for myself. Last night, I found out through a friend that my ex was doing internet dating. It hit me like a brick. She had told me she was too busy to date anyone right now. I knew it was a lie. If a woman wants you, she will always make time in her life for you. Of course, I looked up her profile on the dating site and cursed the cunt out.

I didn’t miss her so much as I didn’t want to have to get back out there dating again. I was all dated out. I hate dating!

As I opened the door my sister, Maggie, was playing with our nieces and nephews. Maggie was gorgeous at 32. My sister looked like she was 25 with dark shoulder length hair, thin, small breast, cute butt, very femine and 5″7′ tall. Maggie worked out 3-4 days a week so she wasn’t just thin but very toned. She was wearing an off the shoulder summer dress that showed off her exquisite collar bones and shoulders. So thin, delicate and sexy. My sister looked more Irish while I looked more German.

I’m Greg, the brother btw. My older sister is named Stephanie. She’s 38 looks 28 and exactly like Maggie. Stephanie is married with 3 children.

Maggie was so my type if she wasn’t my sister. I love shoulders and collar bones like that. I wonder if my sisters had anything to do with that? No. That’s so sick.

Maggie was a nurse at a hospital. To her patients and their families she was kind and caring. She loved children and was desperate to start a family.

The only problem is…She is a total bitch. To everyone who wasn’t a child, sick child or parents of a sick child, and maybe a few fellow nurses, she treated like garbage. She thought she knew more than any of the doctors. Especially the interns. When they gave her orders she simply ignored them. She called interns the “idiots” or “007s”. My sister did ataşehir escort bayan begrudgingly follow the orders of the attendees who she consulted with when any intern gave her directions.

Worse of all, my sister, Maggie, knew she was totally hot and that every guy she met wanted to fuck her. I couldn’t wait for her to start losing her looks. Unfortunately, she still didn’t have a wrinkle and continued to be drop dead beautiful.

Put it this way. My sister was a gorgeous nurse in a hospital full of doctors yet she was still single. Bitch. Enough said.

My sister had broken up with her live in doctor boyfriend of nearly 5 years about 2 months ago. Being a divorce lawyer, I told her that people who live together before marriage have a higher rate of divorce than those who don’t. And that’s only if they get married. Which most live in couples don’t. Plus, my sister’s ex boyfriend had already been divorced. Divorced people’s 2nd marriage only has a 23% chance of working out compared to a 1st marriage which has a 57% chance of going the distance.

My sister didn’t listen to me. She never listened to anyone. Maggie was good at 3 things. Her job, being a bitch and playing guys. So when I told her if you want to get married do not live with the guy…She ignored me. When I told her 2 then 3 and then 4 years were way too long to live with someone without a ring. She ignored me.

Her ex was an egotistical surgeon. But I’ve learned that’s the kind of guy high quality women go for. Women are so clueless.

Don’t get me wrong, I’ve take advantage of this flaw in woman many times. After all I’m an egotistical attorney. I’m a good talker so I’ve talked my way into women’s panties many times. So much so that I’m still single in my 30s because I was having way too good of a time. Now when I want to settle down, I can’t find anyone who seems to be worth the effort.

We sat around the dinner table as the discussion as usual filtered to Maggie and I being still single. My sister looked at me and rolled her eyes as she quietly whispered, “Here we go again. At least you got dumped too. And You’re older.”

Being the jerk I am, “Yeah, but I can have kids at any age.” My sister shot me a vicious look. My sister slammed her fist down on my leg underneath the table. Maggie, “Jerk. I know 50 ways to kill you. And they all make it look like an accident.”

“Go for it. Just don’t tell me I have to date anymore,” I laughed. My sister reached and grabbed a fork and playfully pointed it at me. I reached over, underneath the table and grabbed her leg. My hand was slightly above her knee, just at the edge of her dress. I began slowly stroking the top of her leg. I meant to only touch her for a second but the warmth of her flesh entranced me.

I slowly moved my hand back forth over the side and top of her leg.

Maggie quietly, “I know what you mean. I can’t bring myself to date again. My trust in men is shot! 5 years of promises and nothing to show for it. But years lost. I could have had a ton of guys that would have married me. You were right about living with him.”

My hand stopped and I patted her leg gently and then placed my hand on her knee. My fingers caressed her naked skin slightly above her knee at the beginning of her inner thigh.

I smiled, “I hate being so smart. Don’t feel bad. I knew Laura was about to dump me. I was being too nice. So what did I do. But try to be nicer. Dumb.”

My fingers continued to massage her inner thigh as my hand stood still. Then my hand moved up a little further. It seemed like I was no longer controlling it. I barely grazed her dress and then stopped. This time my fingers and most of my hand were on my sister’s inner thigh.

Maggie, “Nice guys. Nice people finish last. I took so much shit from Doctor dickless that I’d never tolerate from anyone else. I thought we were going to have a family together. Instead, I get dumped and he’s dating some 24 year old, dumb as rocks, intern. Lovely. I’m 32 now. I’m old.”

My hand continued rub my sister’s inner thigh up and down. Continuously caressing, stroking her soft flesh. At times pushing with my fingers. At others with my palm and finally lightly touching her with only my finger tips.

I laughed, “You’re not old. You look like you’re 25. Plus, that’d make me old. And I’m definitely not old.”

My hand touched the hem of her dress and stopped. But this time I angled my hand so that it moved from partly on the top of her leg to her inner thigh. My hand moved forward as the tips and then my complete digits slipped under my sister’s hem. The knuckles of the back of my hand grazed Maggie’s dress fabric. My fingers were completely under her dress but I stopped short of moving the rest of my hand, my palm, underneath my sister’s dress.

I softly rubbed her thigh. Back and forth my fingers playing with her yield, warm flesh. The whole time looking at my sister talking to me. Watching out so that no one else noticed. My mom and dad and my other escort kadıköy sister would kill me for doing this. But it felt so good to be touching a woman. My caressing, massaging my sister’s inner thigh didn’t even feel sexual until…

“Like you said guys have it easier,” Maggie added. Then she stopped talking. My sister looked down at the table as I massaged her inner thigh. My sister didn’t look back. My sister closed her eyes. She sat there for several seconds with her eyes closed as I continued to rub her thigh under her dress.

Back and forth. Up and down feeling her intimate flesh that led to her genitals. I stared at her the whole time. Suddenly, I was terrified at what I was doing.

Then my sister took a breath and opened her eyes. Her hand moved from the table downward. My sister grabbed my wrist tightly. My hand froze in place on her thigh. My sister has strong hands. I used to tease her calling them man hands. She pulled my hand out from under her dress as my fingers lightly scrapped her inner thigh and then her leg on their way out from under her dress. My sister placed my hands on my own leg and then let go.

My sister looked around the dinning room table to check if anyone had observed her bad brother. My sister shook her head. Wanting to distract her, I said as normally as I could, “Women have it so much easier. A girl like you can get anyone you want.” I was afraid she was about to tell everyone at the table that I was rubbing her leg. Her inner thigh.

“Women can get laid anytime they want. They can’t find a real relationship that easily. You can’t trust guys. They lie so much about what they really want,” Maggie explained. My heart was beating like a drum. I wasn’t sure if there was a subtext to her comments or not. But I knew what she said was true. I laughed as the tension released.

“Please, cry me a river. You’ve got it so easy. You select. If I want sex, I have to go out there and work for it,” I replied.

“Yes, but a relationship is different,” Maggie whined about the hardship of a gorgeous women.

“Problem is that women want smooth talk and guys who treat them badly. Once you are no longer a challenge. Once they know they’ve got you. See ya. Especially women in their 30s. There is a reason they’re still single,” I told bitterly.

“Not true of all women in their 30s. But some. I get hit on all the time. It’s such a hassle. They’re all so lame. How can you judge which guy is not just after a quick roll in the sack. It’s not easy. I’ve made bad decisions,” Maggie shockingly admitted. “I was a sex toy for the doctor. Arm candy. That’s all. I realize that now. I thought it was more. He was busy with playing God so that’s all he really wanted.”

I frowned, “Well, I need to find some arm candy that appreciates being treated right. I just don’t have the energy to be a jerk anymore.”

My mom interrupted are soft spoken discussion, “Have either of you tried internet dating?”

Maggie dignified, “Mom, that’s so tacky.”

Our mom continued, “There’s no stigma anymore. Doctor Tom recommends it on his tv show. You just have to make sure to meet in a public place. It gives you a chance to meet people who you normally wouldn’t encounter.”

Maggie and I in unison, “I’m not doing internet dating.”

After dinner, I walked over and sat next to Maggie who was holding one of my nieces in her arms. Maggie looked so picture perfect. A mother and her child. But that wasn’t the case here. She was an Aunt who seemed to be longing to be a mom. Her job must really torment her. I knew Maggie wanted to be a mother more than anything in the world.

I softly touched my nephew’s head back. I looked up at Maggie who was smiling contentedly but longingly. I softly told her about my ex, “Laura is doing internet dating. A friend told me. I checked out her profile. Active within 24 hours. Lying bitch.” I paused for a minute and then looked at Maggie, “I’m thinking of doing it.”

“Internet dating? Are you serious? Are things that bad?” Maggie asked.

“I could go to bars but that’s gotten me nowhere. I’m good at picking up women but the wrong kind. Plus, I’m getting old,” I smiled bitterly.

“You’re only in your mid 30s. Internet dating is too weird,” Maggie reasoned.

“We should do it together,” I replied.

“What?” Maggie voiced.

“Internet dating. We should both sign up. Whoever finds their soul mate first wins! Come on, it’ll be fun. At worse we’ll get a couple of laughs. It’s not like if we meet someone in real life we can’t go out with them. There is nothing to lose,” I explained.

“For you. I’m worried about getting raped and killed,” Maggie admonished. Even her own brother was caressing her thigh at the dinner table what would a normal guy do to get her naked!

“Like mom said, meet in a public place and it’ll be fine. Starbucks, Barnes and Noble. Restaurant. Etc.,” I tried to convince her. For some reason if Maggie did internet dating, it would be less weird than me doing bostancı escort it alone.

“Alright. Why not? I have no one to go out with these days anyway. All my friends are married,” Maggie decided.

“Same here. That’s why you don’t want to be the last person in your group single,” I knew. “I’ll swing by your place Thursday and we can put together our profiles. For moral support.”

“Sounds good,” Maggie relented. The baby stirred in her arms and she patted his back softly. “If I get killed, I’m coming back to haunt you.”

I reached over because I knew I could. After all she couldn’t drop the baby. Plus I felt that it would make it less weird about before, if I touched her now. I placed my hand on her knee with my fingers on her inner thigh. I squeezed gently and then let go. Immediately, I started to stand. My sister’s eyes flashed for a second but then followed me up.

“Don’t be so melodramatic. You’ll be fine. If anything does happen, I promise to cry at your funeral.” I thought to myself, “God, my sister has nice legs.”


I brought my laptop over to Maggie’s new town house. Maggie answered the door dressed in a pair of white shorts and a white t-shirt. I could tell from her perky nipples and wet hair she had just gotten out of the shower.

Maggie rushed, “I just got back from gym. I needed to take a shower.”

“Your internet beaus will be glad to know that you’re keeping in shape for them,” I teased.

Night before, I had spent about 2 plus hours writing what I considered a perfect profile. I showed it to Maggie who said she thought it was good.

I asked her if she had written anything. Maggie said she’d write her profile off the cuff.

My sister sat on the other side of the table from me. We both seemed perfectly normal but I couldn’t help but notice that she kept out of arm reach. I guess she’s had a lot of practice fighting off guys. I had promised myself to behave. Not to even touch her though I still didn’t think anything I had done was really sexual. But when I thought about her gorgeous legs and the fact that my hand had been under Maggie’s dress…I was a little embarrassed and confused.

We both logged onto the site and started filling out the questions. I had been agonizing over a screen name and finally decided on my last name plus the numbers at the end. Maggie did the same. I accidentally pressed my leg against my sister’s. I left my leg there so my calf was snuggled up against Maggie’s leg for the whole time we filled out the questions.

I was half way through when Maggie got up and went to the fridge for a bottle of water.

“Are you done?” I asked her incredulously.

“Yeah, it’s not difficult,” Maggie said lazily.

I looked at her profile. Her introduction was one short paragraph saying how she was sweet, smart, etc. And then one sentence on what she was looking for in a guy. My sister uploaded only one photo of herself. In the photo my sister looked cute but not nearly as hot as she could look. You couldn’t even tell how good a body she had. Plus, she had this Mona Lisa smile/sneer.

I thought her profile stunk. So I simply snorted and said, “Do you want to tell more about yourself? There’s not much there. Maybe, another couple of photos. Administrative Assistant. You’re a nurse.”

My sister yawned, “It’s all there. Athletic/toned. Definitely wants children. What I’m like and what I’m looking for. I don’t want guys to know I’m a nurse. I’ll tell the right guy. He won’t care. It’s good enough.”

I went back to work on my profile. It was a work of art. Heartfelt, funny and long. I answered all the extra questions in detail. My profile used up every available space. I knew that any woman that read it would instantly want to meet me.

After all I was an attorney, successful (I made sure I put my income down while my sister didn’t), attractive, borderline very attractive. Also I put up 10 photos of me. In a suit, hanging out having fun, on the beach shirt less (I have a great body).

How could a woman not want me I thought. It’s like shooting fish in a barrel.

I said, “Why don’t I swing by Sunday and we can check in on each other. Maybe get lunch.”

“I’ll cook. I love to cook for someone else. I put it in my profile,” Maggie grinned. I just hoped someone would respond to her profile. I thought to myself. There are some desperate guys out there, right?


My sister answered the door. Immediately, she busted out laughing, “41 emails. Almost all of them from losers. Don’t they read my profile and what I’m looking for section. A couple have possibilities. How did you do?”

I told her, “I haven’t checked yet. Let’s see.” I checked my profile. I thought it was a mistake. 4 messages. 2 from some huge women. 1 from a women in Russia. And 1 from some very average looking chick.

“4 messages. You got 40 messages. And I got 4,” I said nastily.

My sister started to dance around the kitchen laughing as she finished making lunch.

“That’s ridiculous. I looked at how many women had viewed my profile. 23 views. Maggie’s profile had been viewed 356 times. What the fuck???? I had my sister look up my profile and then send me an email to make sure it was working correctly. It was.

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