Siena Ch. 01: Directing

I was walking with Siena, talking about basically nothing when she blurted out, "I have a problem with a guy I am seeing."

Her normal bubbly self was a little subdued. I looked over to her, searching for a facial expression, but she looked off in the distance away from me.

"What's up?" I asked, possibilities already running through my mind.

"Um, hmm, well, I met this guy. He is a geek, Like for real," she said. The flow of the conversation was bit slower, like she was picking her words.

"Oh that's awesome, Siena," I said. "You have been looking for a nerd. Sounds like a good match. So what's the problem?"

"Well, we have seen each other four times now. The first time, we just went out to dinner. The second time, we went for a walk in the woods. The last couple of times, we went to my place."

I raised my eyebrows at her. "Oh, so, is there a problem in the sack? Is that it?"

She laughed. "I like how you just cut to the chase and know me so well." She paused. "No, that's the thing. It's not that he's bad at all." One more hesitation, and she dropped on me, "I have not even kissed him." She said it almost in a whisper.

I stopped. She walked a couple of paces before stopping too. I stared at her, mouth agape. "He hasn't kissed you?" I asked.

She shook her head.

I was stunned. "Well, why the fuck not?"

"And now you understand my problem," Siena said. "I keep giving him the clear signals. Touch his arm, stroke his hand, lean into him when I sit next to him, but he hasn't so much as touched me unless I initiate."

"Hmmm, that is a problem," I say. "But, you have never been shy about that. Just kiss him, rip off his clothes, and climb on top. I don't think he's going to turn you down."

Siena sighed. "I am in control so much of my day. I have work responsibilities and mom responsibilities. I just don't want to have to be in control on this. I want him to sneak into my bed, hold me down, and fuck the shit out of me."

It is the nature of our friendship that these words did not shock me. I did chuckle a bit.

We walked in silence for awhile, just enjoying the outside and each other's company. I snuck a look at her ass as she did and shook my head. "What kind of idiot passes up the opportunity to tap that?," I thought.

Nearing the end of our walk, I started to develop a plan. I mulled it over in my mind, thinking over the details. After fleshing it out a bit, I said to Siena, "Let's go around the block again, I think I have an idea for you."

She glanced up at me and gave me a smile. "Ya?"

"So, what if I...", I started, and then outlined my thoughts to her. We ended up needing to circle the block twice just to convey the details.

"What do you think?" I asked.

"I love it," she said. "When do we do this?"

I laughed at how eager she was. "I am free this Friday night. Can you set it up for then?"

"I think so," she said.

I stopped and hugged her. "This changes nothing between us, ok?"

She looked kind of offended, "Of course!"

"Good, then I will see you Friday."

"What should I wear?" she said.

"Hmmm... wear that dress that you like that shows off your ass. But, unlike how you normally roll, throw on some panties and a bra. We are going to need those."

Chuckling, she shook her head. "Ok."

"Later, hideous face."

"Later, nerd with no game."

--------------

Friday night came and I texted Siena, "Everything all set?"

"Yep. Come over at 8."

I waited the three years in between, which was actually just two hours. I was buzzed into the outside door and walked into her apartment without knocking. She was hugging me almost before I was through the door, which was not unusual. Her flowery dress hugged her in all the right places, and I saw that she had a lacy bra from my vantage point. She caught me looking and grinned. I was always so obvious.

A tall thin man stood up from a kitchen chair. He just looked at us with a slightly puzzled expression. An awkward silence was broken by Siena saying, "Derek, this is Richard, Richard this is Derek, my friend."

I shook Richards's hand firmly. "Nice to meet you," I said, noticing how his handshake was tentative.

There was a sofa in the living room that sat three, a love seat that sat two, and a recliner. I purposely picked the three seat sofa and sat dead in the middle. Siena sat down directly across from me on the love seat. Richard looked at the couch, at the loveseat, at the recliner, and made the only logical choice. He sat beside Siena.

"So, what are you guys up to tonight," I asked.

I could almost read Richard's mind as he looked over at me. "Who is this guy? Why is he here? When will he leave?" were my guesses.

Siena glanced at him and said, "Um, not too much. Maybe watch a movie. Just hang out."

We just started to chat about stuff. Nothing very deep or personal. Richard kept looking back and forth at us, wondering, undoubtably, how long I would hang out. I almost felt sorry for him. After awhile, he just sort of sat back and looked zoned out.

I gave Siena a slight nod. She nodded back.

"So, Richard, how long have you been seeing Siena?"

Richard did a sort of double take. It took him a couple of seconds to answer. "Um, this is like our fifth date. I think our first one was about a month ago." He looked over at her, but she did not have a comment.

"Oh, wow," I said. "She is a good girl. And a great kisser."

Richard's mouth just fell open. "Umm".

Siena giggled. It was such a cute sound.

I smiled, "Hey, no worries Richard, Siena and I are just kissing flirty friends. I am happily married."

Richard seemed relieved, so I had to throw out there, "Not that I wouldn't fuck the crap out of her if I could."

"Derek!" Siena exclaimed, laughing. Richard's mouth was open, clearly wondering how serious I was and if he should be doing something about the statement.

I chuckled, "Just keeping it real."

Richard laughed awkwardly, clearly not knowing if I were joking or not. He cleared his throat. "Um, I wouldn't know if she was a good kisser, we haven't kissed yet."

I gaped at him. I tried to recall my shock at hearing this exact thing when Siena told me so that my reaction was real. "Say what..?"

Everyone kind of froze. Richard had his eyes cast downward. I winked at Siena and she hid a smile behind her hand.

"Dude, man, what's up with that?," I asked.

Richard was making eye contact with plants, lamps, furniture... everything except for me. "I dunno," he mumbled.

I let the silence linger for a minute. "Maybe I can help," I said softly, almost too low to hear. Richard's ear perked, like he wasn't sure that I said what I said and didn't know how to react.

I shook my head. "Alexa!", I paused. "Please set the lights to dim and play R&B music. Volume 2". The lights came down and soft music began playing.

"So, Richard. Let's fix that, ok. Just lean over and give Siena a kiss." I said it with a moderate volume voice, but an edge of command to it.

His face turned red, he coughed, and he sought her eyes for confirmation. She just gazed back and waited, letting him come to her. He was poised, frozen in that moment.

"Go ahead, man." I assured him.

He leaned towards her, she turned her face so he had a clear lane. And he gave the barest peck on her lips before retreating back to his spot.

"Ok, ok, Richard, that's a start, I guess. But, really press your lips against hers. And count in your head to three." Again, I said it in a normal tone, but one that expected to be obeyed.

He went in for the kiss, but this time his lips pressed into hers and stayed. I could see Siena's chest rise and fall in response.

"Great, Richard, great!", I cheered as he broke the kiss. He blushed, but looked pleased.

"What do you think, Siena?" I asked

"That was good," she breathed, but with just the tiny bit of hesitation.

"See that Richard, Siena liked it. Did you hear just that little bit of uncertainty, though? Siena needs just a little more. So, this time when you kiss her, press your tongue into her mouth. Start out gentle, but get it moving. Let's see how it goes."

His face showed how uncertain he was. I had him off balance and he did not know how to react, how to figure out what was happening. I saw him shrug just the tiniest amount and then kiss Siena for the third time. But, now I could see his tongue active and in her mouth. Again, her body responded. I could tell that it was a bit all over the place, though.

"Hold on a sec, Richard," I said, moving across the room to be next to Siena on her other side. He disengaged, a starry look on his face. I guess he was enjoying this, which was good.

"You can't just jam your tongue into her mouth. You need to work it. Think about how you are trying to tease it forward, then build momentum, and then think about simulating oral sex. It is in all in the mind. Here, let me show you." I reached down and lifted Siena's chin, bending to reach her lips. My tongue darted out, and then I slowly, steadily pushed my tongue in and out of her mouth. I trapped her lip between mine, then pulled her to me using the back of her head. We stayed like that for almost a full minute and you could almost feel the tension in the air. When I broke the kiss, she gasped, a little breathless.

I crossed the room again, sitting down. Siena sat with a far away smile on her face. Richard seemed like he was trying to decide if he should be mad or whatever, so before he could decide that, I said, "Do you see? Now you give it a try. As you get into it, press in, use your hand to gently pull her. Think seductive thoughts."

Richard paused, "What is going on here?," he said out loud.

Siena pulled his head over and said, "Richard, it's ok, just go with it."

Another hesitation, a little shrug, and he was following my instructions. This time Siena lay back just a little and I could see her nipples through her shirt, trying to poke someone in the eye. They were getting into it, both of them, and I saw her taking turns driving into his mouth.

"Great," I said, "now stroke her hair, moving it away from her neck. As you make out, take an opportunity to kiss her neck. You can even use your tongue on it a little."

Richard stroked Siena's golden hair and broke their kiss long enough to kiss her neck. You could hear Siena moan just a little. "See, Richard, she likes that." Emboldened, Richard kissed more of her neck. Siena closed her eyes and leaned back even more. Her dress rode up to mid thigh, and I imagined she was getting quite aroused. Watching, I had to adjust my hard cock in my shorts. The mood music and lighting helped to maintain the spell.

"OK, man, have that hand stroking her hair touch her down her back. Use it to draw her closer as you kiss her again. Start to explore her body a little." It seemed some of Richard's hesitation was falling away as his hand started to move even before I stopped talking. This was going fabulously.

They made out in front of me, both of their hands roaming a bit more. Sometimes he would kiss her neck and sometimes he would kiss her lips. I let them work on their own for a couple and they broke off naturally. I think, honestly, they briefly forgot I was here.

The action was getting good when I asked, "Does anyone want a drink?".

Richard stood up, moving awkwardly. I could tell he was trying to hide his erection and was amused. I also rose and made no effort to hide how incredibly hard I was. Siena smirked.

"Sure," Siena said.

I grabbed a couple of beers in the fridge and passed them out. We drank and chatted for a bit, Richard still running his hands down Siena's back and her leaning on him. It was cute.

"Let's continue, Richard. Start by kissing her, running your hands through her hair and onto her shoulder. And, naturally as you can, slide your hand down her front until you are covering her breast through her shirt."

We were crossing a line here. What was before innocent was definitely drifting into the not so innocent category. We were all feeling a bit loose and buzzing from the drinks, but he looked a bit taken aback.

"Um, is that okay, Siena?" Richard asked.

She nodded and they started kissing. Richard got through the preamble, with the hand moving toward her breast, but hesitating to move it on. She kissed him enthusiastically, urging him. Finally, he covered her right breast, and she moaned into his mouth. I could feel a renewed stirring in my pants.

"Now, massage her breast through her shirt while you kiss her, slow at first," I said.

Richard hesitated again, seeking confirmation from me, and then at her, "Is that...," he began.

I interrupted him. "Hey, Siena, come with me in the other room for a sec."

Almost like she was waking up from a sleep, she blinked her eyes, stretched, and stood up. Still a bit confused, she following me into her bedroom and I closed the door, but kept it open just a crack.

Keeping my voice low, but not too low, I said, "So, how's it going today, Siena?"

Her confusion was written on her face. "Um, I am doing good. What's going on, Derek?"

"Has work been good? Things still super busy?" I asked.

The expression on her face was priceless. "Dude, what the heck?"

"Just another couple of seconds," I said, turning my watch towards me. "I think we're good now..."

"Ok, sounds good," I said a bit louder, opening the door and extending my arm for her to proceed me. She was moving back out when she stopped.

"Hey, you kissed me," she whispered.

I whispered back. "Ya, I did. Do you have a problem with that?"

She thought about it and shrugged. "I guess not."

"Great!", Derek said with a mischievous grin. "You can trust me,"

"Oh sure," she chuckled, "I do, Derek, with however this goes." We stopped whispering and went back into the living room. She sat down, a bemused grin on her face.

I sat across from them again and caught her eye. I winked at her and she visibly relaxed.

"So, Richard, Siena and I talked in the other room. She let me know what is ok for her to do, what's she's comfortable with, and most importantly, what's her line where she won't go," I peaked over at her, she mouthed, "We did?" and she was silently laughing to herself. I quickly looked away to avoid losing it.

"Anything I ask you to do from here, she is ok with." I studiously kept my eyes on Richard and did NOT glance over there. I could just see her sides heaving and I was barely holding it together.

Richard nodded.

I took a deep breath, calming myself. Siena got it together too. We both avoided each other's gaze as much as we could.

"Where were we? Oh yes, you were feeling her up through her shirt..."

This time Richard went almost immediately from kissing Siena to feeling her breast. I actually was a bit proud of him. There was kissing noises and little moans as she clearly enjoyed what he was doing. I watched as they progressed, and Richard moved his hand to her other breast and started to kneed that one through her shirt.

"Awesome, Richard. It is always a good idea to pay attention to both breasts and to vary it up so that you don't get stuck in monotony." I saw a smile from Siena and Richard continued what he was doing.

"OK, this is good. But, if you are kissing a girl like you are, Richard," I paused as he came up for air. "When it is going well, and you are feeling her up, and she's into it... you can go for unbuckling her bra. This is good way to get things moving to the next level."

I saw a momentary flash of anxiety when I mentioned "next level", so I plowed forward. "Reach behind her back and find her bra clasps. Siena's dress is a boon to you, because the scoop is low enough that you can see them."

Richard reached around, peering over Siena's shoulder to see the straps. He pulled on the bra straps, but they stubbornly stuck together.

"This is a common problem, Richard, especially the first time. The secret to unfastening a bra is to push the two sides together. Each bra generally has multiple hooks, so you want to think about pushing the loop away from the clasp."

I watched as Richard struggled. I could see Siena kinda losing patience.

I walked over and stood beside them again. I reached down and found his hands on her bra. "Push these together," I said, and he did. "Now, hold this one and angle this one towards her back, not away, see how the hook is." I saw that he did. And suddenly, it was unfastened. I quickly reached down and unfastened the second one for him one-handed. He was awed by it, and I smirked as I came back to my seat.

"Watch this trick, Richard." I said, nodding to Siena. "Siena, take your bra off."

Siena reached to her chest and pulled her bra straight out. Then, she pulled one strap down her arm. Richard watched fascinated at the process. Then she did the same with the other strap, and pulled the whole thing through the arm hole. "Tada!" she said and wiggled. You could see her braless breasts move in the dress, and I couldn't help laughing.

"Wow, that is a great trick," Richard said. I agreed.

"When you feel her now, Richard, there will only be one layer of clothing between you and her bare breast. She will feel it so much more intimately, so make sure to squeeze her nipples gently while you do."

I sat back and watched him follow my direction. "This is awesome," I thought. I reached down in my pants and readjusted my erection so that it was pointed towards my belly. It was starting to be uncomfortable. Glancing up, I made eye contact with Siena, who's expression plainly said that she had caught me adjusting myself. I shrugged and she grinned.

"There is a lot of room in that plunging neckline, Richard. I bet you can get your hand inside and feel your first bare female breast."

Richard started to indigently say, "This is not my first..." and then stopped. He knew, she knew, everyone knew, and we were all cool with it, so he didn't bother. Instead, he slipped his hand into her shirt and tentatively touched it.

"Don't be timid, Richard. That is your territory now. Kiss it, feel it, suck it, but don't be afraid. Forge ahead!"

His touch became more insistent, and the kissing kicked up a notch. Siena was moaning now between ever third breath or so. Her legs were scissoring open and closed too, and I could see just a flash of panties in the low light.

"Take that strap down, Richard, and pop it out. I assure you, it's gorgeous," I urged.

The strap of Siena's dress descended with maddening slowness. It almost seemed that her breast appeared in super slo-mo. Richard and I both swallowed at the same exact time. His hand on her breast molded it, pulling her nipple out towards me. The action was fricken hot and I surreptitiously unsnapped my shorts, giving myself more room.

"Alexa, dim the lights, set to pink," I said. Alexa, being the good bot, adjusted the lighting.

I watched as Richard cupped Siena's bare breast and kissed her neck. Her breathing was definitely increased. "Richard, you know you want to, so why don't you take that breast into your mouth and suck her nipple."

Siena opened her eyes and stared at me as Richard took her breast in his mouth and sucked on her nipple. I maintained eye contact as I said, "Lick from the bottom of her breast up around her nipple and then trap her nipple and draw it out." I could see the arousal in her eyes, and they rolled up in her head as he did what I asked. She again sought me out and glanced meaningfully down at her lower body, opening and closing her legs. I nodded and held up a finger, letting her know we were getting there.

She opened her legs again and left them open. I stared and she stared at me staring and wow, I think I grew like two inches. I had to unzip to give myself even more room, and I could feel me poking out. Judging by how her eyes got wide, she noticed.