Rich Man's Son

I'm Randolph Hamilton DeWinter. My mother was a Randolph before she married my father and our family is considered one of Virginia's old "first families". That crap means nothing to me, but it, and "social position", are VERY important to my parents. I know that my parents loved me and that they thought they were just making life easier for me by making all decisions related to my life for me without ever asking my opinion about anything.

As a result of the "concern" for me, I went through my childhood and teen years as if I was wrapped in a tight cocoon and hardly able to breathe. What made it even worse was the fact that we lived in a huge Brownstone on Central Part West and had a full compliment of servants. They did everything for me from making my bed to picking up after me. As a result, I never had any of the household chores that almost all healthy young boys have.

Although I had a streak of independence, I generally found it far easier to just give in and go with the flow than to try to convince them that I would rather do something else. As a result, all decisions relating to the schools I attended, the subjects I took, the sports I played, the clothes I wore and the friends I was allowed to have were all made for me. As you might imagine, my "friends' were all stuck-up snobs without and independent thought among them? I thought they were all assholes and despised them thoroughly. Of course that only made me look as conceited and stuck-up as they!

My first real chance at independence came when I was sent away to the "correct" preparatory school (Groton, of course). It turned out that my roommate (Charles Lowell Carlyle) was also an only child from an old Connecticut family that had close ties to the Lowell family in Massachusetts. Both of our families were delighted when they found out with whom their son was rooming and were doubly pleased when we let it be known that we actually liked each other! Charlie was a much under his parents' thumbs as I was, but he, too, had an independent streak bursting to express itself and we both kind of re-enforced each other's feeble attempts to live our own lives.

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Charles was as much a virgin as I was and although both of us "knew" about sex, we were totally naive and inexperienced. At this age, we were both probably just gangling under-developed teenagers, but we both began to find each other more and more attractive from a sexual perspective!

The first sexual intimacy we shared was when I leaned forward and gently pressed my lips to his in a very chase and gentle kiss. As we slowly drew apart after the light touch of our mouths, our eyes met in pleasured awe at how very daring we were!

I thought, "To hell with this modesty crap, I want to REALLY kiss this guy!" I grabbed him in a bear hug, pushed my lips up against his and, as his mouth opened a little in surprise, I quickly stuck my tongue into his mouth as far as it would go. He giggled and began to suck vigorously on my tongue, squeezing me as tightly as I was holding him. When he finally gave me back my tongue, we switched places and I sucked on his until we had to come up gasping for air.

After the kiss, we both looked at each other, said "Wow!" at the same time and immediately started to unbutton each other's shirts. When we had out shirts unbuttoned and pulled out of our pants, I pushed Charlie onto his back on one of the single beds in our room and fell on top of him. His chest was a hairless as mine and we both only had small tufts of hair in our armpits. His nipples were as flat as mine, but when I started to lick them, Charlie moaned in pleasure and the center part of his nipple suddenly grew and hardened to the point that I really Had something to suck on. Charlie loved it and soon threw me on my back and gave me the same workover.

It wasn't long before each of us was trying to get the other's belt undone and pants unzipped. We each kicked off our loafers allowing the other to slid our pants to the floor. We then slowly slid the other's underwear down past each other's hips until our already erect cocks sprang up in our faces. At this age, our cocks were only about 5 to 6 inches long, but we thought them to be huge and just stared at them for several minutes. As it turned out neither of us had ever seen another guy with an erection before and this was truly a "first" for both ofus.

We began to stroke the other's cock and gently massage it. Charlie took the lead this time, swung around into a 69 position, and started to lick my cockhead. "God, what a sensation!" I quickly joined suit and was soon sucking on each other's cock as if we knew what the hell we were doing! We were both so hot and horny that Charlie soon said, "Randy, I'm just about to cum!"

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I told him I was too. Inasmuch as neither of us had ever tasted cum before, we stopped sucking each other and just jacked the hell out of each other's cock. Cum was soon flying out of both of our cocks in all directions! Man, did we blast out a load! Both of our chests and bellies were coated with strands of thick white cum. We just looked at each for a bit and then burst out laughing in pleasure at what we had done to each other! I decided that I just had to know what Charlie's cum tasted like so I tentatively stuck out my tongue and licked a particularly large glob off one of his tits. I allowed it to swirl around my mouth a little and then gulped it down. I said, somewhat in awe, "Charlie, your cum is sweet! I love it!"

That was all it took for Charlie to sample my cum. When he had, he grinned at me. "Randy, yours is somewhat more salty than sweet but it's not bad! I think I could swallow your cum the next time!"

We then went into our bathroom where we showered together, washing each other's body thoroughly and lovingly. By the time were through washing each other, we both again had full erections but decided to save out fucking experiments for another time and just dried off, hugged each other again, kissed deeply, and got dressed.

That night we tried fucking each other, although neither of us really knew what he was doing. Charlie took to fucking like a duck takes to water and quickly found how to rub his cockhead against my prostate. The wilder it drove me, the more he did it, along with deep penetrations as far as his cock would reach. We both came with huge eruptions and it took me quite a while to get hard enough to fuck him. I finally did and even though I couldn't quite seem to hit his prostate as often as he hit mine, he said he really enjoyed it.

He grinned and asked me, "Do you want to fuck again?" I just nodded agreement.

At the request of both of our parents, we alternatively spent our school breaks and vacations with each other, first at one parent's home and then the other's. Our parents continued to be delighted in our bonding with someone of the right "class" and, for once, we were in total agreement with them! We laughed secretly in the night at their notions that we were making friends of the right "class". If they only know just how close our relationship was becoming!

All the other guys at Groton probably thought we were two of the shyest guys they had ever seen. When we got undressed in the gym, we always faced our lockers to drop our pants, and in the showers we always faced the wall while we washed off and immediately wrapped ourselves in a big towel when we were through. In private, however, it was a different story! Charlie and I were totally uninhibited with each other and had been from day one. It was our usual habit to strip as soon as we got back to our room in the afternoon to begin studying and again at night after we had finished dinner. I remember one time when I was studying at my desk, Charlie came up to me with his limp cock dangling inches from my mouth and asked me to explain the theory behind a particularly difficult math problem he was working on. I grabbed his cock in my mouth and proceeded to give him a good suck!

He pulled his cock out of my mouth and said, "Randy! You know you can have that anytime but right now I really have to understand this problem or I am going to flunk the quiz tomorrow!"

I decided to be "good" and explained the concept behind the problem slowly and thoroughly until he understood it and went back to the sofa to continue to study on his own. I had noticed, however, that even after my brief sucking, his cock had grown from totally limp to half erect! I said to myself, "Man, you know how to turn Charlie on - you can get sex from that guy anytime you want it!" That was true, but the reverse was true too! All Charlie had to do was look at me, say "Drop your pants" and my pants were on the floor and I was bending over!

Why none of the guys at Groton didn't figure us out, I'll never know. Most of the guys spent their whole time there sexually frustrated, while we used to walk the halls with a smug look on our faces that should have been as obvious as if we had worn signs that said, "I got all the sex I wanted last night! Don't you wish you could have joined in?"

We grew closer and closer as the years slipped past and both wanted to attend college together to continue our relationship. Unfortunately, we were still totally dominated by our parents and Charlie was, in due course, shipped off to Harvard to become a lawyer while I was sent to Yale of major in Investments and Business Administration. Even our college majors and careers were mapped out for us!

We both vowed to keep in touch and to get together as frequently as we could. At first we did meet often at some out-of-the-way bed and breakfast mid-way between Boston and Hartford, but as we grew older and more mature, the visits became less and less frequent until they stopped altogether. Neither of us really understood why. As Charlie grew older he became more and more handsome in my eyes and his cock grew to a very respectable 8 inches! Every time he saw me, he remarked that I was sexier looking than the last time we had met - and yet we drifted apart! We remained very close friends but no longer thought of the other as our lover.

Neither of us found a lover in college although that didn't mean that we were chaste. We both played the field a lot and shared with each other (via e-mail) all the details about our sexual conquests. I had filled out very nicely since I had first met Charlie and now weighted 180#, was exactly 6' tall, had a very well developed and nicely muscled chest and a cock that had grown to about 8.5". All my sex partners said it was a "very suckable" cock and who was I to dispute them? I was also told that I had a great ass, very tight and extremely fuckable! I don't know about that, but I do know that I enjoyed fucking my sex partner for the night and he never complained about being less that fully satisfied with my work!

Eventually I graduated Phi Beta Kappa and cum laude, got a great offer from one of the big investment houses in lower Manhattan and started to pack to more there from Hart-ford. I'll have to admit that the offer was probably due more to my father's influence than to my own credentials, but I was determined to prove myself and not be thought of as merely "DeWinter's son". My parents, of course, wanted me to more back into the Brownstone with them but, for once, I fought them on this issue and said that living that far uptown while working in lower Manhattan would be too difficult and that I wanted a place of my own. Reluctantly they relented.

About this time, a friend of mine at Yale told me about a guy in NYC he knew slightly, who had just graduated from NYCC. The guy was starting a career in banking and was also looking for someone with whom he could share an apartment in lower Manhattan. My friend acknowledged that he didn't know the guy ver well but that his impression was that he was a laid-back easygoing kind of a guy with whom I might get along very well. He added that he had heard that the guy's father was also into banking - a fact that would probably impress my family. I told him I would check him out during my next visit to New York.

I called the guy at the number my friend had given me and liked the sound of his voice right off. His name was Robbie Lamont and we agreed that it would be a good idea for us to meet to see what we thought of each other before making any final decision. We arranged to get together for drinks that night and maybe dinner as well if everything worked out. Robbie turned out to be an almost duplicate of me with regard to build, height and weight. He had brown curly hair, dark brown eyes and a somewhat darker complexion than mine. He was handsome, but not beautiful, and I took to him right away,

We got along so well over drinks that we went to dinner together and then spent the next couple of hours just talking and getting better acquainted. I couldn't figure out if he was gay or not, but I liked him enough that it didn't seem to matter. I agreed to go with him tomorrow to look at an apartment that he had tentatively picked out but didn't think he could afford if he had to pay the entire rent. It turned out that I liked the place as much as he had and agreed that it was very convenient to where we both were going to work. I found out that afternoon that he was going to be a teller in the bank, not a manager, and that his father was also a teller at one of the bank's mid-town branches.

I knew my parents wouldn't like to hear all that; but Robbie was a nice guy whom I liked a lot and I intended to move in with him regardless of that my parents thought! We spend the rest of the week shopping for furniture where I had to take into account his limited budget. The apartment only had one bedroom and Robbie shyly asked me if I would mind sharing it with him. I told him that I had roomed with other guys for the last seven years and that, if he didn't snore TOO loudly, I was pretty sure we could get along. He grinned, but we wound up getting twin beds rather than the king-size one I had hoped for, but had been reluctant to mention for fear of spooking him.

The first night we spent together, I didn't go into the bedroom until Robbie had already gotten undressed and was sitting on the side of his bed in his shorts, facing my bed. At that point I went into the bedroom and quickly stripped making sure that my sock was in clear view. I stood there a few seconds as if I was trying to make up my mind to sleep in the nude or put my shorts back on. Although I didn't look directly at Robbie, I knew he was watching me closely and had let out a little gasp when he saw my cock dangling almost within his reach. After he got a good look at my cock, I turned around and bent over to pick my shorts up from the floor. In doing so I made sure he also got a good look at my ass and asshole! When I got my shorts back on, I climbed into my bed without a word, turned off the light on the nightstand between us and tried to get to sleep. It took a long time to fall asleep and I'm sure Robbie was awake as long as I was!

The next morning, we took turns using the bathroom to shower, shave and brush our teeth. We didn't say much to each other but just got dressed and left for work. It turned out that it was a good day for both of us and we got home at about the same time in very good spirits. I got each of us a cold beer out of the 'fridge and we sat on the sofa as we drank them. I told Robbie that I had such a good day at work that I wanted to take him out to dinner to celebrate with me. He fussed a little that he wanted to pay his own way, but eventually graciously agreed to let me treat him.

I took him to a really nice restaurant that was nearby and told him I was going to order for both of us. I did that primarily to keep him from seeing the prices on the menu! I had found out that Robbie liked pretty plain food - nothing exotic or fancy, so he was pretty easy to order for. As I told the waiter each item I was ordering for him, I would glance at him and he would nod slightly to let me know that my choice was fine. I quickly ordered for myself and also ordered a bottle of an excellent Merlot that I knew this restaurant stocked.

Robbie enjoyed his dinner immensely and drank more than half the bottle of wine. By the time we left, he was a little wobbly on his feet and more than once I had to put my arm around his shoulders to steady him. As we walked home, however, Robbie became more and more quiet. I could tell that he had something to tell me, but didn't know how to do it. My guess (and hope) was that he was going to tell me he was gay and I intended to do everything I could to help him make that "confession"! When we got back to the apartment, he thanked me for a great dinner, sank down on the sofa and just stared at the floor. I told him that I could tell he had something to tell me and that he should go ahead and get it over with.

"Randy, I should have told you this when we first me, but I wanted you as a roommate so much that I afraid of frightening you off!" He looked at the floor some more and then blurted out, "Randy", I'm gay and if you want to move out, I'll understand!"

I told him to stand up. I think he expected me to hit him and just stood there waiting for the blow. He was more than a little surprised when I laughed, threw my arms around him and whispered in his ear, "Buddy, I'm just as gay as you are, if not more so, and I find you far more attractive sexually than anyone else that I have met in a LONG time!"

I thought for a few minutes that Robbie was going to cry, but he finally said, "Oh man, you don't know how happy that makes me! When I saw your cock dangling in front of me last night it took every ounce of will power that I had not to grab you, throw you to the floor and rape you on the spot!" I laughed again and said I doubted if he could rape me.

"I'm a lot stronger than I look!"

"No, Robbie, I don't doubt that - what I meant was that you can't rape someone who is perfectly willing to have sex with you!"

We both rushed into the bedroom, tore off our clothes in record time and fell onto one of the single beds. At first, we just hugged and exchanged deep wet kisses, but Robbie finally said, "Man, I can't wait a second more. I want to suck that cock of yours!" He quickly swung himself around and started to suck my cock at a furious clip. He was an expert at deep throating and shoved my cock so far down his throat that hie lips were buried in my pubic hair. Every so often he would pull back and concentrate on my cockhead, licking and sucking it until I thought I would go out of my mind! Needless to say, I reciprocated fully and loved the feel of his cock as I engulfed it. Quicker than either of us wanted, we both exploded in each other's mouth as we sucked the other dry.

When we were both limp again, Robbie finally released my cock, looked at me, smiled and said, "Man, you can feed me as much of your cum as you want. I loved it!"

I grinned back at him. "That goes double with me!"

As soon as we were able to get each other erect again, we started to experiment with fucking each other to see if we enjoyed that as much as we had the 69ing. It turned out that we each agreed that the other gave a very superior fuck and that neither of us had any difficulty in taking the other's cock up our ass as far as it would go!

We quickly concluded that we had each found a lover who satisfied us fully from a sexual standpoint but, even more importantly, whose company we enjoyed and with whom it was easy to live. I told Robbie that the first thing we had to do next weekend was to get rid of these damned single beds and get the biggest king-size bed we could find. Robbie agreed!

Of course, Charlie, who had filled out as nicely as I, had to fly down from Boston to check Robbie out and make sure that I wasn't making a terrible mistake. Even though we had not been lovers for years, we still considered each other to be our "best friend" (in my case, next to Robbie, of course) and we probably always will. I guess there is some-thing to the old saying that one never forgets one's first love!

Robbie was a little apprehensive about meeting Charlie for the first time, but it turned out great! The both took to each right away and after talking privately with Robbie for about an hour, Charlie came up to me gave his full approval to the relationship. His words were that "Robbie was a keeper!" Charlie stayed the night and Robbie shyly asked him if he would like to share the king-size bed with us. Charlie laughed but declined and said he would be fine on the sofa. The next morning he was on his way back to Boston. Later on that year when he found Roy, Robbie and I had to go up to Boston to check out Charlie's new lover. All four of us hit it off immediately and for years thereafter we would all take cruises or vacation together!

Every weekend we visited either Robbie's parents or mine. I had never told my parents that I was gay probably under the theory that what they didn't know wouldn't hurt them and it would just avoid another confrontation) although I could never understand why they hadn't figured it out on their own. They certainly were not naive but I guess in their arrogance they just assumed that it was impossible for a DeWinter to be of those despi-cable gay creatures. Robbie had told his parents that he was gay when he was in high school so they both accepted us for what we were and were delighted that Robbie had found a "companion" who was such a "nice boy". We usually visited his parents with about twice the regularity as we did mine in that we both felt at home with them while the atmosphere in the Brownstone was always stiff and formal.

The rest of our weekdays were all spent pretty much the same - work during the day, a wind-down hour at out apartment while we drank an ice cold beer and told each other of our day's activities, dinner either alone or with friends at either a nearby restaurant or at home. If we hadn't eaten with friends we usually spent an hour or so after dinner just talking together about topics of mutual interest. Day on weekends and holidays differed only in that we would visit his or my parents, get together with some friends to explore one or more of the City's many museums, occasionally take in a Broadway show's matinee or just take long walks in Central Park. Our evenings were almost always the same regardless of whether it was a weekday or a weekend. We usually went to bed quite early, not because we intended to go to sleep, but because that was the start of our "fun time"! Whether we sucked and/or fucked, the sex was always great and left both of us fully satisfied. After making love, we would quickly shower, get back in bed and fall asleep in each other's arms. Just before we would drop off to sleep we would whisper to the other such things as "God, do I love you!" or "You make me happier than I ever thought could be possible!" What a great way to fall asleep - totally satisfied sexually and knowing that your partner really loves you!

One other little habit we had was to give each other a full-body massage every so often. Although neither of us really knew how to give a professional massage, I had visited a massage therapist a couple of times while I was at Yale and remembered much of his technique, which I also taught to Robbie. We both loved being massaged by the other, but I think the one giving the massage got the greatest pleasure in that he got to use his hands to stroke, rub, caress and massage the body of his lover for as long as he liked! We used mildly aromatic oil for the massage and when we were through both of us were as slick as wet seals and gave off an aroma that filled the room. Fun time usually followed one of these massages which made for some interesting sex with out bodies as slick as they were!

This life continued until I was just shy of my 32nd birthday. That's when the sky fell in on me. My parents had decided a few weeks before to take a brief vacation at one of the luxury resorts on a little island off the coast of Georgia. They had invited Robbie and me to go along, but we had to decline. They never understood that Robbie's position with the bank was not one where he could suddenly and arbitrarily take off from work whenever he felt like it. They chartered a jet to fly them down to the island and Robbie and I went to LaGuardia to see them off. The last image I have of them was of their standing the doorway of the plane, facing us and waving. Because this was not a scheduled flight, all they had to do was get permission from the air traffic controller to use one of the runways and away they went.

We hadn't been back home for more than a couple of hours when I got a phone call saying that the plane had apparently gone down off the coast of North Carolina. They were searching for wreckage now, but didn't expect to find any survivors. The crash was apparently a big mystery in that no one on the ground, or any of the air traffic controllers, actually saw the plane go down. Also, the jet had just had a major inspection the day before and had checked out perfectly. In addition, both of the pilots were very experienced and neither had radioed any message of trouble. The plane had just disappeared. The only conclusion that the officials could reach was that there had been a massive explosion aboard the aircraft while it was in the air.

I was questioned at length on such subjects as who had packed their baggage, how did they get to the airport, who handled their luggage, did they have any enemies, was I the only heir, etc. Nothing fur developed, however, and the investigation eventually petered out as "unsolved".

Charlie and Roy were down with us the next day and stayed until after the Memorial Service we held for my parents. The Services were held in the city's Episcopal Cathedral that my parents had attended for as long as I can remember. The Archbishop of the Diocese conducted the service and several of my parents' closest friends gave eulogies. The church, huge as it is, was barely able to hold the crowd that attended. Scores of my parents' brothers, sisters, nieces, nephews, cousins and old family friends from Virginia made the trip up and hundreds and hundreds of their friends from the New York area also showed up. It was a beautiful service but I was relieved when it was over and the last guest had passed through the receiving line.

Robbie, Charlie, Roy and I made our way back to the apartment and sat around making small talk until it was time to go to dinner. Charlie and Roy said they had to get back to Boston the next day, but assured me that if I needed them at any time they would be back in a flash.

Robbie and I made love that night, for the first time since my parents had died, and it was with a gentleness and tenderness that was unusual for us. We were usually so hot for each other's body that there was a sense of almost frenzy or desperateness to our love making, but not that night. Our sex making was slow, leisurely and far more an expression of our love for each other than sheer physical attraction.

The next night after work, Robbie and I sat next to each other on our sofa and slowly sipped a beer together. Robbie rested his hand on my knee and every so often gave it a squeeze as if to assure me that he was there for me in any way I needed.

Suddenly a thought struck me that had not occurred to me before. It was so intense a shock that my whole body jerked and Robbie threw his arms around me and asked what was wrong.

I stared at him for a minute and then said, "Robbie, you know I loved my parents but you also know that they tried their best to dominate me and make every importance decision for me since the day I was born. It just struck me. They are gone and for once I can make all my own decisions without having to worry whether or not they will approve. I know it sounds horrible, but the only thing I can think of are those famous words that Martin Luther King said.

Robbie asked, "What words are those, lover?"

I thought for a moment and then said, "Free at Last! Thank God, Free at Last!"

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