This Story Is Sponsored By MatureGayDVDs.com

  • The yuppie sex chronicles

    • September 30th, 1980

    At two in the morning, I brought forty-seven year old Gary home after meeting him at a coffee shop. He possessed a strong broad chest from working construction, and years of weightlifting gave his appendages a stocky appearance. After removing all of our clothes, Gary reclined on my leather sofa. By his calm composure, I could tell that Gary was accustomed to being serviced, and he was waiting for me to make the first move. He had a sly grin under his red mustache, and his green eyes were as mysterious as those of a sheik. By his body language, I could tell that Gary was a top, and the fact that I'm a younger guy only confirms my assumption. Still, that did not matter to me because I was going to have him one way or another. I directed him to my bedroom, and he stretched himself out on his back. I encouraged him to lift up his legs so that I could bathe him with my tongue. His hairy torso folded over with muscle as his hips lifted from the bed. I dove into him, and he groaned with ecstasy. Ten minutes later, Gary had an enormous erection, and his entire body was growing increasingly hot. While oiling my finger with lubricant, I asked him if he ever had somebody insert a finger in his anus. He shook his head in disapproval, and claimed that he only liked to be rimmed. As he answered me in his Irish brogue, I swiftly inserted my long digit inside him. For a moment, Gary tightened up, and he started squirming uncomfortably. Before Gary could get up, I immediately started stroking his stiff penis, and he was overcome by my pacification. Eventually, I convinced him to allow me to insert another finger. Then, after going down on Gary for a while, I persuaded him to let me penetrate. It was an incredible feeling to slide inch by inch inside of him. His orifice secured a firm grip, and Gary's slippery rectum seemed to curve to the shape of my penis. Both of his legs were fanning in the air, and he had a look of sweet agony on his face. When I was going for the long stretch, Gary's crimson face grimaced as his own body simultaneously exploded with orgasm.

    October 1st, 1980

    While grabbing a late dinner on Wall Street, I happened to run into an old buddy of mine. Trevor Hernandez was approximately twenty years older than I was, and he had worked for the same stock company at which I am employed. We had slept together only once before, and that experience was mind-blowing. After dinner, Trevor seemed genuine when he insisted that we have a platonic drink at his penthouse. Once we got through the front door, though, Trevor and I became consumed with fiery passion. As I tore Trevor's shirt and tie from his body, I noticed that he had grown a little soft around the midsection. I could still make out a six-pack, but a layer of fat surrounded it. This really turned me on because it gave Trevor a much more masculine look. Trevor had always looked so trim and boyish before, but now he appeared huskier. While we were French kissing, I unbuttoned Trevor's expensive slacks, and let them fall to his ankles. I dropped to my knees and pulled down Trevor's silk boxer shorts. I hungrily drank his member--like expensive Dom Perignon--until my nose was buried in his blond pubes. He bucked his hips, and rested his hands on my shoulders for balance. Trevor started breathing intensely, and he begged me to release him. He started trying to push my face from his groin, but all it did was make my open shirt brush against his ankles more vigorously. How could I possibly stop? The musky odor emanating from his pubic hair only made me suck harder. Succumbing to my friction, Trevor began screaming my name (in a Spanish accent) as he released his seed into my torrid mouth. The evening ended gloriously on Trevor's couch. Trevor's face was pressed against a sofa cushion, and his buttocks were held high in the air (pants still around the ankles). As I slid my hard penis into his pink, hairy anus, the scent of dry-cleaned clothes simmered off of his clammy brown flesh.

    October 5th, 1980

    I balanced my weight on all fours while Derek Takamoto was thrusting into my backside. It had seemed like a tedious evening beforehand. I had circled the bathhouse three times by midnight, and there did not seem to be any good candidates. Then I came upon bookish Derek who was sitting with his legs crossed like a virgin. Derek looked to be a thin man in his late thirties-- with almost no body hair except for the sparse wilderness that decorated his lower abdomen. After befriending him, I found out that it was Derek's first visit to the bathhouse. In fact, Derek claimed that he had yet to sleep with a man, and the bathhouse seemed like the right place to go. So, I took it upon myself to be his patient teacher. After teaching him a few moves, I started questioning whether or not Derek was actually telling the truth. He took well to kissing, for his lips were wet and tender. Derek plucked my erogenous zones like a guitar player. I took his erect nipple in my mouth as he placed his hand between my buttocks. I bit down on Derek's earlobe, and his body convulsed electrically. I could not bear the heat any longer. Taking a tube of lubricant from a shelf under the bench, I told Derek to massage my anus with his finger. He did this eagerly, and I could see that Derek was enjoying the experience. I looked down between my knees to see that his penis waved frantically in the air. My excitement overtook me, and I started backing myself into Derek's crotch. At first, he did not know what I was doing. But, when he started feeling his penis being devoured by my aperture, Derek must have got the hint. He wrapped his arms around my waist, and thrust forward with a loud cry. Throughout our encounter, I continued pushing against his pubic region. After ejaculation, Derek's body seemed to be more accommodating and elastic. Standing in a bent position, Derek had to hold onto my lower legs just to keep himself from falling over. Beads of sweat journeyed down his spine as his entire body jerked with my long, deep thrusts.

    October 12th, 1980, 4 PM

    There have been no adventures since my steamy hour with Derek. Although, the intern Raymond might be giving me the lovesick eye. He looks to be in his mid-twenties like me, and there's never a day when I don't see him pass by my office. Sometimes Raymond delivers a message to me from the main boss, and we both blush like Catholic schoolboys. We've been doing this for the last six months. As a sit here writing this entry, I find myself hoping that Raymond will deliver some message to me, but he has passed by only once today. I want to just ask him out on a date, but I'm afraid that he might not be gay. My work shift is officially over, but I'm still waiting for him to come by. I know I would enjoy having sex with Raymond, but I'm questioning if that would be a good idea. Instead of sleeping with him on the first date, I want to know more about him. The thought scares me because I've never felt this way for anyone. I hope I'm not falling in love.

    October 13th, 1980

    Would you like to know why I enjoy seducing older men so much? It's definitely not because I think older men can teach me how to be a better lover. Nor is it because I am desperately grasping for a father figure. If you theorized that I do it for financial reasons, you are wrong once again. I don't bed older men as a challenge, either. In truth, older men are much easier to get in the sack than younger guys. I can charm the low-cut briefs off any man over forty. The only challenging aspect of "getting" older men is to convert the long-established tops into bottoms. Most older tops are as timid as virgins; that is, when I have them lying face down for me. There's nothing more satisfying than chaining a middle-aged man to a wall, and whipping him until he begs for mercy. There was this one time when I had a buff fifty-five-year-old man lick my boots. His hands were tied firmly behind his back. He slobbered all over the leather sniffing the fresh semen that coated my shoelaces after he climaxed. I militarily demanded that he lick all of his seminal fluids off. Then, I pumped him until his bald head was flushed deep vermilion.

    Shall I describe what I like so much about older men? Why I prefer them to men my age? To put it simply, I love their hairy posteriors. I especially enjoy it when my "love muscle" is thrusting between those hairy cheeks. Older men groan from the gut like large bears. Most often, my giant hands are lost in a tangle of back hair. My soft, muscular thighs rubbing against the backs of their bushy, firm legs. Ordering every guy to scream my name after I bark, "Who's your son?" several times, all of this happening before I lose myself inside of them.

    Most of the tops are really tight, for very obvious reasons. Even though it may sound ridiculous, I consider the older tops who haven't been penetrated to still be innocent. Sure, they've shared their seed with plenty of men, but not all can truly "take it" like a man. So, what's my secret for seducing tops? I can't explain how I do it. Some trust me so much that they hop on my bed and automatically stick their butts in the air.

    There was this empty-headed guy who didn't even know my penis was inside of him until I rippled with orgasm. I was fingering him, and it got me really turned on. He was lying on his side, so I just pushed my flushed member in like a true maestro. The man was convulsing in pleasure, complimenting me on how large my fingers were. Funny guy. He did not seem all that angry when he actually found out the truth. For the next few days, my answering machine was filled by his calls, begging me to invite him over again.

    Other guys are not so easy. About two weeks ago, I needed to finger this Irish guy I became acquainted with before penetration could happen. Some older men are comfortable only after I rim them (while switching back and forth to fellatio) for approximately half an hour. They feel my tongue penetrating their pink orifices so they naturally get curious. Of course, a firm erection feels much different than a tongue. By the time the men find out, though, I'm already grinding against their prostates. Do I allow myself to be penetrated by older men? Yes, but not very often. I enjoy entering older men too much. If I do allow myself to be penetrated, it's usually because my semen is simultaneously seeping out of them.

    Anyhow, I think I've had my fill of older men. It's time I try dating someone close to my age. Not having a one-night stand, mind you, but actually a real date. This is not such an easy task for me. I usually find a man, take him home and have my way with him. But, ever since I've laid eyes on that cute intern Raymond, I really don't know how to conduct myself. Whenever he is in my presence, I feel completely insecure, and that definitely worries me. As of yet, I still do not know which way he swings. Nevertheless, I will keep trying to get something out of him. If anything develops, I'll be sure to record my misadventures. Naughty thoughts of Raymond got me so riled up that I needed to take a cold shower. I've been sitting here only wrapped in a towel, and I am freezing. I'd better put on some snug boxer shorts.

    November 23, 1981

    I suppose an explanation is in order. I haven't written anything down for almost a year. From what I gather, I was completely infatuated with an intern named Raymond. Well, time really does fly when you're having funor at least before it dissipates into total monotony. But enough with the apologies already! Here are the complete details.

    The intern eventually changed into a part-time employee. As I said before, Raymond is slightly younger then me, an incredible departure from my usual choice of older sex partners. What can I say? The guy roped me in with his jet-black hair, green eyes, Catholic schoolboy demeanor, and well-proportioned body. At first it didn't even matter that his skin was smooth and luminescent, that all of his hair glistened in wave after wave of curl, that his long torso remained tucked in youthful and muscular splendor. I had no trouble conversing with him on dates. We listened to the same kinds of music. We were familiar with the same types of films. I didn't mind that Raymond and I were almost identical to each other, based on our similar ages and backgrounds. I liked how everything seemed like a new discovery to him, partly because he did just graduate from college (he was the quintessential sacrificial lamb that wolves are akin to).

    Sex was awesome in the beginning. It was a treat lying on top of another smooth body, sliding my throbbing dick into a firm and hairless asshole. He was inexperienced all right, having been with only two men prior to me. I was so intrigued with his relative virginity that I allowed him to fuck me as well. His short dick was compensated by girth, and I would spread my cheeks to the fullest before sitting on it (even though I knew that my asshole would still be tight around his cock). I was the first guy that he ever penetrated, and I made it worthwhile by riding his dick to headboard heaven. It was so good that when he came, Raymond would still lie there (with his mouth wide open for two minutes straight) until the ripples in his hips subsided. Because of his youth and previous college stint as a gymnast, Raymond was incredibly flexible. We fucked in positions that I didn't believe were possible. My favorite one was Raymond in a handstand, with his split legs in the air. I would come so much that the semen would spill down both his chest and back. Raymond was also a bit lighter than me in weight, enough for me to pick him up. I used to fuck him against the shower wall, pumping him so hard the tiles would shake.

    I can't tell you when things started changing for me. It couldn't have been when his job status changed. I've had no real qualms about fucking new or former co-workers before. We still had some great conversations, and I felt very comfortable sharing my ideas and plans with Raymond. For a while there, I thought about introducing him to my parents, as the so-called "friend" of course. I remember watching him sleep one night, wondering why I felt so much emptiness for a guy that seemed almost perfect to me. When we would go out, though, I felt my eye wandering around. There was a need that Raymond could not fulfill in me, something that bordered around wanting absolute dominance. When we would fuck, I felt that he was not as grateful, like in the beginning. His inexperience and versatility, while having some positive benefits, did not have the stubbornness that I lusted after in my older sex partners. He was not set in his ways. There wasn't a long-established top to conquer. Raymond's body was way too tight for me after while. When I would slap his ass in the doggie-style position, nothing would jigglenot even the sheer muscularity was disturbed. His ass was smooth without even the slightest down of hair (no wrinkles were there either). Monotony started setting in. I felt like I was fucking the lightweight instead of the heavyweight champion. I kept imagining my sweaty chest against a furry back, putting my hand underneath a rough and bristly chin as I place a wet tongue in a velvety ear. The fact that Raymond couldn't even grow a mustache or beard made all my hopes crumble. I could no longer have a romantic relationship with Raymond anymore.

    Raymond seemed to take it well, but I knew that he had developed some strong feelings for me. Before I broke it off with him, Raymond would cry out during sex how much he loved me, and it would always make me feel too guilty to finish performing. When we slept together for the last time (it was pity sex on my part), I wanted to be cold and distant but ended up being slow and gentle. When he came inside of me, Raymond's eyes were shut tight, and he appeared in such a trancelike bliss that I thought he might never get off of me. After awhile, he kissed me on the forehead, and then withdrew his dick. I felt obliged to let him stay the entire night, but Raymond insisted on leaving. He left his spare key on the dresser, and said with feigned cheerfulness "I'll see you around sometime." I didn't really know what to say, but a simple "yeah definitely." When the door shut behind him, I felt that familiar emptiness again, and I wondered if I had made the right decision.

    With the continual shifting at the office, I didn't see Raymond for a while. It was not until two months after the breakup that I actually ran into him. We conversed naturally, and it seemed like there were no hard feelings between us. He still looked better than ever, and he had just started working for another sector of the corporation. Raymond was so ecstatic about it that he asked me if I wanted to have dinner with him. I had some apprehensions about the situation, but I figured it would be rude to turn down his offer. Besides, I had missed his companionship.

    In the restaurant, we were having an enjoyable ex-lovers meal (at least in my eyes) when suddenly my nose began twitching. There was this incredible aroma invading my senses, a combination of cologne and sexual energy merged into one. I turned just as Raymond began talking about politics, when before my eyes were the most gorgeous man I had even seen standing by the bar. He was not as good-looking as Raymond, but he could have been a dead ringer had Raymond been twenty-six years older. This man was at least 6' 4", with the same dark features that attracted me to Raymond. His green eyes still glowed underneath thick arched eyebrows, locked in a sexy fierce look punctuated by the deep wrinkles in between. He had an olive complexion with a generous amount of wrinkles. The man had a thick mustache and an afternoon shadow on his square jaw that drove me insane. Even though his hair was thinning, you could still see traces of waviness accentuated by salt and pepper streaks. He looked like a former football player, with a monstrous upper torso that boasted a chest at least the span of a Cadillac hood. His abdomen had a little bit of gut sticking out, through the firm sides were still contoured by a fitted white sweater. His biceps popped out tremendously, arms stocky and hairy, the skin looking coarse yet fresh. The lower body was my absolute favorite. The legs looked thick and shapelythis was definitely a man that kept in great shape. He had slightly full hips, hugged generously by black slacks that enveloped my favorite part of any man: the waist.

    By now, I had made an adequate survey of the man's features, but I hadn't looked at his ass yet. I turned back to an unsuspecting Raymond (who was wholly interested in his conversation topic), keeping the man in my peripheral vision. Raymond excused himself to use the restroom, and I now had the chance to look at the man again. He was leaning against the bar, and let me tell you, I almost came in my pants when I saw what stood before me. His ass looked like two luscious cantaloupes. It was not firm and young like Raymond's. In fact, they jiggled in those black slacks. I wanted his ass, and I was ready to do just about anything for it. From what I gathered by the man's conversation with the barkeeper, he seemed like a regular. When I looked at him again, I saw that he had already finished two shots of Jack Daniels. The barkeeper and he were laughing about this year's sports statistics, when he looked at my direction midway. I think he felt my eyes devouring his amazing body. He looked at me, smiled, and winked. At that moment, I knew he was going to be mine.

    November 30, 1981

    Blindfolded, laying spread-eagle on satin sheets. I barely bottom for another man, but occasions like these require special attentionand I am more than willing to bestow it tonight. Not having sex for the last few months made me feel like a virgin again. I need another "first time," and he is definitely man enough to do it.

    "Lick it baby, lick it!" I exclaim, as he opens my butt hole and plunges in. My dick tingles, growing an instant hard-on. Rolling his tongue in circles, I groan as his bushy mustache pricks my sensitive asshole. He then rubs his thick beard against my balls, proudly greeting my heavy moans with "yeah, you like that shit don't you?" He kisses my dickhead, giving it a nice wet smack. Tonguing my piss hole, he licks all my precum instantly, servicing like the experienced old man he is. By his body language, I know he enjoys watching my legs quake in total submission, running his giant rough hands along the soft flesh of my left thigh. "Do it now. Oh fuck, do it!" I yell, opening my legs as wide as possible. He chuckles heartily, and slaps his hands on each butt cheek. "Here comes a special surprise. Open wide now, like the good virgin you are" he commands, simultaneously sticking his thick cock in my tiny hole. I gasp from its immensity.

    He's not gentle. I grow breathless as he puts his full body weight on top of me, pressing his hairy chest forcibly against mine. He bangs my asshole, thrusting his slippery dick in and out like a madman. "Oh baby, your ass, oh. Milk my cock, baby, milk all my cum" he screams, as I tighten my asshole around his love muscle. I bury my hands in his nipple hairs, pulling them as he pounds away. From his body heat, I am guessing he's dark red, huffing and puffing for what seems like hours. Up until now, I don't think I've ever truly enjoyed an older man butt-fucking me like this. His crazy thrusts start slowing down. I know he's ready to dump his load now. "Here it comes, you nasty little fucker. I know you've been wanting this all night" he says. I reply breathlessly with "Deeper, deeper, oh daddy, fuck the shit out of me!" He pushes as hard as he can, judging by how tight his abdomen feels against my hand. "Oh shit, oh shit, oh shit, yesssssssss, yesssssssss, ohhhhhhhhhhhhhhhhhhh!" He squirts his creamy load in ecstasy, holding his swollen dick inside. He collapses in my embrace, receiving nothing but kisses and strokes in his hair.

    It's my turn now. He leans against the wall, face pressed eagerly against the surface. I spread his humongous ass cheeks, savoring the buttery and spicy aroma that emanates from its pink center. By his tensing muscles, I could tell that his breathing increased tenfold. I feel a sweat bead trailing down his blackened crack, continuing onto his burgundy balls. The nut sac, sagged a little with age, holds two amazing plum-like balls that pulsate with each fondle. I rub my nose against the coarse gray hairs that populate his sweet olive cantaloupesall standing on edge with my slow deliberate puffs of air. His weathered skin probably turns vermillion underneath my firm fingertips, as I drive his hips further into the wall. My hard dick drips precum again.

    I lick his nut sac all the way up to the soft tissue underneath his ass cheeks. "Ah yeah!" he exclaims, pounding his fist enthusiastically against the wall, "Oh shit that felt so goooooddd! Whew!" Even though he is experienced, I know he is not expecting what will come tonight. "You're going to have to relax for me now, daddy. I know it's been a long time since you've been ass fucked, but I guarantee you won't be sorry. But before I do that, I'm going to give you a little bath." I massage the tender skin around his asshole, squeaky clean from the hot shower he took earlier, satisfied with the gleeful "Ohhhhhh" coming from his mouth. My tongue traces the puffy skin surrounding his asshole, taking my sweet time with the old man. I'm going to tease the hell out of this fucker. He starts breathing harder, blowing enough to put out a thousand candles. I straighten my tongue, aiming it at the tender asshole pulled apart by my fingers. Ready, aim, fire!

    "AHHHHHHH!" he exclaims. My tongue moves in and out, in and out, in and out. "Push, baby, pushohhhh shit!" he groans between pumps. I circle repeatedly, wetting the salty thin tissue inside from top to bottom. Midway, he bends completely over, screaming like a deranged Tarzan. I couldn't wait to fuck him, so I reach for the lube earlier than expected.

    His manly funk stimulates my nostrils, the side of my face sticking to the back of his perspiring head. I fuck him deep and hard, hammering his furry body against the mattress. The sweat between us makes a wonderful slapping sound, like floured hands pounding against soft dough. Like a bear in extreme heat, I show him no mercy whatsoever. "Ohhhh, ohhhhh, shit, oh shit, fuck, fuck, fuck, fuck, ohhhhh fuck!" he screams, as I increase my speed. For a moment, I imagine how our reflections look in the dresser mirror. His flushed and sweaty face probably looks angry, as if he didn't enjoy being topped by a younger man. His eyes must be clenched shut, teeth gritting, nostrils flaring above his thick salt and pepper mustache. He was certainly taking it up the ass like a real man. I don't really care, though, because his ass is completely mine.

    By the rustling sounds, I am guessing that he just grabbed the bed sheets in his gigantic hands, his large elbows imprinted in the mattress. I grunt like a grizzly, and use my body to push his flat on the mattress. A large pillow is underneath his husky body. Before mounting him, I envision his large ass cheeks looking like scoops of succulent butter pecan (especially in the soft beige light)my cock like a hot spoon diving in between. Now his chin is probably resting on top of the mattress, the scent of sweat emanates from the sheets. I want to fuck him in all kinds of positions, but having him face down is the best. Besides, my cock feels sore from all the grinding. His ass will swallow my spunk pretty soon. "Yeah daddy, I got a little surprise for you as well. Ooooh yeah, ooooohhhh yeah. I know you want it. I got a nice creamy load for you, straight from the heart." I squeeze his cheeks with my large hands, slapping his asshole hard. "Say it, say it daddy!" I exclaim. "Oh, oh, oh, yeah, do it son, give daddy all your sweet cum," he puffs through hot sweaty breaths. I explode inside of him, screaming "ah shitttttttttt!!!!!!!," feeling all my muscles spasm like aftershocks. It was one of the best fucks I ever had.

    "How was I?" Raymond asks, as I lay beside him after dismounting.

    "You were fantastic," I say, removing the blindfold, "With all that dirty talk, I really thought you were the guy by the bar."

    "I was that great! I'm flattered enough to go another round." Raymond says, flashing his most devilish smile.

    "All right," I say, "But this time, I want to be the dirty old man." We pull the satin sheets over us, laughing at our horny selves. I'm glad we got back together.


    Please take the time to rate the story and dont forget to visit our sponsor - They are keeping the site free for everyone!

    Current Rating:




    This Story Is Sponsored By MatureGayDVDs.com