Virgin to Debauchery

Her eyes welled up with tears and she felt her anal channel being stretched to new dimensions He continued to ease his cock in and out of her asshole feeding her an additional ¼ to ½ inch at a time, each time waiting until she relaxed. It seemed to take hours before his entire tool was lodged deep in her ass. Caleb shot his load immediately when his cock was fully embedded in Ashley's ass. Caleb stayed hard however as he always did as he knew that he could cum two, three and even four times without removing his cock from a woman's asshole. Ashley felt the warm cum shoot into her rectum and it actually felt strangely good. She liked the soothing feel it gave her ravaged asshole but she felt unbelievably full. Caleb started to fuck her with long deliberate strokes as he admired her beautiful ass accepting his huge cock. Caleb stroked her marvelous ass cheeks and told her how good she looked in this position with his dick skewering her luscious ass.

The pain had subsided completely and now Ashley felt more of a bloating and cramping sensation. The cramping then stopped and Ashley only felt somewhat constipated with the cock in her ass. Caleb felt his next orgasm start down in his balls and rush up through his cock flooding Ashley's rectum again. He came more than he expected and cum soon filled her asshole to overflowing and backed up coating his cock and running down the inside of her thighs. However Caleb was not done with Ashley and he continued fucking her tight ass. Her rectum held his cock tightly and Caleb felt as if he could stay hard forever in Ashley's beautiful ass.

He kept slowly fucking her ass until his cock started to soften. Ashley' ass involuntarily was milking his cock draining it of all his seed. When Caleb's cock slipped from her asshole with an audible pop, his cum shot out and ran down the back of her legs and over her pussy. It looked like Ashley was shooting cum out of her ass. She collapsed face down on the bed and Caleb stroked her buns lovingly as she lay quietly.

Ashley thought to herself, "Not in my wildest dreams would I have ever thought that someone would fuck me in the ass and that I would enjoy it."

She continued thinking that at first she didn't like it but tried to hang in there. Then the pain either subsided or she became numb. She had never felt so full and it was a feeling of giving complete control to someone else. Ashley thought that being fucked in the ass was the ultimate in submission and she felt totally dominated. Ashley's pussy was on fire and she rolled over on her back in hopes that someone would service her needs. Both Abraham and Jonah fucked her again and then they left her to recover from her first night of debauchery.

"That is enough for tonight. We will see you again tomorrow Ashley," Abraham told her.

The three men left the room and Ashley remained in bed dazed and confused about what happened to her. Did Joseph know that this was going to happen? What was his night like with Claire and Sarah?

For the remainder of the honeymoon, Ashley was fucked continuously by Abraham, Caleb and Jonah. At times she had two cocks in her and other times three. Her first triple penetration blew her mind. She was riding Abraham as she sucked Jonah with Caleb in her ass. It was wild. By the end of the week she was accustomed to handling three cocks at once and her holes had taken each cock. She had even adjusted to take Jonah anally. It was the last night of the honeymoon when she was reunited with her husband and he ejaculated in all her holes and she had multiple orgasms. Joseph had been well schooled by Claire and Sarah in vaginal, oral and anal sex.

Ashley and Joseph returned home with the others and they began their lives together. The following months proved to be just as sexually active as the honeymoon. Ashley was often visited during the day by Abraham, Caleb and Jonah and sometimes all three. Sarah and Claire continued to have fun with Joseph. Ashley learned that Sarah and Claire had gone through similar ordeals on their honeymoon. It was Abraham who suggested that Ashley and Joseph take a real honeymoon and he arranged for them to go to Rome. He dispatched the corporate jet and booked them into a five star hotel suite.

COFFEE AND

The next morning after her sexual journey with Tomaso, Ashley rolled out of bed and went into the bathroom. After a quick shower she dressed and left Joseph sleeping in the bed. She decided to go to the hotel espresso bar and pick up some coffee and pastries. She put on her mini skirt, cotton sweater, panties and flats. She opted not to wear her bra since she was not leaving the building. Ashley took the elevator to the lobby and headed toward the espresso bar.

"Buon giorno signora, good morning!" a voice called out to her.

Ashley turned at looked in the direction of the voice. "It is me, Roberto, the bartender."

"Oh Roberto, I didn't recognize you. How are you?"

"Bene, good, where are your going signora?"

"To the espresso bar to get some coffee and pastries; Joseph is still sleeping."

"Ah yes, too much to drink last night."

"Maybe but he had help from you and Tomaso."

"Si, si, that Tomaso he is a clever one. Come with me signora I wish to show you something."

Roberto took her arm and led her to the lounge which was closed that time of day. He unlocked the door and ushered Ashley inside. Once inside he locked the door and guided her to a table.

"I have been going crazy over your beautiful legs and curvy bottom. Tomaso told me what a good lover you are and I have to have you too."

Ashley couldn't believe her ears or that she allowed herself to be alone with this man. Roberto fished his hardening cock out of his pants and she noticed that he was well endowed and uncut like Tomaso. Before she could react to his exposure, he dropped to his knees and ran his hands up her gorgeous legs. Ashley gasped aloud as she often did and Roberto took that as a sound of encouragement. He hooked his fingers in the waistband of her panties and pulled them down to her ankles.

He pushed her back so that she was on the table and ducked his head between her legs. The panties were still around her ankles when he dipped his head in and began to eat her pussy. Ashley threw her head back and thought, "Here I go again." Roberto pushed a thick finger in her pussy and like Tomaso he quickly found her g-spot. It didn't take Ashley long to cum and she flooded Roberto's mouth with her love juice. He drank down every drop of her sweet nectar and then he moved out from under her legs.

Roberto helped Ashley off the table and turned her around. Bending her over the table he entered her from behind. She still had her panties around her ankles and he never lowered his pants or underwear. Roberto wanted to be able to re-dress quickly should someone come looking for him. He fucked Ashley from behind caressing her lovely buttocks the entire time. Just before he came he pulled out and ejaculated on her bottom. Ashley felt the warm semen cover her buttocks and trickle down in the crack. Roberto pulled out of her and wiped his cock on her ass.

"Get me a napkin," Ashley whispered.

Roberto quickly located a napkin and handed it to her. Ashley wiped the semen from her body and then pulled her panties back up. She turned around and faced Roberto who had already put his cock back in his pants. "I need to get going," she told him.

"Of course signora, will we see you this evening?"

"I don't know, maybe."

Roberto unlocked the lounge door and Ashley left. He stayed behind and relocked the door. Ashley made her way to the espresso bar and got coffee and pastries. She returned to the hotel room and Joseph was sitting on the side of the bed. He smiled at her and he was grateful for the coffee.

"Sorry about last night, those drinks snuck up on me."

Ashley nodded and reminded him of their plans that day. She downed a pastry and sipped her coffee and they discussed the options. They decided to visit the Coliseum before lunch and then do some people watching on the Spanish Steps. After that they would play it by ear. Ashley thought it would be fun just walking around the neighborhoods as well. She suggested dinning out casually for dinner in one of the local neighborhood restaurants.

As it turned out they had a lovely day together. They enjoyed dining with the locals and when they returned to the hotel they went straight to their room. They were not interested in visiting the lounge that evening. Once in their room they were anxious to get to bed and enjoy each other. Once again they followed their favorite ritual beginning with oral sex in a 69 position. Next it was missionary sex followed by anal sex with Ashley on all fours. Afterward they both slept soundly and in the morning Joseph was at her with his morning piss hard-on.

COMPANY FOR DINNER

The next morning Joseph and Ashley ran into Tomaso at a sidewalk café near the hotel. He joined them for an espresso and suggested that they have dinner that evening with him and his wife. Ashley was surprised that Tomaso was married but even more surprised that he would invite his wife to meet the woman he fucked two days ago. Joseph agreed and offered to pick them up with the limo they had reserved for the week. Ashley and Joseph used the limo that day to visit the Seven Hills of Rome.

That evening Joseph and Ashley took the limo to pick up Tomaso and Isabella. They were to dine at one of Rome's renowned restaurants. When Isabella got into the limo Ashley was immediately taken with her. Isabella had to be at least 10 years younger than her husband and she resembled a young Sophia Loren. Isabella had dark brown almost black hair, her eyes were brown and mysterious and she possessed that Mediterranean dark intriguing look. Her figure showed off a generous bust, narrow waist that flowed into her shapely hips and killer ass.

Isabella took note of the visual assessments by Ashley and Joseph. The limo dropped them at the restaurant and they dined for several hours. During the dinner the conversation was mostly about Joseph and Ashley and Rome. However the two couples were aware of the sexually charged atmosphere surrounding them and Tomaso asked Joseph if he would like to swing with them. Joseph immediately agreed as he was taken with Isabella. Following dinner the two couples returned to the hotel and Ashley and Joseph invited Tomaso and Isabella for a night cap in their room. The four of them entered the hotel suite and Joseph poured cognacs for everyone.

"Let the men enjoy their cognacs while you and I entertain them and each other," Isabella told Ashley as she took her hands in hers.

Ashley was no stranger to female love making as Sarah and Claire had taught her well. Isabella led Ashley to the center of the room where she embraced her and kissed her. Ashley kissed her back reveling in her beauty. Isabella began to undress Ashley. She unbuttoned Ashley's blouse and removed it. Isabella was pleased to see that Ashley did not wear a bra and she gently massaged the American girl's tits. Isabella rolled Ashley's nipples in between her fingers and then dipped her head down to take them one at a time in her mouth and roll them in her teeth. Ashley sighed with pleasure and secretly wished the beautiful Italian woman would move faster.

Isabella's mouth left Ashley's tits and then kissed her once again plunging her tongue deep into Ashley's throat taking her breath away. As she kissed her Isabella continued to caress Ashley's tits with her hands. Isabella trailed her kisses down Ashley's face and throat back to her breasts. Isabella lingered at Ashley's breasts momentarily and then descended across her abs to her waist. Isabella unhooked Ashley's skirt and slowly lowered it to the floor. Isabella lifted Ashley's legs one at a time clear of her skirt and then ran her hands up her legs to the waistband of Ashley's skimpy panty.

Isabelle caressed Ashley's shapely buttocks before she pulled her panty down her legs. Isabella teasingly slowly lowered Ashley's panty down her legs and then removed it as she had her skirt. Ashley was trembling with desire but Isabella made her wait as she took her time with the American. Isabella then rolled Ashley's thigh nylons down and off her legs. Ashley was dripping with desire and her pussy was oozing her excitement. Isabella took one swipe of Ashley's pussy with her tongue and then stood up.

"Now you may undress me," Isabella said as if giving Ashley permission.

With her hands shaking due to her uncontrollable lust, Ashley began to undress Isabella. Isabella was wearing a black cocktail dress and it fell to the floor as Ashley unhooked and unzipped it. Isabella stood there in her bra, panty and nylons and she was a specimen of beauty. Ashley unfastened Isabella's bra and her breasts burst forward. Ashley took her beautiful tits in her hands and massaged them emitting a pleasure moan from Isabella. Ashley salivated over Isabella's big luscious tits with their dark engorged nipples. She sucked on Isabella's nipples as she molded the large firm globes in her hands. Ashley fell in love with Isabella's tits.

Isabella reminded Ashley that there was more and Ashley next removed the beautiful young woman's nylons. They were thigh highs with elastic tops just as Ashley had worn. Ashley remained on her knees after removing Isabella's nylons and stared directly at her panty covered pussy. Ashley then grabbed the panty at the waistband and slowly unveiled Isabella's treasure. Isabella has a patch of black pubic hair above her delectable looking pussy. It was obvious that she kept it trim otherwise Ashley would have been staring at a black forest.

Ashley grasped Isabella's firm fleshy ass and pulled her toward her face. Ashley then buried her face in Isabella's bush and licked frantically at her pussy. Isabella moaned with pleasure but then she reached down and pulled Ashley to her feet.

"Let's pleasure each other," Isabella said as she led Ashley to the large bed.

Both beautiful women lay down on their sides in a 69 position and began to eat each other's delicious pussy. They tongued each other and sought out each other's clit. Ashley was pleased that Isabella had a large clit and it was like sucking a tiny dick. Isabella went wild when Ashley sucked and nibbled on her clit and she strove to return the favor to Ashley. The two women brought themselves off rather quickly but continued to eat each other as the juices flowed into their mouths. Ashley and Isabella felt the presence of other bodies on the bed as Tomaso got behind Ashley and Joseph got behind Isabella.

"Go ahead Joseph, she loves it in the ass," Tomaso told Joseph.

"As does Ashley," Joseph replied.

Both men eased their lubricated cocks into the respective assholes of the two women. Isabella obviously handled Joseph's intrusion easier then Ashley did Tomaso's. For Ashley this was like losing her anal virginity all over again, God he was big, Ashley thought to herself. Tomaso was considerate and allowed Ashley time to adjust to his size before he started to fuck her ass hard. Soon both men were fucking the women's asses frantically as their hips slapped against their buttocks and pushed their bodies into each other. Ashley and Isabella eat each other's pussy with a fury as the dicks in their asses raced toward their orgasms.

Joseph fired a huge amount of cum in Isabella's asshole as did Tomaso in Ashley's. The two women upon feeling the warm liquid fill their rectums came in each other's mouth coating each other's face with an abundance of female nectar. In a somewhat bizarre act Joseph slipped his cock from Isabella's ass and fed it to Ashley who instinctively took it in her mouth. Tomaso did the same with Isabella and the foursome made quite an erotic picture with the women sucking cocks through each other's legs.

Isabella got up and retrieved a double headed dildo from her purse. It was easily 18" long and 6" around about the same size as her husbands cock. The dildo had two realistic looking cocks at either end with a large set of fake balls in the middle. Isabella turned Ashley toward her and inserted one end of the cock in her pussy and the other end in her own pussy. The two women began to slowly fuck each other with the large fake phallus as they rubbed each other's tits. The fake cock filled both women's pussies snugly and stayed in constant contact with their clits. They fucked each other this way until they both orgasmed again, shaking and holding tight to each other as tremors moved their bodies.

The two women were rolled over on their sides by Tomaso and Joseph so that they were facing them. Tomaso took the double headed dildo and inserted an end in his wife's ass and the other end in Ashley's ass. The two women gasped as the length of the dildo filled their assholes. Tomaso slid his rock hard cock into Ashley's pussy and Joseph followed suit by fucking Isabella's pussy. The two men pounded the women's pussies and by doing drove the double dildo deeper into their anal channels. The four of them were moaning and groaning in ecstasy and the men rapidly approached another orgasm and the women were not far behind.

Tomaso exploded into Ashley's hot pussy just before Joseph filled Isabella's twat with his spunk. Ashley and Isabella were out of control as their hips slammed into their male partners and their asses smashed against one another. Tomaso and Joseph pulled their deflated cocks out of the two women and watched them as they sub-consciously continued to fuck their asses on the fake double cock. Soon the two beauties slowed down as their intense orgasms subsided and they lay there back to back seemingly coupled by the fake cock in their assholes.

The rest of the night and way into the early morning hours they experimented with more copulations and positions. Ashley was triple fucked with Isabella underneath her and the dildo in her pussy, Tomaso in her ass and Joseph in her mouth. Then the scene was repeated with Isabella having the dildo in her pussy, Joseph in her ass and her husband in her mouth. The last thing Ashley remembered was Tomaso fucking her pussy while Joseph was in her ass and she was eating Isabella's pussy.

CIAO BELLA

The day after the marathon of sex with Tomaso and Isabella, Ashley and Joseph slept in. They ordered room service for a light breakfast and then decided what to do on their last day of sight seeing. They spent most to the day at St. Peter's square and then they dined locally again. That last night they spent alone and enjoyed their normal sexual ritual. They would be heading back to the states in the morning.

The next morning they were up early to shower, pack and have a light breakfast. The limo would take them to the airport. Ashley was in the lobby waiting for her husband to check-out. There were a number of people ahead of him and the process was slow. Ashley sat in one of the upholstered lobby chairs as she waited. Her miniskirt rose up to her mid thigh and her lovely legs were on display.

Ashley saw Roberto and another man she recognized but did not know by name. They spotted her and approached her. "Buon giorno signora, are you waiting for someone?" Roberto asked.

"Yes, my husband is checking out. We are leaving today."

"Oh so soon, we cannot have you leave without taking something with you, something to remember your visit to Rome. Come with me signora."

Ashley looked over at her husband and saw that he was still waiting so she went with Roberto. The other man followed along. "This is Pietro," Roberto told her.

Roberto took her into the lounge again and locked the door. Ashley wondered he had planned to give her as a souvenir. Once in the lounge Roberto moved behind Ashley, raised her miniskirt and yanked her panties down to her ankles. Now she knew what he planned to give her to remember him by. Holding onto her hips, he droved his cock into her quickly taking her breath away. Ashley grasped a nearby table to balance herself. Then Pietro moved in front of her and offered his cock for her to suck.