Melissa's Journey: A Big First Step

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MILF's journey of self-discovery takes a huge step.
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Melissa, known to her friends as Mel, had just turned 43 although she looked younger, and her body, with her shapely 36C breasts, still turned heads. Her oldest son would soon leave for college, and since turning 40, she had been taking stock of her life experiences and thinking about the next phase. Her thoughts often centered on erotic experiences, interests, and fantasies, which made sense. Mel had always been sexually curious and uninhibited, and she would even admit to having been somewhat promiscuous into her early 20s. With a few exceptions, though, she had largely suppressed that part of her personality while raising her two sons and establishing a professional reputation.

Over the years, Mel's husband had always encouraged her sexual exploration, and he was behind their most indulgent experiences. As an example, Mel had a definite exhibitionist streak, and her husband encouraged her vice by buying her provocative clothes, playing the "clueless husband" as Mel exposed herself to strangers, and arranging vacations where they visited topless and nude beaches. And, about twelve years earlier, her husband shared a fantasy of Mel having sex with another man and assured her she had a "hall pass" if she wanted one. At the time, though, building a career while mothering two young, rambunctious boys, Mel did not feel especially sexy. So, the idea was relegated to an occasional role play, but her husband's assurances that she was still sexy and that any normal guy would kill to sleep with her (or to "fuck you" as he usually put it) were good for her sexual confidence. More recently, she sometimes felt regret for not having taken her husband up on his offer to play around way back when.

Mel wasn't dissatisfied with her life, and she did not feel she was having a "mid-life crisis;" her journey was more about reflecting on who she was at a deeper, more intimate level, with some "road not taken" scenarios sprinkled in. When Mel was about to turn 42, something sent her thinking into overdrive and had a similar impact on her libido. She couldn't shake the sense of "now or never" that permeated her erotic thoughts. Her fantasies become more frequent and more risqué, and she struggled to reconcile some of her sexual thoughts with the reality of being a suburban "soccer mom" (actually more football and baseball) with a successful career and a long-term marriage.

Mel was captivated by the thought that having a wonderful family, good friends, and doing meaningful work was not inconsistent with honoring the sexual curiosity, excitement, and lack of inhibition she felt as a young woman. As part of her internal debate, Mel admitted she had always enjoyed sexual attention, and now in her 40s she was increasingly aware of being "checked out" by friends, co-workers, strangers, and even by her sons' friends, who were not very discreet when they took peeks at "Mrs. C" as they all called her. It was just such an episode that transformed Mel's journey from fantasy to reality.

The school year had just ended, and Mel agreed that her oldest son, Josh, could invite a group of his guy friends and teammates over for a cookout and pool party. As always, Mel was the "cool parent," preparing great snacks and food, and putting up with the boys' loud music and high school shenanigans. It was a sunny and warm Friday afternoon, and the recent graduates first feasted on homemade nachos, chicken wings, and guacamole that Mel served in a bikini. Over the years, she had learned how to discreetly show off her body, and she enjoyed teasing the boys and seeing them sneak peeks at her breasts as she "innocently" leaned over to refill the snacks or clean up around the pool area. Mel told herself the attention was her payment for the time she spent preparing and serving the food and drinks.

As the boys roughhoused in the pool, Mel laid on a chaise lounge to get some sun. She did give them a little show as she applied the sunscreen, but she kept things under control for her son's sake. She didn't even undo her top when she turned over to get sun on her back, but she did have a fun thought about asking for help putting sunscreen on her back, but again she knew that be awkward for Josh. As she laid there, though, she imagined two or three of the boys--most of whom had grown into attractive young men--lathering up her back, legs, and ass cheeks.

Later, from inside the house, where she was preparing the burgers, hot dogs, and ears of corn for the second course (and sipping on a glass of French rose), Mel watched the eight young jocks in the pool playing some made-up game that looked like a strange combination of water polo, basketball, and wrestling. As far as she could tell, there were two teams, a ball, two goals, a lot of grabbing and dunking, and even more smack talk. Mel was always amazed by how easily boys found ways to entertain themselves with some type of competition.

One of the boys, Aaron, got a call, and Mel watched him climb out of the pool to check his phone. As Mel finished her glass of wine, she found herself admiring Aaron's very toned and muscular body, especially his six-pack abs. She blushed a little, knowing she was looking lasciviously at an 18-year old young man she had known since he was in elementary school. She chalked it up to her new, less inhibited way of thinking... and the wine. Unfortunately, Aaron unexpectedly had to leave to go into work.

When Mel went outside with some paper plates and plastic utensils, several of the boys said they needed her to get in the pool and join the game because the teams were now uneven. She politely declined, saying she had no idea how to play, but they said they would explain it to her and continued to encouraged her to join the game. Even her protestation that the food would be delayed wasn't enough to dissuade the boys from almost insisting she join in so the game could continue. Mel looked at her son who just smiled and shrugged, so she agreed "but just for a little bit because you guys have a lot of food to eat." She could feel several sets of eyes on her as she walked down the three steps into the pool. Before joining the group, she turned away from them and undid, then tightened, the bikini strap behind her neck.

Mel mostly understood the rules and objectives, and the game got back underway. Players were spread around the pool and paired up, one for each team, defending against each other. Taking Aaron's place, Mel was paired up against Matt, a strapping 18-year old who moved into the area just three years before and instantly became a sports star and member of her son's group of friends. He was about 6'2'' tall, weighed about 200 pounds, and in the fall would be attending college on a football scholarship. He was also a good looking guy who Mel understood just broke up with his cute girlfriend.

As the game went on, and Mel's team had control of the ball, Matt defended by grabbing Mel to keep her from getting the ball. And when Mel was on defense, her competitive nature caused her to try to limit Matt's movement, despite his physical advantage. The nature of the game led to lots of grabbing and touching, and Mel became aware of how often Matt's hands "accidentally" ran across her stomach, over her ass, and occasionally even brushed against a breast. At one point, in the guise of playing defense, Matt cupped her ass cheek and held it longer than necessary. When Mel turned toward him, he immediately removed his hand and she saw a little fear in his eyes. But Mel just smiled at Matt and said out loud "no crying when you lose boys." The other guys hooted and hollered, and when one said that "Matt has his hands full" she made eye contact with Matt and smiled.

After that exchange, Matt got more handsy, feeling Mel's rear and copping a few underwater feels of her breasts. Mel's inner soccer mom was struggling with her newfound sexual liberation, and she worried whether Matt was the kind of kid who would "brag" about something like this. She didn't think so, but the concern nagged at her. At one point, Matt had the ball and his teammates were urging him to try to score a goal. In a very athletic move, Mel jumped on Matt's back and knocked the ball out of his hand. Unbeknownst to the other guys, Mel was able to knock the ball loose only because, in addition to her breasts pressing against Matt's back, her left hand had reached around and grabbed Matt's crotch. Matt immediately let go of the ball when Mel squeezed his semi-hard cock.

The others erupted in cheers as the ball floated away and one of Mel's teammates retrieved it and scored for her team. The guys began teasing Matt about getting "schooled by a girl" and "owned by Mrs. C." Matt took the ribbing and shrugged, finally saying, "Dude, Mrs. C is a stud," cracking up the entire crowd with his inapt metaphor. Matt then whispered to Mel: "And she doesn't play fair."

"Oh, did I do something against the rules?" Mel teased.

The game went on for another ten minutes or so during which Matt's hands were almost constantly defending or trying to score. Mel's earlier heroic play gave him an excuse to be even more physical. At one point Mel guarded Matt by standing between him and his teammates. Instead of genuinely trying to separate from her to get the ball, Matt pressed his crotch against Mel's bottom and put his hands on her ribs just under her arms. Mel could feel that Matt had a hardon and she let him push against her. When one of Mel's teammates rushed the goal and scored, she twisted her body so that Matt's hand cupped her left breast for a few seconds. When the hoopla from the goal settled down, Mel announced a time out so that she could "feed all you growing boys."

The guys (other than Matt) agreed that they were hungry and the game would be paused so Mel could grill the burgers and dogs. She again felt lots of eyes on her as she climbed out of the pool with her wet bikini clinging to her and walked across the deck to get a towel. When she used a towel to take some water out of her hair, Mel positioned herself so that the boys had a side view as her raised arms also lifted her breasts. While she didn't look toward the pool, she was certain most of the boys other than her son were taking in the moment. Mel tingled as she imagined the boys getting hard in the pool. As she headed to the house she turned to the boys and said "I'll be right back with the food. Winners eat first though," she teased, again getting hoots from her teammates.

After the boys ate an unimaginable number of hamburgers and hot dogs, the party started to wind down. Not only were a few boys experiencing food comas, they all got texts about a pool party that night at a girl's house, which made the all guys party less interesting. After the group wolfed down a copious amount of dessert on top of the earlier feast, they began to make plans about meeting at the co-ed pool party that began at about 7:00. As it was now closing in on 6:00, the boys got ready to leave. They did volunteer to help clean up, but Mel said that wasn't necessary and added, "What kind of party will it be if all the cute guys are late?"

"You're weird Mom," Josh said. But the other boys clearly liked Mel's comment.

"Of course, you are the cutest of the cute guys, sweetheart," Mel teased, drawing more hoots from the guys and making Josh regret trying to out wisecrack his mom. But Mel gave Josh a big hug, and whispered that she loved him, making all the other guys instantly wish Mel was pressing her boobs against their chest. "Get on your horses, so I can straighten up before my husband gets home tomorrow morning" Mel said, making "shooing away" motions with her hands.

As the boys left, Mel went back in the house and poured another glass of wine before cleaning up while Josh took a shower, even though he was going to another pool party. By the time Josh was ready to leave a few minutes before 7:00, Mel had finished both the clean up and the glass of wine. Josh thanked her genuinely for making the party happen. "And thanks for being a good sport and joining the game. The guys appreciated it."

"So I'm still in the running for the 'Coolest Mom' award?" Mel asked.

"After today, you may have it wrapped up." Josh said appreciatively.

"I'm just happy everyone had fun," Mel said. "Including me." She hugged Josh again and kissed his cheek. A little mortified by the thought of what he didn't know. "Have fun and text if you are going to be late." Josh assured her he would and headed out to drive to the party.

Mel poured a third glass of wine and took it into her bedroom and the adjoining master bath. She took off her still slightly damp bikini, assessed how much sun she got that day, and then stepped into the shower. Running her soapy hands over her body under the warm water, Mel thought about the boys straining to sneak peeks of her cleavage and boobs. Her mind naturally drifted to how Matt touched her, how she allowed it to happen, and how she even grabbed his crotch. She was titillated by her own misbehavior, and she certainly enjoyed the feel of her soapy hands on her body. Since her husband wasn't coming home from his business trip until the morning, Mel decided to have a light supper, enjoy some more wine, and then go to bed early and masturbate with her vibrator before Josh came home.

Mel got out of the shower and toweled and brushed her hair while standing naked in front of the mirror. She stepped into the large master closet to find some clothes, but when she turned on the lights, the fluorescent bulb on her side flickered and went out, leaving her side of the closet dark. She knew she needed a ladder to reach the light and she was not in either the mood or condition to get on a ladder. As she felt around for one of her favorite rompers, the doorbell rang. She had no idea who it was, or if it was just a package delivery, and she regretted having left her phone, with the doorbell cam app, in the kitchen. So Mel grabbed a short silk robe that came to mid-thigh, tied it on, and, after grabbing her wine glass, headed to the front door.

Mel looked out the side panel by the door and was both surprised and a little confused to see Matt standing at the front door. He had changed into a tight tee-shirt that flattered his muscular upper body, shorts, and flip-flops. Mel opened the door and said, "Hi Matt, Josh already left. Were you two going together or something?"

Matt smiled sheepishly, and responded, "No Mrs. C. I was heading to the party and thought you might need some help cleaning up. I felt bad that we all had a great time at the party and then left and stuck you with the cleanup." Mel processed what Matt said, wondering if he was being sincerely thoughtful or had some ulterior motive for his visit. That led to an awkward pause during which Matt noticed Mel's wine glass and quickly scanned the length of her robe.

Now conscious of the wine, and how that must have appeared, Mel recovered and said, "I'm sorry, Matt, come in, and that is very thoughtful but not necessary." She stepped back, set the wine glass down on a credenza in the foyer, and Matt came into the house. "In fact, I'm pretty much done with the cleanup," Mel told him.

"Are you sure Mrs. C?" Matt said awkwardly.

"Yes, I'm sure, sweetie. In fact, I just got out of the shower, and threw this on when the doorbell rang." Mel wasn't sure why she told Matt those details, but it definitely focused his attention on her short robe and made her acutely aware of being nearly naked. Mel was cognizant that she liked both the attention and the feeling.

"Okay," Matt said, unable to shake the mental image of Mel being naked when he rang the doorbell. After savoring that thought, he said, "I just felt bad that we ate all the food, made a mess, and then left without helping out." He looked at Mel with hopeful eyes, trying to show his sincerity. "Are you sure there isn't something I can do?" Mel wondered if that double entendre was intentional.

"Really, Matt, like I said, I finished cleaning up before my shower," Mel assured him. "But thank you again. It was a sweet thought."

Matt gave her another sheepish smile. "Okay." But he stayed put and seemed increasingly nervous, and Mel knew he had something else on his mind. She even had a good idea what it was. For better or worse, she decided to give Matt an opportunity to say what he was thinking.

"Are you okay, Matt?" Mel asked.

He paused, looked around nervously, and stuttered. "Well, Mrs. C.... I guess I also... wanted to come over to tell you... um... I'm...sorry."

Mel's suspicions were confirmed, but she felt bad for Matt and did not want to make him go into details. She looked in his eyes and said, "There is no need to apologize, Matt." Mel saw that her comment surprised him. "I could have stopped you, and I probably should have," Mel said with a smirk, immediately regretting her choice of words.

Matt blushed. "I'm really glad you didn't" he mumbled. Mel smiled at him. "It was the most exciting thing I've ever done," he blurted out. "So I guess I want to say thank you too."

Now Mel was a little flustered. "You're welcome, sweetheart," she said, using the term out of habit. Her thoughts swirled about how to respond further. "Matt, I'm sure you will have a lot more exciting experiences," she said, immediately realizing it was kind of a strange and response. "And I guess I should thank you too," she added.

"What do you mean?" Matt responded, genuinely confused.

Mel smiled and said, "Well, having a cute eighteen year old guy flirt with an old lady like me is a compliment." She gave Matt a seductive look.

"No way, Mrs. C.," Matt exclaimed, "You're the hottest girl I've ever met. Ever." He looked adoringly at her, and she smiled to herself about being described as a "girl." "All the guys think you're hot," Matt added

Now it was M's turn to blush. "Well, thank you, I think. But I'm sure you will meet many amazing women," she said. Mel was a little surprised, though, by how much she enjoyed his affirmation that the other boys found her "hot."

"I hope so. But I don't think anything will ever top today," Matt said sincerely. Mel could tell Matt was struggling to share with her what had to be difficult feelings to express. She did not ever expect an eighteen-year-old to allow himself to be so vulnerable. Matt was visibly anxious about what Mel would say or do next.

"You are very sweet," Mel said, smiling warmly. Then, driven either by a maternal desire to ease Matt's discomfort or by her own sexual curiosity--or maybe both--Mel stepped toward Matt and extended her arms for a hug. He eagerly accepted and pulled Mel tightly against him. Matt sighed audibly, almost purring, unsure whether this was a platonic hug or, as he hoped, something more.

With Mel barefoot, Matt was more than eight inches taller than her, and she was swallowed up by his 200 pound frame. His strong arms pulled Mel's tits against his chest, and she could feel his erection pressed against her lower abdomen. She knew Matt could tell there was no bra or top under the robe, and she was glad he couldn't feel how stiff her nipples were under her thin robe. Mel had to admit that, despite the risqué circumstances, being wrapped in Matt's powerful arms played into several of her fantasies. She decided she would wait for him to end the hug.

"Your hair smells so good," Matt said quietly as his face buried in her damp hair. He was now deep into his crush on Mel.

Still in the embrace, Mel responded, "You are a flirt, aren't you?"

"I can't help it around you," Matt said, squeezing her a little more tightly. "I've thought a hundred times before in my mind about what happened today," Matt confessed. "It was like a dream come true... only better." His hug tightened even more because he wasn't ready for the moment to end.

"Was it like you imagined?" Mel asked provocatively, knowingly pouring gas on the fire.

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