Moving Forward

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Moving Forward
Moving Forward

Ever since his wife of 28 years tragically passed away a year and a half ago thanks to an intoxicated driver, Tim Mackie had strived to enjoy every minute of the life he has left to the fullest. At 53, he had decided to not wait around for life to just happen to him anymore. Her passing had been tough on him and their 3 grown c***dren. They had just married off their youngest daughter and were in the midst of settling in to the new realities of being empty nesters for the first time since being first married.

His wife Rachelle was a 5’8” blond former athlete like Tim. They had had a decent sex life for the most part. But life kind of gets in the way when you are raising three k**s and balancing work and school activities. A few pounds here and a few pounds there, and suddenly the spark had fizzled a bit. She had a great set of D cups and a nice full booty and despite having gained a few pounds, was still a fairly fit woman who could easily dress sexy if she wanted to. Tim had always had a strong sex drive, much, much stronger than hers. Unfortunately, like a lot of women of her generation, she was fairly conservative with sex. She could take it or leave it. Tim on the other hand, wanted it all the time and was always trying to push her boundaries. No matter what he tried or suggested, there would be no “crazy stuff” with her as she used to say. She was probably not that different than most women, but it always left Tim frustrated. In all fairness, he had also come to the conclusion that he wasn’t exactly the slim, sexy guy she married either. He had really let himself go over the years. Finally in 2017, Tim decided for good to do something about his body and his health.

He lost a whopping 105 lbs during the course of 2017. After years of all talk and no action, he had finally decided that he was sick and tired of being sick and tired and got serious about his health. Through primarily diet and exercise, Tim steadily lost the pounds. He started on January 1, weighing 305 lbs. Even though standing at an above average height of 6’2”, that was a lot of weight. By the beginning of the summer, he was down to around 255. In mid August, he was walking his youngest daughter down the aisle at a respectable 230 lbs. By his 52nd birthday in early November, he was at 210. Thanksgiving saw Tim at 205 and in early December, he hit his goal of 200 lbs. Talk about empowering! For the first time, he had gained control of his health and wellness and it felt immensely satisfying.
Not to be outdone, Rachelle had also lost 25 lbs to a weight of 140 lbs thanks to diet and lots of yoga, strength training and cardio. Back was the smoking hot wife he remembered from their early years and Tim found himself turned on nonstop by her presence. For her part, her libido had returned as well and they once again enjoyed a vigorous and passionate sex life.

As a follow up to having achieved his weight loss goals, Tim had decided to take up bodybuilding. Rachelle wondered if he was being a bit too ambitious at 52. Tim was no stranger to weight lifting as he was a 3 sport athlete in high school and had learned how to properly lift weights years ago. He had done his homework and thanks to a lack of any nagging health problems, Tim was cleared by his doctor to take the leap.

Sadly, only a week into his new regimen on a Friday afternoon in mid December, Rachelle was killed when a delivery van driver high on meth plowed into her car while she was stopped at a red light. The impact was immense as the van was traveling in excess of 45 mph at the point of impact. She never regained consciousness. Tim and the k**s never got to say good bye. His last memory of her was of holding her hand and staring into her swollen and expressionless face as she slipped away, hooked up to all manner of tubes, sensors and machines. It was utterly devastating and nothing could have prepared him for it. Thankfully, they were fully insured and Tim was able to resume his life without the added headaches of financial difficulty. But after a whirlwind week of family, friends, funeral arrangements, güvenilir canlı bahis siteleri the upcoming holidays and time off from work to sort things out, Tim was finally left with an empty house and no clue how he was going to continue onward.

As a way to occupy his mind when he wasn’t pouring himself into his work as a management consultant, he plowed away at training, watching his macros, taking supplements and eating 4,000 calories a day. He became obsessed with giving every ounce of effort he had in the gym during his workouts and in the kitchen when he wasn’t giving it at the office. It kept him focused and able to deal with this new and totally foreign reality during the hardest period he had ever experienced in his life. Gradually, as the months went by, he began to feel normal again. His motivation had never been stronger.

As a result of the training, he was beginning to get pretty damn buff in the process and it startled even him at times. Throughout 2018 and well into 2019, Tim progressed from 200 lbs to 217 lbs, then on to another bulking cycle to 237 lbs before switching to a cutting regimen that saw him trim down to a thoroughly ripped 225 lbs. Tim’s body fat was now sitting at around 10%. He had that classic beach body look. Big shoulders, arms and pecs. A washboard stomach, powerful neck and back muscles and big, muscular glutes, hamstrings, quads and calves. He would catch himself staring in the mirror often. He even keeps a photo of his former self on the mirror as a reminder of what he looked like back in January 2017 and how far he has come. It seems a lifetime ago.

Tim had discovered that his libido had not only never gone away, but it was stronger than ever thanks to the added muscle mass and accompanying testosterone levels coursing through his veins. It seemed that his hefty 8” cock was always hard and in perpetual need of relief. Being so close to Rachelle’s passing, Tim struggled mightily with the desire to pursue women without feeling like he was cheating on her. Then, one day he was surfing the porn sites and began to view crossdressers and trans girls in action. Tim was shocked at how sexy some of these people looked in the videos. Some were almost completely indistinguishable from women with the exception of their little cocklets and it intrigued him.

After some thought, he decided to open some accounts on some of the dating websites. He even mustered up the courage to indicate that he was interested in crossdressers, t-gurls and sissies. His profile was itself, no less stunning. As part of his embracing of the whole bodybuilding persona, Tim had decided early on to tan and shave his body. The resulting pics on his profile immediately got the attention of many people. They included women and gay and bisexual men. Many of the women were stunning, but his heart really wasn’t in it at this point. And the gay and bisexual guys really didn’t appeal to him either. He just doesn’t experience any attraction to masculine guys. But the sissies, crossdressers and the trans girls really interested him for some strange reason.

Finally, one Saturday night, Tim decided to meet up at the apartment of a sissy named Cheri with whom he had been chatting for the past week. Cheri was 21, around 5’6” and not even 140 lbs. As she opened the door, Tim was stunned. She was wearing a beige, shear cover over her shoulders. It barely concealed the killer lingerie bikini top and thong with white stockings and heels under it. Her long, raven black hair was perfect and all natural. Her face, makeup, and jewelry impeccable. Tim had been preparing himself to be realistic with his expectations, but damn! He did not expect Cheri to look even better in person than her profile pics.

“Hi Tim. Do you want to come in?”

Tim realized that he had been staring and quickly snapped out of his Walter Mitty moment.

“Oh. Yeah. Sure.”

Tim found himself clearly embarrassed and nervously chuckled to himself. She ushered him in and they engaged in some small talk. Tim was clearly nervous as hell and Cheri was quick to pick up on it and do her tipobet giriş best to make him feel at ease.

“Wow. You are looking killer tonight. I hope you like my lingerie. I bought these just for you tonight.”

Her soft feminine voice really struck him. If he didn’t already known Cheri was originally physically male, he would never have suspected. Cheri began to model her lingerie by spinning around in various suggestive and playful poses, trying to lighten the mood. Tim was mesmerized and his cock was taking notice as well. Cheri immediately saw his tenting pants and dropped to her knees, offering to help him out of them.

“Can I take care of this for you daddy?”

Without really even thinking about it, Tim watched Cheri pull off his pants and begin to feel his growing cock through his briefs. Tim was in another world. Finally, Cheri began to kiss and nibble at the outline of his now fully erect tool. It felt incredible and Tim wondered how long he was going to be able to last before shooting his load.

“Damn, baby. That feels incredible.”

He hadn’t jacked off in 3 days in preparation for this meeting. Cheri decided to up the intensity level and grasped the waistband of Tim’s briefs, gently pulling them down. Tim’s hefty 8” cock sprang into view and Cheri smiled broadly.

“Oh wow, daddy. I didn’t realize you were this big. Such a beautiful cock.”

Looking up at Tim, she very sensually licked the tip of his cock, capturing the drop of precum that had formed. Tim gasped and shuddered as Cheri began to lick his shaft. Rachelle had been a good cocksucker, but she never really took the time to enjoy blowing Tim. Cheri was at a whole other level and Tim was struggling to maintain his composure. When Cheri took almost all of his girthy meat into her mouth and throat, Tim gasped and moaned loudly at the exquisite sensation.

“Oh shit, baby. Keep swallowing daddy’s big dick.”

Tim couldn’t believe he was talking like this. His precum was really flowing and Cheri hummed and moaned her satisfaction of enjoying his sweet nectar. She began to take more and more of his shaft, expertly deepthroating him until only an inch remained. After stroking him like that for a minute or two, Tim had to force her to stop. He didn’t want to cum just yet.

“I’m sorry baby, but you gotta stop before I cum too soon, I’m getting so close now.”

On cue, Cheri rose up to her feet and, taking Tim by the cock, led him to the bedroom. By this time, Tim was in full aggression mode. Months of pent up sexual tension was finally boiling over. He forced Cheri down onto the bed on her stomach and began groping, kissing and aggressively caressing her backside. Her gorgeous ass exposed to him in all it’s feminine, shapely glory. Without even thinking about it, Tim dove into that booty, kissing and tonguing the silky smooth flesh. He had rimmed Rachelle a few times, but she was never comfortable with it. In fact, it made her tense up until she finally had to make him stop. Cheri, on the other hand, was moaning like a bitch in heat and it spurred Tim on even more.

“Oh shit, daddy! Your tongue feels so damn good in my pussy. Ummm. Oooohhh. Don’t stop. Ummmm!”

Her tasty rosebud was as fresh and clean as he could ever hope for and he repeatedly stabbed his tongue deeper and deeper into her quivering backside. Cheri was moaning and urging him on, her breaths coming in shallow gasps and moans. Eventually, she was begging Tim to take her ass.

“Please fuck me daddy! Please fuck me daddy! Please fuck me now!”

Tim finally decided it was time to scratch the itch. He got up on his knees and after applying a generous portion of lube, guided his meat into the entrance of Cheri’s hole. They had agreed earlier to forgo condoms and Tim’s nervousness about it was now easily eclipsed by the massive arousal he was experiencing. As he began to push in, Cheri’s breath caught in her throat and she asked him to go slow.

“Shit that cock is so fucking big, daddy! Please don’t hurt my pussy. I need to adjust.”

Tim’s girthy meat was stretching her hole greatly. Tim was almost overwhelmed by the tightness tipobet güvenilir mi and warm wetness of Cheri’s hole gripping his cock. He slowly began to rock back and forth, inching his cock further and further into Cheri’s immaculate asshole. Eventually, he bottomed out in Cheri as he felt his smooth balls up against her ass cheeks. Tim began to saw away at that ass as Cheri’s moans continued to build.

“Uh, Uh, Uh. Oh, Oh, Fu! Uck! Me ee.”

In no time, the slapping of their skin together from his pounding filled the room and his breaths were coming in gasps. He knew that he was fast reaching the point of no return. Under him, Cheri was nearly sobbing into the pillow.

“Pl-eese, da-dd-ee. Pl-ee-ee-se cum-mmm in-nn mm-my pu-ssy-yy!”

Cheri was begging for his seed, her voice ragged and almost incomprehensible. Finally, with a roar and a series of violent jerks and grunts, Tim released a massive load in Cheri’s bowels. No less than 8 ropes filled her ass pussy and Cheri could feel every twitch, every contraction of Tim’s throbbing meat. The sensations threw Cheri over the edge and her little cock squirted all over the bed under her.

Tim collapsed on top of Cheri, catching his breath.

“Fuck, baby. That was incredible.”

Cheri was exhausted and felt truly full and satisfied with him inside her. Almost reflexively, he affectionately nuzzled and kissed the back of her neck.

“That was one incredible fuck, baby. You are such a truly nasty little slut,” he gasped, trying to regain his breath.
That elicited a chuckle from both of them. Where is this language coming from? He had never spoken like this with Rachelle. Finally, he eased himself off Cheri, retracting his dripping cock. Her gaping and leaking hole clearly visible to him as he inspected his work.

“Wow baby. That hole is so fucking open right now.”

Despite his utter satisfaction, Tim immediately began to feel awkward. He couldn’t really put a finger on the feeling, but it was hitting him in full force. He hastily began to get dressed.

“Is everything ok?” Cheri asked.

She was confused by his lack of expression, silence and resolute focus on putting his clothes back on.

“I’m ok. It just brought back some memories for me. Don’t worry about it,” he said before leaving Cheri’s place in a hell of a hurry.

He hadn’t anticipated this. Memories of making love to Rachelle he thought he’d forgotten had come rushing back like waves. He felt as if they were engulfing him. And in his moment of panic, his only impulse at the time was to get out of that apartment as quickly as possible. The drive home was only 20 minutes, but it felt like 2 hours. Those memories and emotions were hitting his mind like pounding surf on a crumbling sea wall. For the first time, he realized that he hadn’t really mourned Rachelle since she died. He hadn’t been able to let her go in his mind and heart. He pulled off the side of the road and openly wept for the first time. Epic, deep, uncontrolled, shaking sobs took hold of him to his very core. After several minutes, the sobs began to subside and his mind began to clear of the intense emotions. The rest of the ride home was uneventful and cathartic. Back at home and feeling utterly exhausted, he immediately went to bed and was out nearly as soon as his head hit the pillow. For the first time since Rachelle’s death, he slept fully, deeply and peacefully.

Early the next week, he texted Cheri and apologized for his hasty exit. It had been quite a lot to process and he needed time to sort through his thoughts and emotions.

“It’s not your fault, Cheri. This was the first time I had had sex with anyone since she passed. I thought it wouldn’t bother me, but I guess it did a bit. I’m sorry I bailed on you like that.”

“You don’t have to apologize, Tim. I had a great time and when you feel up to it, I’d love to do this again.”

Cheri understood and thanked him for a great time. She could only hope they would get together again. Tim felt like an ass for bailing on her like that, but deep down, he knew he’d probably be back. That was just about the best fuck he had ever had and he would have to have Cheri again.

But more importantly, he had been able to let Rachelle go and give himself permission to move forward and have new experiences. For the first time, he truly felt empowered to explore this very private and personal dimension of his new life and it was exhilarating.

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