Settlement Night #2 Settlement Night #2 With the closing credits to A Current
Affair scrolling across the screen, Tom looked over at Debbie, who was staring
straight ahead. "It's time, Debbie. Let's go do it and then it will be over."
Debbie said nothing but closed her eyes and clenched her fists in nervous
anxiety. Since coming to my apartment from work, she had changed out of her
business suit and was now wearing a pair of light gray cotton gym shorts and
an oversized pale blue t-shirt she had brought with her. Tom stood up, took
Debbie's hand and helped her off the couch. She still said nothing as he led
her out the door of his apartment and along the sidewalk to her and Cindy's
place. Cindy answered the door immediately after Tom knocked and invited the
two inside as if they were old friends coming over for a night of cards. There
was an unmistakable air of satisfaction in her welcoming smile and it was
obvious that she was going to savor every minute of this. "Tom, can I get you
something to drink?" Cindy asked as she led the way to the living room. Tom
declined the offer as he didn't want to further embarrass Debbie by acting
like this was a social gathering. In the living room, Tom saw the regular
furnishings, the leather sofa and loveseat, coffee table and entertainment
center. In the middle of the room he also saw that Cindy had placed one of the
chairs from the dining room set. Debbie and Tom sat down on the sofa and Cindy
chose the love seat across from them. Still wearing her expectant smile,
Debbie began the proceedings with some introductory remarks which seemed
designed to cause Debbie as much embarrassment as possible. "I glad you could
both make it tonight," she began, highlighting the fact that Debbie would have
preferred to be anywhere else in the world at the moment. "As you know, the
purpose of our gathering is to settle a little dispute between Debbie and
myself and Tom has graciously offered his time to assist in the settlement.
Turning her attention to Debbie, she continued her humiliating opening
remarks. "Debbie, your punishment will consist of a thorough spanking session
to be administered by Tom. Your punishment will continue until I am satisfied
that your debt has been paid. You are not to argue with Tom or me at any time,
nor show any disrespect. From this moment until the end of your punishment,
you will follow my directions as well as Tom's without delay and you will
address me as "Ma'am". I do not plan to participate in your spanking but I
reserve the right to change my mind at any time. When your punishment is over,
you will issue an apology for your behavior and all the distress you have
caused me and then thank Tom for taking time out of his day to come over and
spank you. Do you understand and agree with these directions as I have
explained them?" Debbie could barely speak her mouth was so dry. She managed
to croak out a weak "Yes, Ma'am" while staring at her feet. She could not
bring herself to face her roommate and wanted to sink into a hole in the
ground and just disappear. Tom, would you care to continue?" This was Tom's
cue to begin Debbie's spanking. As had been previously agreed, Tom would
maintain a proper disciplinary tone during the spanking. He was simultaneously
thrilled at the thought of what was about to happen, yet sympathetic toward
Debbie who looked so small and helpless at the moment that his heart went out
to her. Cindy had laid in on rather thick but that was part of the arrangement
so she was within her rights. Tom looked over at Debbie on the couch for a
moment without saying anything. He admired her shapely, tan legs and her slim
sinewy arms which she had tightly wrapped around her chest. He took a glance
across at Cindy who could barely contain her glee. Tom took a deep breath to
calm his racing pulse, ran his hands across his shirt to dry them of some
nervous perspiration that was forming, and locked his gaze on poor Debbie.
"Debbie, I'm going to start you off with a warm up spanking. Please stand up
and remove your shoes before we begin." With that he slid over to the center
section of the leather sofa as Debbie stood up on wobbly legs and reached down
to untie her small Reebok tennis shoes. She took them off and slid them, along
with her socks, under the coffee table with her foot. She then turned and gave
a meek glance over at Tom, a look that was half pleading and half resignation.
Tom reached out and took hold of Debbie's left hand and gently pulled her
toward him. When she was standing in front of him, he reached out and untucked
her loose t-shirt from her soft gym shorts. The shirt extended down past her
shorts when he let it go. He then moved his hands under the hem of the t-shirt
and into the waistband of her gym shorts. He smoothly lowered the shorts past
her bottom and let then slide down her legs. Debbie stepped out of the shorts
and then picked them up and placed them on the coffee table. Tom extended his
hand to her and said, "Ok, Debbie, come across my lap." Debbie gave a final
grimace of despair and then complied with the command. She placed her left
knee on the sofa, placed her left hand on Tom's right arm to support herself,
then swung her right knee onto the sofa and leaned forward, placing her bottom
squarely across Tom's lap. It took her a moment to get settled, with her feet
stretched out fully behind her and her arms folded under her face. Debbie's
thin t-shirt covered her bottom so Tom took hold of the shirt's hem and lifted
it up above her waist, revealing a pair of pale yellow Victoria's Secret
Second Skin Satin panties in a french cut style. Tom folded her shirt hem over
and placed it onto the small of her back. Tom had never seen Debbie in her
underwear before, although she liked him and figured after a couple more dates
with him they would be at that level. Tom couldn't help running his right hand
across Debbie's silky smooth bottom a couple of times before realizing that he
had a job to do. "Be brave, Debbie" Tom said as he placed his left had on the
small of her back and shifted his position on the sofa to adjust her bottom
slightly on his lap. He raised his right hand and brought it down with a
moderate slap across the center of Debbie's waiting bottom. He let his hand
stay on her bottom for a minute as Debbie let out a small gasp, more from
surprise than pain. He lifted his hand again and began a steady spanking
rhythm, covering Debbie's entire bottom but not too hard at the beginning. He
continued to spank her for about a minute, stopping a couple of times to
smooth out the back of Debbie's panties. Debbie let out the occasional moan
but remained in position and offered no resistance. Tom could not imagine the
courage it took Debbie to submit to this form of punishment and with each
spank his admiration for her grew. For her part, Debbie was unable to
concentrate clearly on anything, her mind a swirl of conflicting emotions,
anger at Cindy, anger at herself for getting into this mess, but mostly
embarrassment at the sight she must be presenting with her bottom on display
and receiving its due punishment. Tom stopped spanking long enough to adjust
the back of Debbie's shirt again, which was starting to drift back toward her
waist and to give Debbie a quick pat on the bottom as he instructed her to
"Lift you hips for a minute." After a short delay, Debbie lifted her hips
slightly and Tom used the opportunity to slip a couple of fingers from each
hand into the wide smooth satin band of her panties and begin to slide them
down over her bottom. He continued lowering the panties to Debbie's upper
thigh and then put his left hand back on the small of her back and gave a
slight push to let her know she could lower herself back into position. Tom
ran his hand lightly over her warm bottom and was surprised it was already
warm after a relatively small amount of attention. "Look whose bare bottom is
already turning pink from her spanking," Cindy piped up form across the room.
Tom took his eyes off of his lovely task at hand for a moment and saw that
Cindy had her knees locked together and wore an expression of eager
anticipation with her hands knotted together in her lap. Debbie had her eyes
closed as she couldn't bear the thought of looking over at Cindy and seeing
her smug grin as Debbie went through her ordeal. Tom continued Debbie's
spanking, now across her smooth, shapely bare bottom. He increased the force
of his spanks and could feel Debbie twitch a little with each smack. He
concentrated on her bottom but ventured lower for a few slaps across Debbie's
upper thighs. These seemed to bring more of a reaction from Debbie. Debbie had
not been spanked since she was a child and was totally unprepared for the
experience. She had been able to think of little else for the past week, and
went over countless scenarios in her mind trying to imagine how the spanking
would feel and how she would react. Now that she was getting her bottom
warmed, she realized that no amount of speculation could prepare her for the
intense emotional reaction she was feeling at the moment. As Tom continued to
spank away, Debbie was so overwhelmed that she could not describe even to
herself exactly what she was feeling, the mix of pain, embarrassment, and
utter submission. Tom gave her about fifty spanks with her panties down, and
the last ten were applied significantly harder that the others. Cindy could
not contain her excitement as Debbie's bottom gained hue. She got out of her
chair and walked over to the sofa to get a closer look. When Tom stopped
spanking, Cindy reached out and ran her own hand over her roommates red
bottom, continuing to rub in a circular motion while she enjoyed the heat that
Tom's warm up spanking had generated. When Debbie felt Cindy's hand touch her
bottom, she reacted by trying to turn around on the couch and saying "Hey,
what are you doing. Tom, don't let her do this, pleeeease." Cindy reacted by
giving her roommate a sharp slap on the bottom and saying, "I was just
inspecting Tom's handiwork. Remember, your spanking is being for my pleasure.

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I also don't remember asking you to speak." She ended her rebuke with another
sharp smack, causing a small shriek from Debbie. Tom would have been happy to
keeping Debbie right where she was because frankly her body felt great lying
across his lap and he hated to let the moment go. However, he decided it was
time to move on to the next phase of the punishment. The deal was for a very
thorough spanking and he knew Debbie would not be allowed to leave until Cindy
was more than satisfied that justice had been served. He raised Debbie's silky
panties back into place and lowered her t-shirt before helping her up from her
position across his lap. He stood up and led Debbie to the armless chair that
had been placed in the middle of the room. "Cindy, I believe you said you
indicated last week that you were going acquire a wooden hairbrush for
tonight's punishment. Is it handy?" Cindy went back to the love seat where she
had been sitting and grabbed the hairbrush from the floor next to the chair.
She walked over to where Tom and Debbie were standing, and showed the brush to
Debbie with a wicked grin before handing it to Tom. Cindy continued to torment
her ex-friend with her taunting comments. "Debbie, how is your bottom feeling?
It's looking rather red from here. That's got to hurt. Tom is doing an
excellent job on you so far, isn't he?" "Yes, Ma'am" was all Debbie could say
without risking increased punishment. Cindy continued her assault. "Debbie,
remove your t-shirt now. You won't be needing it for a while and I think its
only fair that Tom enjoy the view as he labors with your punishment." Debbie
looked at Tom with a pleading look. Tom could only shrug in response and say,
"I'm sorry, Hon, it's Cindy's show." Realizing she had no leverage whatsoever
in this ordeal, Debbie took hold of her shirt and lifted it up and over her
head, revealing a satin bra to match her panties. Tom thought she looked more
than a little adorable at the moment even in her predicament, and felt himself
becoming aroused. Before his crotch gave his feelings away, he sat down in the
chair and took Debbie back across his lap. Amazingly enough, the two of them
handled the process like old pros. Debbie bent right over his knees like she
had been doing it for years. Tom gave her a couple of quick adjustments and
her bottom was once again centered over his lap and awaiting his attention.
Without further ado, Tom lifted the large wooden hairbrush and brought it down
with a load crack on Debbie's warm bottom. She screamed out at the first blow
and squirmed on Tom's knee but did not try to escape. Tom continued to deliver
sharp smacks with the brush, figuring he would let her get used to the brush
with her panties on before taking them down. Also, her position over the chair
exposed her rear end much more prominently than had been the case on the sofa.
Tom gave about 25 smacks before stopping. He put the brush down for a moment
in the small of Debbie's back and once again lowered her panties. Her bottom
was redder that when he had last viewed it just moments ago. He continued
taking her panties down to her knees before picking up the brush and resuming
his duty on her captive caboose. Now he really let rip with the hairbrush. He
had never spanked a woman before and had no idea how much pain Debbie must be
feeling, but he wanted to convince Cindy that Debbie was truly being punished
so she would declare an end to the session. Debbie did her part to lend
believability to the proceedings. By now, she was yelping loudly with every
brush stroke and was quickly losing her composure, on the verge of sobbing
uncontrollably. Tom continued with his assault until Debbie broke down
completely. He glanced over at Cindy who was back in the love seat watching
intently. She nodded her approval as Tom landed the last few hard strokes to
Debbie. He finally put down the brush and checked on her bottom with his hand.
Wow! It was a shot as a car dashboard in the middle of summer. Debbie was
still sobbing and it took her a minute to realize that Tom had stopped hitting
her. Her bottom stung so bad by now that she wasn't sure if it felt hot, cold
or just pain hurt. She had totally forgotten her anguish at having her panties
lowered again until she felt Tom slowly pulling them back up her thighs and
over her scorched rump. She winced as the garment was pulled back into place
and had trouble standing as Tom lifted her back to her feet. Tom looked at
Cindy with a questioning look. "Well, Cindy, how's she doing. Have you gotten
your pound of flesh yet?" Cindy walked over behind Debbie, kneeled down behind
her and lowered her panties for another up close inspection. Debbie tensed but
said nothing. Cindy rubbed Debbie's bottom all over, feeling the intense heat.
She slipped the panties back into place, stood up and said, "Tom, you've made
good progress here but I have one more item that I think Debbie should be
introduced to before I will be satisfied. With that she ducked out of the room
for a moment and when she returned she was holding a long thick leather belt.
"My ex-boyfriend left this over here and never picked it up when we broke up.
I think it's only fitting that my ex-roommate be treated to a strapping with
this belt. Maybe she can even return it to its owner when we're done with it."
Debbie started to protest her innocence in the boyfriend matter but was
quickly cut off. "Debbie, for the last time, you will not speak unless I ask
you a question. Not another word." Tom took Debbie by the arm and led her over
to the side of the leather sofa, hoping to get this final phase of the
spanking going. Before he could get Debbie bent over the arm of the sofa
however, Cindy chipped in with another command "Debbie, sweety, I think I
would prefer it if you removed your bra and panties for this portion of your
punishment. A strapping just doesn't seem like a strapping unless it is given
in the nude." Debbie knew better than to argue and she reached behind her to
unhook and remove her bra. She tossed it on the sofa and then slid off her
panties, baring her bottom for the third time in the last half hour. It almost
didn't seem like a big deal anymore since she did not feel she had any modesty
left to protect. She changed her tune when Tom bent her over the arm of the
sofa. As her elbows slid forward to rest on the sofa cushion, her heels lifted
off the floor so only her toes were touching. This was the most humiliating
position she had ever been in in her life. Her private parts could not
conceivably be put on better display to Tom than they were right now. Tom came
to the same conclusion at the same time and he feared his arousal was visible
if Cindy cared to glance at his trousers. Not knowing what else to do, he took
the belt from Cindy, placed in across Debbie's bottom to get the correct
range, and then lifted the belt and brought it down with a crash on Debbie's
backside. She screamed bloody murder at this new assault but by some force of
will did not try to escape her perch on the sofa. Tom brought the belt
whistling down again and again as he was determined to end the spanking with
this strapping. He wasn't sure how much more Debbie could take in her present
condition. Tom brought the strap down on her left cheek, right cheek, both
cheeks and on her thighs. One of the strokes landed on Debbie's exposed
privates which really made her shriek and which made Tom feel awful because he
was trying to avoid that particular spot. He looked over at Cindy to she if
she was becoming satisfied that Debbie had had enough. When he saw her, he was
surprised to see her holding a Polaroid camera. She came up close to the sofa
and snapped a picture right as I was landing another stroke with the belt. "I
plan to tell my friends in detail about Debbie's punishment and I want to have
some evidence around in case Debbie tries to deny that tonight ever happened,"
Cindy explained. Tom gave Debbie three more sharp slaps with the belt and
turned to Cindy and stated, "Cindy, I think she's been punished enough. It
looks like her bottom is starting to blister. I think you have to admit that
her bottom has easily received enough beating to more than make up for the fat
lip she gave you." Cindy put down the camera and once again inspected Debbie's
steaming bottom. She ran her hand over the various bruises and welts that
covered Debbie's entire bottom and upper thigh area. With a look of complete
satisfaction she addressed Tom. "I think you're right. I have to say I have
enjoyed every minute of this and I hope you have, too. All I need now is for
Debbie to give me the apology she owes me." Debbie, who was almost oblivious
to the conversation going on behind her, was helped into an upright position
by Tom. Tom fetched her panties and held them for her as she stepped into
them. He pulled them gently up over her hips until they were snugly in place.
He then handed her the bra from the sofa and said "Deb, honey, apologize to
Cindy for the trouble you have caused her and then we can go." Debbie managed
in a weak voice to issue the following apology. "Cindy, I'm very sorry that I
hit you and I am sorry for the pain it caused you. Thank you for agreeing not
to press charges. I appreciate chance to put this episode in the past." With
that she finished, Tom returned with Debbie's shirt and helped her put in on.
She waved away the gym shorts that were offered to her. Not surprising, Tom
thought. Tom kept the shorts and put his arm around Debbie. Without further
conversation of any kind, Tom led Debbie back to his apartment. When they were
inside his paced and seated on the couch. Debbie broke down crying and buried
her head in Tom chest. He gently picked her up and put her on his lap, put
both arms around her and rocked her back and forth while she had a good cry.
NO words were exchanged. Within twenty minutes Debbie had fallen asleep in
Tom's arms. Tom smiled to himself, turned off the lamp and enjoyed the feeling
of the sleeping Debbie in his arms. Within the next few minutes, Tom joined
Debbie in dreamland. The End 

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