C.E.O. Finds Her Homeless Brother

"Dory, is that you?"

My ears perked up. Who would know me as Dory? I ditched that name as soon as I ran away from the orphanage when I was fifteen, some nine years ago. Being called that name always got me in a funk. Man I hated that orphanage. Mom and Dad died when I was nine, forcing me to spend the next six years or so at that orphanage. Me and...

"Tam? Is that really you?"

I was staring at a small limousine. Poking out of the back door was the finest female leg I ever saw. The high heel shoe worn on said leg screamed a tiger in both the bedroom and boardroom.

"Oh Dory, I have searched years for you." With that, I was tackled by who had to be my sister Tammy, who was dressed for success. Her brunette tresses flowed from her. She was wearing a killer business suit and skirt that did nothing to hide her figure, and with her high heels perfectly established her as an alpha female. Myself? I was dressed in street rags. "Oh Dory, what has happened to you? Never mind; big sister is here for you." Her limo driver looked on as she helped me stumble into her limo.

As we pulled away, I could not help but wonder what happened to Tam since last we saw each other some twelve years ago. "Tam, I was told you were adopted a week after it occurred; what happened?"

Tam sighed. "Those orphanage bastards got an offer they couldn't refuse. Some rich guy decided he wanted to 'adopt' a seventeen year old for a daughter so he could have a 'daughter with benefits' when she turned eighteen. I was the 'lucky' girl." Then she grinned. "But it worked out well; I played him like a Stradivarius once I turned eighteen. Some of those girls at the orphanage had already been around, and I had learned a lot from them. A WAY lot."

"So what happened to your new 'daddy'?"

"Heh, old man died of a heart attack five years ago when we celebrated my college graduation. He 'came' and went at the same time." She gave an evil smile. "People started to say that I have a 'killer pussy'. I just think of how Richard Pryor once said that was recycling."

"Who's Richard Pryor?"

"Wow, you have been deprived. Never mind, sister is going to take care of you. Starting," she whiffed in mild disgust, "with a bath."

As she said that, we pulled up at a luxury hotel. Her driver opened her door, from which we both got out. I was looked on with contempt by both the doorman and those guests inside the lobby as my sister took me by the collar and guided me inside the hotel and up the elevator. But it was when we got inside her hotel room that she really took charge.

"OK, bathroom's right there. Get out of those dirty clothes, and get in the tub."

"Yes, mother."

"Hmpf. I wish. I so miss Mom. Do you have any memories of her?"

"Barely. I was nine when she and dad died. Once you left without anyone telling me, I was by myself."

"Well, you are not by yourself anymore. If I need to be mother and sister both to you, so be it. Now take off all those dirty clothes and get into the bath right this minute."

"But I'll be naked."

"I've seen it before."

"Now you do sound like a mother." She stuck her tongue out at me. I continued, "Besides, it's much bigger than you'll remember."

"Bragging, bragging, bragging."

It sounded pat. "Richard Pryor again?

"No; Dolly Parton."

"Who?"

"Get your ass stripped down and take your bath!"

With that motherly command, I hastened to the bathroom. Now, aside from ponds and public fountains, I haven't had a bath in years. I looked at a tub as if I had never seen one before. Still, Tam was right; I long ago needed a bath. I totally stripped down and placed myself into the marble bowl. I shivered from the cool surface, and shuddered when the first cold blast of water hit the tub. However, the hot water eventually kicked in and the water had reached a soothing warm temperature. I had almost forgotten another person was in the hotel room when...

"Are you washing?"

"Sheesh, Tam; I'm nude here."

"Dory, I am going to make sure you are cleaning up." She took a quick glance down. "Hmm, maybe you weren't bragging after all." She was obviously ogling my dick. I rapidly found a washcloth and covered myself, although I obviously had quite a tentpole. "Ooh, silly; am I really the first person to see it?"

"Well, occasionally some runaway girls would spend a night with me, and we had some fun. Most of them quickly went back to their folks. Those who didn't tended to get snatched up by pimps. A few homos tried to force themselves on me, but I've managed to keep my butt cherry, thank God."

"That's good to hear." By this time Tam had gotten on her knees beside the tub. She had removed her suit jacket and heels, and she had unbuttoned a few of her blouse buttons, revealing the nicest cleavage I have ever seen. "Ooh, you've gotten some nice muscles from that street living. Not big, but tight." She had grasped the bar and soap and began washing my shoulders and upper chest. I could not help but wonder if she had "tight" muscles as well.

"Oh, sis, I've missed you. So, how well off are you?"

"Well, my new 'daddy' became clay in my fingers. Some website had a how to guide on how to fuck one's daddy, and it gave a lot of advice I took to heart. Especially the last sentence: 'Daddy's last will and testament. Be in it.'". We both had a laugh. "Daddy was a C.E.O. of a company, and with some of my pussy persuasion, I became the new C.E.O. upon his death." She left my chest and started washing my legs.

"I bet his co-owners loved that."

"Well, to be truthful, daddy never learned that his co-owners became my 'uncles' as well."

"Tam, you slut!"

"Hey, it worked. Since then I've used my body to get my way, and have made a lot of money on favorable business deals. It was very equitable; they screwed me physically and I screwed them monetarily."

"So, what does your company do?"

"Mostly job headhunting, finding unique individuals for unique jobs. You have no idea how many people become unemployable by being too good to be hired by the jobs they can find, or not have the experience in the jobs they would be good in. We try to correct that."

"Sounds noble." By this time, her soapy hands had reached my crotch. She deftly pulled off the washcloth and began to wash my balls. Needless to say, I was startled."TAM!!!"

"Dory, I need to make sure you are healthy. If you have some disease, I need to know." She paused for a moment. "Yum, you definitely weren't bragging after all."

In all her ministrations, my penis became rock hard. I've never managed to measure it, but I knew I was above average, and this was the hardest I've ever been. Her right hand was soaping up my balls, while her left was stroking my cock. She was trying to pull my foreskin down.

"Tam?"

"Dory, I need to make sure you can pull your foreskin all the way back. It's a health manner." She continued her work on my cock, and then proceeded to give me a quick kiss on the forehead. That gave me a great view of her cleavage. I decided to kiss where her nipple would be if she wasn't still clothed. "Ooh, little brother wants me to be his mother after all." With that, she took her free left hand to unbutton her blouse, revealing a very sexy lacy bra. She freed a nipple from her bra, allowing me to begin suckling it as she continued to pull on my foreskin. "Ooh, that feels so good Dory." She noticed me starting to tremble. "Getting antsy?"

What Tam did not know was that it had been a long time since I last ejaculated, and the attention she was giving me down there was taking its toll. Almost immediately I squirted my cum all over the side of her face as I moaned in pleasure. I could not help but think she looked be-cum-ming with my love fluid over her cheek and lips.

"Ach! How about some warning? Sheesh!" She turned away from me, but I noticed she seemed to be taking her fingers and guided my cum into her mouth. "Your bath water is filthy. Unplug the drain and wash your hair under the shower." With that, she hastily stepped out of the bathroom.

A few minutes later, after I washed my hair, I stepped out. Tam was in a stunning nightgown. It was light purple with lace, and really accentuated her figure. Her breasts seemed propped up as if to say "Hello; please pay attention to us." I was sure many have.

"You call that a hair wash?"

"Hey, I did the best I could."

"Oh well, I guess I'll have to find you a barber, then maybe it'll look better. Room service should be here anytime."

Supper consisted of steak, grilled potatoes, and coke. Dessert was a wonderful strawberry shortcake; somehow Tam remembered that was my favorite.

'"So Tam, what are your plans for me?"

"I thinking about making my home somewhere around Orlando; I'm tired of the shitty New York weather. Finding good employees have always been tricky; you can be the overseer of our new home." She noticed that I had some steak sauce on my chin, and took her napkin to wipe it off. I rolled my eyes and responded.

"You sure have your maternal instincts. Have you had any children yet?"

"No, although I wish I had. Can you imagine the child support I could get from some of those high rollers? I've always wanted a family anyways, so it would be a double bonus. Why do you think I have spent so much time trying to find you? I need a family; I WANT a family. None of those limp dick Wall Street metrosexuals could get it done."

"Well, you seem to have the nursing part down pat," I said with a smirk.

"That was naughty, but I must confess I enjoyed it. You must have to," she remarked while taking her fingers to her cheek as if wiping off my cum again. With that, she proceeded to sit on the bed. I felt a bit naughty myself. I decided to join her on the bed, but instead of sitting upright I purposely laid myself so my head was on her lap with my lips near her breasts. I made a suckling noise.

"Silly brother," she said as she lightly slapped my stomach. But she did start uncovering so her nightgown revealed her beautiful breasts. Once freed from their bounds I began to suckle them; they seemed to taste like cherries. I began to feel her breasts; they were so soft, yet so firm.

"Aah, ooh, that feels so good. I need a baby so I can have my breasts suckled more often. Ooh."

I could continue to nurse from her breasts for days. I had no idea how long we were at it when she said. "OK, that's enough fun for tonight. Time to go to bed; we leave for Jacksonville at 11 am." With that she turned off the room lights by remote, and got under the covers on her side. I sighed. "Don't worry, I had someone pick up some clean sweats for you; we can go shopping later to get something more permanent to wear."

It had been years since I slept upon a clean pillow and under clean blankets; a vast improvement over grates and cardboard boxes. It had been only 9 pm, but still I felled asleep. Tam hugged me from behind, saying "Don't worry, mommy is here for you; now and always."

Eventually I woke up. I looked at the clock; it was 4:34 am. I thought to myself how in 24 hours I went from being just another bum on the street to having my sister back. I looked at my sister with what little light was available in the darkened room. She was so pretty. All this time and she never forgot about me, even though I somehow did forget her. Maybe it was because I've had a harder time of things. I wish there was a way I could repay her. After all, it is hard on the male ego to rely on a female for your subsistence. I took a peak under the cover. Wow, was she ever a woman. I only fooled with teen runaways, as they still had their looks and, unlike older woman who were also homeless, they were unlikely to be diseased. So many of my fellow homeless had so little to live for that they paid little heed to disease. I felt so blessed to now be in bed with my sister, even though she seemed to want to be my mother.

I looked again at her. The buttons on her nightgown seemed loose. I wondered if I could undo them. I began to carefully undo them, hoping Tam would not awaken. Wow! I knew her breasts were wonderful, and her legs as well, but her pussy WOW! It was perfectly smooth; all the girls I've slept with were very hairy. I could just barely make out her clit. I've never eaten pussy before; I had always been overcome by the stench. But one whiff of her pussy and I could swear I smelled flowers. I repositioned myself between her legs and began to lick her clit.

"Ooh, Michael, just like that."

Who was Michael? Must be one of the many men she seduced on her way to becoming a C.E.O. She was opening her legs wider. Seeing that I was having success, I became bolder. One of the women I slept with showed me how to find her g-spot, and I had become adept at finding them on other girls I managed to lay with. I was determined to conquer Tam's.

"Ooh, aah aah ahh, right there right there AAH, RIGHT THERE. OOOH!" Her pussy was starting to flood. At that moment, the brain in my head was saying to me, "she's your sister...you've gone too far." But my cock was standing at attention, and its brain had something to say as well. "She's made you spurt cum on her face and allowed you to suckle her tits, and on your own you've ate her out; go all the way. She has done everything she can to make you hers; make her yours instead and free me." Like in most men, my cock's brain won out. I flipped her onto her knees; I was going to give it to her doggy.

"Huh, what?" I entered her. "Dory, what are you dooo uuh uhh uhh doing? Oooh!" I started to really pound my cock into her pussy; it was so flooded that I had little resistance, even though it was the tightest pussy I ever remembered entering. "Oh god, oh god, I love it doggie. Aah Aah!" I grabbed her breasts and began pinching her tits.

"Who's pussy is this; who's pussy is this?" I demanded into her ear as I rammed her pussy with my cock.

"Ooh, your pussy bro, your pussy. Aah ah ah aaaaah! Fuck me, fuck me."

"Don't ever forget it," I said as I returned her onto her back. I felt close to cumming and was going to give it to her missionary style.

"I won't, I won't, aah aah ooh fuck me FUCK ME!!!"

I knew I couldn't hold out much longer. "I'm going to cum in your pussy!"

"Oh yes, fuck me fuck me, fill me with your lovely cum. AAH!"

"OOH!!!"

With that, I felt my entire soul rushing through my body and out my cock as my sperm absolutely filled her drenched pussy. I picked her legs up high into the air. Wrapping my right arm over her left leg, I placed my hand so none of my sperm could come out of her beautiful hole. I was entranced with her pretty anus; maybe next time, I thought.

"Oh, Dory, that was so wonderful. I love you."

"Not as much as I love you." I went to lay beside her, keeping my right hand covering her wonderful pussy. We cuddled for the next hour, my hand covering her pussy all throughout while I played with her breasts. It was only when we got dressed for breakfast that I removed my hand. For the next several days we made love at least once a day, often more.

Ten days later we arrived at Orlando. Driving by Wal-Mart on U.S. Route 192 in Kissimmee she told her driver, "Stop, I want to get something."

"From Wal-Mart?" I was stunned. "All your money and you want to stop at Wal-Mart?"

"Shush, I need something. Stay here." She quickly got out of the car once we pulled out. Thirty minutes later she finally came out, holding something in her hand. "It's blue, do you know what that means?"

"Uhh, no."

"Silly, it means I'm pregnant. "

"What?"

"It means you did what those limp-dicked businessmen couldn't; you made me a mother. THANK YOU!" With that she smothered me with kisses, and I wondered if her breasts would crush me. She could not witness my smile; I had succeeded in my plan; I gave her the one thing she most wanted; a child.

Nine months later we had a beautiful baby boy we named Terry Michael, after our father and her second "daddy". We've started a charity for young homeless individuals just outside Orlando, in hopes they have a safer existence. Our son, now one, is getting really active, and unbeknownst to him he'll soon have a sister. May his sister be as good to him as mine was to me.