My Date Part 5-7 (F/M)

[Otkfme2]

My Date Part 5

I was real anxious to see Jane, again. Last time I saw her we had a
wonderful time eating at a fine restaurant. The bad thing was that my
credit card was up to it's limit, and it was declined. So Jane paid for
everything, and I had to pay her back. What made things even worse for me,
when we got back to her house, she spanked me. As a child my parents
spanked me, but Jane was the first grown woman to spank me. At first, it
was when I was late picking her up for the date. But now, it seems like
she finds any excuse to spank me. This may sound strange, but I think I am
starting to enjoy being spanked by Jane. Her spankings do hurt, I felt her
last spanking for most of the week, but it shows that she really cares
about me. I also enjoy going over her lap for an over the knee spanking.
It puts my naked body close to hers.

Anyway, this is what happened on Saturday. Jane said she was inviting
her girlfriends over to meet me. So when I arrived, on time, at six
o'clock, her friends were already there. It was a potluck, and the food
was already arranged and the table set. As I walked in, Jane quickly
introduced me to everyone. One of her friends that were there was Mary,
who Jane let spank me one time when I was late. Besides Mary, there were
four other women besides Jane. They seemed to want to get eat real fast,
and they said that I could go first. The food was good and I answered a
lot of questions. I told them that I worked in research at a computer
company, and I really enjoyed my work. I also told them that it was nice
to meet this many women, all at the same time.

After we ate, they had me sit out in the living room while they cleaned
up everything. After they were done with the clean up, they all gathered
in the living room. Each woman was wearing a number, from 1 to 6, and they
also gave me some packages to open, which were also numbered.

Jane said, "the packages are not for you to keep, but they contain
things for a game we will play tonight. Each of my friends has brought
something for the game. So start opening the packages."

I didn't know what to expect, and the first one contained a ruler. Jane
said to put it on the coffee table, and put the number from the box, next
to it. The next box I unwrapped contained a wooden spoon. This also went
on the table with a number. The next boxes contained a glove, a ping-pong
paddle, a hairbrush, and the strap that Jane had used on me to spank me.
Now I knew that I was probably in for another spanking.

Then Jane reached over and handed me one more box. When I opened this
box, it had a die in it and a sheet of paper that said, "Rules of the
Game."

All the women wanted me to read the rules out loud so that we could
start the game. I read the rules out loud and they said:

"This is a game so that my friends can get to know you better. It is a
simple game, but it should be an enjoyable game for all of my friends.
When you first roll the die, it will determine who spanks you. If you
notice, everyone is now wearing a number. When you roll the die, again, it
will determine which spanking implement they will use. After you gave
rolled the die twice, you are to pick up the spanking implement and take it
to one of my friends who is wearing that number. Then you are to ask her
to please spank you. Each of my friends will be allowed to spank you
twenty times with the chosen implement, and in whatever position they
chose. This may be bent over the couch or table, an over the knee spanking,
over a chair, or whatever they choose. The game will be over once everyone
has spanked you. Depending on how you roll the die, you may be spanked by
the same person more than once. Once you are ready to start the game, Take
off your shoes, socks, and shirt, then come over where I am seated. Jane."

This was really unexpected for me. Jane must have told her friends that
she spanks me, and all of them must have joined in to think up this game. I
took off my shoes, socks, and shirt, and went over to Jane.

"See how well he follows what I say to do," Jane said. "This is one of
the reasons I like Clyde so much. I always spank his bare bottom, and you
should, too." Jane undid my belt, unzipped my slacks, and guided them to
the floor. "See, he is wearing shorts, I like that, too." Then her fingers
were in the waistband of my shorts, and then I was standing naked in front
of all of her friends. Jane lifted up my feet so that I could step out of
my slacks and underwear. "Slowly turn around so that everyone can see your
nice bottom and penis and balls." It was so embarrassing being completely
naked in front of all these women. They were all commenting on how I
looked.

Then all of them started saying, "Roll the die so that we may start
spanking you!"

So I picked up the die and rolled a 2. I looked around the room and
Cindy, a cute blonde, was wearing number 2. I rolled it again and came up
with 3. On the coffee table, number 3 was the ruler.

"Clyde, now you need to go up to Cindy and ask her to spank you with the
ruler," Jane said.

So I took the ruler and handed it to Cindy saying, "Cindy, please spank
me with the ruler."

"I would be delighted to," Cindy replied. She got up out of her chair,
grabbed my penis and said, "Follow me. I want you to bend over the end of
the couch."

After I had bent over the couch, Jane said, "Spread your legs, Clyde,
like I have you do for me when I spank you." It hurts more when my legs are
spread in this manner, because then my whole bottom is exposed. Also, it
allows them to see my penis and balls. "This goes for Cindy and everyone,
before you spank Clyde, you can feel him between his legs if you wish."

Then I felt Cindy's hands feel my balls and stroke my penis. "I see why
you like him as a boyfriend," Cindy said. "Now get ready for your
spanking."

SPANK. "One", I said. The ruler stung me, but it didn't hurt very
much.

SPANK. "Two," I said.

"Does Jane spank you very often?" Cindy asked.

"She didn't spank me on our first dates, but since I have been coming
over to her house, she has found a reason to spank me sometime during each
date," I replied.

SPANK. "Three,"

"Do you like being spanked by Jane?" Cindy asked.

SPANK, SPANK, SPANK. "Four, five, six. I like to please Jane and be
close to her." I replied.

SPANK, SPANK, SPANK. "Seven, eight, nine."

"But do you like being spanked?" Cindy asked again.

SPANK, SPANK, SPANK. "Ten, eleven, twelve. It warms my bottom and it
makes me sexually excited, so I guess I like them, but the spankings give
me a sore bottom."

"They are suppose to make your bottom hurt," Cindy said.

SPANK, SPANK, SPANK, SPANK. "Thirteen, fourteen, fifteen, sixteen."

"Well, your bottom is just starting to turn red. Here's your last
four."

SPANK, SPANK, SPANK, SPANK. "Seventeen, eighteen, nineteen, twenty."

Then Jane said, "Clyde, thank Cindy for spanking you, then get up and
roll the die again."

So I said, "Cindy, thank you for spanking me." And I got up and rolled
the die, again. This time it was the number one. I looked around the room
and Mary was wearing number one. I rolled the die again, and it was #4,
which was a hairbrush.

I took the hairbrush over to Mary and she said, "I'm so glad I get to
spank you, again. I'm going to sit in the middle of the couch, so lie over
my knees." After I was over her knees she said, "Remember to spread those
legs!" Now my penis was between her legs, and she was holding my arms in
the middle of my back so I couldn't move about. "You don't have to count
these. SWAT It was so SWAT good that Jane SWAT let me spank you. SWAT Now
I am SWAT spanking my boyfriend. SWAT It has gotten SWAT closer together
SWAT and I believe SWAT that he actually SWAT enjoys being SWAT spanked by
me. SWAT He is treating SWAT me much better SWAT now. I believe SWAT
every man SWAT needs a spanking SWAT now and then." SWAT, SWAT, SWAT.
"Stand up, now, and see who spanks you next.

I had just received my first forty spanks and I had at least sixty to
go. My poor bottom was already burning. I rolled the die and got 5, which
was a redhead named Sue. I rolled again and got 6, which meant the strap.

Jane said, "Sue, the best way to give him the strap is over the back of
a chair. Everyone should help hold Clyde in place. He tends to move about
a lot when he is strapped." Then Jane put a chair in the middle of the
room, and I bent over it. "Everyone come over here. There should be on of
you on each of his arms and legs."

So now I was being held in place by all of Jane's friends while being
strapped. They did a good job, because I jerked about a bit.

It went on like this until every one of Jane's friends, including
herself, spanked me. Although I had a very sore bottom, I still had an
erection. Jane saw my state of being and said, "Clyde has been a good boy
to endure this spanking. Let me reward him by jerking him off."

Then she led me over to the couch. "Mary, hold his hands behind his
back and everyone else gather round." Jane said. Then Jane stroked my
penis until I came in front of all of her friends. Since everyone had seen
me naked, and had spanked me, I was told to leave my clothes off for the
rest of the evening.

Before any of her friends left, they were told that they could help
spank me, at any time. This was some evening, I got to meet Jane's
friends, and they really got to know me better. I had a very sore bottom,
and I wondered what was going to happen to me the next time I had a date
with Jane.

My Date-Pt 6 Jane's Mom

It was a Saturday night and I had another date with Jane. I didn't have
to work, so I allowed plenty of time to get to her house. I didn't want to
be spanked for being late, again. When I arrived, I rang the doorbell and
Jane yelled out for me to go ahead and walk in. Seated on the couch were
Jane and an older woman. They both stood up and Jane said, "Clyde, I would
like to introduce my mother to you. And mother, this is Clyde."

"Glad to meet you, Mrs. Miller," I said.

"Oh, you can just call me Kathy," her mother said. "Jane has been
telling me a lot about you. Would you mind sitting on the couch by me, I
have some questions to ask you?"

"Sure, I would love to visit with you," I said.

"Good, Jane why don't you sit in a chair over there, for now." Kathy
said. I sat down on the couch beside Jane's mom. She didn't seem old
enough to be Jane's mom. Kathy was wearing a white blouse and a short
black skirt. "I guess you have been dating my daughter Jane for about
three months, is that true?"

"Yes it is!" I replied.

"And do you like my daughter?"

"Yes, I even love her. We are so compatible with each other. We even
share the same ideas and values."

"Jane tells me that you have even met her friends."

"I have met her friends," I replied. I didn't want to mention the fact
that they also spanked me.

"If you like my daughter so much, why haven't you introduced her to your
friends?"

"I guess I haven't got around to that."

"And Jane hasn't seen your house, yet!"

"I guess your right, she hasn't seen my house." I replied.

"Jane also tells me that you have already had sex with her. Is that
true?"

I stared at Jane and said, "You told your mother that!"

Kathy abruptly said, "Clyde, I'm talking to you. Please answer the
question. Have you had sex with her, already?"

"Yes we have," I answered.

"Jane also tells me that she has spanked you. Is that also correct?"

"Yes it is," I reluctantly answered. I looked over at Jane. She had a
smile on her face,

"Do you want to keep seeing my daughter?"

"Very much so, Mrs. Miller," I said.

Well, I believe that you should be spanked for how you have treated my
daughter so far. You say you love her and you have had sex with her, but
yet, you have NOT shared your life with her. That is disrespectful to my
daughter. Don't you agree."

"When you put it in those terms, I guess I agree with you."

"Although Jane now has her own house and is a grown woman, I still need
to make sure my daughter is treated with respect by anyone who dates her.
Don't you agree?"

"Yes, I think it is good that you care about your daughter."

"Good. Then you agree to be spanked by me for being disrespectful to my
daughter!"

I hadn't realized that I had agreed to be spanked by Jane's mother.
"Did I agree to a spanking?" I asked.

"Yes you did. Now stand in front of me while I prepare you to be
spanked." Kathy commanded. Slowly, I got up from the couch and stood in
front of her. "Put you hands on top of your head and keep them there."
Then she unbuckled my belt, unbuttoned my slacks, unzipped my zipper, and
pulled my slacks down to my ankles.

"I see you are wearing boxer shorts, just like Jane said you would be.
But this is going to be a bare bottomed spanking, so down they go." Kathy
reached her fingertips inside the waistband of my boxer shorts, and slid
them down my legs. I was now standing naked from the waist down, in front
of Jane's mom. I felt so embarrassed.

"I can already see why Jane likes you. Step out of your things so that
they will be out of the way." I lifted my feet and she completely took off
my slacks and under shorts. "Jane, why don't you take these and put them
out of the way. Clyde will not be needing them, for a while." Jane picked
up my clothes and put them in a corner and sat back down in a chair across
from where I was standing. "Keep you hands on your head and turn around so
that I can see your bottom."

I turned around and felt her hands on my bottom. "Jane did say that you
had a firm bottom. I guess she is right about that. You may drop your
arms, stand by my side, and lay over my lap."

Kathy hiked up her skirt, and I felt like a little boy about to be
spanked by his mommy. "I'm going to start you out with a hand spanking."
SPANK, SPANK, SPANK "I want my daughter to be treated with respect." SPANK,
SPANK, SPANK "Did Jane also tell you that I spank her dad." SPANK, SPANK,
SPANK.

"No," I replied.

SPANK, SPANK, SPANK "It is good that Jane spanks you." SPANK, SPANK,
SPANK "I guess it runs in the family." SPANK, SPANK, SPANK "Your spanking
will have two more parts to it." SPANK, SPANK, SPANK "The second part for
not sharing more of your life with Jane." SPANK, SPANK, SPANK "And the
third part for having sex with her, already." SPANK, SPANK, SPANK

Kathy spanked me for about five more minutes then said. "You can get up
now, and take off your shirt. Hand it to Jane and then bring over the
paddle from the table. Jane, take his shirt and then move one of your
wooden chairs to the center of the room." I took off my shirt and handed it
to Jane. Then I got the paddle from the table and handed it to Kathy.
"Now put your knees on the seat of the chair and bend over it." I was now
totally naked and bent over the chair, ready for Jane's mom to paddle me.

"You would make a good husband for Jane. She told me that you even
accepted a spanking from her girlfriends. Is that true."

I felt embarrassed that Jane had told her this, but I replied, "Yes it
is true, they did spank me."

"A well-spanked man is a well-behaved man," Kathy said. "Now get ready
for 30 swats from the paddle."

SWAT, SWAT, SWAT, SWAT, SWAT. "So you are now going to have Jane met
your friends." SWAT, SWAT, SWAT, SWAT, SWAT.

"Yes, madam," I replied I wanted to make sure I answered Jane's mom with
respect.

"Very good." SWAT, SWAT, SWAT, SWAT, SWAT. "And you are going to show
her your house." SWAT, SWAT, SWAT, SWAT, SWAT.

"Yes, madam," I replied.

SWAT, SWAT, SWAT, SWAT, SWAT. "And are you always going to respect my
daughter?"

"Yes, madam." SWAT, SWAT, SWAT, SWAT, SWAT.

My bottom felt on fire, and I knew that there would be a third part to
my spanking. "Now stand up and don't rub you bottom. Walk over to the
side of the couch and bend over it."

I did so then she said to Jane, "Do you have something else that I can
spank him with?"

"Yes, a strap. I have used it on him, before." Jane replied.

"Good, go and get it." Jane left the room to get the strap. "This will
be for having sex with my daughter, already. I don't want you to take
advantage of her."

"Here's the strap, mom." Jane said.

"Clyde, you will receive six strokes of the strap. I expect you to
count these out and stay in place."

SWAT. "One." It really stung on my already well-spanked bottom.

SWAT. "Two."

"After your six strokes, I want you to stand up and thank me for
spanking you. Then bend over the couch, again. I am sure that Jane will
want to give you a few more strokes of the strap. Do you understand,
Clyde?"

SWAT. "Three. Yes, madam."

"And if I hear from Jane that you have been disrespectful to her, you
can expect another spanking from me. Is that understood?"

SWAT. "Four. Yes madam."

"I hope Jane keeps going out with you."

SWAT. "Five."

"You seem like a nice man."

SWAT. "Six. Thank you, madam."

"You can stand up, rub you bottom, and thank me."

Although I had an erection, I stood up and rubbed my bottom and said,
"Thank you for spanking me, Mrs. Miller. I really do love your daughter
and hope to marry her some day."

"That is good to hear," Kathy answered. "Now bend over the couch,
again, so that Jane can finish your spanking."

As I bent over, Jane's mom said, "I'll let myself out. It was good that
I got to met and spank Clyde."

"Talk to you later, mom." Jane yelled.

I heard the door open and shut and then Jane said to me, "I am very
proud of you." SWAT "And I am glad that my mom got to spank you." SWAT "It
shows me that you really do love me." SWAT "And you do respect me." SWAT

"You can stand up, now." I stood up, rubbed my poor sore bottom, and
Jane threw her arms around me. We kissed and kissed, and then we made
love. I wondered what my next date would be like with Jane!

MY DATE - Pt 7 Jane's sister

I went out with Jane a couple more times, showed her my house, and she
met a few of my friends. It was getting close to Thanksgiving, and she
invited me to a family gathering. It would take place at her sister's
house, Connie, who lived fairly close to Jane. Since we were going out
pretty steady, Jane thought that I should be included in her family events.
I had met and been spanked by her mom, but had not met her dad yet, or her
sister, Connie.

When Thanksgiving morning came around, I picked up Jane and we went to
Connie's house. I met George, Jane's father, and Roger, Connie's husband.
Jane's sister was about five years older than Jane, and also looked real
cute. Roger, her husband, was about my same height and build, and he
worked for the Fire Department. I guess Roger and Connie had been married
for about five years.

We sat around the table, ate good food, and her family asked me a bunch
of questions. I told them that I was in love with Jane and that I hoped
that we would marry each other in the future. Her family was very pleasant
to be around.

Around three o'clock, Jane's mom and dad had to leave. They had another
event they needed to attend. Shortly after that, Roger, Connie's husband
had to leave on a fire call. That left just Jane, Connie-Jane's sister,
and myself. They wanted to talk some more, and they had me sit in the
middle of the couch, with Jane on one side of me, and Connie on the other.

Connie said, "It's good that everyone has left. Now I can really get to
know you a lot better, Clyde."

"Okay, what else do you want to know about me?" I asked.

"Has Jane told you that I spank Roger?" Connie asked.

Spanking was never mentioned until now, and I was hoping it wasn't going
to be brought up. But I answered, "No, she hasn't."

"And is it true that Jane spanks you?" Connie asked.

"Yes it is," I answered. I turned to Jane and said, "You told your
sister that you spank me!"

"We keep no secrets in this family," Jane replied.

"And our mom has recently spanked you, as well as Jane's friends?"
Connie asked.

"Yes, it is true." I replied.

"I know that you haven't done anything recently to deserve a spanking,
but I would like to spank you, Clyde," Connie said.

Jane jumped in and said, "You have been spanked by everyone else, let
Connie spank you!"

"I will only spank you if you agree to it on your own free will." Connie
said.

"Please let Connie spank you," Jane said.

I was hoping that I won't be spanked on Thanksgiving, but I said to
Connie, "Okay, I guess I will agree to be spanked by you."

"Good, I didn't want to be left out in being able to spank you. But
before I spank you, let me show you and Jane the rest of the house."

Jane showed us the bedrooms on the first floor, and then she took us
down to the basement. There was what looked like a woodworking shop in the
basement. "Roger is real good with working with wood. It's just a hobby
for him, but he could probably start a business of making things out of
wood for people. If he see something, or even a photo of something, he can
usually make it out of wood." There were a lot of saws, hammers, and many
woodworking tools.

Jane then led us to the next part of the basement. There was a room
that was locked, and as Connie unlocked the door, she said, "This is a room
that even our parents don't know about. They think it is a storage room."

When Connie opened the room, it was carpeted, and it had various
paddles, whips, etc., hanging on the walls. In the middle of the room were
various spanking benches, wooden horses, and other wooden devices. And on
the wall, was a wooden X, and other wooden things that one could be secured
to.

"I had no idea that you had a room like this in your house," Jane said.

"Yes, I had no reason to show it to you until now. This is where I
spank Roger. Roger also made most everything that is in here, except for
the spanking implements, of course. And since Roger and Clyde have about
the same build, they should also work real good on Clyde."

"I still can't get over this room," Jane said as she was looking over
the various spanking furniture,

"Clyde, you said that you would submit to a spanking from me. So I want
you to take off all of your clothes, except for your under shorts, then
come over to where I will be sitting." Connie said.

I thought that I would just receive an over the knee spanking from
Connie, I wasn't expecting this! As I undressed, Connie sat on a chair and
Jane stood next to her. I walked over to Connie and she said, "Keep your
hands at your sides while I pull down your under shorts." Then I felt
Connie's fingertips in the waistband of my under shorts, and she slid them
down my legs. "Step out of them, please." Now I was standing totally naked
in front of Jane's sister, with Jane watching. Next, Connie surprised me
by grabbing and fondling my penis and balls. I started to have an erection
and Connie said, "Good, he reacts like Roger does." Then she released my
penis and balls and said, "Turn around, and remember to keep your hands at
your sides."

I turned around, and immediately felt her hands on my bottom. "He does
have a nice butt. It will be fun spanking him." Connie said.

"I'm glad you are finally going to have a chance to spank, Clyde." Jane
replied.

Then Connie stood up, grabbed me by the penis, and led me over to a
piece of spanking furniture. "This is something I really like to spank
Roger on. Let's try it on Clyde."

The front of it looked like a stock. It had holes for my wrists and
neck. But the bottom of it was about one and a half feet off the floor,
and it had two small platforms that were spaced about three feet apart.

"Get up on this. Put one knee on each side, and bend over so that your
neck and wrists are in the stock." It took a little bit of maneuvering on
my part, but soon my legs were spread, and I was bent over with my head and
wrists in the stock. Connie closed it, and now I was held in place by the
stock and was unable to see what was going on behind me.

"Jane, there are straps by his knees. Watch what I do, and secure his
knee in place while I take care of his other knee." Then I felt the straps
go around each thigh, near my knee. "Also, the are ankle straps to secure
his foot in place." The I felt both feet secured to this device. Now my
legs were spread wide apart, I was fully bent over, and I was secured in
place.

Connie then said, "I like to spank Roger on this device because his
bottom is fully exposed, and I can also easily get to his penis and balls."
With that she grabbed my penis and balls, again.

"Yes, I see what you mean," Jane said.

"I'm going to start your spanking out with a paddle," Connie said. Then
she started to paddle me. While she was spanking me, she said to Jane, "I
have already discussed this with Roger, since I found out that you spank
Clyde. You can borrow this room at any time. Just call me first, to make
sure I am not spanking Roger in it. I would also be willing to help spank
Clyde in the future, so you will know how to use everything in the room."

"That would be great!" Jane said. "We live so close, so it would be
easy to bring Clyde over here for his spankings. Don't you think so,
Clyde."

I was in no position to object, so I just said, "I guess so."

"I guess so, what?" Connie said as she spanked me with the paddle.

"It would be nice to bring me here to spank me," I said.

"That's good to hear you say that, Clyde." Jane said. "Connie and I
will have fun spanking you in her special spanking room."

"Let me show you what a riding crop can do." Connie said. It stung a
lot more than the paddle. I tried to pull away from it, but I was securely
in place. "And if you get tired spanking him on his butt, you can use it
on his balls and penis." Then I felt her tapping my balls and penis with
the crop. Being so exposed in this position and with her tapping me, I
immediately had another erection. "See how he reacts to the crop."

"Very good," Jane said. "Let me try the crop." Then Jane spanked me and
tapped my penis and balls with the crop.

"This position lends itself to something else," Connie said. I heard
various noises behind me, and then felt a jelly or lotion being rubbed
around my asshole. It actually felt good, compared to the spanking I had
until now.

"Have you ever put your fingers inside of him?" Connie asked Jane.

"Put on a glove like I have on. Lubricate your fingers, and try it. Do
it slowly, and start with one finger." Connie said.

"Okay, I'll try it!" Jane said.

"What's nice about having him on this device, is that his butt checks
are already spread wide apart for you." Connie said.

Then I felt Jane's finger slowly go into my asshole. It actually was a
big turn-on for me. She even stuck her other finger in, then a third, and
she felt around inside me.

"See how he is reacting to it," Connie said, as she grasped my penis.

"I guess it really excites him." Jane said.

Then Connie said, "I think Clyde has had a lot of excitement for one
day. Let's take him down off of this, then I have one last thing to do to
Clyde." They released my legs, and raised the half of the stock, so I was
able to stand again. Then Connie led me by my penis to another spot on the
room. "Stand still and hold out your wrists." Connie put wrist cuffs on
me, secured them to a bar above me, and raised it up. "Spread your legs"
Then anklets were put on me, and a bar was secured between my legs. "This
is called a spreader bar. It keeps his legs apart. Let's also blindfold
Clyde, so he can't see what is happening."

A blindfold was put on me, and then I felt a condom being put on my
erect penis. "This is so that you don't mess up the carpet." Connie said.
"Jane, I will spank him while you make him cum. Let's start!"

What a sensation! I was feeling pain and pleasure at the same time.
Soon I was shooting cum into the condom.

Connie took off my blindfold, and said, "You took your spanking very
well. I look forward to spanking you, again." She released me, and she
showed me to the bathroom, where I could get rid of the condom and clean
myself up. "You can get dressed now, we will be waiting for you upstairs."
Connie said.

When I got upstairs, Jane said that I could expect many more spankings
like this one from her and Connie. She was also interested in trying the
other spanking benches and spanking furniture.

[Switchbott]

Excellent, the addition of the spanking room and the sister was great!