Chapter 9: A Night to Remember

As usual I was dressed and ready for dinner well before my client, so I had plenty of time to hang out with Nancy, Chad, and Claudia in the kitchen. We'd shared a very memorable week and the conversation started off bittersweet, but Chad soon had me keeling over with laughter. The laughter was contagious and soon we were all joking about the highs and lows of the last week. Once everything was ready, I invited everyone into the living room for a drink before the meal.

Emily made her entrance as we walk through the foyer. It was Nancy who noticed, made a small cough, and pointed up the stairs to Emily.

"Wow!" I gasped. After this afternoon's thong bikini, I was expecting something scandalous and skimpy. Instead, Emily wore a light blue silk sheath that was perfectly tailored. It accentuated all of her still developing curves yet revealed almost nothing. 'Except for a distinct lack of panty lines, ' I observed as she walked down the stairs and into my open arms.

"Nice suit," Emily remarked, going up on tiptoes to kiss me. She gave up after noticing I wasn't meeting her halfway, as even in heels she wasn't tall enough. With a sigh, she grabbed my head and pulled me down to her level and kissed me quite soundly.

Several moments and a few cat calls later, I pulled back and we continued on into the living room where a bottle of champagne chilling in a bucket of ice was waiting for us. After pouring us all a glass, I was about to make a speech when Chad beat me to it.

"This week started off a bit rough," he began while tipping his glass at Emily, who had the decency to blush.

"You've done an amazing job and made remarkable improvements," he continued while indicating me and Emily in turn. "We hope you've had an awesome visit, and we would be pleased to host you again the next time you're in Cayman."

Holding his glass of champagne aloft, Chad toasted, "To time well spent!"

It seemed a very appropriate toast, and I cheerfully clinked glasses. Emily seemed to agree and had yet to stop smiling or drift more than a few millimeters from my side.

Next it was Nancy's turn. "I'm proud of both of you," she said, with a smile, then leered at Emily and added, "and it was a pleasure servicing you."

After the laughter died down, she toasted, "To firsts!"

Claudia then stepped forward. "Now, I've never been one for toasts, so all I want to say is be patient and I hope you have a very good night." This last was said with a wink and there were smiles all around when we again clinked glasses.

I was about to step forward when, with a small cough and a deep blush, Emily made her speech.

"I know I haven't said it nearly enough, but this week has truly been an amazing experience. Thank you."

Short, sweet, and completely unexpected, I could tell that everyone was touched by her words. Not wanting to ruin the moment, I too kept things short and made sure to make eye contact with everyone, including Emily.

"Working with you has been a lot of fun, and I hope that one day we will meet again."

Once we'd all said our toasts, I could tell people were getting rather emotional. It was Emily who pulled away from me and ran across the room to give hugs to our hosts.

"I'm going to miss you guys," she said.

Even Chad got a hug and, by the end, there wasn't a dry eye in the room.

Once things settled down, Nancy moved near the doors to the formal dining room.

"It's a tradition on the last night of a Docent visit, if everything went well, that utensils are not allowed in the formal dining room."

Claudia immediately chimed in waving a finger, "But if you bring anything upstairs, so help me, you'll be cleaning up the mess."

At Claudia's exaggeratedly severe expression, I couldn't hold back the laughter, and it was several moments before I'd recovered enough to enter the room. We were once again smiling as Nancy began explaining all the dishes we had to choose from.

"This is amazing," I said, gazing at the impressive array of finger foods.

When the rest of the staff seemed ready to leave, I reminded them that Emily's father was providing dinner and drinks at the restaurant of their choice, and they had the rest of the night off.

"As if we'd want to interrupt?" Nancy teased as they left the room.

Dinner was a lot of fun as Emily and I spent the entire meal feeding each other. Heeding Claudia's warning, we confined ourselves to playing with the dessert in the dining room. After a few failed attempts at getting the fruit and whipped cream into my mouth, I was beginning to suspect foul play, but really didn't mind. Plus, I made sure to give as good as I got. By the time we'd finished our meal, Emily and I were both laughing as our attempts at feeding each other got progressively messier.

"Alright, enough!" I cried in exasperation when she started getting whipped cream in my hair.

"It really is good that we didn't take these upstairs," Emily admitted once we settled down.

"No kidding! Just before you came down I saw Claudia loading-up the tray over there with steaming washcloths. I bet they're still warm."

"Sweet." Emily jumped out of her chair and heading over to the tray. Fetching four towels, she gave me two and proceeded to wash my face.

"I think I can manage on my own."

"I know, but this way is more fun," she replied, quickly finishing up then perching at the edge of her chair waiting for me.

"Whatever," I replied in my best imitation of Emily's voice and attitude from our first encounter.

"Are you ever going to let me live that down?"

"Probably not," I teased back with a smile.

"Oh, I hate you," she replied with mock severity as I finished washing her face. Before I could set the towel down, Emily jumped out of her chair and headed for the door.

"Well, aren't you coming?" she demanded when I didn't follow fast enough.

"Not yet!" I called out, but she didn't stop. I had to run after her as she raced up the stairs to my room.

Emily's confidence seemed to melt as she came to a sudden stop a few paces from my door.

"Now what?" she asked timidly, turning towards me and finally sounding like the maiden she was.

'Now you let me do my job, ' I nearly replied. Instead I stepped close and let my lips speak for me.

Emily pulled away slightly and asked, "Will it hurt?"

I wanted to lie, but knew she'd demand the truth.

"We're not a great fit, but I'll be as gentle as possible."

Her eyes met mine. "Promise you won't stop?" she demanded.

"What?"

"My biggest fear isn't that it will hurt, but that it will hurt, and you won't go through with it."

At my skeptical expression she added, "Sex is supposed to hurt the first time, but then it gets better. I want to experience every part of sex: the pain and the pleasure."

"It doesn't have to hurt," I hedged, knowing Kael had included some of the Institute's numbing cream just in case. Even though the Institute had carefully weakened her hymen during her vaginal exam, it was strongly recommended that we use the cream. If I was careful to keep the cream away from her clit, it wouldn't reduce her sensation all that much and would ensure sex was much more comfortable. The cream would have almost no effect on me or my sensation.

The client survey includes several questions along the lines of 'If given the option, would you want tearing your hymen to be completely pain free?' Obviously the questions are much more discreet, but it still amazes me that a vast majority of clients viewed the initial pain as some sort of 'Right of Passage, ' and on both questionnaires Emily was firmly in this category.

"Then what's the point of still having a cherry?" Emily protested.

I'd had clients like Emily before, and knew it would be rather pointless to argue.

"It's your body and I respect your decision, but I refuse to take part if it's more pain than pleasure."

"Promise you won't stop!" she insisted.

I could tell this was something she truly wanted, but I couldn't promise not to stop.

"I promise to try it your way for three minutes. After that point, if it's still painful, I'll either apply the numbing cream or we'll stop."

Emily sensed she wasn't likely to get more of a promise out of me. She nodded her acceptance, grasped hold of my hand, and followed me into the room.

There were so many different ways to start off. I hesitated as I contemplated what to do next.

Generally speaking, most Docents tend to follow two guidelines when they're with a client for the first time, regardless of whether they are a virgin. First, confidence is contagious, so don't hesitate. Make it seem like every act is intentional. Second, know your client well enough so that you do not have to ask which position she wants to try first or how she wants to start off.

I had no issues with the first rule, but was completely tripped up by the second. Even after nearly a week together, I still wasn't sure how Emily would like to proceed. In the end I pulled her close, shut my eyes, and decided to wing it.

Things started off fine. My jacket and vest came off, and suddenly buttons were too much of an inconvenience to deal with. Even in my frenzy, I respected Emily's dress, and I could always pop a bra open faster than rip it off. But her thong wasn't nearly so lucky ... two flips of the wrist and a satisfying rip later the sheer material was floating to the floor.

"So Nancy wasn't lying," Emily squealed as I pulled away the remnants of her thong.

Emily tried the same trick on my boxers, managing to break a nail for her effort. She stepped back, jutted out one hip, and stomped her foot.

"It would have been more considerate to wear clothing I could rip away, too."

I was about to offer some flippant reply when it finally sunk in that Emily was completely naked in front of me. I'd been so focused on getting her undressed that it hadn't registered until that moment.

Standing before me was a pristine example of a girl just blooming into womanhood. Emily was petite in every way, but her perky breasts fit her frame perfectly, and the upward pointing puffy nipples just begged to be sucked. I noticed she had only a sparse patch of blonde pubic hair, but the way she'd angled her hips obscured most of the view. I allowed myself to absorb the full vision Emily presented: hand on her hip, nostrils flaring, eyes hooded, pupils dilated with desire ... every aspect of her being radiated sexuality. I knew better than to deny her.

In an instant I too was naked, and this time it was Emily's turn to gasp. At first, she made a valiant effort to look at all of me, but we'd gone swimming often enough that she'd seen most of my body before. Her eyes were soon riveted to my semi-hard cock. Sensing an opportunity to lighten the mood, I flexed my cock to make it twitch slightly, and elicited a gasp of appreciation for my efforts.

"Will it fit?" Emily asked once she'd recovered enough to speak.

I could tell that her determination to not use any of the numbing cream was weakening, but knew she'd never forgive me if I tried to take advantage of the situation.

"Like I said, we're not a perfect match, but if we go slow enough, you'll stretch."

I hesitated for a moment and added, "Although I'm not sure how comfortable it will be, as each girl is sensitive in different ways. Some enjoy the feeling of being stretched and filled to capacity ... others don't."

"Hmm ... I think I want to give it a try," she replied before biting her lip.

"That's good because I think I do too," I leered while enfolding her in my arms and tackling us onto the bed.

"Hey, gentle," Emily complained, slapping my arm.

"Since when do you like things gentle?"

"Well," she hedged. When I raised an eyebrow she grudgingly added, "Alright, so yeah, that was fun. But next time could you land next to me?"

"I suppose," I replied with a laugh.

"Good, then get off!" she growled as she playfully shoved me away.

The mood was lightened and I allowed my hands to explore. I instantly noticed that Emily was exceptionally sensitive. I gently brushed her arm and she shuddered, stroked her stomach and she purred, caressed her breast and she moaned.

I reached down to cup her sex when Emily's hand shot down to prevented me from exploring further.

When I looked into her eyes, she grew serious.

"If you touch me there, I'm going to cum, and I want you inside of me first."

Nodding, I reached across her to the nightstand and grabbed a tube of KY just to be on the safe side. I was about to get into position when Emily saw the lube and went completely crazy.

"What are you doing?" Her eyes blazed as she cried out, "I said I didn't want any!"

I understood how she could misinterpret my actions, but was annoyed by lack of trust.

"Look, if you can't trust me then we might as well stop."

My irritation must have shown more than I'd intended, but I just couldn't understand why her first reaction was to assume I'd break my promise. Turning the tube, I held it so that she could clearly see the KY label.

"The seal is still on if you'd like to check that hasn't been tampered with."

"Oh! No, I'm sorry. It's just..." words failing her, Emily's lower lip started to quiver and she softly whispered, "Please, don't stop?"

I'm not sure if I'd made my point, but now was not the time to discuss it. I nodded my assent, applied a liberal amount to both of us, lifted her knees slightly and aligned the head of my cock with her opening.

I leaned forward so that I rested most of my weight on my elbows and began to lightly nibble around her ear.

"Hey, that tickles!" she complained, but made no effort to move away.

"Have I told you that you're incredibly hot?" I whispered in an effort to distract her.

"Really?" she asked, sounding genuinely pleased with my compliment.

"Truly." I bit her earlobe and thrust hard with my cock.

I'd managed to line myself up near perfectly, as there was just a slight bit of resistance at first, and then I felt her hymen give way and the first few of inches of my cock slid home into the vice that was her pussy.

She gave a sharp intake a breath, followed by a slight pause while I gently sucked on her earlobe and lightly caressed her ass. I leaned back just as a small, 'Ow, ' escaped Emily's lips and a single tear ran down her cheek.

"You feel amazing," I soothed. I was impressed that either I had fit more easily than anticipated, or she had an incredible pain threshold.

I leaned forward and softly kissed her on the lips. As I pulled away Emily trapped my lower lip between her teeth and bit down hard.

"That hurt!" she exclaimed after releasing my lip as she reached up to rub her ear.

"I'm glad it helped. Think you're ready for a bit more of me?"

Emily's eyes grew wide as she realized that I'd done more than just bite her ear.

"Is it all the way in?"

"Almost halfway," I replied. I held her steady and hoped she would be able to relax and loosen up before we tried to get more in.

Emily closed her eyes and seemed to focus herself for a moment, then somehow managed to clench even tighter around my cock before willing herself to relax.

She gasped in pain when I pulled out slightly. I wasn't sure how this would work. Normally, I'd gradually build up to deeper strokes, but with Emily that seemed like the more painful method.

"Are you sure this is what you want?" I asked again just to be sure.

"Yes," she insisted, though her eyes seemed uncertain.

Deciding to change positions, I hooked an arm beneath each knee and reached under her to firmly grasp her shoulders.

A low groan escaped Emily's lips as I slowly buried my cock in her. It was a very tight fit, but surprisingly she'd managed to stay relaxed. Aside from the occasional groan, Emily seemed to be doing well.

Eventually our hips met and I gently nuzzled her neck to get her attention.

"It's all in."

"I feel so ... full!" she exclaimed as she wrapped her arms around me.

"Good full?" I asked, leaning back so I could meet her eyes. Her eyes were half lidded and there was a smile on her face.

"Very good; this full feeling is awesome!"

'To each their own, ' I thought ruefully, glad it hadn't been too painful.

As I slowly began to thrust, Emily's jaw dropped and her eyes closed completely.

"Are you okay?" I asked, worried I was hurting her.

"This is amazing!" she cried. Her hands dropped lower until they firmly grasped my ass, as if encouraging me to go even deeper.

"Faster," she purred as she began to guide my thrusts.

Rarely one to deny a client's wishes, I was more than happy to comply. 'This is our last night together, so why not give her what she wants? Besides, with the size differential, she'll be sore in the morning either way.'

While Emily appeared to have a hair trigger earlier, now she seemed insatiable and constantly demanded things harder, deeper, and/or faster. It got to the point where things were damn near animalistic when I decided she'd had enough for one night.

Reaching down I began to alternately caress and milk her clit. "Yes, right there ... make me cum!" she begged.

Eager to please, I synchronized my caresses. Soon Emily was thrusting up to meet me. Moments later her back arched and her pussy clamped down hard.

It was amazing to watch. It was as if the orgasm shot through her and she started thrashing wildly. Relaxing my own controls, I had just started to cum when her eyes rolled back and she went completely limp.

'Man, just once I want to be the one who passes out, ' I thought ruefully as I rested on top and gently caressed Emily's face. It had been a powerful orgasm and she didn't stir when I got up to fetch a washcloth.

It was only when I was cleaning us up and accidentally brushed her clit that Emily's eyes opened. "You are absolutely amazing!" she purred.

As we cuddled together afterwards, I couldn't help thinking about the contrast between Emily and my other clients. Some clients wanted, and needed, to learn absolutely everything about sex, and gained confidence by knowing that they were both desirable and "talented." Others were more interested in learning how to court the right type of guy and defining their limits on both how far and how fast they are willing to go.

"I'm impressed you were able to wait."

"I can't believe you turned me down," she replied with some of her old attitude.

Caught off guard and slightly concerned, I shifted so I could watch her.

"Can't you?"

Emily seemed about to respond, then hesitated as numerous emotions flashed across her face and she pointedly refused to meet my eyes.

"You really do care."

"Was there ever any question?"

"Well, we didn't exactly start off on the best of terms. I never thought you would be the first person to actually be completely honest with me," she replied with a shrug.

"It is not possible to become an Elite without caring about your clients. Developing trust is important to me. It is difficult to fake a bond, and most clients would notice almost instantly if I didn't care.

"Just because we didn't start off well doesn't mean I'd try to get revenge later on. I mean, what's the point? We've come a long way in the last few days. I'm not about to throw that all away just because you hurt my feelings before you even knew anything about me."

Emily considered my words for a few moments. Her face darkened as she suddenly found a target to blame.

"Why do you have to be so perfect!"

"No one is perfect, and people don't change overnight," I corrected her gently. "You've made great progress this week towards becoming the person you'd like to be."

"But I have to head home tomorrow! I made such a mess of things before I left that I'm not sure how I'll manage," Emily replied softly with a shudder. Tears streaming down her cheeks, she finally met my eyes. In a timid voice said, "I'm so sorry."

I nodded solemnly in acceptance, knowing she wanted someone to listen.

"Our entire week was supposed to be like this. Wasn't it?"

"Perhaps. Each person is unique, and it really depends on what the client needs. Tell me, even though we didn't have sex until tonight, did you learn anything this week?"

Emily seemed to be at a complete loss for words, but her eyes seemed to cry out, 'I learned more than you'll ever know, ' and that was good enough for me.

Leaning over, I softly kissed her on the lips. I could tell she was once again fighting back tears. I gathered her in my arms and, with her head resting on my shoulder, just let her cry.

In many ways the week had started off a near total disaster. Yet it was certainly a week I wouldn't soon forget, and I couldn't think of a thing I would have done differently. I was confident that I'd gotten through to Emily.

I jerked upright with a start, my body shaking as the lingering effects of my nightmare slowly subsided. Perhaps it was her similarity in size to Emily, but I'd been dreaming of my night with Tess many months before, only this time when I came in the dream I didn't hesitate in crying out 'Beth!' In fact, every part of my being cried out that I'd said the correct name, yet Stephanie had still stormed into the room completely livid, berating me that I had just thrown away my career, and Sarah was angrily pounding on the door demanding to know why I hadn't called.

Taking a couple of calming breaths, I forced myself to lie back down. Emily and I had gotten carried away and stayed up quite late, so my thrashing around hadn't woken her. Thinking of Emily and the way we'd managed to turn the week around really helped me calm down.

As if sensing my need, Emily snuggled closer and draped an arm protectively around me. She could have been asleep, or I may have woken her, but honestly I didn't care. Snuggling deeper into her embrace, I was soon fast asleep.

I awoke a couple hours later to the feeling of someone skillfully stroking me to erection.

Sensing I was awake, Emily leaned close and whispered, "This is something I've wanted to try since watching the Boys DVD," and nipped my ear lobe.

"Ow!" I cried, now closer to being fully awake. I glanced at the clock and groaned, "Emily, it's five in the morning!"

"Payback's a bitch, isn't it? Besides, I have a 10 o'clock flight, I still haven't packed, and I want to have some fun."

Her logic was sound, but after my nightmare I hadn't slept well and was really tired. All of that changed when Emily whispered, "Maybe this will help!" Still stroking my cock, she wiggled under the sheets, and moments later I felt her warm mouth encase the head of my cock as she used her tongue to stroke the sensitive underside.

I instantly grew hard as Emily simultaneously stroked my cock, sucked on the head, and squeezed my balls. 'You're in ¬deep trouble now, ' I thought. I moaned as I felt Emily swallowing almost my entire cock. She seemed to be testing out all of Nancy's suggestions, along with those on the Boy's DVD.

"You're a natural!" I sighed with a contented sigh, before yelping as she squeezed my balls a bit too hard. "Hey! Lightly squeeze," I admonished.

When Emily hesitated, I added, "No, I didn't mean stop."

"Good!" came her petulant response from below the covers. "But some positive feedback would be nice."