Once Phil had parked his truck he texted, 'I'm here.' Moments later his phone buzzed and 'I'm in 503' popped up on the screen. He replied, 'Be right up!' Fall had turned to winter and getting out of the warm cocoon of his truck he was greeted by a cold, Michigan evening, the daylight almost gone and made darker by an overcast sky. He pulled his coat zipper up against the frigid wind, thinking it wouldn't be long before snow would be covering everything.
He walked through both sets of massive sliding glass doors as they opened at the entrance of the Russian Highlands Hotel and Spa, an upscale resort that he'd never visited but it had great reviews. She had good taste! The lobby was large, spacious and well decorated with pictures of the surrounding area in the 1800's and some contemporary art. Comfortable, overstuffed furniture formed areas for conversation, spread out with a large circle in front of a crackling fire place. The desk clerk smiled when he walked to the desk and said he was checking in. She said "Your wife already has a key" and Phil thanked her for honoring his request that she be given one before he arrived.
He stepped into the elevator, its interior of brushed stainless and textured glass continuing the upscale feel. As it brought him smoothly to the fifth floor, he cupped his hands together and brought them to his mouth, breathing out to warm them. He exited into the hallway, feeling the same 'first time' butterflies as he did at the start of each new relationship. He stopped in front of the door with an oval, cast brass '503' plaque attached to it, took a deep breath and gently knocked. He heard a quiet "Yes?" from the other side. It was Phyllis. "It's Phil." he replied softly and the door slowly opened to reveal a beautiful woman, partially illuminated by the lights in the hall, the room behind her dimly lit with small, battery votive candles spread about.
Phyllis stepped back and welcomed him into the warm room with a big smile and a soft "Hello." Wearing a cropped T-shirt and athletic shorts with flip-flops she looked amazing. He'd never seen her in anything but cold weather dress and this was a very pleasant surprise. While the door was automatically closing behind him, Phil took her into his arms as she wrapped hers around his neck and pressed his lips to hers for their first passionate kiss. He moved his hands to her bare sides and she jumped from his still cold fingers when they touched her skin. He left them there to warm further as they kissed and then moved them up inside her shirt to cup her breasts. He was happy to feel not a bra, but rather her very soft breasts as he squeezed her hardening nipples with his thumbs and index fingers. Phyllis moaned into his lips with the pleasure of being in the arms of a man who wanted her and the realization that she would soon be naked with him.
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Phyllis's life was busy, rewarding and full but sexless, her husband having told her he was 'all done with that' a few years ago. She was far too young to go the rest of her life without ever feeling the physical love of a man again. Despite encouraging him to try medical solutions to his impotence or work out a compromise for his disinterest, her husband, Don, said he was sorry but just wasn't interested in sex anymore.
After their umpteenth argument she asked him what SHE was supposed to do about HIS decision and in frustration he said, "Do what you need to. I don't want to know about it." She still loved Don and they had a lifetime of history, two grown kids and grandchildren but his decision put her in an untenable position and hurt her deeply.
She spent long nights staring at the ceiling, sexually frustrated and wondering what to do. She missed the intimacy of sex with Don and missed being wanted sexually. As sleep eluded her yet again she could think of only three solutions to her problem....
1) Get a divorce and start over with someone else. That wasn't really an option because she still loved her husband and it would bring nothing but stress and discomfort to family gatherings and her family.
2) Suffer in silence. She was already doing that and it wasn't working. Her vibrator treated her well but it wasn't close to the same as feeling a warm, hard man in her.
3) She could have an affair. He did say 'do what you need', didn't he? Hmmmmmmm.......
The last was really the most viable option but where does an older woman look to have an affair? It sounded like a messy way to just get laid. And who is actively LOOKING for someone her age?
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Phil found himself single when he lost his bride to breast cancer three years ago. She was his life and he had been in a dark place for a long time when his kids and friends encouraged him to get back out into the world again. He was sixty six years old and had always kept himself in shape but wasn't interested in starting over with a new permanent relationship. He and his wife had been together and truly happy for forty-four years and he felt he'd never find another like her but enjoyed the company of women too much to be a celibate hermit.
His daughter sent him some web sites to look at so he could get the feel of who was out there in the senior dating world. The first time he clicked on the links she sent he was surprised that there actually WERE senior dating sites. Who knew? He wanted to spend time with women from his generation who were familiar with the same music, the same fads and the same aches and pains. While younger women have those supple bodies, that's where the attraction ended for him.
Phil wasn't surprised that many posts were by widows looking for their next husband and others were looking for a man to support them in a platonic relationship. He wanted neither. He wanted a casual relationship. Someone to go with him to dinner or a ball game or bowling or a hike. Someone to be romantic with, to kiss, to hold and yes, be intimate with if she was looking for that but it had to be non-committal. He knew that the woman and relationship he needed wasn't going to be easy to find.
Rather than sift through the hundreds of existing posts, Phil thought it would be better if he put up one of his own and let them come to him. He could make it clear what he was looking for right from the start. After several edits he was happy with his post and sent out into the world.
"Widower, 66, active, ISO woman, 55+, to enjoy a lunch, a dinner, a hike, a kiss in the dark at the movie or???. Looking for strings free fun, sexy or otherwise, want to keep it simple and casual.... how about you?" He included a recent photo and hit 'send'.
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Once the hotel room door clicked shut behind Phyllis and Phil they continued to throw fuel on their burning connection. Phyllis nearly orgasmed from sexual overload when Phil grabbed her breasts and pulled her nipples. It had been years since her husband had shown any physical interest in her. As they held each other she pressed her body into his, thrilled to feel his hard cock pressing back.
"You don't mind if I take my coat off and stay a while, do you?" he asked, pulling back from her soft, warm lips.
"In a minute..... I'm really enjoying this right now"
Phil smiled and went back to kissing her, massaging her very soft breasts and now very hard nipples.
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On a whim Phyllis hit the internet. She explored dating sites and found there were some specifically for seniors and she wasn't really surprised that the men her age all wanted younger women. One site she came across was called Silver Connections. "Oh my god!" she thought, "could that name be any worse?" She had scrolled through dozens of posts when she came across the post of 'Phil57', a sixty-eight year old man who was actually looking for someone 55+. Wow! Well, SHE was 55+!
He was a good-looking guy and said he was just looking for some 'strings free fun, sexy or otherwise.' It seemed like a lover on the side was the perfect solution but there were so many ways this could go sideways and actually taking the steps to put a plan like this in motion was terrifying. Would her husband really be okay with her taking a lover to end their arguments? Was there a good way to ask, "Honey, since you don't want to have sex with me do you mind if I have sex with another man?" There really wasn't any way to do that because he said he didn't want to know. She had to think this out. How was SHE going to feel after going through with it? Did Don really mean what he said? The risks were great but were the rewards? Well, she would have to take some risks to find out. Start out small...
A couple weeks later Phyllis and Don were lying in bed, his back to her. They talked in the darkness the way long married couples do. She scooted over and spooned him, putting her hand on his hip and kissed him on the shoulder. They shared the gossip they'd heard and laughed together quietly. She felt very close to him at these times, reminding her of their younger days. She gently rubbed his hip and slipped her hand under the band of his underwear to feel his skin. He didn't react so she slid her hand further over his side, feeling the beginnings of his pubic hair and gently ran her fingers through it. Since there was still no reaction she moved her hand further and grasped the base of his soft dick with her index finger and thumb and his balls with the rest of her fingers, giving them an easy massage. Just when she thought that maybe something would happen tonight he reached down and pulled her hand from his underwear and placed it back on his hip.
She was hurt and angry but remained silent. To Phyllis that was as good as hearing him say, "Leave me alone and go find a man to have sex with." The next morning she clicked on the link she saved and sent an email to Phil57 using her nickname, TeachersPet. She wrote that she was interested in 'strings free fun, sexy or otherwise' and wanted to see if they were looking for the same thing.
When Phil logged into his account on Silver Connections for the first time two years ago he was pleasantly surprised by the responses he got. Some were from the same women whose profiles he'd seen while searching the site but felt they were looking for something he wasn't willing or able to offer. However, there were a few that were intriguing so he picked the one he liked best and sent her an email to introduce himself and give his phone number so she could call when she was ready. If she called, Phil would share a bit about himself to see if there was a connection and he was always open about his condition that their relationship was not exclusive, making sure she understood that he was looking for a relationship that was fun, not serious.
If the call went well he would offer to meet her for coffee so they could get to know each other a little more and then, if she wished to carry on, maybe get together for dinner at a later date. It was always up to her.... how fast they went, how far they went. If she wanted more, Phil would rent a hotel room and they could spend the evening talking, watching a movie and cuddling with some microwave popcorn.
A few were looking for the intimacy missing from their lives and wanted to touch or be touched by another human. He was open for whatever she wanted as long as they were both happy. These relationships usually lasted a few weeks to a few months and Phil tried to keep them fun but if the time came for them to go their separate ways he made sure they parted on the best terms possible.
While Phil was involved with a woman he would take his post down and when he felt the present relationship was winding down he would put it back up. He had been using this procedure for almost two years and when Phil recently logged into his account and checked the messages on his post, he saw there was one from 'TeachersPet'. He read her note..... there was something interesting in her well written response and he decided to send her an email with an invitation to give him a call at her convenience.
Although Phil had immediately responded to the message Phyllis sent after her husband rebuffed her for the last time, she spent a couple weeks working up the courage to send him a note with her photo and another week waiting to call the number he sent in the email. She thought it was karma that his name was Phil, so close to her own. He answered her call with a very kind 'Hello' and she could hear the smile in his voice. She said she was Phyllis and they chuckled about the similarity in their names.
They talked for a while as the conversation flowed easily..... Phil told Phyllis a little about his late wife and how much he loved and missed her....
