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John F. Kennedy’s Campaign Plane “The Caroline,” 1960
The strenuous flight to Massachusetts had lasted, by Jack’s count, two hours so far. He was flying back from a long night of campaigning, and his brother had gone with him, doing the kindest duty of organizing the campaign venues. Bobby had tired himself out, as always, and he needed rest. His conviction, while passionate, often ended in exhaustion, yet he never allowed himself to quit. Jack admired this in Bobby; however, he rarely had qualms when Bobby needed rest.
Often, Jack slept alongside Bobby. They worked together and ate together, so it made sense for them to sleep, well, together. Jack was often in a different hotel room than Bobby, or he was sleeping on the floor due to his back issues. However, this campaign led to a change in habits. Now Bobby was sleeping peacefully against the plane headrest. His breath was faint, the only noise in the private plane. Jack didn't have the heart to wake Bobby up, not when he was sleeping like an angel.
Bobby's eyelashes appeared long and lustrous, and his hair fell to cover part of his left eye. His lips were lightly coated with drool. The man's state was a sight to be beheld; therefore, Jack held this moment in high regards.
Jack paid close attention to the younger man's breathing—there was nothing else to pay attention to, after all. Jack reflected on how Bobby's mouth was slightly agape and wondered how much that mouth could do if Bobby was awake. Jack's eyes flicked between his brother's mouth and suit pants. The black fabric fit Bobby well in the thighs and was generous in the crotch. Jack wished that he could touch the fabric, yet he feared it would wake Bobby up.
However, Jack was always daring. There was no opportunity not worth taking, even when partaking in it could mean your entire family's political demise. If one copilot or if one campaign staffer in the back walked in, Jack would surely be forced to pull out of the election, and his family would be seen as perverted and fraudulent. This fear did not stop Jack from slowly gripping Bobby's thigh.
The suit fabric felt almost as exceptional as it looked, and Jack could hardly resist taking more. Jack slowly moved his hand toward Bobby's inner thigh, desperate to touch the fabric and, potentially, Bobby's skin.
Bobby's body shifted into Jack's touch, and Jack could've sworn that he was about to be done for. The younger stopped right there, and Jack let out a slight sigh of relief. If Bobby knew that Jack was doing this, that Jack craved this, he would surely object.
Jack saw Bobby's persisting slumber as a go-ahead and moved his hand toward Bobby's zipper. It was only then that Jack noticed that Bobby had been wearing his suit. The older brother wasn't complaining—it had fit his campaign manager beautifully. Jack realized that he had been observing and not acting, so he quickly got back to more “urgent” matters. Well, they were urgent to him, at least.
Jack unzipped Bobby’s suit pants, and Bobby hardly stirred. Jack figured that Bobby hadn’t slept in a couple of days, and Jack understood this. Jack caught a glimpse of the sunset outside of the plane; he had been ignoring the outside: it simply wasn’t as beautiful as Bobby. Jack soon undid Bobby’s pants button which was also Jack’s pants button. Jack briefly considered Bobby stealing his clothes and ultimately decided that it was adorable.
Bobby’s light blue boxers were exposed, and Jack was filled with anticipation and pure adrenaline. There was a tent in Bobby’s boxers from Jack touching his thigh prior. Jack began to notice Bobby’s breath hitching and subtle whimpers. Jack had been teasing his brother’s thighs for the past five minutes, so it didn’t alarm him when his brother was having whorish dreams.
Bobby’s cheeks were a beautiful light pink as he continued sleeping, snoring lightly and mumbling “Jack...” This startled his brother--had Bobby woken up? Yet Bobby’s eyes were still closed, and Bobby’s erection was still neglected. Jack pushed his momentary fright and cupped Bobby’s erection, undoing the confining button with his other hand. He began to rub his brother’s erection, feeling the soft skin and the subtle veins. Jack rubbed Bobby’s tip, smearing precum across the tip with his thumb. God, how desperate had Bobby been?
“Jack... More... Please...” The words quietly escaped Bobby’s lips. It was still clear that Bobby was asleep and nowhere near awake. Jack’s breath hitched as he gave in and began to stroke Bobby slowly, listening to Bobby’s compliant groans. Jack admired his brother’s slipping words, and he enjoyed how it was his name over and over--like a tape recorder appealing to his most devious thoughts.
Jack picked up his pace, stroking Bobby’s painfully hard cock which was already slick with precum. His pace was hardly frantic, but Bobby still highly enjoyed it by his repetitions of “yes” and “Jack.” There was something that changed in Bobby as Jack increased his pace, but Jack barely cared. Bobby was close, and Jack would do whatever he could to feel Bobby’s cum all over his right hand.
Bobby’s moans got louder, yet they were seemingly careful as if he was trying not to alert anyone. Jack’s pace was now brutal, and Bobby came, his eyes clenching. Sweat had accumulated on his forehead, and Jack made a note to ask if Bobby had experienced a nightmare. Nightmares were the typical cause of night sweats, after all.
Jack tucked Bobby back into his boxers, doing the singular button back and zipping up Bobby’s/his suit pants. He licked the cum off of his hand, savoring his brother’s salty taste. It was unlike anything Jack had ever had. It tasted ethereal.
A few minutes later, Bobby opened his eyes. Jack smiled, greeting Bobby with a simple “Good morning. We should be landing in an hour. Did you get a good night’s sleep? I’m sure you needed that rest.” Bobby just grinned back and nodded.
“Y’know you’re sweating quite bad there. Did you have a bad dream?” Jack only asked this to embarrass Bobby, to see that shade of pink on his face again. “Oh, yeah. We’d lost the primaries or something and had to deal with Johnson, and then he ran again and won for twenty years straight. It was real hard to tolerate.” And Jack just laughed, completely unaware that Bobby had been awake for the last ten minutes.