Not Quite a White Night Vol. 04.8

Teaming Up On The Ladies: Overnight Delights

Note the title format, this follows Vol. 4.7 of "Not Quite A White Knight," subtitled "Teaming Up On The Ladies: Auction + Orgy."

Chapters include:

Chapter 68. In The Room - Word games, coming clean, then getting dirty with Sondra in the shower.

Chapter 69. Lisa's Turn - Lisa wants pleasure but does not need the mess.

Chapter 70. Rose Time - The boss's daughter wants the mess.

Chapter 71. A Late Night Stroll With Extras - A late night walk with some naughty drama for any audience.

Chapter 72. Alone With Sondra - Alone with Sondra on the slippery slope to where the bad girls play.

Chapter 73. Breakfast Then Company - A surprise visit from the boss's sweet saucy daughter.

Chapter 74. Sunday Lunch - The girls share "who" and "what" details.

Chapter 75. Report From The Yucatan - No sex. Brief reports of bad things happening to bad people in a bad place because of their bad choices.

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Chapter 68. In The Room

Saturday August 30, 2008 at 10:30 PM

The Team Hotel Room

Sondra put on a brave face and said, in a low, sexy voice, "I think we're alone now." This was about 20 minutes after we arrived at the team's bedrooms from the party room. We were in the shower.

-

When we got to the team's hotel room and the hallway door was closed I slipped the hardware off Sondra's wrists. As soon as she was free she kissed me, long and hard, saying that the little bondage show during the walk back, with exhibition and a little theatrical abuse with others gawking and pointing while they whispered, was the cherry on the sundae. She could not thank me enough, but with that kiss she wanted to try.

"Playing rough with my tits while I was up against the wall was perfect, it was so much more than I envisioned," she said. "Thank you for enjoying me."

When we four got to the room after our little parade with blindfolded and handcuffed Sondra, the other four had already showered and were ready to play. But Rose, Sondra, Phil and I still had some whipping cream on our bodies. With 4 people and 2 showers we decided to share them as couples. Sondra gabbed me leaving Phil to have good clean fun with Rose. She did not seem to mind, I sensed they were a little more familiar then I expected. He had just made partner so he never had a social overnight with her, and since he was married less than a week it didn't seem like there had been time for a date, but clearly they were not strangers.

Then I was distracted.

In the shower Sondra and I put our hands all over each other, more or less under the guise of washing. Sondra took the lead, she was not shy about working from my neck down my body with her soapy hands, including my cock and balls like it was a pleasant routine. She was a good actress. Still I could tell she was unfamiliar with the area in general and she was very gentle. I gave her some guidance.

After she did my feet she said it was my turn, but she asked that I treat her "with a little less delicacy" than usual.

"Look, I know you would not hurt me intentionally, it's not your nature. But I want to 'feel' more, so could you? Please?"

So I treated her to the same routine, neck to toes, but with a little more vigor. I started by standing behind her, with her leaning forward supporting herself with her hands. That made her feel helpless. Then, when I did her neck, I took her ear in my teeth to hold her in position, then applied a bit of extra force with my hands, it was a very efficient way to get a reading on what she was comfortable with, and what was a little bit more. When I handled her breasts it was more a mauling and less a caress. Plus the nipples got more of the 'pull and twist' treatment. Working down, when my fingers entered her - two at once - it was abrupt. I did not hurt her, but there was no real gentleness.

She pressed herself against my hands at every opportunity, encouraging me. "I am thirty and I have never known the touch of a hand that was firm, backed by real muscle. My life has been sheltered, and now I fear I have passed some experiences by."

When I got to her feet I mentioned that "toe sucking was not on the preference form, but if she was interested..." She was intrigued, but said to be fair, I should ask her again later, after she had been in a few beds with others.

I noticed that there was crevice she had not washed on me, and out of respect I also left that part of her alone. Otherwise I even delighted in washing her toes, being careful to avoid anything that resembled tickling.

When I finished her toes and stood up her attitude changed, she was going someplace else, someplace more serious and was building courage. She put on a brave face and said, in a low, sexy voice, "I think we're alone now."

It is the way my mind works, the five-word phrase was a specific trigger to me, the line from a song, so I went to someplace she did not expect. "That was great song, some called it the first elevated bubblegum music, even though the tone was calibrated to be just the other side of suggestive. Tommy James and the Sholdells, plus their writers and such, were ahead of their time. Did you know that, when the song came out, some radio stations would not play it because of the suggestive tone and treatment of the lyrics? But during the Reagan years it was a dance rebellion. Tiffany was performing in shopping malls in Utah, singing while wiggling for screaming tweens, teenagers, and their mothers, all dancing like innocent 60's teenagers who were oblivious or didn't care about the suggestion. I kind of like her version too."

Surprisingly, it was not what she intended, but Sondra was with me on my detour, she got what I was saying and knew her music history. "I agree, he was ahead of his time. Covers of that song and 'Mony Mony' were both big hits the same month in the eighties... But that is not what I was asking about. It was a preface to a question I wanted to ask you privately... what we talked about."

I could see this was difficult for her, she wanted help crossing another line. Well, based on the cum in her pussy, I was her boyfriend for the last two hours, so I tried to be supportive and nonjudgemental. "Okay, ask. What can I do?"

"Can I trust you?"

"You must know that is a rather broad question. We really do not know each other that well for the general universal question..." She seemed a little upset that I did not give a simple answer. "For instance, we could not testify in court as a character witness."

That was a context Judge Stern's daughter could understand, it calmed her down. "But for an intimate matter..." I gave her a chaste kiss that stretched a bit, then said, "you can trust me about such things."

We broke apart, now she was more confident about me and was a bit bolder. "Well, the question I want to ask is rather specific and private... it is well outside the bounds..." She looked at the floor when she spoke, it explained a great deal. "About the thing you did before..."

Ah! She was curious about play with her cute tight little ass. "The finger in back?" I said. "You really have a very attractive bottom." The woman was almost as tall as me, and while she exercised and fought to keep her weight down, she did not have the cute little bottom Rose sported.

"Yes, that. Thank you for the compliment. Can I trust you to stop if we start... start a little play there?"

"Yes, you can trust that I will confine myself to your expressed limits. Most guys are totally unreliable regarding the subject, they are driven my the monkey brain and given a chance will act out of character, especially if they have a chance to put something else in a tight... Well, it is male nature to feel good plus they are curious. Most female won't allow... But there are reasons I am trustworthy. My mother raised me with a special emphasis about things, so I do not have the usual foolish desires to 'just do it' that drives many males."

My answer made her more confident, bolder. "That is good to know. With that in mind, could you do it again? Touch me there... and maybe push in a little so I know what it feels like?"

"You have seen 'Last Tango..." It was a statement, not a question.

She was relieved by the common reference. "Yes, exactly! You understand, I don't want the 'get the butter' scene. But I would kind of like to reverse the 'pig' scene where Brando tells Marie to... do that..." she couldn't say the specific words, "to him."

As I applied a little soap to my finger I talked about it. "As a rule, I do not do that... that is I don't accept a finger like Brando did. Again, it reflects how I was raised. But I don't mind reversing the roles... for education or pleasure. Turn around and press the front of you body on the shower wall like Brando did in the movie."

She did as I asked, we both knew the scene from the bathroom. She turned to the side wall and presented her ass slightly. "Good. Relax. My fingernails are already short." She clasped the pipes, bracing against them. I felt a shiver go through her as I gently touched her puckered opening. I kept it light, exploring, touching without pressing. Just making her familiar with her own nerves and getting on target. I slid my finger up and down along the crack a few times, then back to her pucker. Then I let my finger slowly trace the circular muscle. "Some people enjoy a tongue, giving pleasure, or getting pleasure... admittedly there is a strong symbolic component there. That requires a bit more knowledge, prep, understanding and trust by both parties. Let us say that is off the table... for today."

"You do that?" She sounded shocked at the thought. But underneath the words her tone said that she would come back to that as a desire. She was curious, and I had basically told her that I might relieve that curiosity.

"Off the table means off the table. Focus on what you feel now."

She relaxed a bit, the conversation helped. "That does not sound like something I would be interested in." She was lying, I am trained as a human lie detector and everything - how quickly she responded, the tone of the words, the way her volume varied modulated - it all said she was very interested. But we were a long way for that.

"There is a saying, 'don't knock it until you have tried it.' But moving on, do you think you still want this new experience?" I pressed with my finger a little against the entrance. She stiffened so I stopped. But she fought the reaction.

"Yes," she said, with bravado standing in for conviction. She was trying to convince herself, but her voice held a bit of anticipation that was not there before. She was not really ready, but did not want to back away either.

"Okay, as I push in you will have less discomfort if you also push out. But I don't expect you to do that, it is not easy for a woman to do with somebody unless they are both very intimate. Our public fuck does NOT count as intimate. Maybe someday. For now, what you might do is relax yourself. Think of the muscles in your body and give you tight little gatekeeper permission to relax a little, to take a break. When I feel that I will begin to push in. Don't worry about what is inside, the water is running and we both know how things work."

"I will try," she said. Like when I first took her, her body was broadcasting both trepidation and desire. There was a sharp intake of breath from her, she thought I would jump at the first sign. But I held back to give her time to prepare herself. She sought to master her own body. She did yoga so she had some idea. I knew that a seed of impatience was also growing in her mind.

She started to relax a few times, only to tighten up again in anticipation. I stayed where I was, my finger at her entrance but not moving, letting her get used to me. I wanted her to trust me, and I knew that waiting was a quick and easy way to earn her trust.

I leaned forward and whispered in her ear. "I won't rush you, I'll wait until you are ready." I felt her body relax as I spoke.

"Thank you," she said. "It is hard to prepare... to stay relaxed. I want to, but I am scared."

I washed off my other hand, then put my little finger where she could take it in her mouth. "Try this, get a sense of perspective."

She did. "This is rather small... I should be able to... could we try that?"

I switched to my little finger, then waited for her to relax her muscle and her body. She did.

Then I waited just a bit longer, until she whispered, "Please."

Using a wrist twist I slipped the tip of my little finger just barely into her ass.

She fought off the urge to tighten up completely.

"Oh!" The small sound she made said she expected pain but was surprised by it's absence. I let her get used to it, then when she wanted more I pressed in deeper. That was not what she wanted. "No. Put... use a different finger. Something bigger... I want to feel more."

So I did, I slipped my forefinger in and got it half way to the second knuckle before she tightened. She took it, exploring her senses. After a few moments she asked for more. "Go deeper... as far as you can... OH!... yes... finger-fuck me... fuck my ass like a cheap whore you bought."

Well, that gave me something she needed for a distraction.

As I started to move my finger deeper I talked to her. "You should know that I never buy whores, not the cheap ones and not the expensive ones either. I only stick my finger up the butts of very expensive dates - and it is usually after they have enjoyed a fabulous evening out and want a spicy ending. Of course, as a married man I no longer do that, no matter how much they beg." She snorted a laugh at that, it really went a bit too far. "Perhaps... but we can talk about such things later."

She gave a giggle, she liked my diversions as she was getting used to my molesting her butt. She was hugging the wall as I pressed a bit more against her back, giving her a full reading on me and my erection. I had been soft when she washed me, but now I was very hard and erect. Of course, her mind went there, to my cock in her ass. She was experiencing the closeness and sensations of something she never expected to know. She had submerged her shame and lifelong conditioning about the act, allowing her to focus on my finger and how it felt inside her. Plus how other things might feel.

In doing that she opened more than her ass to me, she opened her self, giving trust and intimacy to me. The next time we met at a social, where she was dressed in something fabulous and expensive to conceal her body, she would recall this moment, drop her defenses, and feel closer to me.

I leaned toward her ear again, whispering was good, plus the breath on her ear made it personal and intimate. "Think about where I am. You have a great ass, guys naturally think of fucking it... even gay guys, I am sure."

She giggled at that, but she knew the truth of it, in jeans and a baggy hoodie she had be mistaken for a male more than once. She was tall enough and her face would work either way if it was in shadow and the hair was not a signal.

I continued, "As you can see, this feeling is not really sexual, not for a woman. But it is very intimate... more than naked. I bet, even here in Cali, most wives have never done this, they would certainly never let the man they love do this. But you want it, and you are going to want to be naughty again, don't you?"

"Yes... with you. You make it easy for me. Maybe trust... why do I trust you to do this?"

I didn't need to go into family history, so I kept it simple and honest. "Actually, I am descended from a long line of trusted people. It is a fact. Call it the family business. Plus, there is my mother's special training. It all factors in."

"Your mother taught you this?"

"No! But my mother taught me to respect and pleasure women. To listen to what they want, even when they can't say it directly. Plus how to be trusted."

She gave a little chuckle. "Okay, I can see that. You mentioned tongues..."

"Maybe sometime tongues can be involved. That can be reciprocal, and not usually the first or second night. Talk to Rose about what is needed."

She gasped. "Have you...?"

"No, we have never... not at all. You may have noticed I even skipped her orgy session. But I am... aware that she knows the drill, and you can ask her without turning red. DO NOT ask you mother. Or Abril."

"Yeah... roger that."

"I don't know this 'Roger' guy, is he a lawyer? If so, don't trust him." She giggled at the humor. I moved my finger a bit inside her, probing against her pussy wall during the giggle. Her sharp gasp told my when I found the good spot in her pussy. "Now that feels sexual, doesn't it? We have discovered something that, to my knowledge, is not common."

The mental image and the physical sensation were getting to her. "Yes... it is strange but... when you do me like this... that spot... I feel like a slut... but in the good way I discovered earlier. I want to do things... sexual things... like a weekend in bed... doing things I can't bring myself to talk about out loud."

"Well, along those lines... try this... Imagine two cocks, one in front and one in back, doing... using your body... one in this hole, moving in alternation, so they both hit the spot. You can make two guys happy."

"Oh my... that image... I am close... Do you... do you do that?"

"I have had occasion, I was a teenage once. I have relatives and we shared... we lived on a farm... But these days I prefer help with a toy like Rose used on you. I imagine is better with a woman attached, but the other works too." She gasped as she imagined such a thing, I wondered if she was thinking Abril or Rose? "At home, I have some real nice toys that give movement."

"Oh goodness... such words... things to think about. Wait... you said relatives?"

"Sondra Chaste-Sumner, I am sure that you would be a party for my cousins. Do you want to touch yourself?" I focused my movement on that spot inside.

"Oh!... yes please," she said. She rushed her hand to her clit. The idea had not occurred to her, it was too embarrassing until I said it. Then it was irresistible.

In about 15 second she was jamming her other fist against her mouth, trying to keep quiet as the quick climax washed over her. she knew a lot about self-pleasure, after she was 18 she spent a decade never once knowing any other hand, when the urge came she had to do it herself. I kept fucking her ass with my finger, working with her. At the right moment I nipped at her ear, a little pinch of pain freed her, sending her to new heights. Her body shuddered against me as I pressed her to the wall, my male body pressed against her, a shadow of 'what was possible' on her focus. The peak went on for a time, she was shuddering and moaning under the shower.

When it was over she turned around and showed surprising strength as she pulled me into a passionate, needy kiss. There were teardrops of release running down her face, she really felt like she had to gather and hold her deep emotions, which nature said had to be shared, in from the others.

She never felt like this, intimate, satisfied and connected to another person all at once. She never got it from her older exchange partners, to them she was just a warm vessel to put a cock into and rub. She needed to hold me for a minute, to share the human contact. In her life of self-pleasure it was something she knew was there, but had always suppressed.

Now I had spoiled her, masturbation would never again be her best choice, only the substitute until she found somebody she could open up herself to.

When we got out of the shower she would have other things on her mind, we both knew I was going to pass her to the other team members to fuck. But in a day or two she was really going to want to relive this with me.

After the climax and the kiss she calmed down quickly. She washed her face and, when I looked away, she washed her butt. Then we dried off and returned to the bedroom.