Doing My Brother

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I looked at the view of Manhattan from my luxurious apartment and took it all in. I had made it, I’d hit the big time. Every time I enjoyed the skyline, I was reminded of my accomplishments. As I had so often done before, I went to reach for a cigarette. I stopped myself as I had made a promise to Keith that I would quit. Oh, the things we do for those we love. Fortunately, I didn’t promise him that I would quit drinking, so I poured myself a large tumbler of Bourbon and reflected on the events of the last six months.

Keith is my brother and he had come to stay with me due to unpleasant familial circumstances. Our parents are finally drying out after years of drunken and irresponsible behavior. Let me be clear – I love them, but realized 5 years ago that I had to cut ties to save my sanity. I moved to Manhattan and became a successful broker on Wall Street. I know that my striking good looks are very good for business. As I near the age of 30, I’m proud to say that I can easily pass for younger. I’m 6’1″ tall – yes, you read that correctly – and my hair is jet black. My measurements are 36DD-27-38 so I certainly stand out in a crowd. My lifestyle affords me anything I want and I go to the gym religiously. I also firmly believe that regular sexual activity has kept me looking young and feeling healthy. I’m not monogamous and have had several lovers, of both sexes. I don’t discriminate; I love the pounding I can get from a hard cock and the warm, sensual embrace of another woman. Of course, whenever I can manage it, I enjoy both.

I was a very successful, happy individual and living the life I wanted when I got a call from my parents’ attorney. He told me the story about them drying out and wishing to make amends for their past behaviors. They had gifted me with a rather large stipend, although I really didn’t need nor want their money. I discovered that there was one condition attached to it.

I could have refused, as I didn’t really need the money, but I was pleased that my parents had finally made the decision to get sober. I truly hoped that they would stay that way. I had always hoped that one day; we could mend fences and be a family again. I was also quite curious as to what the condition might be.

As it turned out, the condition was that my brother Keith came to live with me in the city. Keith is my younger brother by 9 years, a “surprise” baby for our mother. He’s a well-mannered young man who has done very well in school and he is one of the reasons my parents made the decision to get sober. Keith decided that he would like to attend university and then, medical school with the choice of becoming a doctor. Both of our parents wanted to be sober so that they could live to see him graduate. I thought that it was a bit ironic, as now my brother could claim he had already saved two lives. I was very proud of my kid brother. It couldn’t have been easy living with those two and maintaining the GPA he did. I agreed to let him come and stay with me while he attended university. I have 4 nice-sized bedrooms and he could have one of those. As for my rather flamboyant lifestyle, I would explain that to him as well. If he decided that he would rather live elsewhere, we had more than enough money to find him a decent apartment and I would be able to keep a watchful eye over him.

What I mean by “flamboyant” is this – I often entertain guests and throw several parties per year. The drink flows and soon after, clothes are often discarded and the parties become a bit more – intense. I don’t hold myself back and am almost always a very willing participant. Often, I’m the center of attention as I do tend to stand out in a crowd. I had no intention of slowing down simply because my brother was going to be here. If this made him uncomfortable, he could choose to leave for the night or he could find another place to live. I work very hard but I am sensible enough to know that I need an equitable balance in my life. I play just as hard as I work. It keeps the stressors out of my life. I knew Keith might be a bit shocked, so when he arrived, I would lay it all out for him and let him decide what he wanted to do.

As it turned out, my brother was thrilled to have a chance to live in the city. When I told him about the parties, he had a reaction that I hadn’t anticipated. Perhaps the reason for that was his being my brother. Had I told any other living, breathing male about my little bacchanals, I would have seen it coming.

I explained to him in entirety about my soirees and left no details out. His dark brown eyes widened and he smiled as he said “Oh Julie, those sound so cool! Can I come?”

Why hadn’t I foreseen that? Of course he would want to attend! Lots of people would give up all sorts of things to attend one of my functions. They are attended by sexy, infamous people of both genders looking to have a good time. I always have them catered, so there is food and drink abundant. Keith was a handsome young man and I am sure with his good looks, he was popular with the young ladies back home. Dress him right and he would be very popular with the ladies here as well. Despite gebze escort all of that, I still didn’t want him attending these parties and doing something foolish, thus, embarrassing me. I also wondered if he might also have inherited our parents’ love for alcohol. I love my brother, but I also value the connections I have made and my reputation. What to do, what to do?

I hadn’t given my answer as yet and I looked over at my gorgeous kid brother. He looked a bit dejected and I felt sorry for him. He was as attractive as most of the men who attend my parties, he just wasn’t worldly or urbane. If he had a bit of seasoning, I would most definitely have invited him. He would have been a hit with several of the ladies.

“I really have to think about this,” I answered him with full candor. “I wouldn’t want you to be uncomfortable around some of my friends. I wouldn’t want you to make some silly mistake and be embarrassed.” I also underscored the fact that I wouldn’t want him embarrassing me and causing a dent in my social status. I had worked very hard to get where I am today.

I thought long and hard about the situation and then, I got an idea. I hire several attractive young “servers” to help out at my soirees. Each of them is paid very handsomely and they are allowed – encouraged is more like it – to mingle with the guests. I decided that I would let Keith work as a server and he could earn some extra money that way. He would also meet some attractive women and be able to participate at some point.

I put in a call to my friend Jamie. She always helps me with fine-tuning the parties. I have almost no secrets from Jamie. I told her about my plan and we conversed for a little while. “I’ll be there as soon as I can catch a cab,” Jamie told me. She’s a trust fund baby and doesn’t need to work. In order for my plan to come to fruition, I would need Julie’s full cooperation.

Jamie arrived about 30 minutes later, looking gorgeous as ever. We kissed the way we always do, tongues mingling and passions tingling. I’ve made love to Jamie on several occasions and I never tire of looking at her slender, silky-smooth body and beautiful blue eyes. Had I not a purpose in mind for her visit, I likely would have taken her to bed right there and then. I wonder what Keith would have done as he heard his older sister sexing it up with a hot, honeyed blonde? I had decided to confess my bi-sexuality to him to avoid any future complications. Still, to actually see it up close and personal is a different thing altogether.

“So, you’d like me to train your brother so he can attend one of our little functions, hmm?” Jamie smiled at me. The training would be rigorous and intense, but if anyone could do it, Julie could. “Do you think he’s a virgin?”

I shook my head. “Not looking the way he does,” I answered. “I’m sure there are a lot of girls back home lining up to screw him. He’s attractive and well-mannered, so unless he planned to save himself …” I snickered “… he’s been around the track a time or two.”

Jamie looked at me with a grin on her face. “Have we been checking out our brother, Julie dear?”

I sighed. “Not really, but he IS hard to miss. He’s a tall young man with broad shoulders and muscles. Even I’m not totally immune to someone like that. With proper training, he’ll be the hit of the next party.”

“You know how – intense – my training sessions can be.”

I nodded. “I do and I want him rigorously trained,” I told Jamie. “I want him to be a super-stud, the kind of lover that women desire. I want him to become a stallion and live up to his full potential. When he starts university in a few months, I want those hot little coeds to be throwing themselves at his feet.”

Jamie grinned and commented “I’d have to be here night and day for that.”

“This place is huge, I have plenty of room if you want to stay,” I said. “I’ll pay any price you ask, just …”

Jamie waved her hand. “Oh darling girl, do not be gauche. I don’t do this for the money; I have more of that than I will ever need. I do it for the challenge and the fun of breaking in new, young lovers. I’m up for it if he is. Where is our new recruit?”

I called for Keith and he came out of his room. One look at Jamie was all that he needed and why not? Her short blue mini was almost indecent and she had on 5-inch stiletto heels. Everything she wore was designed to showcase that marvelous, toned and tanned body that I knew so intimately.

“Close your mouth Keith, it isn’t polite to stare,” Jamie instructed him from the get-go. “I am flattered by the attention, of course. So, you do find me attractive?”

Keith was a bit taken back that Jamie knew who he was, but he did manage a nod. “That’s good, as we will be working closely together. I will let your sister explain what I mean by that. Julie, in which room will I be staying?”

I pointed to the guest bedroom, which was right beside mine on one side and Keith’s on the other. Without even giving my brother a chance to recover, she poked him in the chest and told him “Meet me there göztepe escort in 20 minutes, no earlier, no later. Don’t be late! Punctuality is a virtue!” With that, she turned on a silver-tipped heel and walked sensually towards her room. My poor brother was still at a loss as to what was going on around here.

“Uh, I think I missed something,” Keith looked at the room and then, back at me. “Jules, would you care to explain?”

“IF you still want to attend my next function, I’m going to let you,” I said to him. “However, it will be under my conditions and that’s where Julie comes in.” I told him why Julie was there and his face went through the gamut of expressions. When I finished, he was shaking his head in disbelief.

“Okay, let me see if I have this straight. I get to attend your party, wear a nice tuxedo, mingle with hot women AND I get paid?” He asked. I nodded yes and Keith shook his head again. “PLUS I get to fuck the hot blonde in the guest room?” Once more I told him yes.

“Wow, that’s a great arrangement, except I sorta already know how to fuck a girl. I haven’t exactly been celibate back home,” he concluded.

“That is precisely the point, in a nutshell,” I said to Keith. “You’ve been fucking girls, younger women. You likely don’t have a lot of finesse. Jaime is going to put you through your paces and when she is done with you, you’ll be able to lure any woman you desire into bed and pleasure her with style. You’ll be quite the cocksman, let me assure you.”

Keith still wasn’t sure, but I noticed the time and shoved him towards the bedroom. “You heard what Jamie said,” I told him. “Don’t keep the lady waiting.” I will admit to being a bit jealous of Jamie. I myself wanted to be the first person Keith fucked. Oh, I know what you’re thinking, but we’re all adults and these are modern times. You would be surprised if you knew how many people had experienced or fantasized about incestuous relationships. I have no qualms about the wrong or right about sex between members of the same family. Why should I? My brother is gorgeous and I wanted him, incest be damned! However, I am wise enough to know that he would benefit from Jamie’s tutelage and when I finally did fuck him, he would give me a really good ride.

I was very tempted to go in and watch the proceedings. Part of the reason I host these little shindigs is that I am quite the voyeur. I love watching people fuck almost as much as I love fucking. I wondered how far they had gotten and I had to pour myself a drink to take my mind off of what was going on in the guest room. Before I knew what had happened, I had poured 3 very large, stiff drinks and nearly 45 minutes had passed before a barely-dressed Julie came out to join me.

“What’s the verdict?” I asked her.

Jamie motioned for me to pour her a drink which I did. Lifting it to her lips, she smiled. “Well, let me sum it up for you. The boy has potential. He does have endurance, I’ll give him that. He’s not at all threatened by an aggressive woman and he does pay attention in bed,” she told me.

“Go on, please.”

Jamie smiled as she knew I realized she had a “but” coming. “He doesn’t have much grace in the bedroom and he isn’t much for foreplay. That might be fine for all of those adorable young coeds he’s been banging, but it won’t play in our crowd. He also needs to learn to mix it up a little and to pace himself. I know I can bring him up to speed, if that’s what you want me to do. Is it?”

I smiled and Jamie knew she had her answer. “You’re going to fuck him yourself, aren’t you?” She asked.

I leaned forward and kissed Jamie, hoping for a trace of my brother’s cum on her soft, full lips. No such luck! “You know me too well,” I chuckled as our lips parted. “Can you blame me?”

Jamie shook her head as she looked at me. “Not for a minute. I’m make sure he’s ready for you, baby. He will be the stud of your dreams by the time I get through with him.”

“I’m sure he will,” I said to her. “I have the utmost confidence in you and your abilities.”

We all had a nice dinner together and you would have thought we were just 3 friends sharing a meal, not three perverts about to undergo life-altering moments. Julie went to bed early, but not before instructing my brother to come to her room at 11 PM sharp and to bring wine. I stayed up and watched some television, keeping a mindful eye on the clock. When the news came on, I went to Jamie’s room. The door was mostly open, so I looked to see what I could. I got an eyeful!

To begin with, my brother was really HUNG! He had to be at least 8 inches and the girth was impressive. Jamie was stroking him with her hands as if she was taking measurement. “You’ve got a nice cock here, Keith,” I could hear her say. “I’m going to teach you how to really use it to get a woman off.”

“I haven’t had any complaints, Jamie,” my brother replied.

“You should call me Miss Jamie when we’re like this,” Jamie corrected him. “Of course you haven’t had complaints; you’ve been screwing young coeds with little or no experience. halkalı escort That won’t be what goes on at Julie’s functions. To begin with, you need to be a bit more vocal. A woman likes to hear that she’s pleasing the man.”

Keith was paying attention, I’ll give him that. Jamie started to go down on his massive cock and he told her how much he liked it and how soft and hot her lips were. She went up and down like she wanted his cum, which I’m sure she did. When Keith finally did shoot his load, it was a nice amount. I wished I could have been there to share it with her, but this was her show and I was only observing. She looked across the room and winked. The little bitch knew I was watching and had likely left her door open on purpose!

Jamie’s big blue eyes were open wide as she sucked on my brother’s cock. She was using her long blonde hair to tantalize him as she sucked on it, letting it trail over his body to tease him. To be sure, he couldn’t ignore the 34DD tits that were near his face and of course, Jamie wasn’t going to let those go to waste. She gave him a vigorous titty fucking before letting him cum all over her luscious tits. I was so tempted to run in and join them, but I stayed put and enjoyed the show that Jamie was providing for me.

She flashed him a million-dollar smile with lots of pearly-white teeth. “Now baby, it’s time for you to do for Miss Jamie,” she said to him with full command of his attention. “You’re going to provide me with lots of foreplay – don’t miss a spot, understand? Just because I have these luscious boobs, that doesn’t mean you should ignore the rest of me. Show me that you appreciate my gorgeous body and you’ll get to see it a lot more often.”

I hoped that my brother was paying attention, because I really wanted to be there and see the pay off. Slowly, my brother started to pay homage to Jamie’s body. He kissed her lovely face, using his tongue to probe her mouth. He kissed the side of her neck and behind her ears. While he was kissing her, his hands weighed her lovely tits and he caressed them. I watched with interest as he did this, hoping he had picked up on her subtle clues. He had, for he didn’t maul Jamie’s breasts, instead, he caressed them lovingly and massaged them gently. A soft moan escaped her lips as he brought his mouth to them and sucked each nipple before moving down her body. Her stomach is flat from constant working out, both in and out of the bedroom. My brother took time to appreciate that as his hands roamed all over.

Watching my brother loving my close friend was really getting me aroused. Every inch of me wanted to run in there and join them. I pushed those urges down. This was Jamie’s scene and I didn’t want to spoil any of her plans. It might have made Keith nervous to know his big sister was watching, no matter how hot the show was.

Even once he reached Jamie’s nether regions, Keith didn’t immediately go to her pussy. Jamie was wearing stockings and Keith slowly removed them, kissing down her legs as he did so and removing her high heeled bedroom slippers. He even gave her a tiny foot massage and that got a huge grin that he probably didn’t see. Oh no, he was too busy kissing back up her legs to that cherished spot. With great care, Keith parted the lips of Jamie’s pussy and began to eat her out.

I love to watch other people having sex. I don’t love it purely from a voyeuristic standpoint, although that is a large part of it. I love to watch their faces and enjoy the different techniques. You can learn a lot about sex by being an observant voyeur. I learned that my brother was going to make one fabulous stud once he had some experience under his belt. He was being meticulous while licking Jamie’s bared pussy. He wasn’t rushing and he was not afraid to go deep. Jamie was squirming around the bed and her fingernails were digging into his scalp as he ate her cunt. I could also see that his cock was showing renewed signs of life.

I was so horny by this point and I really couldn’t say who I wanted more – my sexy kid brother or the voluptuous blonde he was having sex with. Her body didn’t have a single flaw and I dearly wanted to run my tongue all over it. I also wanted to help my brother get stiff and ready again and slide his big fucking cock between her tits. I think tit-fucking can be really sexy and I wanted him to fuck mine at some point. As I watched them having sex, I went almost insane with desire.

“Move around, let me have your cock and you can keep eating my cunt,” Jamie groaned. “You are going to be one talented fucker when we get you trained. The ladies won’t be able to keep their hands off of you.”

I was hanging on every word and I will admit to being a bit jealous. Once I had that cock inside my own needy cunt, I wanted to keep it for myself and from then on, I would be the one to decide who Keith fucked. I wanted to barge into the bedroom, steal Keith’s cock from Jamie and have him fuck me and keep fucking me and never stopped. It was taking almost all of my self-control not to do that. I am sure this is one of the reasons incestuous relationships don’t always work; there are feelings of jealousy when outsiders get involved. I knew that it wasn’t rational, so I let Jamie train him into a perfect, gifted fucking machine. My rational mind knew that he’d be the better for it when she was done and the lover that would come to my bed – eventually – would be worthy of being my lover.

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