The MILF

The MILF

A young man gets more than he had hoped for.

As with all this author's stories, this is a work of fantasy/fiction. Just as the story, "Jack and the Beanstalk," is not meant to encourage anyone to invest his life's savings in magic beans, so the author's stories are not to be understood as encouraging extra-marital sex.

Note to the reader: This story is written as a stand-alone story if one reads the following introduction. For a more thorough introduction to the characters in this story the reader could read or skim through the chapters of the story entitled, "What If," written by the same author. Anyone who read the entire "What If," series could skip the introduction to this story.

*

Introduction

Carol was a MILF. She hadn't always planned on being a MILF. In fact, she and her husband, Ted, had been told that Ted was infertile and they would never be able to conceive children. So she would never be the M in MILF. They both liked sex. Actually, before they were married and continuing on after they were married they bought instructional books and videos on sexuality and sexual techniques and studied them. They became very proficient at giving one another pleasure and were continually trying new positions and methods of stimulating their partner and making the most of their sexual relationship.

Carol was multi-orgasmic and could go for hours. Ted had great stamina and control and also a rather quick recovery time, but on those occasions when they engaged in a sex marathon, when Ted reached the point where he was just all fucked out, Carol could keep on going. This was certainly not an everyday thing. Both of them had careers and the responsibilities of normal life so a session of knock- down, drag-out, sex-until-you-drop was reserved for relatively rare and special occasions. Nevertheless, it bothered Ted, that on those occasions he could not provide his wife with complete satisfaction nor bring Carol to that all-fucked-out place where she was simply sexually exhausted. And so they introduced toys, fantasy and porn to their marathon sessions.

Carol was very attractive. She worked at being attractive. She had long blonde hair, blonde due to the skills of her hairdresser. She had surgically enhanced breasts. She worked out and had a narrow waist and a flat belly. Her hips were quite wide, but she carried the wide hips and large breasts well because she was tall and had a relatively large rib cage -- which balanced her wide hips. She wore makeup skillfully and had pierced ears, pierced nipples, a pierced navel and rings in her pierced inner labia.

Some time after they discovered that they would not be able to conceive children, they discussed the role of sex in their marriage and came to the conclusion that while for most couples a primary purpose of marriage and sex was to have children and then preserve the family as a unit, that need not be the case for them. They could view sex as more of a recreational activity. As such, an alternate way to have marathon sex that would bring Carol to the point of sexual exhaustion would be to invite another person to join them.

As they considered what type of person this might be, they considered that a young man right out of high school and still needing an education to productively enter the workforce might be a good candidate. It would be hard for him to compete with Ted as a breadwinner and an equal partner in a marriage. He would not be of an age where he wanted to settle down. And they knew from their own experience that there were young men out there, good young men, who were not that flashy in high school. They were too timid to go on dates -- afraid to ask girls out because they felt inadequate. And now that they were out of high school they were feeling even more inadequate. They were afraid that any girl they asked for a date would be more advanced in their sexual experience than they themselves. They were afraid that any fumbling attempts to move forward with a girl would be rebuffed or held in derision. Some of these young men felt like they were on a downward spiral. They were afraid to date because they were inexperienced. So they didn't date and thereby forfeited any chance of gaining experience. Such men felt lost and hopeless.

If Ted and Carol could identify such a guy and offer to teach him how to become a skilled lover, they would be doing the young man a favor. If then the young man would join Ted and Carol in a marathon session of sex every now and then, bringing Carol to the point of complete sexual exhaustion -- that would be a win-win situation. And so it was that over the past eighteen years or so Ted and Carol had taught a number of young men (and a few young women) about how to please their partner and receive pleasure from their partner. These young men had joined Ted and Carol a few times for marathon sex and also to give Carol the unique sensation of a double penetration.

But the best laid plans of mice and men sometimes go astray. After Ted and Carol had changed their thinking about sex and were treating it as more of a recreational activity that they enjoyed with one another but which also occasionally involved other people, they were asked by some of Ted's relatives to consider adopting twin children whose parents had been killed in a tragic accident. Ted and Carol were the right age for bringing up the children and were established in their careers. Furthermore Ted and Carol's last name was the same as the children's last name, so adoption would not change their names at all. The children's grandparents really liked this idea. After careful consideration Ted and Carol said, "Yes." But the toothpaste was out of the tube as far as recreational sex and involving other people was concerned. Ted and Carol would just have to be thoughtful and careful in the way they involved others.

The story that follows was precipitated by an event that happened the summer after Ted and Carol's adopted children, Tommy and Sarah, had graduated from high school. They had both also celebrated their eighteenth birthday. It was a Saturday and Tommy had gone out to spend some time with his friends, Andy and Greg, who had also recently turned 18. One of the characteristics of the house in which they lived was that it was heated by forced air. The forced air ducts conducted sounds from one room to another. The sounds were not evenly distributed throughout the entire house, however. Fortunately, the children could not hear what went on in their parent's bedroom. But it did occur at times that when Carol was preparing supper in the kitchen, if Tommy had friends in his room and Carol was working by the sink, she could hear some of their conversations. She tried not to eavesdrop, but more than once she had heard the boys refer to her as a MILF. Now that all the boys were 18 and Tommy would soon be going off to college, Carol decided that it would be fun to turn up her MILFness just a little bit for their benefit. This is how it happened.

Sarah was going to be gone all afternoon. Ted and Carol talked about what Carol had in mind for the boys, and Ted conveniently went over to his parents' house to do a brake job on his dad's car so he would be out of the way. The boys -- Tommy, Greg and Andy -- had gone bowling and Tommy had told his mom that he thought they would be back about 3 o'clock in the afternoon. At 2:45 Carol went into the backyard wearing one of her tiniest bikinis. She first put up the badminton net. Then she got out some garden tools and started weeding in a flower bed. Soon the boys came up the driveway to the gate that led to the back yard. There was a privacy fence all around the back yard, even across the driveway. As the boys entered the back yard Carol feigned surprise, exclaiming, "Oh. my goodness, I've been so busy I lost all track of time. Oh! I'm so embarrassed -- in front of you in just this wisp of a swimsuit." And she got up from her kneeling position making as though she was going to run into the house.

"That's all right," said one of the boys. "It's such a hot day it would be a shame for you to cover up just because we're here. Besides, I think it's a very cute swimsuit. Don't you agree?" he asked the two other guys. They both readily agreed.

"Well, I do have to agree with you that it's hot out today, and you've walked all the way from the bowling alley. Can I offer you something to drink? Lemonade? Iced Tea?" she asked.

"That would be great," was their reply. Carol walked across the back lawn and up onto an elevated patio/porch which extended across much of the back of the house. Patio doors allowed one to go from the patio into the kitchen. Carol climbed three steps onto the patio. There she had a pair of four inch wedge sandals waiting for her. She put them on and then moved across the width of the patio to the patio doors. She reappeared shortly thereafter with two pitchers, one of iced tea and the other of lemonade which she carried across the patio to a table near the steps that went into the yard. After setting them down, she returned to the kitchen, swaying her hips which were only covered by the minuscule bikini bottom. She came back carrying a bucket of ice. Setting it down she returned to the kitchen one more time. She came back with four glasses. All eyes were glued upon her as she walked back and forth upon the patio. She thought for a moment about saying, "Oh, I forgot the straws," as an excuse to make a fourth trip, but decided the three trips were enough. The boys were still standing there in the back yard staring at her. She invited them up.

As they were drinking their drinks, one of the boys spotted the badminton net. "Let's play badminton," he said. But they quickly realized that there were three boys. One would have to sit out every game . . . unless Carol would join them and they could play doubles. Carol was glad to join them, but asked them to wait a minute while she changed into shorts and a blouse. The boys told her that changing was quite unnecessary; that they really appreciated the eye candy. After thinking it over, Carol countered that she would remain in the swimsuit if they would put on swimwear that she would provide for them and that would be eye candy for her. Hormones won out and they consented to her terms. She went to her room and got out three very stretchy thongs, that would stretch enough to hold the guys' equipment. She gave them privacy in the kitchen and they came out both embarrassed and excited wearing such brief swimwear. They played two games, switching partners each time. Their play was horrible because their attention was on Carol who had to repeatedly adjust her breasts in her small top, ". . .to avoid a wardrobe malfunction."

They broke for another glass of lemonade or iced tea. Then Carol apologized to them. She had made them wear thongs while she got to wear a bikini (although it was the smallest bikini any of the boys had ever seen in real life). "If you can wear a thong, I should be willing to wear one too," she said. With that she removed the bottom to her bikini revealing that under it she was wearing a dental floss micro thong. They played one more game as Carol moved around with just two triangles covering the centers of her breasts and a tiny triangle that covered not much more than her clitoris and its hood. Carol announced that she had to go in to begin making supper. But first she slipped on the wedge sandals and cleared the table of the pitchers, glasses and ice bucket -- in three attention riveting trips. She did put on shorts and a crop top to make supper. The boys went up into Tommy's room to change. As she prepared things at the kitchen sink she heard references to herself as being a MILF. Then there was a very quiet time after Tommy announced that he had some pictures of his mom on his computer and asked if anyone would like to look at them. They were evidently looking intently.

So far the Introduction

It is now October. Tommy has gone out of state to college. Andy is attending an in-state college but is living on campus. Greg is attending a local college (as is Tommy's sister, Sarah) and is living at home.

Out of the blue, Tommy received an e-mail from Greg. In it he wrote a few things about how life was treating him and asked about Tommy's experience at college so far. But then he wrote: "Could you send me a picture of your mom?"

The next day, Tommy replied in kind, writing about his classes, his dorm and his roommate. He finished by writing: "About the picture -- I trust you want a picture the likes of which you saw on my computer this summer -- not my mom's passport photo."

That night Tommy got a reply: "You're funny."

Tommy almost immediately replied to this: "Because you want a photo of my mom, I really feel like my mom is the one who should give it out. I'd feel pretty pissed if my mom had taken pictures of us in those thongs, and then, without my permission, had given one to a friend of Sarah who asked for it. I hope you understand. Those photos are kind of sensitive. I have thought already that I may have made a mistake in showing them to you and Andy without mom's knowledge or permission.

"I'd feel much more comfortable if you would ask her. I've seen my dad take plenty of photos of her, so she has them. And the more I have thought about it, the more I am convinced that mom had that whole afternoon set up. She liked us seeing her in that tiny bikini. And if she did, my guess is that she would be happy to give you a picture or two. Call her up some evening on her cell phone: XXX-XXX-XXXX. I really think you have nothing to lose and will probably get what you want."

Tommy got a one word reply: "Thanks." He did not know whether this was sincere or sarcastic. But knowing Greg as he did, he decided it was sincere and almost put the request out of his mind. He had made it none of his business. It would be between Greg and his mom.

But then the next day as he was walking back from class, he thought that maybe he ought to give his mom a heads-up just to let her know the call might be coming and to let her know that he, Tommy, had given her cellphone number to Greg.

Carol wrote Tommy back and thanked him for the heads-up and then went on to write: "Greg has always seemed to be a nice guy, polite, caring and responsible from what I saw of him. Am I reading him right or are there things I should be careful about?"

Tommy replied: "Greg's a good guy. Andy is more fun loving and adventurous and the one I would name as my best friend, but Greg is the one who has put the brakes on when Andy was about to overdo it and I was ready to follow Andy's lead. If, for instance, you gave Greg an electronic photo of you and told him not to show it to anybody else, he wouldn't. He would not betray your trust. And he comes from a good family. You can feel comfortable with him."

Greg, at first, just felt too uncomfortable about asking Tommy's mom for a picture -- a revealing picture, a sexy picture. He figured this was just a passing notion on his part and after a while the thought of having a picture of Carol in a bikini would not cross his mind any more. But it didn't work that way. Weeks later he was still wishing he had a picture of Carol. He almost wrote Tommy again, admitting that he was too chicken and hoping Tommy would feel sorry for him and send him a picture. But in the end he knew he could not do that. If he wanted a picture he'd have to ask Carol. He had her phone number. But he really felt that asking for a picture of her was something that he should do face to face.

But he couldn't just show up at their door. What if Ted would answer the door. He was not prepared to say to Ted, "Can I speak with your wife?" And what if Sarah answered the door. Sarah. He'd never told anyone but if there ever was a girl he would like to date it was Sarah. But she was gorgeous and popular and a cheerleader, for crying out loud. And he was just her brother's boring friend. He didn't stand a chance. What if Sarah answered the door. He'd run away rather than say, "Can I speak to your mom?" It took him a while to come up with a plan.

Finally, close to Thanksgiving Carol got a call.

C: Hello?

G: Is this Mrs. Watkins?

C: Yes it is. To whom am I speaking?

G: This is Greg -- one of Tommy's friends. I've been over to your house a few times. Remember me?

C: Of course, Greg. How are you doing?

G: I'm doing fine -- going to classes -- I see Sarah every now and then although we are not taking the same courses. I'm looking forward to the little break for Thanksgiving, but I'm going to have to work Black Friday. I'm not looking forward to that. I hear it's one step away from being out of control.

C: That's what I've heard, too, but I'm not a Black Friday shopper, so I do not know from experience. To what do I owe the pleasure of this call?

G: There's something I'd like to talk to you about, but I'd like to do it face to face. If I bought you dessert, would you be willing to meet me at (a chain restaurant) some evening this week? I don't think it will take much longer than it will take to eat dessert.

C: That's an offer that sound's too good to turn down. What day and time did you have in mind?

G: Would this Wednesday at 8 o'clock work for you?

C: That would be fine. Is there anything you want me to think about ahead of time?

G: No. Just come with your sweet tooth.

C: Will do. Thank you. See you Wednesday at 8. Good-bye.

That evening Carol talked with Ted. Carol was pretty sure she knew what the topic of conversation would be. Ted, always thinking of his hot wife, said, with a twinkle in his eye, "What are you going to wear?"

Carol twinkled back knowing Ted loved dreaming up hot outfits for his wife and said, "I don't know. Do you have any ideas?" Ted did. Carol would knock Greg's socks off.

Carol pulled into the well lit parking lot at 7:55 hoping Greg would be there already. She pulled to a parking space close to the far corner of the almost empty parking lot. She shut off the engine and looked for Greg. He was there, standing by the entrance to the restaurant. Carol slowly got out of the car. She was wearing a black long-sleeved catsuit. It fastened around her neck, but then in front widened out into an O which dropped to just below the bottom of her breasts and was wide enough that it exposed her breasts almost to her nipples. The catsuit was made of a stretchy and shiny material. Because Carol was fairly tall, her height pulled the front of the suit into her vulva, showing off a distinct camel-toe. In back it was so tight that the center seam pulled into her crack, so that each cheek of her ass was clearly defined. Helping with that was also a wide black leather belt which she wore tightly around her waist. She wore it backwards -- the with buckle in the middle of her back -- in order to emphasize her relatively small waist and flat abdomen. The top was so tight that one could clearly see the barbells that adorned her pierced nipples. As she walked across the parking lot one could not see the top of her catsuit, for she wore a soft black lambskin peplum-styled jacket which also nipped in at her waist. However the deep V of the collar gave one ample view of her cleavage. On her feet was a black pair of knee-high boots with four inch heels. Long earrings dangled from her ears, and her blonde hair cascaded in ringlets down to the middle of her back. She had put on makeup the way she would if she were going to a nightclub. She carried a small clutch purse.

At first she was so far away that Greg was not sure that the vision walking toward him was Carol, but from the moment he laid eyes on her he could not look away. And as she drew closer he realized that this was Carol. As Carol drew closer still, she tried to remain in the light as much as possible. She put a gentle sway into her hips as she encouraged herself, "Work it, Carol." When she got to the entrance she extended her hand and said, "Hi, Greg. Good to see you."