An Older Man for Caitlin Pt. 03

Over the next week or so, both Arthur and Caitlin were busy with their work and volunteering and what have you. While they talked most days and once got together at their favourite café, there was no actual contact and Arthur was starting to feel a little frustrated — he spent time each night with her pussy photo. They occasionally masturbated together over the phone which helped a bit.

After Caitlin's return to Arthur's bed, one of the first things they discussed was how to handle themselves in public. Arthur was fine having people think they were an item, but Caitlin reminded him that not all of his clients and circle of friends would be receptive to such a May-December relationship. She encouraged them to enjoy each other but to keep it a bit casual. Arthur thought it might be so that the younger woman could play the field still, something of which he was entirely accepting.

He tried several times to draw her out about the mysterious secret she had hinted at, but Caitlin held firm and would divulge nothing. She said he would have to wait until the next weekend, but that she would tell him once she'd decided how to do it. Mysterious as ever, she was.

Seeing how things were going with Caitlin, Arthur had availed himself of some little helpers for the bedroom. He was not having erectile problems, but best to head off any just in case. He got and filled a prescription for Cialis, similar to the famous little blue pill but more effective and safer. He was looking forward to its effect next time he saw Caitlin.

The week dragged on, but finally Saturday rolled around and it was time to reconnect with his young lover. He didn't know what to expect but she'd invited him to her house. It seemed that her two roommates were away so they could have freedom to play as they wished, he thought.

In the meantime, Caitlin was wondering if she had made too much of the little secret she was keeping from Arthur, but in the end, decided he would appreciate the reveal, and she'd make sure he enjoyed her talents in any case.

When Arthur arrived at Caitlin's place he found a small cottage set back from the street. The yard was grassed with small flower beds. She'd told him to look for the red door, and boy — was it ever red! Before he even reached the small patio she was throwing open the door to welcome him. Caitlin wore her usual yoga tights but this time, she had on a diaphanous printed top that only partially hid her lovely torso and breasts. He gazed openly at his young lover's attire, complimenting her easily as he moved into her arms. They kissed and Arthur's hands glided over her perfect buttocks but she pulled away before anything could develop.

She took his hand and virtually dragged him through the small living room, past a neat kitchen and out the back door to a veritable oasis of peace and greenery. And a swimming pool that he would never have guessed was there. The whole yard was protected on three sides by tall evergreen hedges and a fence. There was a narrow path along one side of the house, but that too was fenced and gated.

"Wow! This is amazing," said Arthur, "I love it."

"I thought you might, and it's pretty private so we won't be bothered by anyone we don't want," replied Caitlin. An odd response, he thought, but pushed it quickly out of his mind as Caitlin went back in for ice-cold beers. They sat on very comfortable patio chairs with only a small table between them for the beers.

After a long pull at the bottle, Caitlin renewed her invitation to Arthur: "I was a bit nervous to have you come here for the first time, but I also expected you would like my little garden of paradise."

"I certainly do. You can't even hear the traffic 40 yards away." He seemed astounded, "and still within the city. How much does this place cost you?" he queried.

"There are three of us as you know, Dave and Esther are a couple, and myself. All told, we pay about $2800 a month."

"That's expensive, isn't it?" he replied.

"Maybe, but with three of us all with good jobs, it's not that bad, besides, look around. Could it be any better?"

"I have to give it you: this is absolutely perfect. Did you say your roomies are away for a while?" He was a bit cautious about being caught out unexpectedly.

"They won't be back until late Monday night so we have it to ourselves..." she tapered off.

Unsure what to understand, Arthur again just ignored Caitlin's verbal drifting off.

They each polished off their beer and Arthur stood up to go get a couple more, asking her if she wanted anything else.

"No, I'm good. Just the beer, please."

Arthur came out again holding two long-necks and a bag of chips, spicy barbecue. "I thought these would go good with the beer."

Caitlin replied with an entirely different train of thoughts: "Remember when I told you that was a little something I should tell you, but held off?"

It was as if she had forgotten, and expected him to have also lost the thought. The truth was that he'd been trying to work it out for a week now, with no success. Arthur was a positive and confident man so he did not think it would be some bizarre fact or idea she would throw into his face, but he remained curious. "Sure, but I didn't want to push. Are we going to talk about it now?"

It was a funny moment as Caitlin started to say one thing, then changed to another, then finally a third approach. "Do you remember when we were up at your apartment and you had me up against the window?"

Arthur had carried her to the window, turned her around and bent her over at the glass so he could properly pound her fine ass from behind. He had loved holding on to her hips as he banged against her ass, each thrust making a loud pop as he slammed his groin up against her. She had been moaning loudly and pushing back enthusiastically until finally, he'd not been able to prevent his orgasm. He jammed in tight one last time and dropped his load into her tight little anus. It had been an amazing fuck, one that he could still remember in every detail. "Sure. We had a fine time of it, didn't we?"

"I think you're downplaying it a bit, Arthur." She seemed to remember it well also.

"Okay then, it was one of the best fucks of my life if you must know," he gave her a lewd smile, showing her the tip of his tongue.

"What I have to tell you is that all that time, I could see someone down below on the path along the park and they were watching everything we did. It was a couple holding hands, and the woman gave me a wave as you were fucking me. Does that shock you?"

"But you said no one could see that high up!" he offered. "You mean they could?"

"Hell yea! And that's not the secret, Arthur."

"There's more?" He was a bit surprised, and slightly disturbed that he'd been performing for strangers.

"This is the bit I am not sure about telling you... what I was holding back... I absolutely love having others watch me surreptitiously exactly as they were doing. I really get off on showing off."

Arthur was actually relieved that this was all she was worried about, until he realized that her exhibitionism extended to his participation. That, he was not sur about. He remained silent for several moments until Caitlin prompted him: "Should I have told you before? Did I do something wrong?"

The girl was genuinely concerned but it was clearly something that was important to her. Arthur understood that she'd opened up to him so he made sure she still felt safe and certain with him. "I admit it is a big surprise, especially the part about them watching us, but to be honest, now that I think about it there is a very erotic thrill to it, even if I didn't expect it. Is this something you have done often?"

"I have always been turned on by the danger of showing off. Just thinking about it makes we wet... like right now, Arthur."

"Have you done this much?" he asked again.

"Not really, not nearly as openly as letting you fuck me in the ass in front of a big picture window in the middle of the city. But I have done a few little things here and again."

"Tell me more." Arthur was getting surprisingly turned on and it was starting to show in his shorts, though Caitlin had not noticed yet.

"I used to go to the nude beach in Australia, almost every day. At first I really enjoyed taking Andrew with me: he had an amazing cock that every woman would stare at as we walked past, and more than a few men I might add. I found that very exciting, but we never did anything more than a fondle in the water; it wasn't that kind of beach, but I would have loved it if I'd been braver."

"You're right, Caitlin. That IS pretty hot. What else have you tried?"

Caitlin now came to the crux of the matter: "Remember that I was telling you about greeting you at our house when you came to meet my mom?"

"Okay, yes. What about it?"

"The only reason my mom was not home is that I told her you had called and cancelled so she went out. I knew who you were from before and I wanted to take a shot at you..."

"Taking a shot?"

"You know, I thought I could try to seduce you."

"Oh. Oh! But you were rather young for me," replied Arthur.

"Exactly, but I had got my nerve up before you showed up, then I chickened out. You might not know this, but when I saw you from my upstairs window, I had my fingers in my pussy, teasing my little clit. And when I came down, I had exactly nothing under that towel."

"That is pretty cool to hear now, and to find out how close we actually got."

"And when I shook your hand, I had the smell of my pussy on my fingers. I hoped that somehow you might notice. I even considered 'accidentally' dropping my towel as I walked up to meet you. But it was all too much and as I say, I totally chickened out."

Caitlin sounded positively disappointed, dejected even. But she perked right back up when Arthur replied that "one of these days perhaps we could replay that little scene, but without you backing out. What do you think?" He was already seeing the possibilities.

It was as if Arthur had given her a surprise gift full of glitter and creamy icing: "You would do that for me? Really? When can we do it?"

She really was like a little kid, but one in who was 20 years old and had the goddess body that always created a reaction in him: heart beating a little harder, blood flowing into the groin, and even a little weakness in the legs when she started taking removing clothes. "You can surprise me one day and I will know what's going on and try to play along. How would that be?"

Caitlin stayed quiet but he saw her slip a hand towards the crotch of her tightly covered crotch. She seemed to be doing it unconsciously but noticed as he was looking right at her fingers pressing up against her little mound. Instead of stopping, Caitlin leaned the chair back and spread her legs slightly so as to give him a better view. Her hand slid up to the elastic waist and pulled it out slightly to allow her other hand to slide in unobstructed by the fabric. As she did this, she nodded to Arthur's slowly tenting shorts and invited him to join her: "Why don't you slide yours out and we can jerk off together."

"If you want, I suppose." It was not as if he would (ever) turn down a request from this young woman.

"Oh, I want, pal. Whip it out so I can see it, see your hand stroking your hard meat, and cradling your big balls, too."

Arthur released the button on his shorts and lifted his butt off the chair just enough to yank down his lightweight summer shorts. He wore not boxers, flying free as it was. By the time his cock hit the warm air it was fully engorged and was bobbing with each pulse of his circulation.

"That's what I wanted to see. Thank you."

Caitlin went silent even as she shuffled her chair around to be almost directly facing his. She never paused the fingers at her pussy. She was completely wet with anticipation and excitement and by now, was burying two, now three fingers as deeply as she could. All the while, her eyes were locked on to Arthur's erection and his slow movement up and down the shaft. She prompted him, "really fuck your hand, Arthur, I want to see motion, speed. Do it faster."

"I'm afraid that if I get any more enthusiastic I will cum and leave you all alone."

"Okay, but when I tell you, I want you to match my speed — it'll mean I am about to cum, too."

They continued for only a few minutes more, Arthur slowing again and again to avoid ejaculating, until finally, Caitlin demanded, "Now! Fuck it, Arthur! Do it now! I want to see your cock spurt. Now you fucker!"

She was almost screaming as she had an orgasm, followed closely by a second that rocked her even more. Arthur, for his part, was still trying to hold off, but soon that was not possible. He had held off long enough that when it came, his ejaculation was powerful enough to shoot several feet, landing on Caitlin's thigh not once, but twice. He dribble the remainder onto his hand and shrinking hard-on.

Caitlin, meanwhile, was into at least her third orgasm only now she was just lightly thrusting two fingers into her pussy. She had never closed her eyes, always locking on Arthur's manhood as if she could feel it in her pussy instead of her own fingers.

When she finally stopped, Caitlin was wiped out. She had both hands inside her tights and one was cupped over her pubic mound as if to hold in the feelings of cumming so many times. Arthur stood up on shaky legs and moved towards his young lover. He put his left hand over hers, squeezing firmly against hers, and against her mound. With his right hand he fed her his glistening, softened cock. Caitlin opened her mouth to take him all in; with her tongue she cleansed his sperm off his penis, enjoying every lick, and even more so, the taste of it.

As Caitlin was reviving his cock, Arthur thought he saw movement in the window behind them. He shook it off as a shadow, easy to do as his boner was back and he wanted to put it to good use. That was not to be, not exactly, as Caitlin, even as she held on to his cock, wanted to talk. "I need to ask you something, Arthur," she said.

Distracted by her hand, Arthur mumbled something like, "sure, whatever..."

"How would you feel if we had someone watching us out here, you know, playing with ourselves?"

Arthur did not catch the implication, not yet, so he said, "that might be okay I suppose."

"Really? It wouldn't bother you to have someone voyeuristically participating with us?"

Realizing what Caitlin was talking about, Arthur responded: "What do you mean, a voyeur watching us?"

"Just what I said: someone who could see everything we did. Me with my hands in my tights, you with your hard cock in yours, and especially that amazing cum-shot when you finally orgasmed."

Arthur was getting nervous, outwardly. But inwardly he found it a bit exciting that such a thing could happen in the future. He replied, "I think I would be okay with that, but I would have to work up the nerve I think. What about you?"

"I have to admit something to you Arthur, and if it's an issue, I apologize in advance."

What in the hell could she be talking about, wondered Arthur.

"I thought I knew you well enough that you would be okay with it, so I already arranged for that to take place."

"Oh. Where? When?"

"My friend is in the kitchen right now, and she's been watching us from the time we came outside together."

Arthur's cock went from full form to limp in the bat of an eyelash. He was shocked to the point of putting his hands over his groin as if that would make any difference now. "What?! Someone's been watching all this?" he exclaimed with some shock.

"It's my best friend Deirdre and she is waiting for me to get your approval to invite her out here. But she won't come out unless you are completely okay with it. Can I tell her to come join us?"

Arthur could not understand how it would make a difference now to have his permission. After all, they'd been the object of this little voyeur already. No permission. Then he figured it out: Deirdre would be open to more than just a little watching, after all, she'd enjoyed this so far, hadn't she?

Trying to look downcast and a little dejected at the subterfuge, he said to Caitlin, "I suppose it would be okay with me, as long as you want to do it."

Caitlin was not deceived because despite his apparent reticence, Arthur's cock was already getting hard again, still in her hand in fact. She looked to the window and with a big smile, gave a nod to signal Deirdre's permission to join them.

Arthur was both hesitant and equally curious to see this new girl. What would she look like and how old would she be... oh! She was stunning!

Deirdre stepped out onto the patio dressed appropriately. That is she wore just enough to cover the best bits, but not a square inch more. Arthur looked upon the girl, awestruck at her beauty. This girl was different from Caitlin but a perfect match as if for bookends.

For her part, Caitlin let go of Arthur and skipped to her arriving friend. The two girls grabbed each other in a full-body hug, and kissed! A big wet one right on the lips. Arthur was dumfounded. There definitely was more to this than he might have dreamed.

Breaking apart from the hug, Caitlin turned to Arthur saying, "Arthur, I would like to introduce you to my best friend since junior high school, Deirdre."

The new girl reached out her hand to shake Arthur's who took her petite hand into his, not realizing the absurdity of the handshake as he stood naked from the waist down and sporting a thick, pulsing erection. "I am very pleased to meet you, Deirdre." This was weird indeed.

Deirdre's voice a soft and slightly sultry, but so welcoming, he thought.

Letting go of the girl's hand, Arthur took a step back and admired the young woman. She was about Caitlin's age and roughly the same height. Where Caitlin was thin and firm, Deirdre was soft and lush. She was certainly in shape, but with much softer curves that leaned to voluptuous.

More stunningly, Deirdre was the colour of a smooth, delicious Caramilk bar. Her skin was just as smooth as chocolate and such a rich chocolate tone that standing next to Caitlin they looked like exact opposites, but with all the best things in common.

Deirdre's face was stunning, beautiful with only a little makeup to highlight her features. Her neck flowed gracefully to her shoulders, making a perfect curve down to her breasts. These were quite a bit larger than Caitlin's. Their shape was such that they resembled a pear with a soft curve down towards the prominent nipples, covered, but obvious and slightly hardened. The curve of the upper breast meant a slight gap between the bra strap and her flesh. Her breasts curved past the nipple, rounding heavily to form the pear shape that Arthur loved so much.

"Deirdre, I know we have just met, but I have to tell you that yours may the most perfect breasts I have ever seen."

He couldn't believe his first words to the young women were so forward until he realized he was pants-free and showing himself off very effectively.

Deirdre's sultry voice replied, "thank you Arthur, that is such a lovely thing to know." She said this with no hesitation, and no sign of being offended.

Caitlin joined in at this point, "take off that silly top Dee, I want him to see how truly perfect those melons are!"

Arthur stood stock still but for his throbbing member as Deirdre took her sweet time removing the brassiere. She reached around to her back, pressing her chest towards Arthur as she did so, and unsnapped the garment. She brought her hands back around but held the small patches of delicate lace fabric in place for a moment before dropping her hands and letting the bra fall to the ground.

Arthur could have sworn Deirdre's breasts bobbed slightly though he was pretty sure it was imagination. Caitlin took Arthur's hand and pulled it towards her friends brown breasts with nipples now fully engorged from the attention. She cupped his hand beneath one of the globes while she herself took the other one, cupping the heavy shape as Arthur was hesitating.