My first story. I really hope you enjoy it. Please let me know what you thought of it, any feedback would be welcomed.
As soon as the door slammed David was up. He swore at himself for his complete lack of self control, but he just couldn't help himself. Every opportunity he had, he was doing what he promised himself he would never do again. There wasn't any shame in what he did, he wasn't hurting anyone, and he enjoyed it. It was who he wanted to be.
It was the fear of being caught that haunted him. How would he ever explain his new hobby to anyone. His need was getting stronger everyday, and now it had become more intense, the need to push it further was becoming his obsession.
David headed to the window and checked everything was clear, that his daughter's car had gone. He lived alone now, had for a while, but she visited occasionally, staying in the spare room. His daughter and son were old enough to have started lives of their own now, which left him free to do what he liked, and he did.
He quickly had a shower, rushing as fast as he could, his desire growing every second. He made sure his body was smooth and hairless. God knows how he was going to explain that in the summer.
As soon as he was out he was opening his wardrobe, sliding aside his suits, he wouldn't need those today. Hidden at the back was what he really wanted, that and the box pushed into the far corner.
What he had really wanted was the backless red dress that been hanging away from prying eyes. The one he had treated himself too a few days ago. He pulled it out and looked it over.
"Beautiful," he said, pulling it off the hanger and lying it on the bed. He couldn't help but rush now as he quickly opened the box. Finding the items he wanted.
He did his make up first, only a light application, he was still quite new to all this, but online tutorials had helped. He put on his wig of long silky black hair, it had been expensive, but worth every penny. It flowed beautiful down his back and made him feel incredibly feminine.
He put a bra on with some fake implants and then the dress went on, it hugged his slim body perfectly. He loved and twirled in the mirror. He knew he would be looking at himself all day.
The next item filled him with the most excitement and his hand trembled slightly as he took it out. He wrapped his fingers around the black object and picked up the bottle of lube next to it.
David wasted no time in covering the plug in the lube, and putting some on his fingers. He pushed a finger gently into himself, spreading the lube inside him, he added another finger, stretching himself ready for the plug. He moaned softly at the intrusion. He was ready.
His legs trembled in anticipation as he pushed it into himself, he felt the tip of the buttplug touch his asshole and he moaned softly. He pushed harder and felt it open him up slightly, making him want it inside him. He used more pressure to help it slowly enter him, the thick head of the buttplug widening him further.
It pushed inside him until he felt resistance, he purred as it stretched him to breaking point, a stab of pain around his ring. This was his favourite bit and he couldn't wait any longer. He pushed hard.
"Oh god," he moaned, as the head of the plug finally broke through the barrier of his hole. It nestled perfectly inside him, making him fill full and content.
He looked at it in the mirror, lifting the dress over his pert bottom and sticking it out. The end of of the plug visible between his firm cheeks. He teased the end, wriggling it inside him, it felt good.
Next he pulled on a pair of black lace panties, tucking his penis in and covering the plug. Then the stockings went on. He pulled them up to his thighs on his long slender legs. He loved the feel, but as he glanced in the mirror he loved the look more. He felt himself hardening already. The dress looked amazing, hugging his slim frame and high on thighs.
He turned and looked over his shoulder at his pert bottom, and then the slender contours of his back and shoulders. He felt great with his look.
He decided to go downstairs for a coffee and some breakfast, the fun could wait. The rest of the toys in his box would have to be patient.
David headed downstairs and walked into the kitchen and then stopped suddenly, his heart felt like it had been gripped by a large cold hand. There was someone there.
"You took your ti..." the man said, stopping short as he looked up and saw the unknown woman in front of him.
David watched as his face turned from confusion to recognition, and then back to confusion. David wished he could shrivel up and disappear. The man in front of him was his friend of many years, and also his work colleague.
"David?" Nathan said. "Um ... sorry ... the door was open ...and well, I heard you in the shower so thought I would wait."
"What are you doing here?" David said quietly. His face had flushed red, the heat building with embarrassment.
"We had a meeting arranged," Nathan replied. "I should go."
"No wait, please. Let me explain," David said, panicking. Nothing else would come out though. What was there to say, it was pretty obvious.
They stood in awkward silence. Nathan waiting for David to carry on, his eyes kept flicking down his body, taking in the figure hugging dress, and the legs in the stockings. If he hadn't of known David he probably never would of guessed this wasn't just a very attractive woman. His cock stirred. What the fuck, he thought.
David couldn't help but notice how his eyes ran over his body and settled on his legs. He was sure he saw longing in them. He suddenly had an idea, one that assured his secret stayed safe, and that also turned him on massively. He had nothing to lose, he thought.
The desire inside him swelled. It gave him a confidence he had never felt before, he knew Nathan wanted him and that sent his arousal into overdrive. David looked at Nathan with his own longing. Slightly taller than himself, he was mid forties and in good shape. He looked good in his light green shirt and jeans.
He walked towards where Nathan stood and enjoyed the look that he received.
"As I'm all dressed up it would be a shame to waste it," David said. He put one hand on Nathan's chest, the other went straight to his crotch, feeling the semi hard cock between his legs.
Nathan went to pull away, but he didn't, he couldn't help admit to himself that in front of him was an incredibly hot woman. If he didn't think of her as David then maybe...
"I don't think we've been properly introduced?" Nathan said, feeling himself harden under the teasing of his penis.
"That's true. How rude of me," David said in his most feminine voice. He felt himself becoming his other self. He had never become her in front of someone before. The thrill coursed through him, he felt his own arousal.
"Millie-Rose," she said. "You can call me Millie." She squeezed him harder.
"Nice to meet you Millie," Nathan said. "I'm guessing by your hand you want something?"
"I do," Millie said. She wanted it bad. She had fantasised about this moment hundreds of times. Had thought what someone else's would feel like, how it would taste, and how it would feel inside her. She groaned.
"How much do you want it?" Nathan said. His hand went up her thigh and under her dress, he squeezed her bum, feeling her lace panties.
"I want it so bad," Millie said. "I need it." She started undoing his trousers. Forcing her hand inside his boxers and touching it. Wrapping her fingers around it.
"Do you love cock Millie?" Nathan said, he couldn't help himself now. "Are you a cock loving slut?"
"Oh god I am," she moaned. "I want to be your cock loving slut. I want it deep down my throat."
Nathan pushed her down and Millie dropped eagerly to her knees. She made quick work of the rest of trousers and pulled his hard member out. She couldn't help the yearning noise that left her lips. It looked amazing in her hand as she started slowly pulling the skin back and forth. The warmth and throbbing hardness felt good against her skin.
It was a good size, about 6 inches and thick. She ran her tongue from the base to the top, kissing the head, and tasting a drop of precum. It tasted just like her own and she loved it.
She took the head in her mouth and forced her head down, forcing it down her throat, taking most of it in, the practising on dildos had worked, and she held it until she gagged. Nathan moaned. She came back up for air and left a trail of spit on the shaft.
"Someone's had practice," Nathan said. "Like all good cock sucking sluts." He gripped the back of her head and forced the cock back inside her mouth. She took it in eagerly, letting him slowly fuck her face. She released her own hard cock from her panties and started stroking in beneath her dress, it rubbed against the soft fabric.
"So good," Millie moaned, as she came up for air. She worked on the penis for a bit, sucking, and licking. Occasionally staring up into his eyes as she wanted him off with her lips. It wasn't long though before she needed something else.
"I want it in me," Millie moaned, looking up at him, still stroking. "Please fuck me." She was stroking herself quickly now, her cock hard and tall, bulging beneath her dress. She couldn't describe how much she wanted to feel a real cock inside her, she had loss any sense of control.
Nathan too had lost it, consumed by lust. He lifted her up and spun her around. He bent her roughly over the table, gripping the back of her neck, he leant in over her, and his hard cock pressed between her legs. She felt it against her own
"Do you want my cock inside you?" he said into her ear. So close she could feel his breath on her cheek. "Deep inside that hot ass of yours?"
"Oh god. I do," Millie moaned. "Fuck me. Please fuck me."
Nathan lifted her skirt over her narrow hips. He pulled her lace panties around her thighs and smiled as he saw the ball of the butt plug stretching her tight asshole. He caressed her thighs, feeling her stockings, his eyes not leaving the end of the toy. His cock now raging to be inside her.
He took the exposed end of the plug in his fingers and pulled. He had a big smile on his face as he eased it out of her asshole. Her ring stretched wide and he heard her groan a he felt her tight hole resist. He pulled hard and it popped out, her hole gaping briefly before closing. It glistened with lube.
Nathan leant over her again and pushed the plug into Millie's mouth. She sucked it in, tasting her own ass hole.
"Mmmm," she managed. Sucking on it. Then she gasped as she felt the tip of Nathan's cock press against her hole. She was well oiled and stretched, and he slid in hard. She cried out in pleasure. There was brief pain, but it was outweighed by the pure bliss that overcame her, as the thick cock stretched her open and filled her anal cavity.
"Fuuuuuuck," she moaned. "So deep." He wasn't wasting any time, she thought, as he started to slowly fuck her. The shaft of the cock slid in and out of her.
"So fucking tight," Nathan groaned. He wanted to cum now, it was all too much. The sight of the tight asshole stretched around his cock was too amazing. Her pert bottom, her thin waist, and slender back and neck stretched out over the table. He started fucking her harder.
Nathan's watched with fascination as his penis slid in and out of her, the tight hole squeezed his shaft hard. He wanted this to last, but the sensation was too much, the more he wanted not to cum too soon, the closer he came to the edge.
"Fuck, fuck, fuck," Millie moaned with every thrust. His pelvis banging her into the table, the cock burying itself deep. She pulled herself up a bit, gripping her cock again and stroking fast. She knew he would cum soon, his groans and breathing becoming heavier.
"Cum for baby," Millie said. "Cum inside me." The thought of cum inside her pushed her closer.
"Oh fuck," Nathan grunted. "I can't stop it." His cock spasmed in Millies ass and ejaculated, coating her insides with cum. He thrust forward with each spurt.
The sensation of Nathan's twitching shaft inside her and the thought of the cum filling her sent Millie over the edge. She moaned loudly and orgasmed hard, covering the fabric of her dress in her cum. She collapsed forward onto the table, the cock inside her still finishing it's last few ejaculations.
"Oh fuck," Nathan said, slowly pulling out of her. As the head of his penis came out some cum followed it, dripping down into the lace panties around Millie's thighs.
Millie reached round and pushed some fingers into her still gaping hole, covering her fingers and then locking them clean, sucking them into her mouth.
"Mmm. Thank you," she said. She stood up and turned, resting her bum against the table. Her legs still wobbly.
"My pleasure," Nathan said. "Thank you too." He looked a bit uncomfortable now and had started doing his trousers up quickly.
"I'll let David know you popped round," Millie said. "I'm sure whatever it was about can wait till tomorrow."
"Yeah thanks," Nathan said. He was grateful for the way out. Things were now a bit awkward. Millie watched him as he straightened himself out and left, giving an awkward wave as he went.
When the door shut, Millie laughed. Yes it had been awkward at the end, but it had been worth every second. The feeling of cum in her well fucked asshole was proof of that.
She had hoped it would satisfy the urge that had gotten so strong lately, but she already knew that wasn't the case. She already wanted more.