Another straight first time story taken from a fantasy I had at one of my Halloween parties. I hope you enjoy my little Halloween party fantasy.
“How are you going in those heels mate?” Bobby asked as Yani walked past him to get another drink.
“About as well as you’re going in that corset I’d say,” Yani laughed. His annual Halloween party had yet again resulted in several his mates presenting themselves in rather sexy costumes.
“Blokes aren’t meant to wear either of them.” Bobby shifted the bodice of his outfit in an effort to get more comfortable. “And I can see why chicks never liked wearing them either.”
Yani and his partner had the house for a party. A big open-plan entertaining area. A big backyard. A patio off the side of the house. They had hosted many parties and their Halloween party had almost become a tradition for a lot of their friends. A few years back the theme had been “Sexy Halloween” after Yani had realised just how many ‘sexy’ costumes were in stores. ‘Sexy Nurse’ of course, ‘Sexy Fireman’ too. But he had laughed at ‘Sexy Vampire’ and ‘Sexy Frankenstein’. That year had resulted in some hilarious takes on sexy versions of things and had resulted in a few entries to the spank bank for Yani.
Since then, the theme hadn’t necessarily been specified but there was always a healthy dose of ‘sexy’ costumes. The relaxed atmosphere of the party and their friendship group meant that even their straight friends felt comfortable dressing up and showing a little skin.
Like tonight, Bobby was dressed as Frank N Furter from Rocky Horror. Yani was grateful for the amount of leg Bobby was showing, the way his lean torso was held in place by the corset and the fact that he either didn’t realise or didn’t care about how prominent the bulge of his junk was in the skimpy underwear of the outfit.
Yani himself was dressed as Sharon Stone from Basic Instinct, hence the heels. He wasn’t showing quite as much leg and was, in order to remain in character, had suppressed his bulge.
Yani grabbed two drinks from the fridge and handed one to Bobby. Bobby responded by twiddling his fingers. Yani noticed that Bobby was holding the little pouch he had arrived with. Yani smiled knowingly. It had been far too long since he had had a smoke with Bobby. Without exchanging words, they both walked out onto the patio.
“You know what’s worse than the heels?” Yani asked as he opened his can.
Bobby took a sip from his drink before replying. “What?”
“Hiding my dick in this dress!” Yani took the opportunity, away from the bulk of the partygoers to make a slight adjustment to his package.
“You’re telling me! I am jam-packed in here!”
“Oh really? I didn’t notice.” Yani’s sarcasm was obvious and Bobby smiled in response. “I thought you just picked the costume to make sure everyone knew you were blessed mate.”
“Fuck. Of course you noticed.” Bobby was fully aware of Yani’s wandering eye, but Yani knew he didn’t mind.
Yani just shrugged in response and took another long sip of his drink. Bobby put his pouch on the table and pulled out one of the pre-rolled joints inside. Bobby had so much more experience than Yani and Yani was always impressed by how well-prepared he was.
“Been a while, eh?” Bobby said.
“Yeah. I’ve been meaning to invite you over. But you seemed busy with Kate.”
“Ah well. She’s out the way man. More bro time ahead.”
“Am I sad for you?” Yani knew most of Bobby’s dating history. Most of his relationships fell short of what anyone would consider serious.
“Nah mate. Like I said, more bro time.” Bobby lit the joint, took a deep puff and handed it to Yani.
The boys stood quietly for a while, alternating between sips of their drinks and long drags. They both quickly relaxed even further.
“Bro, no one’s out here.” Bobby restarted the conversation. “Mind if I give it a bit of air?”
Yani just looked at him, cocked his head and raised his eyebrows.
“I know. I know. But I thought I’d be polite anyway.” Bobby laughed and turned his back towards the door.
Yani made no effort to look away. In fact, he took the opportunity to reposition himself to get a better view. He knew now that Bobby didn’t care and, while Bobby fiddled with the clasp that attached his corset to his briefs he was suitably distracted as to be unaware of Yani’s movements.
Bobby hooked his thumbs into his waistband and slid the front of his costume down. Yani watched in awe as a thick, dark piece of cut meat flopped out. Bobby’s skin was dark, but his cock was another shade darker. It hung over the waistband before Bobby lowered the costume further and his plump balls popped out as well. These were just as impressive as his dick, large and full and surprisingly smooth. Yani looked again and realised the whole area was smooth.
“You shave it all?” Yani asked, unable to stop himself from commenting.
“Yeah. I had an ex who liked it smooth. I kinda got used to it.” Bobby shrugged.
The boys were quiet for a moment as they finished off the joint between them. Yani was unsure of what to make of the situation. Bobby was an ex-professional athlete, with a string of hot women in his past. Right now though, he was standing in front of him in fishnet stockings, a corset and a wig, with his massive dick just hanging out on show. Yani wasn’t sure if it was impolite to look, but he couldn’t stop himself from glancing down. After a while he figured that Bobby wasn’t hiding it, so it was fair game. He started to imagine what that thing would look like hard and what it would do to the various girls he had been with over the years. Before long, he had to fight to keep his hands on his beer bottle.
“How about you bud? You said you were all tucked away up there. Let him breathe mate,” Bobby’s suggestion snapped Yani back to reality.
“Um, if I let it out now it’s gonna be pretty obvious.” Yani realised that his fantasies had already resulted in some developments in his own briefs.
Bobby looked confused for a moment before smiling. “Taking up a little more room, eh?”
“Yeah.” Yani blushed.
“All good man. We’re buds. And it’s not like I haven’t seen another dude’s boner before.”
Yani shrugged and reached up under the dress that was his costume. He grabbed the waistband of his briefs and pulled them down, freeing his semi erect cock. He placed the briefs on the seat next to him and picked up his beer again.
“Better?”
“Much.” Yani looked down at himself and saw that his bulge was already prominent. He shifted his legs a little, hoping that it would be less noticeable. He was sure that Bobby was not going to be comfortable with the physical response to Yani’s interest.
“Semi?”
“Yeah.” Yani turned slightly away.
“Relax dude. I don’t care.” Bobby’s cock twitched slightly and Yani noticed that it was slightly plumper than before.
The sliding door interrupted their conversation and Yani turned his head over his shoulder to see his husband standing at the door.
“We’re all going to fire up the karaoke. You in?” he asked.
“Oh yeah. Just gonna finish up this with Bobby OK?” Yani replied.
His husband smiled. “Of course, babe.” He stepped back inside and closed the door. Soon after, the sound of the first karaoke song came thumping through the walls.
“Everyone’s on the microphone, eh?” Bobby asked.
“Yeah, I reckon.” Yani looked down and could have sworn Bobby’s dick had grown a little more.
“Bud. I’ve been meaning to ask you something.”
“Yeah?”
“I don’t know how to put it…”
“What is it man? Just spit it out.” Yani had let his own cock grow to full size now and he was sure it was making an obvious tent in the white flowing fabric.
“Wanna jerk me off?” Bobby asked, spitting the words out quickly.
Yani froze. That was so far from what he thought Bobby would ask that he didn’t know how to respond.
“Fuck. I shouldn’t have asked bro. It’s weird, eh?”
Yani knew he needed to respond quickly. Bobby was reaching for the waistband.
“No no. Not at all. Just unexpected.” Yani took a small step forward, placing his hand on top of Bobby’s to halt his progress.
“I just, like, know some guys who have gay buddies and like, they don’t mind helping them out.”
“Bro. I got you.”
“Yeah?”
“Yeah.”
Bobby put his hands back down by his sides. His cock twitched and grew a little more.
“You mean now?” Yani asked.
“If you want.”
Yani reached out and took Bobby’s growing cock in his hand. He wanted to and had wanted to for a long time. He quickly started stroking it, encouraging it to its full length.
“Make it quick.” Yani said. “I wanna sing soon.”
Bobby laughed softly. “Sure thing bud. I can’t keep you from the microphone, I know that.”
Bobby’s cock was now fully hard in Yani’s hand, he estimated it was close to 9″ of thick, cut meat. He stroked quickly, a little disappointed that he wasn’t going to be able to take the time to savour it. But for obvious reasons, such as the rest of the party going on just inside, he knew he had to be quick.
“Oh fuck. That’s good.” Bobby moaned softly.
“It’s not my first.” Yani grinned, his own cock pushing harder against the dress fabric now.
“You can if you want.” Bobby nodded at Yani’s erection.
“You first.” Yani reached his other hand over and cupped Bobby’s balls. This would just about be the biggest package Yani had ever handled, and he had handled plenty.
“Oh yeah. That’s it.”
Bobby’s cock throbbed in Yani’s hand and he started breathing more heavily. Yani looked down and saw that Bobby’s cock was leaking steadily. He shifted his hand and took some of the precum in his fingers, using it to lubricate Bobby’s mushroom head before resuming his fast-paced stroking.
Bobby moaned a little before quieting himself and chuckling. Both boys knew that they couldn’t give themselves away.
“Fuck Yani. Make it real wet and then pull my balls.”
Bobby was a man that knew what he wanted. Yani liked that. He slid his fingers over Bobby’s slit and collected some more precum. He gripped the smooth balls in his hand and pulled down. Another dose of precum fell from Bobby’s cock onto Yani’s waiting fingers and he used it to run his palm over the head.
“Yes! Shit!” Bobby was struggling to keep himself quiet.
Yani knew what would finish him off. With a slick fist he pumped the top of Bobby’s cock, focusing on the swollen head. He pulled down again on Bobby’s hanging balls, twisting them just enough so that Bobby could feel an extra tug.
“Oh. I’m gonna-” Bobby’s eyes darted around and then his hand reached out. He grabbed Yani’s briefs from the chair in front of him and put them just beneath his cock just in time.
Yani felt Bobby’s dick throb in his hand. Bobby raised himself up onto his toes, tensed his legs and grunted softly. The first shot of cum fired from his cock, missing the waiting fabric completely and landing on the concrete floor. Bobby repositioned for the next shot and with another grunt he fired into Yani’s briefs. Bobby’s panting and gasping continued as the pleasure coursed through his body. His cock continued to spew forth his seed until the last of it dribbled from his dick onto the soaked underwear.
“Holy shit man. That was good.” Bobby sighed and placed a hand on Yani’s shoulder to steady himself.
“I could tell. You ruined my briefs man.”
Bobby laughed. “That’s my way of saying thank you mate. You can keep ’em”
Bobby winked and slid his wilting cock back into his own costume. Yani’s cock was still achingly hard and he didn’t know what he was going to do about it.
“You need to sort yourself out?” Bobby asked.
“I might head into the bedroom to do that man.” Yani was suddenly self-conscious about jerking his own 5″ in front of well-hung buddy. “Head in first and distract hubby for a few minutes so I can get it done?”
“Sure mate. And thanks again. I fucking needed that.”
“Any time.”
“I’ll hold you to that.” Bobby turned and walked back into the house.
Yani took a moment to compose himself as he heard Bobby ask his husband for a duet as the next karaoke number. He smiled to himself as he reached under his dress. He knew he wasn’t going to make it to the bedroom. He lifted his dress at the front, just enough to gain access to his dick.
With it now exposed he wrapped his soiled underwear around his demanding shaft. He felt the slickness of Bobby’s load and started to stroke. The wetness of his own precum, mixed with Bobby’s seed sent ripples of pleasure through his body and he soon felt the tingles of his orgasm approaching.
He worked his dick furiously, sliding his skin over the head of his uncut cock, encouraging his looming climax. He tensed his legs, closed his eyes and pictured Bobby’s dick, pulsing the load into the briefs that were now about to be soiled again. That image was enough to send him over the edge.
With a grunt and moan that he could barely hold back Yani’s cock exploded. He quickly moved the briefs over the end of his dick, catching the load and ensuring it mixed with his buddy’s. His legs shook with pleasure, and he reached out and braced himself on the table beside him. His body shuddered and he choked out a gasp as wave after wave of pleasure racked his body. His cock throbbed as he fired his load, flooding his briefs with even more cum.
As his orgasm concluded he held his cock still, enjoying the feeling of the wetness around his cock. Knowing that this was as close as he was ever going to get to his pro-athlete stud of a friend.
Yani signed and let the last aftershock of his climax run through his body. He slid the briefs off his cock and dropped his dress. After taking the last sip from his drink he turned to the door. Sliding it open he was hit with the wall of sound that he knew was his husband’s favourite song. Bobby had really come through with the distraction.
Yani walked quickly to the bedroom, holding the pair of briefs by his side, the blind side where no one in the main room could see.
In the bedroom he grabbed another pair of briefs from his drawer, sliding them up under his dress to hold his cock back in its concealed position. Before returning to the party, he quickly reached under the bed, finding a small white box. Yani opened it and placed the soaking briefs inside, on top of the other pairs of stolen and soiled underwear he had collected through the year. This was now the pride of his collection.
I hope you enjoyed this straight first time story. Let me know what you think in the comments. Share the story and the podcast with your friends so they get to enjoy it as well.
If you like this story, check out Mouth Away From Home for another straight first time situation.