PART 11 --Cherry Jubilee
Obviously, ever since Rut had become active, in a homosexual way, he had been fretful over the loss of his own personal virginity. He had personally deflowered several seemingly straight men, namely Russ, Jim, Jack and Philippe in recent memory. He had gloriously ravished each one in their first homosexual experience. All had accepted the introduction of his ten-inch hard dick up their rectum without too much trauma. In fact, they had gladly offered their asses to Rut countless times afterwards without any anxiety. All had wanted to fuck Rut, but he had selfishly refused to share his body. Why couldn't Rut let himself be fucked by any of the men he had known sexually? It may have been a Trojan horse mentality. He steadfastly refused to allow anyone's bone up his ass that caused him to refuse complete sexual intercourse with another man.
At this point, a superior officer, Akido, propositioned him. Career wise this could be very meaningful. If he refused there is no telling what Akido would do on his next fitness report. Akido's good opinion was an invaluable asset. In addition, a less than satisfactory fitness report could cause him to resign his commission and quit the corps. His personal conduct as an officer and a gentleman might not stand too close a review in the event he filed a sexual harassment charge against Akido. Apparently, Akido was relying on this flaw since he was aware of Ruts secret life as a gay exotic dancer.
Rut resented the pressure Akido had exerted. Akido, in Rut's opinion was a good sex partner and although he was an older guy, he had performed like a horny satyr with a super-human libido. Rut was pleased with the initial sexual experience but knew that it would have to progress to the point where either he or Akido would have to give up their cherry. Was Rut prepared? Psychologically he was still floundering.
He had carelessly stashed away in his memory the fact that he would only give up his cherry to a man he was deeply in love with at a particular time. Thus far, Russ was the only guy that filled the bill, but Russ had now developed an insatiable appetite for sex and sought it out where ever he found it. Russ seemed particularly enamoured of Alex. Perhaps this was so because he did not have daily access to Rut. Although Rut knew that they were fucking every night and Russ, knew that he was having sex with Jack every night. Rut, on the other hand was lasciviously enamoured with Jack's physique and sexual naiveté and he wanted to continue to mentor Jack in his exploration of rough man-to-man sex. Rut was also secretly craving a long-term meaningful sexual experience with Alex, and he knew it was reciprocal, however the same impediments that Rut was experiencing with Akido also applied to any sexual liaison with Alex. Fucking around with either a superior or a subordinate in the corps could get him in big fucking trouble. Better to continue with Jack, his equal in rank than to explore any of the other possibilities.
Therefore, knowing his fate was inevitable, he decided to take matters into his own hands. He planned his own defoliation, both literally and figuratively. Since he already knew that taking a cherry was a painful experience for the uninitiated, he had decided to prepare his anal sphincter to accept a lover's big dick.
So, he went to a local adult boutique and purchased a dildo. It wasn't one fashioned after any well-known male porn-star with a super sized dick. It was just an ordinary eight-inch rubberized phallus. It compared well with any of the current guys with whom he was sexually active. On the evening of the purchase, alone in his bed, he began his own pseudo deflowering.
Using the fingers of his right hand he inserted them in his anus and began to stretch it to accept the dildo. Using a lubricant, he prepared his anal cavity and the dildo to enter inside. Rut inserted the bullet shaped mushroom head of the dildo inside himself and forced himself to bear down like he was trying to take a shit and allowed the dildo to pass through his anal sphincter. It was indeed painful, but Rut was successful in getting three or four inches inside. Rut allowed it to lodge in his rectum hoping to get accustomed to the penile instrument. He lay there, naked on his bed, sweating the sensations he was feeling knowing that from all accounts this should soon begin to be a pleasurable activity. Fifteen minutes passed and he was content to lie immobile and let his ass adjust to the quiescent implant. Had it been a real cock inside his ass he knew that his lover would have long since started to flail away at his ass and the pain would have dissipated faster. However, he slowly began to manipulate the phallus inside himself hoping to massage his prostate. Eventually the bogus penis began to do its work, he could feel the head of the penis caress his prostate and he developed a colossal hard-on. His cock was so hard he could have cut diamonds with the tip of his prick, which was leaking mucho pre-cum. All the while he maneuvered the dildo, thrusting it in and out of anal sphincter and bouncing it off his prostate in an effort to get himself off. Soon the dildo took on a life of its own, Rut began to pound his ass harder and harder, and he could feel his testicles contract with seminal fluid, which he soon released. Without touching his own penis he shot ropes and ropes of seminal seed onto his abdomen and chest, even managing to grab a taste in his mouth, until he drained his ball-sack dry. Exhausted he lay on his rack while his body continued to enjoy the sensual experience he had evoked.
Recovering, Rut took an old gym sock and wiped his body clean. Normally, after any autoerotic pleasure he would have licked his hands clean of ejaculate and enjoyed tasting his semen. Better, after sex with a guy he would usually have had his lover help him to clean up what they had shared together.
Rut thought about the experience, and tried to convince himself that he was no longer a virgin but that logic failed. The experience may have simulated the sex act, however he was convinced that until he actually had a live cock up his ass he was still a virgin. The dildo, serving as a proxy cock allowed Rut to feel all the sensations of a simulated sexual act. However, he knew that the pleasure derived could not really compare with the actual event of having a mature, flesh and blood, and throbbing live dick working out on his ass. Therefore, he knew he would still have to experience having a live penis invade his anal cavity before he could fully engage in future sex acts of any kind.
Rut was certain he wanted Russ to be the first top he would bottom for, but he also knew that he wanted the other guys to share that experience. Rut had stood stud like a stallion for other guys for several years, now he wanted a personal celebratory occasion for his own deflowering that had not been available to others. He wanted his own deflowering to be delivered up with dignity and reverence. So, he needed a plan.
The battalion had scheduled a fitness test for all officers and NCO's for the last week in September. So all the guys, Rut, Jack, Alex and Akido were out daily running the two miles to get under sixteen minutes, and doing the sit-ups and pull-ups that Akido had formulated to certify each officers level of fitness. With two weeks to go before the actual test, Rut decided they should have a long weekend at the beach.
Rut rented a four-bedroom beach house, not to far from the base and invited all the guys to come with him for the weekend. Arriving, he assigned separate beds. Rut got the master suite with Russ, Jack and Alex getting the other three bedrooms. There was also a loft guestroom for Akido. The place had a private swimming pool, sauna and hot tub, with access to the beach. Akido had brought along red thong swimsuits; each had a gold marine logo across the pouch and an almost invisible string buried in the ass crack. Akido said they would be good for running on the beach. The swimming pool was so secluded that they could swim bare-ass, which they did.
Late that afternoon, wearing thongs and their combat boots, they went for a long run on the beach. Two miles out and back at top speed. Alex got back first, then Akido with Jack and Rut coming in a dead heat last. Russ took a short cut and caught a ride from some surfer dude and together they were in the pool when the others arrived back at the house. Russ was sitting on the side of the pool with a bobbing blond head between his legs. Looked like he was getting a blowjob from the new guy. One by one, the others joined them at the pool and soon all were enjoying a cool dip. The sight of four other hunks bobbing about the pool naked mesmerized the surfer dude and he could hardly concentrate on blowing Russ' dick.
The weekend was for relaxing, working out to improve their time on the fitness events and to lead a monastic existence away from the pressures of the base. Getting naked was a nice accommodation that was not usually available to them. All these guys were exceptionally well built, young and horny as hell. But, they did not want to have this weekend degrade into an orgy of epic proportions, so they had agreed to curtail any sexual activity. Russ was the exception since he was not in the corps.
Russ and the surfer dude managed to slip away to find some privacy in Russ' bedroom where the surfer could continue the blowjob that had been interrupted.
Later, the guys dressed casually and headed out to a restaurant for dinner where they ate sparingly and sipped ice tea. Arriving back at the house they bid each other good night and went to their respective beds alone. Up again at dawn they did the daily dozen, led by Akido. Sit-ups and pull-ups followed by a two-mile run on the beach. Later it was a light breakfast and then they collapsed on the chaise lounges around the pool, naked to soak up some sun. Russ had joined them and then offered anyone who wanted it a full body massage. Akido volunteered. Russ straddled Akido's nude body on the chaise and worked the shoulders and upper body, kneading the oil into the sore muscles. Russ did the small of the back and the hips, concentrating on the two melons like ass cheeks working the stiffness out of the older man's body. He massaged the gluteus and hamstrings, as well and asked Akido to turn over. Akido had developed a huge erection so Russ began to massage that as well. However, the other guys told them to quit it and take a cold shower, which Akido did.
Rut, in the meantime was planning to be fucked. He was determined to bottom for someone this weekend and time was running short. Last night he had toyed with the dildo and managed to bring himself to orgasm, but he wanted to experience it one on one with another guy. He was convinced that he was going to give it up and he had selected his partner. That night he invited his lover to visit him in his bedroom. When the time came, he opened the door wearing only a white string thong that barely contained his erect dick. He and his lover approached the bed and Rut reached into the night table and brought out a gold ring which he gave to his lover and asked him to place it on the head of his dick. The ring fit him perfectly. It was a cock-head love ring.
Rut wanted his lover to place the ring on his dick just behind the cockhead and just past the corona ridge of his cut dick. Rut pulled off the thong and lay back on the bed pulling his lover toward him. His lover was already naked and Rut handed him a condom. His lover was surprised but he tore the package open and pulled the rubber over his erect cock. Rut, on his back, raised his legs to his lover's shoulders and offered up his pristine rose bud. His lover at first rimmed the anus and tongue fucked Rut trying to relax his love chute for the acceptance of his penis. He lubed the anal entry with lots of KY oil, which he also applied to his rubber-covered cock. Without further preamble, Rut urged his lover to insert his dick in his ass. He was ready and wanted to complete the act as soon as possible.
Rut felt the huge dick probe his anal opening and his lover's hand helped guide the dick to the opening. Inserting the tip inside, his lover paused for an instant, which allowed Rut to savor the second that seemed like an eternity. It felt comparable to the dildo that Rut had used but there was involuntary movement associated with a live dick that the dildo had failed to prepare him for and for the moment, Rut wanted to end the session. However, he hung in, knowing that there was no turning back now.
Rut urged his lover to continue as he used his hips to forward thrust so that his ass accepted more of the dick inside himself. Feeling the ridge of the cut dick caress his prostate he began to flail about urging his partner to continue. His lover began to gently thrust and withdraw his cock inside of Rut, tantalizingly so that Rut could hardly stand it. Rut's legs were resting around his lover's hips, and his lover began to thrust harder and harder pushing his big dick in and out in rhythm with his shallow breathing. He watched his lover's face all the while seeing the pleasure he was giving him in the contortions of his countenance. His eyes revealed all. He saw reflected in them the love and respect that his lover gave him knowing that he was on the receiving end of a sacrificial offering that no other man had ever been given. His lover knew what was happening and approached the act with love and gentleness. Rut wanted his lover to increase the thrusting and pound his ass to the point that his lover had an orgasm and he could feel his love juices shoot as from a cannon inside his body, captured by the condom. His lover coaxed Rut to his side and managed to lie side by side while he continued to pound his ass. Rut felt his love juices concentrate in his gonads, swelling them with his fluid waiting to be expelled. Rut wanted to have a simultaneous ejaculation with his lover and he was waiting until he could feel his lover release his fluid inside his body before he released his own sperm.
They continued the thrusting and pounding for several more minutes, Rut using his anal sphincter muscle to grab and massage the penis in his ass. Finally, he let out a guttural sound indicating that he could not contain himself much longer. His lover was also tensing his body and Rut could feel the other man's testicles clamp as they smacked his groin with each thrust. Finally, Rut began to expel his ejaculate, which he shot with such force that the ropes of jizm catapulted across the room from deep within his groin. He shot four, maybe five ropes when he was joined by the convolutions of his lover and he cried out his lover's name "Russ, oh Russ, R u s s s s ssssss, arghhhhhhg, fuckin' way to go, man!"
Lying together afterwards, Rut thanked Russ, told him he had wanted to do this for such a long time, and was now glad that they had truly consummated their love for each other. He then reached into a draw and brought out a second gold cockhead ring which he placed in his mouth. Lovingly, Rut shimmied down in the bed until he was eye level with Russ' cock and then using his teeth and tongue ceremoniously placed the love ring on Russ' flaccid dick just past the corona of his cut penis.
They rested for a short while, then Russ urged Rut to fuck him. Rut kissed him full on the mouth, his tongue probing the oral cavity and playing with his lover's tongue. Softly his mouth moved down the body until it came to Russ's tits, which he bathed with his tongue and sucked inside his mouth until they were hard and tender to the touch. His tongue licked his entire body, dwelling on the washboard abs and inside the crevice of the navel until he could taste the cheese that had collected there. Reaching for a jar of honey Rut smeared Russ' belly and pubes with it and then began to lick the honey off. He paid particular attention to Russ' cut engorged cock and loved the combined taste and smell of the honey and male pheromones that emanated from the pubes. Taking Russ' cock inside his mouth, he began to bathe it, washing the honey and his own cum off the cock until it was clean. Russ began to leak pre-cum and Rut took the head of the penis in his mouth and captured the nectar. He sucked and sucked the cock until it was huge and oozing tremendous amounts of seminal fluid in his mouth, which he savored like choice wine. The cockhead ring was a good fit and did not move much. It was a good fit, almost welded on his cock. It was a great feeling inside Rut's mouth. Now he wanted his own ring clad cock up Russ' ass.
Raising Russ' hips he rested his legs on his shoulders bringing Russ' ass in close contact with his cock. Rut paused and put a condom on over the cock and ring and began to press Russ' anal sphincter. He entered quickly. Russ had stretched his anal opening well in the preceding months and it now easily accepted Rut's big dick without any trouble. Just as Russ had done to Rut, Rut gently plunged his dick deep inside of Russ and began to pump his dick head so that it massaged Russ' prostate. Together they began a rhythmic fucking motion that brought them each the greatest of pleasure. Rut could feel his cockhead caressed by Russ' anal muscle, drawing it further and further inside his body. Rut could feel his testicles fill with sperm and Russ was massaging his dick head with precision within the anal cavity so that it was not long until he began to loose his ejaculate inside of Russ. Meanwhile Russ began to shoot his wad all over Rut's chest and abdomen. Later, Russ would lick the love juices that he expelled and implant them inside Rut's mouth where they both enjoyed the taste and smell of their love.
In the morning, Akido had early morning revelry of sorts to begin their morning exercises. All the men, dressed in the red thongs, did sit-ups until their abs was strained and sore. Their abs were flushed with blood and the muscles swelled so that their bellies looked like marble blocks chiseled like Michaelangelo's David. Each man had to do a minimum of twenty successive pull-ups at a makeshift bar near the swimming pool. Akido did thirty of them and his arms felt like they were almost ready to be wrenched from his body before he dropped to the ground. Hanging leg raises to work their lower abs immediately followed these pull-ups. When all the calisthenics were done it was down to the beach to run. They were now running four miles in the morning and again in the afternoon, trying to get below an eight-minute mile. Alex and Akido were doing seven-minute miles and Rut and Jack had cut their time back to seven and one half minutes. All were pleased and knew they would pass the fitness test successfully.
Later that morning they went to a local gym for a workout. Most ended up doing shoulder and chest exercises with heavy weights. The five of them were exceptionally well developed broomtail studs and the other guys in the gym looked on admiringly. They were clearly identified by their jarhead haircuts as military fighting machines and their bodies were things of the utmost male beauty. After the workout they took some steam and soaked their sore bodies in the hot tub.
Akido wanted a massage and again Russ offered to do him. So, naked they went to the sauna and Russ began to work his magic on their sore bodies. The sexual overtones of Russ' magic fingers eventually aroused five men, naked in the sauna and there were at least four of them hard at any one time. At one point a young gym rat sauntered in to the sauna, looked around at these five demigods and fearful of his manhood left quickly. Eventually they left the gym and headed home for a swim and a nap sexually unfulfilled.
Akido was in his loft bedroom, lounging in a pair of tailored boxers that fitted his slim hips and ass like a glove. His dick head would peek out the opening of the boxers whenever he moved. He had been hot and horny before coming down to the beach and after getting here; he was even hornier. The more he thought about sex the hotter he got. He had so long denied himself the pleasure of male sex that he now had an insatiable desire to fuck every man he met. He looked at the possibilities. Russ was the only guy not in the military and Akido had no power over his actions. He thought Russ a likeable sort and wondered what kind of lay he would be? He had a great ass and Akido thought his dick would fit well inside that bubble butt.
Akido was most attracted to Rut, especially since he had seen his nude dance routine in a gay bar. Every time he thought of that night and the great sex he had enjoyed following Rut's performance he had wanted to personally fuck Rut. But, like Akido, Rut was not versatile. He was strictly a top. But, sadly he wanted to experience anal sex at least once and thought Rut should be his partner. However, he was not about to bottom for some hot shot second lieutenant within his own command. Especially one who would not bottom for him.
So, he decided that today would be the day he lost his cherry. He asked Russ to meet him in the loft ostensibly for a massage. When Russ got there, Akido had firmly decided to go ahead with his plan. He asked and got a great massage from Russ. Akido dropped his boxers and took a wide legged position on the bed with a naked Russ straddling his hips. Russ massaged the shoulders and back with hot oil and gave a deep massage paying particular attention to Akido's back and hips. Finished with his back, Russ was thoroughly massaging the bubble butt mounds of his ass and hamstrings. Turning Akido over he was not surprised that the Colonel had sprung his usual eight-inch hard-on. Russ took the cock gently in both his hands and gently began to jack Akido off. However, Akido instead handed Russ a condom and told him to put it on his dick and fuck him. Russ did not know he was cherry, so he proceeded with haste to make Akido's ass receptive to his cock. He placed one, then two fingers in the ass hole and began to massage the prostate manually. All the while Akido's ass was beginning to dilate so that it would accommodate a penis. Russ gently raised Akido's legs to his shoulders and applied some lube to the anal cavity. Once done he placed his cockhead, sheathed and lubricated in the condom, at the entrance of the Colonel's man pussy. He got an inch inside and could clearly see that Akido was in pain, so he paused telling Akido to bear down as if he was taking a shit so that his prick would slip past the anal sphincter. In a little while it was in and Russ rested, allowing Akido to become accustomed to him being inside. Russ could feel his dick expanding and twitching inside of the Colonel. Akido, in spite of the pain, wanted to continue fucking, so he urged Russ on. Russ pushed his entire eight-inch penis inside up to his pelvic bone and again he rested while Akido got used to his presence inside his love chute. Akido responded by squeezing Russ' penis with the muscles of his anal canal, gently massaging the penis while it rested inside him. Slowly but surely Russ began to pull out and push inside again, thrusting his hard dick to the hilt and back again in swift succession until he began to feel his sperm swell up inside his testicles that were separately swinging inside his ball sack and slapping against Akido's ass with each forward thrust.
Akido's face contorted with pain made Russ think that this was the first time anyone had fucked Akido. Twice now in close succession, Russ had taken the cherry of two close friends and he felt great. He did not get to fuck virgin ass very often so he was appreciative of the sacrifice and honor each man had given him. Armed with that intuitive knowledge, Russ started fucking his friend with class. He got Akido to go on his side without letting his penis slide out and he continued to fuck Akido from the rear, all the time kissing and hugging his friend gently and urging him on. Soon, Russ' testicles began to ache because they were filled with sperm waiting to shoot through his penis into his friends ass where it would be captured by the condom he was wearing. Together both men let their cum escape the confinement of their testicles and shoot true to their target. Akido's love juices were catapulted in an arc and landed on his shoulder and chest while Russ managed to thrust one last time and shoot his wad in four deliciously convulsive spurts into his lover's ass. It was a joyful experience for both men. Russ had taken a cherry while managing to make its loss a cherished beginning for a newer and more meaningful sexual experience for Akido. Russ was appreciative of how Akido had worked his ass muscles, having them play on his penis to bring him to a passionate orgasm. Exhausted they crumpled on top of each other and rested in the bed. The deed is done, thought Akido!
On Monday, the four-day weekend was ending so they planned a barbecue swim party. Russ had invited the surfer dude, Seamus, that he had continued to fuck during the course of the weekend. He had been one busy bee -- fucking Seamus, Rut and Akido all in the same twenty-four hour period.
After an afternoon of eating, swimming and drinking beer the six guys felt relaxed and were lounging around the pool swapping stories of sexual conquests and Rut began to recount his first time ever with his college roommate. They shared a room in the jock dorm and were constantly naked, either changing clothes or sleeping naked. Rut had managed at even that young age to attract good looking muscle dudes to do things they never thought possible. Late one night his roomy decided he wanted sex with Rut and dropped to his knees and took Rut's flaccid dick inside his mouth and began to suck like there was no tomorrow. It was not long until Rut had his first taste of cock and like it. Thereafter, he began to fuck his roomy on a regular basis and the guy couldn't get enough of Rut and his ten-inch pole. Word got out that Rut had a huge cock and guys were lining up waiting to suck him off or just let him fuck them. He even got a psychology professor to give him a blowjob and the professor promised he would ace the course.
So, finished with their reminisces Rut said, "OK guys, let's fuck!"
So six guys went at it hot and heavy. Rut got Akido in the pool and began to blow him underwater, while Alex and Jack did a sixty-nine on the diving board. Russ threw the surfer dude a doggy style fuck. Out of the water, Rut invited all the guys to fuck him. Ceremoniously he gave each man there a thin gold cock love ring and a condom. Rut took each ring in his mouth and placed it on each cock head, just behind the corona. Once done he lay back on a chaise lounge and each guy, one at a time, put his fuck pole up his rose bud. Akido was first inside his ass and was pounding him so hard his balls were jumping up and down each time he did a forward thrust. He didn't get off inside because Alex was waiting to stick his pole inside Rut's ass. Rut was taking each one of their cocks up his ass. After Alex, Jack took a turn then Russ and finally the surfer dude who was so excited he came almost immediately. After having their dicks inside Rut they all sat on chairs looking at each other and enjoyed a circle jerk. Each guy brought himself to climax shooting their wads into the pool before jumping in and cleaning themselves up.
After an afternoon and evening of sucking and fucking they formed two groups of three each and went off to find a bed. Akido and Russ slept with Rut, while Jack, Alex and the surfer dude shacked up in Alex's room. Akido wanted Rut to fuck him so Rut put his pole up the colonel's ass and slow fucked the shit out of him while Russ sucked his dick. They did not get too much sleep that night, while one guy was sucking another off the other guy was fucking him at the same time. It was delicious sex, enjoying the dual sexual gratification of fellatio and fucking at the same time. They sucked and fucked each other throughout the night, while several guys swapped bunkmates and fucked each new bedmate senseless. The surfer dude was very popular; all five guys fucked him silly during the course of the night. Morning came and Rut and some of the others, limped out of bed with legs bowed to give his fuck hole a chance to mend. Once up they celebrated with a champagne toast to their lost virginity and vowed to fuck a cherry guy every week for the rest of their natural lives. It was not meant to be an idle promise.
This concludes the story of 2nd Lieutenant Rutherford Hayes Smith, marine and part time exotic dancer, and his sexual exploits during his first year of his active duty career in the corps.
Hope you enjoyed it? Let me know at Rutsmith@yahoo.com