Cindy sat at her dining room table and sipped a glass of wine. In front of her were two letters and two small piles of photos. Aside from some soft music coming from the stereo the large house was empty and quiet, as it had been for much of the past six months.
She finished addressing the envelopes and set her address book aside. She sighed heavily and reached for the stamps. She knew writing letters was a little old fashioned, but there was something far more satisfying about a letter than an email. She had been writing a lot of letters lately, but she had to do something to keep in touch with her family. She put the postage on one envelope and sat thinking for a moment before cursing herself for not writing down the necessary postage for her other letter. With all the letters she had sent recently she should remember the correct amount by now, but the amount escaped her and she had to go to the post office to find the correct amount. Maybe she did it subconsciously to give herself something to do. She had been alone now for most of the past six months and she wondered if she intentionally forgot the postage just to give herself an errand to run.
About six months earlier Jim, her only son, left for an overseas study program. He had been accepted into an exclusive program and would be spending his junior year of college studying overseas. Cindy was overjoyed for him and very proud, but she also knew it meant she wouldn’t see much of him for about a year. Other than a winter break, he wouldn’t have the opportunity to fly home. He had several other breaks from school, but none were long enough to warrant spending the money to fly home.
Jim was Cindy’s only child and had always been the apple of her eye. This was, by far, the longest amount of time she had gone without seeing him. She was very much looking forward to his winter break that was now about 7 weeks away.
This time away from Jim had been especially hard since Dan, Cindy’s husband, had been away from home a lot lately. Just before Jim left for his exchange program Dan had been transferred to a new position with his company. The new job offered lots of exciting challenges and a healthy raise, but it also meant he would be traveling most of the time. He would now spend almost 80% of his time on the road, at least at first, but Dan assured her that once he got settled into the position he would be spending a lot less time on the road. It turned out, much to Cindy’s disappointment, that Dan actually spent much more than 80% of his time on the road. Even when he was home it sometimes still felt like he was on the road. He was so absorbed in his new job that it seemed that was all he could think about.
Although Cindy had been very lonely for most of this time, it hadn’t been all bad. Mostly out of boredom, Cindy started going to the gym. At first she was just looking for something to do and going to the gym seemed like a good way to kill an hour or two each day. When she signed up for the gym membership it came with a few sessions with a private trainer. Cindy was almost embarrassed at how much she enjoyed these sessions with her very handsome, very young personal trainer. His touch on her arm and back sent electric charges through her body that served to remind her how lonely and horny she was. Maybe it was the attention from the trainer, or maybe she was just thankful for something to do, but she really enjoyed the gym and made a habit of spending a long time there each day. She found herself looking forward to the gym more and more, especially after she began noticing the changes to her body and her attitude.
Cindy had never worked out regularly before and it wasn’t long before she noticed the effects of her workout regimen on her body. She wasn’t grossly overweight by any means, but she knew she had been carrying around more than a few extra pounds for a few years now. She tried to be careful about what she ate, but the years of not exercising added up. Once she noticed the pounds disappearing it was like an addiction. She started paying even more attention to what she ate and got more serious about working out. Instead of just going to the gym to hang out, she now went to work out and made much better use of her time.
In a surprisingly short amount of time she found herself much closer to her “ideal” weight and feeling better than she had in years. Her new look soon led to a new, more confident attitude. She did some shopping and almost completely replaced her wardrobe. Her new clothes had a slightly sleeker, sexier look than the clothes she had worn for years. After a while, the face in the mirror didn’t seem to match her new body and attitude. She invested in laser eye surgery to eliminate the thick glasses she had worn for almost as long as she could remember. She then visited an upscale salon and received a full make over and new look. They not only changed her hairdo but also advised her on new styles and colors of makeup that really made Cindy look and feel great. With all these changes she barely looked like the person in the family photos on the mantel, but she loved her new look and the way she felt.
As she felt sexier and better about herself she found that she felt more honry than ever. She looked forward more and more to Dan’s stops at home, and yet each time she was more and more frustrated and disappointed when Dan left again. Despite her new look and how much more sexy and flirty she felt, Dan paid very little attention to her and almost completely ignored her sexually.
Each time Dan left Cindy questioned what she was doing wrong and wondered what she did to make him so disinterested. Deep down Cindy knew that whatever problem there was had existed for a long time. The fact that Dan was traveling so much and only home periodically served to amplify something that had actually been going on for nearly two years. Dan had gradually been drifting away from their relationship and had slowly become more and more engrossed in his work and other activities. His new job gave him added reason to focus on work at the cost of ignoring Cindy. She had hoped that her new look would catch his interest and spark things, but every time he left she had to confront that whatever was going on with him was much deeper and caused by things that a sexy new look wouldn’t be able to fix.
Still, Cindy felt like she had to try as hard as she could to rekindle things with Dan. She still loved him, or at least she loved who he used to be, so she felt like she had to keep trying. She felt nervous and a little self-conscious about her latest attempt, but she knew this was something very likely to grab his attention since she had always resisted this kind of stuff before. Gathering her courage one last time she hurriedly shoved the two stacks of photos in the envelopes. She knew it was silly, but she felt like she had to hurry or else she might still chicken out and change her mind.
Finally, once the envelopes were sealed, she felt calmer. Now, somehow, it felt like there was nothing she could do, so she grabbed her keys and drove to the post office. She bought the postage for the overseas letter to Jim and dropped the letter for Dan in the mailbox. She knew the letter to Dan would get to the field office where he was currently based the next day and that it would take a few days longer for Jim’s letter to arrive. Her stomach fluttered and she wondered how long she’d have to wait for a reply.
Dan had been on the road for an especially long time this trip and Cindy could hardly wait to hear his reply. She checked her computer frequently, but nothing showed up. Finally, Cindy called Dan a few nights later. They made all the usual small talk and updated each other on what they’d been doing, but the whole time Cindy waited for him to comment on her letter. To her surprise and shock, the conversation ended without a single word from Dan about the letter. After hanging up, she sat and stared at the phone for a few minutes trying to sort out her thoughts.
She had worked hard on her letter and had carefully crafted it to be teasing, flirtatious, and playful. It was, by itself, not shocking or completely out of the ordinary from her past letters. However, when combined with the photos she had enclosed there could be no mistaking the double meaning in her words and what she wanted him to do. The fact that he said nothing was almost unbelievable.
When Jim received his letter he ripped it open and quickly read it. He was having a great time and a wonderful experience, but there was a small part of him that was a little homesick. He and his mom, in particular, had always had a great relationship and were almost as much friends as they were mother and son. Jim wouldn’t trade his overseas opportunity for anything, but he very much looked forward to his visit home in a few weeks. It had been a long time since he was home and he knew this would be his only chance to see his parents for quite a while.
He read her letter quickly. It was more like a letter from an old friend than something you would expect a mother to send her son. Her letter told him all about her new work out regimen and described all the wonderful benefits she had been feeling. Her letter talked about how she had pulled out all the stops and given herself a new look. She said she felt about 10 years younger and better than she had in a long, long time. The letter continued and said she was sure he would enjoy his “new and improved” mom. The PS of the letter said she included a few photos of her new look as a “teaser” until she would see him in person.
Jim reached in the envelope and pulled out a second, smaller envelope with the photos. He pulled out the photos and gasped in utter shock. His hand jumped and he almost dropped the photos on the floor as he tried to process the image in the top photo. Finally, his hand dropped to his side and he stared dumbly at the wall with his mind spinning.
After several long moments, Jim lifted his hand and slowly looked down at the photo. He somehow half expected that he had merely seen it wrong and now that he looked again the photo would be completely different, sort of like when you see a photo and can’t make sense of it until you look again and suddenly the image becomes clear. However, the image in the photo was just as it was before.
The photo definitely showed off his mom’s new look. He could see her new hairdo, the stylish new makeup, and she looked very different without her glasses. He could also see right away that she was fitter and more toned than he had ever remembered seeing her before. Despite all these changes, Jim noticed all these things in a secondary way. Even as he noticed these things, he was far more occupied with trying to make sense of his mom’s pose. She was wearing a very sexy business suit, but it was far more revealing and sexual than anything you would actually see at an office. Her skirt was impossibly short and tight and was slit up one leg almost to her hip. Jim could easily see the tops of her black stockings and the garter belts hugging her thighs until they disappeared under her skirt. Her top was white, very tight, and had enough buttons left open to reveal plenty of cleavage and the edges of her lacy, black bra. Her jacket matched her skirt, and in the photo she looked like she was in the midst of pulling the jacket off. To top everything off, she stared at the camera with a look of sexy, authoritative control.
He slowly flipped through the stack of photos. The photos gradually showed her stripping out of her clothes. In each one she had removed more of her incredibly sexy outfit and revealed more of her toned, fit body and lacy, sexy underwear. In the final photo she had removed everything except the garter belt, black stockings, and spike heeled shoes, and she smiled wickedly at the camera. Her legs were parted teasingly, but not quite enough to completely reveal her pussy. However, he could plainly see her trimmed pussy hair and her big, surprisingly delicious looking tits.
Jim set the photos down on the table and closed his eyes for a second. His head was pounding so hard it felt like it might pop open. His chest was so tight he had to struggle to catch his breath, and he felt like he might be sick. He had never before been so utterly shocked by anything in his life. He didn’t know what to think. On one level, the woman in the photos barely looked like his mom. The mom he remembered easily looked 10 years older than this woman, wasn’t nearly as athletic looking, and probably weighed at least 20 pounds more. If it hadn’t been for her letters describing her work outs and her new look, Jim probably could have been fairly easily convinced that these photos were of an entirely different woman. However, he had received her letters, he did know about her new look, and he knew that this was indeed his own mother.
Jim picked up the letter again and re-read it several more times. He hoped that something in the letter might help him make sense of the photos. Finding nothing that helped, Jim again turned to the photos. On a hunch, he flipped them over and spread them out on the table. There, on the back of the last photo in his mom’s familiar and distinctive handwriting, was a short note that read:
“Like what you see? Want to see more? Email yournastyteacher at this address…”
Underneath she had written an email address of yournastyteacher with an account from a fairly small ISP that had started near his hometown. It featured free email accounts that could be set up anonymously and advertised itself as a way to keep the bigger internet companies from tracking you while you were online. A few of Jim’s friends had used these email accounts for sending or receiving messages when they didn’t want anyone to know it was them doing the sending or receiving.
Jim could barely sleep that night and had a hard time concentrating on his studies the next day. Things got better very slowly over the next several days as Jim tried to keep his mind from wandering during classes or when he was supposed to be studying. However, he still spent nearly every free moment thinking about the letter and trying to make sense of it.
A few days later Jim’s friend dropped by his dorm room to study for an upcoming exam. Jim had a small, single dorm room and sometimes he and his classmates used his room for quiet study groups since most of them lived in noisier off campus apartments or larger dorm rooms with roommates. When they finished studying they cleared their books off the small desk. By accident, Jim’s friend knocked over a pile of papers on the edge of the desk and, much to Jim’s shock and horror, out spilled the envelope with his mom’s sexy photos. One of the photos slipped out of the envelope and immediately caught his friend’s eye.
“Holy shit!” his friend exclaimed excitedly. Before Jim could protest his friend quickly thumbed through the photos until he was staring, wide eyed at the naked photo of his mom. “These are the hottest fucking pics I’ve ever seen, where the hell did you get these?”
Jim answered that a friend from home had sent them. His friend went on and on about how hot the photos were and how he would do anything to have a chance to fuck a hot older woman like that. “You are one lucky man,” his friend said as he handed the envelope back to Jim. “You must really be looking forward to winter break so you can go home and see her.” Jim nodded his agreement, but his stomach tied in knots with fear that his classmate would see the family photos on his desk and recognize the naked woman in the photo as his mom.
After his friend left Jim let out a huge sigh and laughed at the irony of his friend’s statement. If it was a photo of anyone else, Jim would be counting the seconds until he could go home and fuck her. Hot older women had long been a particular fantasy of his. Over the past several months he had spent many, many hours surfing the internet on “hot mom”, “milf”, and “sexy older women” sites. His favorite jerk off fantasies involved a sexy teacher or boss, the hot mom of some anonymous friend, or some other random older woman he had seen during the course of his day. There was something incredibly sexy about an older woman. He had never even been close to being with one, but he imagined they would be confident and skilled at fucking way beyond the handful of younger women his own age he had fucked.
Had his mom known this about him? Is that why she sent those photos? Had she intended to play directly into one of his most favorite fantasies? Her PS kept popping up into his mind. She said she was sending the photos as a “teaser” for his visit. What did that mean? Was she intending to show him more of the same when he came home? It almost seemed too crazy and impossible to believe, but yet he seemingly couldn’t rule it out completely. After all, why else would she have sent him the photos?
As had become a habit, Jim spread the photos out on his desk and looked at them again. His eyes scanned the series of photos from beginning to end. Without thinking he turned to his computer and opened his internet browser. He quickly went to the log in page for the provider of his mom’s email account and clicked the button to create a new account. He wasn’t sure what he was doing or why he was getting an anonymous account. She knew she had sent him the photos, so she probably wouldn’t be shocked if he replied using his school or personal email. Still, it seemed that for something like this he needed a clean account that couldn’t be traced back to him.
He quickly created a new account and then stared at the screen as the cursor blinked in the subject field. He was tempted to just shut off his computer and try to sleep, but then he gathered his courage and reached for the keyboard. He sent a message with no subject. He really didn’t know what to say, so he decided to keep it very short to see what she had in mind. His message only said, “Received your letter. Have been enjoying the photos. Would love to see more.”
He quickly hit send and then panicked and wished he could pull his email back. How could he have sent the message? Did he mean what he had said? Did he really enjoy the photos? Did he want to see more? Whenever he thought about these questions his head hurt and his chest pounded. He wondered if he had just made a huge mistake.
It had taken Cindy a long time to convince herself to take and send the sexy photos to Dan. She had known for a long time that Dan liked to role play during sex. She had never really been that excited by it or that into it before, but she had done a little to try and keep Dan happy. She knew that Dan liked fantasies where she played strong women in positions of power over him. He wasn’t into S & M or anything like that, but he loved pretending that she was the stern principal and he was a misbehaving student or that she was his strict boss who could make him do anything to keep his job and keep her happy. It was the former that she was going for in her photos. She picked an outfit that would resemble something a school teacher might wear, but much, much sexier, and then created the “yournastyteacher” email account to let him know the game she had in mind. She was so sure her photos and new attempt at role playing would grab his attention that she was bewildered that Dan hadn’t emailed her right away.
She had almost given up checking her new email account out of frustration from his slow reply, but she forced herself to check periodically hoping something would happen. Her heart jumped and she gave a relieved sigh when she saw that she had one new message. She didn’t recognize the email address and smiled thinking that Dan wanted to embellish the role playing by creating his own fake email address for the purpose of their game.
She read the email. She had perhaps hoped for more, but at least he had replied. She took a deep breath and thought about how to respond. Finally, she decided that the only way to go was all the way. She closed her eyes and got into her character. She imagined what a nasty, slutty, horny teacher would say to her student. She took another deep breath and focused on staying in character as she brought her fingers to the keyboard and started typing.
By the time she finished and hit send her pussy was dripping wet and aching for attention. She immediately stripped naked and pulled her trusty dildo out of the bedside table. She didn’t know if she would have been able to survive these past few months without her dildo and sleek vibrator. The dildo easily slipped inside her dripping wet pussy and she fucked herself deep and fast. It only took a few moments before she exploded into a wild orgasm that left her gasping for air for several long moments after her finished cumming. Before shutting off the light for the night Cindy giggled and thought that maybe Dan had been onto something all along with this role playing stuff.
Jim felt a flash of excitement and shock when he saw a new message from “yournastyteacher” in his new email account. He opened the email and found a long reply to his short message. He started reading and couldn’t tear his eyes away. The email was hotter, nastier, and far more graphic and wild than anything Jim had read before. The email scolded him for being such a disobedient student and described, in vivid detail, what she wanted to do to him to “teach him a lesson”. She wrote that she wanted to tie him up and dance naked for him. She described how it would make her pussy wet and her nipples hard to see him struggle against his restraints as his hard cock waited for her mercy for release. She wrote that she would make him lie on his back while she sat on his face and that she wouldn’t move until she was completely satisfied and he was soaked in her juices. She said she would make him suck her pussy until she came at least two or three times. She then wrote that if he had been a good boy and followed her directions, she would finally offer him some relief. She described how he would cum as soon as she touched his cock and how she would scoop up all of his cum with her fingers and slowly feed it to him. She continued that she would coax his cock back to its full size and fuck him over and over until he was so tired and worn out that he wouldn’t be able to get hard again for several days.
As soon as he reached the end of the message Jim immediately jumped back to the start and read it again. He had been rock hard since he was a few sentences into his first reading, but now his cock was so hard he couldn’t ignore it any longer. He quickly pulled off his pants and as he read the message again he stroked his cock. He didn’t even reach the end of the message before he groaned and sent a huge load of cum flying all over his lap.
The next day Jim replied to her message, keeping in character as the disobedient student, and described what he would want to do to show his appreciation for her taking the extra time to ‘tutor’ him. His email wasn’t as skilled or dramatic as her message, but he was rock hard again by the time he hit the send button. This time as he stroked his cock he pulled out the photos and spread them on his desk. Despite his fascination with them, he hadn’t yet jerked off while looking at them. He couldn’t stop himself now as he gazed at them wantonly while his mind replayed the sexy words from her email. He imagined that this person in the photos really was his teacher and that they did all the things she described. Very soon, he came with a long moan.
This became a regular occurrence over the next several weeks. Nearly every day they traded email equivalents of phone sex, remaining in character the whole time. In their mutual fantasy they had now shared several long, sensual fucks and a series of quick encounters in her office or in some other semi-public location. The sum total of her messages was beyond anything Jim could ever have imagined. Her messages always left him with his cock rock hard and needing relief. Sometimes he jerked off rereading her messages and sometimes he jerked off looking at her photos. By now, he had practically memorized every detail of each photo she had sent.
Just a few days before he left for his trip home on winter break he received one final email. This one was shorter and didn’t describe them fucking or teasing. Instead, this email said she had let him get away with his actions for far too long. She said it was almost time for her to teach him a lesson and then it listed a specific date, time, and location for their lesson. She closed the message by telling him to respond if he was man enough. The location was a fairly upscale hotel on the far side of his hometown. He knew of the place but had never been inside.
Jim immediately responded and affirmed that he would be there. After he hit send he looked back through his email inbox. “What the fuck am I doing?” Jim said out loud. It seemed too crazy to be believed, but yet he had been carrying on an explicit email affair with his mom for that past month and a half and now he had just set a date for a ‘lesson’. What the hell was happening? What was this ‘lesson’ going to be? Part of him imagined that she had planned this whole seduction and was now waiting to meet him at the designated spot to fuck his brains out and teach him a ‘lesson’ about sex. Even as he thought it he knew it was too crazy to be true, but he struggled to come up with another reasonable explanation.
As he rode the train to the airport for his flight home he wondered how he would respond upon seeing his mom. How would she respond to him? Would things be normal or weird between them? What would happen on their “date” night? He finally decided to push these thoughts aside and figured he would just play it by ear and figure it out when he got there.
Cindy had enjoyed their email affair very much. She enjoyed the challenge of staying in character and coming up with wild and teasing scenarios to describe for him in her messages. She was interested that Dan almost seemed nervous at first in his messages, but eventually he warmed up and soon was definitely in the swing of their little game. She enjoyed their virtual role playing far more than she expected and had been wildly horny almost constantly lately. She used her vibrator and dildo frequently, but she longed to feel Dan’s cock. She could sense his excitement and passion from the words of his emails and she looked forward to having him energized about their sex life again.
Both Dan and Jim were scheduled to arrive at the airport on the same day just a few hours apart. Cindy was so excited on the way to the airport that she could barely contain herself. Dan’s flight arrived first and Cindy fantasized about them finding some forgotten nook in the airport and sharing a quick fuck before Jim’s flight arrived. Cindy’s fantasy was partly spoiled by the fact that Dan’s flight was late and didn’t arrive until only a few minutes before Jim’s. Still, Cindy looked forward to the excited response she would certainly get from Dan and she imagined that it still might be possible for them to sneak off and make out somewhere like two horny high school kids. Much to Cindy’s shock, Dan’s response upon seeing her wasn’t exactly excited. He looked more tired than anything and greeted her with a quick kiss and hug. It was nothing like the greeting she had expected or that she had planned to give him. As they walked over to meet Jim, Cindy wondered how the guy who could have shared such explicit, exciting emails with her over these past few weeks be the same guy who just greeted her with lukewarm enthusiasm, at best, upon seeing her.
It wasn’t as if Cindy hadn’t dressed for the occasion. She made sure her hair and makeup were done perfectly and accentuated her look with freshly painted fingernails and the perfect amount of jewelry. She selected a dress with a low neckline to show off a perfectly teasing amount of cleavage. The dress wasn’t overly short, but she thought the way the fabric hugged her hips and ass did a particularly good job of showing off her new figure. She topped off her outfit with a sexy pair of open toed high heels that accented her figure and added a very sexy sway to her hips and ass when she walked. Despite this, Dan greeted her as if she had been wearing an old pair of sweats and oversized sweatshirt.
For a moment, Cindy pushed aside her disappointment as Jim exited the gate and came into view. Jim’s greeting was much warmer and happier than Dan’s had been. They gathered their baggage and Jim and Cindy chatted about his trip and his recently completed classes and exams.
Jim was far more nervous than he had been in a long time. He was worried that once he saw her everything would be weird and awkward. He didn’t know how he would react to seeing her or how he would keep his composure. His heart jumped into his throat and his cock twitched involuntarily when he first saw her. As they hugged Jim wondered if she could feel his semi-hard cock pressing against her. Her outfit didn’t help his situation. It wasn’t anything like her photos, but it was certainly the sexist outfit he had ever seen her wear. His stole several looks at her exposed cleavage but forced himself to look away quickly each time so he wouldn’t get caught.
Jim was also worried that his mom would start acting different, and he didn’t know how he would react to that. He calmed down slightly when she greeted him just as she had before. After their hug she asked him a million questions about his trip and his finals. As they walked to get their baggage it was so crowded that Jim followed his parents because there wasn’t enough room to walk three abreast. His gaze was soon drawn to his mom’s ass. Her high heels were sexy as hell by themselves, but the way her hips swayed as she walked was virtually addictive. That, combined with the way the dress fit her perfectly, was almost more than Jim could stand. By the time they reached the luggage claim area Jim’s cock was mostly hard. He tried to calm himself down and wondered if he had become a total pervert for having such a primal reaction to his own mother.
Cindy felt confused about Dan’s reaction, but she convinced herself that Dan was waiting for their date night. She figured this was part of the game and that he didn’t want to get “out of character” until the prearranged time. Cindy couldn’t help but flirt with him anyway. Even if he didn’t respond to her flirtations, it still drove Cindy wild to flirt with him in anticipation of her date night. She hoped to get Dan’s attention enough that they would fuck before their date night, but he wasn’t interested. Every night he said he was too tired and fell asleep on the couch or stayed up well after her “catching up” on his work. Cindy kept telling herself that he was just waiting for their date night and continued to relieve her pent up lust with her trusty toys.
Jim noticed that his mom was acting a little different, and it was driving him wild. He wondered if this was all part of her new look and attitude or if she was intentionally trying to drive him wild. He took much vicarious joy in admiring her sexy new wardrobe. She was also flirting much more openly with his dad than she had ever done before. He enjoyed watching her flirt and play sexy little teasing games, but he desperately wished she was doing it with him. He told himself that she must be doing it because she couldn’t flirt directly with him. After all, she couldn’t really flirt with him openly when his dad was around, so he figured she must be putting on a show for him by teasing his dad.
Ever since he had arrived home he had jerked off at least every, and most days he jerked off several times. It seemed that he nearly had the best of everything now. For any observers, nothing had changed with his relationship with his mom. They hung out and did all the same stuff they had done before, but now there was an exciting undertone to every day with her. Jim was constantly horny for her and the fact that his lust was so completely forbidden only made it more exciting. He was amazed at how cool and collected his mom was when they were together. How could the woman who had sent those amazingly hot photos and that series of lusty emails remain so unaffected now? This only made Jim more horny because he figured if she was disciplined enough to control her emotions and hide her amazingly nasty and teasing side that she must be an absolute animal in bed. During his jerk off sessions he created a vibrant fantasy of how it would feel to fuck her. Some of his imagined fucks were slow and tender and others were fast and hard, but in all his fantasies his mom was the perfect mix of knowing teacher and wanton slut.
At times Jim still felt confused and conflicted about what was going on. When he thought about it from a certain perspective, he felt crazy and stupid and perverted for having these feelings. After all, he was now jerking off solely to visions of his own mother. The fact that she was totally hot and had been acting more and more flirtatious when his dad was around shouldn’t matter. He occasionally thought that he shouldn’t be having these feelings.
However crazy it seemed, he reminded himself that she was the one who had started this whole thing. She had sent him the photos. She was the one who had sent him all those sexy emails. She was the one who had set up their date for the explicit purpose of acting out their emails. If she didn’t intend for this happen he couldn’t imagine another scenario that made sense, and he had spent hours and hours back in his dorm trying to come up with some. The only thing he could think that made sense was that his mom wanted to fuck him and had seduced him with her photos and emails. The longer he was home the less he felt weird about the situation and the more he looked forward to their date. There was no doubt now that he lusted her more than he had ever lusted for anyone in his life. Mom or not, he couldn’t wait to fuck her.
Jim had enjoyed his visit so far, but everything paled in comparison to the event he waited for and wanted so desperately. The days seemingly dragged by as he waited anxiously for their date. He was sure that he had never looked forward to anything so much in his life. Finally, the big day was set to arrive. Jim could barely contain his excitement as he got ready for bed the night before their “date”, and he hardly slept that night as his mind filled with unbelievable images of what might happen the next day.
Jim was a nervous wreck the next morning. As she had been the whole time, his mom remained cool and calm around him. He marveled at how disciplined she was and wondered if this demonstration was all part of her “lesson plan” for him later that night. He willed the clock to move faster, but every minute of the day felt like an hour as he looked forward to their date.
Cindy may have looked cool and calm around Jim, but the reality was that she was a nervous wreck. It was almost hard for her to be around Dan. She was so horny and she so looked forward to being with him later that it was all she could do to not simply jump on him and fuck him silly. Through it all Dan still seemed distant and not entirely interested in her. She couldn’t believe he was able to keep up his disinterested act for so long. His emails had clearly demonstrated he was very interested, and Cindy couldn’t wait to feel just how interested.
About an hour before Cindy planned to leave and go to the designated hotel to get ready for the night, Dan collected his things and announced he was going out with the guys. He said they had scored tickets for the hockey game downtown and would probably go out and catch a few beers afterward, so he wouldn’t be home until very late or he might crash on his friend’s couch.
Cindy was initially very upset and confused because his story seemed so real. How could he forget their date? How could he blow her off? She finally calmed down and convinced herself that Dan’s announcement was just a cleverly crafted cover story. When she thought about it, it was perfect. He had given Jim a perfectly plausible reason for staying out very, very late or not even coming home at all. Cindy scolded herself for being so nervous and felt a renewed wave of excitement and anticipation for their date.
Cindy gathered up her things and packed them into a large purse that, for tonight, would double as her overnight bag. She left a little while later telling Jim that she was going out with some of her friends from the gym. Her story wasn’t nearly as polished as Dan’s had been, but she told Jim that she might be out really late. If things got to be too late, she might just spend the night at one of her friend’s houses so she wouldn’t have to drive home when she was tired. By the time she got into the car she could already feel the heavy wetness in her pussy.
For several minutes Jim sat in silence as he tried to figure out what to do. Deep down, he knew that he had already made up his mind. He wanted to go, he couldn’t wait to go, and he was more excited about going than he had been about anything in his life. However, part of his mind continued to question what he was doing. How could he want her so badly? This all seemed so crazy, but he again reminded himself that she had started all this. He took a deep breath and told himself that she must want this as much as him.
He got up and went to his room. He looked through his closet and selected one of his nicest shirts, ties, and pants to wear. He took a long shower and shaved before getting dressed. The whole time his mind was a blur of anticipation and excitement. Finally, he got into his car and drove to the hotel his mom had identified.
The hotel was very nice. It wasn’t the nicest place in town, but it was probably in the top five. He parked and swallowed hard to try and calm the pounding in his chest. He double checked the room number on the slip of paper in his pocket and headed for the elevator. He went up to the fourth floor and quickly found the designated room number. He stared at the door for a few long moments before gathering the courage to knock.
After he did finally knock on the door he heard some movement inside and then the door opened. The lighting inside the room was dim and she must have been standing behind the door because all he could see was the bed and a small sofa against the wall. Without a word he stepped inside. The door closed behind him and then he heard a gasp.
“Jim!?!” Cindy gasped, “What the hell are you doing here?” As she talked she attempted to cover herself with her hands. Jim glanced down and tried to keep himself from staring obviously. She was wearing only a very sexy, very revealing camisole and high heeled shoes. She was definitely expecting someone to sweep her off her feet, but it was obvious by her shocked reaction that she wasn’t expecting Jim.
Jim suddenly felt embarrassed and stupid. How could he have thought she wanted to fuck him? But if she didn’t, how could she explain what she had done?
Cindy disappeared into the bathroom and came back out wearing one of the thick, white robes from the bathroom. Jim stood dumbstruck in the middle of the room. He didn’t know what to do, say, or think. He just stared at her when she came out of the bathroom. He couldn’t tell if her expression was more angry or confused. “What the hell is going on?” she asked again. “Why are you here?”
“I, I…” Jim stammered, “I was just following your instructions.”
“My instructions?” Cindy asked indignantly. “I think you’d better explain yourself.”
Jim took a deep breath and started from the beginning. He told her about receiving the photos in her letter and how they made him feel. He described sending the emails and how much he came to realize that he wanted her.
Cindy looked completely shocked and for a long time didn’t say a word. Then Jim could see her eyes well up with tears. Cindy burst out crying as the realization of what had happened hit her fully. She began talking, spilling all of her deep secrets about what had been going on with her and Dan. She said the photos were supposed to go to Dan. She said that the whole time she thought she had been trading those emails with Dan. She said she had no idea it was actually Jim. She cried harder and continued talking about how lonely she was and how this was just the perfect ending to her latest attempt to fix things. She told Jim all about how she and Dan had drifted apart, about how he showed no interest in her anymore, and about how she had tried this latest attempt to rekindle his interest.
As they talked Cindy steadily drank champagne. There were three bottles of expensive champagne lined up on the dresser and it was clear that she had been expecting a long and wild night. Part of the first bottle was already gone when Jim arrived and she soon finished that bottle and started the second one. By the time she finished telling her story she was still crying. She took a big drink of her champagne and finished what she had in her glass.
Cindy had never been a heavy drinker. Usually she was good for one or, on a really wild night, two drinks every once in a while, but that was typically it. Jim could tell she was drunk as she sat crying and mumbling to herself about how stupid she was for thinking Dan would still be interested in her. She went on about how he probably had some young, sexy thing at his office and how there was no way he’d be interested in someone as old as her.
Jim couldn’t stand to hear her talk about herself like this. He had already mentioned how her photos and emails made him feel, but he wondered if she had even heard him say it with the shock of what had happened. He told her she was crazy to talk like that but she immediately interrupted and asked who would want to be with someone as old as her.
Jim started talking and before he realized it he told her again all about how the photos made him feel. He told her how he had jerked off to the photos and the emails. He told her how his friend had gone wild over the photos. He said he wanted her more than he had wanted anyone ever before. He said that she was hotter than most of the young girls at the university.
Cindy tried drying her eyes and quickly dismissed what he said. “It’s sweet you are trying to make me feel better,” she said, “but you don’t have to do that.” Jim assured her that he wasn’t just saying this to be nice. He reiterated how hot she was and how much he wanted her, how much he thought about her, and how many times he had jerked off thinking about her.
As he said all this he mostly looked at the ground in front of him. He was afraid to look at her because he felt embarrassed and couldn’t believe he was saying all this to his mom. Finally, as he finished telling her how he had regularly thought about being with her, he glanced up at her. He found she was looking directly back at him. Their gazes locked and for a few seconds neither said anything. Her look surprised him and he couldn’t quite place the emotions he could see burning behind her eyes.
“Is that true?” she asked softly. Her speech was slurred and the glazed over look in her eyes showed how drunk she was.
“Yes,” he said without breaking their eye contact. “I want you.”
Jim wasn’t sure if he moved toward her or she moved toward him, but in the next moment they moved together and met in a deep kiss. This was a lustful, wanton kiss of desperate lovers and nothing like they had shared before. Their arms wrapped around each other and their tongues met and danced wildly. Jim’s mind raced with the realization of what was happening, but soon his mind went blank and he became utterly absorbed in the moment. From that moment on nothing else in the world mattered. He no longer cared if this was right or if they should be doing this or what any of this meant. All he knew was that the woman he had desperately lusted after for the past several weeks was now wrapped in his arms as they shared a deep, wanton kiss.
The kiss lasted only a short while longer before Jim’s lust overcame him. He pulled away from their kiss and began kissing and licking his way down her cheek. He continued down her neck as she moaned wantonly and tilted her head back to allow him easier access. His spine tingled as he briefly realized he was living out a scene that he had fantasized countless times.
Her skin felt and tasted amazing, better than he had imagined. As he reached the base of her neck he caught a whiff of her intoxicating perfume. He never remembered her wearing perfume before and the sweet, sexy scent sent chills down his back. He kissed and licked along her collarbone for a few moments before she pulled away and stood up. For a moment Jim was gripped with the fear that she was stopping him and what was happening. Instead, however, she turned to face him and reached for the knot holding her robe closed. She untied the knot and slowly let the robe drop off her shoulders and onto the floor. Jim no longer hid his hungry gaze as he drank in the sight of her in the sexy lingerie. He stared at her tits and savored the sight of her cleavage being amply displayed by the deep neckline of the camisole. He looked down her body and marveled at her strong and shapely legs. Finally, his gaze stopped at her feet and the sexy red color on her perfectly manicured toenails. When he looked back up to her face he saw that her expression had become a mask of pure, wanton lust. It was almost as if she hadn’t really believed he was telling the truth about his desire for her until she saw it in his eyes as he gazed upon her body.
She moved to him with a desperate intensity and glided onto his lap with her legs straddling his thighs. They resumed their hungry, wanton kiss for short while longer before she parted it. She leaned back and brought her hands to the knot of his tie. Her hands moved a little clumsily from her drunkenness, but soon enough she had it untied. She yanked it off his neck and threw it aside. She brought her hands to his shirt and grasped it on either side of the buttons. With a hard yank she ripped his shirt open and sent several buttons flying across the room. She pulled and tugged a few more times until all the buttons ripped open and then she yanked the shirt tail out of his pants. She pushed the shirt down his arms and flung it across the room.
Jim had never seen anyone act with such obvious lust and purely wanton desire before and he couldn’t believe how excited he felt. After removing his shirt, she stood up and immediately reached for his pants. She roughly and urgently opened his belt and yanked open his pants. Jim lifted his hips off the bed as she pulled his pants down his legs. She tugged his pants and boxers off at the same time and threw them onto the floor. Jim gazed at her in amazement and wonder at what she would do next.
He groaned loudly as she dropped to her knees in front of him. Without a moment’s hesitation she grasped the base of his rock hard cock. Jim’s groan intensified as she hungrily engulfed him. She bathed him with her tongue and warm saliva as she wantonly licked his cock. Jim had received several blowjobs before, but never had anyone so confidently and wantonly licked him. After a few more delicious moments she wrapped her lips around his shaft and bobbed her head up and down in a magical tempo. How the fuck could it feel this good? Jim wondered to himself. It was like she knew exactly what he wanted. She continued to tease his cock with her lips and tongue and time completely blurred. Jim didn’t know if it was minutes or seconds later, but soon his lust and desire completely overcame him. He moaned loudly and bucked his hips as he felt his cum begin to erupt. He managed to gasp, “I’m cumming!” only seconds before his cock erupted in a volcano of pent up lust. Cindy released his cock from her mouth and stroked his wet shaft expertly. The first heavy, thick jet of Jim’s cum landed on her cheek. The rest of his load sprayed all over her face, hair, arm, and hand as she easily and expertly coaxed the biggest load of cum and the most powerful orgasm Jim had ever experienced.
When he finished cumming Cindy brought her mouth back to his cock. Before his cock could even begin to grow soft she began sucking and coaxing him back to the fully excited state. Jim gazed wildly at the vision of her, still covered with his cum, as she devoured him. A couple of times she dropped her head all the way down on his shaft. She didn’t quite take his full length down her throat but it was closer than anyone had ever come before. Each time she gagged a little just before the last little bit could slide down her throat, but her enthusiasm didn’t diminish as she continued sucking him and trying to work his full length inside her mouth.
Sooner than Jim realized possible he was ready for more. She sucked him for a little while longer before she finally let him pop out of her mouth. She stood up before him and gazed down at him lustily. She grasped her camisole and lifted it up over her head. Jim gazed wildly at the sight of her naked body in front of him. He only got a quick glance before she moved toward him and pushed him down onto his back. She gripped his cock and guided her pussy down over him. Jim felt the heat seemingly radiating from her pussy, and he was sure he had never felt a pussy so wet and excited as hers. His full length easily slipped inside her as she dropped down over him. She paused for a moment with her full weight on him and his full length buried inside her.
Jim loved fucking like this with the woman on top, but he wasn’t in the mood for that now. What he wanted now was to control the fuck instead of letting her control the moment. He sat up and, in the same motion, gathered her up in his arms. He spun them around without his cock ever leaving the heavenly confines of her pussy and settled them down in the missionary position. She groaned deeply as he moved them and then cried out loudly as he started pumping his hard cock back and forth inside her. The sensations were already amazing and, in only these few short seconds, surpassed anything he had felt while fucking before. Not only was her pussy hotter and wetter than anything he had ever experienced, but it somehow seemed like their cock and pussy were meant to be together. Jim couldn’t even begin to explain it but somehow his cock just fit inside her as if it was designed solely for that. The sensations surpassed anything Jim imagined possible.
The harder and deeper he fucked her, the more enthusiastic her reaction became. She cried out passionately and loudly urged him to fuck her harder and faster. Jim willingly obliged and soon the bed rocked wildly under the force of their fuck. After only a few minutes of this intense, wild fuck, Cindy literally screamed with pleasure as her pussy exploded into orgasm around his cock. She clutched at Jim’s shoulders and back and her entire body shook as her orgasm washed over her in long, deep waves.
Her orgasm lasted for an amazingly long time and Jim continued fucking her throughout. When her orgasm had completely passed Jim slowed his fucking a little to try and remain in control. Seeing and feeling her cum so forcefully almost triggered his own orgasm and he struggled to resist the temptation to cum so he could prolong this amazing fuck.
Even after slowing down Jim only lasted a short while longer before he couldn’t resist his own lust. For a moment he regained his control but then the fleeting thought passed through his mind that he was about to fill his own mother’s pussy with his cum. The idea was so wild and nasty that he felt his cum immediately surge and with a series of grunts he came deep inside her already drenched pussy. He continued thrusting all through his orgasm and was surprised by the force of his orgasm and the amount of cum he shot inside her.
When he finished cumming he melted into her arms as they shared a slow, passionate kiss. They kissed for many long minutes with Jim’s cock still happily inside her wet, warm pussy. He was very content in her arms and locked in this kiss, but the temptation of her naked body was too much to resist. He parted their kiss and slowly kissed his way down her neck. He continued kissing and licking his way down her chest until his lips and tongue danced across her stiff nipples. She moaned contentedly as Jim caressed her tits and savored the sensations of her soft flesh and stiff nipples in his mouth.
Jim lingered at her tits for many long minutes before moving downward and kissing his way down her surprisingly toned and fit stomach. When his mouth reached her pussy she let out a long, deep moan. In just a few seconds his whole face was coated in her heavy juices as he slowly and teasingly licked and teased her pussy. He dipped his tongue deeply inside her and tasted the culmination of their fuck. Cindy moaned loudly and her reaction only intensified his attention to her pussy. He slowly and deliberately tongue fucked her as she moaned deeply. He continued for a few more minutes before she reached down and grabbed the back of his head. She pulled his face against her as she bucked her hips and orgasmed with a long, deep moan.
The feeling of her cumming was so amazing that he didn’t want this to end. He continued tongue fucking her after she finished cumming for many more long minutes until his tongue ached. Finally, he shifted his position and started teasing her excited clit. Jim took his time and slowly teased her clit for a long time. His tongue and lips danced over her clit and the folds of her pussy as he savored her taste and tried to memorize every aspect of her pussy.
The entire time Jim lingered at her pussy she reacted strongly to his every movement and touch. Her moans and happy sighs only added to his pleasure. Finally, after spending what felt like an hour teasing her pussy, she again grasped the back of his head and pulled his face against her pussy as she burst into another orgasm. Jim savored the sensation of her pussy dancing and twitching under his tongue and mouth. As her orgasmed peaked Jim slipped his tongue back inside her pussy so he could fully experience her quivering pussy.
He lingered at her pussy for several long, delicious moments after she came. He drank in her heavy wetness and her strong taste. Finally, he left her pussy and slowly crawled beside her. She rolled him over onto his back and met him in a deep, hungry kiss. Her tongue explored deep into his mouth and their tongues danced wildly. They remained like this for many minutes until finally Cindy parted the kiss and lifted herself off him. She leaned over him and, smiling wickedly, let her heavy tits drag across his chest and up to his face. She dragged them back and forth across his mouth as he hungrily licked and sucked her nipples and tits.
Jim thought this would lead to another fuck, but instead she teased him for a few more moments with her tits before she settled down again beside him. They kissed softly and slowly and, after the intense release of the wild anticipation that had led up to this night, Jim realized how tired he was. A wave of intense fatigue washed over him as he settled contentedly in her arms. Just before he drifted off to sleep he was aware that she was tenderly caressing his soft, sticky cock. He couldn’t imagine a better way to end the day and drifted off to sleep.