Dating the Summers

Sitting at the table Bailey’s reading was interrupted by the sound of a motorcycle near the house. He wasn’t sure if it was Liam pulling up and stopping or just someone passing by, but he held still like it would save him. When one minute turned into two and no knock came to the door Bailey let out a sigh and went back to the childhood development game. Currently he was working with a new mother suffering from postpartum depression and he needed to get the new mother to form a secure bond with her baby to get emotional bonding to happen. The game gave information like postpartum hormones could affect a mother for up to six months and how it is not uncommon for a mother to have emotional outbursts like crying during this time.

It made Bailey think about how he at first told Mommy no about having kids and then told her if it is God’s will. Having sex without condoms was always so much better, but at that point he had gotten surgery to make sure he never put a bun in her oven. If he got her pregnant she would be in her fifties by the time that child was ready to learn to drive and heck he had heard of how much riskier it was to have a baby as women got older. Those thoughts were on his mind as he got himself fixed, but as he looked at the little baby on the screen with the scenario mother not wanting to hold it he thought of what really bothered him. One day your parents die, that was true for everyone, but his family it happened much younger than others. If he had a baby then more than likely he would die before it hit thirty, everyone dies, but the Smiths seemed to have a history of doing it earlier than others. “Like come on Marleene just pick up your baby, he wont stop crying.” Bailey begged the new mother on the screen to do what he wanted, refocusing his attention to the game instead of thinking about his parents and how they mostly left him to his own devices his entire life before leaving him.

“Pumpkin, our dates are here!” Bailey heard Aunt Megan call from the living room. Hitting save on the screen he knew he was going to have to read more into postpartum depression before he figured out how to pass this level, then closed the laptop. Standing up he took a deep breath, checked his makeup with his phone before coming out into the living room.

Opening the front door Megan let Charles and Liam past her, taking notice of how both younger men looked at her. She gave them both a small smile, especially as she noticed Charles’s eyes lingering on her chest. “Hello boys.”

“Hello yourself beautiful.” Chuck said, giving her a kiss on the cheek as he brother gave her a respectful nod and looked upon his date. He saw the pretty platinum blonde girl looking back at him with her green eyes, she seemed to flutter her long eyelashes at him as he took his date in. She wore this white cami top that was all lace below her breasts, it showed off a good deal of her assets and while they weren’t nearly as large as her Aunts, she had plenty for him to touch, and it looked like she was wearing no bra.. Most of her belly was exposed with the small top and tight short black leather skirt. On her feet were a pair of black heeled boots that came up just below her knees. He nodded at her with a big smile, she looked like she was ready to party.

“Hey pretty girl, tonight we are going to have some dinner, some fun and then some fun. You ready?” It was hard for Bailey to look at Liam; he had known him for so long and he really didn’t want to speak up. It would only draw more attention to him, Bailey could just imagine as he spoke up Chuck would snap his fingers and say “Bailey is that you?” So instead he looked away from Liam and nodded his head. A good girl is seen and not heard. The second reason he didn’t want to look at Liam was because the way he was dressed made him look like some anime protagonist. Tight jeans tucked into his mid calf boots, an untucked white button up shirt that had a little chain going across the shirt color on skull pins. He was even wearing leather bracers.

When they stepped outside Bailey was unhappily led by Liam who seemed to immediately take possession of him by putting his hand on his lower back. Aunt Megan locked the house while he was taken to Chuck’s four door Silverado truck. Bailey noted Liam’s… his old motorcycle was nowhere in sight. “Like where is your motorcycle?”

Liam gave his date a little wink as he helped her step up into the back seat of his brother's truck that he recently cleaned out for him. “We swung by the restaurant first and dropped it off, that way we can leave directly from there to the party. Don’t worry baby, I have thought of everything.” One of us has to, a ditzy girl like you probably doesn’t think of much. He thought to himself noticing she hadn’t brought a purse, and that meant she was ditzier than he thought or had already expected him to take care of everything.

When everyone was in the car Megan looked in the back seat and gave Bailey a smile, seeing Liam sitting in the middle so he could be up against the feminized man. She frowned for a second, not at seeing Liam have one arm draped around Bailey’s shoulder and the other sitting on the smooth skin of her thigh. No it was how her niece had forgotten to get her purse when she came to greet the boys. “Pumpkin.” She curled her finger beckoning Bailey closer so that she could whisper. “You forgot your purse, go get it and while you are in there put a few condoms in there just in case. You will find a box I bought on my dresser.” She loved seeing Bailey’s eyes go wide, but she didn’t say another word other than to hand Bailey the house key.

“She will be right back, she just forgets things now and then.” Megan could see Liam smile as he watched her strut back up to the house, both men were close enough to hear her whisper to Bailey. She could imagine Liam trying to talk Bailey into sex, pushing her like Bailey pushed others and having to actively try to convince Liam that what she really wanted to do was blow him. Tonight Bailey was going to suck her old friends cock. Before this summer was over she was going to make sure Bailey could deepthroat a banana and suck it right out of the peel and even still she bet Bailey would have had his dick sucked more more often then he sucked one with how often Bailey cheated on her sister.

In the house Bailey picked up his small black leather purse with the fake gold chain strap and moved to Aunt Megan’s bedroom. Sure enough a box of brand new condoms was sitting there, he really didn’t want to grab them, but if he didn’t he wouldn’t be following directions. A good girl is always obedient. He thought as he ripped open the box and pulled two free. It was odd looking at them in his hand, with the long nails it looked so much like a girl's hand and if a girl was holding condoms where he could see it that meant only one thing and that one thing caused his manhood to start to get a little chubby. “Simmer down, no one is using these.” Instead of putting them into his purse he dropped them into the trash can in the kitchen and slid a paper plate over them. The last thing he wanted was Liam to see them when he was touching up his makeup and giving him any ideas. Aunt Megan wasn’t going to find out and even if she did it would be worth the consequences. Bailey gave one last look at the trash can before he walked away, second guessing himself. A good girl is always obedient. Despite himself he took them back out of the trash can and put them into his purse, making sure they were under his cell phone in the small container.

“Get everything you need?” Liam asked as Bailey climbed back into the backseat. Bailey glanced at his Aunt in the front. “I like can’t believe I almost forgot my purse, I would like totally forget my head if it wasn’t attached. Gosh I hope you don’t like think I’m one of those girls that they make those blonde jokes about.” He needed to play in character, the more he acted like this the less likely they were to see a connection to himself and how he looked now.

“I would never make a joke at your expense, I know you aren’t one of those dumb blondes. After all you were smart enough to go on a date with me.” Liam couldn’t see the eyeroll of both his brother and Megan. “I will tell you one of my favorites though. Why can’t a blonde dial 911?” With Liam looking at him intently Bailey shifted his gaze down to his lap, where one of his hands rested while the other was playing with the end of his hair. He hadn’t heard this one before, but he was sure it wasn’t any better than the scratch and sniff sticker at the bottom of a pool. He was ready to tell Liam that everyone can dial that number, but the moment had passed. With him looking away Liam figured she didn’t have an answer to the question.

“Because they can’t find the eleven key.” Without thinking about it Bailey retorted. “Like there is no eleven key.” Liam started laughing, not loudly, but still laughing at his date’s response and he could hear her Aunt getting a kick out of the joke or at least how Bailey reacted to it. “I know.. We all know, you have to hit the one key twice babe.”

“Blonde jokes.” Megan’s words caught Liam’s attention and when he looked at her she was pointing to her own hair. He held up his hands in a placating manner to let her know he heard her. “I have more jokes than those.” Liam gave a squeeze to Bailey’s shoulder.

“A lady had been taking golf lessons and was playing her very first round of golf when she was attacked by a bee. In pain she couldn’t play anymore and went back to the clubhouse to see a medic. Coming inside she saw her instructor and he asked her why she was back so soon. The woman said how she was stung by a bee and when he asked her where, she told him between the first and second hole. He told her Sounds like your stance was too wide.”

Stance was too wide, Bailey let out a giggle at the silly joke, but Megan did not. “How about you Charles, do you have any jokes?” Chuck looked in the rear view mirror at his brother and then glanced to his beautiful date. “I like to think of myself as the strong silent type, I like to leave putting one’s foot in the mouth to my brother.”

“Bailey liked it, she has good taste.” Liam said as he tickled his date's side, happy to hear her giggle at his touch. “I have a little joke for you, see how you like it.” Liam motioned for Megan to continue.

Megan looked Liam dead in the eye, smiling as she talked. “What are the four words which are a sure fire way to demolish a man's ego?”

“What’s that?” Megan’s smile grew just slightly. “Close and I would say the same ballpark. Imagine if Bailey said to you, Is… it… in… yet…” Chuck burst out laughing, only for a second before he tried to cover it up with coughing. He knew his brother was not endowed, not that he had his brother hard, but it is hard not to see things in the shower at the gym, but Megan had no real way of knowing that other then guessing from his brothers short stature.

“Hahaha.” Liam gave the older women a mock laugh, while Bailey sat quietly thinking how that was a little mean spirited. He wasn’t the biggest guy in the world, and while boys could be mean in the locker room, no girl had ever said something like that, still it cut him. Especially with how his dick was for all purposes nonexistent if someone looked right now. “I will have you know most women don’t actually like those huge dicks people say they like.”

“Oh? Have a lot of experience with big dicks? Or just talking about them?” Megan said raising her eyebrow.

“Peace, peace. I think Liam has learned his lesson, let's not embarrass him in front of his date.” Chuck said reaching over to take Megan’s hand in his own. “Bailey, my brother has a good heart, he just hasn’t had enough experience with a girl who won't take his shit. If you take after your beautiful and amazing aunt you can whip him into shape and find a good man there.” Upset at both the people in the front seat Liam already knew Bailey was nothing like the older woman other than them both being sexy. Bailey was timid, submissive even and if any whipping got done it was him to her, maybe he would even slap her face a little with his dick before he let her have what she wanted. Liam gave Bailey a little wink before leaning in and pressing his lips to hers. Thrilled at the first of many, many kisses to come.