The First 100 Kisses: Practice Makes Perfect

by Danielle Bannister

  Liam seemed embarrassed. No, not embarrassed. Ashamed.

  “I suppose I have more use for the towelettes than I do condoms,” he said, pushing a chip on his plate.

  He looked like a puppy in a shelter nobody wanted. My heart broke for him.

  “I’m sorry,” I said, genuinely upset I’d inadvertently offended him. “But that is what we’re working toward fixing. When we are done with you, you’ll be able to pin Angel against the wall and…” I saw his face redden and decided to take mercy on him. “What I’m trying to say,” I reached over and gave his hand a squeeze, “Is thanks for always being prepared for whatever life throws at me.”

  I felt his hand squeeze around mine. “And thank you for helping with the areas that I don’t know how to maneuver.”

  “Yet,” I said. He’d get there. I had faith. “So, tell me. Have you heard from her lately?”

  Liam seemed far away, but he nodded. “She texted me last night.”

  “Ack, dish! What did she say?” How dare he leave me in the dark about this? “Spill it. I want the blow-by-blow.”

  “She was just confirming dinner reservations. We’re going to try out that new Italian place on State Street.”

  “But you hate Italian,” I said.

  “I do, but apparently she enjoys it.”

  While I was annoyed he wasn’t honest with her about what he liked I decided to play up the positives. “A fancy dinner is good. It means she’s totally interested in you.”

  He cocked his head. “It does? How?”

  I took a sip of my soup. “Well,” I said around my spoon like the classy lady that I am, “let me ask you this. Was it her idea or yours to go to there for dinner?”

  “Hers.”

  “There ya go,” I said. “She likes you.”

  “Explain, please.”

  I put down my spoon.

  “Think about it. If she wasn’t interested in something serious with you, she would have suggested coffee. In broad daylight in case you turned out to be a nut job. That’s the norm with a first date. It’s safer that way, easy to escape. One cup of coffee and you’re free. Now, because she knows you, she could have suggested you go for drinks, which means she doesn’t think you’re a perv and there is potential to continue the evening after, but it’s still socially acceptable to leave after only one drink.”

  Liam shifted in his seat. “Okay. So, what does dinner mean?”

  “Ah, well, dinner means that she’s prepared to spend several hours with you. A woman who suggests going to dinner with her is saying, unless you blow it, she is all in.”

  “All in?”

  “You could close the deal at dinner if you play your cards right.”

  Liam pushed back in his chair.

  “I’m not ready for that, am I?” There was sincere panic on his face.

  “Relax,” I said, picking my wrap back up. “She’s not going south of the elastic band border this weekend. We’re just going to make her wish she could.”

  He let out a breath. “Right. Okay.” He began to drum his thumb on the table. His sandwich was only half eaten but I could tell his mind was no longer on food. He was in full panic mode. I waved my hand to the waiter.

  “Can we get this to go? My friend here has to get to a practice.” I smirked at him, but he seemed relieved that I’d picked up on his worry.

  “Before we head home, there is one final stop we have to make,” I said once we were outside.

  “Where?”

  “Just to the drug store. We need to get you some condoms.”

  Liam stopped walking.

  “Why?” I heard him say from behind me. “You said we wouldn’t be…”

  I turned and gestured with my eyes that he get his skinny ass beside me. He sighed, shoved his hands in his pockets, but obeyed.

  “It’s all part of the illusion,” I said. “You don’t have to use them, but you absolutely should have some on hand. You’re an adult, Liam. It’s irresponsible not to have condoms at your age. She would think it’s weird if you didn’t have any.”

  That sold him. Because of his social awkwardness, he was always afraid he wasn’t doing things the “normal” way. If a man in his 30s was supposed to have condoms in his drawer, then that is what he’d do.

  On that conviction, he let me drag him into the store and down the contraception aisle, where I picked up some pads that were on sale, much to his utter chagrin.

  “Okay, what size are you?” I asked. He was looking down the aisle, anxious that someone one would see us. “We’re not robbing a bank, Liam. Calm down. Now, what size? I suggest you get something ribbed.” I wiggled my eyebrows up and down, but Liam seemed horrified.

  “Size?” he said. “I don’t know. Just pick something.”

  I frowned. “Liam, Liam, Liam. You can’t just pick any old random rubber and expect it to fit. Condoms are not an all-size fit all.” It was clear he didn’t have any idea about this fact and was embarrassed.

  “Okay… um. Let me ask you this,” I whispered, “About how wide are you?” Every guy knew their length. Down to the millimeter, but it was the girth that mattered most with condoms. Too tight and they popped off like a top. Too loose, and well, hello pregnancy and STDs.

  “I don’t know. Can we just get one and go?”

  “Liam, this is important stuff.” I leaned in close. When you hold it in your hands, do your fingers overlap or not touch? Show me,” I said.

  Liam gaped at me. “I am not going to show you my penis in the drug store!” he hissed.

  “Oh my god. I’m not asking you to whip it out. Just mime it. With your hand.”

  He ground his teeth, but he complied. Very quickly. This told me two very important things. One, he jerked off, because he knew exactly the right position to hold his cock. I did worry for a moment that I was going to have to teach him that, too. It was a relief that I didn’t. But two, and more importantly, it told me what size he was. Goldilocks size—not too big, not too small.

  “Okay. Let’s go with the Trojan Groove. A personal favorite.” I couldn’t help but smile as I walked out of the aisle. Liam quickly followed but left before I paid. The chicken.

  Outside, he was waiting for me. “Can we go home now?” he asked.

  “Yes,” I promised. I had properly embarrassed him and protected him from getting Angel preggos, (again). I had done my best friend duty.

  “Can I ask you something, Chloe?”

  “Ask away,” I said swinging the bag in the hand that wasn’t holding his.

  “How important is size to a woman?”

  The quintessential fear of men. “Honestly?”

  “Yes, please.”

  “When you’re with the right person, it doesn’t matter. Seriously. You find a way to make sexual pleasure happen for each partner. On face value, the size of a man’s penis, his girth, really, is what is at play for a woman. The wider he is, the more stimuli he’ll bring to the clitoris. He can be as long as a truck, but if he’s thin, it doesn’t do her any favors. But that’s when you exchange oral sex or do more fingering for her. Sex is give and take.” This was way too much for Liam to handle, but he wanted an honest answer.

  “And what is a good-sized girth?” he asked.

  I squeezed his hand knowing exactly what he was asking.

  “Your penis will make Angel very happy one day.”

  Despite the discomfort of the conversation, he smiled. From our make out sessions I’d already figured out he was a good 7-8 inches based on the feel of his erection, but now that I knew his girth, he was going to make that woman howl. Lucky bitch.

  Back at the apartment, Liam shrugged out of his jacket and draped it along with his scarf on the back of my couch, then went to stand in the spot where we had done our first kisses. Clearly, he was ready for his lesson to begin again. His ego was inflated so I felt the need to knock it down a notch or ten.

  “Teeth first, then we practice. I don’t want any of that gross-ass avocado spread you ha
d on your BLT in my mouth.”

  “Avocado is very good for you,” he tried to rationalize.

  “Yes, I’m sure it is, but if it’s all the same, I’d rather not suck it out of your teeth.”

  “Fair enough,” he conceded after a moment.

  “Oh, and take your condoms. Put them in your nightstand.”

  I removed my pads from the bag then handed the rest to him. He took it, reluctantly, and held it out from his body like it was a bag of poop.

  “Back here with peppermint fresh breath in five, mister.”

  Obeying, he went back to his place. That’s when I noticed that his cell phone was poking out of his jacket pocket. Unable to resist, I picked it up. It wasn’t password protected. Oh, Liam. Have I taught you nothing? It was none of my business, but I was dying to know exactly what Angel said to him about the date. I looked at her last message to him.

  -Can’t wait to catch up over dinner Friday night. It will be fun to reminisce. I hate to admit it, but I kept all your old letters. I still read them from time to time. I’m glad we’ll have time to reconnect. -

  Gag me. She was totally saying she’d made a huge ass mistake all those years ago. Yeah, you did. I scrolled down to see his reply.

  -Great. See you at 7.-

  “That’s it?” He didn’t seriously stop the conversation there, did he? But this was Liam. He didn’t know how to flirt. I sighed and opted to help him out, despite my hatred for Angel.

  -Sorry I was brief before. I was in a meeting. I’m counting down the minutes until we meet again. I have missed you, too. Perhaps dinner can lead to drinks? -

  I read it over a few times making sure I sounded proper enough to sound like Liam but still hint that he was game if she was, and she totally would be.

  Liam walked in just then and I hit send, making sure to give him my best Cheshire cat grin.

  “Why do you have my phone?” Liam asked.

  Smirking, I took his phone and shoved it down my bra and walked to my spot, hopping on the counter, hooking my finger at him.

  “Come get your phone and find out.”

  Touch was going to be a huge hurdle for him, and what better way to motivate him then by having him go after something he wanted? Not to mention, I’d get the benefit of being felt up. Really a win-win. I could see him start to object, but quickly realized this was to be part of his ‘training.’ Ever the good student, he listened to his teacher and agreed to instruction.

  “Fine,” he said, walking over to his spot. He reached his hand out like he was going to simply grab the phone from out of my shirt.

  “Um. No. You don’t just lunge at a woman like that. You have to warm her up. Make sure she wants you to put your hands on her.” I leaned back and licked my lips. “If you want the phone, you’ll have to kiss your way there. Start with the kiss, then go for the boob.” I looked down at the phone very easily outlined against my T-shirt.

  He started to come in fast, but I held up my hand. “Slow and steady will win this race, and Angel’s desires. Remember…tease her. Don’t give it all to her on this first kiss. We want her to come back for seconds,” I whispered.

  Liam backed off, considered, then started his approach again, much more slowly like I’d taught him.

  “That’s right,” I said. “The ‘slow burn.’” He got close, nose to nose, and paused. My heart kicked into high gear being this close to him. “That’s right,” I purred. “Hover there a moment. Look into her eyes.” He did and my insides shook. I swallowed once. “Make her wonder if you are going to pull away or go in for the kiss. It’s a dance, and you are in the lead.”

  He stood there a moment as his breathing picked up. Mine did too. This was scary shit even when you knew what you were doing. It didn’t matter that I understood the kiss meant nothing, the hormones did not. They reacted, not caring in the least that the man I was about to kiss was my best friend.

  When his nose brushed alongside mine, I let out a soft moan.

  “Oh, that’s good. Do that Friday,” I whispered.

  “What now?” I could hear that he was nervous, and probably wanted to pull away or start over, but he was forcing himself to stay in the game.

  “Put your hand on her face. Cup her jaw gently so you can position me—er—her, right where you want her.”

  He did, and I felt myself lean into his hand. Just like Angel would. She would be helpless not to. My lips parted slightly in anticipation of his touch. I could feel his breath hot against my lips. His erection spring up against me and I knew the fucker was going to bolt from embarrassment, so I latched onto his waist with my legs, locking him in place. Unable to wait for to him to refocus back on the kiss and not his erection, I kissed him instead.

  I could feel his shock as I took the lead, but there was no way this jackass was going to deny me a kiss after a build up like that. I knew Angel wouldn’t, either. This would be a lesson within a lesson. Don’t be surprised when your dance partner takes over. Kissing was give and take. He needed to know that and not freak out if, no, when, Angel took over. And she would. She would grow hungry in his arms. This was for his own good. Liam had to learn how to deal with women like her. It had nothing at all to do with the fact that he really tasted amazing on my lips.

  Once I dug my fingers into his hair, he seemed to relax. His lips softened. He moved his hand down from my face to the nape of my neck on his own accord. Yes, do that. I was just about to break the kiss to tell him to grab ahold of my hair, but shocking me, he did it on his own.

  He yanked my hair so hard it broke the kiss. I gasped and then gasped again when he started kissing my neck instead. It was hot as fuck.

  “Jesus, Liam,” I panted.

  He stopped kissing and let me go.

  “Did I do it wrong? I see guys do that on TV a lot…I thought it would be good. I’m sorry. Did I hurt you?”

  “No, that was a cry of pleasure,” I said, breathless. “Liam, that was fucking awesome.”

  He smiled. “Really?”

  “Oh my god, yes. You pull that move with Angel and she won’t know what hit her.”

  “Right. Okay.” He seemed pleased with himself. “But how do I turn the heat down afterward?”

  “Well,” I said, adjusting the cell phone under the cup of my bra to make this more interesting. “That answer doesn’t come until you get the cell phone…so let’s work on some boob action.”

  He cleared his throat. “Define ‘boob action.’”

  I smiled, loving how uncomfortable he looked. “Well, for right now, it means obtaining your cell phone. For Angel, it will mean a nice, solid cupping, perhaps a stroke of the nipple with the back of your thumb for good measure.”

  His eyes grew wide.

  “You mean, touch her actual breast? Skin to skin?”

  I nodded. “Yep. And, shucks, darn, I think you’ll have to do the same to me as I don’t see any other way around this situation.” I looked down at my chest. “My bra is really tight. You’re going to have to go under it to get what you want.”

  I made my voice as husky as I could to drive him as wild as I knew Angel would make him. This training was about testing his boundaries and making himself comfortable in his own skin. It had absolutely nothing to do with the fact that I really needed him to touch me. Nothing. At. All.

  I saw Liam assessing the ‘situation.’ He was calculating in his mind a way to remove the cell phone from my bra without actually touching my bare breast.

  “Don’t math your way out of this one, Liam. You need to know what touching a breast is like, so you aren’t hyperventilating when it comes time to do it with Angel.”

  “But is this sort of thing really needed for the first date? That seems a bit much…”

  “We’re teasing her, remember? We want her to come back for a second date. She needs to know she can expect a good time with you, but more importantly, that you’ll be respectful and not demand anything more. You’re just giving her a taste of your moves, Liam.”

&n
bsp; “But I don’t have any moves! You’ve been telling me what to do on this first date, but what do I do on that second date, Chloe? I think you are forgetting about that part!”

  I waved his panic away.

  “We’ll have a whole week, maybe even two if you’re smart…that buys you time and makes her more anxious to see you. Don’t worry. I’m not going to leave you high and dry, Liam. Trust me. I want this to work out for you.”

  Or at least, I keep telling myself that.

  Liam took a few calming breaths. His silver-blue eyes narrowed as he seemed to be refocusing his energy on the task at hand.

  “Get the cell phone,” he muttered.

  “And flick the nipple,” I grinned.

  His face scrunched up, not in disgust, though some might read it way. It took me years to realize that he wasn’t an asshole. That was just his face. So, I knew the look he wore wasn’t from not wanting to touch my breast, but a look of confusion.

  “I’m not precisely sure I know what you mean by that. Flick it how?” he asked.

  I hooked my finger to get him to come closer. “Like this,” I said, trying to reach my hand under his shirt to show him. His hand jutted out and stopped me before I could.

  “I’m not ready for that sort of touch yet,” he said quietly.

  Boundaries. He had them. I didn’t. Clearly.

  “Okay,” I said, trying to keep the mood going. “Is over the shirt alright?”

  He thought about it, then nodded.

  I could tell that he was nervous but trying to remain calm. Slowly, I ran my hand up his torso, which I could tell was hairy based on the texture through the fabric. Why was that a turn on? I didn’t like guys with hairy chests. Forcing myself to focus, I cupped his peck gently, which was more formed than his loose-fitting shirts let on. He was no Dwayne ‘The Rock’ Johnson, but he was no Pee Wee Herman, either.

  “You cup the breast like this,” I said, “though you’ll have more to hold than I do. Give it a few gentle squeezes,” I demonstrated. He swallowed once but stayed focused. “Then, with your thumb, graze it over her nipple, which will be nice and erect by this point. It’s a super sensitive spot.” I rubbed my thumb against his own pebbled nipple, which was visible through the shirt. His eyes closed with seeming delight. Was I turning him on? The idea got me all hot and bothered. I withdrew my hand reluctantly, even though my hands begged to linger.