Learning To Swing Both Ways Ch. 07bywalterio©
Craig Sanders and his girlfriend Trudy had planned to attend a swinger's get together at an all-inclusive resort in the Caribbean. At the last minute Trudy backed out but Craig decided to go without her. He decided that there would be plenty of other single swingers there and the trip was already paid for. Craig left for the Caribbean Island on a Friday afternoon and checked into the resort that night. Most other people would be arriving on Saturday the normal transition day for the resort.
It was nearly 10:00 PM when Craig decided to walk around and check out the grounds. The bar in the main building was open 24 hours so he stopped there first and got a Mudslide his favorite island drink. Craig then walked around the property and located all the pools and Jacuzzis. He walked along the nude beach which by then was vacant but the action in the nude Jacuzzi was something to behold. He didn't stay long as he didn't want to appear conspicuous but he stayed long enough to watch several naked couples engage in sex.
As Craig passed the pump house near the Jacuzzi he heard some voices and spotted some movement behind the building. Suspecting that others were having sex Craig's curiosity got the best of him. He quietly peered through the bushes to see who was behind the building. Craig was shocked to see three guys together with their bathing suits pushed down to just above their knees.
A cute almost pretty blonde haired guy was standing between two dark haired guys. The blonde had a cock in each hand and he stroked them both. The dark haired guys each had one of the blonde's buttocks in their hands as they kissed his neck and toyed with his nipples. Craig watched as the two dark haired guys maneuvered the blonde onto all fours. Then the blonde sucked on one cock as he got fucked with the other. Craig had never seen gay sex even in porno movies and he was mesmerized by the act. The three guys were so good looking with smooth hairless bodies that Craig found the scene to be very erotic. Craig watched them until the all ejaculated.
The guy fucking the blonde pulled out of the blonde's ass and shot his load onto the blonde's back and buttocks. Then he put his cock back in the blonde's ass and fucked him until his cock softened and slipped from the blonde's asshole. The other guy pulled his cock from the blonde's mouth and shot his load past the blonde's face onto his back and shoulders. Then the blonde took the cock back in his mouth and sucked it dry. Finally the blonde rolled over on his back and one of the dark haired guys jerked the blonde guy's cock. The blonde shot an enormous load onto his own body covering his chest and pubes.
At that point Craig moved away from the threesome and headed to his room stopping at the bar on the way to get another drink. Craig realized that he had a boner and he was surprised that the gay sex had got him so excited. Still he had seen enough for one evening. He hadn't even been there for two hours and he had witnessed multiple sex acts. Craig returned to his room and stripped off his clothes. Craig got in bed and slept in the nude. He eventually fell into a deep sleep as he was tired from the trip but not before wondering what was in the cards for him that week.
SATURDAY THE START OF A NEW ADVENTURE
Craig woke up Saturday morning with a raging hard-on. He was tempted to jerk off because he was so stiff but he resisted the temptation. Craig decided that he would save himself for later just in case he got lucky. He took a shower, dressed and made his way to the breakfast buffet. Craig was impressed with the variety and quality of the food. The fruits were so very fresh and delicious. Craig dined with some other people and learned that they were from Toronto Canada. They were very pleasant and attractive. Craig couldn't help thinking about the three couples after breakfast. Did they all come here to fuck each other, he wondered?
After breakfast Craig worked out at the fitness center, and then he showered again and had a light lunch from the buffet. Craig then decided to work on his tan lines and headed for the nude beach. He was well tanned except for where his bathing suit had blocked the sun. Craig had been warned about the Caribbean sun and he liberally applied sun block to his entire body. Craig stretched out on one of the lounge chairs and began to read a book that he had been intending to finish for some time.
Pardon me but do you mind if we sit here," a sweet voice asked.
Craig looked up and saw a very cute naked couple standing just a couple of feet from him. They looked like brother and sister. They were both about 5'6" tall with blonde hair and slender bodies. The woman had a cute figure with tiny breasts, shapely legs and a very nice ass. The man looked just like her except that he had a cock and he didn't have tits. Craig was convinced that he had seen them somewhere before but he couldn't remember when or where.
"Of course, please join me," Craig replied and smiled at them.
They set out their beach chairs next to each other and sat facing Craig. The man then spoke, "I'm Blake and this is my wife Sandy."
"I'm Craig, pleased to meet you," I replied.
"Are you here by yourself?" Sandy asked.
"Yes, my girlfriend bailed on me at the last minute," Craig replied.
"We are from Canada and have been her for several days. We're leaving on Monday," Blake replied.
"I am thirsty. Does anyone want anything? I am going to the bar," Sandy asked.
Blake and Craig both opted for vodka slushes which Sandy was having. She got up and walked over to the bar and Craig could not help but watch her as she walked away. Her cute ass swayed and rolled as she walked on the sand. Craig was embarrassed when he realized that Blake was watching him as he watched Blake's wife.
"Sorry, I am still not used to nudity on the beach," Craig apologized.
"I understand and she is beautiful to watch isn't she?"
"Yes she is," Craig replied embarrassingly.
It was just as bad when she returned carrying the three drinks. Craig looked at Sandy and took in her shapely legs, luscious thighs and very pretty blond pussy. Craig was afraid that he was going to get an erection if he kept looking at her. Sandy arrived and handed Craig and Blake the drinks. Craig took his and casually held it in his lap for a few seconds to cool his jets before he raised his cup and toasted the couple.
"To a great week for you," Blake said as they both raised their cups.
The three of them chatted for quite sometime that afternoon and we got to know each other very well. Craig learned that they were both 28 years old even though they didn't even look 21. Craig shared the story about his girlfriend and they both applauded him for vacationing without her. They suggested that Craig hang out with them since he was by himself and that he could sit with them at dinner and the evening entertainment. The next time they needed drinks, Blake went to the bar to get them. As he walked away from them Craig couldn't believe how much he resembled Sandy from behind. He was just as shapely and he had an ass that looked just like hers. With his blonde hair covering the nape of his neck he looked like a woman from the back.
It was then that Craig remembered where he had seen Blake and Sandy the first time. It was last night. Blake was the blonde guy with the two dark haired guys. Blake was the one sucking cock and getting fucked. Craig couldn't believe that Blake was married to a hottie like Sandy and he was having sex with other guys. Craig then remembered Sandy from the nude Jacuzzi. She was the blonde who was eating pussy and getting fucked at the same time. Craig realized that they were both bisexual and obviously very active outside their marriage.
Blake returned with the drinks and they talked some more and eventually Craig got very comfortable with the two of them. It was Craig's turn to get the drinks next and as he stood up both Sandy's and Blake's eyes went right to his crotch. It was obvious that they were both checking out Craig's package. Craig went and got the drinks and as he did he wondered where things would lead with Blake and Sandy. Craig returned with the drinks and handed them to Blake and Sandy. Sandy stared at Craig's cock as he leaned over to hand the drink to her then Craig handed Blake his drink and sat back down.
When it was time to go and get ready for dinner, Blake told Craig that they would meet him at the restaurant and that they would sit together. Blake and Sandy walked ahead of Craig as they left the beach and again Craig marveled at Sandy's ass. Craig was also watching Blake as he walked along side his wife and it was hard to tell them apart from behind. Craig felt his loins stir as he watched this sexy pretty couple walk across the sand. Craig then returned to his room to get ready for dinner.
Blake, Sandy and Craig dined together that evening and then they hung around for the entertainment. That night the resort had an Elvis impersonator who was quite good. The three of them enjoyed listening to all the Elvis songs and then the dance floor was opened up during his second set. Sandy wanted to dance to the slow songs but Blake said he wasn't in the mood. Sandy asked Craig to dance with her and they stayed on the dance floor for five straight slow songs.
During the third song Sandy moved her leg between Craig's and they danced so close that a ray of light couldn't have passed between them. Craig loved holding her close and he was tempted to hold her by her ass but he reminded himself that it was Blake's wife. Sandy rubbed her leg into Craig's crotch and he could not help but get an erection. Craig knew she could feel it against her thigh and she drove him crazy as she pressed into him. During the fifth song she slipped her hand between them and rubbed Craig's erect cock through his pants.
"Wow did I do this to you?" she teased.
"You know damn well you did," Craig whispered in her ear.
"I'm glad that I was able to turn you on," she whispered back.
They finished the dance and then returned to their table. Blake was smiling and sipping his drink when they sat back down. Sandy smiled and nodded at her husband as if giving him permission to do something. Then he shocked Craig with an offer.
"Craig, Sandy and I are not up for the nude Jacuzzi this evening and we would like you to share our bed with us tonight," Blake bluntly offered.
"I don't know what to say," Craig replied somewhat stunned as he had not expected that.
"Say yes, I love to be with two men," Sandy coaxed Craig.
"I have to tell you that I am not interested in another man's cock, if that is what is on your mind," Craig stated firmly looking at Blake, remembering him with the two dark haired guys.
"That is not a problem, but have you ever let a guy suck you or have you ever fucked a guy?" Blake questioned.
"No, I have not," Craig stated firmly
"Craig, just go with the flow and if you are uncomfortable with anything we'll understand," Sandy added.
"Let's go back to the room then," Blake invited him.
Craig followed Blake and Sandy to their room when once inside Blake and Sandy undressed and hung up their clothes. Craig stared at the two look alikes and he was still amazed how much they resembled one another. Except for Blake having a cock and Sandy having a pussy they were almost identical. They both had slim curvy bodies that were virtually hairless and they both had smooth unblemished skin. Sandy had very small tits and she was almost flat chested. They both had blonde pubic hair that looked more like peach fuzz.
At that moment Craig felt a little foolish standing there fully clothed. So he took his clothes off and folded them neatly in the nearby chair. Then it was Sandy and Blake who stared at Craig and they admired his body and complimented him on his fitness. Then they approached Craig and they both ran their hands over his body. They enjoyed feeling his muscular torso and they ran their hands over his washboard abs. Craig was hard in an instant and then Sandy cooed.
"Oh Blake, look at his lovely cock. It is beautiful," Sandy gasped as she took a hold of Craig's 8" erection.
Sandy told Craig to get in bed and lay on his back. Then she knelt between Craig's legs and took his cock in her mouth. Sandy sucked Craig's cock and caressed his achy balls. Sandy was a very accomplished cock sucker and she was able to take Craig deep in her mouth. Craig was convinced that he could feel his cock at the back of her throat. Sandy seemed to have the ability to massage Craig's cock head with her throat muscles and she soon had Craig racing toward an orgasm. Craig held her head with his fingers entwined in her blonde hair as he began to face fuck her.
Craig looked over at Blake and saw that his cock was an average size of about six inches. Blake knelt behind Sandy and slipped his cock into her. Sandy never stopped working on Craig's cock while her husband fucked her. Sandy reached under Craig's scrotum and lightly touched his perineum which sent Craig over the edge. Craig blasted loads of cum in her mouth. Sandy rapidly swallowed all of his cum and continued to suck and milk his cock dry and drain Craig totally.
Craig lay back on the bed as he recovered slowly from the fantastic blow job and watched Blake fuck Sandy until Blake's body stiffened and he announced that he was cumming. Sandy leaned back against Blake as he came in her pussy which caused her small tits and hard nipples to stand out. She definitely had cute tits even though they were small. Her nipples stood out like little dicks they were so hard.
Craig was already starting to get hard again when Sandy asked if Craig would like to fuck her. Craig's cock was now rock hard and he moved it toward her. Sandy lifted her legs and presented her pussy to Craig and he pushed his cock against her labia allowing it to slide into her warm passage. Sandy gasped as Craig's cock nestled into her vaginal passage.
Blake moved up to Sandy's head and stuck his dick in his wife's mouth. Craig fucked Sandy slowly at first and then he picked up the pace. Sandy used her vaginal muscles to tighten her pussy and she massaged Craig's cock by clenching and unclenching them. Craig felt his second orgasm travel from his balls up through his dick as he shot wads of cum deep into Sandy's pussy. Craig leaned over her body and grabbed her small firm tits and let the rock hard nipples slip between his fingers as Sandy continued to use her vaginal muscles to milk Craig's cock dry of every drop of cum.
"Oh Blake, I'm going to cum," Sandy suddenly cried out.
Blake pulled his cock from his wife's mouth and slid down Sandy's body to her pussy just as Craig's softening cock slipped from Sandy's pussy with an audible pop. A trail of semen trickled out of her just before Blake got there to suck Craig's seed out of his wife's pussy. Blake covered his wife's pussy with his mouth just in time to catch all her love juice. Sandy's body thrashed around as she orgasmed and came in her husband's mouth. Sandy lifted her hips off the bed as Blake sucked every drop of the combined juices from his wife's pussy. Sandy had been fantastic as Craig had just received a world class blow job and fucked her very hot pussy. The three of them remained silent and rested for several few minutes and then Sandy said she wanted two cocks in her at the same time.
Sandy worked on Craig's cock until it was erect again and then she mounted him lowering her pussy onto Craig's shaft. Sandy cooed as Blake worked his fingers in and out of her asshole lubricating it for his cock. Then he lined up his cock and slipped it right in Sandy's hot ass. That answered Craig's earlier thought about whether she took it in the ass or not. Sandy sighed as the hard cock entered her ass and Blake fucked her slowly. Craig could feel Blake's smaller erect cock through her membrane and it surprisingly turned him on. Blake didn't last long and he soon came in his wife's ass.
"Your turn," Sandy whispered to me.
Obviously Sandy wanted Craig in her ass so she lifted off of him and then she got back on all fours. Blake handed Craig the lotion and he put an ample amount on his cock. Craig added his own saliva to his lotion coated cock making it as slippery as possible. Craig eased his cock into Sandy's ass and she tensed up when she felt Craig's larger cock at the entrance. Craig was excited to be fucking his very first ass. Craig held Sandy's hips and slowly pushed his cock in her rectum.
"Oh easy, go easy, let me get used to you. Not too deep at first, please," Sandy begged.
Craig was inexperienced in anal sex but he didn't want to hurt Sandy so he slowly fucked her ass with about half of his cock in her. Sandy loosened up gradually and as she did more of Craig's cock slipped into her bottom. Soon with patience and steady strokes Craig was fully imbedded in her ass. Sandy grunted as Craig picked up the pace and drove his cock home with each stroke. Craig looked at her beautiful ass as he fucked her and he couldn't believe that he was really fucking her cute ass. Craig excitedly watched his cock slide in and out of Sandy's tight bung hole and he felt his orgasm building in his balls. Craig shoved his cock in as far as he could and unleashed a torrent of cum into Sandy's rectum. Sandy was surprised by the force of Craig's ejaculation and the amount of semen that he shot into her ass since it was his third time that night. Craig kept fucking her slowly and Sandy's sphincter muscle contracted around his cock involuntarily milking every drop of cum from him. Craig wanted to stay in Sandy's beautiful ass forever but he felt his cock soften in her rectum. Craig's cock slipped out slowly and made an audible popping sound when it cleared Sandy's anus. Craig had just experienced one incredible ass fuck. It was his first but at that moment he knew it would not be his last.
Sandy was in need of an orgasm and she reached between her legs to finger her own pussy. Craig rolled her over and told her to let him take care of that for her. Craig knelt between her legs and lowered his face to her pussy. Sandy had a quick orgasm and humped her pussy up into Craig's face. Sandy coated Craig's face with her pussy juice as she thrashed about on the bed. Craig was hard again so he moved up and slipped his cock back into Sandy's pussy and fucked her through multiple orgasms but he didn't cum again. Sandy finally begged Craig to stop fucking her as she couldn't cum anymore. When Craig rolled off of Sandy he looked over at Blake.
Good job Craig, she needed that," Blake said.
"Bring that delicious cock over to me Craig," Blake requested.
"I've got nothing left Blake, Sandy drained me of every drop," I replied.
"That's okay I just want to nibble, you don't have to cum again," Blake told Craig.
Blake sucked on Craig's cock and although Craig was at least semi-hard he knew that he wouldn't cum again for quite awhile. Blake kept sucking Craig's cock and Craig realized that even though it was a guy, Blake was every bit as good as his wife at sucking cock. Blake got Craig hard again and then asked Craig to fuck him. Craig watched as Blake got on all fours and lubricated his asshole. Craig didn't know if he could go through with it at first but when he looked at Blake's shapely ass it looked just like Sandy's. Other than his ball sac hanging down he looked just like Sandy waiting to get fucked. Craig lubed his cock again and then eased his cock into Blake's ass and fucked him with long deep steady strokes. Sandy got in front of her husband and took his cock into her mouth. Craig fucked Blake until Blake came in his wife's mouth but Craig could not cum again and he pulled out after Blake ejaculated in Sandy's mouth.
It was time to get some sleep so Sandy and Blake invited Craig to stay with them that night. They all stayed naked in the bed and pulled the covers over their tired bodies. Craig had no trouble falling asleep with Sandy in the middle between her husband and him. Sometime in the very early hours Craig was awakened by the bed moving. When his head cleared he realized that Blake was fucking his wife. Somehow Blake had gotten in the middle and he had his back to Craig as he fucked Sandy from behind. Craig didn't know if Blake was in Sandy's ass or pussy but Craig was overcome with desire and he decided to get in on the action. Craig's cock was hard so he moved it to Blake's ass and touched Blake's anus with the head of his cock. Blake reached back and guided Craig's cock into his ass and then he resumed fucking his wife. Craig didn't have to move much since Blake's fucking motion caused his ass to slide back and forth on Craig's cock.