Jerry free porn video

My name is Jerry, and I'm a 42 year old and own a successful architecture
firm, employing over 50 people. I have married for 19 years, most of which
have been happy.

I do have an eye for the ladies, and Mary, my wife couldn't help but
notice. She is very jealous and keeps a close eye on me.

We are still having sex but it's been getting a little routine. For the
last year and a half I have had a wonderfully discrete affair with Marsha,
who has added a lot more interest to my sex life. I had been extremely
careful not to deviate from my normal routines or leave any clues about
Marsha.

In some way Mary found out about Marsha and confronted me. I tried to deny
it but nothing worked. She threatened me with divorce, which would have
ruined me financially. I called Marsha and told her we had to stop meeting
until this blews over. Marsha became angry with me for not being discrete
enough.

Now I had the two women in my life upset with me, and I just didn't know
what to do. I had a rough couple weeks, until one day Mary sat down with
me and said she had an alternative to divorce.

That certainly caught my interest and I asked what she had in mind. She
handed me a device made of plastic and metal and a small brass lock. "What
is this?" I asked.

"It is a CBT-2000 chastity device," Mary explained, "You will wear it and I
will keep the key. You will be released when I choose to and may climax
only if I permit you to. Otherwise you will be celibate and increasingly
horny."

"How long will I have to wear it?" I asked.

"For the rest of your life," Mary explained, "Your climaxes will be
completely under my control – either accept that or I'll ruin you with a
divorce."

I was really backed into a corner – I certainly could never agree to
surrender my orgasm to Mary, but I couldn't imagine being beaten to the
ground if she divorced me.

"You don't like this alternative," asked Mary, "do you?"

"No, I don't," I said, "but you seem to have me trapped."

"Ok, how about just trying it out?" asked Mary. If it works out ok we'll
continue, but it can come off."

Agreeing to a trial seemed much better that agreeing for life, so I
consented.

She told me undress and she would show me how it works. I undressed and
she took apart the CBT. She attempted to put it on me but I became
aroused, preventing her.

"Does the thought of being in chastity arouse you?" she asked.

"No!" I replied, "but your handling me is arousing."

"I'll have to make you climax," she said, and began stroking me.

I was fully erect and just wanting to cum. She continued to stroke me and
soon I climaxed. She had me shoot into a tissue, and then discarded it.

When my erection subsided she was able to finish putting the CBT on me.

"Does that feel ok?" she asked, "we need to make sure it doesn't pinch your
sensitive parts."

"It's ok," I said.

"Good," she said, "Let's see how it works out." She put the key to the
lock on a chain and hung it around her neck. "Now I am your keyholder,"
she said.

The idea was very kinky, but scary as well. I was glad it was just a
trial.

I wore the CBT to bed and found that is wasn't difficult to become
accustomed to.

I awoke the next morning in pain. I normally awoke with an erection, but
the CBT would not permit that. I turned on the light looked at the CBT.
My cock had swollen to fill the CBT, but it would not allow me room for an
erection.

"Mary, I need the key to get this thing off," I said.

"You'll get over it," she said, "just be patient."

"No! Give me the key!" I demanded.

"Sorry, no key," Mary said. She quickly pulled on some clothing and left.
I heard her car start and she drove away. I was on my own, and in serious
discomfort.

I got up and showered and found that my erection had subsided, and I was no
longer uncomfortable. I was pissed, but could cope with this. Mary and I
would have a serious talk tonight.

I got dressed and went to the office. I was surprised that the CBT
remained hidden under my clothes, so at least my humiliation would remain
secret.

I was surprised to find that for brief times I forgot it was even there.
Then I would move in my chair and notice it. It was difficult maintaining
a civil disposition, but I tried to act normally so I didn't arouse
suspicion among my employees.

Arriving home that evening I confronted Mary.

"This has gone far enough!" I shouted, "I'm through with this so give me
the key."

"Not a chance," said Mary, showing an evil smile, "I don't have the key
with me – it is in a safe place."

"I've done the trial and decided against it – you can divorce me." I
said.

"I've decided to keep you in chastity," she said, "it will be good for both
of us."

"I won't stand for this!" I protested.

"Yes you will," said Mary, "and you better not try to get out of it –
you could seriously injure yourself if you try. Now come back to me when
you have calmed down and I'll tell you the new rules."

Mary walked out of the room, leaving me much to think about. It took
awhile for me to calm down, but I finally realized that I was in no
position to bargain. Once she had the device on me she was in charge. I
decided to play along, and when let me out I just wouldn't let her put it
back on.

I found Mary and said, "I'm calmed down now."

"Good," said Mary, "I hope you are ready to listen."

"Mary continued, "You are going to live under a new set of rules. You will
never again put your cock in me – I will see as many men as I wish, and
if you are good I may let you watch. Depending on how you behave, you will
be released from the CBT from time to time and permitted to cum. How often
will depend upon you. For now we'll try once a week."

"Once a week?" I protested, "I'm used to cumming every day!"

"Well then, you should be really ready to cum after a week." replied Mary.

For the next week I begged Mary every night to let me cum, but she told me
I'd have to wait, and be good."

I felt like my horniness was going to kill me, but I was on my best
behavior, not wanting to do anything that would extend my chastity wait.

Finally it was Friday night, and I meekly approached Mary and begged for my
release.

"You've been good so far and I will release you. If you do what I say, I
will let you cum.

She directed me to undress, which I did. Mary led me into the living room,
where the d****s were all closed. "You don't want the neighbors to see
now, do you?"

I agreed and Mary showed me a pair of handcuffs, and told me to put my
hands behind my back. I refused and she said I could wait another week.
After pleading with her she agreed to give me another chance. I put my
hands behind my back and she cuffed me securely.

"Ok, now release me." I said.

"In a moment," said Mary, "I'll call for the key."

She placed a call on her cell phone and said, "bring the key in."

The front door opened and a man I didn't recognize came in. "Jerry, this
is Brad," she said, "who has kept your key safe for me." He handed Mary
the key and she unlocked the brass lock, but did not remove the CBT. Since
I was handcuffed I could do nothing but stand there.

Mary removed the CBT and massaged my cock and balls, bringing me to
erection. "You look very ready to cum," she said, "I'll give you a nice
climax if you do what I tell you."

"Ok," I said, "I'll do anything you want, but please make me cum!"

"That's what I like to hear," Mary said, "now kneel"

I dropped to my knees and Brad unzipped and took out his cock. "Now suck
his cock," Mary ordered.

"Hell no, I'm not like that!" I insisted.

"But you will be, if you ever want to cum again," insisted Mary.

She knelt next to me and took my cock in her hand. "Wouldn't a nice climax
be just what you need, now?"

"Yes, please make me cum," I pleaded.

"Jerry, just do what I tell you," directed Mary, "now open your mouth."

I opened my mouth and Brad put his cock in. I knew that further resistance
was pointless, so I closed my mouth and began to suck him. I couldn't
believe I was sucking a cock. Mary stroked me, rewarding me for
cooperating.

I continued to suck Brad and soon he was pumping his hot load into my
mouth. It had a strange taste that I didn't like, but I found I could
endure it in my aroused state.

"Now swallow," Mary said, and I did. She stroked me faster and I came. It
felt so wonderful, and I felt grateful to Mary.

She caught my week-long load in her hand and brought it to my mouth,
saying, "lick up your cum and swallow it."

I thought about refusing, but I dared not. I licked up my cum and
swallowed.

Brad thanked me for the blowjob and I felt ashamed for what I had done.

Before I knew what had happened, Mary caged and locked my cock. She
unlocked the handcuffs and said, "you can go now – Brad will fuck me and
I'll then we'll discuss this.

I left the room, feeling more humiliated than I could ever remember.










I sat in the kitchen awaiting Mary's return. I felt so humiliated – I
just sucked a guy off who was now fucking my wife, and I couldn't even
control my own cock.

After a time Mary came into the kitchen and said, "You gave Brad a great
blowjob and I didn't think he would be ready for a fuck that soon, but he
did well.

"Why all this humiliation?" I asked, "isn't it enough that you have control
over me?"

"We are just beginning," Mary said, "You will face humiliation you cannot
yet imagine."

"Why?" I asked.

"It is your punishment for cheating on me," she said, "the chastity belt is
simply a means to accomplish that humiliation."

Mary took me to the computer in the kitchen and pulled up a web site. I
could clearly see pictures and videos of me sucking Brad, and eating my own
cum.

"I can easily send links to this site to anyone I wish," Mary said, "you
have a lot of employees and many ties in the community – many who you
would not want to know you are a cocksucker."

"I wonder how your mother would react?" she continued.

"You fucking bitch!" I yelled.

"I will forgive your outburst this time, but don't forget who is in charge
here," she reminded me.

I was like a muzzled dog – there was nothing I could do.

I began to accept my new life – getting hornier and hornier every day,
but looking forward to Friday evening.

Finally Friday arrived and Mary asked if I was ready, and I said I was.

"This will be similar to last Friday," she said, "but this time I want you
to ask Brad permission to blow him."

She was ratcheting up the level of humiliation, but I had no choice but to
comply.

I undressed as she directed and she led me into the living room. The
d****s were wide open so anyone outside could see what I was about to do –
more humiliation.

Mary handcuffed me and then removed my CBT. I dropped to my knees and Brad
walked in.

"May I blow you, Brad?" I asked as Mary had ordered.

"I don't know," said Brad, "how badly do you want it?"

Mary nudged me, so I responded, "please let me suck you – I want it
badly."

"Ok," said Brad, "since you asked so nicely."

Brad fed me his cock and I sucked him. It was only my second time with a
cock in my mouth, but I found it strangely pleasant. I sucked Brad, and
soon he climaxed. The taste was strong, but not as bad as the last time.
I swallowed and he pulled out.

"Thank you," I said, not knowing why – it somehow seemed the thing to
say.

I looked to the living room window and was horrified to see some men
standing outside the window looking in. One had a video camera and another
had a still camera. I wanted to run away but did not dare.

Mary directed, "I want you to hold Brad's cock in your mouth while I jack
you off."

I knew that it would make especially humiliating pictures to show me
cumming with a cock in my mouth, but I had no way out of this, so I opened
my mouth and took Brad into my mouth while Mary stroked me. I was very
ready to cum, but with Brad's cock in my mouth I was even more aroused, and
soon shot my load into Mary's hand. She brought it to my mouth and I ate
my cum while the cameras caught everything.

Mary put the CBT back on me and unlocked my handcuffs.

"You did very well tonight," she said, "come to the bedroom with Brad and
I."

I followed them to the bedroom, still naked.

Mary closed the d****s and the door. I want you to help Brad get hard
again so he can fuck me, then you may watch and clean us up afterward.

I dropped to my knees and began to suck Brad. He had just cum, so he might
need some time to recover. My hands were no longer cuffed behind me, so I
was free to use them. I was surprised when I instinctively put my hands on
his ass cheeks, pulling him to me as I sucked. Soon Brad said, "that's
good, I'm ready." and pulled out. Mary was already lying on her back, legs
spread. I saw that her pussy was shaved – something she had never done
for me.

Brad mounted her and fucked her. She was far more vocal than she ever was
with me. Brad finished and stood before me. I opened my mouth and he put
his wet cock in. I sucked the combination of cum and pussy juice from his
cock and he pulled out.

"Now clean me up," said Mary, legs wide apart. I climbed onto the bed and
brought my mouth to her pussy. Brad's cum was on the outside, so I licked
it up before slipping my tongue into her pussy. I tasted a bit of Brad's
cum, but mainly tasted pussy. I had rarely gone down on Mary, and wished
that I had done more. As long as I was there, I found her clitty and began
to lick eagerly. Soon Mary climaxed and thanked me.

As I lay in bed that night it hit me that the only sexual contact I would
ever have with my wife would be to lick another man's cum from her pussy.
She had turned me into a cuckold and a fluffer.

Tonight was even more humiliating that last Friday – I wondered how she
would attempt to further increase my humiliation.






The next morning Mary told me that I was to blow Brad any time he asked me
to. I wasn't surprised, given all that had happened. What surprised me
was that I was actually beginning to like blowing him, though I could never
admit it. Mary making me blow him on demand was just another level of
humiliation.

On Wednesday morning I recieved a call from Brad.

"Do you have any time for me today?" asked Brad.

"I can see you at 1pm," I replied.

"Ok," Brad answered, "I'll come to your office."

I hung up and immediately realized I had invited Brad to my office for a
blowjob. I couldn't blow him in my office because of all the windows. I
wondered where I could blow him in privacy. There was a small four person
conference room that had no windows. I called my administrative assistant
and asked her to reserve it for me at 1, and that I was not to be
disturbed. I sure couldn't have my employees know I was a cocksucker!

Brad arrived a little before 1 and I greeted him. I led him to the small
conference room and closed the door behind us and locked it. "I know this
is really difficult for you," he said, "no man should endure what Mary is
putting you through."

"I agree," I replied, "but I really fucked up, and brought it on myself."

I got to my knees and Brad unzipped. As I sucked him I realized that I
really liked doing this, and wondered how many more guys I might end up
sucking. The sucking would be ok if the humiliation could be avoided. I
sucked him and soon my efforts were rewarded. I found that I actually
liked him cumming in my mouth. I was becoming a faggot. I vowed to
pretend I was being forced to suck – I couldn't have anything think that
I liked it!

Brad left and I continued my work day.

Friday arrived and I was looking forward to cumming again, but apprehensive
about how Mary would escalate my humiliation.

After undressing, Mary led me into the living room. Once again the d****s
were wide open. She cuffed my hands removed the CBT.

"This week we begin something new," Mary explained.

Instead of blowing Brad," tonight you will blow ten men who know you. They
will see you and know that you blew them, but you won't know who they are.
They are randomly chosen from the people you know – some from work, some
from the community, and perhaps some from church. As you go through your
day you will never know who you interact with that knows your secret."

My heart lept as I realized the exposure I was facing. "Please Mary," I
begged, "don't do this to me!"

"The arrangements have already been made and the men are waiting," she
responded, "even if I cancel they will know your secret just the same."

"Is there anything at all I can do to change your mind?" I pleaded.

"I understand how humiliating this is, and I really do feel sorry for you,"
she said, "but this cannot be aborted."

I took a few deep breaths to ready myself for my ordeal. Mary opened the
door to the garage and brought in ten men, naked, but wearing identical
black ski masks. I had no way of identifying the men, but they could
clearly see me kneeling there, naked and ready to blow them.

They approached and began to surround me. Mary stopped them and arranged
them so they didn't block the view of the camera people outside the window.
She moved them into a suck line before me. I sucked each of them,
swallowing their loads. They were silent, probably not wanting to risk my
recognizing their voices. As I finished sucking each guy, they stood off
to the side, watching me suck the others. After finishing the last guy,
they stood and watched Mary jack me off and feed me my cum.

The men then left. I stood and Mary put the CBT back on me and removed the
handcuffs. "I didn't want them to see the CBT because I wanted the guys to
think you did this voluntarily."

She was cruel indeed in her humiliation of me.

"How was that?" Mary asked.

"I am so ashamed I cannot find the words for it," I responded.

"We will do this for another five weeks. The men will be randomly selected
from all the men you know. Some will be repeats, but most will not. At
the end, you will have blown about half the people you know, without
knowing exactly who.

"How do you feel?" Mary asked, "ok, but my stomach feels a little uneasy."

"You've swallowed a lot of cum," she said, "but you didn't throw up, so ten
loads are not too many for you."

Mary dismissed me and I left. I didn't know how I would cope now, not
knowing if the people I was with knew my secret – and would they keep my
secret, or would everyone know soon?

I slept uneasily that night, and was glad that I had to weekend to adjust.

The next week I was extremely nervous on Monday. Every time I saw someone
joking around I wondered if it was at my expense. I decided that I could
drive myself crazy by second-guessing all that was happening. Brad stopped
by for blowjobs twice, which I enjoyed.

On Thursday I received an anonymous email from a guy who identified
themselves as "load4u". It simply said:

"I really enjoyed your blowjob last Friday – you seemed to like it, and
I would love another, if you are willing. I will be discrete and await
your reply."

Getting that email scared me. I really didn't have anything to risk by
responding, since he already knew I was a cocksucker. I sent a quick reply
and asked when he would like to meet, and sent it off.

I few hours later I received a reply from him – he identified himself
and I immediately recognized him as Brent, one of my senior math modelers.
He asked if he could stop by my office at 5pm, and I replied that it would
work.

At 5pm Brent stopped by my office and we went to the small conference room,
where I locked the door behind us. "I feel really uneasy about approaching
you like this," Brent said.

"I'm uneasy about it also," I said, "so lets just get to it."

Brent unzipped and I dropped to my knees. I sucked him for about five
minutes and he came. He thanked me repeatedly and I asked him how often he
would want to come back for more." He was a little tongue-tied, but
blurted out, "how about twice a week?"

I agreed and told him to schedule 5pm appointments with my administrative
assistant, for "Model updates".

He thanked me and left, and I went home.




It was Friday again and time for my weekly humiliation. It seemed that
every week Mary had a way to increase the humiliation level.

"I have a couple of surprises for you – one you will like, the other you
will not." said Mary, standing next to Brad.

I said nothing, lest I make my situation worse, but just listened in
silence.

The good news is that you won't have to wear the CBT any more – we have
so many pictures and videos now posted on our website that I just know that
you will cooperate with whatever I order you to do!

"Thank you," I said, "so what's the bad news?"

This week you will blow another ten men who know you, but the entire time
you will be stroking your cock – just enough to remain hard, so they can
all see that you are aroused from sucking them. After the last man cums in
your mouth, you are to continue to hold his cock in your mouth while you
stroke yourself to completion, shooting into your hand and swallowing as
they all watch.

She had definitely raised the bar on my humiliation, and I shuddered to
think of what would be happening next.

I was naked and in position in the living room, when Mary said, "Why don't
your warm up with Brad?"

Brad immediately unzipped and offered me his cock, which I obediently
sucked. I secretly enjoyed sucking Brad, but hoped it wouldn't be noticed.
Soon Brad unloaded in my mouth and pulled out. I swallowed as Brad stepped
out, and Mary led this week's ten men into the room. As before, they all
were naked and wore identical black ski masks.

I sucked one after the other, stroking myself enough to maintain an
erection, but not cum. Each man came and stepped aside and watched as I
sucked the remaining guys. When I finally finished sucking the last guy I
held his cock in my mouth as directed and stroked harder, to bring myself
to climax. I pulled back from his cock and swallowed, and then licked up
my cum. Mary began to applaud and the guys joined in. I just felt
terrible about this. I didn't even want to consider what Mary had in store
for me next week.

After the men left Mary came to me and said, "You endure your humiliation
very well," she said, "now one last bit – each of these men will receive
an email, apparently from you, thanking them for cumming in your mouth and
telling them you would like to set up a private session to suck them
whenever they wish."

"Mary," I protested, "when will enough be enough?"

"I'll cut you some slack then," Mary said, "You have four more weeks left
blowing guys who know you – we will make next week the last one, but it
will be the most humiliating so far."

"Then it's over?" I asked.

"That part is," Mary agreed, but I may come up with some other treats for
you.

"Lot's of guys have affairs!" I protested, "and they never go through
this!"

"They would if they were married to me!" she said, "be thankful I don't
have you castrated!"

I shut my mouth to avoid making my situation worse.

All of this humiliation was emotionally taxing and tiring as well, so I
fell asleep quickly that night.

- - - - - - - - - -

I awoke on Saturday and went into the office. Ben, the security guard on
the main floor greeted me and approached. "That was a great time last
night," he said, and I'd like to set up private sessions, as you offered."

"When would you like to do it?" I asked.

"I go on break at 10 this morning." he replied.

"Fine," I said, "come up to my office then." I carried a card in my shirt
pocket for notes, so I jotted down "Ben 10am"

Mary had been fast in getting those emails out. Humiliating me must be the
most important thing in her life right now. When I got to my office Matt
from accounting stopped by. "I wanted to see about private sessions, as
you suggested."

"This morning ok?" I asked.

"Sure," he replied.

"Come back to my office at 10:30 then," I offered, and he agreed, and I
made a note of it.

I was in the building for less than an hour and already had two blowjob
appointments! I wondered if I should just disappear and run off to South
America.

Ben and Matt showed up for their blowjobs as planned and I sucked them in
the small conference room where I had sucked Brad and Brent. On the way
out, Ben thanked me over and over again, adding, "I never would have
figured you for a cocksucker!"

This was quite enough so I left the building. After all, it was Saturday
and I needed to stop at the bank. As I entered the bank door Charles, the
branch manager waved me into his office.

"I was so surprised to see you last night," he said, "but sure love your
work, and want to arrange for more – it's so wonderful of you to offer."

We discussed when and where and he said the bank closed at noon today and I
could go for a ride with him. So here I was agreeing to give a car blowjob
– I just hoped that I wouldn't get busted doing it.

I took care of my banking, and since it was nearly noon I just enjoyed a
coffee and waited for Charles. We left and got into his spacious Lincoln
Town Car and he drove to a nearby car pool parking area. He parked and
took out his cock. I looked all around to make sure we weren't seen, and
put my head down and sucked him. He kept saying how much he needed this,
since his wife doesn't put out any more. He rambled on that it was great
for me to provide this public service and he would spread the word to his
friends.

He came and I swallowed, and was anxious to get away from Charles. I
really hoped that he would forget about telling anybody else, because way
too many people already knew.

I returned home, intent upon relaxing the rest of the day. When I checked
my email I found four emails requesting private sessions. I just shut the
computer off without answering.





Throughout the week I found that nearly everyone replied to the emails Mary
sent. Some declined but seven of the ten said they wanted more. While I
had no choice in the matter, I felt really conflicted about all this. I
was outraged at what I had been forced to do, but was really enjoying
cocksucking. Now that I had been "outed" to so many people I knew, it
could not be undone, so there was no point in denying it. My wife thought
I hated the cocksucking – in a perverse way, my enjoyment of it was my
way of getting back at her.

On Friday night I reported to Mary for my weekly humiliation event. She
told me that it would be the last time I would be anonymously sucking off
guys I knew, but it would be the most humiliating of all.

"You won't be naked tonight," said Mary, "I have something very sexy for
you to wear."

By now I knew that was best to remain silent – nothing I could say would
help me out, and I could make it worse for myself.

Mary guided me to put on a black garter belt and black hose. Then she put
the bra on me. There were breast forms that gave me some shape.

Next she put a wig on me – it was brown and shoulder length. She told
me I looked pretty and my shame grew as she brushed my hair. The final
touch of my humiliation was red lipstick, after which she took me to a
mirror and I looked in horror – I looked like a complete sissy!

"I would put panties on you, but I want everyone to see how aroused you
are," she said, "so like last week you will stroke yourself and cum after
your last blowjob."

My humiliation was at its maximum as I stood there, but I knew that the
worst was yet to come.

Mary led me to the living room and placed me on my knees. She led
tonight's men in and I heard a combination of responses – some laughter,
some "oohs" and "ahhs". The first guy approached and said, "that's a
pretty mouth, sissy bitch."

I sucked him as tears formed in my eyes. He came and I swallowed and
pulled out. Mary stepped forward and said, "just a moment, a girl likes to
look her very best." She told me to lick the cum off my lips and then
wiped my lips with a tissue and refreshed my lipstick.

I continued sucking, getting my lipstick refreshed between each blowjob.
Some guys seemed oddly affectionate, talking softly to me, "I didn't know
you were like this – I want to be with you."

That was a bit much for me, and the tears in my eyes streamed down my
cheeks. He said, "poor dear – I promise that I'll treat my girl with
tenderness."

I couldn't really understand how I felt about this – in the brutality of
Mary's humiliation of me was someone who expressed compassion for me –
but as a woman!

I tried to do my very best in sucking this man, and felt especially good
about pleasing him.

After refreshing my lipstick I sucked the next guy. This continued until
the last guy. As I did last week, I held him in my mouth after he came,
and stroked myself to climax. I swallowed his cum and released him, then
swallowed my own cum.

Mary led the men out and returned to me. "Stand up," she commanded, which
I did. She told me I really messed up my lipstick while sucking and wiped
the smudged lipstick from my face and put new lipstick on me.

"There are two men who want to see you," she said. She led one in and he
approached me, still naked and wearing the ski mask.

He took me into his arms and grabbed my ass as he kissed me, driving his
tongue deep into my mouth. It was disgusting to kiss a man, but I endured.
He ran his hands all over me, caressing my cock and balls. "Will you be my
girlfriend?" he asked.

"I'll think about it," was all I could think to say. He said he would be
in touch, and left.

Mary led the second guy in, who also embraced me and kissed me deeply.
"You are the kind of girl I like," he said. As he caressed me he slipped a
finger between my ass cheeks and pressed it into my hole. He wiggled it
around as he worked it in and I was surprised at how good it felt!

He brought his mouth to my nipples and sucked. I had no idea a man's
nipples could feel as good as he was making me feel. Suddenly he released
me and I felt a bit of disappointment.

Mary led him out, and returned, asking, "How did you like that?"

I lied and said, "It makes me want to puke!"

"Maybe for now," she said, "but we'll see."

Brad had been watching the entire time, fully erect the entire time.

Brad took me into the bedroom and whispered to me, "You look really hot –
if Mary wasn't here I'd be kissing you as well."

I wished he would, but had to pretend I didn't want it.

Mary came in and said, "Bend over onto the bed – Brad is going to claim
your virginity and give you a fuck you won't forget!"

She ordered Brad to force himself into me roughly, and without lube.

As he positioned me he whispered in my ear, "pretend it really hurts."

He pressed his cock head to me and pushed gently. "It hurts – oh please
don't do this to me!" I said.

Mary said, "good, I want you to remember this well."

"I can't get in without lube," said Brad.

"Ok, use just a little – I want my sissy husband to feel every bit of
your entry."

Brad must have not let Mary see the amount of lube, because he used quite a
bit, and gently pressed a couple of fingers into me before pulling them
out. He pressed his cock head to my hole and gently eased into me – it
really felt wonderful.

Putting on a good show for Mary, he said, "I'm going to rip you open,
bitch!" and the pushed in all the way. Since he had the head already in
me, the thrust caused me no pain, but was felt great, and I played along
and yelled out, "damn! please, no more!"

"Keep that up and I'll show you some real pain," said Mary, "bury your face
in that pillow and cry all you want, sissy, but I better not hear any more
yelling."

I did bury my face in the pillow to put on a good show, but loved the
fucking I was getting from Brad. He fucked me for only a few more minutes
before cumming, and I pretended to endure while I actually enjoyed every
moment of it!

Brad collapsed on me and I found that I liked the feeling of his body
pressed against me. Mary left and told us to clean up. After she left I
thanked Brad for his kindness and told him I really enjoyed the fucking.

He pressed his mouth to mine and I welcomed his kiss, sharing my tongue
with him. I was surprised at how my feeling about kissing men had changed
so quickly.

Brad and I cleaned up, and he said he wanted to see me as a girl, but
didn't want Mary to know. I told him that we would find a way.















Throughout the week I gave over a dozen blowjobs by appointments – the
result of my humiliation events and Mary's emails. I had kind of settled
into doing them and some of them were really nice.

What especially disturbed me was two anonymous emails that told me how hot
I was dressed as a girl, and asking if I would be their girlfriend. A man
sucking cock is humiliating enough, but to dress in women's clothing is
even worse. I was terrified at having to dress again, especially to arouse
men and bring them to climax.

Brad came by twice for blowjobs and repeatedly asked me if I would dress
for him. He said that when he fucked me last Friday it was the hottest
fuck he had ever had – much better than Mary. Mary would really be
pissed at me if she knew I was a better fuck than she was, and who knows
what she would do to me?

The part that troubled me the most was that I really WANTED to dress for
Brad! When he kissed me I actually liked it. When he had finished on
Friday I nearly promised him that we would find a way to make it happen.
Now he has been pressing me to actually do it.

I wondered if I could do it just for Brad and nobody else – I didn't
know if the guys who sent me the anonymous emails would make trouble for me
if I resisted – so far I have given in to all demands, which has kept me
out of further trouble, but it also got me deeper into the net of
perversion that Mary has cast over me.

Mary wasn't done weaving the web she had trapped me in – she told me to
arrange to take Friday off because she had something special in mind for
me. She had a diabolical mind, and I really feared what she had in mind
for me.

When Friday finally arrived Mary and Brad drove me to an upscale house
across town. A pretty blond woman greeted us and invited us in. She was
introduced as Linda and said she would be working with me today. Mary told
me that I was to cooperate in every way or else.

I didn't need to know what "else" meant, so I just nodded. Linda led me
into a bedroom and told me to undress, which I did. "What are you going to
do to me?" I asked Linda.

Linda smiled and revealed, "I am going to make you into a woman every man
will want."

My heart sank – it was getting worse and worse.

"Look," said Linda, "I know you are being punished and you don't want any
part of this – but fighting me wont' help."

"Besides," she continued, "a lot of guys who are involuntarily feminized
really grow to like it – many actually come back and thank me."

That is what scared me the most – already I was liking some aspects of
just wearing women's clothing – would this be the end of my being a
man?"

"Are you going to do anything surgical?" I asked, with trepidation.

"Don't worry!" Linda said, "you will still have all your parts – but you
will look amazing hot!"

I was relieved to hear that as Linda led me into a pink bathroom and told
me to get into a bubble bath. "Just soak and enjoy being a girl," Linda
said, "afterward we'll shave you."

I soaked for awhile, not feeling the least bit femme. Linda came in and
told me to get out of the tub and she helped dry me off. She led me into
the bedroom where she had me lay face down on a massage table. Three
people joined her and they rubbed cream on my skin and proceeded to shave
me.

They didn't miss a spot. Linda spread my ass cheeks and told one of her
helpers to be thorough – men didn't like a girl with a hairy crack!

Linda told me to roll onto my back and shaved the front of me – when
they got to my pubic area they used an electric beard trimmer and cut my
pubic hair short, and then shaved the hair into the shape of a heart.

Linda led me back into the bathroom and told me to rinse off. I did so, and
then dried off. She led me to a full length mirror and was surprised at
how nice my body looked – if not for the cock and flat chest, it could
have been a woman's body.

"Tuck your cock between your legs," directed Linda, which I did.

Without the cock, I just saw a heart shaped patch that could easily be a
pussy!

Linda's helpers approached me with several seamstress tapes and measured
all parts of me. Soon they brought items of lingerie to me and I slipped
them on. The black hose and a lacey black garter belt looked a lot like
what I wore last Friday. They put a matching bra on me, with breast forms.

"For your body size, C size is just right," commented Linda.

They slipped black lace panties on me, which fit, except for my bulge.
Linda led me back to the mirror. "Ignore the bulge," Linda said, "I'll
show you how to hide it later."

I was amazed to see a woman's body in the mirror. My bulge grew just from
looking at myself! I realized that every week Mary had changed my life in
a way I could not go back, and this was simply more of the same.

Linda led me to a chair like they have in beauty shops and they worked on
my face. They plucked my eyebrows and trimmed my nose hairs. Linda
commented, "a guy can get by with some unruly nose hairs, but no girl
would!"

"Now pay attention," Linda continued, "we are going to teach you how to
make up your face – you won't remember all of it, but do your best. You
will be back for a refresher, so after a couple of visits you'll have this
down pat."

It began to dawn on me that this wasn't just a humiliation – it was a
change in my life! I seemed to not have any option, so I just went with
it. I thought of Brad, and realized that deep down I found being femme to
be fascinating. Linda and most of her helpers stepped out, leaving me with
only one – a young man. "I think you are warming up to this," he said,
"aren't you?"

"No," I blurted out, "No way!"

He put his hand on my bulge, now straining at my panties. He massaged my
bulge and I groaned. Next his mouth was on mine, tongue probing me. I
relaxed and kissed him back.

"I thought so," he said, "there are a lot of men who love girls like you!"

He broke away as Linda and the others returned. They put shaving cream on
my face and brought a mirror near and told me to pay attention. She
explained that I needed to learn to do a 4-way shave: one pass each with
the grain, one against the grain, and across in both directons. That would
remove as much of the whiskers as possible. She explained that while most
men shave in the morning, I should start shaving a few hours before my date
in order to get the most time from the shave.

After drying my face, they showed me how to apply a good foundation that
would help hide a five o'clock shadow as long as possible. Then a bit of
color – nothing very heavy so I wouldn't look like a painted lady.

That was just great – I was going to BE a whore, but didn't want to LOOK
like one!

Linda said my eyelashes were large for a man, so I wouldn't need to use
artificial ones, but showed me how to put on mascara, eyeliner and eye
shadow.

"You are already naturally pretty," said Linda, "so you want to put on just
a hint of makeup – just enough to accept your features."

As I looked at the mirror I couldn't believe how my face had changed.
Linda led me to another room where there were a variety of wigs on stands.
She chose several and asked me which I liked the best. I chose a black
shoulder length wig and Linda took me back into the other room. She showed
me how to put the wig on, and how to brush it as I wore it.

One of her assistants brought in a rack of dresses and shoes. We chose a
dress, which I slipped on. Linda chose a pair of shoes with two inch
heels. "Eventually you will want higher and thinner heels," she said, "
but for now you need to learn how to walk in these."

I put the shoes on and we spent the next hour practicing walking, sitting
and learning a variety of feminine mannerisms. It was a lot for me to
learn, but I was doing the best I could. They even instructed me in how to
eat like a woman.

"You are nearly ready," Linda announced, "we just need to show you how to
hide your bulge."

One of her assistants lifted my dress to the waist while another pulled my
black panties down. Released from the panties my erection sprung loose.

"We have to start with you soft," said Linda, and asked one of her
assistants to help out.

In full view of the mirror I saw the man who had kissed me take my balls
into one hand while stroking me with the other hand. It was an incredible
hot image in the mirror and soon I was cumming. The guy held a tissue to
catch my cum and threw it out.

He told me to step out of the panties now at my ankles, and told me to
spread my feet apart. I was now soft, and he wiped the last droplette of
my cum off me. He tore off about eight inches of duct tape and taped my
soft cock under me. He explained that I had to make sure to avoid my pubic
hair because it would hurt upon removal.

I put the panties back on and the guy held my dress up while I looked in
the mirror – there was no bulge at all!

Linda said I was now ready, and led me out to another room where Mary and
Brad were kissing on the couch. They stood up and looked me over, smiling
at the result of Linda's work.

"I've given Brad an assignment for tonight," Mary said, "he was reluctant,
but now has agreed to be your dinner date tonight. Your name is Jennifer,
and you will treat Brad as an appreciative lady should."






Brad picked me up to take me to dinner. Now, as Jennifer, I would be
Brad's dinner date, after which he would take me to a club where Tgirls go
to meet men. I wasn't particularly looking forward to that because I
feared seeing men that I knew.

Just the same, I did look forward to being on a date with Brad. I knew
that he liked me as a girl, but I knew he didn't want Mary to know. While
Brad was a party to my ongoing humiliation, he was nice to me, so I would
pretend to Mary that I was simply submitting, but not enjoying.

Brad walked me to the car and got my door for me – he knew how to be a
gentleman! He told me that I looked really pretty, and I hoped he was
right – not just buttering me up. I slid next to Brad and put my hand
on his leg, moving my hand to his crotch. I could feel that he already
aroused, and knew he would need draining, and I wondered how he would have
me do it.

Brad was a perfect gentlemen as he escorted me into the restaurant and with
my chair. "Does my voice sound femme enough?" I asked.

"It will get you by tonight," Brad replied, but I'm sure it will get better
with practice. Would you prefer that I order for you?"

"Thank you," I replied, "but I'd like to see how I do." I was beginning to
believe that Brad's kindness was driven by more than just his hard cock.

"I like being with you, Brad," I said.

"I like being with you," he returned, "but Mary must not know."

"I understand," I responded, "I will make sure that Mary thinks that you
are just humiliating me, but I hope we can enjoy our time together."

We had a nice dinner and I couldn't help but realize what dangerous
territory I was in. Having an affair with a woman is what got me into the
mess I was in, and now I was having an affair with Brad. Mary would be
really pissed if she ever found out, so I needed to be sure she never did!

After dinner Brad walked me to the car. It was getting dark and the
parking lot was not well lit. When we got to the car, Brad asked, "Would
you please take off your panties?"

He asked me – that was wonderful – I knew that I really didn't have a
choice, but he was being so nice about it. I removed my panties and handed
them to Brad, and he stuffed them into his pants pocket.

Brad kissed me and slipped his hand under my skirt. I kind of liked it,
and when he felt the tape that was holding my cock in place he asked me to
remove it.

"But what if Mary checks me and finds it gone?" I asked.

"You can put it back on afterward," Brad replied, "if Mary says anything
you can tell them that you can tell her that you had to pee."

He said "pee" and not "piss" – even now he was being gentlemanly.

I pulled off the tape, glad I had been shaved, and handed the tape to Brad.
He stuck the end to the rearview mirror so I could use it again.

Then Brad did something completely unexpected. He knelt down, lifted my
skirt and began to suck me. Brad, of all people was sucking me. I had no
idea he would do such a thing. I was breathing harder and soon I came in
Brad's mouth – it felt so wonderful!!!

Brad swallowed and stood up, leaning over to kiss me. "Do you want me to
rinse my mouth out first?" he asked.

I pulled him to me and kissed him, reaching my tongue into his mouth,
tasting the cum he had just milked from me.

"Mary must never know," Brad said, "she would kill me!"

"She'll never know from me," I said, "but I'm so surprised about this."

"Jennifer, dear," Brad said, "you may not understand this, but a girl like
you brings out something in a man that is normally well hidden."

I replaced the tape holding my now-soft cock in place and Brad opened my
car door, letting me in. I hoped that I could bring out more of his hidden
surprises.

Brad drove me to the club and walked me to the door and inside. Mary was
there and Brad took me to her.

"Pick Jennifer up at 11pm and feel free to have your way with her then,"
said Mary.

Brad departed and I was now under Mary's supervision.

"How was your dinner with Brad?" asked Mary.

"Dinner was fine," I responded, "but I was so humiliated as he paraded me
around for everyone to see!"

My attempts to protect Brad proved effective when Mary said, "Good, then
Brad is doing his job – I think I'll have him spend more time with you."

I liked the sound of that, but put on a pouty look to not give it away.

"Careful," cautioned Mary, "or I might just put Brad in charge of you!"

"What do you expect of me tonight?" I asked.

"I want you to mingle here, and meet men, and be nice to them – VERY
NICE! – You know how to please a man, so make sure you do."

I felt really uneasy, but fortunately men came up to me and asked me to
dance or to buy me a drink. I danced with some of them and felt their
hardness against me. When they asked if I would blow them I quickly
agreed, and we went out to the parking lot. The lot was not lit, so there
was good cover from the darkness. I saw that several other girls were
sucking their guys.

As soon as the guy came, I swallowed and he thanked me, walking away.
These guys were certainly not gentlemen, and made me appreciate Brad even
more.

The guys who bought me drinks talked with me, but they really didn't know
what to say, so I usually helped get to the point by asking, "Is there
anything I can do for you?"

At this point some would ask for a blowjob, while others couldn't seem to
find the words, so I had to offer.

I preferred giving blowjobs to getting fucked, because they are fast and
not at all messy.

By the end of the evening I had given nearly a dozen blowjobs, probably all
that I can safely swallow. Mary had been watching me most of the night.

Mary approached and said, "You've done a nice job in pleasing the men –
how did you like it?"

I did like it a little, but couldn't show it. I replied, "I'm just doing
what you told me to do – I recognized about half of the guys – I just
hope they didn't know who I am."

"They do now!" said Mary, "I made a point of telling every one of them!"

Mary was a master of humiliation, and I saw no end to this. An occasional
good time with Brad was the best I could hope for.

Brad came in at 11 as ordered and led me away. Once outside, he tried to
kiss me but I stopped him, saying, "Please don't – I've been giving
blowjobs all night."

He pressed his lips to mine parted them with his tongue. I wished I could
just run away somewhere with Brad, but I knew that would never happen.

Brad ran his hands over my buns and I instinctively spread my feet apart.
He lifted my skirt to my waist and slipped a finger between my cheeks. I
would have to remember to get my panties back from Brad before we get home.

"You're dry," Brad said, "I'll hurt you if I try without lube."

"I have some in my purse," I said, handing him some.

Brad was wonderfully gentle as he applied lube and worked his fingers in
and out of me, preparing me for his cock. Soon he was pressing into me and
I welcomed his entry. He gave me a good fucking and wrapped his arms
around me as remained in me after he came.

"Oh Brad," I said, "you are so wonderful! I just wish I could always be
with you."

"Let's just take it one day at a time," he responed.

He pulled out and used a wet wipe to clean up. I knew that some guys made
girls like me clean them up in their mouths, and I was grateful to Brad for
his courtesy to me.

Brad drove me home, and Mary was waiting for me.

"This is just the beginning," she said, "You will be spending the rest of
your life as a woman."

As I lay in bed that night I feared what lay ahead, but did enjoy my time
as a girl.