Getting Back in the Dating Pool, 2
Matt’s Friend with Benefits story continues. Read the first story before diving into this one.
Matt and Madison were lying there catching their breath after their rather intense welcome home sex as she continued, “Matt, I’ve met someone.”
It caught him a bit off balance, but it sort of explained the events of the last hour or so. A sort of last huzzah before he was cut off. He had known it would happen sooner or later, but later was always better. He was trying to figure out what to say, realizing that they probably would not be sharing the benefits of each other’s bodies again.
“Are you upset?” She was watching his face anxiously.
“Not upset, more disappointed. Not with you! Just that I’m losing the benefits. But I did know it would happen. So, tell me about him.” He was a bit surprised at how well he was taking it, not really angry, just a bit of sadness.
“Well, we met at the gym. Alan is a couple years older than me, evidently I like the older guys.” She was teasing him a bit, which gave him a bit of hope that she wasn’t trying to burn bridges. “And we’ve been working out together for a couple of weeks and he asked me out Friday and I went and we had a good time. I like him, and I think I want to see more of him.”
“Well, it is what our stated goal was, to get ourselves into a place where we could operate in society again. I was just always hoping I would ‘go first’ since you have a lot better prospects than I do.” She really wouldn’t have had an issue getting a date at any point in time, it was more a matter of her being in the right headspace.
“I wouldn’t be so sure about that! Look, I’ll let you off the hook for a workout Monday, but Wednesday morning, at the gym, usual time. And we won’t be alone. Alan will be there, and so will Star.”
“Yes, she asked me if I would help her train. She knew I had been helping you. And when she talked with me about it, she was asking a lot of questions about you. She tried to make it sound like she was just interested in the training side of things, but had definitely noted the changes you had made over the last few months and wanted to do the same. But I would say some of the questions were a bit more probing, as if she was trying to find out whether there was more to our relationship than just friends.”
He thought about Star. He knew who she was, and would often say hi as he passed her in the hallways. She was younger than he was, but quite a bit older than Madison. At a guess she probably split the difference between him and Madison age wise, putting her around forty or so. He’d only seen her in her Sunday clothes, the figure was pretty hidden, but nothing stood out. Part of that would be that he tended to focus on her long red hair when he saw her.
It seemed a bit awkward that first morning. Madison was her normal cheerful self, Alan was a bit standoffish, and Star was pretty quiet. He found it unnerving how Star seemed to be always looking at him. Madison directed them to the cardio machines. She knew he preferred the orbital types, to avoid the constant pounding on his heels. Whether she did it intentionally or not, she put Star on a treadmill two rows in front of him. He finally got a chance to really check her out. Pretty nice. The black workout pants she was wearing didn’t hide anything. While she might do with some tightening up, (who wouldn’t?), she was certainly closer to his ideal image of a woman. Nice curves and time flew by as he watched her red hair in a ponytail bobbing up and down and her rear end rotating and found himself with a bit of an erection.
After having settled into the new routine for a couple of weeks, Madison came right out and asked him. “So, why haven’t you asked Star out?”
“Does she know how old I am?”
“Um, well, I guess that I don’t really know what she knows. And what difference would that make?”
“I am twice your age, and as near as I can tell, I’ve got at least 10-12 years on her. I’ve gotten to know her, and I really like her. I certainly don’t want to creep her out. Guess I’ll have a chat with her tomorrow morning and make sure she knows how old I am. Oh, and just so I don’t forget, thank you. You really have been great in helping me out, getting me in shape and building my confidence. I appreciate it more than you could know.”
“Hey, it’s not like you didn’t help me out! I wasn’t feeling all chipper after the breakup.” It was the first time she had directly referred to the split that he could remember, so evidently there was some progress being made.
Matt and Star had started getting together a couple of days a week even when they weren’t training with Madison, and worked out at the same time. The next day he stopped her before they moved to actually hit the machines. She was looking good, with a tight t-shirt and leggings on, a nice flush on her cheeks highlighting her freckles and green eyes.
“So, Star, a couple of things. First of all, how old do you think I am?”
She looked him over. “Well, I know you are older than I am, based on comparing you with others I know I’ve always thought you were about 5 to 7 years older than I am.”
“You’re off by at least twice that much.”
Her mouth gaped as her jaw hit the floor. “Really? I would never have guessed.”
“Okay, I just wanted to make sure you knew what the gap was. I’ll let you digest that for a while. The second thing, as cheesy as it is, and I’m sure it isn’t the first time you’ve heard it, but your name fits you very well, you certainly are a heavenly body.” With that he went over to the weight machines and continued his workout, trying not to look in her direction. She sat there for a minute or two before starting her own routine. And he was glad to see that she chose a machine that was someplace he could see her clearly as she moved into the next phase of her workout.
He had to admit, Star set things up pretty well. Not one to wait around, she called him and told him that she was getting some work done on her car on Saturday and was going to drop off the vehicle after work on Friday. Would he do her a favor and pick her up from the car dealership and give her a ride home? In exchange she offered to cook him a homemade dinner that evening. Seemed fair enough and Matt suspected there might be more to it than just dinner, but didn’t set his expectations too high. While it wasn’t technically a date, it was certainly more of a social situation than the several times a week meeting at the gym. And certainly more intimate than actually going somewhere.
One of the nice things about being semi-retired is that he could pretty much set his own schedule. So it was relatively easy to show up at the dealership at the appointed time. She arrived a few minutes after he did and drove into the bays after waving to him. A couple minutes later she joined him in the car.
“Okay, Star, navigate me to your place!”
“Aye, aye, Captain!” and she proceeded to direct him to the appropriate location. The neighborhood was nice, neat for the most part and her yard was small. The flower beds were well tended, but the grass was dry and weed ridden. He pulled into the driveway. It was a small bungalow with two bedrooms upstairs and a main floor with a kitchen, living room and small dining area. The size would be about half the size of his ranch home. There was a basement that probably held a laundry area and the equipment for heating and cooling the small home.
She opened the door and the aroma of garlic and onion enveloped him, making his mouth water. He spotted the source, a slow cooker on the counter. Star held the door open as he walked into the kitchen. She went to close the door and they found themselves face to face, inches apart. It seemed only natural to kiss her, so he did. There was a bit of an initial surprise, but she returned the kiss without hesitation. He stepped back and she finished closing the door.
“That was special.” He had felt the tingles in the pit in his stomach, the ones that always told him that the kiss was a good one.
“It was. I wondered if we would even have a first kiss.”
“I didn’t want to rush anything and wanted to make sure you knew what you were getting.”
“I get it, and now, I’ve got it!” And with that she wrapped her arms around him and kissed him hard, holding tight for a minute. Reluctantly she released him, “Okay, let me get dinner finished!”
It was a good meal, low fat and full of flavor and vegetables. Madison would have approved. She might not have approved the two of them downing a full bottle of wine, but they both felt it was deserved after a full work week. They finished up and he helped with the clean up. As much as he hated doing dishes, he found himself with soapy hands scrubbing out the vegetarian lasagna pan. After rinsing it out he held it up to the fading light in the window and made sure it was clean before setting it in the drainer. Star had finished putting things away and when he turned around she was watching him. He returned the look and seemed drawn to her. He gently placed his hand on the side of her neck and she leaned into him, another stomach churning kiss that tasted of wine.
She took his other hand and lifted it up to her right breast, holding it tight against her. It felt good against his palm and was definitely larger than Madison’s. He lightly massaged it through the fabric. They broke the kiss off and edged away from each other, looking into each other’s eyes. She was three or four inches shorter than Madison was. He shook his head a bit as he realized that he needed to quit comparing everyone to Madison. But with his limited experience with other women, he realized that it was going to be inevitable, but he needed to make sure he didn’t say anything out loud.
She took him by the hand and pulled him into the small living room. It was dominated by the large television screen on the back wall, with a large, comfortable couch at the opposite side of the room, next to the front door. Star pulled him onto the couch next to him and cuddled up next to him, her hands starting to roam over his body. At least Madison had helped him tighten it up.
He wasn’t sure of how far she wanted to go, with Madison it had been pretty much understood from the start. With Star he didn’t know, he figured that if he kept himself to reciprocating her moves, he’d be safe enough. Star seemed to feel his hesitation and sort of solved the issue for him.
“Look I don’t want there to be any misunderstanding. I realize you are still in a rebound stage. After my divorce, I know I’m not in the market for another husband right away. I don’t think I’d ever trust anyone enough to tie myself to someone for the rest of my life, or long enough to go through another divorce which would probably be the end of me. Madison really helped me get off my butt and start feeling better about myself. And you were a part of that, both as a sort of example and as someone that seemed to find me attractive. So while I’m not looking for another long term relationship, I sure don’t expect to swear off sex for the rest of my life.”
“So we’ll just keep each other company for a while and keep everything on the down low from friends and family?” He was thinking “A friend with benefits again?” While it was a whole lot better than being friend zoned, it wasn’t ideal.
“I don’t think I mind people knowing we’ve got something going. It would make it a lot easier to get back into some sort of social scene if there was someone to go with. And you are certainly quite a catch, so there will be some jealous looks, which may increase interest in me. I’d love to have your arm when I go to my high school reunion in a couple months.”
That was more like it. No long term commitments, but no need to hide from other folks. That certainly made things better in his mind.
She pushed up against him and kissed him deeply, her tongue swirling around his teeth. Her hand gently worked itself over his torso, dropping a bit lower with every circuit as he rubbed across her back.. When her hand dropped to his crotch she discovered that she was definitely getting through to him. Weeks of sexual energy that hadn’t had a release since his last tryst with Madison almost a month ago saw an exit point and responded quickly. She slid down his zipper and worked her fingers into his boxers and the flesh on flesh contact made him gasp. He returned the kiss with strength and grabbed her ass with some confidence.
Matt’s mind flashed back well over a decade and surprised him with a memory. The time when the ass now grasped firmly in his hand had first caught his attention. It had been in a tight pair of gray dress slacks that molded around her shapely rear end. He didn’t remember the place, but the image was clear. She hadn’t been married at the time, though he was. Two months of working out under the direction of Madison was rapidly returning it to the firmness it had obviously had then.
She pulled away a bit, long enough to unbutton and slide her blouse off. Her stomach was flatter than it had been when they had started working out together, but so was his. And he knew she had seen the scar on his stomach as they had stretched and turned during their workouts. He wondered if Madison had planned some of the exercises and drills they did just to give them an opportunity to really see each other. Or perhaps she was doing it so she could watch Alan doing them. Regardless, it had worked for the two of them.
The lacy red bra did nothing to calm him down and he licked his lips. The full breasts filled the cups well and the blouse had not shown the charms of her cleavage, but he realized that she was still dressed for work, so wouldn’t have worn anything too revealing. And then he watched mesmerized as Star slowly allowed her pants to slide down her legs. They were good legs, well shaped, the thighs were creamy white and the bright red thong that appeared certainly kept him focused. She obviously had done some grooming down there, no stray curls peeking out the sides of the thong.
He stood up and took off his shirt, kicking his shoes off as he did so, aiming them to the side of the room. He hesitated about dropping his pants, but it would have looked pretty strange as his dick was already poking out of the fly. A quick flip of the belt buckle and the button and his jeans slid down to the floor. He flicked his foot to send them over near his shoes.
Star stepped into him and wrapped her arms around him. The skin on skin contact was sensuous and warm, giving him that same prickling sensation in the pit of his stomach. He wrapped his arms around her and kissed her hard, amplifying the sensation as their tongues danced over each other’s teeth as his penis rubbed against her warm belly.
When they came up for air she pushed him back onto the couch and kneeled between his legs, pulling his balls out of the fly of the shorts to join his dick in the air. She pursed her lips and blew a stream of air over his privates, causing him to shudder with the sensation.
“Oh, someone is sensitive!” She ran her finger through the curly hair that was sticking out of the opening. “And we’ll have to do something with all that!” Star started at the base of his balls and licked all the way up to the top of his shaft, forcing a series of little groans out of him as she approached the top. Star seemed to really enjoy giving head. She kept a running commentary going as she teased him, talking alternatively to him and to his penis. He was beyond talking and limited to a bit of a moan once in a while.
“What a nice shaft! We’ll have to trim off some of the curls so I can see you better. And not get little hairs in my mouth.” There was no question that she was good at it, swallowing him without hesitation. She bobbed up and down a bit taking him further down the road to spouting.
When she came up for air, “My ex-husband was an adequate lover, and I did love him. But he didn’t have quite as large a penis as you do. Most of the time I really liked a nice mutual sixty-nine. Not only did it get me to orgasm better, it was much easier to clean up and there was no risk of pregnancy.” Her hands continued to caress his balls and he placed his hands on the sides of her head, about the only part of her he could reach. Her hair was very soft and fine and felt good under his fingertips. Her breasts rubbed against his legs every once in a while, sending little waves of shock through his system.
“Oh, my, someone is getting excited! Can’t have you spoiling my fun too early in the game!” She pulled off his shaft and gave his thighs a bit of a lick with the tip of his tongue, his cock bouncing with every new sensation. After several minutes of her tongue moving back and forth, bringing him to the brink several times, Matt finally pulled her up and kissed her hard.
He guided her around until her knees were on either side of his head and pulled her down to him. Pushing the thong out of the way, his tongue reaching greedily for the folds of her slit. She returned to paying attention to his cock as he began to explore her wet pussy. She tasted different than Madison, a bit of spiciness in the aroma that he found very pleasant.
Now it was her turn to moan, the vibrations in her throat on his cock exciting him even more. Every flick of his tongue was matched by one from her’s and soon the two were licking non-stop. For several minutes the only sound was a bit of slurping and the moans of lust they were sharing. He could barely form the words to try and warn her of his orgasm before he erupted. Her tongue and throat were coated with warm cum and it triggered her own crisis. Matt found a flood of liquid in his mouth as she shuddered and locked up.
They laid there a few minutes, sort of catching their breath and the occasional lick on the other. Star felt good laying on top of him, her warmth enveloped him, a very satisfying and comfortable feeling. Once their breathing returned to near normal, she flipped herself off of him and he sat up, a bit light headed. Their eyes met and it sent another bit of a shock through his body. Her eyes were a deep green that looked almost cat-like. She smiled and pulled him up off the couch to crush him in an embrace that caught him off guard. There was no doubt the regular workouts had improved the strength of her arms, the hug made it hard for him to breath.
“That was very nice. Very, very nice. I think you’ve done that before, sir!”
“Certainly not the first time I’ve gone muff diving! And you are pretty talented as well!”
She laid another kiss on him, again probing into his mouth and he got the same thrill he had gotten from the first kiss they had shared. She took his hand and led him out of the living room and up the stairs. He found himself with a gorgeous ass right in front of him, framed by the strings of her thong. Matt couldn’t resist placing a kiss on each of the cheeks as they moved up the stairs, causing her to giggle a bit.
Once at the top, she walked into the room to the right. It was a nice bedroom and he was relieved that it wasn’t all pink and frilly. Definitely a girl’s room, but the colors were a bit neutral, mostly greens. She turned around to face him but continued to walk backwards until her legs hit the bed and she did a bit of a jump up and fell back on it. He looked down on her, the red hair framing her face on a dark green comforter, her breasts settling into nice pools of comfortable looking cushions on her white skin. For the first time he really noticed all the freckles running across her skin. Reaching down, Matt pulled the red thong down her legs, giving him the first real look at her entire body.
From the red hair that cascaded around her head, to the red polish on her toe nails, she was as perfect as any woman he had ever seen. She definitely had curves, her breasts were probably about a C, he didn’t have much experience with judging sizes. Her pubic hair was mostly gone, but there was a neatly trimmed strip of red hair above the slit. So the carpet certainly matched the drapes!
He slid his boxers down his legs and tossed them over near the door. His cock was rapidly growing to full size as he feasted on the view in front of him. There was a moment of hesitation, he certainly wanted her, but she seemed to read his mind and smilingly pointed to the nightstand. He pulled open the small drawer and found several condoms in plain sight. He grabbed one and ripped it open, rolled the latex sheath over his shaft and turned back to her. She hadn’t moved and he found that the height of the bed was at the perfect height.
It took but a moment to pull her to the edge and slide his cock deep into her wet pussy. It was a bit tight, but the feeling was wonderful and she gasped with the entry. Matt lifted her legs up to his shoulder and pulled her to him as tightly as he could. He stood there savoring the feeling and warmth, looking down at her beauty. Star’s eyes were closed, her mouth slightly open. He started a slow thrusting, in and out. She timed her breathing to match his thrusts and his body began to respond with every movement. He knew that this orgasm wouldn’t come quickly, her oral manipulations had taken the immediacy out of his need for relief. And while he was going to be able to keep this up for a while, it wouldn’t be long. He was grateful for the condom, helping to lubricate things and avoid too much sensitivity.
In this position he didn’t have to worry about supporting his weight with his arms, leaving them free for other things. A put of a push and he was able to caress her breasts as he thrust in and out. It wasn’t long before the tempo started to increase, naturally speeding up as he felt the growing sensations in his balls. He could feel them starting to pull up against his body as they were working hard to produce another ejaculation. Matt dropped his hand down her belly and used his thumb to rub up against her clitoris, eliciting a scream from Star. The shuddering that ran through her was enough to send him over the edge and he shouted with relief as another stream of cum shot into the condom. He stood there, breathing heavily and hugging her legs to his chest.
She brought him back to reality with a couple of pats to his arms. He pulled out, being careful to keep the condom in place. She grabbed his other arm and pulled herself up.
“Hang on a minute.”
She returned with a couple of washcloths. She handed him one and turned her attention to the wet spot on the comforter. He carefully removed the condom and cleaned himself up, but not before placing a kiss on the small of her back as she bent over the bed. Star giggled and finished her rubbing. Taking the items from his hand she brought him into the small bathroom and left him.
Matt thought about the last hour as he finished cleaning himself up. He stared at himself in the mirror, wondering what it was that Star saw in him. He supposed the gray hair could be considered distinguished. And he was certainly in better shape than he had been six months ago. There was no question that she had been enjoying herself, and he certainly didn’t have complaints, just a bewilderment that anyone as pretty as her would want to be seen with him. At least with Madison, there was no desire to be seen in public with him in a boy friend status, which he was certainly understanding about. With Star, she had said she had no problems being seen in public with him, had even brought up a future date, that was a lot more looking into the future than Madison and he had ever talked about.
He opened the door and saw that Star was moving around the bedroom. There was a bit of a lightness to her step, almost a dance to it. He leaned against the door and watched. She had brought his clothes up from the living room and they were neatly placed over the chair in the corner. There were a couple of glasses sitting on the dresser with a few bottles nearby. She finally noticed him and flitted over to him and gave him a kiss. “I wasn’t sure what you would like to drink, but there’s wine, beer, a couple of sodas and some cranberry juice, help yourself. I’ll be back in a few minutes!”
She popped into the bathroom and he found himself in her room. He decided on a beer and poured it out, a nice local micro-brew. Star had turned on the television, he looked at his wrist and realized his watch wasn’t on it. A quick glance and he saw it sitting on his pants on the chair in the corner. She had set the channel to the local hockey team and he realized it was still pretty early in the evening. Checking the time it was just about 9. He put on his shorts, he felt a bit strange just running around naked in someone else’s house.
He sat on the bed and watched the game sipping his beer until he heard the door to the bathroom open. She stepped into the room and the view took his breath away. She had put on a nice negligee, in black that contrasted with her pale skin and red hair. There was even a black choker around her neck and her hair was pulled into a loose ponytail that was flipped over her shoulder and cascaded down her chest. She walked over and kissed him on the cheek and settled down beside him.
“That was pretty incredible.”
Matt laughed, “That would be pretty much an understatement! You are pretty amazing!”
“I’m glad you think so. Um, stay the night? You don’t have anywhere you need to be, do you?”
“Not really. I have some yard work to do, but nothing pressing. No one is going to be waiting for me at home and I can turn on a light or two. Nutty Bar isn’t an issue.”
“The cat. Russian Blue that thinks she owns the house and me. Lot’s of food and water available, so no problem there.”
“Ah, a cat person! I like that.”
“I like the fact they aren’t dependent on me, they can fend for themselves and seldom wake me up to take them for a walk. It gets cold and it rains and I’d just as soon not have to get out of bed at O dark Thirty to let them out.”
She climbed up the bed and settled herself into the pillows and patted the mattress beside her. He slid up beside her and placed an arm around her. Matt decided that this was pretty nice and something he could get used to. He wondered how long it might last, she was obviously already thinking a couple months out, having mentioned the reunion to him. He was alright with that, nothing too long term, but indications that she wanted more than a one night stand. The morning was a long way off, but he looked forward to it and gave the warm body beside him a squeeze, just to make sure she was still there.
There wasn’t much in the way of conversation, they would make a few comments about a good play or thoughts about the weather and the coming week. Once the game was over, he turned off the television and turned his attention back to her. She smiled at him and the next thing he knew it was morning.