Brotherly Love

Brotherly Love

"Josh, you must be crazy," was all I could manage to get out of my mouth after listening intently as my brother and I sat having an impromptu breakfast at a local coffee shop. Usually, we have a good relationship with very little pressure either way since he has filled in as head of the family since our parents passed several years ago and our sister lives on the left coast, far from us and the chilly northeast. Josh helped me get through college and get my Masters, still allows me live in the guest bedroom of his three-bedroom house rent free as long as I contribute to the utilities and paid for my share of the food budget, a more than fair arrangement in my opinion.

Today he invited me to breakfast at a coffee shop before work, something out of the ordinary, so I knew something was up. Nevertheless, with a free breakfast on the table, it was definitely worth getting up a little earlier to find out what it was. Josh was there when I arrived having stayed with his girlfriend the night before, and he greeted me with a smile and a hearty "Good Morning" when I sat down. It almost felt more like a business meeting than a family breakfast as Josh seemed nervous and distracted, quite unlike his usual easygoing self. The waitress brought coffee for me and took my breakfast order and Josh sat silently until she left, before asking how I was doing and thanking me for joining him.

After a few minutes, he finally got to the point. "I have a little problem and would appreciate your help in making it go away. It's nothing major but you are the only one who can help me and as much as I hate asking you for a favor, I am hoping that you will consider my request before rejecting it out of hand. It is not about giving me money or anything illegal, but it does require your involvement in something that might not appeal to you."

"While I am a little apprehensive after hearing the introduction to your request, I am curious about what you want from me, particularly since it is not money or anything illegal."

Josh smiled and after the waitress set my breakfast on the table and refreshed our coffees, he picked up where he left off while I began to eat. "Okay, here it is and please hear me out. You know that the first Friday of the month I play cards with some old friends and a couple of guys from the office, a nice bunch overall. There are about ten of us that play regularly, and it usually works out that we have the necessary five and one or two others to get drinks and snacks while sitting in when necessary. The stakes are modest, and no one takes the game so seriously that people get hurt if they lose but occasionally certain changes are initiated to keep it interesting and usually it's great fun.

"When we played two weeks ago, I was doing very well and when one fellow suggested something to spice up one of the last hands of the night, I felt comfortable enough to agree without seriously considering the ramifications of the bet and I wagered something that I had no business to risk. I had drawn two cards and was sitting with a straight, and judging by what was drawn by the others at the table and the way my luck was running, I felt I had the hand locked.

"It was at this point that James, the fellow that was the only one left and a guy you have also known for years, said that he would throw in two tickets to the Celtics game if I agreed to arrange for something 'special' between you and him. As you can imagine I wanted to go to the game and felt confident that he could not beat a straight, so I hastily agreed. The fact that I could lose never dawned on me until he turned over the final card of a flush and everyone in the room burst out laughing. I felt the heat rise in my face and my shirt suddenly felt damp while the only thought running through my head was 'what have I done?'"

I rested my knife and fork on the plate, wiped my lips with the napkin and took a long sip of coffee before I asked the obvious question, "What exactly did you agree to on my behalf, dear brother?"

"Well, that's the thing. It was left very vague on my side although the tickets to the Celtics game were easily quantifiable. When I asked him to clarify it after the laughing subsided, all he said was that he would tell me before he left. The idea that I would have this on my mind was strategic on his part since I would be distracted and unable to concentrate on the game. It was diabolical in its simplicity but very effective."

"Not that I want to sound like a broken record, but what exactly did you agree to?" I responded in a stern voice.

Josh was clearly getting nervous and his face was becoming very pink but he remained quiet and took a drink of coffee before answering. "I cornered James in the kitchen while the guys cleaned up and put the cards away, and he told me that he always liked you and he would like you to come to his apartment for a few drinks with him one evening. He said that he expected you to leave your inhibitions at the door and spend the evening with him while in the nude and open to whatever comes up."

"Josh, you must be crazy! You are asking me to go to your friend's apartment and spend an evening with him totally naked. I am not so naïve to believe that he wants me to strip and then watch me walk around in the nude without expecting anything else. Did you ask him about that?" I hissed.

"Of course I did, I'm not that dumb," he replied.

"I will reserve judgment on that point until you tell me what he said when you asked him about his expectations," I said caustically.

"Look, he's a nice guy, you know that. He's not some macho degenerate that enjoys hurting people," he replied and then sat quietly.

I waited a moment and then growled at him, "I feel so much better now! He's a nice guy that doesn't enjoy hurting people! What the fuck, Josh. If he's such a sweetheart, why don't you go in my place?"

"Rob, you know I'm straight and I don't like the idea of a guy sticking his stiff dick in my mouth, but if I did, I wouldn't be asking this of you. Do you think that I'm that insensitive?"

"You're such an asshole, Josh," I said while trying hard to control my laughter. "You are now my pimp in addition to being my brother. How much are the Celtics tickets worth?" I asked.

"He said that he could get $500 for them so I asked if I could give him the $500 and call it square, but he said that that was not the bet. He insisted on an evening with you, in his apartment, naked, and at least one orgasm," he replied.

"Oh, this keeps getting better! Now it's not just spending an evening with him naked, but he expects an orgasm as well. You've become a pimp! What if I refuse?" I asked.

"He said I could buy the evening back, but it would cost $1,500 and I would still owe him something although it would not be an evening with you," he said. "I don't have $1,500 right now and God knows what he'll ask for next and that is why I am asking you to think about it before saying no outright. Who knows, it might be fun to have a hot date with a sweet, good-looking guy, so please consider it. I am your brother after all and always have your best interest at heart."

"You're a moron!" I said quietly while stifling a laugh.

"How about this? I will arrange for the three of us to meet for a burger and a beer one evening this week so you can renew your acquaintance, and you can tell me what you think afterward. If you feel strongly against helping me out, I will try to work out some other arrangement with him that does not involve sex. I mean, that seems reasonable, right?"

I took a minute to think about his proposal and had to admit that it was not the craziest thing that I've heard from my brother recently. From what I remembered, James was a decent guy and certainly not bad looking, and if Josh paid for dinner and was willing to try to figure out an alternative plan if I decided not to go along with this scheme to clear his gambling debt, what did I have to lose? And maybe he was right, it could be fun in a weird sort of way. Finally, I said "Okay, set it up and I will let you know one way or another after the meeting. But remember, if I say no at that point, that is to be the end of the discussion, no more bullshit from you. And one last thing: if I agree to settle your bet, you will owe me big time and I don't want excuses when I claim my compensation. Those are my terms so do we have a deal?"

"Rob, I knew you wouldn't let me down."

Later in the day, Josh called to tell me that he spoke to James and set up a dinner meet in two days' time at one of the local bars that had great burgers and a good selection of alcohol. He was very upbeat and pleased with himself and went on to say that James seemed excited at the prospect of seeing me again. In my opinion, James must have sensed that he was getting closer to receiving his winnings from Josh and this inflated his ego and confirmed his gambling prowess. Also, he proved that he had something on my brother and in the end he will get a prize, either me or $1,500 and this made him extremely happy. James was happy, Josh was relieved and happy, and I was very nervous and still pissed at my brother for dragging me into this.

When I got to the bar my brother was already sitting at one of the high tables with a nice looking fellow that I vaguely remembered and assumed to be James. He was neatly dressed and looked tan and fit and gave me a pleasant smile when I got to the table. Josh gave me a warm hug and James extended his hand as Josh introduced me. His grip was solid and firm, not bone crushing firm but firm enough to indicate reasonable strength being held in check to be friendly. I looked into his eyes, hazel or greenish and soft. My initial impression was a of a sensitive man, yet strong and focused, not someone easily manipulated. I remembered that I met him several times in the past but those situations were nondescript and I was younger as well. It is different this time and we both knew it; I felt like I was on a blind date, intent on making a good impression while knowing that that was not the case entirely. I was there for a specific purpose but if I went through with my brother's request and I presented myself well, I could see myself having a nice time with someone that I presumed to be a gentleman.

Over dinner, James asked how Josh explained the circumstances leading up to our dinner and I relayed my version of events in a lighthearted way, permitting us to share a few laughs, while avoiding the ultimate discomfort I felt when Josh first told me that he wagered me in a card game. James was very nice about it and when Josh went to the men's room a bit later, he confided in me that he had seen me in town a few times and was looking for a way to meet me again. Things worked out over cards, and he decided to have some fun with Josh as well. He said that if I was uncomfortable about a one-on-one meeting after dinner tonight, he was prepared to ease off on Josh, but I was not to tell Josh beforehand. He was proving to be more of a gentleman than I imagined, and I found myself intrigued by the prospect of having him to myself for a while.

At the end of the night, we went our separate ways and when I saw Josh at home, I told him that I would agree to his request but he still owed me, it was not a freebie . He said that he thought that James and I would hit it off and was happy that it worked out, forgetting that he was not setting us up for a date but in fact was handing me over to be a sex toy for a one-night stand. I resigned myself to accept his interpretation of events based upon my feelings for the fellow that I had dinner with tonight, believing that people meet many ways, and this could very well be just one of the strange stories that people laugh about years after the fact. Josh gave James my phone number and left it to us to decide on a date for our rendezvous but reminded me that he was still obligated to meet his end of the bargain with James until our date took place.

James and I agreed on a rendezvous for the following week and as the date approached I became more apprehensive but not necessarily in a bad way. I was nervous but mainly because I did not know what to expect. I hoped to meet the person who I had dinner with, but I didn't know if he was being especially nice that night and someone else would be waiting in his apartment for my arrival. Nevertheless, I primped about my appearance and fussed about my outfit so that I made the best impression possible just in case. I knew that I would not be spending the evening fully dressed but I did not know how long the evening would last. Would James insist that I shed my clothing right after I arrived and then get to the sex in short order or would he make an evening of it, having me bring him to the edge repeatedly before reaching an orgasm and allowing me to leave. It was hard to devine the path that the evening would take but I decided that I had to be ready for almost anything.

After a lot of thought I decided to keep things simple. I wore some light makeup and combed my hair straight back, used a pale pink nail polish that was subdued but fashionable, and wore sheer black stockings, black lace panties and a black satin camisole under nice slacks and a button-down shirt. I wanted to feel sexy and look sexy as I shed my clothes, but I did not wish to present myself as female in case that was not what James preferred. Tonight I was simply paying off a debt and if it went farther than this, I could adjust going forward.

James answered the door in nice cotton slacks and a polo shirt, looking fresh and well groomed, and immediately my nervousness seemed to dissipate. He gave me a broad smile and by the twinkle in his eyes I could tell that he was pleased to see me. After I walked into the foyer, James closed the door and then kissed me on both cheeks in a European fashion and I leaned in to kiss him on the lips before catching myself, "Oops, sorry. You made me feel very comfortable and I just realized that we hardly know each other outside of chance meetings with my brother and other friends."

"When you're in my apartment, I want you to be comfortable and feel free to say and do whatever you are inclined to do. If I made you feel comfortable, that is a step in the right direction and I am glad." James leaned into me and kissed my lips like I was going to do to him and I felt myself begin to melt.

"Did you turn up the heat in here? I suddenly feel warm and my face feels flushed," I said softly.

"Then let's go to the terrace for some air and I will bring a glass of wine so you don't get dehydrated," he said. "I don't want you have a bad experience on our first date."

"Is that what you believe this is, a first date?" I replied as I walked to the terrace and James went to the kitchen to get two glasses of wine.

"Well, I wouldn't consider dinner last week a date since your brother arranged it and he stayed the entire time so, yes this is our first date," James said loudly with a laugh.

"Hmm, then would you consider me a slut if I let you have your way with me on our first date?"

"Yes, I think that would be the correct term," he said handing me a glass, "and a bitch if you didn't. So, tell me, how shall I remember you?"

"Sluts have more fun," I replied before taking a sip of wine and looking into the distance.

I leaned on the handrail as I watched the roads in the distance and before long James came to stand behind me, placing his hands gently on my hips and pulling me back toward him. He leaned forward to kiss the back of my neck and I moaned quietly as I savored the feeling of his warm lips against my skin. "I've liked you since the first time I saw you years ago and when I saw you again around town recently, I knew that I had to meet you on a personal level. Now that I have, I know that my instincts were correct, and I am glad that I found a way to use Josh to get us together. I don't want to jeopardize what might be a nice relationship by being rude, but I want to feel your warm body next to mine."

"I assume that you know that you can simply tell me to remove my clothes and climb into bed if that is what you want," I said. "You don't have to pretend to like me on my account as I came here tonight fully prepared to submit myself to you for whatever purpose you desire. Josh explained that you had the right to have me remove my clothes and remain that way for as long as you wanted. He also explained that I had to give you an orgasm whatever way you preferred and that I should not expect reciprocation. I am your slut for the evening, a sex toy for the taking, and all I ask is that you do not hurt me physically since that is not part of the agreement."

"Rob, do you think that all I want is what you describe? Would you prefer that I tell you to remove your clothes and get on your knees? Is that what you think of me, of yourself?"

James turned me around so that I faced him and stared into my eyes. I could see the emotion under the surface and felt the heat of his body coming through his clothes. He was in control of his emotions and acting like a gentleman but I could sense that he was struggling to keep his desire in check. I leaned in close and kissed him on the mouth, separating my lips to allow his tongue access and he took full advantage of the opportunity to drive it between my lips and into my mouth. I moaned loudly as I felt my body start to twitch in his arms and I wanted nothing more than to have him take off my clothes and push me onto his bed. I wanted to feel him on top of me, I wanted to feel him penetrate me and use me like the wanton slut he teased me about earlier. I also wanted to feel his erect penis slide in and out of my throat until he pulsed streams of hot semen into my stomach. I wanted it all and I wanted it to last until the night was driven away by the morning light.

I pulled myself away from him and moved to the side of the terrace creating space between us. Slowly I unbuttoned my shirt and removed it, exposing the black satin camisole underneath it and stood staring at him. Next, I removed my loafers, unbuckled my belt and unzipped my pants allowing them to fall to the floor, and stepped out of them. Standing there in the evening darkness wearing a black satin camisole, sheer black stockings and black lace panties made quite a picture and judging by the look on James' face, I clearly got his attention.

"Rob..." James started to say something, but I cut him short.

"Robin now, please."

"Okay, Robin, may I show you the rest of the apartment?"

"Starting with the bedroom, I assume?"

"We could start there if you like," James replied.

"Well, since I am your guest I will let you decide, but make no mistake I want to see everything."

I grabbed my clothes, and we went inside where I deposited my stuff on the living room chair, taking a condom and a packet of lube from the pocket of my pants. James refreshed our drinks and proceeded to lead me to the bedroom where we stopped only long enough to place our glasses on the night table and enjoy a steamy kiss. I then helped James get out of his clothes and admired his fit physique, swimming muscular not defined like a weightlifter muscular, with a nicely proportioned, rock-hard erection pointing to the ceiling. Seeing him like this for the first time had my penis stretching the lace of my panties, and I was beginning to breathe heavily in anticipation. I wanted him and I could tell that he wanted me and was growing impatient by the waiting.

Pushing him backward onto the bed I crawled on top of him and sat astride his thighs. Looking into his eyes, I removed the camisole over my head and moved his hands to my chest, guiding his fingers to my hard, erect nipples. James began to finger them, drawing little circles while tracing the areolas, and then squeezing them gently between his thumb and forefinger causing me to shiver and grab his forearms. "A little harder please," I said, "I want to feel the sting of pain in my nipples from your touch." James did as instructed and I began to rock slowly and gently, feeling his erection rub against my abdomen, while electric sensations traveled from my nipples to my genitals.