Wayward Island (Part 3) How Randy Popped Jake's Cherry By Jake Preston
Reader restrictions: no minors, no readers who are offended by explicit descriptions of gay sexuality. The story as a whole is a psychological study of gay athletic hunks who love nerds, and the nerds who love them in return. The story also deals with the problems faced by gay guys who live in rural areas. If these themes don't interest you, there are many other great "nifty" stories to choose from. All characters are fictional and are not based on real persons. Most place- names are fictional, too. Send comments and suggestions to jemtling@gmail.com. Jake will respond to all sincere correspondents. Please consider supporting "Nifty Stories" with a donation! To learn how, click "Donate" in the index heading.
Snowflakes brightened my windshield in the fading dusk as I drove up the dirt road toward the cabin. Randy sat beside me the Chevy, with one hand on my leg. Fluffy wet flakes crawled like the ghosts of giant caterpillars on the bare branches of birches. The evergreens --- splendid Norway pines, white pines, spruce, and balsam - many shades of green in daylight --- under the weight of snow merged into an abstraction of greenness. The birds of winter, too - chickadees, sparrows, bluejays, cardinals - merged into an abstraction of birdiness --- their harmony interrupted by the intrusion of an unwelcome squirrel. They gathered around the bird-feeders that I maintained near the cabin. "I get lots of hummingbirds, too," I said, "but they're basking in sunny Mexico by now."
I took Randy on a tour of the grounds. We walked around the cabin, and down the hill to the lake. It was partially iced over, but dotted with wet spots that darkened at dusk. I showed him my sauna, adjacent to the dock. Opposite the sauna near the dock, and ancient cypress arched over the beach, its sands now invisible under the ice. "I have to replenish the sand every year," I explained to Randy. "Otherwise, the muck keeps coming back. Your uncle Tom loans me his truck. I get sand from a gravel pit near my farm, and dump a new supply of sand over the beach in January or February."
Behind the sauna, two boats and a canoe were wrapped in tarp for winter. I mentioned that we could fire up the sauna after dinner. I felt Randy's hand on my butt, a gesture of familiarity. I showed him my workshop (as I called it), a partitioned building with an ice house on one side, and a room for fish-cleaning and deer-breaking on the other. A woodshed was attached to one side of the workshop. It was really just a roof on stilts, stocked with enough wood to last through spring. We each carried an armful of wood to the cabin.
It was chilly. A fire in the hearth, and another in the Franklin stove, warmed up the "great room." The stove is centered between the kitchen and the living room, which includes space for a study. We climbed the stairs led to the loft, which overlooks the fireplace. I kept my books in the loft, and a desk with a second computer. Why two studies, why two desks, why so many books, Randy wondered. "I'm a writer," I reminded him. "That's how I make my living."
Back on first floor, I showed Randy two rooms at the back: my bedroom, and a utility room with a washer and dryer. The bathroom took up about half the space of the utility room. A hallway between them led to a large screened-in porch. The hallway was closed for the winter. "When I bought the cabin, it had an outdoor toilet," I explained. "When I built the bathroom, there wasn't enough space for a tub, so I installed a shower instead. It's got only one spigot, but plenty of space for two men to fool around in."
I stated heating chili on the stove, and opened a bottle of cabernet. We downed a glass of wine and started another. "It's a romantic setting, Jake. The cabin is 'you' --- unassuming and comfortable, and maybe a little apprehensive," Randy said. He smiled slyly and added: "a fitting place for you to lose your cherry."
"One of us has to sacrifice his ass," I said, repeating one of Randy's lines. Talk after dinner; conclusion foregone.
Randy tried to insert his hand down the back of my jeans. He didn't get far. He unbuckled my belt and tugged. It slid though the loops. He held it up dramatically, and tossed it to the floor. "No more chastity belt," he said. "No more protection from the big bad wolf." He slid his hand down my jeans, and wiggled past the band of my jockey shorts. He fondled my butt, as much of it as he could reach. His fingers slid into my crack. He pushed his hand down forcefully, until his fingers reached my asshole. We kissed while his fingers wiggled over my virgin cherry.
"Looks like Big Bad Wolf is trying to get out of his lair," I said as I fondled the crease in his crotch. "I can see that he's big. You'll have to show me if he's bad."
"He's big, he's bad, and he breeds," Randy said. Now he tells me!
"Well, as for that threatening, let us go to dinner," I said. After chili and cabernet, I filled two whisky-tumblers with tequila. I served the tequila with two little blue pills --- viagra. "Strictly recreational," I said.
"Too much for me, not enough for you," Randy joked. He raised his glass for a toast. "To cherry-busting," he said. "I'll drink to that, since we must," I replied. We clinked glasses.
"Your turn to propose a toast," Randy said. "Make it sexy."
"To the Big Bad Wolf," I said.
We donned coats and gloves, and walked down the hill to the dock. I carried a Coleman lantern to light our way. Randy carried an armful of towels, washcloths, shampoo, and soap. The sauna was a small two-room building near the water: an anteroom for hanging up clothes and towels, and a steam room equipped with a stove loaded with rocks, and a row of three benches at three levels, like a miniature stadium. At a small metal door at the back of the sauna, I started a fire with coal in the stove. "It takes at least a half hour to warm up," I said. We drew buckets of water from the spigot, positioned them near the stove. We would have warm water when we needed it.
I took a pair of clippers from its hook in the anteroom. Randy followed me into the nearby woods, where I clipped balsam boughs. In the light of the lantern, the Norway and white pines, the spruce and the balsams, all different shades of green in daylight, merged in shadowy greenness in the light of the lantern. "The same thing happens in sex," I said. "Two guys merge their identities to form an abstract idea of maleness." Spoken like a true philosopher, Randy said.
I clipped balsam boughs. Randy collected them in a bundle. "We use balsam to rub each other down," I explained. "It's cleansing and fragrant. A balsam rubdown stimulates the blood." We stashed balsam in a pile on the top bench in the sauna, and returned to the cabin. I laid out sweatpants and sweatshirts on the bed. I told Randy it would be easier to wear sweats when we went to the sauna --- easier to strip and get dressed quickly in the chilly anteroom. "Besides," I continued, "taking a sauna and then wearing the same clothes is like changing the oil in your car and not changing the filter." The idea of the sauna appealed to Randy. It's part of North Country culture, routine for me, but a novelty for Randy. He liked the idea of preparing for sex by grooming each other's bodies. Some guys like musky mansmells. For me, a squeaky clean body frees the mind from inhibitions.
Randy sat on the sofa facing the fire, sipping tequila from his tumbler. "Before you sit, Jake, there's something I want you to do," he said. He wanted me to get naked. I kicked off my shoes and socks and faced him. I removed my shirt and T-shirt, and flexed my muscles. Randy pulled my zipper down. I stepped out of my jeans and Randy tossed them aside. I modeled my body in jockey shorts. I stood with my backside to Randy while he lowered my shorts.
Randy fondled my butt. I wasn't his piece of ass just yet, but his fingers told me I would be. He didn't have to tell me to spread my legs apart. "You're a beautiful man with a really cute ass, Jake. This ass is going to be the star attraction, not without some help with the Big Bad Wolf." He ran his finger up and down my crack. "Big Bad Wolf like 'em hairy," he said. "It's all about the ass." Randy made me feel like a sex object.
"Hairy ass, smart ass, sweet ass, candy ass, hard ass, bad ass, horny ass," Randy said. He tested the gateway to my ass with his middle finger. "Virgin ass, tight ass, your-ass-isn't-mine-yet-but-it-soon-will-be ass," he continued. He stuck his finger in further and used it like a hook to pull me toward the sofa. I sat next to him. That was his way of telling me to sit.
On the sofa, handy Randy was all over me. With one hand he pinched my nipples. With the other he touched my asshole --- not an easy reach. "Concentrate on how it feels." He said that I needed to add nipples to my repertoire of sexual organs, now that I wanted to become a bottom. While he pinched my nipples I resisted the thought. Randy persisted, and insisted. This was part of my conversion, he said. My resistance vanished. He said that his body was mine, and I would be his in return. Shhh!" he said when I started to speak. My body floated in the transitional space between what I was and what I was about to become.
My ass got most of the points. Randy's objectification of my body was neither deceptive nor degrading. We were role-playing. We knew that. Randy was helping me psych myself up for what I had to do. I was flattered to be the object of his sexual desire. It was a step toward submission, a "sine qua non" in gay sex. Many women dislike this sort of thing, either because they buy into feminist prudery about sex, or because they don't compartmentalize very well. For men who are other men's "sex objects," recreation in bed has nothing to do with one's status and standing in real life.
Dear Reader, I hope you don't mind my occasional digressions into philosophy. Sometimes I like to step back and look at myself and lovers objectively. (I've said "object" too many times, haven't I, and in two different senses of the word.) I'm just trying to clarify that if I weren't totally independent and confident as a man, I wouldn't have had the guts to let Randy assert control over my body. And Randy enjoyed seducing me all the more because I was so independent. I know you're impatient for me to get to the good parts, but I think you'll find "the good parts" more erotic if you understand how we were interacting psychologically.
We got into sweats. I saw Randy naked for the first time. Mostly I ogled his supersized uncut hunk of cock, complemented by rather large, low-hanging balls. His genitals looked even larger in proportion to his short, unathletic body. Randy was entranced by my athletic physique. Still, he noticed me ogling his stuff.
I led the way through the snow to the sauna. We stripped in the chilly anteroom, and quickly made our way into the inner sanctum (my term for the steam room). I splashed water on the heated rocks above the stove. We sat side by side on the top bench, taking steam from the rocks.
Randy put an arm around me while I fondled his nine-inch cock, thick and wedgy. I leaned over to nibble at his foreskin and suck on his cockhead. I discovered that Randy had a rather wide piss-hole. I tasted his pre-cum. In college, had seen a few uncut guys in the showers, but this was the first time I had ever seen a foreskin up close, and touched it. I was a boy with a new Christmas toy. "You can play with my foreskin all you want," Randy said. "It won't hurt me."
We knelt face to face on the second bench while Randy explained "docking" to me. He pulled his foreskin over my cockhead, and fondled both cocks at once. It was an erotic scene, especially for me. "Almost all guys around here get circumcised at birth," I said. "Except maybe the Chippewa-I don't know about them." "Then it will be interesting to find out if Billy White Cloud is uncut," Randy said. I knew that Randy had the hots for Billy. In no way did this detract from our mutual desires at the moment.
We lathered each other's bodies with soap. This was foreplay. Hands and fingers glided over every surface and into every cranny. When the heat got to us, we stood together under the showerhead in the anteroom. The water was drawn from the lake by a pump, so it was ice-cold, but bearable after the heat of the sauna.
Back in the sauna, I splashed more water on the rocks, and gave Randy a massage with a handful of balsam boughs. He lay on his back first, then on his belly. This was a pleasant chore, especially when I stuffed his ass-crevice with balsam. He did the same to me. A few streaks of pitch on our bodies was a small price to pay for the exhilaration of a balsam-massage. When the heat got to be too much, I led Randy outside. We rolled in the snow in an embrace, and returned to the sauna when we started to feel cold.
We fondled each other in the sauna. Randy told me to stand on the floor with my legs apart. I leaned forward with my weight on the bench. He got behind me and fingered my asshole. I was surprised when he ran his tongue in my crevice, and all the way down to my asshole. "Jake, you're so beautiful," he said. "And you've got the most beautiful ass." He teased my by fingering my asshole, gently with just one forefinger. The sensation was amazing. "I can hardly wait to feel your rock-hard ass-muscles against my cock when it's going in and out," Randy said.
I offered to kiss Randy's ass in return. "Not just yet," he said. "That time will come."
Outside again, we played grab-ass with handfuls of snow while we rolled around. Through body-language we declared the roles we would play. Randy was aggressive. It no longer mattered that I was bigger and stronger than him. He forced my arms, and jammed his cock in my mouth. He bundled himself on my backside. He forced my legs apart and finger-fucked me in the snow. He swatted my butt and said that my ass was his. He pinched my nipples and sent shivers to the target of his desire. Whatever he forced on me, I complied. Surrender was coming. It made me feel strong.
Back in the warmth of the sauna, Randy told me to lie on my belly so he could play with my ass some more. After some foreplay, he soaped up his cock and knelt between my legs. He pushed his cockhead against my asshole. I yelped in pain. He ignored my appeal to stop, and forced his mushroomy cockhead through my sphincter. "Just a taste of what's ahead," Randy said. I knew I was in for a long haul.
Another roll in the snow. The pain in my rectum receded. I was unsure of myself, I told Randy, since the pain in my rectum was so sharp. "Not to worry," he said. "That's what lube is for. I just wanted to give it a try." I fingered his foreskin while we sat side by side. Being in possession of the only foreskin in the room gave him a sexual status that he used to his advantage.
"When we get to bed," Randy said, "our first job will be to transform your ass into male pussy. It won't be easy. Some things have got to stretch to make room for my cock. We've got to lay pipe, but we'll do it together."
I knew that, but it was erotic to hear him say it. "You have such a way with words," I laughed.
"The pain will be all yours, Jake. I'll be feeling nothing but pleasure while you are howling in pain." Randy chuckled sadistically.
"Gee, thanks!" I said. The heat was getting to us again. "I think it's time for us to go back to the cabin and just do it."
"Good man!" Randy said. He always said that when the guy he was with submitted to agony. Why would a tough guy like me submit to the pain of getting fucked by Randy? It had something to do with Randy's style. As a top, he was hard to resist. We toweled each other dry and put on our sweats, and jogged through the snow back to the cabin. A minute later we were naked in bed.
Randy took charge. We needed more foreplay to prepare my body. We fondled each other and kissed passionately. Randy kissed aggressively, like a bridegroom. He unwrapped the bottle of poppers. He lay at the side of the bed with his legs toward the floor, and told me to kneel between his legs and suck his cock. I sucked his cock and his balls. He told me to lick his perineum. Then he demonstrated the snorting of poppers, and handed the bottle to me. I did the same, and returned to licking his perineum. Under the influence of the poppers, I found myself licking Randy's asshole. I complied when he told me to fuck his asshole with my tongue. After that, I rimmed Randy's ass in different positions, and snorted poppers for inspiration. These were two "firsts" for me: poppers, and rimming.
Dear Reader: here's a caution. Don't do this at home. Viagra and poppers don't mix, unless you're a strong, young athletic guy, and even then, use poppers sparingly. Don't deny your partner the joy of rimming, but when you do it, use cellophane for protection. Still, when you're with me in this sexual fantasy, there are no limits.
Randy told me to lie on my back in the middle of the bed. He propped a pillow under my ass. He straddled my chest and fed me his cockhead. It was wet with pre-cum. I tongued it and sucked it. He straddled me ass-backwards and lowered his asshole to my lips. I kissed it and licked it. He lubed his middle finger and gently inserted it up my asshole. "Oooo," I responded. He pinched my nipples and kissed me softly. He told me to pinch my nipples while he inserted his finger again. "Jake, try to concentrate your mind on your ass. Focus on how your asshole feels. And let me feel you tighten your sphincter around my finger." He finger- fucked me while I pinched my nipples. "Don't say anything, Jake, just concentrate your mind on your ass. Let's not either of us say anything that will break your concentration. I've got two fingers up your ass now, Jake." He removed his fingers and held them up. Then he stuck them up my ass and wiggled. "Shhhh," he reminded me not to speak. In low tones, he said, "it's a gradual process. If you focus on how it feels up your ass and do everything I say, your cherry will be popped by the time were through." Randy was a patient lover. He spent fifteen minutes at least, finger-fucking my ass while I pinched my nipples and tightened my sphincter around his fingers.
I suppose every top has a unique seduction style. So far I was liking Randy's. I thought he would switch graduate to three fingers up my ass. Instead he showed me the vibrator. Following his instructions, I said nothing. He wrapped the vibrator in a condom, and coated the condom with lube. He took care to see what he was doing. Watching his preparations was part of the eroticism of the scene. Slowly, he inserted the vibrator up my ass. It was narrow, and maybe seven inches long, which means I must have taken about six inches of it. He pinched my nipples, and drew my hands to them. I obeyed his silent command, and resumed pinching my nipples. I concentrated my mind on the feeling in my ass. Randy turned on the vibrator. Its soft whirring was the only sound in the bedroom. He smiled when our eyes met. The incredible sensation took me by surprise. Even more so when Randy started moving the vibrator in and out of my ass in slow fucking motions, and rotating it inside my asshole. Randy watched my body writhe in the pleasure of the moment.
Randy let the vibrator run on automatic. He held up the middle finger of his left hand. He squeezed his middle finger with his left thumb and index finger. This was to tell me to squeeze my sphincter around the vibrator. I obeyed his silent command. All my senses were engaged in the act of making love to a vibrator. While this was going on, he pinched my nipples while I pinched his. Our eyes locked together in wordless concentration.
Randy wasn't satisfied that the vibrator had done its work. He pulled it out slowly, than thrust it back in. My body bolted. Randy liked that. He repeated the vibrator-fuck for several minutes. Then he covered his throbbing cock with a condom, and coated the condom with lube. He leaned forward and kissed me passionately. I kissed him back. Slowly, he pulled the vibrator out.
A great howl was audible across the lake when Randy drove his cockhead through my sphincter. "Shhh!" Randy said as he pushed his cock deeper. It passed through my inner sphincter. My howl was less loud but the pain was greater.
"Take deep breaths, Jake, and concentrate on your breathing," Randy said.
"Easy for you to say," I sputtered between deep breaths.
"Shhhh!" Randy said. He gave me a third jolt. I groaned mournfully. "Relax, Jake, I'm all the way in now," Randy said. With my right hand, I reached around his thigh and felt the base of Randy's cock at the point where it disappeared into his ass. Randy was right.
"I call it 'the three blows', Jake," Randy said: "initial penetration, a thrust through your inner sphincter, followed by compete possession of your anal canal. You're skewered. Your cherry has been popped. The hard part is over. We'll just lie together like this while the pain subsides. Then the fucking begins." He looked in my eyes and smiled slyly, like a fox who carried off just raped a golden-egg goose. "Do you realize, Jake, I've had my cock up your ass for a good half hour." We looked at the clock in the dresser.
The pain up my ass (I don't mean you, Randy, dear), the pain up my ass dissipated to a dull throb. It gave way to a feeling of fullness, as if all I had all of Randy in my body, not just his cock in my ass. The sensation, strange at first, grew on me. Randy seemed to read my mind. He moved his cock inside me, in slow, short fucking movements, and gradually increased the tempo and the length of his strokes. The pleasure showed in my eyes, which were locked with Randy's. It felt like when I was a boy, learning to ride my bicycle. After hours of unsteady practice, the feeling of the bike came at last, and then I felt free to ride. That's how it felt getting fucked for the first time by Randy. Once I got into the rhythm, surrender was easy.
Randy knew how to fuck a guy. He started to alternate between energetic humping, and slow, gentle massages of my anal canal. The boundary between pain and pleasure was blurred by those gentle massages, punctuated by sudden sharp jolts that occurred when ever Randy seemed to find a part of my ass that hadn't been skewered yet. I was so enveloped in ass-pleasure that I wasn't aware that my cock had grown flaccid.
Randy pulled his cock all the way out of my ass. His eyes locked with mine and he smiled slyly. I felt a sudden jolt when he thrust his cock all the way in. It came as a shock. Then Randy did it again. I was being introduced to humping, or one form of humping. I didn't protest the jolts and the sudden thrusts. Instead, I surrendered myself to the feeling. Randy nodded his approval.
"You're bottoming out," Randy said.
"What does that mean?" My voice was thin. I was singing soprano.
"It means I've unlocked something deep inside you, a longing that needs to be satisfied," Randy said. "It means you're becoming reborn as a bottom. That's a good thing, trust me, Jake."
Randy's voice deepened from tenor to a trumpeting bass. He was my Summoner, and "bar to me a stif burdoun," whilst I, his new-made Pardoner, sang "Com hider, love, to me!" Our harmonized voices were music from the spheres of heaven. Randy humped for effect. It was pain and pleasure, an erotic mix.
Randy pulled out his cock and told me to lie on my belly so he could fuck me from behind, doggy-style. "I'll do it if you take the condom off," I said.
"You want to fuck bareback?" "Yeah, bareback!" - Bass and soprano, still in harmony. It was cosmic! "I can do that," Randy smiled. He tossed the condom to the floor. I turned over, ass-arched. Randy got inside, naked as a needle.
I had always imagined that doggy-style would seem impersonal. I was wrong. I still prefer missioning. Eye-contact is essential in love-making. But when Randy fucked from behind, I felt full weight of his body. This was intensely personal. In this position Randy could fuck as hard as he wanted. He jolted in places previously undiscovered by his nine-inch probe. He took full advantage of my surrender. I wouldn't have had it any other way. There was something special about the kisses we shared from behind, accomplished with neck-craning effort. I looked back at him, a sign that I was lovin' it.
A top can be counted on to appreciate the beauty of a cute ass. It's only fair to let him fuck from behind if he wants to. Randy liked to watch his cock going in and out of my ass. I was happy to be with him when he was so satisfied.
The body-heat between us was rising. Randy turned me over on my back, and sucked my cock until he returned to full hardness. I was totally his and liked it that way. I enjoyed my role as a bottom-in-training, mainly because Randy presented the tasks of the bottom in such positive ways. He was keen on the responsibilities of a top. We spoke about this often. He had devised "ten "commandments: for tops, and ten for bottoms. "Love your partner, and respect all past and potential future partners," was his first commandment for tops and bottoms. What were the other commandments? I wondered. Randy said we'd talk about that later.
We were headed for the finish line. Before we got there, Randy said he wanted two things clarified. First, he wanted me to have an orgasm while he fucked me. This was possible, if he fucked me gently. Second, he wanted to breed me. "I want to invade your garden of delight with an army of my little soldiers," was the way he put it.
"My cherry won't be popped completely until its swimming in a sea of bull's milk," I said. Lust gleamed in his eyes. He liked the idea that cherry- busting was still going on.
Randy repositioned me at the side of the bed so he could stand between legs. I rested my ankles on his shoulders, and opened my ass in a frog-leg position. Randy entered and humped me fiercely for a few minutes. Then he slowed down, and sometimes kept still, while we took turns fondling my cock. "This is the best fuck I've ever had," Randy said. "Amazing, considering it's your first time. You're a natural, Jake, a natural."
"Flattery will get you inside," I laughed. My cock was swelling and throbbing. "I feel totally reconfigured inside," I continued. By now I was quite horny, and ready for intimate confessions. "I'm glad it was you who turned me into a bottom. My ass is yours, anytime. I'm glad you have such a monstrous huge cock. Getting fucked for the first time was a challenge, but worth it. I'm even glad for the pain up my ass."
By now it was mostly me frigging my cock, but Randy pitched in to give me variety in the sensations I felt. He seemed to know just the right moment to offer me the bottle of poppers. I took a deep snort, and that sent me over the edge. My orgasm was stronger than any that I could remember.
I needed time to catch my breath. Randy centered me on the bed and propped my ass with a pillow. He entered me again, and fucked slowly. "I'm going to breed you now, Jake. I'm going to breed you."
"Yeah, breed me!" He wanted to hear me say the words. Randy humped me furiously. I could feel the warmth and swelling in his cock just before he came. He gasped furiously. He poured himself into me. I felt milky inside.
Randy lay on top of me and panted. Less than five minutes later, his cock was hard again. He flipped me over and humped me doggy-style, fierce and fast, and shot a second dose of bull's milk into my now-broken cherry.
Afterward, we lay in bed side by side, embracing each other, silent for a long time. Debriefing is important. Call it pillow talk. Without it, both partners feel that they've been used. One of us had to break the silence.
"I've always had a theory about anal sex," I ventured. "It's the maximal form of cooperation between two men. To make it possible, each guy has a lot to do to help his partner. Otherwise it won't work."
"I've always had a theory about breeding," Randy replied.
"What's that?"
"Every time I breed you, some of my DNA enters your bloodstream. Part of me becomes part of you, which brings us closer together as blood brothers, as well as lovers."
"You'll have to breed me more often," I said. "Maybe once or twice before the night is through."
"I'm proud of you, Jake. It took guts."
"My ass is still throbbing with the physical memory of your cock, Randy. From now on, you're the holder of my cherry."
We showered. We took turns washing and rinsing each other's bodies -- another way of taking care of each other. We fell asleep in each other's arms.