Poolboy's Bi-sexual Clients Ch. 04

"Try one, I'll get it for you," Cindy replied.

She got up and walked across the pool deck into the house and Curt watched her ass the entire way. Her ass was just unbelievable and Curt felt his cock twitch with the thought of fucking her again.

"She has some ass doesn't she?" Ricky said watching Curt's reaction.

"It is beautiful and so desirable," Curt agreed.

Cindy had introduced him to anal sex and he was now addicted to it. He felt that there was nothing more beautiful the shape of a curvy female ass. The thought of watching his cock slide in and out of a beautiful shapely ass was his biggest thrill. Cindy's ass was the most alluring that he ever fucked but he had loved the anal sex with Nichole, Sophia, Janine, Many and Monica at the party.

Cindy returned with the Bloody Mary and set in down next to Curt. She smiled when she saw his erection and teased, "Did I do that to you?" she said sexily as she patted his woody.

"He was watching your ass, that's what did it," Ricky laughed.

"My ass has always got me into trouble. It started in high school when I was 18 years old. I went to this private school and we wore school uniforms. The pleated skirts were cut 10" above our knees so our thighs were always on display. When we walked up the stairs, teachers could look right up out skirts and see our cotton panty covered asses," Cindy told Curt.

"Wow, I bet the boys were walking around with erections all the time," Curt responded, his cock twitching in his lap.

"Yeah but so were the male teachers. It was a teacher who took my anal virginity. The guy was a pure ass lover and like nothing more that sticking his dick in a cute round ass. Thankfully he was good looking and had an average size cock," Cindy continued.

"Did it happen in school?" Curt inquired excitedly.

"Oh yeah, I was bent over his desk with my skirt thrown up on my back. My panties were pulled down to the top of my knee high white socks. He did things to me with his tongue that made my ass tingle and I was receptive to the anal sex. It hurt at first even though he lubed me up but then I liked it. He ejaculated in my ass and I orgasmed. I was surprised that I could cum from being butt fucked but then I was hooked. I loved the feel of cum shooting into my ass," Cindy detailed.

"Did you do it a lot in high school?" Curt asked even more excitedly this time.

"Oh yeah, I became one of his regulars and then after I let one boy fuck my ass, word got around. We had to be careful so I only let 18 year old boys fuck me," Cindy admitted.

"It really got interesting in college," Ricky interjected.

"What happened?" Curt blurted.

"I met Cindy and we dated all through college. One night at a wild party I watched as she got her ass fucked by a bunch of guys. Then one of them took my ass and I found that I liked it. I had always been attracted to cock but had never tried it until that night. I also sucked cock while I was butt fucked and I loved it," Ricky admitted.

"It was wild. Ricky and I spent most of the party on all fours with cocks in her mouth and ass. Once in awhile a guy would eat or fuck my pussy and Ricky would get to fuck a girl. It was our awakening."

"After that night Cindy and I knew that we were meant to be together and enjoy both men and women the rest of our lives," Ricky concluded.

"Wow!" was all Curt could say and then he sipped his drink.

"How is your drink?" Cindy asked.

"It's good. I like it but you could be charged with serving a minor," Curt replied with a laugh.

"That is something isn't it. You can attend an orgy and fuck your brains out as long as you are 18 but you need to be 21 to drink," Ricky added laughing too.

Curt was subconsciously stroking his stiff dick as he listened to Cindy and Ricky. He caught himself, blushed and then released it. He took another sip of his drink and saw that they were both smiling at him.

"You know Curt, you still haven't fucked me. I've sucked your cock but I have never felt that beauty in my ass. I want you to fuck me today," Ricky announced.

"I don't know. I still haven't fucked a guy," Curt replied nervously.

"It's easy. It's just like fucking a girl's ass. I want to feel you shoot in me. I want to feel your first load of the day," Ricky urged.

"Curt I'll help you. It's just the three of us here today. Just try it," Cindy said trying to convince him.

"Okay, I guess so. You two have been so good to me," Curt submitted.

"Great, let's move to the cushions," Cindy told them.

Curt was told to lie on his back and then Cindy sucked his cock to hardness as Ricky lubed his ass in preparation for Curt sizeable cock. Once Cindy had Curt in an aroused state, she straddled Curt and told his to eat her pussy while she continued to suck his cock. Minutes later Cindy sat up and Ricky lowered his cock onto Curt's cock. Curt could not see Ricky because his face was buried in Cindy's pussy. As Ricky lowered his ass onto Curt's cock and then began to bob up and down, Curt felt that he couldn't tell the difference between a guy's asshole or a girl's, at least not when he could see.

Curt was charged up and Cindy's earlier cock sucking and his eating her tasty pussy. He admired Cindy because she always smelled fresh and clean no matter how much sex she had with other people. Curt could feel his release building in his ball sac. He felt his sac tighten and cum run through his shaft and shoot into Ricky's rectum. Ricky's response was to work his sphincter on Curt's cock and milk the shooting rod dry.

"Oh man, I feel it," Ricky cried out.

Ricky stayed on Curt's cock until he felt the teen relax. He eased his body up off of Curt and rolled over on his back to stroke his own cock. Cindy announced that she was cumming and she drenched Curt's face with her sweet nectar. She then rolled off of Curt and sighed as she lay next to him.

"So how was it?" Cindy spoke first.

"Fantastic, it feels like a fire hose was turned on in my rectum," Ricky replied with a chuckle.

"There is no substitute for youth. Speaking of which, you earned your shot at my ass again," Cindy stated seeing that Curt was still hard.

Cindy rolled over on all fours and told Curt to get her ass ready for his cock. Curt scrambled to his feet and with his impressive cock bobbing in front of him; he retrieved the tube of lube. Kneeling behind Cindy he fondled, rimmed and lubed her ass. He loved preparing her marvelous ass and the foreplay had him as hard as he could get. He moved behind her and eased his cock back into his dream ass. Ricky moved around in front of his wife and offered her his cock to suck on. There was so much cum in Ricky's rectum that he felt like he still had a cock in it.

As much as Curt tried to prolong his ejaculation he just couldn't. Every time he was in Cindy's lovely ass he got turned on quickly. He fired another barrage into her anal passage and as always she massed his cock with her sphincter. Curt noticed that Ricky had stopped moving and that his eyes were closed. He knew that Ricky was cumming in his wife's mouth. They three of them remained still as the two cocks were drained and then they separated.

They all jumped in the pool and let their bodies cool off. Afterward they drank some more Bloody Marys and relaxed poolside until they were horny again. The remainder of the afternoon they had casual sex and Curt fucked them both in the ass again. The one time they lay on their sides with Ricky in Cindy's ass and Curt in Ricky's ass. Curt knew when Ricky came in his wife's ass as he felt Ricky's sphincter tighten around his cock. That's when Curt lost and he came in Ricky's ass a second time. Before he left that day he just had to fuck Cindy's ass with her on all fours again. After he ejaculated again he caressed her buttocks for minutes.

"You like my ass don't you?" Cindy whispered.

"There is nothing in this world that I like more that your beautiful ass and there is nothing I would rather do than fuck it," Curt replied with sigh of pleasure.

The three of them were sexually sated so Curt took another swim, dressed and then went home. It had been some weekend and on that he would never forget. He thought about his week ahead and remembered that he was serving Nicki's pool on Tuesday, Nadine's pool on Thursday and the Smit's pool on Friday. It would be another interesting week. What Curt did not know at the time was that he would have a new client who was very special.

CURT'S NEW DISCOVERY

When Curt got home Sunday evening his parents had taken a message for him. It was from a lady who inquired about having her swimming pool serviced. She wanted to meet Curt and discuss it with him. She was hoping they could meet Monday morning. Her name was Pauline Collins and she lived in a different neighborhood than his other clients. Curt called her back and agreed to meet with her at 10:00 AM Monday morning.

The next morning Curt arrived at the Collins residence and he was surprised when a young attractive woman answered the door. He was so taken by her beauty that he just stared at her. She was dressed in a short robe and her gorgeous legs were very evident. Curt assumed she was wearing the robe over her swimwear.

"Is something wrong?" she asked.

"Oh sorry, it's just that you are so beautiful. I didn't expect you to be so pretty and it caught me by surprise," Curt replied getting bolder and feeling more confident.

"Really, that's a nice thing to say. Listen, I just made a fresh pot of coffee. Would you like to come in and have a cup and we discuss the pool," Pauline offered.

"That would be great. I could use a cup of coffee," Curt accepted.

Pauline let Curt in the house and then led him toward the kitchen. Curt walked behind Pauline and admired the shapely legs and curvy ass. The short robe was tight around Pauline's buttocks and Curt could see them undulate beneath the robe. Curt felt his cock stir and he wondered to himself if Ms. Collins took it in the ass. He nearly flipped out when she bent over far enough that he could see that she was not wearing swimwear and the cheeks of her curvy ass peeked out.

Curt became enamored with Pauline as they sat at the kitchen table and chatted over coffee. Pauline knew that Curt was ripe for the taking but Pauline was unsure how Curt would react to a woman with a cock. Pauline refilled the coffee cups for both of them and that's when Curt decided to make his move. Curt made up his mind to hit on Pauline and since Pauline never changed out of the short terry robe, Curt was certain that Pauline would be receptive to his advances. Curt stood up and walked up behind Pauline and put his arms around the pretty young woman.

Pauline tensed up briefly when Curt put his arms around her and held her tightly. Curt nuzzled Pauline's neck and then let his hands slip inside the robe to find Pauline's medium sized firm breasts. Curt fondled the breasts and tweaked the nipples causing Pauline to groan. Curt then opened the belt on the robe and when the robe parted, Pauline's erect 6" erect cock peeked through.

"Jesus Christ, what's going on?" Curt yelled when he saw Pauline's cock.

Curt backed away as he was stunned momentarily. "I'm sorry Curt, I should have told you right away. Please sit down and I'll explain," Pauline spoke.

Curt sat back down in the kitchen chair. Pauline brought over the two cups of coffee and sat down at the table. Then Pauline explained everything to Curt and obtaining Curt's agreement to keep the secret. When Pauline finished explaining the situation Curt was more relaxed and then he felt obligated to tell Pauline about his own bisexuality. Curt explained his relationship with the Smit's to Pauline who was pleased to hear the story.

"Curt if you are still attracted to me I would love for you to fuck me just like you fuck Ricky," Pauline said in the sexiest tone he could muster.

"I would love to fuck you," Curt accepted.

Pauline then led Curt into the bedroom and dropped the robe to the floor. Curt stared at Pauline's naked form and then asked, "What do they call you?"

Pauline smiled and replied "There are lot's of names for people like me. Transsexual or tranny for short, ladyboy is another and of course there are a few not as flattering," Pauline explained.

"I think that I like ladyboy," Curt said.

"Good, now let's get those clothes off of you," Pauline said as she approached Curt.

Pauline undressed Curt ever so slowly and by the time his underwear was peeled down his legs, Curt was rock hard. Pauline stared at the 7+" cock in front of him and then lowered his mouth on the shaft and began to slowly sucked Curt's dick. As Pauline sucked Curt's cock, Pauline wondered how it would feel in his ass. It would be the biggest cock that Pauline ever had in the ass and the prospect of it excited him but frightened him as well. Curt was incredibly turned on and without warning he ejaculated into Pauline's mouth. Pauline was caught off guard by the volume and force of Curt's ejaculation but Pauline recovered quickly and managed to swallow Curt's entire load. It had been awhile since anyone had cum that much in Pauline's mouth.

Pauline stood up and patted Curt gently on his balls. "I know at your age that there is plenty more where that came from," Pauline said as he licked his lips and then added, "Now I want you to fuck me but first we have to grease up that ass buster of yours."

Pauline took out a tube of lubricant and applied it to Curt's cock. Curt stayed hard the entire time as Pauline stroked the impressive young shaft. "I like playing with your cock. I bet I could do this all day but I do want you to fuck me first," Pauline cooed.

Then Pauline got on the bed on all fours and handed the lube to Curt. "Get my ass ready for your big cock," Pauline whispered.

Curt took the lube and squirted a gob right on Pauline's anus and then pushed it in. Curt worked first one finger and then a second In Pauline's asshole. Pauline put his head down on the bed and arched his back further emphasizing the shape of his curvy ass. Curt was still amazed how much Pauline resembled a girl and it served to turn him on even more. Curt caressed Pauline's lovely ass as he lubricated his asshole. Curt then left his fingers drift over Pauline's scrotum and tickled his perineum. Pauline's cock twitched when Curt's finger ran over the perineum and again when Curt caressed the tight ball sac. Satisfied that Pauline's ass was ready, Curt knelt behind him and eased his cock into Pauline's ass.

Pauline placed his hand on Curt thigh as if to guide the penetration. "Nice and slow, let me stretch out for you slowly," Pauline gasped as his ass was spread wider than ever.

"Oh my, you really know you have someone in you when you're there," Pauline gasped.

"God you are really tight," Curt echoed.

Curt took his time slowly feeding his cock into Pauline's ass and then withdrawing it slightly. Each time Curt would go a little deeper and then stop to allow Pauline to adjust. Pauline wondered if Brad would be able to tell the difference once Pauline's ass was stretched by Curt. Then Pauline felt Curt's pubic hairs tickle his buttocks and he knew that Curt was buried to the hilt. Curt began a slow methodical fucking of Pauline's ass and he relished every second he was in the beautiful derriere. Curt reached around Pauline as he leaned over and his hands brushed against Pauline's tits. Curt had momentarily forgotten that Pauline had tits but now he held the tits and caressed them teasing the nipples as well. At that moment Curt truly felt like he was fucking a girl in the ass. It was much easier and more exciting to fuck Pauline than it was to fuck Ricky.

Curt that felt that familiar twinge and he pushed his cock all the way into Pauline's ass and held it there as he fired a barrage of cum into Pauline's rectum. "Oh I feel it, I feel it!" Pauline exclaimed as round after round was released from Curt's cock.

Curt placed his hands on the smooth curvy ass cheeks and caressed them as her filled Pauline's ass with seed. Curt stayed hard and continued to fuck Pauline slowly until Pauline begged him to move to their sides. Keeping his cock deep in Pauline's ass Curt guided them on their sides and then he resumed fucking Pauline. Curt had his left arm wrapped around Pauline's waist and he was holding a tit in his left hand. Pauline asked Curt to jerk him off. Curt's right hand sought out Pauline's stiff 6" cock and jerked him off as he fucked him. "Oh that's it play with my clit," Pauline moaned. Curt liked it that Pauline called his cock a clit.

Pauline came twice before Curt came a third time. Curt felt Pauline's cum shoot through the stuff rod and land on the bed sheets. Curt then placed both hands on Pauline's tits and held them firmly as he drilled Pauline's ass until he came again. The two of them then lay in bed perspiring and breathing hard from their sexual marathon. Pauline checked the time and realized that they had been having sex for almost two hours. Pauline suggested a shower and they showered together.

Curt could not keep his hands off of Pauline's shapely body and he loved washing Pauline's tits and ass. Curt got hard again and he had to fuck Pauline one more time. He slipped his soapy cock into Pauline's ass again and they fucked until Curt ejaculated one more time. Then they finished their shower and got dressed.

"Curt you are hired if you want the job," Pauline offered.

"I'll take it but I can't do it on Tuesday, Thursday or Friday," he told Pauline.

"Wednesday would be best for me. Say around 9:00 AM," Pauline replied.

"Okay should I start this Wednesday?"

"By all means," Pauline said in a sexy voice.

Curt left sexually sated once again and headed home. He was going to be busy as all get out that week. Between cleaning swimming pools and servicing clients it had turned out to be quite a summer. He wondered if he should tell the Smit's about Pauline but decided to hold off on it at least for awhile. Curt then realized that he had crossed the line of bisexuality and he knew then that he could enjoy both women and select bisexual men. Curt knew that he would never suck a cock or take one in his ass but he would enjoy having his cock sucked and fucking cute guys or ladyboys in the ass.

NEXT CHAPTER

The next chapter will also be the final chapter in this series. Curt will make the most of his time at home before he goes off to college. He will enjoy the pleasures of Nadine, Nicki and Pauline and his first bisexual clients Cindy and Ricky.