Shameless

Alex didn’t remember how it started, not exactly. All he knew was that it had been a drunken night that spiralled out of control. He couldn’t get the feel of the lace against his cock out of his mind after that night. It had been exhilarating, similar to the first time he’d masturbated. Weeks later he was still waking up from wet dreams thinking about the lace panties on him. It wasn’t even someone else wearing them. It was always him wearing them.
As time progressed, Alex became less worried about the dreams and more intrigued. He began researching men’s lingerie, which only progressed his dreams further. Now not only was he dreaming about wearing panties, he was dreaming about garter belts and thigh highs and hell, even heels.
Then, to make matters worse, the dreams moved from his slumber to the waking hours of the day. He started noticing women in heels, not for their beauty but for the beauty of the shoe. He couldn’t get himself off anymore without thinking about it. About being fully clad in lace, looking like a whore.
After months of dealing with this, he finally caved. He went to a website he’d found during his researching and almost bought out the store. It was his guiltiest purchase he’d ever made, and yet he checked the tracking information obsessively.
The day it was to arrive, Alex took a big leap and completely shaved his lower half. It was a weird feeling, but his stockings would catch on the hair otherwise. He had to wank one out to the thought of that.
Alex was more than thrilled when the order arrived at his door step. He immediately went to his room to unpack everything. It took a few minutes to chose which set to try on first. He ended up choosing the pink and black tartan outfit. It was a bra, which he’d bought stuffers for, and a garter skirt of the same material.
Alex paired it with black fishnet thigh-highs to clip to the garter skirt and a sexy plair of black and white heels. When he looked at himself in the mirror, he let out a moan. God he looked so good. He felt good too.
Alex bit his lip, glancing at his bed, it was covered in his new purchase so there was no where to lay down to properly enjoy his attire so he snagged some lube and a dildo out of his bed side drawer and wobbled into the living room. He grabbed a blanket from the couch and laid it down in the center of the room.
After setting the lube and dildo down on the blanket, Alex carefully lowers himself onto his back, his knees spread and his heels digging into the floor. He was inadvertently facing the door. He reached down and began to stroke himself dry, just to get himself fully aroused.
Once Alex was rock hard, he opened the lube and coated a few fingers. He began to tease himself open, being extra playful. He wanted to draw this out for as long as he could. He worked himself with only one finger until he absolutely couldn’t take it anymore and he pushed in a second one.
Alex scissors his fingers, stretching himself further. The dildo he’d chosen was thick. That’s how he liked it. The bigger the better. He presses his fingers deeper to tease his prostate, moaning out and writhing on the floor. He debates on whether or not to take a third or go straight for the dildo. He decided on the dildo, wanting to feel the stretch burn of it’s girth.
Alex slips his fingers out and coats the dildo in lube. He bites his lip as he presses the blunt head against his barely stretched hole. It takes a bit of coaxing before the head pops in. He lets out a moan and works the dildo the rest of the way into himself. When it bottoms out, he has to pinch the base of his cock to sway his orgasm.
Once he’s away from the edge once more, he begins fucking himself with deep, slow thrusts. He never once stopped moaning. He slowly builds up speed with the toy, fucking himself harder and faster with every thrust.
Alex forced himself to the edge and then stopped moving, letting himself dwindle before he started again. He brought himself to the edge 4 times, the time between each pause getting rapidly smaller.
In all of the excitement of the day, Alex had completely forgotten that he’d invited Jack over to watch the game. Unaware of what he was walking into, Jack arrived at Alex’s house 15 minutes before the game was supposed to start with a case of beer. He walks in the front door without knock, assuming Alex was expecting him.
Alex is moaning loudly as the front door opens, completely missing the sound. Jack froze halfway through the door. He almost dropped the case of beer in the process. Luckily he didn’t and after a few blinks and a couple seconds to fully process what was happening, Jack stepped all the way into the house. He closed the door behind him and set down the case of beer.
Alex was still oblivious to his visitor and Jack took note of that. He took note of everything that was happening. From the size of the dildo to way Alex’s flushed face matched the pink of the little outfit he was wearing. God, the outfit. It was everything Jack had ever dreamed of to see on a girl. Now that it was there, being worn by his best friend, fuck he was a goner.
Jack easily became mesmerized by the movement of the dildo in and out of Alex. The singer clearly liked it rough and hard. Jack liked rough and hard too. His jeans were getting a bit tight in the front so he, unthinkingly, reaches down to open them. He palms himself through the fabric of his boxers.
Alex edges again, panting heavily as he stops moving. By some miracle he decided to open his eyes in that moment and the first thing his eyes focused to was Jack palming himself. Alex groans, throwing an arm over his eyes. He’d forgotten about the game. Well this would be awkward to explain. Not that it was the first time Jack had walked in on him using a dildo, but the lingerie was new.
Jack blushed when he made eye contact with Alex. He’d fucked up. He shouldn’t have stayed. When he opened the door he should have backed away and left. But now here he stood with a hardon from watching.
Alex straightens his legs out and sits up, moaning softly when the dildo is pushed deeper into him. He has to take a deep breath before he can speak even semi-normally. “I have a pantie kink and these came in the mail today. Forgot about the game... I, fuck I’ll go change if you even want to stay for the game.”
Jack’s eyes flash to him. “What?” He was slow on comprehending the words. “Oh, um, I can leave if you want... You probably don’t want to sit through an entire game with blue balls.” He says, his eyes getting stuck on the bra and Alex’s angry red cock. He looked so ready to cum.
Alex bites his lip. “Uh, I could um, go finish and change and we could still watch the game?” He mumbles.
“No!” Jack says, not liking the idea of Alex changing out of that outfit. “Uh, um, you don’t have to go or change...”
Alex looks at him for a bit, trying to see if he was serious. But judging by the bulge in his pants, he seemed pretty serious. He lays back down and gets back into the position he’d been in earlier. “Are you just going to watch or are you going to come participate?”
Jack stood there for a moment, staring blankly at Alex before he dropped his pants and pulled off his shirt. He reached back to lock the front door before joining Alex on the blanket. He settled on his knees between Alex’s legs, running his hands along the lines of the lingerie and Alex’s body. He moans quietly and leans down to nibble on Alex’s hips.
Alex moans, sliding his clean hand into Jack’s hair. Jack continues to nibble and kiss around his body, teasing him. It was like hell. He was already so close and now Jack was being a tease.
Jack could tell he was close by how his balls were so tight against his body. He grins and slowly removes the dildo and sets it to the side. He grins up at Alex. “I’m going to fuck you.” He purrs, nuzzling the fabric of the skirt.
Alex moans and lifts his hips, pushing the lube into Jack’s hand. Jack’s cock was far bigger than the dildo he’d just been using and the few times that Alex had seen it hard had made him drool. It was everything a size queen like Alex dreamed about. And it was going to fuck right now, while he wore lingerie. Today couldn’t get better.
Jack smirks at the response and takes his time lubing himself. He rubs the rest of the lube left on his fingers onto Alex’s hole before laying over Alex. He lines himself up, pressing just the head in. He grins at Alex. “Hey sexy.” He whispers.
Alex blushes at him, clenching around his head. “Talk later, fuck now. Please.” He whimpers. Just the head was thicker than anything Alex had taken and it was glorious. He wanted to feel all of it.
Jack grabs Alex’s hips and thrusts into him, watching Alex’s face. He’d had issues in the past with people not enjoying the size. Which sucked, really, because then he ended up with sloppy pity handjobs or half a blow job.
Alex took all of him like a champ, moaning out Jack’s name loudly. “Please, fuck Jack, more. Please.” He pleads, squeezing eyes shut at the burn. He felt like he was on fire, his entire body tingled.
Jack was a bit surprised at the response he got. No one ever begged for his cock. No one. He speeds up this thrusts, fucking Alex hard and fast. He leans down to purr in Alex’s ear. “Is this what you like, Lexy? A thick cock splitting you in half while you wear fucking thigh highs?”
Jack sits up a bit and changes the angle. He switches to dirty grins against Alex’s prostate. Which was making gorgeous, gorgeous sounds come out of the singers mouth.
Alex begged and pleaded and moaned as he was impaled with the monster cock. He was on the verge of coming already since he’d been edging prior. Which was rather disappointing because all he wanted was for Jack to pound him into a daze. Maybe he’d get a second round. The thought of that sent him over the edge and he was coming all over his own chest.
Jack fucks him through it, gripping his hips tightly as Alex’s tight hole pulses around him. He moves to pull out once Alex is threw his orgasm but alex’s legs wrap around his waist. The heels of Alex’s shoes push into the small of Jack’s back, effectively keeping him there.
“Keep going. Fuck me as long as you want.” Alex pleads. He wanted to be used. He wanted to be bred.
Jack yet again searches his face for any hint of a lie but all he finds is desperation and arousal so he starts thrusting into him again. Now he was searching for his own orgasm, using the position that pleasured him the most. His hips snapped forcefully against Alex’s ass, the sound of flesh hitting flesh mixed in with the sound of Alex’s moans.
Jack fucks him long and hard, long enough for Alex to get hard again. Alex hadn’t realized before how much he actually loved being used. Jack wasn’t even paying attention to his cock, which made it harder. He reaches down to take care of himself, wondering what he’d done to deserve this glorious day.
Jack was in a zone. He almost forgot he was fucking a real person and not the fleshlite he used at home. But it was so much better, the moans, the warmth, the pain of the heels digging into his back. God it was perfect. He’d do anything to feel this again. He didn’t even feel the build up of his orgasm, it just came. It hit him like a wall and he was suddenly filling Alex.
The unexpected feeling of Jack’s cum filling him threw Alex over the cliff too. Alex’s muscles convulsed around Jack, drawing his orgasm out longer. Jack has to catch himself on his forearms before he crushes Alex underneath him. They lay there for a few minutes, a panting mess before Jack slowly starts kissing along Alex’s neck.
“That was so good Lex.” Jack murmurs, nuzzling him. “Fuck, you’re the first person to take it all.”
Alex hums happily. “Who wouldn’t want all of that. It’s the perfect size.” He murmurs, rubbing Jack’s back. He’d scratched it up pretty bad during sex.
Jack hums softly at that, nibbling his jaw. “You look so sexy in thigh highs, fuck. They’re my favorite thing.” He whispers.
Alex grins. “I happen to have 4 more pair to try on... I’ll happily give you a little fashion show if you’re willing to share that gorgeous cock with me again.” He purrs.
“I’ll fuck you as hard and as many times as you want if I keep getting to see you like this.” Jack promises.
Alex smirks and struggles to sit up. “Deal.” He murmurs, kissing Jack hotly. The football game completely forgotten.