Linda
By
Sissie Maid Cuckold
"Hi...my name is Jennifer Dobson; I am 38 years old, 5' 7" tall and 127
pounds. I have long blond hair and get hit on a lot...by both guys and
gals. I was married once to a jerk for 6 years. He lied to me, cheated
on me, ignored me and so I divorced him. I got most all of it and he
lost all of it including the girlfriend he was cheating on me with! I
got the business, a consulting business and began to systematically
replace most of the men with talented women and not only is it now a
fully woman owned business but it is a fully women operated business. I
do have three male employees but you really could not call them men if
you know what I mean!
I have a very successful business and am quite busy. I have taken the
occasional lover from time to time since my divorce but have them for
only one purpose: you got it...sex! Oh, they want more, much more, but I
WONT be trampled on by a man again. I will use them on MY terms. Even my
male employees are humbled and submissive and I am sure calling me "The
Bitch" behind my back. However, I do not really care, its earthier use
them or be used by them and I WONT be used by them!
So it was about a year ago when a sweet young male walked into my
company applying for a job. He was just 22 and fresh out of business
school where he had taken classes on book keeping and accounting. He had
never played sports and owned a 1998 Chevy. He was slight of build and
5' 5" tall. His weight was a mere 122 pounds. His hair was longish and
his hands soft and unmanly, the perfect kind of "man" for my office.
As I spoke with him and saw that he was quite shy and submissive, I
found out he was flat broke and had driven over 300 miles to try to find
a job. He did not even have gas or food money left. He was desperate. He
told me he would take any position I had and at any salary. I could just
feel the power swell inside me, a very vulnerable male at my mercy!
As I spoke to him, I thought back to a woman I had communicated with for
years and got to be very close as phone friends. She had to make a trip
to my city and told me when she would be there. I offered my home to
her but she said that she had "unusual traveling circumstances" and
would just rent a suite at one of the five star hotels. She wanted me to
come and visit her at her suite, which we would then go to dinner and
possibly enjoy some male companions if I was up to it. She was sure
from my tastes I would enjoy these men and it would be all her treat!
Hey, what the heck, I was curious, up for some fun, and certainly wanted
to finally meet her face to face. When the time arrived, I went to her
room and was greeted at the door by a French Maid. I was surprised
because she never had mentioned she had a maid or that she had a maid
who traveled with her. I did know she was married so was quite curious
about her suggestion about some male companionship.
She was more beautiful than I imagined. A drop dead gorgeous brunette
same height and build as myself. We both squealed hugging each other and
smiling from ear to ear when we met. It was just great actually getting
to meet her in person after all the years we had only spoken on the
phone. Liz, my friend, asked me what I drank and when I told her she
immediately instructed her maid to fetch it, the maid curtseyed and
obeyed. I was impressed and asked her about having a maid."
"Oh Jennifer I don't know what I would do without Constance, that's what
I call her, that's not her real name but she's my maid so I figure I
have the right to call her what I want. She is so obedient and
submissive I can tell her to do anything and I do mean anything and she
will obey without hesitation."
"So where do you find a maid like that? I mean that's very unusual from
what I hear to find a maid so submissive and obedient?"
"Well Jenifer, you don't, you have to train them but done right,
training them can be a lot of fun, well at least for the trainer maybe
not so much for the trainee," and she laughed.
I looked at her inquisitively, obviously this was some kind of inside
joke but she just smiled back, raised her eyebrows and said, "I'll fill
you in later. Right now let's have a drink and then go and get some
dinner, I am famished."
Constance brought my drink and we chatted about her trip and reason for
being in town. She apparently had some real estate she had inherited and
was disposing of it. She knew some people around town and would visit
with them in the next few days but right now, she was serious about
eating, we soon found a restaurant and were ordering.
As we ate, I asked her about her husband, Terrance and if he had stayed
home or was away on business. She said, "No he had come with her and I
could meet him later." Just then, she received a phone call and
interrupted the conversation. She took the call and apparently, from the
way she talked she was talking to one of the men she had suggested we
have some fun with. She set up a time for him to meet her back at her
hotel and then hung up.
"Ok Jennifer that was the guys I was telling you about. I have met them
before and they are both studs, and I do mean STUDS! They are real
manly men who know how to satisfy a woman without being a problem later
on. I hope you're up for it because these guys love sex and are nonstop
like the energizer bunny in every way."
I suppose I had a perplexed look on my face, if not I sure felt
perplexed! Liz must have sensed it and said, "Look no worries, if you
decide you don't like them I'll send them home, no problem. You have to
feel comfortable or it won't happen but let me assure you these are fun
guys and you will do well to enjoy them."
"Ok," I said, "but what about Terrance, wont that be an issue?"
Liz got a big smile on her face and said, "Jennifer, Terrance is no
problem, he is no threat, he can't take care of my needs like a real man
can and he knows it and even if he tried to forget I won't let him
forget. You know how you talked about using men or being used by them?"
"Yes"
"Well I have been practicing the same believe from many years now and I
have totally learned how to use them to my advantage. Do you remember
what I said about training a maid?"
"Well sure but..."
"But nothing, Terrance is my maid, he is my sissy maid and my cuckold. I
control everything he does and his only purpose in life is to serve and
please me, so what do you think about that for using them?"
"What? You are not serious! That's was a girl."
Liz laughed, "Well sort of, he has been turned into a girl and more of a
girl than a lot of real girls, but he is still technically a male. Have
you ever heard the statement that, you are either part of the solution
or you are the problem?"
"Well sure but..."
"There are no buts Jennifer. Have you ever seen a husband that was NOT
the problem?"
"Well..."
"I have, Terrance, he was the problem but after training him to be my
maid and cuckold he is now part of the solution and no longer a problem.
His only purpose on this earth now is to serve and please me and believe
me when I tell you he does and he knows it's his only means of happiness
as well."
"Well Ok if you say so but I can't say that I understand it all."
"That's ok, you don't have too, just try and enjoy yourself tonight and
see if you don't agree with me after you have had a chance to see how
this all works, OK, deal?"
"Sure why not."
We went back to the hotel where I kept my eye on Constance, trying to
figure things out and see if I could tell he was really a man in drag. I
finally concluded that if anything he was TOO feminine. Liz let him know
that I knew he was a sissy which caused his face to turn bright red for
a while but it also seemed to calm him at the same time. It was about an
hour before the men got there and when they did, I was surprised to see
they were both Black men. Both very handsome and well muscled very in
shape guys and they both had cute smiles and were very pleasant to be
around. It was not long before I warmed up to them and was getting
interested in more than just looking at them. On top of this, Constance
was scurrying around serving everybody and Liz made no bones about
Constance being her sissy maid cuckold husband. This only seemed to
stimulate the men more and both had obvious hardon's of some
considerable size displayed under their now tightening pants!
The men soon began to pair us off and it was William that choose me. He
sat down beside me, took my hand, and laid it on his hard cock! I almost
came when he did that! The combination of manliness, the sexually
aggressive nature, his good looks and smooth manners coupled with the
humiliation of Constance was all too much for me. I flushed and looked
into his eyes dreamily and submissively like a little school girl, I was
embarrassed by my nature but there was nothing I could do about it! He
has such an effect on me.
Liz said, "Constance, do you like my choice of lovers tonight?"
"Yes Ma'am he's a very good choice Ma'am."
Everybody laughed at this meek sissified husbands words and could not
really believe how submissive and obedient he really was. Of course, our
laughter was not missed or appreciated by him and he turned beat red.
Constance ordered her sissy cuckold to approach her and her lover and
feel her lovers cock through his pants. You could see Constance's hand
shaking as he did as ordered and once he had felt it, she asked him,
"Well Constance, is it any bigger than yours?"
"Oh yes Ma'am, it is much bigger than mine Ma'am and you should find it
very enjoyable indeed Ma'am."
Once again, there was laughter from throughout the room and Constance
got even redder in the face if that was possible!
"Well very good Constance, when he is through you can thank him for
satisfying the sexual needs that I have that you are unable to satisfy,
will you do that Constance?"
"Yes Ma'am, I will thank him for satisfying your sexual needs Ma'am".
"Very good my little pansy, I would not want him to think we didn't
appreciate him."
"Yes Ma'am, I understand Ma'am."
"Ok my little sissy maid go make yourself useful and turn down our beds,
I think our lovers are ready for some close attention. And don't get to
far away we will both be in need of your talented tongue for clean up
duty when they are through."
"Yes Ma'am."
Constance then gave Liz a deep curtsey and scurried off to complete his
duties while the rest of us sat there further sexually stimulated by the
exchange, anxious to get it on and wondering what she meant exactly by
clean up duties with his talented tongue!
Liz explained, "When we are through Constance will come to each of us
and use his tongue to clean up any juices that are the result of our
activities. You will find this most enjoyable and rewarding. Do not
hesitate to take full control over her as she completes this duty. You
men may find yourselves extremely stimulated and in need for further
release which Constance is trained to provide. You Jennifer will do well
to relax and enjoy the cleaning and take control of his head and tell
him what to do for best results. I typically like to relax and think
about what my lover has just done to me while he cleans me to get the
most enjoyment possible, it can be a very rewarding climax if you do it
right."
William and I headed to the bedroom where we first embraced in a deep
kiss and quickly proceeded to removing each other's clothes. His cock
was impressive and I soon was licking and kissing it to his delight. I
have enjoyed men with nice cocks before but none that compared to
William's cock. It must have been 8" long, very thick and rock hard. He
was circumcised which I like and his balls were massive compared to the
other men I have been with. I was quite intrigued by the color contrast
of my lily-white hands wrapped around his dark meat. It simply excited
me is all I can say.
It was not long until I was sucking on his hard Black cock and I could
tell he liked it. He had his hands on the back of my head and was soon
pumping his cock in and out of my mouth. It did not take very long for
him to begin to stiffen, I knew what that meant, and soon loads of thick
semen flooded my mouth. I sucked every drop I could and loved the way he
took control of my head and his flavor. When I was done, I kissed and
licked his cock lovingly and looked up at him to see him smiling proudly
down at me. I smiled back and told him it was my turn to which he very
much agreed. He lifted me, laid me on the bed and began to caress and
kiss me while my hand stayed firmly wrapped around his cock. Soon it
began to swell and get hard and that excited me terribly, it was almost
as if some magical force was spreading my legs open asking him to fuck
me. He sensed my condition and soon was on top of me between my legs. My
dripping wet pussy was open and ready to accept his member, which he
carefully and slowly slid into me. It was larger than I had ever
experienced and it took a little getting used to. The penetration was
such a dominating experience making me feel very womanly and submissive
to him as he took me. Once he was in, he held it still while taking firm
hold of my wrists and stretching me out all while his lips were nibbling
at my neck and ear.
After what seemed like an eternity of this he began to move, pumping his
hard Black cock in and out of my wet swollen pussy slowly with short
strokes at first and as I relaxed he made those strokes longer but still
frustratingly slow. When I mumbled for him to go faster he simply placed
his lips over mine and silenced me as he continued until I was wiggling
and thrashing around trying to get more contact and action. I could feel
his control and power and soon I submitted to his tactics. This was what
he had been waiting for and this triggered him to fuck me hard and deep.
With powerful thrusts that caused his massive balls to slap my ass and
as he fucked me furiously, he stretched my arms out as if I were on a
rack. I knew very well who was in control, who the man was and what I
was and frankly, I loved it, I wanted and needed a real man to pleasure
me. Wimps like Constance had no place between my legs with their cocks.
Men like my x husband were worthless in bed, he knew it and I knew it
but sadly I had not the knowledge or experience to do what Liz had done
to Terrance when I was still married to him. Suddenly Terrance was in my
mind. Seeing the pathetic wimp of a husband sucking about curtseying,
obeying his wife in the most humiliating circumstances. It turned me on
even more having William fucking my brains out while thinking about
having a sissy maid cuckold for a husband to train and torture and
remind him that he was not a real man.
Then it happened, I began to cum. Over and over and over, like never
before. It did not stop and soon I could hear screaming, sexual climax
screaming and I wondered where it was coming from. Was it Liz? How could
she be so loud and open in her sexual expression? Then it began to sound
familiar and closer...it was ME! I was cuming and telling the world how
great, it felt with abandon. I did not care who heard me, no that is
wrong, I wanted everyone to hear me and how great I was being fucked.
What made it so good I wondered? Was it William? He was fantastic; there
was no doubt about that. Was it the sexually charged situation prior to
going to bed with him? No doubt, that contributed to it but then it
dawned on me. The real icing on the cake was Constance, the little wimp
of a husband all sissified, humbled, and degraded. It was seeing a so-
called man put in his real place that was so dammed exciting to me!
William fucked me over and over and over. He did it on my back, on my
side, doggy style, sitting on his lap, bent over a chair and more ways
than I can remember. My pussy was actually getting sore from his massive
hard Black cock but it felt good. Finally, I had to stop. I think he
would have gone on forever or maybe longer! However, I could not and I
convinced him to stop. As I lay their catching my breath I started to
think about what Liz had said about Constance being used for cleanup and
other pleasures after the fucking ws done.
"Constance. Constance come here at once!"
Constance appeared and curtseyed to me. Yes, he actually curtsied to ME!
I loved it. It felt powerful. I smiled at him standing there in his
pretty Black and white French Maids uniform, with its stiff petticoats
nylon encased legs and 5" locked on spike open toes heels. I noticed his
long pink fingernails and the soft submissive obedient look on his
painted face. "Come here Constance and clean me as your Mistress said
you should. I want you to take your time and do a very thorough job, do
you understand Constance?"
"Yes Ma'am, I understand Ma'am."
He crawled on the bed and lowered his face between my legs; I quivered
as I felt the warm wet tongue begin its work. I watched for a moment and
then laid back and began to enjoy it. It was truly wonderful. This was a
husband who had been trained to pleasure a woman with his tongue not a
husband who was doing it just so he could get a blowjob or get his wife
off his back. This sissy knew how to lick, suck and kiss a pussy to
bring it to life. My mind was spinning with all of the excitement this
evening had brought. From the learning of his sissification and
cuckoldry to enjoying a fantastic lover, I was primed. However, the
feeling of laying there after enjoying sex with a real man to then have
a sissified cuckold tenderly suck, kiss, and lick me was extremely
erotic and soon I was ready to climax again. I took the sissies head and
guided it along with words to bring me to a very enjoyable and
satisfying climax unlike any, I had ever experienced. I now understood
what Liz meant when she said it could be extremely satisfying. I also
recognized that part of it was physical and part of it was mental.
Having control over a sissy cuckold was extremely and I do mean
extremely erotic. You cannot imagine the power and sensation you get
from this as a woman until you have experienced it. It truly is using
them for your pleasure and the ultimate in pleasure at that.
As you think about how he is dressed, how he acts and that he is licking
and sucking the cum from a real man out of your pussy with his only
intent in being to make you happy. There is no selfishness on his part,
when you consider this is how real man feels when they sex a woman its
powerful, erotic, satisfying, and wonderful. I was addicted to it
instantly and kept him there servicing me like this until Liz finally
knocked on my door and said that it was time to let Constance do some of
his other duties. I giggled and reluctantly said, "OK."
All of these thoughts flooded my mind as I sat there considering the
wimp in front of me that had just applied for a job and explained how
desperate and vulnerable he was. A wicked thought came into my mind,
"Why not I thought, why not?"
"Joel Lynn Adams. Do you mind if I call you Lynn?"
"Ahhh I usually go by Joel Ms. Dobson."
"Do you want a job Lynn?"
"Yes Ma'am, yes I do."
"Well Lynn, a friend of mine, who is very successful by the way, says
that when someone works for you, you get to choose what you call them,
do you have a problem with that Lynn?"
"Not if it means me getting a job Ms. Dobson."
"Well good Lynn then I guess that means you have a job...but not here I
have another location I want you to work at and I don't have time to go
into all of it at the moment but I will take you for dinner and then we
can talk if you're interested. I think it will meet all of your needs,
you will be provided with housing, clothing allowance and food along
with pay and I am sure you are more than qualified for the position, are
you interested?"
"Yes Ma'am, very interested, I am looking forward to it, thank you
Ma'am, I won't let you down."
"I'm sure you won't Lynn, I'm sure you won't. Now wait in the outer
office until I am finished and we will go and get something to eat."
Lynn did as told until I was ready to leave. We got in my car, went to a
restaurant, and ate then I took him to my house. When we got there, he
asked about his car and belongings and I told him we would worry about
them tomorrow that he would stay with me tonight. He seemed nervous and
uncomfortable so I told him not to worry I would find something for him
to wear and for him to go and take a shower then we would talk about his
new position. He did as I said and when he was in the shower I opened
the door quietly, took all his clothes, and put them in the rubbish.
I found a pair of white panties and pair of women's jeans and a light
pink blouse that I thought would fit him. I also put a pair of white
socks with a pink design on them and a pair of ladies loafers in there
for him and held my breath. Liz and I had talked about Constance many
times since I had first met him but did I have what it took to actually
sissify a man? I would soon find out.
After a while, I heard the shower stop and after what seemed like an
eternity, I heard Lynn call out for me. I went to him and he said he
could not wear the clothes I left for him. I asked why and he said he
just could not.
I said, "Listen Lynn. You will put them on and get out here or you will
be on the street and since I sent your clothes out to be cleaned ,you
will be naked now make up your mind and stop stalling and get dressed
and let's get on with it, is that clear"?
I had no idea if my authoritarian way would work but I hoped it would. A
few minutes later, a very embarrassed and red-faced Lynn emerged.
"I smiled and said, "oh now see you look absolutely wonderful in them,
come, come, turn around and let me see." I complimented him on his new
clothes and told him he actually looked much better in them than the
ones he had been wearing. It was then that I noticed a small bulge in
his crotch. He saw me staring and looked at me and got all embarrassed
again. I sat down and called him to me.
"Look, I am lending you some of my clothes for now but I can't have you
ruining them so we need to fix something." And with that I unsnapped his
pants and pulled them down. His little dick was straining against the
silk panties from the excitement. I lowered them to his disbelief and
shock and told him to spread his legs, which he did without pause. I
reached in, worked his little testicles up into his body cavity, then
twisted his penis, and pulled back between his legs holding it in place
while I got his pretty panties back up to hold his penis where I placed
it, then pulled up his jeans. Once he was all back together I said,
"there now doesn't that look much better, all smooth and not stretching
anything of my clothes out?" I acted as if it was no big deal and just
went on with normal conversation.
I doubt that a female had ever touched him and the experience was both
embarrassing and exciting to him. Then I reached behind him and between
his legs and caressed his half-turned penis. "There now I think you will
find certain advantages to wearing things like they are now. I like the
way these fit you, look on you and feel. Do you mind if I feel you like
this from time to time? It feels nice doesn't it?"
He was flushed and enjoying it. He agreed it was and that he would. I
then focused on his blouse, reached up, and caressed his nipples through
the blouse stating that it was a bit thin and we had better find
something for him to wear under it. I took him by the hand and led him
to my bedroom. For young males that have never been treated like this or
around a woman's bedroom, the events can be extremely stimulating and
they most certainly were to Lynn.
I took him to my dresser, opened my panty drawer, and rummaged around so
he could see all of my pretty panties further stimulating him. Then I
opened my bra drawer and did the same thing. I found a nice soft pink
bra, took it out, and tossed it on the bed. I moved him back to the bed,
unbuttoned his blouse, and took it off. My hands worked his chest and
nipples for a few seconds and then I picked up the bra and put it on
him. He protested feebly and asked why I was putting a bra on him. I
explained to him that you are supposed to wear a bra under a blouse and
continued to put it on.
It was obvious that he was sexually charged I could have done anything
to him. He was still a virgin and had never had sex or sexual contact
with a woman. Once the bra and blouse were on, I moved him in front of a
mirror and let him see how le looked. Other than the face, it could have
been a girl in the mirror and this seemed to excite him even more. Oh,
he did not have a perfect hourglass figure or big boobs but the clothes
made him look like, well, a country girl in jeans or something.
I got behind him, reached over his right shoulder down inside his blouse
and bra, and played with his left nipple. He was paralyzed. The sexual
stimulation was something he had never experienced and he was at a loss
as how to deal with it except to submit to it. Boys are usually the
aggressors and in control but the tables had been flipped on this young
male and he was being treated like a girl and finding it quite
enjoyable. Had he known what was really going on, what was truly
happening to him, he may have resisted but at this point, he was
clueless.
"I love the way you look in these clothes Linda, it makes me hot for
you. Would you like it if we took this further...sexually I mean?"
"Oh yes Ms. Dobson, I would like that very, very much," he said in a
trance like voice. He paid no attention to the fact that I had just
addressed him as Linda.
"Good, because I would like to, but you understand there has to be
rules, I have to protect myself, you being a man and me being a woman
don't you?"
"Yes, I understand".
"Good Linda, as long as you understand and as long as you do what I say
then we can have lots fun but if you don't obey me then the fun stops,
is that clear Linda?"
"Yes Ms. Dobson."
"Very good. Ok now the first rule is you must remain tucked liked you
are now whenever you have panties on, is that clear?"
"Yes Ms. Dobson."
"And you will allow me to touch or caress you any time I want wont you?"
"Oh yes Ms. Dobson anytime, I like that rule Ms. Dobson."
"I'm glad Linda because I am afraid I won't be able to resist touching
and caressing you Linda, you are sooo attractive." At this point I moved
my other hand down to his ass and then between his legs caressing the
head of his penis extracting moans of pleasure from him. He bent forward
slightly to provide better access to me reminding me of how a female
would respond in the same situation. It was odd for a male to respond
this way because their natural response is to bend backward for deeper
penetration and more exposure. However, his tail was tucked and he was
responding properly because of that.
"Ok Linda here is the next rule. Whenever I tell you to lay across my
lap you will do it and put your hands behind you so I can hold them
while I play with you. Do you understand that rule Linda?"
"Yes Ms. Dobson, I understand."
"Ok then let's try it right now."
I moved to the bed, sat on it and he lay across my lap. He put his hands
behind his back just like he was supposed to and I took hold of them. I
spread his legs a bit and rubbed his penis head slow and steady. As I
did, I forced his hands a little further up behind him until he winced.
I said, "Now I am sure you understand Linda that to get real pleasure
you must experience a little pain, don't you?"
Just like a robot he said, "Yes Ms. Dobson, I understand."
"Good Linda but I am not sure you like this or wearing the pretty
clothes you have on. Do you like it and them?"
"Oh Yes Ms. Dobson, I like it a lot."
"Well Linda I don't know. I like to know somebody likes something. So if
you really do tell me what you like and why or if not I will stop
caressing you like this because then I know you don't enjoy it."
"Oh, ah I do like it Ms. Dobson, I like being like this and wearing what
I am wearing."
I stopped caressing him but held his wrists tight. "Oh Linda that won't
do, that won't do at all. I want to hear the details, why you like it,
what is being done and what you are wearing and why and how you want
more of it, real details and lots of it or its simply is no fun for me."
"Oh I see what you mean Ok, I love wearing these ladies jeans they fit
so nice and make me feel very strange and good and I love wearing your
panties Ms. Dobson, I was embarrassed at first but they feel so cool and
neat. And I love the way you tucked me and told me to be tucked like
that its really great the way it makes me feel and how you can rub me
like you are right now..."
I continued to caress him though his jeans bringing him very close but
not over the top. I held his wrists and he was very submissive doing
whatever I told him to do or say. After he went on and on about how much
he liked everything and how good it made him feel I took over.
"Ok Linda we need to talk about your new position. I want you to be my
houseboy. You will clean, cook, do laundry, and take care of my house.
You will take care of my personal needs; like bathing me, rubbing lotion
on me, doing my nails and hair and such, very intimate personal things
Linda. In addition, I want you to sleep in my bed, of course, you will
have rules to follow and you will have to earn rights but I think it
would be nice. You will dress how I say and do what I tell you. Are you
interested in that?"
Linda thought a moment and tried to speak but his mouth was dry and he
was exhausted from being kept on the brink of a climax for over an hour!
"Really, you will let me sleep with you?"
Is all he could manage to say or think about.
"Yes Linda but only if you follow ALL of the rules, do you understand?"
"Oh yes Ms. Dobson, I do understand I really do and I will obey."
Linda had only dreamed about girls and to be with an older woman who was
experienced and beautiful like Ms. Dobson was, well it was still a dream
and he could not believe his good luck.
"Ok Linda, let's get you assigned to some tasks, remember you have to
earn privileges around here."
I let go of Linda's hands and helped him to his feet. He was quite
wobbly and needed to clear his head. I took him to the kitchen and told
him I wanted him to sweep the floor and then scrub it on his hands and
knees. That if he had any problem he could come to me and I would help
him. I retired to the living room and the TV set. When he was finished,
he came to me and informed he was done. I got up, inspected his work
pointing out any deficiencies, and had him correct them. Then I went
back to my chair and had him sit at my feet where I taught him to
massage them. I liked the feeling of having him sit on the floor at my
feet. It was both stimulating and relaxing. I felt power, real power
over a male. I felt like I could make him do anything.
After an hour of him massaging my feet, I told him it was time for bed.
When we got in the bedroom, I could tell he was very excited. I turned
to him and said, "Now Linda if you do as you are told and obey me
completely you will earn rewards. So far, today you have done quite
well, some improvements are needed but since it is your first day, I am
making allowances and giving rewards liberally. That will not be the
case from here on. You will be expected to obey perfectly and show
enthusiasm in your duties or no rewards will be given and in fact if you
do poorly enough you will be punished, is that perfectly clear Linda?"
"Yes Ms. Dobson, thank you Ms. Dobson."
"Very well then Linda, we will change into our night wear. Since you
have none of your own I will share some of mine with you and for being
such a good girl I will reward you for wearing what I tell you to wear
with your first climax from a woman. Are you ready to obey me?"
I watched his face closely as I told him he was a good "girl" he did not
show any difference. I concluded that either he did not actually hear
what I was saying because he was focused on getting to cum or that he
was accepting whatever I did or said without question. I would explore
this further later but for now, there was no apparent disagreement with
my words, which was good.
I told him that I would undress and dress him for bed first and then he
would do the same to me. I took off his blouse, pants and shoes. I then
put a silky short nightgown on him. I noticed him shiver as the filmy
material brushed across his skin. It as a shiver of delight and so I
acknowledged it, "I think you will enjoy the feel of this material. It
feels very sexy and will help us enjoy your climax in a few moments, do
you like the way it feels?"
"Yesss Ms. Dobson, it feels very nice."
"And it looks very nice on you, do you like the way it looks Linda?"
This question seemed to embarrass him some but he replied shyly, "Yes,
Ms. Dobson it looks nice."
"Good, I am glad you like how it feels and looks because you will wear
items like this or similar to bed every night from now on Linda to
please me. Remember by accepting the job I offered you your duty is to
please and serve me, to agree with what I think and to even accept what
I think as your own thoughts. When you can do that you will be on your
way to becoming exactly what I want and most importantly need. Do you
understand what I am saying Linda?"
"Yes Ms. Dobson I understand what you are saying and I will do my best
to be what you want me to be and think how you want me to think. I like
what has happened so far very much. This is the most exciting and nicest
thing that has ever happened to me in my whole life!"
"I am Glad Linda. Now you must learn to undress and dress me. First, you
are NOT to touch my body as you remove or put clothes on me. A good
maid never touches her Mistress unless she is told to touch her and then
only as directed. You will start with my shoes and then work to my top
and then bottom taking things off in layers and folding, hanging or
placing them in the laundry as appropriate. Are we clear on this Linda?"
'Yes Ma'am very clear."
"Very well, begin."
Linda carefully removed my shoes and placed them in my shoe rack as
gently as I have ever seen anyone handle shoes. This brought a smile to
my lips. He then unbuttoned my blouse his hands being ever so close to
my breast I could see his fingers tremble. This was likely the closest
he had ever been to a woman's breast since he was nursing as a baby! He
took my pants down and I heard him gasp as his face was close to my
pussy. He adverted his eyes I suppose fearing that I would take him
staring as a lack of respect. This too brought a smile to my lips. He
then moved to unhook my bra and when my breasts cleared the cups, his
mouth opened and a second gasp emerged. I placed my hands under my
breasts and lifted them, massaging them in front of him, smiling and
saying, "Linda, some day you may be able to earn the right to caress
them for me, but for now you have a lot to learn and mileposts to cross.
Do you like them?"
"Oh yes Ms. Dobson, they are so beautiful, thank you for allowing me to
look at them. I will do whatever you want to be able to touch them. I
love them so much Ma'am, they are just gorgeous Ma'am."
"Ok Linda, we will work on that reward but for now please put my night
gown on me."
"Yes Ma'am." He carefully put it over my head, pulled out the crumpled
up hem, and smoothed it. He then took a step back and his eyes got wide.
My nipples were hard and erect and they stood out in the nightgown
drawing his attention. My beauty mesmerized him and I giggled inside at
how much power I held over this boy.
I sat on the edge of the bed and told him to lie over my lap. I took his
hands, pulled them up behind him, and fastened a padded cuff set to his
wrists to keep them there. I then placed a padded collar around his neck
and fastened the cuffs to the back of the collar to prevent him from
getting his hands under his feet and in front of him.
I now had easy access to his panties and his little penis tucked back
between his legs with a half turn making the head of it fully exposed.
Caressing his little dick through his panties was far more stimulating
that though the jeans earlier. I felt it get hard instantly and knew I
would have to be careful to take my time and make it last. As I caressed
him, I spoke to him.
"Tomorrow Linda I want you to do several things while I am at work. I am
only going to tell them to you once and I want you to repeat them back
to me after I tell you each one. If you complete them all without any
mistakes and each task is done well...I will allow you to suckle my
breasts tomorrow night before going to bed. Is that a deal Linda?"
"Oh yes Ma'am, thank you Ma'am."
"Don't thank me until you hear what your tasks are and complete them
because any mistakes and you only get to look once again."
"Yes Ma'am."
"Ok the first thing is that I dislike body hair and you have body hair.
In the bathroom closet, you will find a bottle of Nair, a hair remover.
I want all the hair below your eyebrows removed. Front and back. Read
the directions, use it, and be free of hair when I get home tomorrow.
Then I want you dressed, I will lay out your clothes for you. Remember
to tuck yourself and to help you stay tucked better I am going to lay
out a body briefer for you to wear. I expect you to have it on over your
bra and panties and under your other clothes when I arrive home. You can
put your bra on by hooking it in the front and then turning it around
and pulling it up on your shoulders. Eventually we will teach you how to
fasten and unfasten your bra behind you but for now you can do it that
way.
I have a book on nails. How to do manicures and paint nails. I will lay
that out. I want you to study it so you can take care of my nails, that
will be one of your tasks. I will also put some polish and remover out
for you to use for practice. You will practice on your nails and that
way I can see what progress you have made. You will not be allowed to do
mine until you are competent.
You will also make the bed and vacuum the entire house. I am going to
train you to be my maid Linda, you will learn to be a perfect ladies
maid before I am done with you." As I got to this part, I began to
speed up caressing his penis and knew he was close. I began to taunt him
and put images in his head hat he would relate to his sexual pleasure
causing him to associate them with his release and making him want to
repeat them.
"Linda, I like you calling a girl's name and I like to call you a girl.
Do you like being called a girls name and a girl Linda?" He did not
answer right away so I stopped caressing him. He bucked a little trying
to get the feeling going again but my hand was moved. I asked him again
and he replied, "Yes Ms. Dobson, I like having a girl's name and being
called a girl."
"Very good Linda, your learning. Remember you are to like what I like,
want what I want, think what I think and you will get rewards. Do you
like wearing girls clothes Linda?"
There was no hesitation this time. He was close and wanted no delays.
"Yes I love wearing girls clothes Ms. Dobson." I am sure he could
justify these comments by telling himself he was pretending or something
but little did he know this would become a routine and eventually it
would ring very true in his mind.
"I told you I was going to train you as my maid Linda, do you want to
become my trained maid and take care of me intimately?"
"Yes Ms. Dobson I want to be your trained maid."
"What sex is a maid Linda?"
"A female I guess."
"Yes Linda a maid is a girl and girls wear dresses and other frilly
clothes. They wear a stiff full petticoat under a maids uniform. They
wear a cap, an apron, five inch heels, nylons, and a corset. If you're
going to be my maid you will need to wear all of these things as well as
make up and nail polish, does that sound like something you can do
Linda?"
"yeesss Msss Dobson." He was so very near coming I had to really slow to
almost a stop and reduce the pressure on his little dick or he would
burst.
"Do you want to cum Linda or should I stop and let you go to sleep?"
"Oh no please Ms. Dobson I want to cum I NEED to cum, you promised me
Ms. Dobson, please let me cum please?"
"Well OK if you insist but for me to make that happen I want you to tell
me what you will wear as my maid and why you will want to wear it and
how it will look on you."
"Yes, Ok I will just rub me please."
"Tell me first then I will rub you Linda."
"I will wear my panties and bra and a petticoat like you said that is
stiff and holds out my skirt. I will wear a very pretty maid's uniform
like you see them wear in the movies and high heels. I will wear a
maid's cap and an apron and make up and nylons and a corset so my waist
is small like a real girls waist. I will be your maid and be very happy
to be so."
He was so close now, "Will I have to force you to wear the dress or will
you gladly do it for me?"
"I I I will Gladly doooo it forrrr you Ma'am."
"What if I decide that you will only wear dresses and skirts from now on
forever and I never let you dress like a boy or even wear girls pants
again what would you say to that Linda?"
"IIIIIII wooould sayyyy OKKKKK I would wear them like you want".
"Good then starting tomorrow you will wear only dresses from now on
Linda and I will make you my sissy maid!"
At that, he burst shooting semen all over his ass. His panties were wet
but I continued to caress him easing up but keeping him stimulated so he
could not reset his sexual clock. I wanted him to go to sleep feeling
the relief but still excited and thinking about what all he agreed to.
Once he had completely expelled his load and I had him getting semi hard
again, I had him stand up and I changed his panties so he had on dry
ones to sleep in. Then I helped him into bed where he slept next to me
hands secured behind his back.
He had a somewhat restless night, I suppose due to his hands confined
behind him. I did reach down under his nightgown at one point and rubbed
him a bit. In the morning, I allowed his hands to go free, took my
shower and had him dress me. I think seeing my pussy was a real exciting
thing for him. I doubt he had ever seen one before. He was very careful
not to touch me and he was breathing very shallow and hard as he put my
bra on. Once he had it on I turned to him and said, "Now remember your
reward if you do what you are supposed to today." Then I cupped my bra
and shook my breast a bit.
I had ordered him to Nair himself so he was going to be awhile before he
got dressed but I began to lay out his clothes for the day. I started
with a lacey pink matching bra and panty set, followed by a body briefer
that I held up and explained to him. It was one with a tight waist and a
padded bra, hips and derriere so I thought it would be perfect. I
explained how it would hold him in place better than just panties and
that he should remember that no bulges were permitted.
I got out a pair of nylons and explained to him how to put them on and a
garter belt and went over that with him. Then I got out a white slip and
a yellow summer dress. The dress was yellow but had pink and blue
flowers on it. I could see by his eyes this was becoming a little
overwhelming for him.
"Are you Ok with all of these pretty thinks Linda?"
"Ahh I guess so."
"Well you look a little confused dear."
"It's just..."
"It's just what Linda?"
"It's just that I thought maybe you were just teasing me about wearing a
dress."
"Oh no Linda, I would not tease you about a thing like that. I want you
to wear dresses for me; I think you will look very pretty in a dress.
You looked so cute and sexy in the night gown last night, I just can't
wait until your all prettied up and filling your promise about being my
sissy maid."
"Whhhhat do you mean sissy maid?"
"Oh well no we didn't talk about being a sissy maid did we? Well you see
Linda when a male like you wears girl's clothes they are what is called
a sissy. Once you have, worn girls clothes you cannot really ever be a
man again and well actually I don think you were ever really, what we
would call a real man anyway. Therefore, since you have worn girls
clothes and have a girl's name and are going to be my maid you will
truly be a real sissy and therefore a sissy maid. You will learn to
quickly like it, all the boys who try it do. So this is what you will
wear if you want the rewards I promised you or you can get out right now
and leave the pretty clothes here. What will it be Linda?"
"But Ms. Dobson, I am a boy and yes I liked what we did yesterday and
last night, in fact I liked it a lot but about wearing dresses ALL the
time, it's just..."
"Listen you pathetic excuse for a man. Did I not buy you dinner last
night and let you wear my clothes and give you the best sex you ever
had?"
"Yes."
"I thought you said you wanted to work for me that you wanted to be able
to have sex with me, that you would wear what I told you to wear? Were
you lying?"
"No".
"Well then you better think hard and fast about what you're going to do
because you only have two choices and one minute to decide. You can take
off what you are wearing and walk out the door right now and live the
pathetic life you have been living, no job, no home, no sex and no
prospects or you can do what you were told and wear what you were told
and enjoy the best of everything. You know what I don't even care what
you do and I am not going to wait around to see, I'm leaving and I will
see when I return tonight so make up your mind. Bye."
As I walked out, I noticed his eyes welling up with tears. I really did
not know what he would do. I do know I liked what I had done and would
do it to some other male if this one did not work out!
I stewed over him the rest of the day and went from convincing myself
that he would then that he would not. It was driving me crazy and
distracting me from my work...not a good thing. I convinced myself he
would then that he would not at least a dozen times each. Then I
convinced myself that I did not care, ten more times! However, the truth
was, I did care, I wanted him to be my pet sissy maid cuckold, I loved
the power, the fun, the excitement and I wanted it to happen.
When I parked my car and opened the front door, I had no idea what I
would find but there he was. Dressed in the yellow dress and wearing the
yellow 4" heels I left out for him. His nails were painted pink and he
looked submissive and defeated. He looked at me for a moment and then
his eyes welled with tears and he broke out sobbing and fell to my feet
kissing them and saying he was sorry.
I took it all in and then told him to stand up. He did and I told him to
turn for me and then to turn faster and make his skirt fly out, he did.
I pulled him to me, kissed him on the head, and said, "I am very proud
of you Linda, you make a very pretty girl and you will make an excellent
maid. I am glad you recognize you are a sissy and not a real man and
that you like wearing pretty things. Now I want a bath and I want you
to run my bath water and then I am going to allow you to wash my body
because you have made me happy and proud."
He stopped crying and wiped his tears, his eyes got big, and he smiled
and said, "Really Ms. Dobson, you are going to let me wash your body? Oh
thank you Ms. Dobson."
He ran the water and bathed me as I commanded him to do so. He was very
tender and attentive trying to do a perfect job. I could see the
contentment on his face from having such a close association with me.
When I got out, he toweled me dry carefully patting and not rubbing as
he dried my body. He then helped me dress in my nightwear.
"Very good Linda, you did an excellent job. I am going to give you
another treat for being such a good sissy girl. When you lay across my
lap tonight and I rub you between your legs we are going to watch a porn
video."
His eyes got big but he said nothing. We went to the bedroom and I put
on a short video featuring a sissy being humiliated by his Mistress. I
set it on loop so it would continue to play while he lay across my lap
and had his hands fastened behind him first and then to his collar.
"Linda, I want you to learn what I like and don't like and to train your
mind to accept those things for yourself. What that means is that if I
like something so will you and if I do not like something you will not
either. As my sissy maid you will need to learn to think like me so you
can anticipate what I want, need or like. So as we watch videos I will
tell you what I like and you will then repeat it saying it as if you
liked it. This will help you to learn and be more useful to me, do you
understand this?"
"Yes Ma'am, I understand."
"Good girl, now let's watch."
As we did, I played with him stimulating him but not allowing him to
climax. The Woman forced her sissy to dress ultra feminine and then to
drive to a gas station and pump gas. Others noticed him and she forced
him to park down the street and walk several block home in 5" heels and
a short skirt where he drew additional attention. I expressed how I
liked the way she emasculated him, humiliated him to show how weak and
inferior he was and embarrassed him by dressing him in such high heels
and a short skirt and exposing him to others. I then had Linda tell me
he liked the same thing. I could tell it excited him to have to say
those things so I had him repeat it several times. Then I said, "Well if
you like what is being done to this little sissy so much I want you to
beg me to do it to you."
He hesitated, the reality hitting him of what he was about to do so I
stopped massaging him, which he knew what that meant, so he started to
beg me to do the things that the video Mistress had done to her sissy.
As he talked, I increased the speed and the pressure and he came as he
was just finishing begging me to do those things to him.
For the next several nights we viewed different videos, sometimes 3 or 4
night and had worked up to sissies serving Black Masters being fucked
and sucking big Black cocks. I would give him his reward as he begged to
be the sissy in the video and have the things done to him. What he did
not realize is that while it was all fantasy, at least at the moment, he
was conditioning himself to understand that wanting these things and
pretending he was the sissy in the video brought him immense sexual
pleasure. He had technically enslaved himself to these desires without
even knowing what was happening.
The next day when I got home from work I told him I had a special treat
for him that night but that he had to take the rubbish out for
collection the next AM. His eyes got big, this would be the first time
he was in public dressed as a sissy but it was time. I said, "Hey you
begged me to send you to the gas station and make you pump gas like the
sissy in the video, were you lying to me?"
"No, No Ma'am I wasn't lying but..."
"No buts about it missy, you take the rubbish out and by the way there
is a bag in there that has your clothes and wallet in it. It is time for
you to get rid of your old self and submit to being my sissy. You need
to understand that bag is there and agree to get rid of it. I want you
to take it out so I know what your commitment is. And I want you to
practice your sissy walk, you know, short steps a wiggle and hands limp
wristed on your way to and back from the curb. If you go to fast you
will make several extra trips."
His face flushed and I could tell his breathing was becoming erratic.
However, he did what I wanted. When he came back in I said, "I just love
how much of a pansy you are that you obeyed me by throwing away all of
your male identity and past, it shows how pussy whipped you are and
there is no manliness left in you."
He looked at me and swallowed hard and said, "I just love the way you
made me throw away my last reminders of being a man and have turned me
into a totally pussy whipped wimp who completely obeys you."
I smiled a huge smile and said, "Perfect, you are becoming a perfect
sissy Linda." Knowing he was broken as a man and could not turn back
now. I felt myself get wet from the power that I had just experienced. I
love it!
That night I put on a Black cock sissy trainer video that showed white
sissies being used and abused by Black cocks. Sucking them, getting cum
shot on their faces and asses and fucked into submission. As it was
playing, he was begging to be a sissy as they were and treated as they
were. At one point, a sissy was on his knees with his hands bound behind
him sucking a big Black cock. It was a very sexy scene and I knew Linda
liked it. I paused the video and asked him if he really liked it and
wanted to do it and thinking it was all fantasy I am sure he said he
did. I picked up my cell and called William, the Black Man I had fucked
and sucked before and asked him how close he was. I had already arranged
for him to come over that night and he said he was about 2 minutes away.
Linda heard me talking and said, "What...what are you going to do?"
"Oh sweetie I am not going to do anything but watch, it's you that's
going to do something. That was William, the Black man I have talked
about in the past; well he'll be here in just a few moment to make your
dream come true."
"Whaa, Whaa, Whaat dream is that Ma'am?"
"Your dream of sucking a Black cock like the sissies in the video. You
have been begging me for a week to suck a big Black cock and I think
it's time I grant your wish."
"BU, BU, BU, BUT I thought it was just a fantasy."
"Well maybe it was when you started out but I want to see you suck a Big
Black cock and you do want to please me don't you?"
"Yes but..."
"There are no butt's when it comes to pleasing me Linda, besides you
know you really do want to experience Black cocks and I assure you that
you will really learn to love them. We will start you out slow and easy
by learning to suck them for now but eventually you will leaner to take
them in your sweet little tight pussy ass as well. Now don't fear you
can see how much all those little white sissies love serving Black
cocks, there is no mistaking how much they want them or how much fun
they are having with them. So just be a good little girl and do exactly
what I say and you will soon be an expert cock sucker! And then later we
will let you cum if you do a good job."
Linda was so wound up and the sexual stimulus was so great his mind was
spinning. It was not long before William arrived. "Hi darling, glad you
come over and help out with this little sissies training."
"Hey I'm glad to help train any white boy to be a girl. They are so much
more useful that way than when they are trying to be men!"
"I could not agree more. As you can see this one is not even close to
being a man and we have been watching Black cock sissy training videos
and he has been begging me to let him suck a Black cock. And of course I
thought of you and your wonderful Black cock and wanted to share it with
him."
I helped Linda position herself in front of William and then took out
his cock and stroked it next to her face. Her hands being secured behind
her I thought I should help. I pushed her head close and rubbed his
growing cock on her face and pushed the pee opening to her lips and told
her to kiss it!
Linda was very nervous but did as I told her to do. Then I said, "Tell
Mr. William here what you have been telling me about sucking Black
cocks."
Linda looked up wide-eyed into his eyes and then started to tell him how
much she wanted to suck Black cocks like the sissies in the videos did.
He smiled down at her and asked her many question all set to humiliate
and humble the pansy kneeling in front of him. He then told her to beg
him, which Linda did without hesitation. "Open your mouth bitch and
suck it good and don't you dare spill a drop or I'll beat your lily
white sissy ass."
Linda did what she was told and started to take it in. I guided her on
how to suck, tease, lick and kiss his manly cock. After about ten
minutes, I could tell William wanted to cum and I prepared Linda for his
load. William took her head and fucked her mouth like it was a pussy,
shooting a large load of hot cum into her throat. She gagged a bit and
then I heard sucking sounds as she swallowed the hot load of jisim
forever making her a pansy cocksucker. There has to be a moment when
this happens that sends impulses through the little sissy's brain
notifying every part of his body that any chances of him ever being
manly again are gone, that he has crossed over to the submissive
feminine side and there is no way back. It seems you can tell this
moment by watching the sissy submit and accept what he now is and suck
willingly, more willingly than before the cum entered his throat. It is
as though he now knows and fully accepts his position and there will be
no more attempts to stall or show disgust. He has sucked the Masterful
Black cock and there is no going back!
He did perfect especially for his first cock and swallowed all of it. I
had him thank Mr. William and then get back over my lap. He was wound
tight and ready to burst but I teased him. Then I had Linda beg Mr.
William to allow her to suck him again. She did so and William
positioned himself so he could stick his hard cock in her mouth while
she lay over my lap. I played the video and talked to her telling her
how much I liked seeing her with a Black cock in her mouth. How she was
as good a cocksucker as the sissies in the video and how she looked just
like them. As soon as William shot his second load in her mouth, I
brought her to a climax. It was the best one she ever had and it was
done while she was sucking a Black cock and dressed like a sissy. I knew
this would have a powerful effect on her mind, that she would wish to
repeat it over and over. I then pulled William's cock from her perfectly
sealed lips and milked out the last of his semen on my sissy's face, in
her nose and eyes coating her with the scent of a real man. It was a
scent that Linda would be unable to ignore, a scent that would permeate
his weak mind and capture his feelings through the power or a real man's
pheromones that had just taken control of him.
"Kiss the man's cock little girl, yes kiss it nicely for giving you such
a wonderful reward. You looked just like the sissies in the videos, you
looked so pretty with a huge Black cock in your lips and I loved the way
you suckled on it. Now thank the man for allowing you to suck his cock
off and to swallow his semen, thank him nicely Linda."
I continued to caress his little dickette as he said, "William Sir,
thank so much for allowing me to suck your manly cock, It tasted so good
and was such a pleasure to suck. Your taste is marvelous and I enjoyed
it so much, thank you Sir, thank you."
"Well your very welcome little sissy girl. You did well for your first
time, I will have to teach you how to deep throat it though. Now let me
tell you girl, I will expect you to do as good or better in the future
when I come by or bring some of my brothers by to have you suck them. It
is good you showed me respect after being allowed to suck me off like
that; I would have been offended had you not. I think you should know
that Ms. Dobson wants me to train you further in the ways of pleasing a
Black Man so in two weeks I will be breaking in your sweat little pussy
ass. I tell you that so you can begin to train it to take a big Black
cock like mine but that is up to you. Either way my hard cock is going
in and the tighter it is the better I like it so it's up to you pussy
boy if you prepare or not."
"Linda, I think you need to ask Mr. William to fuck your pussy ass in
two weeks and thank him for offering to do so and tell him how you plan
to get ready for his fucking you."
"Yessss, yesss, yes Ma'am. Sir, Mr. William, would you please come back
in two weeks and fuck my sissy pussy ass, I would love it if you would
Sir. I will work hard at getting it ready for you Sir and make sure I am
ready to enjoy being fucked by you Sir."
"What a fucking pansy white boy you are Linda. You have no spine at all,
you surely are a pussy pansy wimp. It will be my pleasure to fuck your
sissy brains out and deposit my loads in your pussy ass and watch you
beg and squirm and moan like a little girl as I fuck you. You best do
exactly what Ms. Dobson tells you to do and be ready because if you
don't or aren't I will beat your ass to a pulp and then drop you off in
the middle of the Black part of town in just your panties, bra and
heels. You got that white boy?"
"Ye, ye, yes Sir Mr. Williams Sir, I will Sir, I will do as you want
Sir."
Both Jennifer and William laughed as Ms. Dobson stroked the pansy and
brought him to a third climax. Linda was defeated, humiliated and
humbled. He felt totally owned, controlled, and submissive. He could
smell the man scent left on his face and taste the cum that had entered
his mouth and gone down his throat. He felt different. He felt that he
had done what he was supposed to, that he had accomplished what was
expected of him and in some way, he was proud of that. Proud that he had
sucked a Black cock off and swallowed the cum, almost like he wanted to
scream out that he had done it and tell the world. Yet he also knew it
had changed him. He felt his dickette get smaller and his marble sized
testicles shrink even more. He felt more feminine.
After William left I put Linda over my lap once more and told him how
much I liked the way William treated and used him. How much of a wimp it
made him and how I enjoyed thinking about what was going to happen in
two weeks. I told Linda to beg me to make that happen and to tell me how
good it would feel. Linda being totally subjugated at this point did as
told and as she got deep into begging to have it done, I took the sissy
over the top and had him cum for the fourth time that night, cumming
while thinking about and begging for a Black Man to fuck his virgin
sissy ass. This would have excellent mental effects on my pussy whipped
sissy boy.
The pansy was very overwhelmed by all the power around him and was not
ready to say no or challenge anything being said or done to him. I was
amazed at how submissive he actually was. I found it hard to believe any
male would allow such total degradation of himself without even a
whimper. I kept him over my lap and asked him if he understood how we
would get his pussy ass ready for Williams cock.
"Yes Ma'am, I think you will use butt plugs and dildos to stretch me, is
that right Ma'am?"
"Very good Linda, I see you have been paying close attention to the
videos we have been watching. I want you to get up, cleaned up, and get
dressed while I dress and were going to take a ride to an adult toy
store and get you what you need. You don't have any time to lose if
you're going to be taking Williams big cock in your pussy ass in two
weeks!"
We got ready and nervous as he was he got in the passenger side of my
car and I drove across town to an adult toy store. I was surprised to
see a woman running the cash register. I had only been in one or two of
these previously and it had been a long time ago. It had a lot more
DVD's and fewer magazines than what I remembered and a huge selection of
clothes and toys, especially phallus type toys!
I figured, "what the hell" and approached the girl behind the counter
with sissy boy in tow. It was obvious he was a sissy, just light makeup
and no wig but his hair was longish but still styled more like a man's
cut than a woman's. She saw him next to me and smiled a knowing smile.
"Hi, we need some help. My Black boyfriend just made my sissy here suck
his cock tonight. The sissy did a good job and swallowed it all." The
girl looked at him, raised her eyebrows, and nodded her head in
approval.
"And in fact he actually sucked him off twice and thanked him for the
opportunity. But My Black lover wants to fuck this sissy's pussy ass in
two weeks and he's still a virgin, what do you suggest to get him
ready?"
"Ok, well, is your lover well hung?"
"Oh yes he's got a very nice cock, both long and thick."
"Ok so we'll need to stretch you sissy out pretty good or it's going to
hurt him. Do you w