Southern Nights

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Rob wasn't too sure about what was going to happen, but he wasn't going to complain. Both Danica and Kelli strapped on the dildo's. Kelli took hers and plunged it deep into Danica's dripping pussy. She then pulled out and positioned herself right in front of Robert's face. "Okay, lets see if you enjoy the taste of this," she said as she placed the tip of the large rubber cock on Rob's lips.

Rob licked the rubber cock and loved the taste of Danica's pussy juice. As he started to work the dildo into his mouth and down his throat, he had to fight his gag reflexes. But this was starting to feel good. He liked the feeling of something long and hard inside of his mouth.

While Kelli was working her rubber appendage into Rob's mouth, Danica reached for the tube of lube and started working on Rob's ass. He seemed to be much more acceptable to her fingers lubricating and working their way into his ass this time. Once she had her fingers in his ass, she pulled them out, lubed up the rubber dildo she had strapped on, and placed the tip of it on the edge of Rob's hole and applied gentle pressure. The cock slipped in really easy this time. Rob was learning to relax and appeared to enjoy the feeling. After only a couple of minutes, Danica was buried all the way into Rob's ass. She then started to pump and little harder and a little faster. She pulled her cock out to the tip and then trust it all the way back in.

Rob was moaning and enjoying this. The feeling of a cock buried in all the way into his ass and the other rubber cock buried in his mouth and down his throat. Now that he had learned to control his gag reflex, this was really feeling hot. His cock was even harder then it was before and he never thought that that was possible.

After about 10 minutes of this, Kelli pulled her dildo out of Rob's mouth and laid down in the 69 position under Rob. Rob immediately went back to work on the rubber cock in front of his face. Kelli then wrapped her hot mouth around Rob's swollen member and sucked him right to the hilt. With Kelli sucking hard and Danica pounding his ass every bit as hard as he did hers earlier, it was no time at all before he could feel his loading building at the base of his cock getting ready to blow out. He squeezed his butt checks together and then his load was blasting into Kelli's mouth and down her throat. Danica pulled out of his ass and Rob collapsed on his side beside the girls on their bed. As he laid there catching his breath, he could see Kelli and Danica kissing and swapping his cum back and forth. This was the last thing he remembered before passing out with a smile on his face.

He was woken up early the next morning, as the girls were getting ready to go for the plane. He was tired and sticky all over from the sex session the night before. He rose from the bed exchanged lingering good bye kisses from the girls and made his way over to his cabin. He collapsed onto his bed and was unconscious again.

Around noon Robert came out of his coma to the smell of something sweet. When he opened his eye, he saw the statuesque figure of Cheryl standing in his doorway smiling.

"Hey, you are still alive?" she crooned. "I would have been really disappointed if you weren't. Here," she continued, "Your friends left me this to give to you."

As she reached out Rob took an envelope from her beautiful hands. Inside was a brief note thanking Rob for making their last night there such a memorable one and left their email addresses and phone numbers. "Just incase he happened to be heading down-under sometime soon."

"Thanks. I appreciate that." Rob said. "I guess they are long gone by now."

"Yeah, we had a good talk before they left, but they have been gone now for almost 3 hours. You just died in here."

"Well, the travel time and all that action on the first night seems to take a bit out of a person," replied Rob with a grin on his face. "I am starved, would you like to join me for lunch?"

I would be delighted," Cheryl replied with a beaming smile.

As they walked back towards the main resort, Rob found that it was very easy to talk to Cheryl. They spent the rest of the day, touring the local area and going through some of the local villages. After dinner back at the resort, Rob and Cheryl went for a walk along the beach and watched a bright red ball of fire set into the surf. Without even knowing when, Rob found that he was holding Cheryl's hand. It felt good there.

After walking around the villas and other areas within the resort Rob suddenly realized that he was back at the court yard where the hot tub was located outside of their cabins.

"Well, that is beginning to look like a good idea." said Rob nodding his head towards the steaming tub.

"It sure is. My muscles are a little tight from all the walking today," replied this gorgeous beauty beside him.

"Okay, I'll meet you back here in a couple of minutes." Rob was well aware that most of the people walked around naked here, but he still preferred to have his suit with him.

Once he had his trunks on, Rob was back out in the hot tub waiting for Cheryl. It wasn't too much longer before she was out there with a really hot bikini on that accentuated her lovely long legs, hips and perfect ass. As well as her perfectly shaped and sized tits. This suit left very little to the imagination. As she slipped her stealth form into the tub, Rob couldn't help but notice he was getting a little stiff.

Cheryl moved up beside Rob and he wrapped his arm around her shoulders. She leaned in and kissed him hard. Her tongue snaked out and caught his in his mouth.

Rob was instantly hard. Nothing could turn him on faster than a deep French kiss. The thought of someone's tongue invading his mouth and then sucking on his tongue always gave him a raging hard-on.

Another couple walked past the hot tub but didn't show any interest in coming in. Rob and Cheryl were alone and he was enjoying it. He felt her pull away a bit as she reached her hands around to the back of her bikini top. In a quick, well-practiced motion, she pulled both the top and bottom strings so that the small patch of clothing holding those magnificent breasts in, fell away and the succulent tits sprang to life on the surface of the bubbling water. Instinctively, Rob's hand went out for one of those glorious orbs and held it while he lowered his mouth to the nipple. Her nipples and areolas were dark brown and large. He couldn't wait to taste this treasure, so he lowered his head and popped the nipple into his eager mouth. He started to suckle on the breast and interrupted that with running his tongue over that huge chocolate areola. These had to be the best tits that he had ever sucked on. He could hear Cheryl moaning and felt her move her hand under that water to his raging cock.

Cheryl had had other lovers before, but none of them could do to her what Rob was doing with her breasts. She had never felt herself get so excited. While enjoying this fantastic feeling she was getting from him, she slipped her hand under his waste band, and started to rub Rob's raging cock with her hand. She started at the tip, then grabbed a hold of his shaft and ran her hand all the way down his full length until her hand was resting against his balls. She had to have that lovely cock in her mouth. So she pulled back from Rob, kneeled in front of him in the pool. Grabbed a hold of the waste band of his trunks, and pulled.

Rob floated for half a second and noticed that when his ass touched down again, he had nothing on. "Dam! This girl knows what she is doing!" he thought. She then dove under the water and Rob felt her work her way up his legs until her mouth was wrapped around his cock. This was the second time that Rob had received an under-water blow job and the sensation was fantastic. After about a minute of this Cheryl came back up for air.

"I can only hold my breath for so long. Why don't you pop those sweet cheeks of yours up onto the deck and I can give you the blow job you deserve." She gasped, trying to catch her breath.

"I've got no problem complying with that," stated Robert as he practically jumped out of the tub and sat himself down at the edge.

Cheryl pushed him back into a lying position again and immediately went back to work sucking his terrific cock. This was one of the sweetest ones she had ever had in her mouth and she was going to make sure that he really enjoyed it.

Rob enjoyed a good blowjob, but had never had one that made him cum or even brought him to the edge of orgasm. Cheryl was about to do that. She was amazing with her lips. This was by far the best blowjob that he had ever had. Cheryl seemed to know exactly when to slow her attack on his cock so that he wouldn't blow his load. The one thing that Rob was missing now, thanks to the girls last night, was the ass play. They had turned him on to anal and he liked the feeling. As Cheryl stopped for a quick breather, Rob asker her "Do you have any toys we can use? I really enjoyed what the girls did to me last night and I want to try that again."

"I was hoping you'd say that." replied Cheryl with a playful look on her face. " I think I have just the thing for you." and taking his hand, she led him back to her cabin.

Once inside Cheryl knew exactly what she was going to do. She led Rob over to the bed and sat him down on the edge. "Here, put this on," she said handing him a blindfold. "You are going to have to trust me on this one."

Rob took the blindfold and put it on. He had never done this before, but this whole trip seemed to be one sexual discovery after another. Cheryl then helped him lay down on the bed. Rob could feel her moving around on the bed, but could not even see a shadow of her and what she was doing.

"So, you want to play with toys. Do you?" she teased.

Rob just nodded, not knowing what to expect. He felt her place her hands on the inside of both of his legs, and gently pushed them apart. He then felt the bed move indicating that she was now between his legs. He heard the top pop off of a bottle and felt the cool lubricant rubbed against his ass. Cheryl then inserted one of her well-lubed fingers. While she was working on Rob's ass, she took his cock in her mouth and started to suck on it again. Rob was in heaven. In no time at all, he felt two then three fingers comfortably in his ass.

"Okay, here comes your treat, big boy," Cheryl crooned.

Rob could hear the lube being rubbed onto something. He felt Cheryl move back between his legs then he felt the tip of something being pressed against his asshole. There was a little resistance, but he let his hole relax and then he felt the tip slip in. This was much bigger than the ones the girls had used on him the night before. It's circumference filled his ass and he could feel it rubbing against his prostate. Then she started to push it in deeper and deeper. He thought for sure that he couldn't take any more but still she pushed it, ever so gently until he felt the base hit against his butt cheeks. Then he felt her pull out and work her way back in again. She kept repeating this motion until she was pulling almost all the way out and slamming all the way back in. Rob wasn't too sure how big this toy was. But it felt like it was at least twice as big as anything the girls had used on him last night. He was completely full, and the feeling of this monster rubbing against his prostate inside was driving him wild with lust. He had to see what Cheryl was using on him.

"I need to take off my blindfold, I need to see you," pleaded Rob as Cheryl continued to plow his ass.

"Are you enjoying this?"

"Oh God yes."

"Better than last nights toys?'

"Much, much better. I can't believe the feeling. It is driving me crazy."

"Then I guess you are ready to see this," whispered Cheryl in a husky voice, and told Rob to take the blindfold off of his face.

It took a couple of seconds for Rob's eye's to adjust, and focus. He smiled up at Cheryl's face above him and then he looked down.

Nothing in the world would have prepared him for what he saw next. Cheryl's hands were on the bed beside him, holding her up. She wasn't holding anything in them. The "toy" that she was using on him was her own cock. She was a shemale. This thing that was filling his ass was her own cock. And it was her balls that were slapping against his butt cheeks.

Once the shock had cleared from his head, Rob realized that his cock was harder than it had ever been. And it was glistening with pre-cum. A smile crossed his face. Here was a woman whom he was quickly falling for, and she was as big, if not bigger in the crotch then he was. Well, he always figured the woman who got him to settle down would have to have a lot of balls. He just didn't realize that they were going to be full of cum and jetting up his ass.

Cheryl's smile turned to a look of concern. "Are you okay with this? Do you want me to stop"

"God no. Keep going. This feels so hot. " gasped Rob barely able to breath. After a few more minutes of having his ass pounded, Rob's curiosity got the better of him. He needed to check something else out.

"Lets switch, I want to fuck you now," requested Rob.

Cheryl pulled out and moved back from Rob. He could see that Cheryl was wearing a condom. Extra caution when being with someone you've just met was a great idea. Rob was glad to see that she had thought to use one.

Quickly Cheryl passed Rob a condom and the lube and then laid down on the bed where Rob had just been. Rob quickly rolled the rubber onto his long stiff cock and squeezed out a big dollop of lube into his hands. He used this to rub all over Cheryl's ass and onto his condom covered cock. He then proceeded to work his fingers into her ass the same way that she had done earlier. When he was up to three fingers, he pulled back his hand, grabbed a hold of his cock, and placed the tip against her asshole. He applied the same slow pressure she had until the tip of his cock poked through the sphincter and into her ass. With slow strokes he pushed a little deeper and then pulled out; deeper and pulled out. He kept going until he felt his hips hit against her hips and felt his balls slap her ass. Then he started with slow strokes pulling almost all the way out, and then burying himself deep in her ass again. He hooked her legs over his shoulders and pulled her ass up higher so he could go in even deeper. When he looked down, the site almost made him lose his load. The site of his cock slapping into her tight ass and her cock and balls in front of them jumping around with each trust was an awesome site to see.

Her moans were encouraging him to keep on going and he started to pickup his pace. Eventually, he was like a jackhammer going at her ass. Watching her large cock and big balls bounce around out of control. Her moans were turning into screams of pleasure. He could feel that he was about to blow his full load.

"God. Stop." She screamed. "I wannt to take your full load down my throat"

So Rob, stopped and pulled out his swollen cock. He ripped the condom off and positioned himself above her on the bed in a 69 position. Her hot lips were wrapped around his cock in no time. Rob had sucked on a dildo last night, but this real thing in front of him was looking a lot tastier. He took the tip of her cock in to his mouth and then sucked down on it. Her pre-cum tasted sweeter then he thought it would. He felt this lovely muscle hit the back of his throat and he remembered what he did the night with the toys. So he opened his throat up a little more and started to swallow. Her cock was now passed the back of his mouth and down his throat. This was so much better than rubber.

Cheryl had Rob's cock down her throat as well. Her nose was buried in his balls. She was working her mouth and tongue up and down his full length, while he did the same thing to her. She had never been with a guy that could suck a cock like that. And nobody had ever taken her full 10 inched, either in their pussy, ass or mouth. Rob was able to take it in both his orifices. She could feel the juices building up in her balls and getting ready to jettison out of her cock. She pulled her face off of Rob's cock long enough to say, "Oh god, I'm going to cum."

"So am I." replied Rob as he felt the first of his semen starting to blast out of his cock. He then buried his face back onto Cheryl's wonderful dick and continued to suck. The first shot hit when Rob had Cheryl's cock down his throat and he could feel the blast go straight down. She continued to orgasm and blast after blast came out of the tip of her cock. After the second blast though, Rob's own orgasm started and he filled Cheryl's mouth and continued to shoot. He could feel her throat contracting and swallowing his cum the same way he was doing with hers. After about 5 minutes of orgasms, the couple rolled apart and laid very still listening to each other catch their breaths. Rob could not believe his luck, this was heaven, and he was right in the middle of it.

Rob awoke with a start. The sun was just breaking over the horizon. Cheryl was lying cuddled up in his arms. He must have fell asleep after the torrid sex session the night before. He could get use to this. It sure felt right, and after their conversations from the previous day, Rob had found out that Cheryl lived in a part of Toronto not too far from him. He had simply told her that he was going to Montreal after here. He was only going there for a couple of day's business and then he was returning home as well. He wanted to surprise her when he was back home. When she started to stir, he looked over at her and seeing her smile, he leaned in to kiss her. This was perfect and he knew that this was what he had always been looking for. His first hesitations about this trip were now long gone. Life was good.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
PeggedonePeggedonealmost 14 years ago
Very hot

Great story, it made me soooo hot reading it.

Share this Story

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
The Happiest of Endings A massage with a big, hard surprise.in Transgender & Crossdressers
More Stories