Connor paused, resting on his legs supported by the little shelf on the chaise like he was sitting up in the saddle and getting ready to ride. He surveyed the coupled couple just below him. Sherry was dripping wet, and her juices flowed down her husband's cock like hot juices leaking on a turkey baster, except his dick was lot thicker, and most of it was hidden in her snatch. Her little dark pink rosebud was calling out, begging to be penetrated, and Dick's question about Connor and Dick soon being separated by just a little sliver of Sherry hung in the air.
For some reason, Connor suddenly recalled reading an advice column in one of his cousin's collection of 'stroke books' (as his father called them) when he was about 14 and curiously reading everything he could find about sex. It purported to be a letter from a woman who had finally convinced her husband to do a threesome with her and another guy, and she was looking forward to double penetration and massive orgasms. But in the end she was terribly disappointed because the two guys were so freaked out about making sure they didn't touch each other that they really couldn't get into the proper positions to penetrate her effectively and didn't pay enough attention to her!
Connor remembered what Polly had said about it not being enough for 'trusted friends' to just accommodate each other's kinks and that they had to learn to fully embrace them and get joy from them themselves.
Then, he bizarrely also remembered Mr. DuBois, his high school history teacher, who had given Connor his only exposure to classical philosophers so far in his young life. When talking about history, he would throw in parenthetical references to philosophy, quoting Sun Tzu or Von Clausewitz when talking about battles, and Nietzsche on revolution, etc. Connor could not remember who said it, but he recalled the idea that tactical surprise in battles usually does not come from not seeing something, but rather comes from seeing it and not realizing what it means.
He took another look at Sherry and Dick. What was he seeing and not understanding? What would it take to make sure they could all get the best possible experience out of this? Could he embrace this and get some joy himself? What did he have to face in himself? Suddenly he got an idea, two ideas actually.
"Well Dick", he finally spoke with false bravado, "I think we may soon have get a lot closer than that, because I think Sherry's 'tight little ass' as you called it, could use some lube, and it should be something a little more slippery than saliva." Connor leaned down and began to lick up the juices dripping out of Sherry and used his mouth to transfer them to her ass, touching both Dick and Sherry vigorously and intimately in the process. Both of them sighed, murmured, and squirmed. "Oh my, Connor" said Sherry "that's a good idea! And as a side effect of your efforts, I can feel Dick getting even bigger inside me.
In for a penny, in for a pound, thought Connor. "Do you think that's right, Dick?" he asked. "Oh, man, yes! It surprised the hell out of me when you started doing it, but my reaction is unmistakable!
Connor laughed. He remembered that his father used to say that sometimes being an officer just meant you had to act brave, even though you were really terrified! So he said "Well then let's get the full effect, not just a side effect!" And with that he began strumming the stiffened end his tongue back and forth left and right along the big shaft on the underside of Dick's cock, moving up to the point where it disappeared into Sherry, and then all the way back to its base and then back up and down several times.
The married couple practically sang a duet as Dick reveled in the stimulation and Sherry felt Dick expanding even further. "Ohhhh! Ahhhhhhh!"
Connor stopped his efforts, confident that Dick and Sherry had enjoyed them, and thinking maybe he had too. He put his still rock hard, but normally sized, organ up to Sherry's little rosebud and thrust it into her slowly. It was a perfect fit. He and Dick slowly found a rhythm. They gradually synchronized and extended their mutual thrusts into her, and soon Sherry was fully filled with phallus. After a few minutes of this her cooing noises became wildcat moans, and she began twitching like she might be having a seizure. But seizures are not usually accompanied by squirting sexual lubricant! She was actually having either one long orgasm or a series of short ones, but either way her muscle contractions were transmitted to both Dick and Conner easily through their shared surfaces. It proved too much for Dick to stand, and Connor could then feel him twitching and thrusting into Sherry as he shot off inside her. Connor followed in concert a second later and Sherry's sound effects went up in both pitch and volume. Dick kissed Sherry's neck in front, and Conner kissed her shoulders and back, and she actually lost consciousness for a while!
One floor above them, in the master bedroom of the estate, Polly and the Admiral were holding hands as they watched the 3D 4K video feed from the guest suite. "He's a natural, Polly exclaimed, "A stone natural!" The admiral laughed, and completed her train of thought "He's the Roy Hobbs of sexual adaptation and kink switching! It looks like your plan is moving forward, and much sooner than we dared to even hope! We have some quick work to do to get the next phase moving." They turned off the monitor and held each other tightly.
Back in the guest suite, the sound of labored breathing filled the great room of the suite. Gradually their heart rates and respiration rates fell back towards normal. Connor balanced on his still slightly shaky legs and stood slowly, then stepped down from the chaise lounge to the floor. He saw that Dick had wrapped Sherry in his arms and they remained locked together on the chaise. The clock on the wall read 5 AM.
He spotted a large wicker basket under one of the chaise lounges and opened it to find some cotton towels and what looked like a silver ice bucket. It turned out to contain warm wet towels infused with a slight hint of lavender. He took one and wiped down his face, then his cock and the front of his body that was covered with various secretions from him and his two playmates. Part of the hamper was a plastic lined receptacle for, he presumed, the soiled wet towels. He tossed his in a grabbed one of the warm dry cotton towel to dry off with. It felt wonderful.
Sherry rose on still wobbly legs and he handed her a wet cloth, and then one to Dick who followed right behind her. The both enjoyed the sensuous feel of the warmth and cleansing. Sherry needed two! Dick and Connor sat opposite each other on the two lounges also using their dry towels to mop their brows and tried to recuperate. Sherry bent and kissed them both on the cheek and said "there should be a cart with a midnight snack in the kitchenette, and we can roll it out here." Connor looked and saw the open door to the little kitchen and what looked like a hotel room service cart just inside the door. Sherry then giggled and said "First dibs on the bathroom!" and ran in and closed the door behind her. Dick laughed "Some things about women never change!"