Bobby

“Hi stranger” Peter said. “Where you been hiding out”.

“I’m just getting off work and heading home, want to burn one” Bobby asked. Bobby’s music shop was just down the street and they to walked a few blocks in the cold slushy streets to a nearby apartment building.

Upon entering Bobby’s pad Peter remarked:

“Wow, quite a place. How’d you afford this”? The apartment was small but elegant with some of Bobby’s guitars along the wall. The floors were polished hardwood and a tiny fireplace was in the corner. The furniture was simple and sparse but still appeared to be more than what person Bobby’s age could afford.

“Let’s just say I have a benefactor,” Bobby said as the two sat down on the couch after Bobby had put on some music. He continued “I don’t know if Yvette ever told you but she knew about us in bed together the morning after we met that night of the concert”.

“Yeah, she did” Peter remarked, remembering that uncomfortable conversation with Yvette.

Bobby had now fired up a joint and passed it to Peter. “Well she was a bit inquisitive and she asked me if I was gay” Bobby said as he took the joint back from Peter. “I didn’t know what to say, ‘cause I guess I didn’t know for certain at the time”. They paused a bit in their conversation as they finished the joint. “She made me think about it. I guess I pretty much am gay in my own way now that I’ve been on my own for a while. You’re very lucky to have a girl like Yvette. I’ve with a few off & on but with me I guess I’m doing well enough being like I am.”

“What do you mean”, Peter asked.

“I don’t know how to say this or if you know about what Yvette did to me one day, but” Bobby didn’t finish when Peter interjected:

“When she dressed you up”?

“Yeah, she told you then” Bobby said, glad that Peter wasn’t finding out for the first time. “Well that’s not the first time its been done to me. The first time from a girl, but it’s kind of who I am”.

“On the fem side” Peter asked. Bobby nodded his head and shrugged. “That’s cool” Peter said. “We all have our own kinks, goodness knows, I do. What’s this about a ‘benefactor”?

“When I was living over by your place I got this job down here off of Boylston Street and it was a long haul but I loved where I was working. Being the new guy though, I was not getting many hours and it was tough making it. One day a man came in to buy a guitar for his nephew. He was well dressed and all through buying the guitar he kept giving me the ‘look’, you know, well maybe you don’t, but I get it all the time, the look guys give to come onto another guy”. Bobby continued, “He came back the next day and wanted to see me. I figured I might as well us it to my advantage and see where I could take it. Things turned out differently than I thought and we kind of have a ‘relationship’ where he takes care of me”.

Bobby thought about how it had happen but felt after his miserable existence with his father life owed him something. His lover, John, was a well to do investment banker who had just turned 40. He was an athlete in college and now very well off with a society wife he married in his thirties but they had no children. He indeed came on to Bobby, but Bobby played hard to get. He called Bobby and asked him to play guitar for him, inviting him to a plush hotel downtown. John got the room for the sole purpose of coming on to Bobby, the alluring sexuality he generated intrigued him and he was wowed by Bobby’s playing. Bobby played it cool and knew what the gentleman had in mind. He politely, but indignantly left when John offered him $300 to sleep with him, saying, “what do you think I am, a whore”.

He thought would never see the man again but Bobby was surprised when John showed up the next day at the shop to apologize. Bobby played it cool, but let John know there was a possibility that he might be interested in a rendezvous. They ended up back at the same hotel that night. With John’s wife out of town, he had a few days to spare on his own. In the sitting area of the hotel room they sat on the couch together and talked and drank some expensive wine. Bobby pulled out a joint and though John had not partaken since college he got a buzz on from the weed and the wine. Both he and Bobby were feeling mellow and Bobby told John about his life and his father, opening up his world to someone on the complete opposite end of the socio-economic spectrum. John was entranced and fascinated hearing the story of his life and of Bobby’s sexual awakenings that ultimately ended up a Peter & Yvette’s place.

As the evening wore on John appeared to be aroused and carefully laid his hand on Bobby’s leg. In due course Bobby crawled stealthily into John’s arms and kissed him. A bi encounter he had in college piqued John’s bisexual interest and the erotic nature of his clandestine rendezvous with the feminine and mysterious Bobby was highly appealing to his newfound sense of adventure.

When he lived at the frat house of an Ivy League school John stumbled into the room of a frat brother who was masturbating alone on his bed. The fellow had assumed all the others had left on spring break and had left his door unlocked by accident. In a bleary hangover John absentmindedly opened the wrong door as he returned to the house to retrieve some item he had forgotten. Lying there on the bed was a frat brother in his girlfriend’s panties and a bra draped over his chest, jacking his cock furiously among piles of open girlie and gay porn magazines. John stood there in shock as the fellow in his horror realized he was discovered.

Nearly in tears the boy pleaded with John not tell anyone. He got up, closed the door and pleaded again for mercy. John in his hung over state was actually quite amused and the boy looked strangely erotic in the silky feminine panties. On his knees the boy hung on John’s legs and offered to blow him, rubbing on his crotch with his hand. John relented a simple “OK” and soon the boy had John’s shorts on the floor and knelt in front of him and hungrily began to suck on John’s cock.

The scene was bizarre and erotic and John’s legs were buckling from the blowjob and the dizzying hangover. He fell to the bed clearing a swath among the girlie magazines and the boy finished sucking off John to a raging climax. The boy lay next to John with his own raging hard on in the panties and he said nothing as he began to jack himself off again. Out of curiosity John reached over to see what another cock felt like and he touched the boy’s cock in the silky panties. The boy let go of his own hand and it was only a few swipes of John’s hand before the boy’s cock was spewing cum all over himself. Then in shock, realizing what had happened John got up and fled the room to resume his original quest.

John since that one incident proceeded to snuff it from his memory and pretend it never really happened or that it was a drunken dream. However about three years before meeting Bobby, John was out of town at a convention and a colleague joined him one inebriated evening in his hotel room. He was an attractive younger man who came on to John and kissed him and they jacked each other off. The incident fueled John’s bisexual interest leading to his attraction and curiosity with Bobby.

John was a very fit and trim 6”3” 200 guy who kept in good shape and had a lovely huge manly cock. As Bobby kissed him on the couch their clothes melted off and the very lithe and feminine Bobby and the masculine athletic John soon were naked in bed making love. They kissed and writhed in naked gay fondling, jacking, stroking, fingering and humping cocks together. Being naked with such a masculine well-built man enraptured Bobby. John’s cock was very large with a beautiful helmet head and bulging veins on its throbbing shaft nestled into a forest of dark hair. The feeling and aroma of such a lovely tool and being naked with this man confirmed to Bobby what he already knew by now, that he was more gay than not.

John sucked his first cock, Bobby’s lovely boyish boner. The sexual newness of the experience thrilled him, and in his gay lust actually enjoyed the warm creamy cum that his sucking produced. Bobby by now had come to grips about his sexual being and reciprocated by sucking off John’s massive cock. Bobby gnawed lovingly on the beast and rubbed his face all over it, relishing the pure manly scent and taste of John’s cock. Bobby affectionately made love to John’s cock and used his talented warm wet mouth to stimulating effects. John had rarely been so aroused and when he came Bobby swallowed some of it then jacked the rest the huge load of the handsome tool all over his face and chest enjoying the warm white cum as it sprayed on him.

They made love twice more before morning light with John experiencing the thrilling feel of fucking such a smooth & feminine boy like Bobby in his tight hole and smooth shaved legs. After Bobby left that morning he was again certain that he would never see John again. It was about two weeks later that John called Bobby at the shop, but again Bobby played hard to get. John asked if they could get together after work for a drink and Bobby agreed.

Being married, John really didn’t have any place to continue a sexual relationship with Bobby. John was certain his wife was having an affair. She didn’t work, had tons of free time and John was fairly certain by now that she had only married him for his money. Their sex life was infrequent and unexciting so this whole new bisexual world with Bobby was extremely appealing. If he was going to get a divorce he didn’t want to give her any unwanted ammo for it & did not particularly like the idea of being found out having a gay affair.

Bobby and John had drinks and chatted about their lives, John telling Bobby about his wife and Bobby telling John about his interludes with Peter and Yvette. Hearing about the handsome Peter perked John’s interest and when Bobby coyly told about his bath and lingerie session with Yvette it sparked his memory of the day with the frat brother in panties and all the girlie mags.

“Would you dress up for me?” John asked.

“Depends” said Bobby. “We really don’t have any place, as far as I can tell”

“What’s your place like, Bobby”?

“Well I have a straight roommate, and I really haven’t let on that I like to sleep with guys. Do you want to see my place? I’m sure it’s a hole compared to where you live”.

“Want to show me?” John asked, hoping maybe to be alone with Bobby for a while.

“If you want, but we can’t do anything there,” Bobby informed John. They headed over in John’s auto, with Bobby remarking what a set of wheels - it was power everything, leather seats, tinted windows. Bobby showed John in to his ancient apartment, though neat, the battered, dusty faded couch, musty carpet and peeling walls led John to give Bobby his own small apartment so they could continue their relationship in comfort and privacy.

**************** Bobby had his hand on Peter’s leg, rubbing it gently as he talked. He looked as sultry look directly into Peter’s eyes and before Peter had a chance to respond Bobby leaned over to kiss Peter, rubbing one of his hands over Peter’s crotch as he kissed. Peter had trepidation about continuing a sexual affair with Bobby, but with getting high and the spontaneity of Bobby’s actions his cock grew from the rubbing and from the gay kiss. Bobby broke the kiss and started to undo Peter’s jeans to release his cock. As Peter’s cock sprang free and hardened to Bobby’s touch Peter thought what the heck and pulled off his sweater and shirt revealing his naked chest.

The slight chill in the air added to the tingling stimulation he felt as he stood and pulled his jeans off. He stood naked in front of Bobby as Bobby engulfed Peter’s cock and eagerly began to make love to it with his mouth. Peter’s handsome cock swelled from the stimulation and he began to pump it in and out of his loving friend as Bobby caressed the cheeks of Peter’s sweet ass. Peter felt so free standing there naked getting his cock sucked by the mysterious Bobby who had by now removed his own shirt and jeans and Peter was surprised to see Bobby’s hard cock and ass encased in a silky pair of flowered panties. Bobby pressed Peter’s cock against his face and then licked Peter’s balls then went back to rubbing the sweet cock all over his face to savor the manly cock scent before returning it to his mouth, sliding his lips over the stunning mushroom head and engulfing it as deep as he could eliciting a shudder from Peter.

As Bobby continued to suck off Peter and fondle his ass, Peter guided Bobby’s fingers to his sensitive little rosebud opening. Bobby got the message and carefully fingered Peter as he hungrily sucked on the splendid cock. Of all the boys and men Bobby had ever been with Peter held a very special place at the top as one of his favorite lovers. As Bobby tenderly fingered Peter’s ass, his blowjob was bearing fruit as Peter held onto Bobby’s hand that was fingering him and he began to jerk crazily in and out of Bobby’s mouth as Peter stood there by the couch and Bobby knelt before him. Peter’s came so hard it bordered on being painful and his hot jizz erupted in a torrent into Bobby’s eager mouth. Peter’s knees buckled and he fell onto the couch as Bobby finished him off.

Peter nearly passed out and he lay there a bit to collect himself. Bobby climbed up over Peter and knelt over Peter’s chest, thrusting his cock against the silky panties as Peter reached up to fondle Bobby’s silk-sheathed cock. Bobby was quite aroused and a few long, firm, palming strokes was all it took to erupt his pent up excitement. Cum poured out over Peter’s hand up onto Bobby’s stomach and then down onto Peter’s chest in white, warm puddles as Bobby gasped and moaned and Peter smiled, still quite sated from the unexpected and tremendous sexual encounter.

As Peter left and headed home the same cycle began to repeat itself. It started with a bi fantasy, anticipation, arousal, tingling fear and self doubt, renewed arousal, intense desire, casting aside of anything but the sexual feelings, the intense and pleasurable gay sex, then only to be followed by doubts and guilt about what he had done. Today was a little different because he hadn’t anticipated it, it just happened as he unexpectedly ran into Bobby. Bobby had given Peter his number and told him that John would love to meet him and knew it would be cool with the three of them together, but he with his guiltiness and his love for Yvette he doubted that that would happen.

Months would pass and Peter’s guilt subsided to nothing and he allowed himself a few bi fantasies jacking off or when he made love to Yvette. In May Yvette left for a few days to visit family and Peter could not join her. The first day alone he allowed his bi fantasies to run wild when he jacked off and he even pulled out the dildo to assist in his bi naked pleasuring of himself. By the second night his arousal grew and he contemplated calling Bobby. His fears made him relent and he contented himself with masturbating to his girlie mags and bi novellas. The third day his arousal and curiosity grew to the point where he called Bobby from work. Bobby was very happy to hear from him and said to come over after work and that he would see if John could make it.

As Peter headed over to Bobby’s he felt possessed and drunk in desire and anticipation as the cycle began anew. He was so focused on what he was about to do he almost felt that strangers on the street knew what his gay intentions were as he continued over to Bobby’s apartment. As Peter walked down the hallway to Bobby’s door it was nearly déjà vu to what he felt when he went to see Adam. Bobby greeted him and the two boys partied a bit with some wine and weed till John showed up. After his arrival and the introductions John told himself that Bobby was entirely right, Peter was one of the sexiest and desirable young man he had ever seen. Bobby sat between them on the couch and laid his hand on Peter’s leg as they partied a little more. Peter was very nervous, but he tried not to let it show.

Bobby eventually nuzzled Peter’s neck and whispered, “Lets do it” and led him to Bobby’s large bed. Peter and Bobby undressed each other as John disrobed next to them. Soon there were three very different nude males standing and caressing each other. Bobby in his kinky femininity wore silky panties and stockings. The other two were naked, handsome and masculine and excited by the erotic rendezvous. Peter was a gorgeous and sexy young man, but at 40 John was still a trim, slim athletic nice-looking man who towered over the other two boys.

John was a man in every sense and his cock was much larger and fatter than anything Peter had ever seen in person. John’s cock swelled in anticipation and he placed Peter’s hand on it to let Peter feel the massive manhood. John likewise felt Peter’s cock grow to his touch as he marveled at this emerging gay threesome. John rubbed his cock into Peter’s body and shivered at the sensation of a new boy lover. Peter was entranced at the size of John’s cock and he pulled away to admire and jack on it some more. Peter’s cock was so hard from playing with John’s cock that he barely noticed Bobby tenderly rubbing both of their asses.

Peter fell to the floor to feel the manhood in his face. He rubbed with both hands on the huge cock and stared at the phallic beast pointing out, beckoning his lips. He was drawn to this masculine timber growing out from a forest of manly hairs and when Peter rubbed his face all over it and it stank a stimulating manly smell like no other that he had known. He and he licked up from the balls, smelling and licking up the veined shaft with his lips and nose drinking in the captivating scent of pure masculinity. John was astonished at the sight as Peter worshiped the huge phallic deity and began to slip the now sticky, pre-cum coated helmet head in his mouth.

John shuddered as the tender boyish lips covered his cock and Peter’s mouth opened to receive the throbbing hard-fleshed monster. Peter was obsessed with the taste, smell and sensation of this huge manly cock. He wondered if he might really be gay he enjoyed it so much. John slowly pumped in and out of Peter’s mouth, careful not to gag the boy with its size. John pulled Peter up by the shoulder to fall on the bed. John stretched out on the bed and Peter went back to hungrily sucking on the wonderful hard cock. Bobby went up to John and they kissed and John stroked Bobby’s panty covered cock as Peter gnawed lovingly yet ravenously on the huge meaty, hairy pole.

John relished this encounter with his gay two lovers and enjoyed it as Peter sucked his cock, licked his balls, rubbed his face all over it, and then resumed sucking on the pulsating manhood. This went on for quite some time till John’s arousal could be held back no longer. Peter’s eager boyish mouth had worked its magic on the cock and soon would get his reward. John moaned and arched his back thrusting his cock up more into Peter’s mouth, who really could barely fit in a third of the beast. John’s meaty pole began to pulsate cum into Peter’s mouth in hard, hot blasts. Peter took what he could, but to not gag he pulled off and jacked the huge cock spurting cum over John’s stomach, then put his mouth back over it to taste some more of the creamy juices of gay passion.

John was exasperated. Though Peter was not completely gay and had only sucked on two cocks before this one, John experienced truly the best blowjob of his life. Peter was now harder than ever and he rose up over a sticky cum coated John and kissed him with all the passion he had, rubbing his steel hard cock into John’s sticky flat stomach. As they kissed there Bobby knelt by the kissing lovers and they both rubbed on his cock through his silky panties. Peter was mad with cock lust and he pulled Bobby closer and pulled down the panties. His mouth found Bobby’s cock and had no problem engulfing the entire thing down his throat. Bobby pumped into Peter’s mouth as Peter and John fondled Bobby’s ass. As Peter slipped his finger into Bobby’s rosebud, Bobby lost it and his cock spewed his cum out into Peter’s eager mouth.