Cross Dressing

He dreaded this day all week, hoping his girlfriend had forgotten their drink session, they bets' and his lose. But no, as soon as Saturday arrived, she had him awake by 06.00 am. Waking him gently by reaching inside his boxers and slowly playing with his cock, until he was hard, and he was awake. He smiled and rolled to face her, hoping for more.

"Hey babes, glad you are awake." She greeted him, before squeezing his cock ad climbing out of bed.

She was only wearing her tight yellow cotton pants and vest. Everything was covered but on show, her firm breasts, her tight pussy, and her cute bum. She walked into the bathroom and started to run a bath.

"Come babe, time to get up we are going shopping, remember?" she giggled from the bathroom.

He got out of bed, his erection still hard and sticking out through his boxers and went into the bathroom. She looked at him and then giggled again, winking. She grabbed the waistband of his boxers and dropped them so quick his cock bounced as it was freed from its prison and his balls bounced gleefully.

"Hmm at least it gives me something to hold to while I shave you." She suggested.

She got her razor and started to shave his legs, from the feet up, stopping at his groin. Then holding his erection, she proceeded in shaving his pubic hair off. Although the bathroom was warm, he felt a chill.

Once shaved she left him to have a soak, his balls and legs stung when he sat in the bath. However, they quickly settled, and he had a long soak, hoping the day would end and he could go back to bed.

He got out the bath dried off and found she had left his clothes out on the bed, quickly dressed, and headed to the kitchen.

She looked up as he entered and smiled at him.

"You ready?"

He smiled. They left their flat and headed into town, shopping. Yet not for food, nor luxuries. For clothes for him. She took him to her favourite clothes store and hunted for the perfect dress, not to long, not to short, as they old saying goes "long enough to cover the topic but short enough to keep it interesting."

She found just what she wanted, a royal blue skirt that was tight at the top and flared out at the waist, and just above the knee.

"Go on!" she ordered. "Try it on." Giving him the dress. "I will pick out your underwear. She giggled and whispered in his ear, "nice and sexy and tight, but will keep you covered."

She skipped off to the lingerie side of the shop. He slowly walked to the changing rooms; he was so embarrassed. People were watching him, more importantly women were watching him.

He entered the changing room and puled the curtain across. Slowly he undressed, until he was in his tight black pants. Unzipped the dress and slipped into it. It was a snug fit up top but nice and roomy from the waist down, just ending above his knees. He checked it out in the mirror and found he was getting aroused, especially when he turned around and the dress flared up, threatening to expose his bum and groin.

Suddenly the curtain as pulled back. His girlfriend looked at him, giggled then whistled. She reached round and pinched his arse.

"Looking good, babes, suits you."

"You don't think it looks bit short?" He asked.

"Spin around." She told him.

He did and the dress rode up. She smiled.

"Naw it's fine. Here put this on." She gave him a pair of red cotton bikini pants. Before he could complain, she had his dress up, and his pants down round his ankles. Twice today she had pantsed him.

He took them off and pulled on his new underwear. They were snug coming up past his thighs and left nothing to the imagination once he had them in place. His cocks' outline was visible, his balls tightly captured. Mind you he did like the feel of the soft cotton on his body.

"Come on then, let pay for your new dress." She pulled him out of the changing room, gathered his clothes and stuffed them in a bag. They walked through the shop to the tills. People watched, stared, and giggled as they went past. He felt his cheeks redden as they had to queue at the checkouts.

"These pants are really tight babe." He complained.

"Well, you could go commando if you prefer." She suggested and pretended to pull the back of his dress up. He smacked he hand away; she laughed and patted his behind.

They made their way along the queue to the tills, she made threats to expose his pants, by putting her hand behind him, laughing.

Once they got to the tills, the woman in front was packing her bags when she dropped her purse.

"Pick that up for her." She spoke.

As he bent down to pick it up, he felt his dress being pulled up at the back and knew his red bikini bottoms were exposed and then felt a gentle smack on his bum. He blushed, handed the women her purse. He tried to pull his dress down, but his girlfriend had it tightly in her grasp up over his waist.

As he turned to face her, he was shocked as the whole queue, was looking at him, his tight red bikini pants and the outline of his cock and balls showing through. Some giggled, some pointed, and a few were quick with their phone cameras. His girlfriend manager to manoeuvre behind him, keeping his dress raised like the famous Marilyn Monroe shot.

"You glad you didn't go commando now?" she exclaimed laughing.

They paid for his outfit and left the shop. He wanted to head home, but she had other ideas.

"Let's eat, I am starving." She exclaimed and walked to the nearest café. She pointed to a table by the window, he sat down, and she fetched the food. As he looked out at the window, he saw people walk pass, stare, and giggle. He was so ashamed but also felt aroused by his spectators.

10 minutes later, she returned with a tray, sat down in front of him.

"You know, if you sit in front of the window like that, best to put your knees together, I could see everything in the reflection. And I mean everything." She faked a shocked expression, put her little finger up and wiggled it, to mock his visible penis line through his cotton pants and giggled.

He went so red, swore, hid his face, and closed his legs, pulling the dress between his knees to cover up. He felt his cock trying to harden but was kept in check by his tight pants. They ate their food and left.

She wanted to do some more shopping both inside the centre and on the main road. It was rush hour and the centre was busy. Also, his dress kept blowing up, threatening to expose more than his thighs and bum cheeks and sent a draught round his balls. It was chilly, but also not an unpleasant feeling, making him feel more aroused.

They finally headed into one more clothes shop and browser round. She kept smiling and blowing him kisses.

"They still tight babe?" she asked nodding at his groin area. He nodded.

"OK, take then off."

"What here, now?" he asked.

"Yeah no one is watching, quick." She rummaged through her bags and took out his underwear. He slides his pants down to his ankles and kicked them off. She bent down and picked them up.

"Ha got you!" she exclaimed and walked off with both pairs in her hands.

He tried to run after her but had to keep pulling his dress down as it rode up. He followed her out of the shop, and she got into a waiting taxi. He jumped I beside her, his dress rode up from behind and exposed his bare bum cheeks to passerby before he could adjust it.

This time he made sure his knees were together as they rode home, she was playfully twirling both sets of underwear round her fingers, giggling and teasing him.

"Hmm." She whispered, "Imagine what my tongue could do to the tip of your cock babe, slowly twirling around your tip, kissing the shaft."

"Babe!" he snapped back, he could feel his groin stirring and this time no panty fabric was keeping it in check.

She chuckled to herself and watched his face. Then threatened to lift his dress up, exposing his naked cock, which she could imagine was getting harder.

They arrived home and she got to the front door first, turned the key and turned to face him. She out her arms round his neck and kissed him.

"That's for being a good loser and doing your forfeit and this...." she pulled his dress right up exposing his cock, balls, and bum. She held it like this.

"Is for making the bet in the first place."