Disclaimer: I try to make the photos correlate to the year, but I have no idea about it relating to the specific dates ¯\_(ツ)_/¯
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After years of hard work, Paul and his band had released their first single: "Love Me Do". What's more is that it peaked at number 17 on the UK charts. Needless to say you were very proud of him. This, along with finding a manager, seemed to be a turning point in his career, and he was beginning to play gigs more frequently.
He had played a lunchtime show at the cavern, then traveled to Crewe, Cheshire to play at the Majestic Ballroom. The problem was that his energy level would just get so high from performing. As the night winded down, he needed help to wind down as well.
You'd brought him back to his hotel room, worn out, though still talking loudly and walking around. You got him to lay down, promising you'd help him relax. He now had his head resting on the pillow, eyes shut peacefully. He was still clothed, wearing his turtleneck and trousers, though you had pushed it up slightly to expose his navel, and had undone his fly.
Paul's hands were tangled in your hair, his legs slightly apart, head tilted back, and mouth agape, as you sucked him off.
You'd been winding him up for a bit. When you'd first got in, he wasted no time in joining you on the bed, pushing himself against you and feeling you up. Normally you'd be fine with this, but you could tell that he was overexerting himself.
You took over for him, moving so that he could rest against the headboard. You massaged his thighs, releasing the tension there. He was already hard by the time you unbuttoned his trousers. You could feel the heat radiating off of his member when you pressed your lips against it.
You glanced up to see him gazing down at you with unfocused eyes, lips parted. You grinned up at his dazed expression.
You raised your head off him, and began to slowly stroke him off, your opposite thumb rubbing against his perineum.
"Say, Paul, could I try something? I'm sure you'd enjoy it." You said.
"Hmmm?" He drew out, his voice deep.
His eyes were still closed, focusing on the sensations.
"I heard men have this erogenous zone, and it feels even better than getting sucked off."
"Oh, where?"
"Well... I have to touch you, uh, on the inside,"
"What?" He mumbled, opening his eyes.
You moved the thumb on his perineum lower, applying slight pressure as to signify what you meant, but not so much that it'd slip in. You traced around the rim.
He raised his head slightly, eyebrows furrowed. He was in a hazy state from the pleasure and sleepiness, your hand still slowly stroking him.
"Oh no, you don't mean to finger me?" He muttered.
"Only if you want to," you paused, "supposed to feel incredible though."
He thought over it. Mind clouded with lust, he was more preoccupied at the thought of more pleasure than keeping his pride.
"It'll stay between us, yeah?" he said
"Course"
You wet your finger in your mouth. Your fingers were rather slender, so it shouldn't be too much of a stretch.
You inserted your right pointer finger inside, feeling around, your left hand still stroking him off.
"Feel anything?"
"Dunno, s'a bit strange feelin" he mumbled
You pushed deeper, trying to find what you were looking for. When you brushed against a bump, and Paul let out a whine, you figured this was it.
"Oh! Found it!" you said
You began to focus more on that spot, applying more pressure, covering the entire area. You tried different things in order to explore the reactions he'd give.
His face was red from both self-consciousness and the intimate stimulation.
He closed his eyes again as they were rolling back. It seemed that he was self-conscious of the high pitched noises he was making each time you pressed into the spot.
Usually when he fucked you, his moans would be deeper, coming from the back of his throat. He'd sigh and exhale some, maybe getting higher pitched when he got closer and more desperate. Maybe something about this brought out the upper half of his vocal range. He whined and squealed at the sensation, spreading his thighs and arching his back.
"Does it feel good, Darling?"
He hummed for yes, keeping his eyes shut tight.
You kept massaging the spot, and picked up the pace of your left hand that was jerking him off.
Paul was a mess, rather loud too. His face was flushed with a sheen of sweat like earlier that night on stage. He was gasping for breath and unconsciously thrusting into your hand.
It wasn't long before he was cumming onto himself, over his soft stomach and pretty chest. Some got on his chin. He lay breathing heavily, recovering.
You got up from the bed to get a warm cloth from the hotel bathroom, then ran it over his body, wiping all of the sweat and fluid off.
"Oh my," he mumbled, looking at the ceiling, "I didn't know I could cum from that."
You brought the towel over his neck, softly toweling off his forehead.
"This doesn't make me a girl does't?" He questioned leaning into your administrations.
"Course not, women don't have that spot. If you were a girl, you wouldn't have felt anything special."
"Yeah but, getting fingered I suppose."
"I don't mind, I won't tell anyone anyways." you placed a kiss on his jaw. "I like getting you off."
He slept soundly that night.
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FanficAnthology of pegging Paul (among other things) throughout the years. It spans from 1962 to 1994 Its not a narrative love story, but more of an interconnected series of events. It's in the second person. I tried to make any physical descriptions vagu...