The Tales of Crissy the Sissy Ch. 02

Chapter 02

Chris Masters found his phone plugged into the charger. There were 37 new messages. He scrolled through the first few. It was a few of the guys from work. Some of them were giving him shit for calling out sick and a couple were worried about what had gone down the night before. A majority of the messages were from an MM.

He clicked on the contact. The picture was of a very tall, lovely, orange haired woman in an R2D2 dress. Mistress Martina was listed under the picture as contact info. He remembered, now, some of the events at the little hole in the wall bar, and sat down on the edge of his bed. He jumped slightly when his ass made contact, as he felt like he had been split in two.

She was a trans woman and they had fucked, well he had been fucked by her, and he remembered enjoying every moment of it.

A few messages from her explained she had found his work numbers and called in for him, saying he had a family emergency and was going to be gone for a week. She had taken his costume to be dry-cleaned before he returned it. It had a few new 'stains' on it. She had, with the help of Carl, gotten him home and back into bed to sleep and recuperate. Half of the messages from her were pictures and short videos of the previous night. The first picture showed him standing in his Red Riding Hood costume, his lips locked onto Martina's extra-large breast. His cock stirred a little.

The next few showed him on his knees in front of her. One with her beast of a cock standing up, the next with his hands wrapped around it, another with the swollen head in his mouth, and one with the monster stuffed down his throat. He moved his jaw from side to side and understood just why it was so sore this morning. The next message was a video clip of him sucking her balls into his mouth and then moving her cock to his mouth and her face fucking him for quite some time. Chris had to admit, it was pretty hot, even if it was him in the video.

His phone dinged. Another text message.

MM: Hope UR doing ok. Let me know. Hope I didnt break u <3

CM: Just woke up. thanx 4 getting me home. Not broken worn out

MM: Not 2 worn out I hope? Working 2nite. U should cum by if you can.

A minute went by without him responding.

MM: watching our video again. Im soooo hard right now ;)

His phone dinged again and Chris opened the next message and found a picture. It was her monster cock encased in little pink boy shorts. It bulged across to her pelvic bone. Her one hand was framing it, as if it needed to be pointed out.

CM: Wow! I'll let you know a little later. Think I just need some rest right now

MM: ok if ur up to it just come by the bar. Ttyl

Chris had to admit he was flattered. She was gorgeous and apparently wanted him. That hadn't happened since freshman year of high school, right after he stopped growing. He got up and stretched his slim 5-foot, 7-inch frame. He rolled his neck around to loosen it up. Martina had a hell of a grip when she wanted to. His phone dinged again.

MM: Forgot. I left you something by your door. Hope you love it

With his curiosity piqued, he walked naked through his apartment to his front door. There was small pink bag, tied with a ribbon. He picked it up and took it into his kitchen. He pulled the ribbon and the top was opened. There was a card.

'Hope you had as great of a time as I did. You should wear these from now on. I'm sure they will look fabulous on you. -M' and a large kiss in hot pink lipstick, was on the card.

He dug in and removed several packages of women's panties. There were some regular cotton ones, some slim colorful satin ones, and a pack of thongs in several different prints. Not the first gift he would have thought to get someone, but he did remember her disgust at seeing him in his tightie whities the night before. An idea hit him. He opened the satin panties up and grabbed the red ones.

'No. Wait. This wasn't what I should be feeling. I am a man. I shouldn't be....' His thought trailed off as he rubbed his fingers over the satin in his hand. She WAS sweet enough to get me a cute gift. It's only right that I show her how they look on me. I know she would love to see them.

He ran back and grabbed his phone. He pulled the panties up and they fit rather well. They were soft against his ass and felt even better against his semi-hard little prick.

He tried playing with himself a little to harden up. Then he remembered and searched through the text messages from earlier. He found one with a video and clicked it. It was the clip of him turning his head to look up at Martina as she started to really pound into his virgin ass last night. Sure enough, that did the trick. He situated himself for a better angle and took a few pics with his phone. He hated to admit it, but it felt kind of sexy doing it.

He found one he thought looked good and sent it to Martina. Just a few second later his phone dinged.

MM: OMG!!!!! <3<3<3 you little tease. Didn't think I would get something like that so soon. U better get some rest and get that sexy ass to the bar 2nite!!

Chris was grinning from ear to ear. Never in a million year would he have thought this would happen to him. But he figured this was happening. He went back to kitchen to find something to eat. He was starving. After reheating some leftovers and practically inhaling them, went to get himself a shower. As he removed his new satin panties, he found he quickly missed the feel of them on his bare skin. He showered quickly. He gently scrubbed around his tender asshole. It was still sore to the touch.

He finished his shower and dried off. The red panties sat on his bathroom counter. He quickly slipped them back on and sighed as the comfort took hold of him. Chris went and lay down on his bed. It was late afternoon and he was still a little groggy. He wiggled around on his bed and eventually snuggled up to his pillow and slept.

When he awoke again it was the close to sunset. The red-orange hue of the light filtering through the windows reminded him of Martina's fiery orange hair and his little dick stirred. He reached down and rubbed himself through the satin covering his tiny manhood. He found his phone and pulled up his text messages. He clicked on another video clip she had sent.

'Martina was pushing her monster into his tiny little ass. His hands were gripping the couch tightly. She pulled her hips back and Chris' ass followed the movement. She pushed her hips forward and Chris' head popped up with his mouth in a silent oh. Her hands moved down his back and grabbed his hips. She pushed all the way in. His hips bucked in her grip and bit of his spewing cum could be seen hitting the cushion under him.'

Chris let the video clip run on repeat and rubbed himself in his new panties. His mind flashed with a new idea. He bunched up one of his pillows and rolled over on top of it. He placed his phone next the headboard and watched it. His slender hips started rolling into the pillow. His little hard cock slid back and forth inside it's satiny new home.

'Oh My God!' he thought. Why have I never tried doing this before. He sped up his pillow humping and could feel himself tingling with excitement. After only just a minute or two he felt his sack tighten up and his rod start to shoot his cum into his panties. His hips twitched and legs shook. He could feel the warm seed spread around his crotch. After finally calming his body, he rolled off his pillow, leaving a small damp spot. He could smell his cum and a curious though entered his mind.

'What do I taste like?' He grabbed his damp pillow and rested his head next to the dampened area. The smell was stronger and filled his nostrils. His head became dizzy. He moved his face closer to the spot on the pillow. That sense of euphoria began again. It wasn't quite as intense as last night, but it was there.

He inhaled deeply. His head swam again. He placed his nose in the center of the wet spot and then rested his face, so it stayed right there. He felt the dampness on his cheek. The musky smell was his only focus. He lay there for several minutes enjoying this new feeling.

He came around and had another realization. I have satin panties on that have my load in them. I could be resting on those instead of a wet pillow. He looked down to see his soggy panties, half-stained dark red from his own juices. He reached down and peeled them off. He was careful not to let anything drip out. He didn't want to waste any of his precious seed. His now wilted dick was a gooey mess, a bit of cum was mixed into the small amount of hair he had over his little 'man'.

He brought his panties up and placed them on the already soiled pillow. He stared at them, not really sure what to do with himself. He slid his head across the pillow closer. The red mess was just inches from him. The smell of his cum was so strong now that his head was set to swimming yet again. He inched his head ever closer. His nose was almost touching the moist satin panties.

Chris' eyes were closed as breathed deeply. He felt himself chewing on his lower lip. His hand moved down to rub over the cummy mess of his little cock. His fingers collected some as they moved over it and continued down and passed his deflated sack. His slick fingertips probed the edges of his tender anal ring. He flinched slightly at the touch. He moved his fingers around the outer circle, spreading his seed over the sore hole. The cooling stickiness seemed to be just what he needed to help soothe the tender flesh. He sighed contentedly.

He slid his head over just a little more on the pillow. The soiled panties were now firmly under his nose. Chris inhaled deeply. That euphoric feeling swept over him again. With his free hand he reached up and grabbed the panties. He held them close to his nose. He felt the sticky wetness all over his face now. He let his tongue escape his mouth just slightly. It made contact with some of his cum and he groaned. He pushed the panties into his face harder. He felt his cum squish through the thin fabric.

He opened his mouth and pushed some of the panties into it. His body twitched with excitement. The salty taste filled his mouth and he sucked in. Some of the cum dripped out of the panties and he swallowed eagerly. His entire world at this moment consisted of only him, his bed, his panties, and his cum.

Chris spent several minutes like that, sucking the cum out of the soiled panties. His eyes stayed closed and he groaned with delight quite often.

Eventually he opened his eyes and saw that the sun had set completely. It was dark out now. Now he had a very important decision to make.

What was he going to wear to the bar to see Martina?