What If?

March 2012

In this Issue:

• The youth begged her to be his first, but she couldn’t. Could she?
• His wife gives a young man a sexy wedding present he won’t forget
• He always did laundry on Mondays, but now he does her as well
• Chess was all very well, but he had another game in mind
• She visits her daughter at college and learns a few things herself
• She enters a “camel toe” contest and gets a couple of humps
• The doctor was in—all the way in. So were these two young guys
• She was a faithful and loving wife, until she became a biker bitch
• Auction Block
• Close Call
• Mom’s best friend had the wisdom of age, and was one hot mama
• What If?
• And to think, she hadn’t wanted to attend that party in the first place!
• She could just continue reading by the pool—or she could step out
• As with many service businesses, his best earnings come in tips
• Her daughter’s live-in boyfriend turned out to be quite a guy
• Stuck in a nasty funk, he found the best cure known to science
• When she ran into him in the mall parking lot, she just couldn’t resist
• You could see it as an act of mercy, nursing a friend back to life
• Doing his best bud “a very big favor” brought his own fantasy to life
• She’d held out against this radical notion of not wearing panties
• Girl Meets Girl
• SHE LETS HER HUSBAND HAVE HIS FUN AS LONG AS SHE CAN WATCH
• SHE SAID SHE’D BE FAITHFUL ON THIS TRIP, AND SHE WAS—SORT OF
• MEN DON’T GET THAT BIG, SHE SAID, BUT SHE FOUND OUT DIFFERENTLY
• SHE’D ONLY BEEN WITH ONE MAN, BUT SHE SOON MADE UP FOR THAT

I met my future wife when I was home from my senior year in college visiting family and friends, and my friend Art asked if I would do him this really big favor. His brother, a high school junior, had asked a girl to go to their prom but at the last minute broke his invite with her. Art asked if I would take Jill to the junior prom. I think he wanted to get even with his brother.

The idea of taking a 17-year-old girl out didn’t interest me. Art said that of course it wasn’t a real date but assured me that Jill was really a great girl and I would like her, and arranged for us all to meet at a coffee shop.

She was embarrassed too, but we soon found we had a lot in common, like both being on our track, swim and rowing teams! And she certainly wasn’t someone I would be embarrassed to be seen with. She was about five-eight and 135 pounds, with long strawberry blonde hair. While not overly busty, she had a fine figure with great long legs.

Jill agreed to let me take her to her prom. And as strange as the whole thing was, we both had a really great time. I learned that I was the “girl talk” for a long time afterwards.

We stayed in touch, and as time passed saw each other occasionally. Once she was “legal,” things started getting serious between us, and in time I asked her to marry me. By then I was a computer engineer with a good firm, pulling down a good salary, while Jill was attending a community college. Her father really wanted her to get her degree before she got married, and that was fine with us. We set a date for a week after her graduation.

In the year or so before we got married, the firm I was working for relocated, then two weeks before we got married relocated again, this time to Florida. So following our wedding and honeymoon (when I discovered that Jill was still a virgin!), we settled down in Florida. I was making good money, so we bought a house. Yes, it stretched our budget, but we were still able to pay our bills and have money left over for nice things like new cars.

We made friends with all our neighbors, especially Sam and Natalie, who lived next door. They were in their early 50s and retired. (Natalie looked so much like Jill, and was in such great shape, that everyone thought she was Jill’s big sister!) Their house was huge, and had a gorgeous swimming pool surrounded by a large privacy fence.

The first year things were great. We had friends, our family would visit us, and we would fly home and visit them. Above all, we had each other.

We even bought a baby grand piano, which Jill loved to play. However, the firm I was working for got bought out by a bigger firm and all the computer engineers were let go. I was given a great letter of recommendation and a nice severance package, and figured I would have a new job in no time, but that didn’t turn out to be the case.

With money getting tight, I finally landed a job, but it required that I fly to Europe for several months of retraining. Before I left, I asked Sam and Natalie to watch over Jill.

A few weeks after I left, Jill was really stressed because of some “past due” ­notices she received, including one for the precious piano.

Distressed, she put on her bikini and went out in our back yard to get some sun and have a glass or two of wine. It was cloudy, and with no one around, she decided to take her top off. After her second or third glass of wine she fell asleep.

She was awakened by Natalie calling and shaking her. She’d been sleeping for a couple of hours, during which the sun had burned off the cloud cover, and she was burned on her front and back. Natalie said to come over to her place because she had a lotion she could put on that would relieve the pain and also help moisten and darken her skin.

Jill could barely move, but she got her top on and made it over to Natalie’s. Natalie had her go upstairs to the bedroom while she got the lotion. In the bedroom she told Jill to lay on the bed and remove her top. Jill hesitated, but Natalie told her to look in the mirror and see how burned she was.

Jill removed her top and Natalie be­gan to spread the lotion. While she did, she asked Jill what was wrong. Jill told her about being lonely and about our financial difficulties. Natalie, while work­ing the lotion into Jill’s face, shoulders and back, told Jill that when she and Sam got married they had major financial problems. Though Sam was working all the time, putting in as much overtime as he could, bills kept piling up. Finally Natalie found a way to get them paid off. Jill asked how.

Natalie put more lotion on her hands, and as she spread it over Jill’s lower back, she said, “I became a hooker.” Jill told me her eyes flew wide open. She looked at Natalie in disbelief.

Natalie explained that as things got impossibly tight, and Sam was killing himself working so much, one day while she was home there was a knock at the door. The young man at the door said his car had broken down and he’d knocked on everyone else’s door and no one was home. He asked if he could use the phone. Natalie let him in, and he made his call and was told that it would be several hours before someone could come get him because of a major traffic accident.

The young man thanked Natalie for the use of the phone and said he was going to go sit in his car and wait on the tow truck. She said he should probably wait in the house for a while since it was a pretty hot day. She got some iced tea, and they drank and talked. He talked about his job and being on the road for long periods of time, and she mentioned about Sam working so many hours to help pay the bills.

She noticed him looking at her long legs, which were exposed under her sundress. He said he had some special cream that would help give her legs the suntan look. He got it out of his briefcase and asked if he could put some on her. She said yes.

The young man sat on the sofa, put a towel over his pants and had Natalie put her legs over his lap. He started at her toes and massaged her toes and feet. She said it felt great. He kept massaging the cream into her legs—up her calves and then to her knees. The sensation was terrific. Before she knew what was happening, his hands were under her sundress massaging her thighs. She looked at him, and he said that he sure was lonely, and that she had great-looking legs, and that he would love to see more.

Natalie said she was getting pretty horny and let the young man move her skirt up above her thighs, then watched in amazement as he lowered his head and began kissing her thighs and panty-covered pussy. Soon he had his hands on her panties and was pulling them while continuing to kiss her. Then the sundress was completely gone, and he made love to her for the next two hours. Before he left, he thanked her and handed her $500!

All this time Natalie had been massaging Jill’s back. Now she told Jill to roll over. Jill hesitated, not because of being naked, but because she had become aroused and her nipples were hard. Natalie poured more lotion and began massaging Jill’s stomach, chest and breasts.

Natalie said she didn’t tell Sam about her encounter because when he got home that day he was very upset and said he had bad news. He had taken money that was to pay the bill for her car and used it to place on a sure bet. The sure bet didn’t pay off, and someone would be coming the next day to take the car away.

Natalie told Jill she was livid and screamed at Sam for a good hour. He slept in a separate room that night and was gone by the time she was awakened in the morning by loud knocking on the door. There stood a huge guy—he must have been six feet six and weighed 245 pounds. He said he was there to pick up her car unless she paid him $1000.

Natalie said she didn’t have $1000, but she had $50 she would give him if he would leave her car there. He looked at Natalie, then said maybe they could “work something out.” He moved closer to her and asked for the $50. She gave it to him, and he said he would pay the rest if she would be “willing to have some fun” with him.

Natalie said she just stood frozen in place. He untied her robe, and as it fell to the floor, he reached out with one of his big hands and lifted off the nightgown she had on. He picked her up, took her over to the sofa and laid her down, then removed his clothes. When he dropped his pants, Natalie said she nearly died at the sight of the biggest cock she had ever seen. He motioned to her to suck it. While she took in as much as she could, he felt her breasts and fingered her pussy. After several minutes he let out a growl and filled her mouth and throat with come. She swallowed as much as she could.

He proceeded to open her legs and place his mouth over her pussy, then insert his tongue in it. He kept this up until he had her at the point of coming. He stood up and repositioned himself between her legs, and she felt his huge cock prying at her pussy opening. Inch by inch he filled her up. She said she had to reposition herself several times until finally he was all the way in. She never felt so full. Then she felt him pulling out and pushing back in, and he kept the back-and forth motion going for a good 15 minutes, during which he finally pushed her over the edge. After that it wasn’t long before he let out another growl and erupted inside her.

When he was done, he got up and massaged her tits and her pussy with his big hands. He had her whole body trembling. He picked her up and turned her over on her hands and knees, then got behind her and again slid his huge cock in her pussy. Since it was so well lubricated, this time it went in easily. As he pumped and pumped, she came again. He kept fucking her until he pulled his cock out of her pussy and put it up against her asshole. Before she could say anything, he pushed and the head of his cock was inside her. He took his time, and after a few minutes his entire cock was inside her virgin ass. He resumed his pumping action, and because of the tightness of her ass, in less than five minutes he blew another load. He pulled out, and she said she collapsed on the floor.

The guy told her she was really special and he would pay the full amount of the car payment, including the $50. He said his name was Santos and gave her his phone number, in case she ever wanted another good fuck. He also said that if she liked getting fucked and wanted to make some money, he could line up a bunch of guys that would be willing to pay a lot to fuck a good-looking woman like her.

Natalie was relieved when Sam came home that night. Seeing that the car was still in the driveway, he asked if the repo man had showed up. Natalie told him what happened, and what she did so she could keep her car. Instead of being mad, he was excited, and they made love for hours while she told him everything that had happened. The one thing she didn’t tell him was the part about Santos saying he could hook her up with other guys willing to pay to fuck her.

At this point in the story Natalie put more lotion on her hands and massaged Jill’s left leg from the toes up. She told Jill that after a couple of days of thinking, she called Santos, and asked what kind of money he was talking about. He said she could easily be making $500 or more per session, and it was up to her how many sessions she could do in a day or night. He ­figured she could make $2000 a day by fucking four guys in the course of a couple of hours. He also said that unlike most pimps, who take most of the money the girls make, all he wanted was to continue to fuck her.

By now Natalie’s fingers were massaging Jill’s upper thighs, and ever so lightly touched her inner thigh at her ­bikini. Natalie got more lotion and moved to Jill’s other leg, again starting at her toes and working her way up until again her hands were lightly touch­ing Jill’s bikini. Natalie looked at Jill and said that with her body she could be making $2000 a day.

Jill blushed. Natalie suggested that she slip her bikini bottom off so she could get some lotion on the area where it covered her. Again Jill hesitated, but Natalie put her hands at the top of her bikini bottom and pulled it down. Now Jill was completely exposed to Natalie, who stood back and looked at her. Natalie said to forget about $2000, that with that body she could easily be making more than that.

Natalie put more lotion on her hands and massaged the sunburned areas around Jill’s legs and thighs. Her finger slipped and slid across Jill’s pussy. Jill tried to cover her moan, but Natalie heard it. Jill said she was sorry but I’d been gone for several weeks and she missed having sex. Natalie said she understood, and with that slipped her hand back on Jill’s pussy while placing the other hand on one of her breasts and massaging it. Jill just laid there, and soon had fingers working their way in her pussy, making her moan even louder, until she climaxed.

When Jill opened her eyes, she saw that Natalie was taking off her clothes and climbing in bed with her. They kissed ever so gently. Then Natalie started working her way down Jill’s stomach to her pussy. The way Natalie was positioned, as she moved down Jill’s body, her pussy was moving ­closer to Jill’s mouth. When Jill felt Natalie’s tongue slide in her, even though this was all new to her, she did the same to Natalie!

Natalie held onto Jill’s body and rolled so that Jill was on top and Natalie on the bottom. They kissed and sucked each other’s pussy until both of them exploded in a wonderful climax.

As Jill was exploding, she felt something behind her, probing her pussy. She rose up and saw Sam standing there slowly feeding his cock in her pussy! She knew she should stop him, but it felt too good. He pumped and pumped, and soon she knew he had exploded inside her. He pulled his cock out of her pussy but then put it up against her asshole, and like with Nat­alie, before she could say anything it was inside her. All this time Natalie was still eating her pussy and she was in a constant near-orgasmic state.

After several minutes Sam’s cock was fully inside Jill’s ass and he was pumping away. She was amazed that he could stay so hard. He pumped for a good ten minutes, then really pounded into her until he came inside her again. He pulled out, and Natalie let go of her pussy, and they all lay on the bed naked and spent.

Sam said he’d come home, heard strange noises upstairs, and when he came up and saw what was going on, he stripped and joined in. Without thinking, Jill glanced down at Sam’s cock and was startled to see it getting hard again. Natalie reached over and took it in her mouth and sucked him. She looked over at Jill and motioned for her to come closer, which she did. Then Natalie got her to lick and suck Sam’s cock. Soon both ladies were pleasing him. To return the favor, he had them get on their hands and knees and he took his time putting his cock first in his wife, then in Jill. This went on for a long while, and everyone had a wonderful time. Finally Jill got dressed and went home to sleep.

The next morning Jill got up and while taking a shower thought about what had happened at Natalie and Sam’s house. Over the sound of the shower she heard a loud knocking at her door, so she threw her terry-cloth robe on and went downstairs. She opened the door to two large men who introduced themselves and asked to speak to her husband. Jill told them I was at work, and they explained that they were there to repossess the piano. She was extremely upset because she really loved the piano.

The guys told her they needed $1500 or they had to take the piano. She said she didn’t have that much money and began to cry. Marty, the bigger of the two, walked over to her and said he was sorry but it was their job. She said she understood but she loved the piano. He looked at her and said maybe they could “work something out.” Naturally Jill flashed back to Natalie’s story, and asked what he meant. The guys walked over to her and said they’d like to see what she was wearing under her robe. She said she’d just gotten out of the shower, and Marty smiled and said, “Good, now let’s see what’s under the robe.”

Jill stood there. Marty said, “Okay, Sal, looks like we’re taking the piano.”

Jill untied the robe and opened it, and in a flash the guys were feeling and kissing her. Soon Marty moved her to the sofa and laid her down on it, then removed his pants, revealing a cock that wasn’t that long but was bound to be too thick for a comfortable fit. He moved between her legs, and she felt it inch its way in her pussy. After several minutes it was fully inside her, but after some fumbling they fell on the floor and now Jill was on top. She got into a sitting position and felt really full. Then Sal stepped forward and presented his cock to her mouth. She was relieved to see that it wasn’t as thick as Marty’s, and didn’t mind that it was maybe an inch longer. She took it in her mouth and for the first time in her life had two cocks inside her.

After several minutes Sal pulled out of her mouth and walked behind her. She felt his cock searching for her asshole, and Marty stopped his pumping action to allow his coworker time to get fully embedded in her ass. Now the guys started their rhythm, and they soon had her on the brink of climax. First Marty exploded, and then Sal. She said she felt kind of relieved when they pulled out of her, leaving come running out of both her holes.

They weren’t done with her, though. Marty got in between her legs and cleaned her pussy out with his tongue. When he finished, she got up on her knees and sucked the guys, going back and forth. This went on for a long time, until each of the guys had exploded in her mouth. After they cleaned up and were getting ready to leave, Marty said he realized money was tight for her, and he had lots of friends that would love to fuck her and would gladly pay for her services. Jill couldn’t believe this was happening, just the way it had happened to Natalie, as she’d found out only the day before!

When Marty and Sal left, Jill still hadn’t come. She lay back on the couch, still thinking about the experience, and about Natalie’s story, and worked her pussy feverishly until she brought herself to a wild climax.

When she recovered, she cleaned herself up and went over to talk to Natalie. After she told Natalie what had happened, Natalie asked what she was going to do. Jill said she didn’t know, that while she enjoyed the sex, she didn’t think she was ready “to turn pro.” Natalie asked her why not. I was away, she pointed out, and money was tight, and here was a way to make lots of it. She paused, then said, “How do you think we could afford this place?”

Natalie explained that after she had told Sam about her experience, she called Santos and they made arrangements. And for the next hour she told Jill about some of her experiences over the next several years, getting fucked by a lot of guys, a number of times making it with guys’ girlfriends and/or wives, sometimes with the guys watching or even participating. She got into servicing groups unintentionally when she showed up for an appointment and was met by four guys. Her first impulse was “uh-uh, no way,” but when they the guys assured her that they understood they would all be paying full price, she went ahead. In the end she had fucked guys of all races and creeds and sizes and shapes. The biggest cock, she said, and this was another surprise, ­belonged to a short Asian guy she hooked up with while she was on a cruise with another guy.

It was really tempting, Jill told me when I got back from Europe. She kept thinking, “What if?” It seemed so easy. But she realized maybe she and Natalie just were different. Natalie seemed to enjoy it, and she hadn’t really. Maybe she would get used to it if she continued, but she didn’t really want to.

It also occurred to her that Natalie was so proud of having paid for her home by hooking, but hey, we were ­living right next door! True, we weren’t doing such a great job of ­affording our much smaller home, but we would manage somehow. Finally, she realized Sam and I are different. She didn’t see me as “that guy”—the kind who fantasizes about his wife fucking hundreds of guys and getting rich.

I can’t say that I’ve never wondered, “What if?” Maybe it’s just as well that I never had to find out how I would have felt if Jill had called Marty. I made sure she knew I was fine with what already happened—that I would have felt horrible if she’d lost her piano.

I’m pleased to report that it’s all paid for now. Yes, we’ve had our rocky times, and yes, there were times when one or the other of us wondered, “What if?” Still, after a while our finances sort of stabilized, and while we’ll never lead the posh lifestyle of our old neighbors Natalie and Sam, we’ve managed.

Nevertheless, anytime we hit a financial bump, one of us can be counted on to ask the other, “What if?” It always gets a laugh.

—L.E., Orlando, Florida