Curious Guy Becomes Bi-curious Pt. 02

Author's note: This story was requested by a young man who shared his experience with me and asked me to write about it. I chose not to post any more stories under the title Honoring Reader Requests. All characters in this story are at least 18 years old. I decided to break the story up in to chapters since it started to get a little too long.

Chapter Two – Jimmy Takes His Bi Side To The Next Level

JIMMY STRUGGLES WITH HIS DESIRES

Jimmy was struggling with his new found desires. He never thought that he would ever be interested in having sex with another guy. However watching those hot looking gays guys in the movies jerk each other's cock, suck com and fuck shapely asses had made Jimmy incredibly hot. One night he dreamed that he walked into a sauna and saw Billy and Henry kissing and stroking each other's cock. Then the image Henry and Billy became his neighbors Roy and Jack. Then the dream got blurred as Jimmy seemed to move from one hot looking ass to another shoving his cock in each one. Then Jimmy seemed to cum endlessly in his dream and showered the asses with his seed. Jimmy woke up with his erect cock in his hand and he jerked off that morning. Cum flew all over Jimmy's body and some of it landed on his pillow.

It was Saturday morning and Jimmy got to sleep in that morning. Later he would head to his neighbor's house and perform his house sitting duties. Jimmy knew that he would not be able to watch porn that day since his parents were at home and they would get suspicious if he stayed too long at the neighbor's house. Jimmy lay in bed and thought about his fellow cheerleaders. He loved holding the one girl Christy up in the air with his hand on her ass and he loved looking up at her shapely legs. Christy was cute with great legs and a nice ass but she was dating one of the basketball players. Jimmy found himself wondering whether Christy was getting fucked in the ass.

Jimmy then turned his thoughts to Bruce and Colin who were also cheerleaders. He had never looked at them sexually before but now he thought about both of them having great looking asses. Jimmy suspected that Bruce was gay as he was never around the girls and recently in seemed that Colin had started hanging around with Bruce. Jimmy thought about how to approach Bruce but then he dismissed it as he was nervous. If Bruce and Colin were gay, Jimmy didn't want the others at school to think that he was too. Jimmy struggled with his thoughts and then he decided to go into Chicago for the day.

Jimmy had heard of a section in Chicago that was notorious for being gay and Jimmy thought that he could remain anonymous there. He got out of bed, showered, dressed, ate breakfast and then did his house sitting duties before lunch. Jimmy then headed downtown Chicago to explore the city. He suspected that is he had a gay encounter there that he would know for sure whether he liked it or not. Jimmy was not interested in sucking a cock or getting fucked but he knew that he would like to have his cock sucked or fuck a hot looking ass. Jimmy decided if the guy had a nice cock that he might jerk the guy off. All sorts of thoughts went through Jimmy's mind as he headed into the city.

An hour later, Jimmy was walking the streets of Chicago in the prominently gay section of the city. The good thing was that there were a lot of cool shops in that section and a lot of people who were not gay shopped there. Jimmy just tried to blend in as he checked out the area. Jimmy noticed that in addition to the neat shops there were also adult novelty shops with video arcades. Jimmy tried to enter one but he was carded and being only 18 he was denied entry. He also noticed other guys checking him out as he walked around but that made him very nervous.

Then Jimmy noticed a younger guy walking ahead of him who looked very hot from behind. The guy was wearing tight slacks that showed off his curvy ass. Jimmy then saw the guy look over his shoulder at Jimmy and then slowed his pace. The guy then moved over to a store window and pretended to be interested in the something as Jimmy approached. The guy then turned to Jimmy smiled and spoke.

"Hi, you're new around here aren't you?" the cute blonde guy asked.

"Just visiting, I live in the western suburbs. It's my first time in this area of the city," Jimmy replied trying to sound mature.

"I see. Have you found what you are looking for?" the blonde asked.

"Oh I'm just looking around at the different stores, kind of browsing," Jimmy offered as an answer.

The blonde guy smiled and then stuck out his hand, "I'm Josh.

"Hi I'm Jimmy," Jimmy replied shaking hands with the handsome stranger.

"Do you like lattes?" Josh asked.

"Yeah, sometimes," Jimmy answered.

"There is a great coffee shop just up the street. What do you say that we stop for a cup of coffee? I would like to get to know you better," Josh offered.

Jimmy sensed where this was headed and as he looked at Josh he knew that he would be willing to fuck Josh or let Josh suck his cock. So Jimmy accepted the invitation, "Sure, why not, coffee sounds good."

Josh and Jimmy walked up the street to the coffee shop and when they entered Jimmy noticed that there were just guys in the shop. They sat at a table for two away from the window and then Josh walked up to the counter to order the lattes. Jimmy fished in his pocket for some money but Josh stopped him.

"That's okay the coffee is on me," Josh offered.

"Thanks!" Jimmy replied.

The waiter brought the lattes over when they were ready and Jimmy noticed the waiter's ass when he walked back behind the counter. It was hard not to notice as the waiter swished his hips and flexed his buttocks as he walked. Jimmy blushed a little at the waiter's behavior and then he saw Josh smiling at him.

"Alex has a nice ass and he is always showing it off," Josh whispered across the table.

Jimmy and Josh talked for almost a half hour and got to know a little more about each other. Jimmy learned that Josh was 21 years old and he was going to college in the city. Josh shared an apartment with another guy who happened to be out of town for the weekend. Jimmy got the impression that Josh was gay but the more time he spent with Josh the more Jimmy liked him.

Josh excused himself and then went up to the waiter and they talked in a whisper. The waiter shook his head agreeing with something and then Josh returned to the table. "Come with me Jimmy," Josh said softly.

Jimmy took a final slug of his coffee and followed Josh into the back of the shop. Jimmy looked at Josh's ass again as his new acquaintance walked in front of him. Jimmy wondered and secretly hoped that something was going to happen but Josh would have to make the first move. Josh opened a door and beckoned Jimmy inside. It was a storeroom and Josh locked the door once they were both inside. Without a word Josh dropped to his knees in front of Jimmy. He unbuckled Jimmy's belt and unfastened Jimmy's pants. He pushed Jimmy's pants down to his knees and then stroked Jimmy's erect cock through his underwear. Josh stroked Jimmy's bare thighs and took his time before he finally lowered Jimmy's underwear. Jimmy's hard cock leaped out as his underwear was lowered to his knees. Josh took Jimmy's cock in his hand and stroked it gently.

"Wow, you really have a nice cock," he whispered.

Then Josh lowered his mouth onto Jimmy's cock and proceeded to suck it. Jimmy was so charged that he knew that he would cum in minutes. Josh was an expert cocksucker and he held tightly to Jimmy's muscular buttocks as his head bobbed up and down. Jimmy put his hand on Josh's head as a signal that he was close.

"I'm really close. I'm going to cum," Jimmy whispered.

Josh was not deterred and he continued to suck on Jimmy's throbbing cock. Then he stroked Jimmy's perineum and fondled his balls sending Jimmy over the edge. Jimmy shot streams of cum into Josh's mouth and Josh kept his mouth glued to Jimmy's cock. He sucked Jimmy dry and Jimmy stayed hard as every drop of semen was drained from his cock.

Josh stood up and smiled at Jimmy and noticed that Jimmy still had his clothes around his knees and was still hard. "Would you like to fuck me now?" Josh asked in a whisper.

Jimmy just nodded affirmatively and the guy turned his back to Jimmy. Jimmy watched as Josh lowered his pants and underwear revealing a very curvy ass, just the type that Jimmy hoped to fuck. Josh reached back and placed some lube in his ass and then he handed the tube to Jimmy.

"Put plenty of that on your dick. I'm going to need it to be real slick to take your cock in my ass," he whispered.

Jimmy lubed his cock thoroughly and then he was ready to fuck his first male ass. Josh leaned forward, put his hands on the wall and pushed his ass toward Jimmy. The way Josh's ass was arched emphasized the curvy shape of it and Jimmy felt that familiar tingle in his loins. Jimmy stepped up closer to Josh and then eased his cock into the tight anus. The fit was snug and Jimmy took his time feeding his cock into Josh's ass. Jimmy would push in a little and then back out some each time going a little deeper.

"Oh man, oh man, oh, oh," Josh whispered as Jimmy continued to feed him more cock.

The Jimmy was balls deep in Josh's asshole and he began to fuck him. Jimmy began slowly but then picked up the pace. Soon he was sliding his cock almost all the way out and plunging it all the way back in. Josh grunted with every thrust and urged Jimmy to fuck him hard and deep. Jimmy was really into it now and his orgasm snuck up on him. All of a sudden he felt that familiar surge in his scrotum and he blasted a huge load into his new lover's ass. Jimmy shoved his cock all the way in and held it there as streams of cum filled Josh's rectum. Jimmy realized that the Josh was jerking himself off and when Josh ejaculated his anal muscles tightened around Jimmy's shaft. Jimmy looked over his partner's shoulder and watched as streams of cum shot out and splashed against the wall. Jimmy took note of Josh's cock and guessed it to be an average 5-6 inches. Jimmy stayed in the Josh's ass until his cock softened and slipped out by itself.

Jimmy pulled up his underwear and pants as Josh cleaned up the best he could. Josh wiped his own ass with a hanky and then pulled his clothes back up. He turned back to Jimmy and spoke.

Josh said, "That was really hot. Let's go to a bar up the street and get a drink."

"I'm only 18," Jimmy whispered.

"Don't worry, I know the owner," Josh replied softly.

Jimmy followed Josh to the bar and they sat in a booth. Josh got a couple of beers at the bar and as they sipped on their beers, Josh quizzed Jimmy about his life and sexuality.

"Jimmy I have to ask you a question. Was that your first blow job?" Josh asked.

"No I've gotten blow jobs from girls I dated," Jimmy answered.

"How did mine rate with those?" Josh asked with a smile.

"Just as good, well maybe better. The girls didn't let me cum in their mouth," Jimmy admitted.

"Did you like that? Did you like cumming in my mouth?" Josh pressed.

"Yeah, I did. It was pretty hot," Jimmy agreed.

"So am I your first guy? Have you ever fucked any of your girlfriend's in the ass?" Josh continued.

"It was the first time I fucked anybody in the ass and you are the first guy I have had sex with," Jimmy admitted further.

"So tell me why you became so bi-curious? Why did you come to the gay neighborhood?" Josh pressed on.

Jimmy was honest with Josh and told him about house sitting for his neighbors. Jimmy told Josh about the porn movies he watched and how hot the guys in the movie were. Jimmy admitted fantasizing about fucking the shapely asses of the actors as he masturbated during the movies.

"Some of those movies can be very hot and some have very hot looking guys with big cocks in them. I like the ones you described where the guys are so pretty and they seem to be making love rather than just having sex," Josh told Jimmy.

Then Josh advised Jimmy, "Don't get too friendly with your neighbors. They are too close to your home and from what you told me, your parents would freak out if you had sex with those guys."

Jimmy and Josh continued to get along and continued their conversation. After a second beer, Josh invited Jimmy to his apartment. Jimmy enthusiastically accepted the invitation so they finished their beers and headed back to Josh's place. Josh explained that his roommate was gone for the night but that he was returning tomorrow.

Jimmy and Josh entered the apartment and within seconds they were both naked and Jimmy was buried balls deep in Josh's tight asshole. Josh was flattened on the bed face down as Jimmy drove his 7+" cock deep into the bowels of his first male lover. Josh's ass moved under Jimmy but Jimmy's strength and drive kept Josh pinned under him. Jimmy's powerful buttocks clenched and unclenched as he pummeled Josh's ass. Jimmy's thick cock drove into Josh and then retreated until only the head remained in Josh's rectum. Josh felt the powerful shaft drive in and out of his anal passage like a piston causing Josh to cry out.

"Oh man your cock is so big in my ass, so deep. Cum in me again, I want to feel you shooting in my ass!" Josh exclaimed.

Jimmy continued to fuck the shapely firm ass driving his cock into the warm recess. Jimmy sensed his orgasm building in his balls and he knew that within minutes he would cum in Josh's hot ass. Jimmy felt the pressure in his scrotum just before he unleashed a torrent of semen into the shapely firm ass underneath him. Jimmy felt Josh's anal muscles tighten around the shaft and squeeze every ounce of spunk out of it. Jimmy stayed hard and he slowly fucked Josh's ass as the semen coated his shaft.

Josh sensed that Jimmy was up for another round and whispered, "Jimmy if you are going to keep fucking my ass let's roll on our sides."

Jimmy rolled to his side keeping his cock in Josh's ass as he pulled Josh to the side. Jimmy's hands wrapped around and caressed Josh's body. Jimmy ran his hands over Josh's breasts and tight abs as they moved toward Josh's pubes. The back of Jimmy's hand brushed against Josh's erect cock causing Josh to gasp. Jimmy then did something that he had only imagined doing; he took a hold of Josh's cock and began to jerk him off.

"No I'll do that. You do my tits. Squeeze my tits and pinch my nipples," Josh pleaded.

Jimmy gently pinched Josh's nipples and kept fucking Josh until they both came. Josh came two times before Jimmy came in Josh's ass again. The first time Josh ejaculated his cum shot passed his face and hit the headboard of bed. The second time he came his seed hit him in the face and neck. Then Jimmy lost it and dumped another powerful load in Josh's ass. It was the first that Jimmy had cum four times in one day with a sex partner but it had been quite a day of discoveries and great anal sex. The two of them rested on their sides as Jimmy's cock slowly deflated and slipped from Josh's asshole. By the time they were ready to get out of bed the spunk had dried on Josh's body.

"Jimmy I can't let you stay tonight, my roommate may come home early in the morning," Josh said almost with disappointment in his voice.

"I can't stay anyway. My parents would be worried about me if I didn't come home tonight," Jimmy told him.

"Will you call me the next time you come downtown?" Josh requested.

"Sure, give your number and I'll call you when I plan to come back to the city," Jimmy agreed.

Josh then let Jimmy use the shower. Jimmy then got dressed and headed back home. On his way home Jimmy still couldn't believe what he did. He had his first gay encounter and it had been terrific. Jimmy loved fucking Josh in his pretty ass and he loved the way Josh sucked his cock. Jimmy also liked the fact that Josh did not pressure him. Jimmy felt he still wasn't interested in cock but he had loved playing with Josh's smooth hot ass. Jimmy knew then that he would call Josh again.

JIMMY RETURNS TO THE CITY

The following week Jimmy continued his house sitting duties for his neighbors. Each afternoon he would watch his favorite scenes in the porn movies and jerk off. Jimmy would always lay naked on the bed and ejaculate at least two times. Sometimes he fantasized about Josh and made believe he was fucking Josh. Other times Jimmy imagined that he was fucking one of the porn stars.

Roy and Jack returned home the following weekend and they thanked Jimmy for taking care of the house and their cat. They gave Jimmy a great looking Gear sweatshirt from Aspen, Colorado. Jimmy loved the shirt and thanked his neighbors. Of course Roy and Jack had no idea what Jimmy really had to be thankful for.

A few weeks passed after Roy and Jack got home and Jimmy tried to get back to his previous lifestyle. He had a few dates and had sex with a couple of girls. Usually a blow job that ended in a hand job or he ended up cumming in a rubber when he fucked one of the girls. One girl freaked out when Jimmy touched her asshole so he didn't press that issue. Jimmy was certain that neither of the girls he dated would go for anal sex. Jimmy though about Josh and realized that he missed the sex with him. Jimmy decided to call Josh and see if they could get together again. Josh told Jimmy to come downtown the next weekend as his roommate would be gone. Josh told Jimmy that he could stay over on Saturday night if he wanted to. Jimmy was thrilled and he made the arrangements to visit Josh.

The week leading up to the weekend with Josh, Jimmy refrained from jerking off. He wanted to safe himself for Josh. The anticipation drove Jimmy crazy and a few times he almost gave in to his urge to cum. However, Jimmy wanted to surprise Josh with a big load. Saturday finally arrived and Jimmy headed downtown.

Jimmy went straight to Josh's apartment on Saturday afternoon. There was no need for preliminaries as Jimmy was horny and Josh wanted to be fucked. They both took off their clothes and got in bed. Josh loved Jimmy's impressive cock and he spent a lot of time kissing it and licking it. Josh was driving Jimmy crazy and Jimmy desperately needed to cum. Josh knew that Jimmy was ready to blow so he lowered his mouth to Jimmy's cock and took it as deep as he could. Jimmy's ejaculation was forceful and the first shot bounced off the back of Josh's throat. Josh swallowed quickly but the next several spurts came so fast that he had to pull off of Jimmy's cock. Josh stroked the big rod as three more shots came out of the end and shot into the air. Josh marveled at the youthful discharge and he was glad that he didn't try to swallow the entire load. Josh made a mental not that the next time he wanted to feel that initial ejaculation in his ass. Josh put Jimmy's cock back in his mouth and sucked it dry keeping Jimmy hard.

Jimmy was now ready to fuck Josh and he asked Josh to get on all fours. Jimmy used the lube that Josh handed him and greased up his cock. Then he greased up Josh's asshole and he marveled at the shapely ass on Josh's small frame. Jimmy noticed this time that Josh's skin was tan all over and that he had no hint of any tan lines. Josh had flawless smooth skin and his body was hairless. Jimmy also noticed that Josh's erect cock was about 5 or 6 inches in length. Josh looked good on all fours as he waited for Jimmy's cock to penetrate his ass. Jimmy took his time lubricating Josh's ass and he liked the submissive posture that Josh presented. Josh had his head down on his hands which were folded on the bed. Josh's ass was elevated and his back was arched emphasizing the curvy shape of his ass. Josh looked perfect and he presented exactly the image that Jimmy liked to fuck. He looked just like Billy in the movie.

Jimmy moved close and slowly eased his cock into Josh's ass. Josh groaned slightly with the penetration and his sphincter stretched to accept the big cock. Once past the sphincter Jimmy fucked Josh slowly until Josh's ass opened up and was able to take the big thick cock. Jimmy then picked up the pace and soon his hips were slamming into the smaller Josh. Josh's cute ass would jiggle each time Jimmy thrust into it and Jimmy loved the effect. Jimmy felt his orgasm building again and he knew that he would dump a good sized load in Josh's ass. Josh felt Jimmy's body stiffen and make one final thrust as Jimmy buried his cock in Josh's ass. Then Josh felt cum surge into him and he felt Jimmy's cock throb with each release. Josh couldn't remember the last time he felt that much cum in his ass.