Fantasy Island

Then again, maybe Robert wanted to keep something like this to himself?

My mind was racing and my cock was straining against the cage as I found it impossible to focus, settle my head, or have a moment's peace without a random thought disrupting my day.

Ann had came home Sunday afternoon. It was a bout 2pm. She had been at her assistant's apartment since 8pm Friday night.

Friday night, she gave him a blowjob in the kitchen of the apartment, with the shades open. She had "teased" him all week by wearing low cut tops, higher skirts, garter belts, and they had instituted a "no panties Friday" office policy (Ann's suggestion with Joe's help).

Joe had convinced her to shave her pussy completely bald, and to wear revealing clothing to work. It had its charms. Her red hair and knockout body did not hurt either.

After getting his load off, the assistant did not feel like eating Ann's pussy, no matter what she did. She got upset about it and was just about ready to leave when his room mate came home. The room mate was a carbon copy of Ann's assistant and (as far as Ann could tell) would / could / should measure up in all ways.

Ann saw Greg and calmed down right away. She decided to spend the night as they had planned, and the three of them started drinking. She got her assistant drunk, and then he passed out. Greg and Ann helped him to bed, and then went back into the living room.

The room mate was very charming and very horny. He had broken up with his girlfriend of six months a few weeks ago and just never felt like doing anything. He confessed that being around Ann made him feel alive.

Ann wore a white top that buttoned down the front with no bra. She wore a red skirt, no panties, and black heels. She showed up ready to fuck, but "someone" had been beating off all week (Ann assumed), so once he blew his load in Ann's mouth, he was done.

Ann was pissed about it, but now she was all better. She cranked up the heat by unbuttoning the top two buttons. "Do you feel any more alive when I do this?" Ann asked Greg.

Greg was no slouch. He took the hint and kissed Ann on the lips. "Yes" he answered after the kiss. Ann smiled and then shoved her tongue in Greg's mouth and he pulled her in closer. Ann could feel his hard cock against her thigh. It made her even wetter.

The two of them made out for a few seconds and then rushed into Greg's room. The two got completely naked and jumped into Greg's bed. They started making out and exploring each others' bodies. Ann grabbed his cock and started stroking it. Greg took his time exploring Ann's body. He made her feel like a queen.

Greg was "first" to make a move, and he slipped down between Ann's legs, found her freshly shaved pussy and plunged into her. His tongue sent shockwaves through her body. She held Greg's head in place and lifted her hips to grind against his face. She came instantly, filling his mouth with her sweet nectar. Greg swallowed all that he could, and continued eating her pussy.

Another orgasm ripped through Ann's body, making her moan deeply and pull Greg's head into her pussy even deeper.

Just as Greg was about to stop, Ann chanted, "Don't Stop... something big is happening... OH GOD... I'm coming."

Greg needed no other encouragement. He pushed his own face into Ann's married pussy, parting her shaved lips even more, and tongued her clit harder than he had ever tongued any other woman in his life.

In about 30 seconds, Ann let out a howl and shot a stream of pussy juice all over Greg's head. She had NEVER squirted before Greg, and now that it had happened, she was loud and unforgiving.

As soon as it passed, she pulled Greg in for another "treatment" and within a few seconds, Ann was screaming out "OH GREG!!!!! Greg.. Greg... Greg..."

As she screamed out his name, she shot fluid into the air, and all over Greg's silk sheets.

Greg lowered his head back down and licked off the extra juices.

Ann's body tingled all over. She was in a place no other man had EVER put her, and she wanted more. She was panting and weak from her body being out of control.

"If he can do this with just the tongue, what can his dick do?" she asked herself.

She pulled Greg up from between her legs and kissed him passionately, mouth open and tongues rubbing. She could taste herself all over Greg's face. She loved it. She loved everything about this moment and this man.

She could no wait to see where things were going.

Greg steadied himself with one arm and guided his cock head against Ann's pussy. She was so wet that Greg slipped inside of her with a little effort.

"Oh my GOD." Ann blurted out loud.

Greg looked down at her, "You okay?" he asked, worried.

Ann pulled him down for more kissing, "Everything is wonderful."

Greg moved in and out of Ann slowly. Her poor "neglected" pussy had not been treated the way it should have been in the past, leaving her wanting more most nights. Joe had done a miserable job of satisfying her, and now she had a green light to be treated "this way" and there as no turning back.

Ann watched as Greg was careful to move slowly. Ann cooed with the way he was treating her, moan with each movement and eagerly awaited the moment when he would flood her pussy. She wanted this so bad. Everything was perfect.

Greg started moving in and out of Ann, moving faster and taking longer strokes.

"Its happening again." Ann announced to Greg.

A few more strokes of his cock, and Ann was gushing all over the bed again. She sprayed more this time around that before.

Greg quickly slipped his cock inside of Ann and raised her hips off of the mattress. Her shoulders were the only thing touching the mattress. Her titties rolled against her cheeks as Greg angled her hips just right. The head of his cock, rubbed the inside of her clit, massaging it in just the right way.

Ann blurted out, "I'M CUMMING AGAIN."

Greg went into action. He wrapped his arms around Ann's legs and pinned them against his torso. He used the strength of this shoulders and back to hold her hips off of the mattress, and to fuck her properly.

His cock slipped in and out of Ann and it made a sloppy sound. As Ann was screaming loudly, Greg continued to pound her pussy. As she squirted out more fluid, her pussy contracted around Greg's cock, squeezing him with each inward thrust. This made Greg want to shoot his load.

"Oh SHIT Baby... I'm gonna explode!!!" Greg yelled.

Ann reached for Greg's muscular ass and pulled his hips and thighs to her.

"Cum inside of me. I want to feel you explode." Ann grunted.

Greg worked his lower body faster than before and within a few seconds, Greg grunted really loudly as his cock filled Ann's married pussy, he exploded inside of her, granting her wish.

Ann could feel his balls against her ass. She could feel them move with each twitch of his cock, and each spurt of cum Greg shot into her.

The sensation was beyond belief for Ann. She moaned with deep satisfaction as she was filled with a stranger's cum. A "stranger" that earned the title "Best She ever Had".

Greg let go of Ann's legs, and he lowered her hips onto the silk sheets. He kept his cock buried inside of her, and she wanted him to stay inside of her. She wrapped her long legs around him and they kissed and grunted for several minutes until Greg's cock started to go soft.

Greg rolled off of Ann and Ann raced to the bathroom where she hovered over the toilet and several drops of semen dripped from her pussy. Her knees shook. Her body tingled. This was just the beginning of her experience with Greg.

She wiped away what she could and returned to the bedroom. Greg was laying on the bed, his cock still erect, but softer than it was before. There was a wet spot in the middle of the bed bigger than Ann's hips.

She should have been embarrassed.

"Every man before Greg has been successfully shamed tonight." she thought to herself.

"You okay?" Ann asked innocently.

Greg lifted his head, "Never better."

Ann was relieved. She crawled back into bed with Greg and cuddled him. She fell asleep in the wet spot, on Greg's chest, and she slept until noon.

The next morning Ann woke up alone. Greg had drawn a rose on a sticky note and left it on the pillow. He wrote his cell number under the rose.

Greg had to work a delivery route to help pay off the furniture his girlfriend bought and then she left him after two payments. He has a month or two left, and three months left on the lease. Then he was moving out.

Greg had just found out that his former girlfriend had cheated on him WITH his current room mate (Brian), but he could not find a place to live and afford to pay off the furniture, so he was "stuck". Brian did not know that Greg knew, which kept things peaceful (for now).

When Greg saw Ann, he decided to get revenge. He was tired of Brian bragging about how he was going to have an older woman over and how she wanted to spend the night with him. "blah blah blah" Greg thought to himself.

Greg never anticipated what happened last night would be some of the best sex of his life.

Ann knew that her assistant would be hung over and pretty much a shit for the day. She also knew that once he found out what happened last night he would turn into a little bitch, and eventually ask for a transfer. Right now, Ann was okay with that. Greg had given her something she NEVER had before, and Ann was ready to hang onto that for a while. "I'm gonna wrap my pussy around that and ride it out." she joked to herself.

Ann wanted to stay in bed and relax. She couldn't.

She heard movement outside and assumed that Brian was leaving for the day. She heard the door shut, and lock. She snuck a glimpse out the window blind and saw her assistant leaving with a back pack.

"Granola Boy will be gone all day." she joked to herself.

She decided to wait it out a few minutes and then tidy up a bit. Then (she promised herself) she would leave.

Ann got up and started snooping so she could find something to wear. She found a dresser drawer with some of Greg's T-shirts in it. She slipped one on over her naked body. "Aren't I just the roommate darling." she thought to herself. It was long enough to just cover her ass, if she did not bend over.

Ann got up and stripped the bed, then threw the sheets in the washer. She fluffed her skirt and top, then hung them up in Greg's bathroom.

She straightened up the kitchen, started the dishwasher, and wiped off the counters. She bagged up two bags of trash, and set them by the door.

The sheets finished and Ann threw them in the dryer. They wouldn't take long, so Ann rushed to finish up before either of them got back.

She slipped back into Greg's room and picked up a few things, found a laundry basket and filled it.

Her phone's text chime went off.

Joe - "Everything okay?"

Ann - "YES. I am fine. Best sex of my life last night, wicked story. Will tell all when I get home. If not home by 2, will call."

Ann finished that text and the phone went off again.

New Number (Greg) - "Hey sleepy head. Almost done at work, you want some lunch?"

Ann - "Hey Sexy. That sounds good, but I'm not really "dressed" for lunch."

Greg - "Will bring you something to help keep your strength up. What do you like?"

Ann - "Craving a burger."

Greg - "I know a place. Be there in 30 minutes.

Ann - "How long does Brian stay gone for on the weekends?"

Greg - "He left for his Sister's place, won't be home until late Sunday."

Ann - "That's a game changer."

Ann - Sent a pic of herself in Greg's shirt, standing on front of the bathroom mirror.

Greg - "I cannot drive with a hard-on."

Ann - "Take your time, get you and that cock here safely. Getting into the shower."

The sheets finished and Ann whipped them out of the dryer. She slipped them back on the bed, made the bed, and she jumped into the shower. She finished and wrapped herself in a towel. She walked out into the bedroom to find her new favorite shirt. She slipped it back on and walked out into the kitchen. She LOVED the feel of the air against her pussy lips, especially when Greg was the only one that would get to see how she looked in his shirt.

The door clicked and Greg walked in with two bags.

The two sat down and ate some of the best burgers Ann had ever tried. The fries were made of the same quality. She needed something to eat and this was the best food she had eaten in a while.

"So, I know you are older than Brian and I. What is the story with the two of you?" Greg asked.

Ann looked at Greg. "Brian is my assistant at work. I have been teasing him all week. I was supposed to come here and spend the weekend, but he must have decided that his sister's place is more interesting."

"I don't know how." Greg shot back.

Ann looked at Greg. "I am married."

Greg had a hurt look on his face.

Ann held up her finger to pause his reaction, then she continued, "I am telling you this because I want you to know two things. One, my husband WANTS me to have sex with other men. As long as I go home and tell him everything that happens, he is okay with this arrangement. Its called Cuckolding."

The look on Greg's face changed from hurt to confusion. "He wants you to have sex with other men, then TELL him about it?"

"I know. I do not get it either. Something about the humiliation, and belittling him that makes it better for him." I have read. "Its a clinical documented sexual disorder." Ann finished.

Greg was silent.

Ann got worried. "Do you want to know what number two is?"

Greg paused for a second. He thought to himself, "Fuck it, I am in this deep."

Greg looked at Ann and swallowed really hard. Ten different remarks came to mind, but Greg decided to let Ann define this moment for both of them. "Yes, I would like to know what the second thing is."

Ann took a drink and looked at Greg, right into his eyes. "I don't want to do this anymore. I HATE IT. I hate the idea of having random men view me as nothing more than a piece of ass. I want LOVE. I want a meaningful physical relationship with one man."

Ann paused, her voice was cracking. She took a second and then pressed on. She cleared her throat, "In addition to all of that bullshit, I don't want to go home."

"You are a married woman and I -" Greg started.

A tear welled up in Ann's eye.

"WAIT." Greg gathered his thoughts for a second. "What did you say?"

Ann looked at Greg. "I don't want to live the life my husband wants for me. I want ONE man, a man that makes me happy. A man that leaves me notes, takes care of me, makes me feel like I am the center of HIS universe. I want to feel like I did last night, with you."

Greg's mood instantly changed, for the better.

Ann looked at Greg. She needed him to say something back to confirm her feelings. Greg could not form a sentence right now because he was in shock. He held up his finger and acted like he had a French fry stuck in his throat.

He bought enough time and when he raised his head to look Ann in the eyes, she saw that his eyes had welled up a bit.

"After my girlfriend dumped me, I wasn't interested in finding another relationship. That lasted for a while. I hated it. Then I saw you last night, and all of that changed." Greg replied.

Ann started to cry.

Greg was soft and gentle when he reached across the table and wiped away her tears.

"Brian is gone for the night." Greg started. "You want to make a fort and watch old movies?"

Ann looked at Greg. It was the goofiest thing she had ever been asked in her adult life, and the first response from her lips was, "Hell YES."

The two covered the windows, stacked up couch cushions, and ordered pizza - they both loved supreme pizza with everything.

They watched old black and white movies, ate pizza and then Ann decided it was time to go to bed. She shut the movie off and kissed Greg.

"I washed the sheets today." she whispered.

Greg kissed her back and they went to bed.

The next morning, Ann and Greg thought it would be "best" if she was not there when Brian got back.

Ann got up and fixed Greg breakfast, then she got changed into her own clothes and she left, leaving Greg the promise that she was done with anything her husband wanted.

Ann got home and told Joe that she had a wonderful time with her lover and that she was going to spend next weekend with him.

Joe started to protest.

Ann looked at him as only a fire-eye red headed woman can and reminded him, "This is what you wanted. Me fucking some hot stud on the other side of town, REMEMBER?"

Joe nodded.

"Its my birthday." Joe added.

Ann looked at Joe and said, "Well then you can sleep well knowing I got you EXACTLY what you wanted."

Then Ann leaned in and whispered in Joe's ear, "I squirted this weekend. It was amazing. He made me squirt 4 different times. Just know that each and every time you see me with a cold drink, ALL I am going to be thinking about is replenishing my fluids so I can squirt harder than the last time."

Joe's dick got hard just with the words Ann told him. She reached down between Joe's legs and found his hard dick. With her head still by his ear, Ann grabbed his dick and then told Joe, "His cock is much bigger than your dickie, and it stays hard. He knows how to eat pussy too."

Joe's dick twitched as Ann spoke. "Oh.. and he loves the fact that I am shaved. He said to tell you thank you."

Ann let go of Joe's dick and walked off to take a shower and put on something less than flattering. She could have walked around naked, but Joe did NOT deserve that. He deserved to be tormented, and left to wonder what Ann's new lover looked like. He deserved to sit around with an aching hardon and have images of Ann's wet pussy being filled with a healthy cock.

Ann took a shower, shaved her legs and got dressed in a pair of baggy shorts and a loose fitting shirt. She wore a bra and made sure Joe knew that she had no interest in him tonight.

Ann slept very soundly that night. Greg sent her a heart via text message.

Monday morning, Brian came in 10 minutes late. His shirt had a stain on it, and his pants were wrinkled. He acted as if nothing happened.

He stopped by Ann's office and asked how her throat was.

Without looking up, Ann replied, "My throat is a little sore, but not as sore as my pussy. After you passed out on me I had to go find some cock. Glad I did too, because it was some of the most fantastic work I have ever had done on me. I need you to give the Brass Report today. My throat is sore from having some of the best orgasms of my life with my new lover. Too bad you ran out to your sister's this weekend. You REALLY missed out."

Brian had a worried look on his face. "Well, its not my sister's. I just tell my room mate that. I am seeing his old girlfriend. Not too long ago, he had to work late and she came over early. We ended up in bed together and she broke it off with him later that night. I just tell Greg its my sister's place so he wont be suspicious. I think he is still in love with her."

Ann was floored. "So you were going to cheat on her, with me?"

"Well, yea, she is alright, but you are a cougar." Brian admitted.

Ann laughed at herself. "So you are not too serious about this girl?"

"No, not really. She just likes the idea of banging someone right now. I think she is seeing a few other guys too. We don't go anywhere, I just go over, get a hotel close by and she comes over and we fuck. She told me that she will fuck me every Saturday and every Wednesday if I make sure she gets the furniture Greg is paying on. Poor sap. She is stringing him along until he has the furniture paid off, then I am going to kick him out and she will come over and take the furniture." Brian admitted.

"That is simply devious." Ann chuckled. "I like her. You should make sure we meet some time. Maybe a threesome in the future?" Ann suggested.