Learning To Swing Both Ways Ch. 12

Cliff also had had his share of one night stands with women he met in Rome and in other cities that he traveled to. He had never ever thought that he would have sex with a guy. He had long dismissed the blow jobs he got from the gays in D.C. as he was getting all he wanted with the women and girls in Rome.

MEETING ENZIO

On a Saturday morning after thinking about the girls he fucked and masturbating in his bunk, Cliff decided to walk around Rome and see if he could pick up a chick. He took in the sights visiting the Piazza di San Pietro, the Trevi fountain, Spanish steps, the Roman Forum and of course the Coliseum. It was after lunch when he reached the Coliseum and people were walking around inside. Cliff opted not to go with a tour group as he wanted to check out the babes. As he walked around he noticed a very pretty slim Italian checking him out. He seemed to shadow Cliff no matter where he went.

At one point Cliff thought he saw him put him finger in him mouth as if he was sucking a cock. Cliff ignored it at first but then he did it again. This time was no mistaking the signal or intention. He was clearly offering to suck Cliff's cock. Cliff approached the pretty young man and then he turned and beckoned Cliff to follow him. Cliff was cautious and he made sure that it wasn't a set up and that he was walking into a trap.

Cliff followed him to a secluded part of the Coliseum and they ducked behind a wall. Once behind the wall he dropped to his knees, opened Cliff's pants and pushed them along with his skivvies down to his ankles. Cliff's rock hard 8+" cock sprang free and bobbed in the young Italian's face. He began kissing Cliff's cock and running his tongue up and down the full length of it eventually taking it in his mouth. He gave Cliff the most incredible blow job, one equally as good as any of his female lovers. He would bring Cliff to the edge and then slow down delaying the ejaculation as long as possible. He tested his gag line deep throating Cliff as he handled his balls lovingly.

Cliff couldn't hold it any longer and he warned him that he was going to cum. The pretty young man went right on sucking Cliff as he blasted volley after volley of cum in his mouth. He kept swallowing rapidly and he did not miss a drop. He continued to suck Cliff draining and cleaning his cock of any trace of sperm. When he started to nibble on Cliff's dick head his knees got weak and Cliff had to pull him off before he collapsed. Cliff was drained and he pulled up his skivvies and pants as he didn't want to get caught with them around his ankles.

"Would you like to get a glass of wine?" the young pretty Italian asked in a soft voice.

"Sure," Cliff accepted.

They left the coliseum and walked a few blocks to a café. They both had a glass of red wine as they sat outside and chatted as they watched people walk by. His English was pretty good and Cliff's Italian was at about the same level so they able to converse fairly well. He asked Cliff if he enjoyed his blowjob then they exchanged names. He called himself Enzio. Cliff was still stunned as he had just had one of the best blow jobs in his young life.

The conversation continued and Enzio explained that he enjoyed sex with both men and women. Enzio was a pretty boy, very feminine and could easily pass for a girl. He was about 5'7," 140 lbs, very black hair cut short but covering his neck. At 19 years old his skin was hairless and flawless. He had shapely legs and an ass most women would kill for.

We had another glass of wine and Cliff was pretty horny by the time they finished it. Enzio shared some stories with Cliff that made his cock hard. Enzio then asked if Cliff would come to his room. Cliff agreed as he was actually looking forward to another blow job from him. Enzio and Cliff walked a long way to Enzio's apartment. Cliff was surprised when Enzio said he wanted them both to be naked as he had never been completely naked with another man. However they both undressed as Enzio desired. Enzio sat on the edge of the bed and drew Cliff in toward him. He caressed the back of Cliff's legs and cheeks of his ass as a warm, wet, wonderful mouth began sucking on his cock. Cliff was so horny that he almost shot his load right then and there. Enzio was massaging the head of Cliff's cock against the roof of his mouth. He circled Cliff's cock with his tongue and scraped it lightly with his teeth. Cliff felt the light scraping of Enzio's teeth and his cock felt as hard and long as it ever had felt in his life and Cliff sensed that he was going to shoot.

Enzio took the cock out of his mouth and looked up at Cliff as he stroked the entire length of it and massaged Cliff's bloated balls. At that time Cliff felt longer than my 8+" and bigger around then 5+". Enzio put it back in his mouth and then took it out again then he gently blew on it as his fingers continually massaged Cliff's balls. He tickled Cliff's cock head with his tongue and teased the pee slit. Enzio was bringing Cliff up and down and he was close to cumming few times. Enzio seemed to know when Cliff was getting close, and he would do things making him last longer, torturing him in the process.

Enzio then took the cock all the way into his warm wet mouth. He swirled his tongue around the length of the shaft, nibbled on the cock head and sucked it hard. Enzio reached under Cliff's balls and rubbed the hardness between the balls and the anus. Cliff could feel his cock thickening and he knew he was going to cum. There was no stopping Cliff this time. Enzio grabbed Cliff's ass cheeks with both hands as Cliff exploded in his mouth. Cliff fired round after round of cum into his mouth and Enzio sucked and swallowed as fast as he could. The force of shooting his load was so intense that it almost hurt. Cliff lost track of time for awhile and he just held onto Enzio's head as his cock was milked for every drop.

Cliff's legs were weak and he had to sit down. He sat on the edge of the bed and Enzio knelt down between his knees keeping the cock in his mouth. Enzio massaged Cliff's balls as he continued to suck the cock clean until it softened and left his mouth. Enzio continued to lick and kiss Cliff's cock sending chills and shivers through his body.

Enzio left Cliff on the bed and he went into the bathroom. Cliff slowly recovered from what was one of the most intense ejaculations ever. Cliff then got up and went into the bathroom. Enzio was standing naked by the sink and Cliff patted him on his shapely ass.

Cliff said, "That was incredible, thank you."

"I'm glad you liked it," Enzio replied with a grin.

After using the bathroom, Cliff walked back into the bedroom. To his surprise Enzio was in bed on all fours with his curvy bubble butt stuck up in the air. Cliff had expected to get dressed and leave but then he could feel a tingling in his loins as he looked at Enzio's hot ass. Enzio's body was delicate, hairless and flawless and he looked like a girl.

"I would like you to fuck me," Enzio said in a sultry voice. "You would like to fuck me like a girl, wouldn't you?" he asked.

Cliff's cock was hardening and he approached the bed. Cliff knelt behind Enzio and began to caress his beautiful ass. Enzio handed Cliff some lotion and asked him to get his ass ready for Cliff's cock. Cliff put an ample amount of lotion in his hands and rubbed it all around Enzio's bung hole. Then Cliff inserted first one finger then two fingers preparing him for his cock.

Cliff was no stranger to preparing female assholes for his cock but this was the first time he was preparing a pretty young man's bottom. However as Cliff sawed his fingers in and out of Enzio's anus he was getting turned on by the thought of burying his cock in the shapely ass. Cliff moved closer to Enzio and lined up the head of his cock with the anal opening and began to ease it into to him.

Enzio cautioned, "Go slow you are very big."

Cliff spat on his hand and rubbed his saliva all over his cock which made it very slick when combined with the cream. The cock head cleared his sphincter and Cliff fed it to Enzio a little at a time. The ass chute was warm and tight as Cliff went deeper and deeper into him. Soon Cliff was all the way in Enzio's ass and he started a slow fucking motion. Cliff continued to pump the curvy ass with deep, long, deliberate thrusts as he caressed Enzio's smooth round ass. In this position Cliff could only see his cock gliding in and out of Enzio's sweet shapely ass. Since he could not see Enzio cock or balls, Enzio looked like a pretty girl with a big cock in her ass.

Enzio asked Cliff to fuck him harder and quicker. So Cliff picked up the pace and he started pounding Enzio's ass faster and faster. Cliff's balls started bouncing off of Enzio's buttocks and Enzio was moaning with each thrust of the big cock. Cliff could feel his ejaculation building and he knew that any moment he would shoot his seed into his first male ass. Cliff tried to make it last as long as possible but once Enzio started to contract his sphincter, Cliff lost it.

Cliff fired a barrage of cum in Enzio's ass filling it to overflowing. As he continued to fuck him, Cliff's jizz backed up in Enzio's rectum and began to ooze out flowing over his balls. Enzio used his talented sphincter muscle to milk the cock and drain it of all its seed. Cliff didn't think that he would ever be soft again as he remained hard in Enzio's tight heath. The milking action weakened him and he collapsed on top of Enzio's body.

Enzio flattened out on the bed with Cliff on top and the cock still in his ass. They eventually moved to their sides and lay next to each other exhausted. Cliff could see the bed sheets where Enzio had shot his load sometime during the fuck session. They both relaxed and sometime during their rest the cock softened and slipped from Enzio's asshole. Enzio laughed when the wet pecker slid across his buttock. Enzio asked if Cliff could stay the night and he accepted. Cliff would never have imagined that he would have had suck great sex with a man and then agree to spend the night with him.

That night and Enzio curled up against Cliff with his ass pressing into Cliff's pubes. Cliff had draped an arm around him and they cuddled as if man and woman. Sometime during the night Cliff awoke with an erection and he eased it into Enzio's ass. They fucked lying on their sides with a slow gentle rhythm until Cliff unleashed his fourth load of the day the second in Enzio's ass. They fell back asleep with Cliff's cock still sheathed in Enzio's curvy hot ass.

ENCORE WITH ENZIO

The next morning Cliff awoke to a warm wet sensation around his cock. Enzio was taken with Cliff's impressive cock and he spent a lot of time kissing it and licking it. Enzio was driving Cliff crazy and Cliff desperately needed to cum. Enzio knew that Cliff was ready to shoot so he lowered his mouth to Cliff's cock and took it as deep as he could. Cliff's ejaculation was forceful and the first shot bounced off the back of Enzio's throat. Enzio swallowed quickly but the next several spurts came so fast that he had to pull off of Cliff's cock. Enzio stroked the big rod as three more shots came out of the end and shot into the air. Enzio marveled at the youthful discharge and he was glad that he didn't try to swallow the entire load. Enzio made a metal not that the next time he wanted to feel that initial ejaculation in his ass. Enzio put Cliff's cock back in his mouth and sucked it dry keeping Cliff hard.

Cliff was now ready to fuck Enzio and he told Enzio to get on all fours. Cliff got the cream and greased up his cock. Then he greased up Enzio's asshole and he marveled at the shapely ass on Enzio's small frame. Cliff noticed that Enzio's skin was brown all over and that he had no hint of any tan lines. Enzio had flawless smooth skin and his body was hairless. Cliff also noticed for the first time that Enzio's cock was only about three or four inches in length. Enzio looked good on all fours as he waited for Cliff's cock to penetrate his ass. Cliff took his time lubricating Enzio's ass and he liked the submissive posture that Enzio presented. Enzio had his head down on his hands which were folded on the bed. Enzio's ass was elevated and his back was arched emphasizing the curvy shape of his ass. Enzio looked perfect and he presented exactly the image that Cliff liked to fuck.

Cliff moved close and slowly eased his cock into Enzio's ass. Enzio groaned slightly with the penetration and his sphincter stretched to accept the big cock. Once past the sphincter Cliff fucked Enzio slowly until Enzio's ass opened up and was able to take the big thick cock. Cliff then picked up the pace and soon his hips were slamming into the petite Enzio. Enzio's cute ass would jiggle each time Cliff thrust into it and Cliff loved the effect. Enzio then reached between both of their legs and fondled Cliff's balls. Enzio was able to reach back far enough to stroke Cliff's perineum and fondle the taut ball sac. Cliff felt his ejaculation building again and he knew that he would dump a good sized load in Enzio's ass. Enzio felt Cliff's body stiffen and make one final thrust as Cliff buried his cock in Enzio's ass. Then Enzio felt cum surge into him and he felt Cliff's cock throb with each release. Enzio couldn't remember the last time he felt that much cum in his ass.

Enzio's sphincter involuntarily clenched and unclenched as it massaged Cliff's cock and drew every drop of cum from the shaft. Cliff kept pressed against his new lover and let his cock be milked dry. Enzio couldn't hold his position any longer and he collapsed forward on the bed. Cliff followed Enzio down and lay on top of Enzio with his cock still buried in Enzio's ass. He felt Enzio's smooth hairless skin against his own and he liked the feeling. Cliff remained on top of Enzio until Enzio begged him to get up. Cliff didn't realize it but he had been crushing Enzio's smaller body. Cliff had gotten lost in the moment as Enzio's ass muscles tightened around Cliff's cock. Cliff then rolled to the side and his softening cock slipped from Enzio's dilated asshole.

Enzio remained on his stomach face down on the bed as he recovered from being thoroughly fucked. Cliff looked over at Enzio and he wondered if Enzio had cum. Then Cliff looked at Enzio's ass and he could see cum oozing from it. Cliff was tempted to finger Enzio's asshole and push the semen back in. Cliff started by caressing Enzio's curvy smooth ass and then he played with his asshole. Cliff pushed his finger into Enzio's cum filled hole. Enzio wiggled his ass in response as Cliff played with him.

Enzio then pushed himself up on all fours giving Cliff better access. It was then that Cliff noticed that Enzio had cum on the bed. He could see the wet spots on the sheets and Cliff knew it was from Enzio's cum shots. Cliff felt his cock getting hard again so he moved back behind Enzio. Cliff eased his cock back into Enzio's ass for a second time and he knew he would last longer this time since he had already cum twice. Cliff fucked Enzio for what seemed like an hour until he finally came again. Once again Enzio collapsed on the bed in the pool of his own cum from his second ejaculation.

"Oh Cliff, I don't know if I have ever been fucked like that," Enzio cooed.

"I'm glad you liked it because I loved fucking your ass," Cliff told him.

"I think that I messed on my bed sheets," Enzio said with a laugh.

They were both exhausted so they stayed in bed and somehow they dozed off again. Two hours later Cliff woke up with an erection. Enzio's back was pressed into the front of Cliff's body and Cliff had one arm thrown over Enzio. Cliff's cock was nestled in the crack of Enzio's ass and it seemed natural for Cliff to slide his cock into Enzio's asshole. The fit was snug but it went in and Cliff fucked Enzio slowly until he came in Enzio's ass for a third time. Cliff left his cock in Enzio's ass and they both fell asleep again. Sometime later Cliff's cock slipped from Enzio's ass as they both slept. It was nearly 2:00 PM when they woke up the second time.

"Cliff, I would be happy to show you around my neighborhood. I also know of a great place to eat dinner," Enzio offered.

"Sounds like a plan. Let's get dressed and then I'll let you show me around this part of the city," Cliff agreed.

Following a tour of Enzio's neighborhood and a fantastic dinner Enzio and Cliff returned to the apartment. They were both exhausted from the day that started out with a sexual marathon and continued with lots of walking. They went right to bed and although Cliff was content to wait until morning for more sex, Enzio wanted to suck Cliff's cock. So Cliff stretched out naked on the bed and let Enzio have his way. Once again Enzio used all his talents and he soon had Cliff cumming. Enzio stayed with the ejaculation and swallowed every drop of Cliff's juice. Then they curled up naked together and slept in a spoon position. Enzio's back was to Cliff and Enzio could feel Cliff's cock even though it was soft. During the night Cliff got an erection but he didn't fuck Enzio. Cliff just let his erect cock rest in the crack of Enzio's ass.

THE WEEKEND END

The next morning Cliff was awake first and he quietly got out of bed and went in the bathroom to pee and take a shower. Cliff was letting the warm water cascade over his body when Enzio joined him in the shower.

"Got room for me?" Enzio asked.

"Plenty of room," Cliff replied.

The two of them then began to wash each other. Cliff washed Enzio's body and paid particular attention to Enzio's ass. Cliff stood behind Enzio and washed Enzio's chest and abs. Then Cliff's hands made their way down to Enzio's ass. Cliff cupped the inviting buttocks in his hands as he soaped up Enzio's ass. Then he fingered Enzio's asshole and soaped up his own cock. Enzio leaned forward slightly placing his hands on the shower wall and arched his back so that his ass pushed back toward Cliff. Cliff eased his cock into Enzio's soapy asshole as he held onto Enzio's hips.

Enzio groaned seductively as the big dick entered his asshole. Cliff fucked him slowly and watched his cock slide in and out of Enzio's shapely ass. Cliff was so turned on that he felt his ejaculation building quicker then he planned. There was no stopping him and his balls tightened as he unloaded in Enzio's ass. Cliff held onto to Enzio's hips and drove his cock deep into Enzio's asshole. Enzio felt the hot cum fill his asshole to overflowing and instinctively used his sphincter to milk Cliff's cock. Enzio had wanted to feel Cliff's first load of the day in his ass and as expected Cliff flooded Enzio's rectum.

Cliff stayed hard and kept fucking Enzio. Cliff could feel his own semen surround his cock as he continued to fuck Enzio's ass. Cliff sensed that he would stay hard and he was pleased that he could continue to fuck Enzio's ass. Enzio realized that Cliff would fuck him until he ejaculated again and Enzio began to stroke his own cock. Enzio wished that Cliff would jerk him off while he fucked his ass.

"Cliff, would you play with me? Please play with my cock. Stroke it for me. Make believe it is a girl's big clit," Enzio begged.

Cliff had never touched a cock other than his own but he honored Enzio's request. He grabbed a hold of Enzio's cock and jerked him off as he fucked Enzio's ass. It was weird for Cliff to be holding a cock other than his own and the contrast in size was an odd feeling. Cliff lasted much longer this time but he still felt a huge orgasm building in his balls. Just as Cliff came in Enzio's ass a second time, Enzio screamed that he was cumming. Cliff stroked Enzio quicker and he watched over Enzio's shoulder as Enzio ejaculated. Enzio's cum oozed out of his cock and trickled over Cliff's hand only to be washed away by the shower water. Cliff actually liked feeling Enzio cum and watching the spunk ooze out of Enzio's cock.