Adventures In Wearables Ch. 01

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A birthday wish for pegging takes an interesting turn.
11.3k words
4.83
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88

Part 1 of the 5 part series

Updated 11/24/2023
Created 07/10/2023
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This story is a little different than the first story I published. It's more of a classic story common to this platform with multiple chapters that don't share a continuous timeline.

I always appreciate your feedback to let me know if you like what I'm writing. As well as any ideas you may have for future chapters. I have a few segments already written that just need to be edited. If you don't like the story, please don't just leave me with one or two stars, without your feedback I can't improve. Thanks for reading!

All characters in this story that engage in any kind of sexual activity are consenting and over the age of 18. If you don't enjoy stories where the characters end up with genitalia or a body parts that generally belong to the opposite sex and then enjoy using it, this probably isn't for you. All characters are fictional, we just wish this could actually happen.

Mac's Birthday

Piper rushed to get her errands finished. Her husband Mackenzie's (Mac's) birthday party was supposed to start in 40 minutes, and she still had three stops to go. She had the beer, the booze, and plenty of food ready on trays in the garage refrigerator at home. The only saving grace to how late she was running was that a few of his buddies had taken him out golfing today.

Mac wasn't great at golf. So, when he and the guys went "golfing" it meant going to a fancy driving range and having a few beers while Mac's buddies tried to pick up the waitress after three beers and Mac laughed awkwardly at their lame attempts. It was still fun for Mac, but his buddies usually had more fun. Normally, they ran long when they went, depending on who ordered an extra pitcher with ten minutes left on their bay.

Piper had stopped at the cake place on the other side of town, she picked up Mac's favorite cake, Boston creme pie, and a few macrons for the wives that wanted something sweet but not a whole piece. She ran quickly into a big box store for fancy looking plastic plates and cutlery and started driving home. She had just 10 minutes left until their guests might start arriving, when she realized she had forgotten candles. Pulling over she searched for the first thing the popped into her mind. Party favors. The search offered 5 options, the closest only 3 minutes out of her way. She pressed go on her phone and followed the directions to a small strip mall that didn't look like it had been updated since the 1990s.

Walking into the store that declared PARTY!! in faded multi color letters on the sign above the door, she was greeted by two clown mannequins holding fake balloons. The store was brightly lit, and had all things party, tiki party aisle 1, costume party's aisle two, weddings aisle three. It was clean with old floors that had seen hundreds of thousands of feet up and down its aisles.

Wandering the aisles, she finally found a section declared "Cake and ice cream!" It was mostly plastic flatware, cake toppers, candy decorations, and a few bachelor/bachelorette themed cake toppers. The candle section was pretty bare. Most of the candles were large numbers with cartoon characters on the boxes with, insert popular children's character here, "party with your favorite character!" the boxes declared. No normal candles caught her eye. Looking around again she noticed a small box high on a hook. One last box of "Wishing candles!", Grabbing a nearby jumbo box of paper plates to boost her 5'5" frame she could just reach the box. Getting down and putting the box of plates back on the shelf she walked to the front. A bored looking clerk in a vaguely circus themed shirt waited for her.

Piper paid without looking at the total and thanked the cashier, who if anything, looked even more bored during the sale, and walked out to her car. She was going to have to rush home and was still going to be 20 minutes late.

Pulling into her garage she could see a few of their friends' cars in the street and her husband's car was already back in the driveway. Thankful that Mac had wrapped up early enough to beat her home, she brought in her purchases and started setting out the food. Mac was outside in the back yard talking to the folks that had already arrived. He had obviously broken into the booze because almost everyone had a beer or seltzer in their hands.

Piper quickly set out the food around the kitchen Island, placing the plates closest to the door. She grabbed the candles still wrapped in the receipt and placed them on top of the cake box and went to put it in the fridge. As she walked to the fridge, she noticed the price. She hadn't even looked at it when checking out. $75.89 jumped out at her.

"What a rip-off," She muttered. "No wonder no one was in the store, their prices were crazy!"

"Nothing to do about it now, those candles had better be something amazing..." she thought.

Grabbing a seltzer she walked outside, declared the food ready and gave Mac a kiss.

The party went well, the guests had fun, ate most of the food and played a few yard games. One group of guys who had been "golfing" with Mac, were joking loudly about birthday sex. A few elaborating on some requests they'd made from their wives or partners.

One declared that he gotten a BJ for each decade he had been alive, another, sex on the hood of the car, a third a threesome. Piper privately doubted the last brag was true, unless it was a MMF.

The conversation faded as she walked away from the guys towards some lawn games. Piper had stopped listening right after they started talking about it. She knew what Mac would ask for. The strap-on.

He would sweetly ask, "Honey do you think you could fuck ME tonight?" and she would say "of course!" And he would say "I mean with the strap-on."

She would give him a look and give in, "Ok, but only because it's your birthday." She would go through the motions but really never enjoyed the act. She felt like it was a little unmanly to want something phallic in that hole.

Mac had assured her it wasn't unmanly at all. If anything, it was more manly to acknowledge what made him feel good and be willing to ask for it. She still felt that taking it up the ass was well, a bit sissy. But she did it for him anyway. Mac never came when she did it, but assured her it felt really good and usually finished inside her after the harness was off. He did all the work, putting on the harness, cleaning the dildo etc. It just wasn't her thing.

The night went on and the boys started to push booze on Mac, figuring it was his birthday he let them give him a few more than he would normally drink. Piper asked him to round up the guests for cake and singing so he boisterously brought everyone inside. Mac had also heard the guys joking about birthday sex. He knew that like most years since they had gotten married it was his best chance to have Piper peg him. He hoped this year would be better than last, it was a struggle to get her to do it and he felt a little bad asking her to do something that she seemed to loathe.

Piper pulled the cake out and placed the candles on the cake, there were only six in the small box. Lighting them she carefully moved the cake to the island in front of Mac. Someone started to hum. Piper started to sing. "Happy birthday to..."

The words after the first few were almost unintelligible as people joined in and all sang at different speeds. When the song was finished someone yelled "Make a wish!"

Mac paused before he blew out the candles. What should he wish for? A new car? A lottery win? Mulling it over he decided to wish that Piper would peg him tonight and really get off on it for once. Taking a big breath, He imagined her moaning behind him as she thrust.

The candles went out easily. No stragglers. Some people started clapping. Someone asked, "What did you wish for?" Mac looked down he wasn't going to answer.

He just smiled and said "It's a secret..."

"Ohhhhh..." said someone out of Piper's range of view.

One of the boys pulled out a bottle of something godawful and potent they must have brought with them and yelled "birthday shots!" and produced a sleeve of plastic shot glasses and started pouring. Piper had watched Mac think about his wish. While he was blowing out the candles, she wished that she could relax and actually enjoy sex tonight and not dread putting on that strap on again. Maybe he would just want a quicky and fall asleep instead.

The birthday shots and cake slices were passed out. Piper saved the candles and put them back in the box. She was going to use them every chance she got now that she couldn't return them. A shot ended up in front of her. Mac had already been goaded into taking a second shot by the boys. She pushed it his way. He gave her a look, nodded and dutifully took one for the team. The rest of the night passed quickly, several guests getting ride shares leaving their cars parked on the street. By 10 pm everyone was gone. Piper and Mac slumped on the sofa. Cleanup was going to wait till tomorrow.

Mac reached over to put his hand on her leg and gave it a squeeze. "Thanks for the great birthday honey." He looked up at her, he was more than a little drunk. "You want to fool around?"

Piper looked down at his hand, "Sure Hun. What do you have in mind?" She was still hoping for a quickie and then bed. "

You know..." he drawled, "Fuck me..."

Piper sighed. "Ok, but just because it's your birthday."

She stood up to go upstairs. He followed, trying to grab her butt as she walked. He missed as she easily skipped out of the way of his inebriated swat. As they walked into the bedroom, Mac started to take off his clothes, Piper went to the bathroom to wash her face. When she walked out Mac had pulled out his medium dildo, the one with the veins, the harness, and some lube.

He walked to the bathroom, "I'm gonna pee and then I'll help you put it on, ok?"

She watched him walk naked into the bathroom. At 32 he was still quite muscular, 5'10" and 175 he hadn't gotten the beer belly his friends had been nursing since college. His semi hard penis bounced up and down as he walked. He'd chosen a dido smaller than his own 6.5 inches tonight, she knew he had larger ones, she was surprised he hadn't set one of those out, as he seemed to like them larger than his own dick.

After he closed the door to the bathroom. She pulled off her shirt and shrugged out of her bra and looked at her reflection in the mirror on the back of the closet door. Cute face with a smattering of freckles, shoulder blade length dark brunette hair pulled into a low pony, her full breasts had just a little sag and looked a tiny bit large on her frame. Her light brown nipples hardened as the air crossed them. "Not bad for 30" she thought. She pulled down her jeans and panties in one go letting them pool at her feet, she twisted and looked at her ass.

"Still nice and firm" she thought. It had better be, she worked hard to keep her figure. Looking at her front profile, her generous hourglass figure with full hips, soft belly, and toned thighs highlighted her thin landing strip pointing at her vulva and a tiny gap below her lips as her thighs came together. She imagined what she would look like in a moment, straps around her waist and legs, pink dildo jutting out and down from above her mound.

"Uh, I'd rather have a dick than wear that dildo" she thought.

Mac came back out, picking up the harness, he inserted the dildo in the front ring he offered it to Piper. She walked over and he helped her into it. His dick, now almost completely hard, drew a line of precum across her thigh as he reached around to clip the back of the harness, the dildo poking into his thigh.

He was struggled with the straps, she waved him off and said, "Go get ready I'll fix these." He mounted the bed on all fours and arranged a towel under him.

Piper sighed as she adjusted the straps. He was drunk, and she was going to have to fuck him, this might be the least fun she'd ever had wearing a strap-on. Maybe she'd be able to get away with doing it for a few minutes and let him finish in her, at least she would get something out of it. After she finished with the last strap, she turned to look at her reflection again. Just like in her imagination, the dildo pointed out and down marring the view of her strip and vulva.

She sighed and poked the dildo. It bounced and then lifted. To her amazement it started to curve up a little at the tip and change color. The round head flared out to look like the glands of a penis and turned a dark red almost purple. The color change moved down the shaft until it reached the base.

The harness tightened on her body and seemed to sink into her skin. Disappearing as it went. Soon it had vanished and all that was left was a cock sticking out of her, pulsing with each heartbeat. She reached out and poked it again. She felt that! It was soft but firm. She yelped.

Mac looked over, "You ok honey?"

Piper had spun around. "I think I need to pee first hold on!" and she fled to the bathroom slamming the door.

She stood before the mirror. She had a cock. It was veiny, like the dildo had been and about five and an have inches long, a flared pulsing head, and about an inch in diameter at the base. Her landing strip was still there, and she could see smooth skin below the cock. But she couldn't see her pussy lips. She slid her fingers from the base of the cock back toward her perineum, finding only smooth skin all the way back to her rosebud.

Where had her pussy gone? She slowly stroked her new cock, she could feel her fingers grasp it, the heat of it, the blood pulsing inside. It appeared to be circumcised and she squeezed the glans. It pinched a little but felt good. A little drop of precum slid out of the hole at the tip. Piper spun slowly in the mirror eyes on her cock. As she turned all the way around, she noted what looked like a tattoo at the base of her spine right where the clip for the harness had been. She felt for it. As her fingers brushed over it, it rose from her skin. She squeezed the clip open. As the clip opened, straps appeared like magic from her waist and thighs the harness fell forward, the dildo slapping her thigh. She lifted it. Once again it was a lifeless piece of silicone. The only evidence that it had been more was a drop of liquid near the tip.

Quickly feeling for her pussy, she found it. Sighing in relief she pulled her hand back, wet with her moisture. "Wow": she thought, "That was hot..." she found the hanging clip ends and clipped them behind her back. The process happened again, the harness disappeared, and the cock was back, pulsing with each heartbeat.

"Piper?" Mac called, "You, ok?"

"Yeah, I'll be out in a minute leave some lube for me and assume the position."

Mac pulled his probing fingers out of his ass, added a bit more lube to his anus and got back on all fours.

"Mac?" piper said as she exited the bathroom.

"Yeah Babe?"

"Close your eyes?"

"Umm, ok?" Mac started to get more excited. She'd never made that request before. He could hear her walk up and felt when she mounted the bed.

"You ready?"

"Yup! Put it in me!"

"Ok..."

Piper grabbed her cock and shuffled forward placing the tip on his lubed rosebud. The heat felt nice on the tip. She grabbed his hip with one hand and held her cock in place as she pushed forward. It felt amazing as the head of her cock pushed inside. The tightness of his sphincter thrilled her as his ass yielded to her, the walls slippery with lube. The head popped inside. She pushed forward slowly, savoring the new feelings. Soon she was all the way in. Her breathing was heavy, and her cock twitched with anticipation.

Mac felt the tip of the dildo at his entrance. It felt hot, and a little less firm than usual. Piper pushed in slowly, he could hear her breathing speed up. His pulse thudded in his ears. Closing his eyes had made this a lot more intense.

Piper shifted her weight and started thrusting. Slowly at first and then faster, grunting a little with the effort. This was so much better than a strap on. His tight ass hugging her cock on every thrust. Soon he started to push back, their bodies making slapping noises as they came together. Mac started to moan, and Piper reached down to tweak his nipple.

This made him moan again and push back against her harder, encouraging her to go faster. She obliged. Her grunts sharpened and she pistoned in and out, her pleasure climbing. She shifted her weight and started pushing down with each thrust. She heard Mac gasp and he moaned again. His breath was punctuated by her thrusts. Starting to feel a little extra friction Piper grabbed the bottle of lube and squeezed a little into his crack trying to time it with her thrusting not wanting to stop.

Mac was beside himself, he felt like he would come at any second. He rode waves of pleasure that Piper was inflicting on his ass and prostate. Suddenly he tensed, and stopped pushing back, the dam broke. His ass squeezed, and his cock twitched up towards his belly. His legs shook, and his arms gave out. Stream after stream of milky cum shot out of his cock onto the towel, his chest, and face. It slowed but didn't stop as Piper continued to pump him.

He was lost in the feeling, like a warm fire burning in his abdomen, spreading from just behind his dick. He hadn't touched his dick at all. He'd never achieved a hands-free orgasm before. He'd tried, a lot, but this was out of this world. The pleasure continued to spread, turning into tingles as it reached his hands and feet. Mac's dick continued to dribble clear fluid in little spurts as it softened. Piper was still going.

Piper had felt Mac come. Her breasts were bouncing with every thrust. Her nipples hard, thick as AA batteries, they screamed for her to touch them. She held his hips tight leaving nail marks on his skin, thrusting harder. The squeezing and shaking from Mac's ass only spurred her on. She was getting close, she could feel it, a sensation building at the base of her cock. The feelings crested, she felt like her cock was the center of her whole world. Breasts heaving, bouncing in time to her thrusts, grunting with effort and pleasure, she came. She felt hot liquid burn up the length of her cock for the first time. She fired two, three, four spurts into Mac's ass and she was spent. She leaned over Mac pressing her breasts into his back.

"Mac? You, ok?"

Mac gathered his wits; pegging had never been that good before. He was drunk, he knew but that had been amazing, it even felt like Piper had come at the end.

Mac raised his head from the pillow, "Yeah, I'm ok. Better than ok. That was amazing. Best birthday ever."

Piper smiled, "I had fun too, I really got into it." She pulled out and got off the bed. "Go clean up, I'll take care of the dildo."

Mac grabbed the towel and stumbled to the bathroom to clean himself off.

Sitting on the toilet, he could feel the lube seep out of his ass, and he tried to push a little to help it along. He wiped the cum from his face and chest. Should he shower tonight? He was going to be sticky if he didn't. It took a little longer than his usual anal play for everything to seep out. He didn't think they had used that much lube. Giving himself another quick wipe, he grabbed his PJs and slid them on and took a big drink of water.

Piper ran to the guest bathroom. She looked in the mirror, same woman, big grin, and a softening cock between her legs. She quickly wiped it down, twisting a little at the waist as she cleaned the sensitive head. She fairly ran back to the bedroom, pulled up a pair of panties and threw on her pajamas. She had just pulled up the covers when Mac came back to bed. He looked happy but worse for wear and really tired. She pulled him in for a quick loving kiss and motioned for him to be the little spoon. He obliged and she snuggled in behind him wrapping one arm around him and cupped one of his pecs with her hand.