A Soft Ride Part 1

this was commissioned from me by TheMarioGamer, Enjoy!

Samantha finally had enough after her birthday; her boyfriend yet again got her something lazy and uncreative for her birthday. She felt hurt because she always put so much effort and planning into the gifts she got him every year, but this year she finally snapped. Her boyfriend handed her an envelope; she tore it open and opened the letter; it was a piece of lined paper with the words “Happy Birthday, Sam.” There was loose change that smelled like rust at the bottom of the envelope. Samantha is by no means greedy or expecting something wildly expensive. All she wanted was some thought and effort; she’d take a handmade craft; she just wanted to feel like Charlie cared about her as much as she cared about him. She finally confronted him about it, and he finally rolled his eyes and said, “Fine, message received; next year I’ll get you a thoughtful gift, and I’ll try really hard. You mean a lot to me, honey!" She smiled, and Charlie actually sounded sincere.

11 months later

Charlie’s birthday, which was a month before Samantha’s rolled around, was so exciting that Charlie might actually try this year, so she saved up all year, even taking overtime at work. She bought Charlie his favourite car, a fully loaded Range Rover. After thank you's, we’re exchanged. Charlie looked at Samantha and said, “You’re really going to like your present this year, baby! It’s a big surprise; I’ve been thinking about it and planning it all year; it might even outdo this Range Rover." Samantha was super excited. Charlie kept speaking about how the surprise was well thought out and big; she was thinking maybe he’d take her on a trip or a drive somewhere in his new car. But when she unwrapped her gift, she was seething. There, in front of her eyes, a 6-foot teddy bear was sitting. She was seeing red; she wheeled around and unloaded on her boyfriend, ending with “maybe we should break up." Charlie was desperate and started pleading with Samantha for one last chance. She thought up a plan and immediately put it into action. She tossed Charlie her pink, flowery shaving cream and her fake tan spray. “I want your whole body shaved and tanned; you will also be doing your makeup; follow the tutorial I send you; you will be using my makeup. While you do that, I’m going to purchase something for today." He was about to complain until Samantha added, “Oh, and any complaining or questioning me, and we are done for good.”

Charlie started shaving his body with the flowery pink shave foam, and when he was done, he felt super smooth, soft, and smelled of a field of flowers. He applied the fake tan and got started on the makeup. Following the tutorial down to the pixel, he had to re-do it a couple times. He was just finishing it when Samantha got home. *click* She had just taken a picture of him, mouth open, applying lipstick, and then another of him pouting to make sure he did it right. “Hey! Delete those, please!” Sam smiled and said, "No. These are to make sure you follow my demands; if breaking up wasn’t enough incentive, now there’s pictures as well." She helped him with the rest of the steps; she glued on some breast forms, hip pads, and a corset in its maximum setting. She glued on cherry-red nails and giggled. “They match your name, Cherry!" She then glued in long brunette extensions to match his hair colour, and she pulled the mass of hair into a tight ponytail, none too gently. He winced, “Ow!" Samantha looked irritated. "Oh, shut up, Cherry.” She grabbed the ponytail and gave it a quick tug as hard as she could. “OW! What the hell are you doing back there?” Samantha had an evil grin on her face. “Just make sure it’s tight and secure, Cherry; we don’t want your gorgeous hair to fall out of the ponytail, do we?" She gave it another hard tug, causing Charlie’s head to whip back. She decided to move on as fun as doing this to him; she had something better planned. She slipped some pink frilly crotchless pants up his bare, tanned legs. He felt her pull his butt cheeks apart, and he pulled away. “What are you doing?" “Just make sure the pants are sitting properly so they don’t give you a rash. He suddenly felt something smooth and large being shoved into his rectum; it was uncomfortable, and then he felt shaking pleasure in his legs. “What was that?" A butt plug of this size is supposed to be for those experienced in anal penetration, but you seem to be handling it well. I suppose your ass was built to be penetrated. something else to keep you in line.”

She yanked the frilly pants up as high as she could, wedging them in between his new butt bubble firmly. Doing this, she pushed the plug deeper, causing him to squirm and moan with pleasure. He hated that he was moaning and enjoying something in his ass. She had him wear a backless black top with thin straps. She pulled him into white skinny jeans, pulling them up until his new butt finally slipped into them with a wshhhh. She forced his feet into her 6” black boots with red bottoms that were 4 sizes too small for him and zipped him in tight. "Alright, let’s go, Cherry." Charlie looked confused. “go? Go where?” She smiled and said, “For a drive in your new Range Rover." “I can’t drive in these tiny boots!” "I never said you were driving; I am, and you’ll be my sweet passenger, Princess Cherry!" “Stop calling me Cherry! My name is Charlie!" Samantha ignored him and pushed him into the passenger seat. She went inside for 5 minutes; he wasn’t sure what she was doing, but she came out brushing stuffing from her shirt and bottoms. “We forgot your driving buddy, Cherry!" She unzipped his pants, and a rock-hard cock flicked out: “Someone’s enjoying themselves!" She revealed the hole in the bottom of the teddy and placed the hole over his cock.

With the teddy now on his lap, she took the seat belt and tightened it as much as she could. 

She yanked hard and quick on the belt to make sure it locked in place and couldn’t be loosened unless she let him out. “Every time you cum inside the bear, I’ll make a girly modification to your car, all through your credit card, of course.” He felt his ass buzz twice; maybe he sat on his phone? Then he looked over at Samantha to see her holding a remote. “This is going to be a fun ride, Cherry; be sure to enjoy yourself!” She cranked the vibrator to maximum. She pulled out of the driveway and ‘accidentally’ pulled out over the curb, causing the car to jolt. She heard him moan, and out of the corner of her eye, she saw his legs shake and kick. He was breathing heavily, then he let out a heavy moan and went ridged for a couple seconds, then relaxed. “Well, say goodbye to these black leather seats, Cherry; we need seats better fitted for you; I’m thinking pink and furry seats with a pink and furry steering wheel to match!” After 2 hours of her purposely hitting potholes, bumps, and curbs, she ran out of things to change in the interior. She giggled. I guess all that’s left is the paint job, the head lights, and the license plate. She giggled and teased him, "Wow, Cherry! Your driving buddy is really enjoying himself! You’re really giving him a treat, letting him sit on your lap." To make sure those changes happened, at stop lights, she would make sure there was no one behind her, then brake hard, causing his dickey to slide deeper into the teddy. Then, she would quickly accelerate away from the light, causing his dickey to slide slightly back. Combining both of these causes a thrusting motion.

After another hour, she couldn’t think of any more changes to make to the car, so she drove home.

Charlie is completely spent. After constant, uncontrollable pleasure cumming into the teddy almost nonstop for 3 hours, the teddy is soaked on the inside, and there is a sizeable puddle built up inside of it. and his girlfriend's constant teasing in the car, he sits there nearly asleep. Samantha unbuckles him, and he gets out, hugging the teddy tightly so the cum doesn’t pour out. One of the neighbours called over, “Is the man who bought you going to get lucky tonight, sweety?” Samantha called back, "Oh, she’s already got her smudge-proof lipstick!” The woman let out laughter and called back, “You go girl! The guys really like it when you kiss the tip and when you stroke those pretty nails up and down the shaft! It will drive him wild; trust me, girl!”

Samantha smiled and called back. “Cherry will keep that in mind! Thanks for the advice!”

Charlie was red with embarrassment and huddled inside. As he hobbled into the living room, a bunch of women jumped out. He recognized them as Samantha’s closest friends, and they yelled. “Surprise!" They were shocked and confused to see a random girl in front of them. Charlie was more shocked. Dropping teddy, causing his dick to flick out, flacid covered in stuffing, when the teddy hit the ground, it made a heavy splat and cum splattered out onto the floor.

His girlfriend walked in behind him and gasped, dropping fake grocery bags on the floor. “Is this what you do when you are home alone? Dress up as a woman and hump my stuffed animals. All I did was go and get groceries." Half the guests are absolutely appalled, and the other half are giggling at the sissy in front of them.