Friend with Benefits

He starts…with a kiss. A long, tender, lingering kiss along the side of my dick. His eyes closed he nuzzles gently into it. He looked so…so…happy. He felt no shame, showed no hesitation, he actually loved this. The first kiss is followed by another, and then another. This was entirely new to me. Where I came from there were ribald stories of Boston gals who would touch your privates with their mouth but I’d never been with one. I hadn’t been with many ladies to be honest, and certainly no girly men!

“Mmmf!” I tug and twist.

Grabbing my hips he whispers. “Shhhh.”

He runs his fine nose up one side causing it to flop over to the other side and swell a bit more. I lock my eyes on my treacherous member and will it to stay down, though is had a will of its own. As Jessie pulls away a moment to caress my manhood with his delicate fingers it surges with rising power.

“Mmm.” He smiles and starts to kiss it again. His lips parted now they were softly sucking kisses and even the occasional little lick. Thus far he still focused on just my shaft.

Around the room the rest of the family watched on with rapt attention. Helen rocked and knitted as the other three snuggle together and watch the action. There was a strange air of normalcy among them and I got the sense that watching others have sex was not an unusual activity in this room. Just another evening’s entertainment.

My foreskin being pulled down pulls my attention back down to my groin where I am just in time to watch the pretty young man kiss my bulbous tip. With that sweet yet sinful look in his brown eyes he glances up at me with a wicked grin. Looking down at him gazing back up…damn if he wasn’t the prettiest thing to ever touch me in a sexual way.

“Hmmm.” I whimper and weakly shake my head no.

He shakes his head no back at me, then opens his lovely pink lips and slips them over my penis

“Hmmmm!” My eyes roll back as Jessie’s warm wet mouth wraps around me then takes a long strong suck as his lips glide up my shaft. It felt so…fucking…good! NO! I shake my head and snap back to my senses. I didn’t like this, I didn’t like this, I didn’t… “Mmmmmm!” I groan through my gag again as the Bailey boy takes another long hard draw up my cock.

“He likes it.” Elsie whispers.

“Course he does.” Her father says back.

“Mmm, mmm, mmmm.” With each slow suck Jessie lets out his adorable little coos and hums. The way he could make those sounds, those high feminine sounds, it had a way of cutting through my defenses. “Mmm. Hmmm. Nmmm.” He starts to bob up and down, his mouth and tongue making me feel things I never had before. Nice things. His hair looked so soft, the skin of his neck and shoulders so smooth and supple, and his lithe body really did look so lovely in that dress.

No! No, no, no. I send orders down to my dick. Don’t you dare get hard! He was a man! I was a captive! I was being watched! This was all against my will! No man could enjoy such a fate as this.

“NNF!” I flinch as he cups my balls and fondles them, juggling them between his fine fingers. I look the ceiling once more and hopelessly try to block it all out. “Hmmmm.”

“Mmm, mmm, mmm.” Up and down Jessie goes, sucking and slurping as contentedly as a hungry little calf on the utter. He pauses to suckle for a time then teases my tip with his lapping tapping tongue. Slipping off he kisses and licks and whispers sweet little things. “I love your cock Mister Devlin. God I love it so much.”

When I at last look down again I see him gazing up at me with my fully erect and rock hard member pressed against his smiling face.

“So cute!” Elsie chirps.

“Ha ha!” Fiona chortles. “I think ya might have him beat little brother.”

“Maybe.” Jessie says as he stands up, careful to keep my wet glistening dick in his hand. “Pretty close.”

What was he doing now? Why was he standing? I soon get my answer. Lifting the front of his dress up he exposes himself to me then climbs back up on the chair with me. He slides his cock alongside mine and takes them both in a soft grip. He was as hard as I am.

“Rrrr.” I bite down on the gag and pull against my bonds.

Rocking his hips his length slides along mine as his grip hold them together, each time he pushes forward our balls come together. As he mentioned, our two members were indeed pretty damn close in proportion. He only does this for a short time before, in one big motion, he rises up my body so that my dick slipped down beneath his sack then rests his weight back down. In a single go he mounts me. My tip finds his anus then immediately penetrates it.

“Ohhhhhh.” Jessie sighs happily as he settles down on top of me.

“HMMMM!” My steel hard cock glides into the hottest, tightest, nicest damn hole I ever felt!

“Ohhh, Mister Devlin!” He moans and lets out a long breath. “Ohhhhh.”

“Hmmm!”

“I bet you barely feel that little pencil pecker.” Fiona prods. “Ha ha!”

“Oh, I feel him. Ohhhhh I sure do, I tell ya what.” Jessie sets out the skirt of his dress so that it covered everything happening down there up. He smooths out the floral front, trying to look good I guess, then grabs his pecs as if they were breasts. He grinds down into me. Fuuuuuck did that feel good! His dick skitters across my belly as he presses down to feel every inch of me. “Ohhhh yessss.” He closes his eyes and bites his lip as he blissfully savors the sodomy.

“Hrrrm.” I squirm beneath him which only makes things feel better.

I had a clean shot. I could heat butt right now and he would never see it coming. But as I look up close at this peculiar young man…I can’t bring myself to hit him. It would be such a shame to break that beautiful slender nose or bust up those fine lips. He slowly opens his eyes to see me staring at him and gives me bright smile and a peck to the cheek.. “I think yer pretty too mister.” He whispers, just for me.

Pulling my head into his chest he starts to ride me. I smell his perfume and sweat, I feel his soft dress and the silky smooth skin of his neck against my temple, and along my stomach I feel his arousal sliding up and down as he grinds and rides my cock.

“Ohhhhh!” His soft lilting voice breaks the quiet of the room. Damnation this fella sounded like a lass! “Ohhh, Mister Devlin! Ohhh yes, yes. Ohhhhh yes.”

“Mrrrm! Mmmm!” I moan through my gag though I didn’t mean to. I fight back these incredible feelings the Bailey boy was eliciting but I was fighting a losing battle. Comparing Jessie’s ass to the women I’d been with was like comparing hardtack to fresh baked bread. A bit of an exaggeration, but holy hell did he feel good! He was so tight, so wet, the texture of his insides gripped and milked my cock in ways that curled my toes. “Hnnngh!”

Still his voice sang, softly into my ear as he licked and nibbled at the sensitive fringe. “Ohhh yes. Ohhhh Mister Devlin. Mmmm. Fuck me. Ohhhh yesss. Fuck meee.”

My cock wasn’t the only traitor on my body now as my hips start to thrust with the feminine man’s riding and a disturbing pressure began to build in my loins.

“There he goes.” The pater familias says approvingly. “Now he’s gettin into it. Doin good boy.”

“Thank you Daddy.”

My fingers dig into the grooves Fiona had already worn into the chair and my muscles tighten as I try to hold myself back. Jessie must have felt my taut body and knew what it meant. He pulls back, holding my head at the sides, and gazes deeply into my eyes as he continues to ride.

“So soon?” He titters with a saucy wink. “You must REALLY like me Mister Devlin.”

“Hnnnnmmm.” I whine as the urge builds and builds to his incessant mind-bending riding.

“Mmmmmm.” He mewls sensuously. “Cum for me? Please. Please Mister Devlin. Ohhhh. Gimme your cum.”

I fight it with every ounce of will I had, but Jessie’s slick gripping hole and lewd needy tone and fetching looks were just too much for me. I bite down, I grip the arms, I clench my ass, my whole body as tight as a snare drum as Jessie rides, rides, rides with merciless persistence.

“HNNNNNGHHHH!!!” My nut hits me like bundle of TNT going off in my nethers. Nooooooo! Yessssss! “HNNNNGHHH!”

“Ohhhhhh yeeeessss!” Jessie moans as he continues to hold my eye contact. “There it is Mister Devlin! Ohhhhh yessss. I feel that hot load burstin inside o’me!”

“Hnnnnnghhhh!” I buck and spasm and snort through flared nostrils as my throbbing cock pumps wad after wad of hot cum deep inside this beautiful young man’s ass.

“Wait! What? Already!?” Fiona throws her head back and points once more. “AAAAAHHH HA HA HA HA!”

Elsie titters softly as the parents share a look of parental pride at their son’s achievement.

“Hmmmmmm.” I whimper as my climax starts to fade. Still Jessie rode.

“I think we can be friends now.” He says with a little kiss to my forehead. “Now that we friends you can have me anytime…Case.” He giggles…and keeps riding. “You don’t need El or any o’my kin. I look after you real nice Case.”

“Hrrm!” I grunt and try to pull away as what had been so damn pleasurable started to pass over to becoming unbearable. “HRRM!” I thrash.

Jessie’s grin widens and his tunnel tightens around me and still he rides. He stays real close, grinding hard, not giving my spent and sensitive willy a moment to escape.

“Hnnnngh!” I let out a pained groan.

“He he he.” The dad chuckles. “I bets you feelin that law man.” He says. “You riled mah boy up. He won’t stop now till you shootin dust.”