Rose
Previously on Rose: Lonely, quiet, and unlucky in love Ryan Wong is asked a favor by his roommate and friend Judy Chan. Judy wants Ryan to help her become more sexually adventurous or in her words: "How to be a slut." After a night of passion and experimentation, Ryan is left unsatisfied and confused about his own personal feelings for Judy as well as worried that he may have taken things too far. After a day spent with friends, Ryan agrees to be set up on a date with Cassie's friend, Emma. Ryan spends the night having dinner with Judy and clarifying their situation having sex and spending the night together. An arrangement is made.
This is where we pick up on our story.
Ch. 2 The List
As a man, there are few pleasures greater than waking up to a blowjob. Judy had surprised me this morning. It had been four days since we had come to our little agreement. Since then, we had mostly reverted to our roommates/friends relationship paradigm. The only thing that had changed was that we had started spending more time with each other. We ate dinner, watched movies, and even cooked together almost every day. Neither one of us had mentioned the sex nor Judy's desire to 'become a slut.' Hell, we hadn't even been intimate, except for the occasional cuddle. This was a most welcome surprise. I pulled the covers off of me to find Judy between my legs. Her mouth wrapped around my cock. Her tongue massaging my shaft as she bobbed her head up and down on my length. Fuck. She was really starting to come into her own as a cocksucker.
"Mmm, g'morning." I said, still half asleep, though that feeling was fading. Hard to be asleep when your gorgeous roommate has her mouth wrapped around your cock.
"Morning." Judy said, disengaging herself from my cock for a second and diving right back in. She went to licking my balls while her right hand jacked my cock. Her saliva providing the lube needed for her hand to slide across my cock with ease. I moaned with pleasure, while Judy delicately licked my sack. Fuck. I didn't teach her this move. She was getting bolder and bolder with me.
"Fuck." I groaned, "Gonna cum."
Judy took that as a signal and accelerated the speed of her strokes. "Yeah baby, cum for me." She said, taking a playful lick of my cock head. "Give me your fucking cum. Cover my slutty face with your cum. I want to fucking taste it in my mouth."
It didn't take much dirty talk from Judy to get me to cum. My cock quivered with pleasure as my orgasm tore out of me. Judy must have sensed it because she immediately aimed my cock at her face and let my cum shoot out all over her face. The first shot streaked across her right cheek and landed in the middle of her forehead. The second hit her right on the nose and the last shot nailing her forehead again.
"Mmm," Judy moaned giving my cockhead a light peck. "Thanks."
"Thank you." I said with a grin, I sat up and covered my softening cock with my blanket. "What prompted this?"
"Always wanted to try waking someone up with a blowjob." Judy said with a shrug. She took a finger and wiped the cum off of her face. She grabbed a box of tissues that she had left a top of my bed and cleaned her fingers. "I figured, now was a good time to try that, with our little agreement and all."
Made sense.
"Anything else, you've been meaning to try?" I asked
"What do you mean?" Judy said
"Well, since you want more sexual experience, I figure now would be the right time for you to experiment."
Judy blinked as if she hadn't thought about that. "You make a good point. So how should we do this?"
"How about you make a list of things that you'd like to try and we'll try to work our way down the list together?" I suggested.
"Yeah, I like that idea." She said nodding her head excitedly. There was a twinkle of eager anticipation in her eyes. "I'll start working on it today." She crawled over to me and gave me a quick kiss on my cheek before heading out.
Well, that was unexpected. I laid back down on my bed. Things couldn't get any more complicated. A buzzing at my side alerted me that I had received a message. I grabbed my phone and turned on my texting app to find a message from an unknown number.
Hi Ryan, this is Emma, Cassie's friend. She said that we should go out. Call me <3
Or maybe they could...
I put my hands over my face, rubbed my eyes and got out of bed.
I needed something to distract me.
***
One of the benefits of being a software engineer is the ability to work from home. The company that I work for is a relatively large software firm, which means that I'm allowed to work from home two days out of the week. Today was one of those days meaning that I was able to get in a quick jog around the neighborhood. I was just getting back in when I ran into Judy about to head out the door. To my surprise, she was wearing a long white dress decorated with yellow sunflowers, along with a pair of red sneakers. Her hair was down and held back with a hairband.
Stylish. Especially when you consider that her normal attire usually consisted of a pair of jeans and a hoodie bought from the university bookstore.
"Wow." I said "You look nice today."
Judy smiled warmly. "Thanks, I've got a busy day today. But I wanted to try something different."
"Gonna be a long day?" I asked, it was more a rhetorical question than anything else. I knew that Judy TA'ed for a few undergrad classes at the university and held office hours today. That, along with writing her master's thesis, grading papers, and holding office hours meant that a good chunk of her time was usually spent at the university.
"Yep, see you tonight?" Judy asked.
"Definitely," I said with a grin. Since coming to our little "arrangement", Judy and I had started eating dinner together. It was nice. "I'll make dinner tonight."
"You too." Judy said and to my surprise, she walked over and gave me a quick kiss before walking out the front door.
**
I spent the majority of the day, working on one of the projects that my company had assigned me. I tended to work on the dining room table whenever I worked from home. A cup of coffee and a large water bottle, usually reserved for hikes, sat next to my laptop along with an pair of noise cancelling headphones. I spent the next three and a half hours, writing, testing, and debugging code. I only stopped only to use the bathroom, drink water or grab a snack or two. The harsh, energetic beats of dubstep booming in my ears through my headphones as I worked. Around 11:30am, right when I was finally satisfied with how my code was running, I got a text from Jack.
Lunch?
I instantly felt my stomach rumble in anticipation. I didn't know how hungry I actually was until the thought of food was planted into my head. It's amazing how a single word, phrase or even sound can prompt such a physiological response from our brains. Pavlov really was onto something.
I picked up my phone and texted back.
Where?
A beat and a moment.
I'm craving burgers and fries. Driftwood Diner?
Burgers did sound good and I had been working long enough. I didn't have any afternoon meetings meaning that I could take it easy for the day.
I'm down, 30 minutes? I typed and sent it.
Jack replied after another minute. Yup.
I smiled. It was amazing that 15 years of friendship could result in a nearly binary form of communication. I closed my laptop, satisfied with the amount of work that I had completed this morning and went to get ready. I washed my coffee cup, finished the rest of my water and got ready to ride out.
Judy and I live on the fifth floor of our apartment complex, a short drive away from the college town, Ingleside, where Judy worked. The town was known for having rowdy parties, especially after finals week, and good restaurants. Driftwood Diner was located at the very heart of Ingleside's downtown area. I parked my motorcycle on the street and walked in to find both Jack and Jane waiting for me on the patio.
Jane Olson was Jack's new girlfriend, and before that, his closest female friend. She was pretty and petite with pale skin, and beautiful brown eyes. Presently she was wearing a pair of jeans alongside a forest green blouse that hung off of her arms exposing her pretty shoulders. She gave me a bright smile when she saw me and waved me over with her hands.
Jack grinned when he spotted me and got up to give me a hug as I approached the table.
"What's up, brother." Jack said.
"Just work," I said with a grin. "You didn't tell me that I was going to be playing third wheel."
"Hazards of being single, dude."
"Fair enough." I took a seat at a table and gave Jane a grin. "Good to see you again. Have you guys ordered yet?"
"Waiting for you." Jane replied, and as if on command, a pretty blonde waitress wearing a tight black tank top and a pair of daisy dukes came by with menus for us.
I ordered a burger with a spinach salad and a glass of house made lemonade. Jane ordered a burger topped with mushrooms and a salad. Jack ordered a cheeseburger and fries with a coke and lemon wedge. We spent the next 15 minutes talking and joking around while we waited for our food. I wasn't particularly close with Jane, but I could tell how happy she made Jack. That was all that mattered to me. Plus, it was entertaining watching Jane poke at Jack's buttons. It was kind of nice being the third wheel, but not feeling like the third wheel. Jack and Jane made me feel like a part of the gang.
"So, settle this debate for me." Jane said after a moment. "Ocarina of Time or Skyward Sword?"
I blinked, out of all the things that I had expected to come up during this lunch hangout, the subject of Legend of Zelda was not on the list. "Ocarina of Time," I replied. "The story just feels so well written and engaging. My older cousin bought an N64 back in college just so he could play it."
"See told you!" Jack said teasingly.
"Boo," Jane pouted, "Breath of the Wild will always be my top."
"That's just because that was the first one you tried." Jack countered.
We laughed and talked. Jack may be with Jane, but at no point did I feel left out of the conversation. It was nice. We talked until a waitress dropped off our food. My burger was still steaming hot, a sliced tomato and two lettuce leaves on the side. I grabbed the fork, scooped some spinach onto my burger along with the tomato and lettuce and dug in. The vinaigrette dressing on the spinach contrasted well with the burger's juiciness. We ate and chatted for a bit longer, topics ranging from sports to recent movies, before Jane brought up the dreaded topic of my love life.
