You Want to Ask Me Out?

He saw her standing alone across the large room. Her back turned to the party crowd as she looked out the windows and over the city. The long hair, the confident stance, the curves. They all caught his eye and drew his interest. She looked like a girl he’d like to ask out. He took note of the empty champagne glass at her elbow and snagged two fresh ones from a passing tray. As he approached he could see she was not like most of the other women at the party. There was a presence about her, a power or strength that he was drawn to. All the other skinny women seemed like fragile dolls while he could imagine wrestling in the sheets with this woman as she laughed and growled. Just the thought of that made his dick swell in his pants. All the better. He wanted her to see his bulge. When he arrived at her back he cleared his throat and said,

“Excuse me. I saw your glass was empty so I brought you a fresh one.” She turned and fixed him with an intense stare, assessing him. She noted his bulge. 

“It’s empty because I don’t like champagne. I’m more of a beer girl.” Her eyes drilled into his. Challenging him to stay or slink off back into the crowd. He stood his ground.

“Oh? Well I guess that leaves more for me. Would you like for me to get you a beer?” His eyes drifted down over her.  Pretty eyes, nice rack and….whoa! They snapped back up to hers. She had no reaction on her face when she challenged him again,

“See something you like? Want to ask me out now, or are you just another close minded guy?” He hated being called out and when someone challenged he had to meet it head on.

“Yes. I do want to ask you out. That’s the whole reason I came over here, but if you’re too busy playing the tough ass bitch and trying scare me away to be interested in a date, just come out and tell me. Then maybe I can have a shot at one of these other less interesting women.” His nostrils flared a little as he defiantly held his ground and sipped his champagne. A Mona Lisa smile touched her lips.

“You think I’m interesting?” He took another sip as his mind swirled with where this was going.

“Definitely.” He declared with a nod of punctuation. 

“What if I’m too much for you to handle?” Now it was his turn to smile.

“I guess there is only one way for us to find out.”

He tossed back the last of the champagne, set the glasses on the window sill and offered her his arm. The surprise he saw on her face gave him sweet satisfaction after how things had begun. Her arm slipped through his and her hand gripped his forearm with a strength that gave him goose bumps. That wrestling match was going to be very interesting. 

Not Your Little Boy Anymore

This picture could probably bring up multiple fantasy lines. Here’s what it pulled out of my head.

She hadn’t been invited to the graduation party. June, his mother, knew there was some kind of connection between her young son and Angie, the woman next door. She’d moved in beside the single mother and her son when Tommy was a freshman.  At first things were fine. Tommy was simply the gangly kid next door that mowed her grass and did other odd jobs around house for extra cash.

After a few years things changed. He began to struggle keeping eye contact with her, his eyes were always drifting to her boobs, not that she could blame him. After all she knew she has some really nice boobs. She also caught him staring at her whenever she was out sunbathing in her bikini.

One day he was so distracted by watching her he accidently blew a bunch of grass into the pool. Angie yelled at him,

“Tommy! Watch what you’re doing! Damn it! I just paid to have that pool cleaned yesterday! I ought to bend you over my knee and spank your ass!”

Tommy looked horrified and instantly got an erection which only embarrassed him further. Angie found his erection very enlightening. Tommy let go of the mower and dashed for home. Angie mulled over Tommy’s reaction. Was it just an inopportune erection, or was there something deeper at work here. She’d never considered sex with him. He was much too young and while she and June weren’t friends she did respect her and would not take advantage of her son. Besides, she was pretty sure he had no idea she had a penis.

A week went by and the grass was starting to get tall so she texted Tommy and asked him to come over so they could talk it out. He agreed and a few minutes later was sitting on her couch. She was wearing a short black skirt, stockings, heals and a button up blouse that showed a lot of cleavage. Angie figured if he got another erection with her dressed like this he was just a normal red blooded boy.

“Thanks for coming Tommy. I’m sorry I yelled at you last week. I was all stressed out about work. More iced tea?” She leaned down to give him a good look down the front of her blouse as she served him. No erection. Interesting. Now to try theory two. “But I was also pretty upset. It costs a lot of money to get that pool cleaned and when you blow grass into it the very next day I feel like I should be allowed to be angry and even spank you!” She said this sternly and was instantly rewarded with his hard on. His hand went to his crotch to try to hide it. “I think you’ve been a bad, bad boy Tommy.” She stood right infront of him, hands on hips, feet shoulder width apart, looking down on him sternly. “And I’m going to punish you for it.”

Tommy squirmed in his seat for a moment then made to duck past her for the door.

“STOP RIGHT THERE!” He did. “TURN AROUND!” Again he followed orders, with both of his hands covering his aching appendage. His face was glowing with euphoric humiliation. Angie had her answer. He was incredibly turned on and her control was complete. She feels a familiar thrill of power surge through her as their rolls solidify. “You will be graduating soon and by that time you will be an adult. I will punish you then. But until that time we will go on as if nothing has changed and I will torture you with words and visions. Only in your actual punishment will you find release. Do we understand each other?”

Tommy nodded and for the rest of the school year she ordered him around her house. She was stern, demanding, aggressive and everything he desired. She would wear her lacy things around the house and a bikini when outside. She would get close to him, close enough to smell her and never touch him. She built up how she was going to punish him, make him hers and take control in ways he couldn’t imagine. Tommy had a constant erection whenever he was near her.

There were two weeks left in the school year when June showed up on Angie’s front step one afternoon.

“Tommy won’t be working for you anymore. I’m not sure what’s been going on between you two, but it has to stop. He needs to focus on his life. Not you. He’s my little boy and I want him to be successful and go to college and meet a nice girl, get married and have some babies. You’re not part of that picture. So it’s over. Understand?” Angie smiled a genuinely compassionate smile.

“I never meant to be a distraction to Tommy and I’m sorry if I have been. If that is your wish, I will honor it. However I want you to tell him it’s your choice. I don’t want him to think it’s coming from me. Deal?”

June nodded and stomped back home.

Two weeks later Tommy graduated and there was a big party at his house. Lots of family and friends came by to visit. As the party was winding down June noticed that Tommy was missing. She looked through the house and couldn’t find him anywhere. Suddenly she knew where he was. June dashed out of the house and jogged over to Angie’s. She knocked on the door and rang the bell several times, but no one answered. She tired the knob and the door swung open. Deeper in the home she heard the unmistakable sounds of sex. She marched into the family room and found Angie and Tommy going at it, but she was confused. Uncertainly she said,

“Tommy?!” Angie looked back over her shoulder as she was at last punishing Tommy and said,

“I guess he’s not your little boy anymore.”