Making The Best Of A Bad Situation free porn video

One word, "Hey," was all Josh needed to recognize the caller. It was Tim.

"What's up pal?" the friendly voice answered on the other end of the line.

"Ya wanna go for a couple of beers tonight?" Tim asked.

"Hey, buddy, tonight is your big night with Lucy. Isn't tonight when you planned to pop the question? Did you forget today is Friday?"

Tim waited before replying. "Josh, Lucy and I broke up yesterday."

Josh let the news sink in before saying, "What?" Josh blurted out. "You're kidding. You two are a pair, you know, like Dick and Jane. What happened?"

"Basically, Josh, she dumped me."

"Why?"

"I'm not sure. She said all of the right things like, 'It's time for me to move on', and 'We'll always be friends' but I think she's met someone."

"Damn, bad timing!"

"Yeah. I had it all worked out. I bought a half carat diamond and made reservations at the seafood place uptown that we like so much. I hired a couple of musicians to play our favorite song while I proposed on one knee."

"Fuck, that sucks, man."

"Yeah, tell me about it. Josh, I didn't see it comin'. I need to get wasted tonight. Let's have a couple of beers. It's on me."

"Okay, Tim. Look, I have a date with Natalie around eight. How about if I meet you at six? We can have a few beers at Skips Bar and talk. I need to leave by seven thirty."

"Sounds like a plan. I'll be there. See you."

Tim had a head start. He was at Skips at five that afternoon giving him time to down several beers before Josh arrived. Josh joined him a few minutes past six.

"How's it goin' pal?" Josh asked.

The two friends shook hands and Tim said, "I got here a little early, so you need to catch up."

Josh ordered a beer and asked, "Okay, so getting wasted is going to solve your problem?"

With tears pooling up in his eyes, Tim said, "No. It hurts man. It hurts bad like nothing I've ever felt before. I really was blind-sided by this."

Josh took a healthy drink waiting for Tim to continue, but the only thing Tim continued doing was washing down more beer. Finally Josh said, "Ya know, Tim, when a horse throws you, it's best to get back in the saddle as soon as possible."

"You mean get back into the dating scene. I totally get that, man but it's not gonna be easy. Listen, Josh, I'm never gonna find another Lucy. She is the best. God, I love her, I really do."

Josh consoled his friend by saying, "There are other Lucy's out there, Tim, but you have to look around for awhile to find her."

"Maybe you're right but right now I can't do it."

"Well, pal, you're in the right place to start. This place will be swarming with chicks in a couple hours. Look, Tim, you're a good lookin' dude with a great job. What chick wouldn't want to hook up with you?"

It was, of course, a rhetorical question. Tim answered with a weak, "Thanks pal."

The two men talked for the next hour. When Josh left, he cautioned his buddy. "Hey, Tim, be sure to take a cab home. You're in no condition to drive."

Tim hung around the bar watching as the crowd slowly filtered in. Like Josh had said, by eight thirty the chicks started to arrive and by ten, the place was crowded. Of course, Tim was now very relaxed, that is to say, drunk. He wandered around looking for people he knew. Only a month ago, he tended bar at Skips, so he knew most of the customers. 

Ordinarily, Tim would give a girl a friendly hug but he wasn't in the mood for hugs. That was apparent when he greeted girls with a remotely sounding, "Hi" or "Hey."

Finally, Sally came up to him and said, "Hey Tim, what's goin' on? You look a little down."

Sally was a plain looking girl but friendly. She might have been prettier if she styled her hair and wore clothes that were more in fashion. She seemed to be hiding a magnificent body, but it was hard to tell wearing clothes that were popular a decade ago.

"Yeah, it's Sally, right?" Tim answered with a heavy slur.

"Sure. We met last month at Becky's party. You were with someone, but I can't remember her name."

"Sally. It was Sally, We broke up last night." He said it as if someone had plunged a dagger into his heart.

"Wait, Tim, you're a little confused. I'm Sally," she said with a smile.

"Sorry, I've had a few beers. I meant Lucy. Lucy dumped me."

"Ouch! I think I caught you at a bad time."

"No, it's okay. Are you here with someone?"

"No, just the girls. Wanna talk?"

Sally was a great listener. Tim poured his heart out to her. Sally listened and sympathized and reassured him until she offered to drive him home. It felt to Tim that she was mothering him and it was something he needed in his grief.

Tim accepted the offer saying, "Sure, it's better than taking a cab."

On the way to Tim's apartment, Sally said, "Let's get you sobered up. I'm stopping at my place to pour some caffeine in you. Okay?"

"Fine."

At her apartment, she micro waved a cup of industrial strength coffee and loosened his shirt. "Tim," she said, "you look like the Trivago guy on TV."

"Really? Who's the Trivago guy?"

"He's on a commercial for a website."

"So, do you think he's good lookin'?"

"Yep. He's hot. I'm getting wet thinking about him." She loosened the first two buttons on her blouse to emphasize the point.

"Cool," Tim mumbled. "Now that you're at it, ya wanna unbutton a few more?" pointing at her blouse.

Sally just sat in front of him saying, "You better drink that coffee."

She didn't touch her blouse but did something totally unexpected. Instead, she spread her legs just far enough for Tim to see she wore no panties. He now had a bird's eye view of her shaved pussy. Even in his slightly impaired state, he recognized it as an invitation.

Tim slurred, "Mmm, nicely shaved pussy, Sally." He normally wouldn't be so bold, however his intoxicated state had loosened his tongue.

She said nothing but moved closer to Tim giving him a kiss. It wasn't a motherly kiss. "You can do my buttons for me, Trivago man."

Tim was happy to comply. With her blouse open, she unhooked her bra and let it drop to the sofa. Her tits were far more marvelous than he had expected. They were large and firm. She had areoles that were perfectly round with pointed nipples like lush red strawberries. They were erect revealing her arousal. They screamed out to be touched.

She whispered in his ear, "Fuck me, Trivago Man. I wanted you the minute I saw you at the Becky's party. Please, you make me so damn horny."

Tim sat on the sofa stunned. That's when she took his hand inside her skirt and up her thigh. She was not kidding about being horny. He could feel her wetness as soon as he touched her cunt lips.

"Okay," he thought to himself. "Looks like I'm gonna get laid tonight. Maybe Josh was right. Just get back on the horse."

So like Gene Autry, he was back in the saddle again. Only this time, she was the rider and he was the bucking bronco. The beer he had consumed numbed his cock, so he was good to go for a least a half hour. Tim could tell she was enjoying the moment from her occasional orgasms and extreme wetness. She cooed and moaned and whimpered with pleasure.

Finally he succumbed to her rapid pounding and poured a week's worth of his cum into her love tunnel.

Exhausted, she said trying to catch her breath, "Tim, I needed that. You are fantastic. I couldn't believe how long you lasted. You are the best fuck I've ever had," and they both fell asleep.

The thing was, she needed it again. The next morning they did it all over again. So it wasn't until noon that she drove him home back to Skips to pick up his car.

In the afternoon, Josh called to say, "I tried to reach you all morning. I kinda was worried when you didn't answer."

"I just got home, Josh."

"Where the hell were you?"

"I was with Sally. Do you know her?"

"Ya mean that tease, Sally Fischer?"

"I guess so. Fischer is her last name?" Tim asked.

"Yep, if she dresses like her mother."

"That's the girl."

"She didn't let you fuck her, did she?"

"Well, you wouldn't believe it. She thought I was the Trivago guy. She practically attacked me!"

"Unbelievable. I always thought she was hiding something," Josh replied.

"You know, Josh, maybe breaking up with Lucy is going to work out."

"Sounds like it. So, you're back in the game, right pal?

"Looks like it. I was so stupid thinking Lucy was the only one. Thanks for getting me back on track."

"Glad to help. Keep me in the loop," and they hung up.

Tim and Sally Fischer spent most of the next month together, meaning together in bed. She had ordered a book she called her "coffee table book" from Amazon. It was an illustrated guide to Kama Sutra. Unlike most Kama Sutra books, it included color photographs of actual people fucking, not drawings. 

Sally was perpetually horny. She would turn to a page and say, "Tim, let's try this one tonight," and they did.

Some nights they covered two or three pages until they finished the book, then they started on page one and did the book all over again.

One night after more than a week together, Sally said, "I saw the doctor today."

Tim immediately thought, "Uh oh, that could mean only one thing."

"Hey Tim, don't look so terrified. I'm not pregnant. I had the doctor write a prescription for birth control pills so from now on we'll be safe."

"You mean we've been having unprotected sex for nearly two weeks?"

"Yeah but I'm pretty regular and know when I'm safe. Anyway, I like the rhythm method because it's more natural. In an emergency, there is always the morning after pill."

"Hey, Sally, the morning after pill doesn't work once you find yourself pregnant. Give me a break."

"Okay, I didn't know that. Anyway, now I've taken care of it and I'm on the pill. The thing is, I started to worry because when you cum inside me, it's like a volcano erupting. You spurt so much of your hot juices into me that I was sure all that cum would stay inside me until I'm fertile. Don't misunderstand me, Tim, I love the way you fill my vagina with your sperm. Each time you squirt that hot creamy cum in my pussy, I get tingly all over!"

Tim could only imagine the tingly feeling but knew how great it felt when he exploded inside her slippery vagina. "Yeah, Sally, it's really great that you like me to cum bareback. It's so much better that way.

It was during the fourth week after Tim had met Sally at Skips that he became alarmed. Sally began using those three iconic words, 'I love you'. It was clear to Tim that the relationship was getting out of hand and far too serious. One thing was evident in Tim's mind; he was not going to let the Lucy thing happen again. It was time to break it off.

Tim understood the hurt when being dumped, but he had to do it. Sally cried and screamed and wept and begged but Tim's resolve was strong. It was over.

The whole experience with Sally gave Tim added confidence in himself as well as his sexual performance. He decided to try the Internet for one night stands. He chose the new non-monogamous dating site . It was a dating service specializing in people looking for short term relationships. Tim registered with his picture and started browsing. Before long, his inbox was filled with requests.

A woman who called herself Dorothy looked interesting. They exchanged messages on the site. She said everyone knew her as Dot and was thirty-five years old. She was almost ten years older than Tim. Dot was married to Todd and they had two kids. She lived a half hour away by car, and was anxious to meet a younger man like Tim in person and maybe have a one night stand.

They agreed to meet for coffee at Starbucks to see if there were any sparks between them. Wednesday was Dot's husband's bowling night, so that was best for her. She got a sitter for the kids. They met at seven thirty. Tim was nervous when they met even though Dot seemed relaxed. As the two sipped their cappuccinos, Dot said she had been on MateDate for a year, had several "quickies," as she put it and had no regrets. That explained why she was more relaxed than him. She was also a bit more aggressive than Tim liked. Other than that, she had a pretty face and nice body, apart from being middle age and a bit pudgy.

The two exchanged some secrets. Tim told her about Lucy and Sally. Dot was much more expansive, and said she always loved sex since losing her virginity at sixteen in the back seat of a Dodge Caravan. "To this day," she said, "sex in a car is the best sex."

Then she said, "By the way Tim, what kind of car do you drive?"

"A Toyota RAV4."

"That will work," she said with a wink and a smile.

It had gotten dark, and the new friends buckled their seat belts as Tim drove off. But he had no idea where they were going. He only knew what they would be doing once they were there."

"Where to, Dot?"

"Let's try the Forest Preserve near here." She gave Tim the directions suggesting she had been there before. The car was parked in a secluded location under a stand of oak trees far from the entrance. The two quickly slipped into the back seat.

No words were exchanged at first. They were there to exchange body fluids, not make conversation. Dot was quick to unzip Tim's pants going down on him while he removed her blouse and bra. Her breasts were large, pear shaped and nice to fondle. They hung down on her chest like two pouches waiting to be milked. The two sucked on each other for their obligatory foreplay. His fingers found the wet opening between Dot's legs. He was amazed at how tight she was after having two kids. Tim massaged her sensitive love button for only a few seconds when Dot said, "Tim, you're oozing precum on my skirt. Take my skirt off and fuck me."

It was an invitation he could not refuse. He had his pants on the car floor about as quickly as he had her skirt and panties off.

Like Dot had said, it was obvious that she loved sex. She loved his cock inside her, and made sure he was aware of it by saying, "Deeper, Tim, deeper," and "Faster, I want it faster." She was not shy telling Tim what she craved.

First she had her legs in the air as he pounded into her, then she turned over on her hands and knees and took him doggie. They fucked in the cramped back of the RAV4 like teenagers. She had innumerable mini orgasms as Tim continued to thrust into her slippery pussy until he finally exploded deep inside her with a tidal wave of hot creamy cum.

When they had finished, she said, "God, Tim, I didn't think you would ever stop cumming. You can see why I'm on MateDate. Sex with strangers gives me such a rush. It's so much more fun than in bed with my husband, Todd."

Tim agreed, well, with the thing she said about it giving her a rush.

"Now, Tim, clean me up." She pointed down to his cum pouring out of her cunt.

He had never tasted his own cum. This would be a first. He obliged, licking and slurping every last drop from her slit hole. Tim was surprised at the taste of his and her's. He now knew he had been missing something with Lucy and Sally. When he was done, Dot was still as horny as a mare in heat.

She pulled Tim on top of her and said, "Now make me have the big 'O'."

"Give me a minute, Dot. I'm a little spent."

Tim reached into the glove compartment, pulling out a flask of gin that they shared for awhile. Dot was not content just sipping a drink with Tim. She was more interested in his crotch. She spent time sucking on his cock and balls until Tim finally was fully hard and erect. He was ready to fuck again.

They fucked for what seemed an eternity. She moaned and finally cried out, "Keep it in. Don't take it out. Stroke me harder. I'm, I'm, oh, ahhh."

He wouldn't cum inside her newly pleasured twat this time. He had another plan. He was ready soon after her thunderous climax, and shoved his dick straight into her mouth. Now it was her turn to get a taste of his spunk.

Surprisingly, she had made him so horny that he gave her another massive load. Dot did her best to hold it on her tongue but some trickled passed her lips. She embraced his head to gave Tim a deep cum filled kiss. It was the most erotic thing he had ever done.

Tim drove them back to Starbucks. On the way, Dot said she thought he was a stud. She was amazed how he was able to ejaculate with such amazing volumes of cum. Dot said that was one of the advantages of youth. Of course, Tim didn't mention that he hadn't had sex for three weeks. Abstinence has its advantages!

Dot picked up her car, and they both drove to their respective homes around midnight. He never heard from Dot again and that is the way he wanted it.

Tim's first experience on MateDate was so good that he became even more ambitious. Fucking wives was a turn on, so Tim narrowed his search in the MILF category. There was a lot to choose from.

A week later, Tim hooked up with Wendy. She was a very young looking thirty-two with no kids. She had been married only two years. Wendy had written, "I need someone to satisfy my bucket list. My husband is a bit of a prude. We only have sex once a week in the missionary position. I have other desires and want a real lover that can accommodate my fantasies."

Tim agreed to meet her in a seedy motel in the industrial part of town where they rented rooms by the hour. Wendy chose it because it was the least likely place to be caught. She rented the room for three hours and text Tim the room number. It was room seventeen.

Tim knocked twice, then opened the door. Inside was a tall blond woman wearing a naughty looking Teddy. It was Wendy who had no intention of wasting time. It would be no nonsense fucking and she was in charge. Her bucket list included almost every position from the Kama Sutra book and beyond.

When it was over, Wendy thanked him, and said she now knew what it was like to fuck a real man.

Pam was next on Tim's dance card. She was direct and wrote in her profile, "I'm single and I own my own company. I have no time to socialize or have a boyfriend or get married. I'm not looking for romance, only a short term relationship."

Tim was intrigued. She was thirty-eight and got to the point quickly when she wrote, "Thank you, Tim, for replying to my profile here on MateDate. I don't have time to drive the hour to your place. Business is crazy these days. We can have lunch near my store. We'll see where it goes from there. Thursday works for me."

Thursday at twelve thirty, Tim met Pam at the local Subway. She was a pretty redhead wearing a ponytail. He was dazzled by her dimples and perky nose. That was not all he liked about her. Although Pam dressed conservatively, it didn't hide the fact she had voluminous breasts.

Their lunch date was short as was their time together in her nearby apartment.

In a matter of fact way, she showed him into her bedroom, stripped, then they quickly got down to business. Her tits were large and sensitive. He spent only a few minutes massaging them with his tongue before she pushed his head down between her legs. Her pussy quickly responded.

The rest was a pretty ordinary quickie fuck. He penetrated her frontal, sideways, and from the back. Although Tim hadn't cum, she had experienced orgasms twice and finally said in a matter of fact way, "Tim, what are you waiting for? I've got to get back to work."

Tim went deeper, and his thrusts became harder and faster until he exploded. Although his heart was pounding and he was breathing like he'd run a marathon, Pam hardly showed any sign of physical activity. She showed no emotion but only got out of bed, cleaned herself up and got dressed.

Tim was trying to recover when Pam gave him final instructions. "Tim, see yourself out and please lock the door when you leave." And she left.

After his experience with Pam, Tim needed a vacation from MateDate. That didn't keep women from trying to contact him. Eventually, Tim was bored and started browsing the dating site again.

There was a message in his inbox that interested him. It read, "Horny housewife needs sex ASAP. Write me."

Her message was more to the point than from most women so he wrote back, "Interested guy here. Tell me about yourself."

She said her name was Val. She was thirty-eight and had a teenage son. Her husband is an executive on business in New York, and the son spends all of his time with his iPod. She had time to play.

Val wrote something about her desires saying she was especially turned on by anal sex. "Oh yes," she wrote. "I'm horny and black. I've always wanted to try white cock."

Tim was excited at the opportunity to have black pussy, so he sent a simple message, "When and where?"

She wrote back immediately. "Cum to my place tomorrow at two. My son will be with his girlfriend."

Tim checked his calendar and told her that would work for him. She gave him the address.

He had to drive a little over an hour to get to Val's house. His GPS got him there on time without getting lost which was unusual. Tim was geographically challenged.

He drove up to the front door and rang the doorbell. A very pretty black woman wearing a loose fitting robe opened the door.

"Hi," she said "You must be Tim."

"Yes, and you are Val?"

"Yes, come in Tim."

When she closed the door behind them, her robe flew open far enough for him to see she had pierced nipples on two nicely shaped breasts. Val led him to a large living room with sliding glass doors. Through the doors was a patio and a pool.

She came straight to the point. "Tim, leave your clothes here and join me in the pool."

Val dropped her robe and slipped outside to jump into the pool. She really didn't jump but slithered in. Soon she was floating on her back waving to him to join her.

Tim was immediately turned on by her smooth ebony skin and tight ass. He was as hard as a rock when he stepped waist deep into the water.

"Well, Tim," Val said with a broad smile, "it looks like you came ready for action."

He was a little embarrassed by that until she moved next to him taking a firm grip on his fully erect cock.

"Oh how I love the feel of a man's stiff dick. Have you ever had a blowjob underwater, Tim?"

"No, I guess not."

Val took a deep breath and went underwater to take him in her mouth for nearly a half minute before she came up for air to repeat it again. She repeated it at least a dozen times, then gave him a hand job until he began spilling his first load of the afternoon into the pool.

It was a strange sight. After each spasm, a small mushroom-like cloud formed underwater, then floated away. Val kept stroking him until only white droplets no larger than a garden pea drifted off.

She said, "That was fun, Tim but such a waste."

He knew what she meant.

"Look, you'll need some time to recover, so why don't I make us some drinks. Lemonade or gin and tonic?"

Tim said a gin and tonic would be fine with a twist of lime.

They lounged by the pool with their drinks for the next hour soaking up the sun on their naked bodies. It was Val who made the next move.

"Are you ready for another round?" she asked.

"I'm not finished with this one," pointing to his drink.

"I didn't mean your drink, Tim."

"Oh, of course. Sure, what's next."

Val moved to what looked like a child's toy box and pulled out a large balloon-like bulb with a nozzle on the end. She said, "Let's do some anal play."

Val filled the bulb with warm water from the poolside bar and attached the nozzle. Tim watched with intense interest as she lathered it with a generous supply of KY jelly.

"Have you done this before?" she asked.

Not wanting to sound too foolish he said, "Tell me what you want me to do."

"Just stick this end into my ass and slowly press the bulb. When the bulb is empty, go fill it with warm water and do it again. Get it?"

"Fine."

She handed him the appliance and bent over spreading her ass cheeks. Tim for his part inserted the nozzle in her rectum and gently squeezed the bulb. When it was empty, he refilled it as Val had instructed filling her for a second time.

He was amazed that she could hold it inside her for so long. Just as he was about to fill the bulb again, a powerful jet of liquid squirted from her ass like a leak in a garden hose.

"Okay, Tim I'm ready. Use that KY on your dick and take me in the ass."

He greased his hard pole and plowed into her tight anus. Tim was overwhelmed by the feeling of how her ass gripped his cock. Moving slowly at first, he eventually picked up the momentum. She wanted it faster and harder, so he banged at her ass until he could no longer hold back. His second orgasm of the afternoon was as powerful as the first.

When he pulled out, she said, "Not bad for a white guy. I loved the feel of your balls slapping against my ass. You're good, Tim," giving him a toothy smile.

It was around four thirty when Tim began thinking of leaving. Val's intentions were different.

"Tim," she said. "You have to try this enema thing."

"Why is that?"

"If it is done properly, it's like having an orgasm. It is important to hold the water inside you for as long as possible. You start to feel uncomfortable inside but the more pain the more gain. Bend over and don't let it out no matter how bloated you feel."

She filled the bulb and coated the nozzle with jell inserting it in his bun hole. It felt weird and more so when the warm water entered his bowels. He held his anus tight waiting to be filled a second time. The pain began to increase, and he felt that he could no longer hold the fluid inside. Val was back to fill him for a third time. The pain was excruciating. He felt he was going to explode and he did. The water shot out of his ass half way across the patio. As Val said, the release was like a mammoth orgasm.

Val was not through with him. She reached into her 'toy box' to pull out a strap-on. Buckling it on around her hips, she lathered it up with KY and had Tim bend over.

"Now it's my turn to fuck you toy boy," she said.

Quickly she penetrated his asshole with her plastic toy and banged into him. He had never had a foreign object up his ass before although the tingling on his prostrate was rather pleasant making him feel he was about to cum with each stroke.

This lasted for awhile until Val said, "Fuck me. I want your honky cum inside me."

She replaced the strap-on with a butt plug pushing it deep into his ass. Laying on the Chaise Lounge, she spread her legs inviting Tim to enter her. He penetrated her all the way in from the start. They fucked and fucked. She hollered obscenities with each orgasm, He groaned and moaned. She turned and they fucked in doggie style. She was on top, then he was on top again, all of the time with his butt plugged.

The sun was getting low on the horizon before he gave her a healthy load deep inside her Afro cunt. It was a great way to top off the afternoon.

Tim left for home before sunset just as her son drove into the driveway. The timing was perfect.

The boy asked, "Are you one of my mom's DateMate friends?"

Tim was lost for words, then asked, "Does she have many friends from there?"

He said, "I think so. She been giving me the car keys a lot telling me to go see my girlfriend. It works out great for both of us. You understand, right?"

"Yeah, I get it," and Tim drove away wearing a smile.

Over the next two weeks, Tim browsed MateDate. Nothing inspired him until Saturday morning. A thirty-one year old woman wrote that she married a GI four years ago. She had moved from the Czech Republic to live with him in the United States. Her name was Alica, adding that she has loved sex even before losing her virginity.

Tim wrote her a short message that said he would like to get to know her. Alica quickly responded. Tim learned that recently her husband had arranged a gang bang with her taking five cocks in all of the right places. Alica liked the experience but the best part was tasting so much cum. She described herself as a cum slut.

Alica and Tim arranged to meet in an unlikely place. She told him to be at Walmart on Sunday morning at seven thirty sharp and meet her outside the dressing rooms. She worked there and monitored the clothes department.

Tim was anxious to find out what Alica had in mind, so he might have been there a few minutes early. No one was in the store except for the 'associates' so Tim had no problem finding Alica. He was astonished to see a beautiful blond about five feet ten inches tall with a gorgeous body.

Alica gave him a sexy smile and told him with a heavy accent to go into room number three. Seconds later she joined him and locked the door.

Alica began by saying, "Tim, this is a dressing room. Take your pants off." It sounded more like a demand than a suggestion.

She took off her blouse and bra. Tim couldn't believe his luck when he saw two perfectly shaped tits that belonged on the cover of Penthouse magazine. His now exposed cock began to swell, and she had him in her mouth almost immediately.

"Tim, spread your legs. I play with your balls."

He stepped out of his pants and spread his legs wide so she had easy access to his balls. As Alica tenderly stroked them, he leaned back and brought his hips forward. She licked him from his balls to his ass, then just ringed his ass lightly with her tongue. When his cock had stretched to it's eight inch limit, she had him deep in her throat. She let him thrust into her mouth fucking her throat until he could last no longer.

"Cum in my mouth. I taste your cum," she begged.

His first blast hit the roof of her mouth and the second coated her tongue and cheeks. All the time, Alisa sucked asking for more. Finally when he was finished she said, "Yum. That I love very much, Tim."

Alica dressed herself and said, "I go check on the customers. Be back in awhile."

Alica left him sitting on the little triangular seat wondering when she would return. It was ten or fifteen minutes before she was back. She said, "Customers here. We do a quickie."

Again, she took him in her mouth. This time it was only long enough to get him hard. When she could tell he was ready, Alica raised her skirt and sat on his stiff cock riding him for what seemed like a very long time. She had a remarkable ability to anticipate when Tim was about to cum and made sure he was deep in her pussy when he exploded.

This load wasn't quite as prolific as the first one, but it was enough to drip down her legs onto the floor when she stood up.

Before leaving, Alica pulled down her skirt and checked to be sure there were no customers watching them exit the changing room. That was all for Tim's Sunday morning. He watched golf for the rest of the day.

A week later, Tim was so horny he returned to Walmart, again early on Sunday morning. When he got to the dressing rooms, the door to room number three was locked. Tim stood around for a few minutes. When Alica came out, she said, "Tim. It's Tim, yes?"

"Yes, I'm Tim, Alica."

"The older man can't get it up. Would you help me and go in there?"

"With someone in there?"

"Sure, he won't mind."

Tim opened the door and saw a man with white hair sitting where he sat, naked from the waist down.

"No luck, pal?" Tim asked with a tone of sympathy.

"Not yet. Viagra hasn't kicked in yet." the man said.

Alica returned after a few minutes wondering why Tim wasn't ready, that is, why he still had his pants on. He got the message, and she gave him another spectacular blowjob. Once again she give him a happy ending. She was satisfied with the appetizer before diving into the main meal with the older customer. Before leaving, Tim noticed that the older man had responded to the little blue pill and would be able to quench Alica's thirst. He stood around for awhile watching Alica at work before slipping out dressing room number three. She was good at her job.

It was time for Tim to move on and see what else awaited him on MateDate. The next encounter did not happen until he got a personal message asking him to chat.

It was from Charlotte who only said she was middle age. Tim understood middle age to mean from forty to fifty-five. Hey, he reasoned, forty is the new thirty.

He wrote her in the chat room and told her a little about himself. She wrote, saying little, only that she loved his profile and picture. Charlotte also mentioned that she lived in the city on the Gold Coast, was married twice and separated.

Two things clicked with Tim. First, she lived in the city and so did he. That made it convenient. Second, she lived in a Gold Coast high rise and that meant she had money.

"This could work out really well," he decided.

So they went about making arrangements. He was to meet her in her apartment for lunch the following Tuesday at noon. He was to give his car to the valet and tell him to park it in Mrs. Steel's slot.

Traffic was a snarl, so he was late. He called from his cell and apologized. She said she understood. He was finally in Charlotte's apartment at half past twelve.

Answering the door was a petite teenage girl with blue eyes and blond ponytail. She said, "Hi. Are you Tim?"

"Yes, and who are you?"

"I'm Peggy."

"Is Charlotte home?"

"Of course. Come in," the girl said with a nervous smile. "She's in the kitchen."

Charlotte was elegantly dressed and gave him an air kiss from the kitchen. As Charlotte walked toward him, Tim wished he had worn a suit instead of a golf shirt and shorts. She wrapped her arms around the young girl and said, "Let me introduce you to Peggy, my best friend's daughter."

"Yes, we just met," Tim acknowledged.

"Tim," the older woman said, "you are even more handsome than your picture."

"Thanks," but Tim's eyes were riveted on the teenager.

Peggy wore a t-shirt showing her nipples, tight shorts emphasizing her tight ass, and sandals. She said again, "Hi," as if they were meeting for the first time.

It was Peggy's lips that got his attention. They were Angelina Jolie's lips giving Peggy a fuck me face. He tried not to stare.

To say that Tim was surprised to see Peggy in the apartment would be an understatement. He was there to fuck Charlotte and wasn't really sure what Peggy was doing there. A teenager prowling around the apartment was not in the plan.

Charlotte gave Tim a cursory look around the apartment. Then she said, "Tim, I ordered a shrimp plate for lunch. It's on the table, so let's get started. I hope you will like it."

The apartment was bright with contemporary furniture and the dining table was Danish modern. The three of them sat at the table with Charlotte at the head and Peggy and Tim sitting opposite each other. The shrimp plate was served with a delicious dry Italian wine and for dessert Charlotte had ordered a light cheesecake.

They shared a few details about themselves during lunch. Charlotte was a psychologist. Peggy confessed to being bored at school but interested in art. Charlotte explained that her best friend, Tammy, was on, what she called a "Cougar Cruise" and asked that Charlotte look after Peggy while she was on the cruise. Charlotte added that she and Tammy had been best friends since grade school. They were practically sisters.

Tim, on the other hand, tried to be as vague as possible. He told them he was a junior executive in the advertising business.

After they were finished with the pleasantries, Charlotte said, "Tim, I've asked you here under false pretenses."

"How's that?" Tim asked.

"Well, Peggy turned sixteen last month. She was having some problems during her period and her mom asked that I help. So I suggested she start taking birth control pills. It was also kind of a birthday present. The thing is, they seem to be helping her. In addition, Peggy has a boyfriend and you know teenagers."

"I suppose so," Tim answered, "but I wouldn't know without having kids."

"Well, Tim, you might remember what it was like in high school. Anyway, her mother and I don't want her to have a bad experience the first time."

"The first time?" Tim sounded puzzled.

"Yes, I'm talking about her first sexual experience with a boy. Sex is such a terribly important part of life. We want her to enjoy it and not be afraid. We want her first time to be special."

"So where do I come in?"

"We picked you because we thought you were the most sensitive and gentle man on MateDate. And you're young. Your profile showed you to be experienced, thoughtful and kind so Peggy and I chose you."

"Okay, chose me to do what?" Tim was getting the picture, but he wanted there to be no doubt."

"Don't be so obtuse, Tim. Peggy is still a virgin. She wants to have sex with you for her first time. Her mom and I want to make sure it happens in a controlled situation, no drugs, no alcohol, no HIV, no back seat of a car. Do you understand, Tim?"

"Sure, I get it."

"Are you okay with it?"

Tim took a minute before answering. "I think so."

Charlotte said, "Good. We'll head up to the bedroom after we have finished our dessert."

Peggy said nothing during their conversation. Finally, Tim's curiosity got the best of him, and he looked Peggy directly in the eye. "Peggy, do you want this too?"

"Oh yes, Tim. I've been so horny ever since Auntie Charlotte suggested it."

In the upstairs bedroom, Charlotte told him to put his clothes on the chair near the dresser. He felt like he was in the doctor's office, that is, until Peggy began removing her clothes. Peggy was lightly dressed, no bra, no panties. Tim and Peggy stood by the bed very naked and very unsure as to what to do next.

"You are lovely, Peggy," Tim said. "You have an adorable sexy body. Your boyfriend is a very lucky boy."

"Well, he's not exactly a boy. After all, he is eighteen."

"I see. Why don't you lie down on the bed and we'll get started?"

Charlotte stared at the two noticing Peggy's anxiety saying, "It's going to be alright, dear. Just do as he says."

"Auntie, I'm scared! He's too big. It won't fit."

"Of course it will, darling. Tim is thicker than most men and pretty large, but a man is never too big. It just gives a woman more pleasure. Look, do you want me to go first?"

"Yes. Please, I'd like that."

Charlotte was down to her thong when she said, "It looks like Tim is ready too," and she reached over to hold his already hard cock.

For his part, Tim was mesmerized by Peggy's young firm breasts and puffy nipples. He couldn't wait to get inside her tight unspoiled pussy but first things first. Charlotte was first up.

Charlotte stepped out of her thong and led Tim to the bed as if his cock was a leash. Peggy moved away from the bed for a better view.

Charlotte's nude body ignited his horny appetite. Her breasts were larger and more mature than Peggy's but firm. She had a well trimmed pussy with a very alluring expression when she began sucking and licking his erect staff. At the same time, she instructed Peggy by saying that the tip of a man's penis is the most sensitive. Tim felt more like Charlotte's patient than her paramour.

The older woman eventually took Tim all the way down her throat without a sound. She soon came up for air and said, "To get your man hard enough for good sex, you have to use your mouth like this," and she took him all the way down again. She seemed to pride herself in showing off her deep throat abilities.

Charlotte then turned on her back spreading her knees, pulling Tim's head down between her legs. "Peggy, dear," she whispered, "Foreplay is so wonderful. A good man will satisfy you before intercourse, so you get wet inside your vagina."

Peggy reacted curtly. "Auntie, I masturbate a lot, so I already know the feeling."

This was turning into a clinical demonstration. Tim had no choice but to go along with it.

Charlotte was easy to stimulate. It only took a few licks on her clit before she was ready for Tim's engorged cock. Soon the only sounds were of the two adults fucking like rabbits. "Tim," she said, "don't cum. I want Peggy to feel your warm creamy semen inside her."

This was a difficult request, but he did his best to hold back. Charlotte turned out to be a great fuck despite her age. Even if he wasn't there on "false pretenses," this would have been a great afternoon of sex.

After dozens of energetic strokes with noisy intimate sounds and accompanied by a squeaky bed, Tim heard the woman cry out while she thrust her hips in time with Tim's frantic strokes, "Yes, yes, yes. Do it. Fuck me hard."

Tim didn't pull out right away waiting for her waves of pleasure to pass. After she had finally calmed down, Charlotte said to her friend's daughter, "Okay, Peggy, the demonstration is over. It's your turn. Come here with Tim. He is a wonderful lover. We are so lucky to have chosen him. He'll give you pleasures you've never imagined so enjoy the ride."

Tim knew that Charlotte's comments were meant as words of encouragement for Peggy rather than as a compliment to him.

Tim reluctantly pulled out of Charlotte's wet sticky pussy, and she rolled off the bed to make room for Peggy.

For a short time, Peggy sat with him on the edge of the bed. He kissed her with a deep loving kiss. He delicately cupped her firm breasts as if he were holding fine China. Her skin was smooth like porcelain. His lips feasted on her luscious nipples. His fingers played with her pussy. Then gently he moved her hand between his thighs showing her how to stroke his slick cock still coated with cum. 

Peggy had an intuitive sense about giving him a hand job. Call it woman's intuition, but she knew just how to massage him to insure he kept his hard on. Finally, Tim felt that Peggy was relaxed and ready for him to go down on her.

He gently lowered her onto her back with the girl's legs still dangling over the edge of the bed. He knew he had to make sure she was well lubricated or this would be a disaster for both of them. He wondered if she would bleed as he firmly and tenderly spread her legs moving his mouth between the young girl's slim legs.

Tim eagerly went down on Peggy's cleanly shaven pussy revealing a smooth plump mound and tiny rose colored clit. With his tongue flicking her clit, he gradually pressed a finger into her virgin cunt. She jumped at the intrusion like she had been tickled. Tim felt no obstruction and pushed his finger in all the way. Peggy just squirmed. It was then that Tim had doubts about what Peggy was doing with her boyfriend.

Tim then pressed two fingers into that warm slippery hole and felt she was plenty wet enough to penetrate her with his throbbing dick. Charlotte anticipated that Tim was about to mount the teenager, so acting like a coach, she suggested Peggy give Tim a blow job first.

Peggy went to her knees at the edge of the bed with Tim opening his legs while she slowly engulfed his engorged staff past her puffy lips. She did her best but couldn't get him down her throat. She gagged until tears flooded down her cheeks and said, "Auntie, I can't do it like you."

"That's okay, sweetheart. It takes time and practice to be able to deep throat. You'll learn. The more often you give a man head, the easier it is.

"But Charlotte, Tim is already leaking something out of his penis."

"Oh Peggy, that's a wonderful sign. For a man, it's like you getting wet inside. It means you are turning him on and he is ready for intercourse."

It was true. Tim was turned on and ready to fuck her darling house guest. Smelling the pungent smell of her sex, Tim flipped Peggy on her back and spread her legs wide for easy access. The tip of his cock began to penetrate her ever so slowly. When he had penetrated her only an inch or two, Charlotte reached in the bedside table for a camera and snapped a picture.

"You know, Tim, "the first time for a women is so important. She should have something to remember it."

Tim hardly heard what she said as he pushed in further. Peggy squealed, just short of a scream. Tim wasn't sure if it was from hurt or delight. To find out, he pushed all the way in. He had his cock deep into the young girl's tight twat.

"Auntie, it hurts," Peggy cried.

"That's normal dear. Turn over on all fours. Tim will enter you from behind. That might be more comfortable."

So Tim began fucking her tight hole in the doggie position and Peggy got into it. As he banged in and out of her virgin pussy, she moved her hips wildly in sync with his motions. Feeling the intense pleasures of a man's cock pumping inside of her, she was now lost in the moment and had abandoned all inhibitions.

"Oh Auntie Charolette, that feels so much better," she panted.

"I'm so glad, Angel. What makes you happy makes me happy."

Tim could no longer hold back. An amazing spasm overpowered him when he released his first surge of spurts into that youthful kitty. Thinking he might be the first to fill her with his seed had excited him far beyond all expectations. He hemorrhaged shot after shot of his thick creamy cum into her. She must have felt the sensation of his sperm coating her virgin walls as she moaned and moaned, then cried, "Oh, oh, oh. That feels so good, so good."

When his final spasm squeezed out the last drop of semen, Tim just rolled over exhausted and said nothing.

"Tim, that was so great! Can we do it again?" Peggy asked.

Charlotte interjected, "Unlike a woman, Peggy, a man needs some time to recover before he can have another orgasm."

"How much time?" Peggy asked.

"It depends on the man, dear. Tim here is young enough to be ready soon."

"But, Auntie Charlotte, he has gone all soft. Will he be able to do me again?"

"I'm sure of it," Charlotte replied with an air of certainty.

Charlotte ran downstairs to bring them wine from the dinner table while everyone waited for Tim to regain his stamina. They all sipped their drinks for about a half hour waiting for Tim to be ready.

Impatient, Peggy knelt beside him and said, "I want you so inside me. Are you ready? Maybe I can try to deep throat you again and get you hard again. Is that okay Tim?"

"Fine. Just stay there on your knees and give it a try."

Tim sipped his wine as Peggy moved between his legs taking his limp appendage in her mouth. Peggy was a quick learner. Although she still couldn't get him all the way down her throat, she was doing better. He was hard as a rock again, fully ready to fulfill Peggy's desires.

While Peggy was attending to Tim's cock, Charlotte was busy masturbating at the sight of the young girl giving fellatio. Having pleasured herself, she turned to taking 'family' pictures. Charlotte seemed to be gathering material for a case study on adolescent sexual behavior.

Finally, Tim's cock stood at a rigid attention when he said, "Peggy, I'm ready. Sit on my lap. We'll do it here."

It took a few tries to get his thick pole in her tight hole, but once inside her, Peggy's natural instincts and desires took over. She rode his hard cock with wild abandon. Tim loved watching her tits flop and the look of dreamy expectation on her face.

"Peggy, turn around and do what you've been doing again," he said.

She reversed herself and again gave him a joy ride.

"Aren't you going to cum in me again, Tim?" she asked breathlessly.

At that he picked her up in his arms and laid her on the bed slamming into her cunt holding her legs high overhead. Stroke after furious stroke went deep into her love cavern making her wail, "Fuck me, Tim, fuck me. Cum again, Tim. I want to feel your cum."

Tim was amazed at the feeling of her tight cunt as he plunged into her again and again. The bed squeaked and screeched with each stroke until Tim delivered the goods all the way up to her cervix. The erotic squishy sounds of him banging into her and her legs wrapped around his neck had been the final straw. Waves of pleasure filled him as he climaxed for a second time that afternoon. At nearly the same moment, her eyes rolled back and her legs locked Tim like a vice. She cried, "Charlotte, I'm cumming. I'm cumming!"

Tim just laid on tip of the teen angel keeping himself balls deep in her pussy. It was a moment he wished would last forever.

Despite Peggy's objection, he slowly pulled out. She then did something he had never seen a woman do. She tightly closed her legs as if to seal their fluids inside of her. She stayed that way until he had dressed. It was as if she was determined to save his sperm as her first time souvenir.

Tim would have liked to have fucked that teenager for the rest of the afternoon, but Charlotte ended it with, "Thank you, Tim. You were just exactly the right man for the job."

Hearing that, Tim felt like a handy man who was hired to fix the bathroom faucet."

"I'll send you the pictures if you like," she said.

"That would be fine, Charlotte," and he kissed the two ladies goodbye.

Before he left, Peggy gave him a huge hug saying in an giddy adolescent voice, "Thank you, Tim. I can't wait to do it with my boyfriend now."

"Yes, and I'm sure he is looking forward to it too. You'll make the boys really happy, Peggy."

At that, Tim left the apartment.

Tim went home and fell asleep until dark. When he woke up, he said to himself, "Christ, what an incredible and unexpected afternoon."

Tim had to tell his buddy, Josh, about his experience. After enjoying a few beers at Skips the next day and relating his story, Josh said, "I think this Charlotte women should win the 'Auntie Mame Award' for the most compassionate friend." They both laughed until they had tears in their eyes.

Three days later the photographs were in his inbox along with a thank you. Charlotte also wrote that Peggy's mom, Tammy, was thrilled to hear that things worked out so well. Tammy wanted to thank Tim in person, so Charlotte told her how to contact Tim on MateDate.

The pictures were amateur looking porn shots. Fortunately, none showed his face. He smiled to himself as he browsed the dozen or so pictures. The images of Peggy taking him so enthusiastically sent him into another frenzy that required immediate relief. Watching the slide show on his computer and pumping his rigid pole gave him further pleasure as he splashed a mammoth load of cum that ended up sliding down the computer screen.

Although the pictures from Charlotte were expected, another email was not. It was an email from Lucy. He had only heard by the grapevine that she was shacking up with an older man who drove a Ferrari. Obviously, she was looking for another Rockefeller when she dumped him.

The email said, "Hi. Just wanted to see how you're doing. Write me if you have time."

That all seemed so odd to him. It had been nearly a year since he heard from her, so why now? After the pain he had experienced, he wondered if it was wise to send a reply. The truth was, seeing her email in his inbox sent chills up his spine. He had to write her.

"Yep, things are great. How about you?" It was a short and sweet reply.

The next day Lucy wrote, "Okay, could be better. Wanna meet for a drink?"

"Oh my God, what now?" he thought. Just when Tim thought he was over her, she wanted to meet. It brought back all of his feelings for her along with the pain.

A day later on Tuesday, he wrote he was free Friday afternoon. That gave him time to reevaluate the situation and bounce the idea off of Josh. Josh was all for it but cautioned Tim not to rush into things. Tim agreed.

Although he thought a lot about Lucy and what might happen on Friday, he was also curious about Tammy. So, he went back to MateDate to check his messages. Sure enough, Tammy had written. She wrote that she had seen the pictures and Peggy had given her a play by play account of the afternoon. She wanted to tell Tim in person how grateful she was for helping Peggy "come-of-age," as she put it.

Tim responded by telling Tammy that he only had Thursday free and could they meet somewhere in the afternoon. She said that would work for her and suggested the Belmont Motel at two. She would be driving a blue BMW. What Tammy lacked in subtlety, she made up for with honesty.

He wasn't surprised at the arrangement. Tim had sensed that Tammy wanted more than to offer a simple thank you. To put it another way, she was going to thank him in an intimate manner and the Belmont was the place. Tim knew where the Belmont was located. It was well known as the place to go for having an affairs.

Tim parked his RAV4 next to a blue BMW convertible. Tammy made it easy for him to spot her. The top was down and he recognized her immediately. She looked like an older version of Peggy. She fit nicely in the MILF category.

They checked into a room on the second floor. Tammy had brought along a bottle of wine, giving them time to get acquainted.

As they sipped the wine, Tim asked about the cruise. She said it was lovely but didn't go into details other than to say, "Tim, you should have been there. The ladies would have loved to have spent time with you. I certainly would have!"

Tammy said she was a single mom and had gotten pregnant in high school. That cut short her ambition to be a doctor. She had done some acting and modeling, then worked as a stewardess until she landed a job as an executive's personal secretary at the airline.

As she spoke, Tammy sipped her wine while slowly removing her clothes until she wore only heals and a necklace. Her pussy was shaved. It looked to Tim as though she had a boob job.

"So Tim, enough about me. Let me loosen your clothes so I can thank you properly for being so accommodating with Peg. You know, Tim, she has so much more confidence now and thinks of herself as a woman instead of a little girl."

"I can imagine," Tim replied as he stepped out of his boxer shorts. Totally nude, he added, "Peggy is lucky to have such a sexy understanding mother."

It was a quickie and nothing at all like fucking Peggy. She knew her way around the bedroom and immediately had his cock down her throat. Moments after she had given him a short blowjob, he dived into her pussy. He banged into her relentlessly and found Tammy was easy to please. Her orgasms came early and often. She took charge and jumped on top fucking him cowgirl. She frantically drove his cock deep into her, bouncing up and down like on a trampoline. Finally, he flipped her onto her back and pulled her legs over his shoulders. He was deep inside her when the spasms from his throbbing cock began.

It might have been that he imagined fucking Peggy again. Whatever the reason, he shot rope after rope into this horny mother. Like hiccups, it continued one after another, never seeming to end.

"Oh Tim, that was lovely," Tammy said. "I can see why Peggy was so thrilled with you at Charlotte's. I'd love to continue, but I really do have to get back to work."

Tim for his part would also have liked to continue. It wouldn't happen except for a last minute surprise.

After his cock slipped out of Tammy's cunt, she said, "Let me clean you up before we leave."

She spent their last few minutes together licking off the juices coating his hard staff, washing it down with the last of the wine.

Her last words before leaving were, "Thanks for everything, Tim."

That evening, Tim's thoughts went back to Lucy. He wanted to avoid meeting her at Skips where he had experienced so much hurt. So Lucy and Tim met at Frankie's Bar and Grill in a nearby suburb. It didn't take long before Lucy lost it and totally fell apart. She cried uncontrollably.

Between sobs she said, "Tim, I was such a dunce. I got scared when we got serious about each other. I wasn't sure if being married was what I wanted. You were so kind to me, but if you asked me to marry you, I would have said no. So, I thought the only fair thing to do was to break up. I know it was wrong now."

Lucy continued, "I met this guy at a party, and he wined and dined me. He made me feel like a queen. I lived with him for nine months until I accidentally found out he was married with three kids. Jesus, was I ever naive and stupid."

Tim sat across from Lucy without saying a word. He wanted to hear her story, but then he didn't.

She said, "That bastard used me, Tim. For nine fucking months he used me as his private whore. I'm so pissed at myself, although there is one good thing that came from it. I didn't know it when we broke up but now I know. I love you, Tim. I now realize that I have always loved you."

Tim was stunned and shocked and exhilarated all at the same time. Now it was his turn to be scared. He wondered, "Did she mean it, the love thing? Does she really want me back or is this just the blow back from a bad experience?"

Without remembering Josh's advice not to rush into things, Tim said, "When you broke up with me, Lucy, it was the most painful thing that had ever happened to me. I promised myself never to fall in love again. But the truth is, Lucy, I've never fallen out of love with you. I loved you then and I love you now."

So much for Josh's friendly advice.

They dated heavily for three weeks when Lucy asked him to marry her. He still had the ring, yet this time there was no band playing; there was no moonlight dinner; there was no proposal on one knee. At the pizza joint she simply asked, "Do you want to marry me, Tim?"

He smiled and said, "Yes." 

They were married three months later with Josh as his best man.

Two months pregnant with their first child, Lucy and Tim celebrated their first wedding anniversary with Josh and friends at Skips. Sally sat quietly in a corner drinking herself into oblivion.