"Merry Christmas Jack!" Will exclaimed as he hugged his friend. "Karen's by the booze, Grace is late as usual, so please, entertain me."
"William, I accept this challenge with all the grace and dignity of Cher," Jack said in his majestically flamboyant way.
"Please tell me you aren't going to crossdress."
"Not at all, but I brought us all a gift. Elliot!" he called to his son.
Elliot walked in to the apartment. The teenage boy had recently begun to fill out his body more, developing into the handsome man that he would become while still holding on to that adorably cute charm.
Will threw his arms around the young man, hugging him happily. "Merry Christmas buddy! It's been way too long."
"Uncle Will, yeah it has! I missed you!" Elliot replied as he snuggled into the hug. Elliot hadn't told anyone, and for obvious reason, but he had a crush on his 'uncle' Will. He knew he was gay, which wasn't a problem for anyone, seeing as how both of his parents were and everyone he knew was usually okay with it. But, he didn't want to get his hopes up so he never shared his feelings, never revealed anything, and settled for the smallest affections he could get. Like a warm hug.
Soon he peeled himself away, sitting down and adjusting the small lump that had begun to form in his pants. He was almost certain nobody had noticed.
When Leo and Grace arrived, the party began. As a teenager, obviously Elliot felt a little awkward among them all, though they tried to fit him in. Eventually he excused himself to use the bathroom, while in all honesty he meant to explore the apartment. First was the bathroom because hey, when you gotta go, you gotta go. He searched around and found Will's extensive selection of scented shampoo's, body scrubs, and colognes before he found the thigh-high bathrobe that he was fond of.
Elliot slipped it on over his clothes, sniffing the collar for the smell of Will, enjoying the softness of it. He put it back, readjusted himself, and headed to Will's room. The first thing he did was pull open the closet doors and just stared at Will's clothes. On one half were all of the bits and pieces of his many suits. On the other were his tight-fitting jeans, khaki's and an assortment of shirts ranging from polo's to a mesh thing that had probably been a gift from Jack.
Next he began rummaging through the drawers of Will's dresser, finding more pants and assorted clothing pieces until he finally reached the top drawer. He licked his lips in anticipation and was greeted to Will's underwear drawer upon opening it. His hands rubbed through the tighty-whities and assorted briefs that Will was fond of until he felt something hard under one. Moving the underwear aside, he found Will's dildo.
It was easily 8 inches, maybe 9,with a knob at the bottom to make it vibrate at different frequencies. He picked it up and just stared at it in awe. In his hands he held the thing that had penetrated Will probably too many times to count. Elliot tentatively stuck his tongue out and licked the fake cock. He carried it to the bed and sprawled out, still tasting the cock. His free hand crept inside his shirt and began to tweak his sensitive young nipples, causing him to moan softly.
"Now, that is quite a beautiful sight," Will said as he walked into his room. Elliot jumped in fright but Will just told him, "Please, don't let me keep you. You were having such fun it appeared."
"Uncle Will, uh, I was- I mean, well-" Elliot tried to stammer out.
"Shh. You know, I always loved the way you called me 'Uncle Will.' It got me so horny sometimes, definitely made it dirtier whenever I fucked myself with that thing, thinking about you, letting you take me. Would you like that, Elliot?" Will offered to the eager young man. Will undid his tie, letting it fall onto the mattress as he moved closer to Elliot. He crushed his lips against the boys so forcefully that Elliot gasped against them.
He then laid back and kicked his pants off. "Elliot, take off my underwear," he told the young man.
He nervously stepped forward and allowed his hands to creepy up Will's thighs before removing his underwear and coming face to face with the man's dick.
"Would you like to see something, bud?" Will asked as his hand reached for his lube
Elliot, speechless, nodded his head and licked his lips, watching in anticipation as Will began to finger his hole open, preparing himself. At the sight of Will with a vibrator in his ass, Elliot reached his orgasm, cumming while fully dressed. Will noticed and brought the boy too him before undressing him and nuzzling his face into the boy's cum dripping cock, licking up the dribbling liquid. Elliot moaned in ecstacy as he received the best blowjob of his life. Will knew exactly what to do with his tongue, when to let his teeth just barely graze the skin. After a few minutes Will pulled off the dick before him and turned his ass to Elliot, removing his dildo.
"Fuck me, Elliot."
He eagerly dove forward, ramming his aching dick into Will's ass, enjoying the sensations caused by the tight hole surrounding his member. He began pounding into the older man, arching his back and changing his tempo and direction so that Will never got to set a rhythm. When he hit the man's prostate, Will began stroking himself harder and had to choke himself with Elliot's boxers so that he didn't scream as he came. He tightened his ass which brought the boy to climax also, filling Will's hole with his second load.
"We are definitely doing this more often," he told his favorite 'uncle.'
"Don't you worry about it. I'm not about to let a great fuck like you get away from me." With that, the two re-dressed and went back to the party.