Your Second Virginity

(I HIGHLY doubt I need to add this warning at this point, but I will anyway. This is a flat out gay chapter. No trap/femboy/crossdresser defense mechanisms to save it this time. Plus Jesse bottoms. Just thought I'd give you guys a heads up in case you want to skip it.)

Sitting in the living room trying to pretend to watch a show was both exhilarating and torturous. Both you wanted nothing other than to be alone right now.

Mercifully...your mother had figured this out.

The moment the kitchen and table was cleaned up your mother comes into the living room and announces. "I'm sorry boys, you'll have to excuse me tonight. I'm going to take Chloe home. She took the bus here."

"Oh!" You say. "Okay then." Sweet! Some time alone!

She then continues. "I think first though...I think we'll go see Peggy." Your mom looks at you. "I think my sister and I have a lot to talk about."

Your heart swells in your chest. "I think that is a really good idea Mom."

She nods. "I hope you two can manage on your own for a few hours."

The subtext to her words were unmistakable.

She had said she was going to turn in early to give you some space, but this was far better. You smile up at her. "Thank you Mom."

She grins. "You're welcome sweetie. I hope you two have a lovely evening." She looks at Casey. "Look after my boy. He's...he's my baby."

Casey lays her head on your shoulder and strokes your chest. "I'll look after him Ms Bailey."

Your mother takes a long thirsty look at Casey and sighs. "Ohhh my. Um...yeah." She turns her head. "Come on Chloe, we better get going." She then turns to put on her shoes.

Chloe comes in behind and gets ready herself. Looking at you and Casey she smiles. "Have a good fuck!"

"Oh my goodness!" Your mother sputters. After flustered and busy few seconds she chases Chloe from the house and follows right behind. As the door closes the house falls quiet. You and Casey were alone!

You listen to your mother's vehicle start up and pull away from the house.

Not a word is said. You and Casey were on the exact same page. Taking Casey by the hand you silently lead her to your room. She follows your lead without question. You enter your room and close and lock the door behind you.

You look upon your ravishing girl, it takes your breath away. She too was breathing in long but shallow breaths, excited beyond description to be with you right now.

She closes her eyes and swallows. "Jesse."

"Yeah."

"Do you think I am beautiful?"

"Oh my god yes!" You reply instantly. What a question to ask, you were WILD about her!

"Give me...a moment. I need you to see something." She seemed tentative yet committed doing what she was doing.

"Yeah, of course." You say. You wondered what was going on.

She nods. She walks to her overnight bag and pulls out a small kit. You stand and wait, wondering what was up. Over the next few minutes she proceeds to clean the make up from her face. She removes her jewelry. She undresses, not in a sexy way however but a plain efficient way. She then goes to your dresser and dresses herself in your clothing, a plain blue t shirt and cargo shorts. Finally she puts her long flowing hair up in a loose man bun.

Without the makeup, without the cascading hair, without the jewelry or perfectly fitted women's clothes...a man now stood before you. Casey had never shown you this side of himself. Even naked and straight out of the shower he never looked this boyish.

Casey, transformed, turns back to you. He asks nervously. "Jesse, do you still think I am beautiful?"

You smile. Fuck, as if this meant a thing to you at this point. You understood where he was coming from and you were glad he showed you this side of him...but it just didn't matter. He was just as attractive now as before, just in a different way. Instead of answering the question you slowly and seductively walk up to him. As he reaches for you...you spin around. He pauses a moment before embracing you. His left hand snakes around your waist as his right comes round your chest. You push back into him, making special effort to press your ass into his crotch.

"Do you think I am beautiful?" You whisper.

You feel his hot breath against your neck. "Ohhhhh god yesssss!" His arms tighten around you and you feel his lips press into the short hairs of your neck as he kisses you. You close your eyes lean your head back toward him. He continues to kiss the tender flesh around your neck as you begin to grind your tush back into him.

"I want you inside me." You say, your voice hushed and hot with passion. "I want to feel you my beautiful man."

"Ohhhh Jesse." He sighs. "Ohhh baby, I...I...I love you."

There they were. Those three magical words. Those three perfect wonderful truthful words. You'd only known Casey a short time but by god you had never heard anything as honest in your life.

You turn your head and kiss his lips hard. "I love you Casey."

His lean arms flex and he pushes into you. You put your hands over his and hold him tight as you pull him gently toward the bed. Like a skilled dance partner he moves with you gracefully. As you reach your bed he guides you down. You follow his direction and come to lay on your stomach across your bed, he lays on top of you. His weight on top of yours felt incredible. He continued to kiss and suck along the side of your neck and over your cheek and ear. His warm breath tickles your ear.

You could feel his excitement surge along the valley of your back side. You were both so god damned horny you knew there wouldn't be much foreplay. Some part of you worried it might hurt, but a much more dominant part of you only wanted him inside of you. He had given his virginity to you, it was your turn to give yourself to him.

"Unhhhhhh." You moan as you push your butt back up into him. He lifts from you and you hear the quick rustle of cloth over skin. Out of the corner of your eye you just make out your blue t shirt being tossed to the side. His hands, fingers splayed wide, push up your sides, taking your own shirt along for the ride. You raise your arms to make it easier. Casey quickly pulls the shirt from you. He kisses and licks your bare back as he start grinding into you. Even through both your pants you feel his rock hard cock perfectly. "Ohhhh Casey." You moan again. "Ohhhhh."

You reach down and unfasten your pants. You had barely taken down your zipper when you feel them being tugged from your body, underwear as well. Casey takes these as well from you. You close your eyes, a smile as big as you could ever remember, you then grip the blankets and wait. You hear Casey removing the shorts he had put on. You bring your left knee up along side your body, spreading yourself a little for your partner.

Casey kisses you right butt cheek and then the left. Wet licking sucking kisses all across your back side. He kisses up the small of your back then all the way to your neck. His warm soft skin press into yours, his hard cock nestles into your groove.

"Onhhhhhh!" You moan. You grind back into him, tilting your pelvis forward and back to slide his shaft through your cleft.

He moves with you, already taking on a thrusting fucking motion. His finger grip your shoulders powerfully. He whispers. "We need lube baby. I can't do you dry." He kisses your neck and rises up off of you once more, ready to get the necessary lubricant.

Shit! You didn't have any lube! You didn't need any with Allie and... Wait. It hits you. "The gun!" You look back over your shoulder at the tall willowy form of your lover. You admire his beautiful and proudly standing manhood. "Chloe's gun."

It was full of anal lube...Chloe, god bless her.

He gives you a look but was too swept up with passion to ask questions. His eyes scan around the floor and soon spots the semi-realistic looking water pistol. He can't help but giggle at the ridiculousness of it, but he holds his left hand out and points the barrel at his fingers. His right hand pumps the trigger and out oozes the thick pinkish lube.

He first grabs his cock and strokes it a few time, coating it shiny. He pumps some more...the presses two fingers against your entrance.

"Ohhhhh! Ohhhhh!" You sigh.

"Jesse baby, you look so hot. Oh my god." He says as you feel on digit slide into you. He pushes his middle finger deep inside of you.

"OHHHHHH FUCK!" You groan. You had been expecting...something. Pain, a pinching, an awkward discomfort. But it felt...FUCKING AMAZING!!! "Ohhhhhhh yes!"

He strokes his cock while fingering your asshole. "Jesse, you feel so good."

You clench your sphincter around his finger as it slides in and out. "Ohhhhhh!" You look back over your shoulder in the grips of your lust. "Fuck me Casey. Fuck me my love!"

He slips his finger from you and bites down on his bottom lip then positions himself in behind you, lining up. You spread yourself for him even more. You feel him make contact.

You hold your breath...

...the pressure increases...he was pushing into you...

...you are so still...your air caught in your chest...

...and finally, mercifully, you feel him slide into you and fill you far better than his finger ever could.

It was heaven. You feel him push his body into your ass cheeks as he goes his full depth.

"Oh my god! Oh my god! Casey...you feel incredible!"

"You too." He says breathily. "Ohh wow babe."

Once more he lays his weight down onto you, and oh how you welcome it. He felt so fucking good on top of you. You felt safe under him, loved and cared for. He lies his stomach and chest over your back. His arms blanket over yours. His hands grip over the back of yours, your fingers interlocking together. His thighs press down into your hamstrings. And as his weight settles down on you, so to does his dick delve deep into you. Your own diamond hard erection strains at the euphoric anal penetration.

"Fuck." You grunt. "Oh fuck...fuck...fuck that feels so fucking good!"

By god it was true. Was this normal? Was it supposed to feel this good the first time? It didn't matter, you were just glad it did.

As Casey begins thrusting his hips, plunging is cock in and out of you, your whole body lights up. Warm tingling waves emanate out from your anus and run all the way out to your extremities. Your every nerve was alive and buzzing. You feel his smooth hairless torso rubbing against your back. You feel his warm wet kisses over your shoulder. You feel the pressure of his hands gripping yours. But most of all you feel that incredible cock of his thrusting in and out of you.

"Ohhhhh...ohhhhhh..." You keep moaning. You could hardly do anything else.

"Oh god Jesse. You feel so good. So goooood. Mmmmmmm." He moves with grace and power. In such a dominant position he was able to bring all of his strength and weight to bear. You tilt your ass upwards, welcoming all he had to give you. "Unghhh...yesss Jesse...ohhh god yes... I love you. I love you."

"Unhhhhh...unhhhhhh..." Your voice is soft yet urgent. "I love you baby. Ohhhh Casey yessss. I love you!"

Feeling your man moving inside of you was every bit as delightful as it was to fuck her.

You moan and moan, uncontrollably so. The feelings radiating out from your ass were intensifying. It was unlike anything you had ever felt before. "Unhhhhh..unhhhhhh..unhhhhhhh..god...unhhhhhhh!" The way Casey drove straight down into was hitting ALL the right places. "Unhhhh..unnhhhhhhh!"

You grip the covers as Casey picks up the pace. Pulling up then slamming back down into you harder and harder. You flesh claps together in a steady rhythm.

Clap, clap, clap, clap. "Unhhhhh..unhhhhhh!"

Your moans rise. Oh god...something was happening! Those warm tinglies that spread from your ass were now concentrating and escalating. Your entire groin area was aglow with a rapidly building...pressure was the only way to describe it. "UNHHH...UNHHHH...ohhhhh fuck...yes...yes....yesss...." You hear your own voice calling out.

Casey props up and pins your shoulders down with his hands and fucks you harder and deeper. His iron rod pounding into your ass in fast powerful thrusts.

Clap, clap, clap, clap. "UNHHHHHHH!"

Casey speaks to you. "That's it baby, ugnh, god that's it."

Your head is swimming in a cloud of bliss. This new unfamiliar yet mind blowing pressure was building and building to heights you could not believe. You felt like you were about to burst! You were about to cum! Your stomach is wet with your precum but it wasn't your cock that was about to nut.

"UNGHHHH OH MY GODDD!!!" You cry. "FUCK, YES, FUCK MEEEEEE!"

Clap, clap, clap, clap. Casey's body slams down into you, his huffing breath blowing against your hair.

All at once...that pressure that had built up to dizzying levels...RELEASES!!!

Your entire being is gripped by the power of this anal orgasm. You shake and buck and momentarily lose awareness of your surroundings. You are lost in rapturous orgasmic sensations sweeping through your whole body but also localized in a white hot point of pure distilled pleasure, a point just within your anus.

"AUHHHHHHHH!!!" You howl a deep guttural primal howl followed by a long rumbling masculine growl. "GUNHHRRRRRRR!"

Casey's high sweet voice was rising on each hard penetration as she neared her own finish. "Ahh..ahhh..ahhhhhhh...ahhhhhh!"

CLAP! CLAP! CLAP! CLAP!

Your toes curl, your jaw clenches, your eyes roll back in your head, and your cock quivers and flexes with all its might as your climax goes on and on and on!

"GUHHHHHHH!"

"Ahhh...Ahhhh...Ahhhhh!" Casey motions were fast, ****, instinctual. "Ahhhhh............AUOHHHHHHHHHHHHH!!!"

Casey slams home and he erupts inside of you. Your quivering insides are painted a warm gooey white by Casey's throbbing cock. Casey's fingers grip and rake down your naked back then grab your hips so that he could pull into you even deeper as he blew his load. You push your ass up onto him with equal aplomb.

You had just come down from your heights so you smile and hum happily as you feel and listen to Casey sigh and moan and buck his way through his. You look back to him. His fair skin was aglow with a sheen of sex sweat, his exquisite face was a mask of pure sensual joy. Fuck...he is so beautiful.

He slowly opens his eyes and looks at you as his release comes to its conclusion. "Ohhhhhh wow." He smiles.

"Come here you sexy man." You grin.

He slips out of you, causing you both to let out a happy little. "Oooo!"

Sliding down beside you he takes you in his arms. You turn toward him and return the embrace. You kiss, you gaze into each other, you smile like the silly love struck boys that you were.

"I love you."

"I love you."

"I love you."

"I love you."

You trade the words back and forth. Giggling, ticking, caressing, kissing, bonding, all the way along.