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From: "Merv Saylor" <mervsaylor@hotmail.com>
Subject: {ASSM} {assm} My Best Friend's Mother [5/5] {femdom and humiliation}
Date: Mon, 24 Jan 2000 03:10:02 -0500
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The final installment.
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<1st attachment, "Best Friend's Mother.txt" begin>
CHAPTER 5
The sessions continued on close to a weekly basis for the next month.
There were certain rules that I was always required to follow. First of all
I would be given the day and time for each session. Secondly I was to
arrive on time and I have showered immediately prior to coming over to her
house. She always showered before I arrived and insisted that I do the
same.
Almost all of the sessions were with Pam, although I did have one other
with Toni on a weekend when Pam was not available. That session with Toni
had been much like my other one with her, I would go down on her and ream
her while she worked with my stamina by masturbating me until I got close to
coming and then stopping. I had to admit I liked the sessions with Toni
because in the end she would make me come with her hand. Toni was more into
the pleasure of the session and seemed less concerned about control and I
enjoyed the difference between the two ladies.
I had learned a lot in my sessions with these ladies. I had been taught
how to give them pleasure with my tongue. I had been taught how to bring
them to climax slowly. I would try to prolong the pleasure for them as long
as possible. Both ladies always had me start with their ass and after
bathing and teasing their little hole I would move on to pleasuring their
pussy and clit. I had become and expert at making them come. Pam seemed to
prefer more direct contact and attention to her clit while Toni loved me to
stick my tongue as far as I could get it inside of her when she began to
come. Pam had taught me how to make a woman come with my hand. She had me
watch her touch herself and then I practiced under her instruction. With a
little practice I became accomplished at gently stroking and rubbing her
clit until she could no longer hold back and would come with her thighs
trapping my hand against her crotch. I never got over how hard she would
come when I masturbated with my hand. The image of her face, eyes closed
and almost not breathing was something that always amazed me.
As I mentioned, Pam loved the control. She enjoyed embarrassing and
humiliating me, depending on her mood. Sometimes I would be made to wear
her panties while she chastised me, other times I would be made to put on
thigh high stockings or pantyhose and model for her. One time she had me
strip and get up on her kitchen table on my hands and knees while she
"inspected" my entire body, poking and prodding all the time. I was used to
sniffing and licking her panties while she watched with amusement, I would
follow her commands without hesitation as I truly wanted to please her.
Each session would end with her watching me masturbate.
The end of the summer was here and I was due to leave for college the next
weekend so I suspected when I arrived at Pam's house that this might be my
last session with her. I rang the doorbell and was greeted by her wearing a
new dress. As usual it was a loose fitting summer dress and ended a couple
of inches above her knees.
"Come on in," she said stepping back from the door. I brushed past her and
notice a hint of the perfume that she was wearing. I stopped in the middle
of the room and waited for further instructions.
"Don't you leave for college next week"?
I nodded my head, "next Saturday."
"Well then, it looks like this might be our last session for awhile."
I didn't want them to end but I was going away to college. "I'll be coming
home on some weekends." I replied hopefully. She smiled knowingly and
reached out and touched my cheek. "Well lets wait and see, who knows, maybe
I'll come and visit you at college some weekend."
I felt better, at least there was some hope that this whole thing would end
entirely.
"Well, there's one more thing that I would like to have you learn before
you go off to college."
"Sure, anything." I replied.
"Good, lets go get in the car."
We drove to a shopping mall a few miles away. As we drove there Pam
explained to me that women loved to have men buy them lingerie and that it
was important that I be able to go into a store and purchase some. I felt a
knot of dread in my stomach but at the same time I was excited. I was just
hoping that we would not run into anyone we knew.
We arrived at the mall and she parked her car. She then handed me twenty
dollars. "Here's some money, I would like you to go into the mall and buy
some new panties for me. I want you to buy some from the Victoria's Secret
store and I want you to buy some at one of the other stores. Buy as many
pairs as you can and I want you to buy something sexy. Who knows, maybe
I'll model them for you."
I took the money and entered the mall and headed first to Victoria's
Secret. Fortunately it was early and none of the stores were crowded. I
entered the store and quickly went about selecting my purchase. I chose a
thong that was on sale for $10.00. It was a deep rich purple and had a lace
front. I was already imagining how her pubic hair would look pressed
against the lace. I was also wondering in the back of my mind whether I
would be wearing these later that day. Although it was a little embarrassing
having the salesgirl ring up my purchase, I survived.
I next went to the department store, conscious of the Victoria's Secret bag
that I had in hand. I found the lingerie section on the second floor and
proceeded to find the display rack of panties. As I was looking a middle
aged lady asked if she could help me. I told her I was buying a present for
my girlfriend and kept looking. She seemed amused by my discomfort and
began asking questions about what style and color my girlfriend liked. As
she did this she would hold up various pairs for me and tell me how much
each pair cost. I found three pairs that were on sale for $9.99 and
selected those. All were string bikini style and were sheer in both the
front and back. One pair was a bright lime green, one pink (her favorite
color) and the other pair was white.
The saleslady folded each pair in tissue paper and put them in a bag for
me. I thanked her for her help and left the store. I found Pam window
shopping and told her that I had completed my shopping. We then left the
mall and headed back to her house.
When we arrived back at her house she told me to strip. I did as
instructed and folded my clothes neatly put them on a nearby chair. My cock
was rising with anticipation as she asked me to show her the panties that I
had bought. As I pulled each pair out I would hold them up for her
inspection and comments. She would make me tell what I found sexy about
each pair before going on to the next one.
She then told me to pick out a pair for her to put on. I selected the
purple thong without hesitation. She then reached up under her skirt and
pulled off the pair of panties that she had been wearing. She smiled and
then proceeded to hang them on my now stiff cock. She then stepped into the
new pair and pulled them up into place. Without saying another word she
slowly raised her dress to her waist so that I could see them on her.
Slowly turning I was captivated by the strip of cloth that disappeared
between the cheeks of her ass. My cock was twitching with anticipation and
I could feel the pre-cum beginning to leak out the tip.
She then pulled the dress off over her head and removed her bra. She took
the panties from my cock and stepped around behind me. She stood very close
behind me and I could feel her breasts brush against my back. She held the
panties up to my face as she whispered in my ear, "would you like to lick my
panties?" I nodded and she turned them inside out and held the crotch to my
mouth. I licked her juices from the cotton panel as she continued
whispering in my ear about how she was going to let me lick her ass and then
make her come with my tongue. My cock just got harder and harder with
anticipation.
Finally she told me to lay on the floor. I stretched out on my back and
looked up at her as she pulled the new pair of panties down her legs and
stepped out of them. She then straddled me with her feet just under my
arms. Then instead of kneeling down she simply squatted over my face. The
cheeks of her ass were spread further and tighter in this position and I had
easy access to her little rosebud. I reached out with my tongue and went to
work. I teased and circle her asshole and tried to push my tongue up inside
the tight little ring. As I was doing this she would tease me by dragging
the thong lightly over my cock. As stupid as it might sound I was really
concentrating on doing the best job I could licking her ass. I knew this
was something that she enjoyed and I was trying not to disappoint her. She
let me continue longer than usual, perhaps because she knew I wouldn't be
doing this again for awhile.
After a few minutes her legs must have tired because she stood up and had
me follow her to her bedroom. My gazed never left her ass as she walked in
front of me. She then laid down on her back and spread her legs. I didn't
need to be told what to do next. The lips of her pussy were slightly parted
as I lowered myself down between her legs. I reached out with my tongue and
drew it the entire length of her wet slit starting at the bottom and ending
with her clit. Once again I licked, sucked and nibbled trying not to
disappoint her. She reached down and held my head as she encouraged my
efforts. It wasn't long before she came and as she did I found myself
closing my eyes as I felt her contractions and swirled her juices around my
mouth savoring the flavor.
After she finished she got up and told me to lay on my back and put my arms
over my head. I began to get nervous as she tied each one to the bedposts.
I knew that she would never hurt me but not being able to move my arms made
me uncomfortable. She told me to relax and reached for the phone. She
spoke softly into the phone asking if someone could come over. I wasn't
surprised to hear the front door open and shut and see Toni enter the
bedroom.
"So this is his last weekend before college?" She asked. Pam nodded and
looked at me, "we're going to give you a treat but first I think you need to
take care of Toni. I'll be back in a couple of minutes." With that she
left the room and Toni stripped out of the jeans she was wearing and
quickly pulled down her panties. She then straddled my face and I once
again started with her tiny little asshole before she directed me to her
pussy. She came once very quickly but I could tell she wanted more as she
stayed on my face. I made her come a second time despite the awkwardness of
having my arms tied to the bedposts.
I still didn't understand why my arms were tied as Pam rejoined us. In her
hand she was carrying black silk scarf. She blindfolded me with the cloth
as she spoke.
"You have learned your lessons well. I believe you now know how to give
pleasure to a woman with your mouth, your tongue and hands. I also believe
you are more respectful of women and the power they hold." I didn't say
anything as I listened to her speak. "There is one other way that you can
give pleasure to a woman," she paused briefly, "and that is with your cock."
I had to remember to breathe as I listened to her, was it really going to
come true? Was I going to get to fuck her? I felt a hand massaging my
balls and my cock as she continued.
"The problem is that Toni and I would like to give you a reward but we want
to make sure that you don't have anything that you can hold over us. I'm
married and even though Toni isn't, it would still be extremely embarrassing
for her if something like that every came out."
"I won't tell anyone." I promised. I couldn't see either of them as I
looked into the blackness of the scarf. "Please, I haven't told anyone
about our sessions so far."
"Our sessions are different." Pam said. "What we are now talking about is
you actually fucking a woman old enough to be your mother. That is the
reason we are tying your arms and blindfolding you. One of us is going to
fuck you, but you won't be able to see who. That way you'll never know
which one of us it was. Now I want you to lay there and enjoy this. I'm
going to put headphones over your ears so you won't be able to hear anything
either. Are these conditions acceptable?"
"Yes." I was surprised that my voice was squeaking.
I felt the headphones go over my ears with soft music playing in them. I
then felt the bed move and someone straddle me. A hand grasped my cock as I
felt the weight of one of them began to come down on me. I felt the tip of
my cock brush soft pubic hair and warm wetness as it was guided to the
entrance. There was a brief moment of hesitation before I thrust up to meet
whoever it was lowering themselves down on my rigid cock.
I can't describe the feeling of having my cock inside of a woman for the
first time. It was warm and wet and gave me a strange feeling of security.
I wanted to reach out and touch her but they had anticipated that and had no
doubt tied my hands for that very reason. I tried to figure out which lady
it was as she moved up and down and around on my cock but I couldn't tell.
She would lean forward and I could tell she was grinding her clit against my
pelvis. I could feel a hand massaging my balls and I was pretty sure
whoever wasn't fucking me was doing that.
I began to meet her movements with thrusts of my own. I got a little
carried away once and my cock popped out. It was quickly put back in place
and I continued enjoying the warm slippery sensation as I slid in and out of
her. It seemed that she was getting wetter and wetter as we went. Despite
the training by Toni I could only last about three or four minutes before I
felt the come welling up inside my balls. Whoever it was knew I was close
and quickened her efforts. A hand gently cupped and kneaded my balls as I
exploded into her. It seemed like I came forever as I fell back exhausted.
I felt the woman get off of me and I noticed the air felt cool on cock.
The headphones were removed and I could her Pam speaking, "as soon as we're
dressed we'll take off your blindfold. I could hear the rustle of their
clothing as they dressed and I could feel the wetness on my cock. After a
moment I felt hands on my head as Toni removed the blindfold. I blinked as
my eyes adjusted to the light in the room. I glanced down at my cock as Pam
untied my arms, it was laying limp on my stomach but was glistening with
juices of one of these beautiful women.
"You may get dressed now," Pam said as my arms were free.
They watched with a smile as I went into the living and put on my clothes.
"I hope you have a good time at college," Toni said.
"We'll still see you around when you come home," Pam added, "and like I
said, maybe someday we'll come see you at school."
I left the house that day no longer a virgin. As much as I thought about
it I was never sure which lady had took my cherry. I was disappointed the
summer was over but I felt in my heart that the sessions I had come to love
were not over entirely. As I drove away I reached down inside my pants and
felt my cock slick with their juices. I held that finger to my nose
savoring the aroma as I drove home that day.
NOTE- This was the last installment of a story I had written over a period
of years. The subject of being dominated, humiliated and taught my an older
woman has fascinated me. This was my first story and I would appreciate any
comments, criticisms or suggestions. I would also appreciate receiving
stories of a similar theme. Thank you
<1st attachment end>
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