Chapter 63: Hers and His First Times

December 18, 2002, San Francisco, California

🎤 Steve

"What do you hope to gain from the four days we have together?" I asked as we had coffee after dinner.

Keiki had shown me her STI test results before we'd come to the restaurant, so that requirement was met, and nothing stood in the way of three full days and nights of passion.

"Nalani suggested you might ask a question like that! I'm not sure I need the same treatment as Nalani because we've had quite a few deep philosophical conversations, something she started doing after she was with you. As she put it, the mindfuck preceded the physical one."

Which confirmed my impression of Nalani's statement that Keiki was prepared.

"Skip to the end?" I asked with a grin.

Keiki laughed, "Nalani and I love that movie! And she told me about your fetish for movie quotes."

"My reputation precedes me!" I replied.

"About everything!" Keiki declared. "Nalani was very detailed."

"I'm not surprised. Based on her descriptions, did you have a preferred way to proceed?"

"I also did some outside reading to prepare for the introductory course!" Keiki smiled. "I want to start with a bubble bath, if that's OK."

"It absolutely is."

"Is there some specific thing you want me to do?"

"Have orgasms!" I replied. "It's incumbent on the guy to ensure his partner has the maximum pleasure possible."

Keiki laughed, "I won't object, but I think you know what I meant."

"I actually prefer long, slow, sensual lovemaking," I replied. "Along with mutual oral sex."

"Mutual, as in at the same time?"

"Yes."

"Not something you and Nalani did."

"No, it wasn't. But that was her choice. You make your own choices."

"May I make what might be a strange observation?" Keiki asked.

"Of course. Say or ask anything; you won't offend me or upset me."

"Oral sex seems way more intimate than intercourse. I know some girls do that to delay having intercourse, but allowing a guy to ejaculate in your mouth just seems SO much more intimate, not to mention the trust required on the part of the guy."

"Rational thought tends to go out the window when lips or tongues touch a man's genitals, so I'm not sure that trust is even a consideration!"

Keiki rolled her eyes and shook her head, "Boys and blowjobs!"

"Have you dated?"

"I've accepted invitations to school dances ever since eighth grade, but no guy got more than a 'good night' kiss because I didn't want a reputation and I wasn't really ready. This year, we go out in groups, and nobody has really paired off."

"That does seem to be more common now than when I was in High School, and everyone tried to pair off. My kids are mixed on that, with two of them having paired off, one intending to pair off, and two playing the field, as it were. And two who haven't made their intentions known as yet."

"That's something else that's a bit strange about being here — I never expected my first time to be with a guy who was married and had kids. And even stranger, his wives know and don't object."

"Nobody in my family accepts social norms as controlling," I said. "That's true about many of my friends and all the members of my Philosophy Club."

"That's something I'd really like to experience, but I think I'd have to come to Chicago. Nalani said she was hoping to participate in one when she's in Chicago."

"We'll have an impromptu rap session, not a formal meeting, given the timing of her visit and other stuff going on. Ready for our bubble bath?"

"Yes!"

I signaled the waiter, signed the receipt to have the bill charged to my room, then took Keiki's hand and led her towards the elevators.

[Aurora, Illinois]
🎤 Matthew

"What did Mrs. Jones say?" I asked Mom when she came back from seeing Maggie's mom.

"She'd noticed Maggie was out of sorts. I was careful about what I said because I didn't want Maggie to have trouble with her parents."

"What?" I asked with a smirk. "Telling extremely religious parents their daughter wants to have sex with a guy who's in a committed relationship with someone else might set them off?"

Mom smiled and nodded, "Pretty much."

"So, what did you say?"

"Just that we'd noticed Maggie was behaving differently and seemed troubled. Mrs. Jones didn't ask why, so I'm not sure if that was because she didn't think I knew or because she had some idea that Maggie was fixated on you, though not why."

"What is Mrs. Jones going to do?" I asked.

"She said she'd talk to Maggie, which is pretty much all we can ask unless you want to violate Maggie's trust and tell them why, at least in broad strokes without the specifics."

"She'd hate me forever," I replied. "Though I'm not sure it's going to turn out any better unless I break up with Chelsea. Even if I was more like Dad, it wouldn't help because Maggie would never go for that kind of thing. She wants me all to herself."

"So does Chelsea!" Mom declared.

"And Chelsea has dibs!" I declared. "I didn't meet Maggie until three years ago; I've known Chelsea for basically my whole life. And I would never even consider changing anything with Chelsea. I'm happy, Chelsea is happy, and we want to be together. Maggie knows that, and she's known that since not long after I met her."

"You don't have to sell me!" Mom replied with a smile. "Once you decided against running away, we all knew where this was headed! Of course, we thought that was true of Jesse and Francesca, too."

"Until her mom went batshit crazy!" I declared.

"Your dad and I have met a few other moms who were like that, too."

"Grandma Adams?"

"Among others. Fortunately, your dad met Melanie's parents, and he learned a lot from them. Jennifer's parents were tolerant but not nearly as open-minded as Frank and Trudy Spencer."

"Chelsea's mom is pretty cool."

"She is. She helped your dad a lot with advice and guidance when he was in Junior High."

"Chelsea said Dad was an altar boy at the funeral for her mom's first husband, who died in Vietnam."

"He was. That was the first time I ever saw him, but I didn't meet him, and I didn't see him again until the wedding. I didn't recognize him, of course, but we figured out later we'd been in the same church that day. I'm sure Melanie and her parents were there, too, though I never asked."

"Small world, as they say," I observed. "I guess at this point, all I can do is try to be Maggie's friend, but I'm not sure that's going to work."

"Neither am I," Mom agreed.

[San Francisco, California]
🎤 Steve

When we reached the room, we went to the bedroom, and I stepped into the bathroom to begin filling the tub. Once the water was at the correct temperature, I closed the drain and added bubble bath from the bottle provided by the hotel. As suds began to build, I stepped back into the bedroom.

"Two firsts to start with," Keiki said with a smile. "The first male to see me naked and the first male I'll see naked! And then a bunch more firsts!"

"Do you want me to undress first, do you want to undress first, or together?"

"One a time, I think," Keiki replied. "I don't want to miss anything!"

I nodded, and without prompting, I removed my blue Oxford button-down shirt, T-shirt, khakis, socks, and finally, my briefs, with Keiki watching intently the entire time.

"You're in excellent shape," she observed. "6th Dan in Shōtōkan, right?"

I nodded, "Yes."

Keiki unbuttoned her pink blouse, shrugged it off, then removed her Chinos and socks, stopping at that point to do a slow pirouette clad only in her white lacy bra and panties. After the three-sixty, she smiled, unhooked her bra, and let it fall away, revealing small breasts with light-brown nipples. I smiled at her, and she quickly removed her panties.

She stood still for a moment as I took in the fullness of her perfectly proportioned frame. She was just over five feet tall, about eight inches shorter than me. I looked up and down, and my eyes were drawn to a neatly trimmed V of pubic hair, pointing to full, plump labia, which already glistened with her juices. Keiki smiled and then did another slow turn, showing me her firm, toned butt before facing me again.

"Would you like to share a kiss before we bathe?" I asked.

"Yes," Keiki breathed.

I held out my arms, and she stepped forward, pressing her naked body lightly against mine and putting her arms around me. She turned her face up for a kiss, I put my arms around her, then bent so I could plant a soft kiss on her lips. Keiki parted her lips, and my tongue sought hers, and we exchanged a soft, sexy French kiss.

"Yeah," she sighed deeply when we broke the kiss a moment later.

I was so tempted to scoop her into my arms and put her on the bed, but instead took her hands and led her into the bathroom. I stepped into the tub, helped her in, then sat down and encouraged her to sit between my legs, which she did. She rested her back against my chest, I put my arms around her, and she sighed deeply once again.

"Amazing," she breathed.

"It gets better!" I said quietly.

"Touch me?" she requested.

I moved my left hand to her left breast and my right hand between her legs, gently tweaking her nipple as I pressed on her clitoral hood.

"Oh!" she gasped. "Wow!"

She seemed to be very sensitive, something borne out over the next few minutes as gentle rubbing with my right hand and strumming with my left thumb caused her to moan continually and groan twice.

"My mouth will feel even better," I whispered.

"I want you to do that," she replied huskily, "but after..."

"Whatever you want," I said. "Shall I continue?"

"Oh, yes!" she whispered urgently.

I lost count of the small orgasms Keiki had in the tub, with me pausing only to turn off the taps when the water and suds covered her chest. When the water began to cool, I opened the drain, then we stood up and got out of the tub. I led Keiki to the shower to rinse the suds from our bodies, then used a large, white, fluffy towel to dry both of us. I scooped her into my arms and carried her to the bed, which I'd already turned down.

"I want you on top the first time," she whispered.

I nodded and laid her on the bed, then climbed in next to her. Because she didn't want me to lick her, I picked up the tube of lubricant I'd put on the night table, and Keiki watched intently as I spread it on my shaft and glans. I returned the tube to the table, then moved between Keiki's legs, positioning my glans against her labia.

"Be gentle..." she requested, her voice barely above a whisper.

She was, in my mind, thinking about the myth of painful first intercourse, a myth that wouldn't die despite it being the exception, not the rule, so long as appropriate foreplay or lubrication was used. I nodded, kissed her softly, and gently pushed my hips forward. Artificial and natural lube allowed me to easily slip past her engorged labia.

"Oomph," Keiki gasped.

I kissed her, then pushed forward slowly, entering her extremely tight tunnel. There wasn't always a direct relation between body size and tightness, but Keiki's tight tunnel matched her small stature and compact size. Two more gentle thrusts had me fully embedded in Keiki, and when I lowered my lips to hers for another kiss, she wrapped her legs around my butt, then pulled me down so my body pressed hers into the mattress.

"Slow and make it last..." Keiki gasped.

I began moving, and after four gentle thrusts, Keiki began moving with me. She had a dozen orgasms over the next twenty minutes as I savored the incredible sensation of her very tight tunnel, eventually allowing the pleasure of the ripples and spasms to take me over the edge, pushing deep as I fired jets of cum deep inside Keiki.

When my orgasm passed, I gently withdrew, moved down, and sucked on each tiny nipple, then kissed my way down to Keiki's pubic hair. I stopped to nuzzle my nose, then pressed my tongue into her, enjoying the tangy taste of her juices. Keiki gasped when I pressed the tip of my tongue against her clit, then groaned deeply when I sucked and licked, causing her to have another orgasm. I gave her one more before moving up to exchange a deep French kiss, from which she did not shy away.

"I'm not sure four days will be enough," she said, breathing hard.

"The only solution I can offer is to find someone like Jun Hie."

"Yes, of course, but I meant I'd want to see you again in the future."

"The only restrictions are if you were in a committed relationship or would want overnight privileges. The former is non-negotiable; the latter would mean asking my wives."

"I thought you were in charge of your sex life."

"I am. There are two rules I need to follow that are, in effect, the price of freedom — girls have to have recent STI tests, and overnights need permission. Other than that, it's up to me. I also have my own rule about anyone who is in a committed relationship, which you know about."

"You liked doing it with me?"

"I did. Very much."

"And you want to do it again?"

"Of course!"

"Now?"

"Yes!"

This time, I began by pleasuring Keiki with my mouth, and after she had a pair of orgasms, I was hard again, so I moved up, entered her, and we resumed our slow-motion lovemaking with the same pattern and results as our first coupling, and as I had the first time, I moved down to pleasure her again with my mouth.

"Would you like what every boy wants?" Keiki asked with a silly smile after I kissed her with her juices on my face, lips, and tongue.

"I won't say 'no'," I replied. "But I very much prefer what we just did!"

Keiki kissed me, then gently nudged me, so I moved off her and lay on my back. She turned, straddled my face, lowered herself until her labia touched my lips, then grasped me and took me into her mouth. She knew exactly what to do and gave me a slow, sexy blowjob while I pleasured her with my mouth. She had three orgasms before I tensed, groaned, and pulsed in her mouth. Keiki swallowed my cum, then released me, turned, and we exchanged a deep French kiss.

"What did you think?" she asked.

"I believe you already received my positive response!" I chuckled.

Keiki laughed softly, "I suppose so! How many times before you need to sleep?"

"Three or four more," I replied.

"Then twice with me on top, once more with our mouths, and then a final one with you on top before we fall asleep."

"Your wish is my command!"

December 19, 2002, San Francisco, California

🎤 Steve

When Keiki and I woke up, we made love, showered together, then had breakfast delivered by room service.

"Besides the obvious," I said as we began eating, "what do you want to do today?"

"I've never been here before, but I know you have. Could you show me the city?"

"Yes. And we could do some shopping."

"Nalani suggested Victoria's Secret!"

"We can do that. What's your favorite color?"

"Red, but I think something sheer and white would be better, though I know lavender is your favorite color!"

"Nalani did give you all the details!"

"She did!"

We finished our breakfast, then put on our jackets. I grabbed my fedora, and we headed out to see San Francisco, starting with a cable car ride down California Street. We visited Fisherman's Wharf and Coit Tower, had lunch, then went to Ghirardelli Chocolate Company. After I bought chocolate for everyone back home, we headed to Victoria's Secret. I almost laughed when I saw the same sales clerk — Cheryl — who Nalani and I had seen in June. It was obvious she recognized me, but she didn't say anything until Keiki took several items into a dressing room to try them on.

"You have a thing for Oriental girls, I see," Cheryl said quietly. "I suppose California Blondes are boring? Or is twenty-three too old for you?"

"Yes, I do like Oriental girls, but the truth is I don't come to San Francisco very often, and I expressly came to meet Keiki."

"How do you meet these girls?"

"I met Nalani, who was with me in June, in Hawai´i, and Keiki is her friend."

"Word of mouth? You must be really good!"

"I've had no complaints," I replied.

"I'm still interested in a 'sugar daddy'!"

"As I said last time, not what this is. I'm simply mentoring them."

"Complete with an Amex Platinum card!"

"I'm a successful entrepreneur," I replied. "And I make friends easily."

"So it seems!"

"Steve?" I heard Keiki call out. "Come see."

I excused myself and went to the dressing room, went inside, and closed the door behind me.

"Wow!" I exclaimed.

"I thought you'd like it!"

She was wearing a white lace teddy and white chiffon peignoir that accented her body perfectly.

"I actually prefer clothing which leaves something to the imagination. Not that I mind seeing you naked! If you want those, I'll let the clerk know."

"These and a lavender bra and panty set?"

"I'll have her ring them up," I said.

I left the dressing room and walked over to Cheryl.

"The teddy and peignoir, plus a lavender bra and panty set," I said, handing over my Amex Platinum card.

"If you come back, I'll arrange for a private fashion show!" Cheryl offered.

"I'll keep that in mind," I replied.

Keiki came out of the dressing room just as Cheryl finished ringing up our purchase. She ran my card, I signed the carbonless flimsy, she handed me the bag, and Keiki and I left the store.

"She was flirting with you, right?"

"Yes."

"The same one who flirted with you when you brought Nalani to the store?"