Todd watched her from across the room. The braided blonde hair was clearly a wig. The rouge on her cheeks was overdone. The red lipstick on her full lips was too bright. But he didn't care. It was a Halloween. It was a costume. She should look overdone, shouldn't she? She was skinny, too skinny. Her lack of body fat had left her flat chested and that was a strike against her. But he liked her thigh high white stockings. He liked how her blue gingham checked dress ended just below her ass and showed several inches of flesh between the top of her stockings and the hem of her dress. Her "ruby red slippers" were actually spikey high heels covered in red sequins. Todd wondered which joke she had heard most often and decided that was his opening.
Todd threaded his way past the ghosts, ghouls, goblins and vampires towards the adult Dorothy look-a-like. He caught her eye and she smiled as he neared. "So which pick up line have you heard most often?" he asked as he drew close. Her smile stayed in place as she raised her eyebrows in question. He glanced at the stuffed Toto she held. "Let's do it doggie style." That earned a nod and a big smile. "Let me take you over the rainbow." She rolled her blue eyes and nodded again. "And probably something stupid about there being no place like home," he offered. Her big smile told him he had gotten it right.
Dorothy tugged on the sleeve to Todd's Dr. Who costume, urging him to bend over to hear her. "I'm an honorary member of the Lollipop League," she told him a low, sultry voice. She kissed his cheek and her small hand grabbed the front of his costume pants. "Want proof?"
Todd gave her a wide-eyed look as she smiled again. "You serious?"
Dorothy nodded, took Todd's hand and led him down the hallway towards the bedrooms. It took them two tries to find a bedroom that wasn't being used. On their third try, she opened the door, stepped inside and pulled Todd along with her. She leaded him against the door. Her hands went to work on the front of his pants.
"Whoa, Dorothy, you don't waste any time, do you?" Todd asked. He kissed her. She kissed him back. He tried to rub the front of her dress, finding mere bumps of breasts. She pushed his hands away and shook her head.
"Lollipop," she said in that sexy, sultry voice. She pulled open his pants and dropped to her knees.
Todd's head spun as her small hands began rubbing his bared cock and balls. Was it really this easy? Music from the party thumped through the door but the beat couldn't match the pounding of his heart as he looked at the pretty woman kneeling in front of him. Todd still held his beer in one hand. He toasted the moment as soon as he felt her lips on his prick. Whomever this person was masquerading as Dorothy wasn't shy. She drew his stiffening cock between her lips and nursed him hard. Her tiny hands caressed his ball sac as she bobbed her head. She batted her blue eyes up at him. "Yeah baby," he said as he carefully caressed her blonde wig. He pushed her head down farther and she took him without gagging.
Someone tried to door. Todd felt them pushing against the door. "Busy!" he called out. He found the door knob, searched for a lock and couldn't find one. It didn't matter. He could hold the door shut with his back. Had Dorothy known that? Had she pulled other men into this bedroom to demonstrate her honorary membership into the Lollipop League? Todd didn't care. "Suck it," he told her. "Suck that lollipop." Dorothy pulled away long enough to smile at him before she went back to work on him.
Todd's history of blow jobs was on the weak side. His first girlfriend refused to do it. His first college girlfriend would only do it as foreplay, never to completion. His last girlfriend would do it sometimes but not often and never to completion. Todd felt his balls tightening. He felt his thrill rising. He took a draw off his beer as he considered his obligation to tell his Dorothy he was close. Good manners got the best of him. "I'm close," he mumbled.
"Mm," Dorothy moaned without pulling away. She doubled her efforts on his prick and brought him off. He came inside of her mouth, the first time he had come inside of anyone's mouth. It felt as wonderful as he had guessed it would feel. He came, she swallowed and he felt welcomed by her. She rocked back on her heels. Her hand slipped beneath her short skirt and she rubbed herself.
"Give me a few minutes and I'll help you with that."
Dorothy shook her head and stood. She tugged his pants together but left the work of tucking himself together to Todd. She watched his hands and gave him another smile. Leaning forward, she kissed his cheek again. Sated for the moment, he held her hand as they walked back to the party. "Thank you. I'm going to mingle now, okay?" she told him. She let go of his hand and worked her way through the sides of the party.
Todd let her go. What did he care? He went back down the hallway; found the bathroom was free and relieved himself. As he washed his hands he glanced in the mirror and saw the competing lipstick smacks on his cheeks. One from before she sucked him and a lighter one from when she was done. He smiled at his reflection and returned to the party. On his way back to the living room, he passed Dorothy holding the hands of another man. She smiled at Todd. The man in tow wore a single lipstick print on his cheek. Todd laughed.
On his way to the kitchen for another beer, Todd scanned the party. He saw three other guys with lipstick prints on their cheeks. He shook his head and grinned to himself. Really? She had done that many guys? What a fucking slut. He decided he didn't want to be branded. Using a paper towel and some dish soap, he washed off his cheeks.
With a new beer in hand, Todd returned to the living room to watch the bumping and grinding on the makeshift dance floor. If he went home right now, he would feel complete. One last beer and maybe he would leave.
"Party!" yelled a drunken man wearing lip prints on both cheeks. Todd recognized him as the man he had passed less than fifteen minutes ago. She worked fast. He glanced around the room and found her standing off to one side. Another man was already talking to her and earning his first lip print. The drunken man cheering next to Todd was number six by Todd's count. He exchanged chest bumps with another man. "You see Dorothy over there?" the drunken guy yelled louder than was needed. "She just sucked me off."
"Dude, you're a fucking idiot," his buddy yelled back. "That's no chick."
"What the fuck?"
"It's a dude in drag! He's sucking off everyone he can!"
Setting down his beer, Todd left the party and tried not to notice the other lipstick prints he saw along the way to the door.
Thanks to DevilsRapture for the editing job!
Please Rate This Submission:
- 1
- 2
- 3
- 4
- 5
tdplayer01, eliotwill and 5 other people favorited this story!
- Recent
Comments - Add a
Comment - Send
Feedback Send private anonymous feedback to the author (click here to post a public comment instead).
very good
I liked it a lot, good hot storyline and creative but the you did yourself an injustice I think w/ the super fast ending- too quick a summation.
This story serves as a warning to heterosexuals everywhere. And the moral is simple, never trust your life to a hard on and a fifth of booze. Good story though!
I like the element of surprise, how he still had no clue even after she had sucked him off and kept him unaware all the way up until the point when he was leaving the party, and even then he only found out because someone else said it. This was pretty good.more...
Interesting idea
I didn't notice the category it was in so the end came as something of a surprise. Good one!
Thanks for the kind comments. Originally, I had submitted this in the "First time" category, but it was rejected by the powers that be with the category changed to "Transsexuals & Crossdressers." I agree, it telegraphs the ending, but hopefully it doesn't take away from Todd's experience or the fun of seeing all those other lipstick prints in the room. :-)more...
Show more comments or
Read All 8 User Comments or
Click here to leave your own comment on this submission!