This story contains graphic depictions of adults involved in consensual
sexual activity. If these types of situations offend you, or if you are
prohibited by age or geographic area from viewing such stories, then please
turn back now. The author will not be responsible for those who illegally
view this information and will ignore responses from those who are offended
by it. You have been warned.

From Mob to Shemale

Two years ago, I was a member of the Ciccio family in Chicago. I
wasn't very high up in the organization, because I wasn't Italian. I had
made my way up through the ranks, however, and was making a pretty good
living. I had everything I wanted, got all the girls I wanted, and did just
about whatever I wanted. One day I got sloppy. I slept with another
member's wife. It turns out that he didn't appreciate it much. Neither did
my wife. This is the story of how my life drastically changed after my
visit from Tony Ciccio.
I saw Tony drive up that day and didn't think much of it. He usually
stopped by about once a week for a pickup. I answered the door and invited
him in to the den. I had been sleeping with his wife for about a month and
a half now, but I remained cool and tried to act normal.
"Sam, I have some business to discuss with you. It turns out that you have
been sticking your little pecker where it doesn't belong."
I wasn't sure if he knew or if he was talking about some business deal
that he didn't think I should be involved in, so I tried to play it off.
"Tony, if you are talking about that thing with the mayor, I can back off.
I didn't know you wanted in."
"Not at all. I'm talking about something much different."
He pulled a video out of his jacket pocket and started to walk over to
the VCR. He pushed the tape in and pressed play. What I saw shocked the
hell out of me. It was Tony's wife and myself caught on tape in a very
compromising position. He had evidently hidden a camera in his bedroom
somewhere. I knew at that point my life was over. What I didn't understand
was why he even bothered to talk to me about it. Usually a transgression
that large against the family would be an automatic death warrant, with no
warning. I looked around to see my wife standing in the doorway. Tony
motioned for her to come over.
"Sam, I was very upset when I first saw this tape, and wanted to kill you
very slowly. I got permission from the family to have you whacked. But I
started thinking. If I have him whacked, then his poor wife Marie would be
mourning that sorry cheating piece of shit for a long time. So I shared the
tape with her. Needless to say she was pretty upset too. I told Marie that
I was going to kill you, and she has managed to talk me out of it, for the
moment. We have something much better in mind for you."
"What is it?" I asked, relieved that my life was going to be spared.
Anything was better than dead.
"I found out that you were banging my wife about a month ago. I set up
surveillance tapes in my bedroom, and I had a private investigator start
following you twenty-four hours a day. You can see an example of the
bedroom tape here. I also have some very good ones of you pulling your last
three jobs. I'm sure the district attorney's office would be very happy to
get their hands on this sucker. Here, take a look."
He turned off the bedroom tape and put in another tape from his jacket.
In the tape, you could clearly see my face. It was a scene from the
diamond heist we had pulled two weeks ago. We got away with over a million
dollars in gems, and the cops had no leads or clues. It was also footage of
two other big jobs we had gotten away with. This could definitely change
that.
"Marie came up with a very good alternative to killing you, and I like the
idea of it, for now. We could either kill you, send this tape to the D.A.'s
office, or the other option. When you are done, I don't know if you are
going to want to thank her or not, but you will be alive."
"What is it?" I asked.
"Marie has a friend that works over at the mental institution in the sexual
predator's unit. She has told me some of the stories of what they do there,
and I think it would be good rehabilitation for you to go. You will have to
attend four months of intensive therapy and counseling sessions. After
that, you will be free to go. I don't think you will be able to move back
in with Marie, but you will be a free man instead of dead or in jail. If
you decide to run, not only will we come looking for you, but I will release
the tape to the cops so you will have them on your tail too. If you run,
you better hope I never find you, because I won't be offering alternatives."
I was looking at fifteen to twenty years for the three armed robberies
on the tapes, and looking at a very short life with my other option, so I
agreed. Besides, only four months? I could do that standing on my head. I
also thought that all that psychological stuff was a waste of time and
wasn't worried about it in the slightest.
"Good. I thought you would choose that option. They have a room waiting
for you there already. We will get you checked in bright and early
tomorrow."
I went to sleep that night (alone of course) and slept pretty soundly.
I was going to live, after all. Who cares if I had to spend four months in
counseling? I would be out and banging broads in no time. I awoke the next
morning to Tony shaking me violently.
"Wake up! Time to begin your new life!"
I got out of bed and got dressed. I shaved and ate breakfast, and then
we got in the car and started our drive to the institution. Tony reminded me
in the car that they got daily reports from the staff here about my
progress. He told me that if I didn't cooperate fully, then I could expect
a visit from him and that it wouldn't be a pleasant experience. About forty
five minutes later, we arrived. We were greeted at the car by a very
beautiful, buxom nurse. I was thinking that this was not going to be such a
bad four months after all. I started to get my bag out of the car and she
stopped me, telling me that I wouldn't need it at all-everything was
provided for me. I threw the bag back in the car and wished Tony farewell.
The nurse lead me to my room and told me that my first session would
begin around 10:00. I looked around the room and noticed that it must have
been decorated for a girl before. It was completely pink, and had a lot of
ruffles and bows everywhere. The sheets on the bed were pink satin. She
told me that I had to get my inoculations, unless I could prove that I had
had all my shots within the last three years. Obviously I couldn't, so I
pulled down my pants and bent over. I felt a brief prick in my left cheek,
and then it was all done. She repeated the same on my right cheek. Then she
told me that I had to get out of those clothes, that all patients were
required to wear hospital issued clothes. As I took them off, she started
to fold them neatly and place them in a stack. I was down to my underwear,
and she told me that those had to come too. I was slightly aroused,
standing naked in front of this beautiful woman. She gave me a robe to put
on, which was light pink also. I must have given her a puzzled look,
because she made the comment that it was all they had. Taking my stack of
clothes with her, she then said that she would be back at 10:00, and I
should make myself comfortable and read a magazine or something. I decided
to look around the room, and walked over to the closet. I opened it up and
saw that there were nothing but women's clothes hanging there. Dresses,
skirts, and blouses. In the bottom of the closet were rows of very high
heeled shoes. There was a dresser next to the closet and I looked inside it.
The top drawer was full of bras and panties, all very lacy and frilly. The
second drawer was loaded with various other kinds of lingerie-teddies,
bustiers, stockings, garters, and corsets. The next drawer had several
styles of bikini bathing suits. They were just the styles that I liked to
see my girls wear, not much fabric. I admired the thong back, and was
hoping I would get to see one of these nurses wear it. I walked into the
bathroom and saw all kinds of lotions, creams, perfumes, sprays and makeup.
There were also depilatories, female razors, shaving cream, tampons, and
maxi pads.. I went over to the rack in my room and saw that all the
magazines were for girls too. Glamour, Cosmo, Seventeen. Great, I thought.
They must be short of rooms or something. This is definitely a girl's
room. I decided to pass on the magazine, and sat down on the bed. It
wasn't too much longer before the nurse came back in the room.
"It's ten o'clock. Time for your first session. Dr. Tetley will be in
shortly. Before she gets here, I have to apply your Sissy bracelet."
I had no idea what she was talking about, but it turns out that I
didn't want to know. The bracelet in question fastens around the base of
your penis. The bracelet has sensors that determine the tightness of the
bracelet. When the penis attempts to become erect, the bracelet tightens and
delivers a strong electrical current to the testicles and prostate causing
immense pain. The shock continues until the erection subsides. At the
bottom of the bracelet is a piece of hardened metal that reaches back and
fastens behind the testicles. The piece is then securely fastened and a
lock is placed on it to prevent it from being removed.
After she had the bracelet in place and locked, she started telling me
what it was.
"This bracelet will prevent you from obtaining an erection. Eventually, the
brain starts to associate pain with achieving erections, and makes erections
impossible to achieve even after the bracelet is removed."
She must have seen the look on my face because she said, "You are in a
sex offender's institution."
"Our female staff will do everything in our power to assist you in your
conditioning. I will demonstrate."
As she was saying this, she reached down and started gently caressing my
captive penis. She had her breasts right in my face. I was starting to
feel movement down below and was already dreading the coming pain. As my
cock started to grow, I felt an incredibly painful shock. My cock
immediately went soft.
"See what I mean? It is very effective." She said with a smile.
The door opened and an older but very attractive doctor walked in the
room. She had short brown hair and had a large smile on her face.
"Dr. Tetley, I was just demonstrating to Sam here the effects of the Sissy
Bracelet."
"Very good, nurse. Please get Sam's injection ready for his session." "Hi,
Sam. I'm Dr. Tetley. We are going to be spending a lot of time together in
the next few months, so it is important that we get along. These first
sessions are very simple. You receive an injection, and then you listen to
some music with your headphones. It's that simple."
The nurse started injecting the fluid into my arm.
"What is in the injection?" I asked innocently.
"Oh, not much. Just something to help you relax. It also has the effect of
making the recipient very open to suggestions. It is used quite frequently
with hypnosis."
I barely even heard the last few words that she said, as I was
struggling to keep my eyes open. I laid down on the bed, and was vaguely
aware of headphones being placed over my ears. I heard classical music
being played very softly. I don't remember much after that.
"He should be out for about four hours. Which tape did you use?" asked Dr.
Tetley.
"I started him with the Crossdressing/Excitement/Humiliation tape. It
repeats itself every five minutes, so he should hear it about forty-eight
times if he stays out for four hours."
"Did you give him his female hormone booster injection?"
"Yes, Dr. Tetley. First thing this morning. I told him it was an
inoculation."
"Very good nurse. Tomorrow morning, make sure he starts taking the
maintenance doses of estradiol/progesterone pills. Since we only have four
months with him, give him double the dosage. Tony will want to see results
within the four months. We will also increase the frequency of the booster
injections from once every three weeks to once a week." Said Dr. Tetley.
While they were talking, I was in my drug-induced trance. Because of
this, I was not aware the tape had subliminal messages on it. The tape's
message was this:

I am a sissy. I love the feeling of my legs and body being clean shaven. I
love the way pantyhose and stockings feel on my clean shaven legs. I love
wearing ultra-feminine panties, bras, garters, teddies, bustiers, corsets,
and high heeled shoes. I love wearing any type of feminine clothing,
especially very short skirts and revealing blouses. I love makeup of all
kinds, especially when it makes me look more slutty. I love having my hair
styled in a feminine fashion, and I want my hair bleached blonde. I want my
eyebrows to always be very thin and highly arched. I want my ears pierced
with large gold hoops. I want my fingernails to be an inch long and painted
bright red. I wish I had large, DD-cup breasts and will do whatever needed
to obtain them. The first week in every month is when my menstrual cycle
begins, and I must wear a tampon and a maxi pad at all times during that
week for maximum protection. Maintaining a feminine image will always
sexually arouse me, even though my pathetic penis will not be erect. I will
attempt to learn as much as possible about maintaining a feminine image.
Wearing traditional male clothes will create a feeling of intense
discomfort. Whenever other people see me in my feminine image, I will
remember that I was once a man and I will be deeply humiliated, but also
very aroused by this humiliation. Being aroused by my humiliation will
embarrass me even further. My penis is a useless piece of flesh, and I wish
I could have it removed. I want to be called by my feminine name, Samantha.
I am a sissy.

This tape played over and over while I was "relaxing". When I woke up,
the headphones were still on, but there was no music being played. I took
the headphones off and sat up. I felt a little woozy from whatever
injection they had given me, but I felt fine other than that. Some therapy
session that was. Ha! If I got to sleep through all the boring therapy
sessions, four months would go by in no time flat! If only I could get this
painful bracelet off my cock, this place wouldn't be so bad. Just as I
started thinking this, the door opened and two very beautiful nurses walked
in. They were wearing nothing but their bra and panties. One of them had
breasts so big, I thought they were going to fall out of her bra. They
instructed me to lay down on the bed and they started to take off their bra
and panties. I immediately started becoming aroused. Ow! I felt the sharp
shocking pain strike me and then my erection immediately withdrew. I was
trying to keep my eyes off of the girls to prevent the recurrence of this
pain, but it was difficult. One of the girls came over and straddled my
face and told me to lick. I had always loved eating pussy before, so I
hungrily began lapping. I started to feel my penis growing, and then felt
the accompanying pain. This was not going to be so fun after all. The
other girl had started fondling my penis with her hands. Then I felt her
soft lips close around the head of my cock, and I knew this was going to be
a long session. Arousal, pain, arousal, pain. I continued licking the girl
on my face and then I heard the girl who was sucking my cock say,
"I can't get his pathetic little cock hard. This little sissy is never
going to be able to pleasure me with that miniscule limp piece of sissy
flesh. He must be impotent. Good thing I brought my extender."
I felt something being placed over my penis. It was what appeared to
be a hollow cock. The girl on my face was rapidly approaching orgasm. I
felt her cum as she started convulsing and wrapping her thighs tighter
around my face. Then she climbed off. The other girl started mounting my
cock (or the extender). It was exciting me to watch her ride up and down,
and my cock started getting hard again. Pain. I had to endure this
arousal, pain, arousal, pain cycle until she came. I was so glad when they
finally put their clothes back on and left. I looked at the clock. It was
2:45. My original nurse brought my lunch and told me that my evening
session would begin at 8:00, but that I had to go to my aerobics class at
5:30. She told me to feel free to look around my room further. There was
nothing else to do, so I went over and picked up the first magazine I saw,
Cosmo. I started thumbing through the pages and I saw the beautiful models
in their trendy clothes. I wish I looked like that, I thought. Then I
caught myself. What am I thinking? I pushed that thought aside and started
reading an article about the new makeup trend coming out. I must have been
totally engrossed in my magazines, because I lost track of time. At 5:15,
the nurse came back in and told me I had to get ready for my aerobics class.
She went over to the dresser and pulled out a pink spandex leotard. She
told me to get out of my gown and put it on. I had never worn a leotard
before, and definitely not a pink one. I hesitated for a moment.
"Come on, we don't have all day." The nurse said.
I decided I better cooperate, remembering Tony's warning. I put the
leotard on. It didn't look very good, with my hairy legs, the unsightly
bulge around my crotch, and no breasts. I felt mild embarrassment wearing
this in front of the nurse, and could feel my face blushing. I still felt
sexy though, and really didn't know why. I went to my aerobics class and
they worked me harder than I had ever exercised before. I was sweating
profusely, and when we got back, the nurse supervised my shower.
"What hairy legs you have. I'll bet they would look much sexier if they
were shaved." The nurse said and then left.
I almost agreed with her, and then changed my mind. What am I
thinking? After I got out of the shower, I went to put my gown back on, and
it was gone! I guess the nurse had taken it to get it cleaned. I had no
choice but to wear the clothes in my closet. I reached in and pulled out
the least feminine of the panties and put them on. They were pink lace
panties with white bows at the top. For some reason I wanted to put them
on, so I did. I went over to the closet and pulled out the least feminine
blouse that I could. It was a white silk blouse and I pulled it over my
head.
8:00 rolled around and the door opened. Dr. Tetley and my nurse walked
in.
"You know the drill Sam. Same as this morning. A shot, and then the
headphones. Very nice panties, by the way." Dr. Tetley said.
The nurse put the needle in my arm and depressed the plunger. Moments
later, I was out again.
"Which tape this time, nurse?"
"This is the tape that alters sexual orientation. Won't he still be
attracted to women though?"
"The Sissy Bracelet will take care of that. Not only does it force the mind
to associate pain with erections, but it also associates pain with women
performing sexual activity. That is why you girls stimulate him at every
chance. The tape will reinforce that association. By the time he leaves
here, he will never again even look at another women for sex."
Did you see him reading those women's magazines?"
"Yes, I did. The mental changes that will take place will be very gradual.
Sam will not even be aware that he is changing. He will think they are very
normal. It won't be too long before he starts wearing all of the clothes in
his closet and dresser. Let's play the tape now. " Dr. Tetley said.
This tape was a little different than the morning session tape. Its
message played this:

I am a sissy. I love to suck cock. I love everything about the male
anatomy, but I especially love large cocks. I love to lick testicles. I
love to have a cock in my asshole. I love pleasing multiple men at the same
time. I love to stick my tongue in male's assholes. I love the taste of
cum. I have an incredible craving for cum. I must taste cum at least twice
a day, or I start feeling intense discomfort. I like cum sprayed all over my
face, but then I must lick it off so as not to waste it. I like well-built
men with large muscles, but I am not particular. I will suck any cock
placed in front of me. I love to deep throat cock. Having a cock in my
mouth or in my asshole is sexually arousing to me, and is the only way I can
achieve orgasm, even though my pathetic penis will not be erect. I wish I
could have my penis removed. I am a sexual submissive, and will do whatever
my male partners ask me to do. I am a cocksucking, cumslurping sissy whore.

The tape was played repeatedly while I was in my trance. When I woke
up, the headphones were still on, but again no music. The door opened, and
my two buxom friends from this morning entered. I silently groaned. A week
ago, confronted with the same situation, I would have been ecstatic. Now it
was somewhat of a mixed feeling. The same process was repeated as my
morning session. Arousal, pain, arousal, pain. The only difference was
that this session lasted longer because I had to get both girls off orally,
and then both wanted to get off on the extender. By the time they left, I
was completely exhausted and very sexually frustrated. I had been exposed
to some very sexual situations, and had not been allowed release. I looked
at my Sissy bracelet to see if there was some way for removal. It looked
pretty sturdy. The only way I saw to remove it would be with a blowtorch,
and I really didn't have access to or want to do that. I was starting to
get tired. Other than my drug induced trances (which didn't really count as
sleep), I had been awake since 6:00 am. I decided I better go to bed, since
it was about 12:45.
The next morning I was awakened at 8:00. Breakfast time. The nurse
had some pills for me to take. I didn't think much of it, thinking it was
something to calm me. Besides, what choice did I have? I took the pills
and the rest of the day shaped up pretty much the same as the day before.
The next two months were pretty uneventful. My sessions followed
basically the same format. The nurses tried to arouse me as often as they
saw me. I was controlling my erections much more effectively, and my penis
would only respond to very heavy stimulation now. I was proud of myself. I
was starting to wear all the clothes in my closet now. What else were they
there for? The only problem was this pathetic penis. It created a very
unsightly bulge in my skin tight skirts. The nurse showed my how to tuck it
back between my legs so that it wouldn't show, but I wish it wasn't even
there. I was even learning how to walk gracefully in my six inch stiletto
heels. I was just happy that I had such an appealing wardrobe to choose
from. Most women could only be so lucky.
I had also started shaving my legs. I couldn't believe how wonderful
these stockings felt on my smooth legs. I wish I had discovered this
before! The nurse said that if I wanted, she could arrange for electrolysis
sessions for my beard, legs, and underarms. I really didn't need it
anywhere else, as I wasn't very hairy. I eagerly agreed. If I could be
this smooth without all the work of shaving or depilatories, I was all for
it!
The nurse had been having me go to a tanning bed once a day as well.
I was golden brown all over my body except where my bikini bathing suit
covered. I had very dramatic tan lines where my bikini top and bottom
sheltered. The nurse told me that these tan lines would help me look more
feminine, even when I was naked.
I was learning a lot about makeup from my magazines. I got caught by
my nurse trying to apply makeup. She said it was only natural, and has
shown me the tricks of application. It makes me look so much more
beautiful! She also showed me some things about styling my hair. She said
that there was a salon on site if I was interested, and I was. For some
strange reason, I wanted my hair dyed to a bleached blonde color. We
visited the salon and I had my hair dyed and styled, my nails done, and my
eyebrows plucked. They also pierced my ears! They placed very large gold
hoops through my ears, just like I asked. I was really beginning to like
this place. Everyone was so nice.
The nurse also has been kind enough to help me lace up my corsets in
the morning. When I first got here, my waist was thirty-two inches.
Through my special diet, aerobics, and corset training, it is now
twenty-eight inches without the corset! I hope to have it down to
twenty-four by the time I leave here, even if I have to get liposuction.
For some reason, my hips had been growing larger. That made my waist look
even smaller, and I loved it. I want to look as feminine as possible, no
matter what the costs.
Maintaining this feminine image has been very exciting for me.
Although my pathetic penis is not erect, I have the same feelings of
arousal. I also get very humiliated when another person sees me dressed and
acting as a woman. After all, I am a man. This humiliation only excites me
more.
At the first of the month, I remembered that it was the beginning of my
menstrual cycle. I didn't want to bleed on my beautiful new clothes, so I
wanted maximum protection. I asked the nurse if it was ok to use a tampon
and a maxi pad, and she said sure. She even showed me how to use them. It
was very arousing to insert the tampon in my ass, it reminded me of a man's
cock.
I had been having dreams about men for the past month or so. Although
I haven't seen any since I have been here, they are all that I have been
thinking about. I had developed a very strong craving for the taste of cum.
I knew that the first man that I saw when I got out of here was going to get
one incredible blow job! That way, he would tell all of his friends how
great it was, and then I could have them all at the same time! I knew that
what I really needed was a cock in my mouth and a cock in my ass
simultaneously. One thing for sure, I needed a man, and I needed him now.
Not being able to taste cum is part of the reason why I have been feeling
ill lately. I told the nurse this and she said she would see what she could
do. I also asked her to stop calling me Sam and please start calling me
Samantha. It sounded so much better. The nurse left the room for awhile,
and came back in with a large dildo.
"Samantha, to get that cum that you crave so much, you are going to have to
learn to suck cock properly. If you don't do it right, then you don't get
the reward that you crave so much. I will help you learn."
The next three weeks we spent about an hour each morning and afternoon
practicing on the dildo. The hour in the morning was to teach me everything
that a man likes in a blow job and exactly how to do it. The hour in the
afternoon was spent performing anal training. The dildo was very realistic
looking, eight inches long and thick. By the end of our training sessions,
I was able to take the dildo all the way down my throat and get it
completely in my mouth. I could also take it and other butt plugs the nurse
brought in my ass. Those three weeks we had also spent some very intensive
conditioning sessions with the buxom nurses. My cock had completely stopped
responding to their stimulations, no matter how long they caressed, rubbed,
or sucked. To be honest, females didn't really turn me on. How could they
turn me on when they don't have what I really crave? Whenever I saw a naked
female, all I thought about was pain. I needed a cock, and it needed to be
filled with that sweet nectar called cum. I had also noticed that my
breasts had started growing. They weren't the D-cups that I wanted and
needed, but they were about a small B-cup. I showed the nurse my new body
parts, and she said that she had noticed. I was so proud! She brought me
some new bras that fit much better. After I told her again why I thought I
had not been feeling so well lately (I needed cum), she told me something
that I had been longing to hear for a long time now.
"You have been very cooperative throughout your training. Now that you have
learned to suck cock and take it in your ass properly, I am going to
introduce you to one of our male residents. His name is Michael and he is
very well endowed. I think you said you liked that, right? Freshen up your
makeup before he comes in."
"Oh yes, thank you nurse." I could barely contain my excitement as I
reapplied my lipstick and powdered my nose.
The nurse went and opened the door. A young man that I guessed to be
about twenty-five walked in. He was very striking. He had long brown hair,
and very wide shoulders. I guessed him to be about six feet tall and 225
pounds. He was very muscular, I could see that even through his hospital
scrubs. The nurse told me that he liked Sissy boys like me, that he was very
dominant, and that she hoped we had a good time. Then she left the room.
"Hello Samantha. I am Michael. Take off all your clothes except for your
stockings, garter belt, and heels. I understand this will be your first time
with a real man?"
I started taking off my clothes as instructed and nodded my head at his
question. He was taking off his shirt as well. I couldn't believe that he
was so muscular! He had a washboard stomach and very large pectorals. His
arms were as big around as my thigh! I was so excited right now that I could
barely contain my excitement.
"I might take it easy on you, or I might not. It all depends on my mood."
He was taking off his pants. When he pulled down his briefs, I
immediately started thanking the nurse in my head. He had a cock that put
the practice dildo to shame! It was about ten inches long, and very, very
thick. I could see the veins running up and down the shaft. And he wasn't
even completely hard yet! He came over and sat down on the bed.
"Come over here and get on your knees." He demanded.
Ah, the moment I've finally been waiting for. I finally get to suck a
cock. I grabbed his cock and was about to greedily start inhaling it.
"Not so fast Samantha. I want you to tongue my asshole first."
I really liked licking assholes, but I had been waiting so long to
taste cum. I guess I could wait a little longer. I started licking around
the edges of his asshole, and then slowly inserted my tongue into his
waiting anus. I noticed that his already enormous cock was showing signs of
appreciation for this tonguing. After about thirty seconds of this, his
cock was rock hard.
"Now you may worship my cock."
Eagerly, I licked from the asshole up. Pausing at the prostate, I
sucked there for awhile. Then I came further up and licked each testicle.
I took each testicle in my mouth and rolled it around gently with my tongue.
Michael seemed to appreciate it from the groans I heard. Then I started
licking up the underside of his gigantic shaft. I got to the top and I was
faced with what looked like a giant purple mushroom cap. It was now the
moment of truth. I was about to see if all my long training sessions with
the dildo had paid off. I started gently licking the base of the head. I
traced my tongue all along the underside of the head. Then I softly took
the head into my mouth. I sucked gently there for a little while, opening
my mouth and inhaling gently. As the cool air rushed over the head of his
cock, I heard him let out a sigh. Then I closed my lipsticked lips around
his cock and started taking the piece of meat as deep into my gullet as it
would go. I was moving my head around in a circle, just as nurse had taught
me. My nose was embedded in his tightly trimmed pubic hairs. I stayed there
for about ten seconds, and then had to come up for air. I took his cock out
of my mouth and saw that it had a reddish tint to it now from my lipstick.
Then I hungrily started sucking again. I was fondling his testicles with my
hand at the same time, taking care not to scratch him with my one inch
nails. He also liked it when I was massaging his prostate with the pad of
my fingers. I was very proud that I had taken all of his cock into my
mouth. He evidently liked the way it felt. After about five minutes of
sucking, Michael started moving his hips in rhythm with my bobbing. As he
started getting faster, I knew that he was about to cum, and that I was
about to receive my reward. I felt his body start to spasm, and then I was
rewarded with a rush of cum into my mouth. Parts of his load hit the back
of my throat, and I was a little disappointed that I wouldn't get to taste
it. There was plenty to taste in this load, however. I continued milking
his cock and sucking every last available drop. It was warm, and had a very
pleasant salty taste. No wonder I had been craving it. They should bottle
this stuff and sell it, I thought. I continued sucking on his cock, waiting
for it to soften. Even though my pathetic little cock was not hard, I was
really aroused. I felt as if I was about to cum myself. I didn't really
think that was possible, since this useless piece of flesh between my legs
no longer functioned. In my prior experiences with sex, after I came, my
pathetic penis got limp. I sucked his cock for another three minutes after
he came, and it still didn't get soft. Noticing my surprise, he said,
"I do not have a refractory period like most males. I can stay hard and
keep right on going. Now I'm going to take your ass. Get up on the bed."
I was sorry that his cock had to leave my mouth, but I was glad that it
would soon find another home in my body. I got up on the bed, on my hands
and knees. He went into the bathroom and came out with a tube of K-Y jelly.
He started smearing it all over his huge member, and then on my asshole.
"I hope you are ready for this you sissy bitch." He said as he inched closer
to me.
If I had been more ready, I would have started waving a green flag. I
moved closer to the edge of the bed. I felt his cock press against my
rosebud. It was much larger than either the dildo or the buttplugs, so I
knew that I was in for a ride. I felt him start applying pressure, and then
I felt the head of his cock enter me.
"Oh yes, what a tight man-pussy. It feels so good."
I let out a gasp. I can't describe in words the feelings of excitement
that ran like waves through my whole body. As his cock entered me deeper,
it was creating a delightful feeling on my prostate. Deeper and deeper he
went until I felt his balls start slapping me on the back of my thighs.
Then he would pull his cock all the way out of me, leaving me feeling a void
in my bowels. Then he would ram it home. It felt so good that I could have
stayed there receiving that cock for hours, but when he started pumping his
hips faster and faster, I knew the fun was soon going to end. Faster and
faster he rammed my ass, and then a very strange thing happened. I had an
orgasm! I didn't think it was possible since my little sissy clit couldn't
get hard, but I was definitely cumming. I was shooting a huge amount of cum
onto the bed spread. It just came in wave after wave. It must have had a
long time to build up in my balls since I had no release since I had been
here. Michael also started moaning.
"Ohh....I'm about to cum, Sissy. Turn around, I want to cum in your mouth."
He said as he removed his cock from my man-pussy.
As I was still recovering from the waves of pleasure, I quickly turned
around, as I didn't want to waste any of his sweet load. Eagerly I accepted
his cock in my mouth, not thinking of anything but tasting that salty
beverage. He spewed forth just as much cum in this load as in his previous
load, and I was very grateful. I milked his balls again just to make sure
that I didn't miss any.
"Very good job, Sissy Samantha. I will be bringing my friend back with me
tomorrow. We will indoctrinate you into the multiple partner scene. In the
meantime, you should clean up that mess that you left on the bedspread. I
wouldn't want you to waste any cum."
I realized that he was right. This was cum, and I longed for the taste
of it, no matter where it came from. I started lapping up my spent cum from
the bedspread and heard Michael say something about what a cumslurping whore
I was. I really didn't care since I was getting more of that precious
liquid in my mouth.
Michael came by on a regular basis now. I found myself looking
forward to his visits more and more. Sometimes he would bring friends, and
I really enjoyed that. More cum for me. Other times he would come alone,
and taught me the finer points of pleasing a man. I was really learning a
lot here, and I never wanted to leave. He brought two friends one morning,
and I knew that I was in for a special treat.
"Hello Samantha. You have been doing so well in your training here, that I
decided that a reward was in order. These are my two friends, Mark and
Jason. They have an attraction to sissy sluts like you too."
I didn't care what their names were, all I wanted was to see what they
had in the cock department. I was hoping they had balls full of cum, so
that I could get my fill for the day. I wasn't disappointed. They all
three got undressed and put me in the middle of their circle. I was in
heaven, with a cock in my mouth, and one in each of my hands. Then I would
switch. Then Mark started the fun. He walked around behind me and started
lubing up my man-pussy. Then he entered and started pounding away. It was
difficult for me to concentrate on sucking with this big cock in my ass, but
I did my best. I was also starting to orgasm just from sucking cocks.
Michael started getting jealous that Jason's cock was in my mouth, so he
pushed him out of the way and quickly filled my mouth with his cock. I
continued to arouse Jason with my hand while Michael's cock was in my mouth,
and Mark's in my love hole. They continued this cycle until each one of
them had cum in my ass, and in my mouth. It was a dream come true.
My days were mostly the same, with my routine therapy sessions,
sessions with Michael, aerobics, tanning bed appointments, taking my
"vitamin" pills, and salon appointments. I barely even noticed that four
months had elapsed. The nurse told me that as a present for me being so
cooperative, that they would provide breast augmentation at no charge. I
was so excited! It had been a lifelong dream of mine to have DD breasts. I
couldn't wait to show them off to all of my friends at home! I couldn't
wait to add to my perky but small B-cups. She also told me that the Sissy
Bracelet would be removed later that day. I didn't really care because I
never wanted to use this worthless piece of flesh called a penis again.
All I wanted was to feel other men's cocks deep in my throat or in my
man-pussy.
When the surgery was done, it took about 2 weeks for my recovery. When
I finally got to see my new mounds, all I wanted to do was show them off.
The doctor told me that he also enhanced my nipples by implanting a
splint-like apparatus that would keep them always erect and one inch long.
The nurse told me that it wasn't proper to show them to just anyone, only
those men whose cocks I wanted to suck or fuck. He said that he did
something to the tendons in my ankles to enable me to wear heels better. I
found out what he was talking about when I tried to step out of bed
barefooted. I experienced intense pain shooting straight up my leg. The
doctor just laughed. He told me that he had shortened my tendons to keep my
foot in a permanently arched position so that I could wear seven or even
eight-inch heels with no problem. The down side is that I must always wear
at least five inch heels or I would be unable to walk. While I was under,
they also injected my lips with massive amounts of collagen. My lips were
extremely full now, something the nurse said would help me with all of the
cocks I was going to suck. They also performed liposuction on my waist,
getting it down to twenty inches. That was even better than I imagined.
With a corset, I should be able to reduce that to sixteen inches or less. I
was going to be some specimen, DD breasts and a twenty inch waist. I would
be the life of the party! She fitted me with my new bras, which had
openings where my nipples were so that they would show through whatever
blouse I was wearing. I told the nurse that I wanted to show my
appreciation to the doctor personally. She went and got the doctor and he
came in with somewhat of a surprised look on his face. I asked the nurse to
leave, and then immediately unzipped his pants. I then gave him my first
blow job with my new lips! I think he really appreciated it, because he
told me that he would let me swallow his cum. I never wanted to leave here,
but I knew that outside I could find all the cocks and cum that I wanted.
The nurses helped me pack my things (they let me keep all of the
clothes) and then removed the Sissy bracelet. She told me that she thought
it would be quite awhile before I was ever bothered by that useless piece of
flesh, and that I should have it removed as soon as I got the chance. I was
in complete agreement. It really only got in the way anyway. She also gave
me a four month supply of pills that I should take daily to help maintain my
feminine appearance. There were also six syringes in the kit she gave me
that she said I should get Tony to inject once every three weeks. The nurse
told me that Tony would be here to pick me up in about an hour, so I should
freshen my makeup and get ready. I had been so busy with my sessions that I
had forgotten about him! I wondered if he would let me suck his cock.
Tony arrived, and I think he was very surprised to see me by the look
on his face. He barely even recognized me. We packed my things in the car,
and started driving back to my neighborhood. Along the way, Tony told me
that him and Marie had been spending quite a lot of time together. He was
waiting for a response from me, but I didn't care. I don't even like women.
Then he told me that he had a new job for me already lined up. I was very
grateful, since I could no longer perform the job I did prior to my rehab.
He also said that he had a place for me to live, rent free. He said he
would take me there just as soon as we made a stop somewhere. I recognized
the bar where we stopped. It was a bar where the Ciccio family hung out.
Tony grabbed my hand and brought me inside. All of my former coworkers were
in there-Paulie, Junior, Marty, and Peter. I got quite a few whistles
walking in the door.
"Hey Tony. Who's the broad with the big tits?" that was Paulie.
"Gentlemen, you are going to be surprised. This is the former Sam Jacobs.
You can now call him Samantha"
"Holy shit. I thought that was just a rumor, to prevent the cops from
looking for a body. You really did it?" Junior said.
"Not only did I do it, but Samantha has something to show you. Call it
appreciation for being such good coworkers. Samantha, show them your tits."
I remembered the nurse telling me not to show them to everyone, only
the people whose cocks I wanted to suck or fuck. I sure did want to fuck
them all though. I was embarrassed to be seen like this by all of my old
friends, but I really had only one thing on my mind. I unbuttoned my
blouse, took off my bra, and exposed my DD mammaries to my old group of
coworkers. Junior and Marty started laughing, but I think Paulie and Peter
were getting a little excited. Tony asked the group if they would like blow
jobs. They eagerly started screaming yes. Right there in the middle of the
bar, I started sucking each of their cocks. One after the other. Paulie
told me he wanted to titty-fuck me, so I let him. He shot all over my face.
Thirty minutes later, I was dripping with cum. I had five loads of cum
(Tony joined in) covering every part of my face. I went to work on licking
it all up, so it wouldn't be wasted.
"You really did a number on him Tony. Make sure you bring him around every
so often. He gives an excellent blow job." Peter said.
"Don't worry. She won't be very far away. I am taking her now to Joanie's.
She is going to live and work there. I will let Joanie know that you guys
always have free passes."
"Is that the whorehouse over on MLK?"
"That's the one. Let's go, Samantha."
While they were talking, I had been busy licking off the precious fluid
covering my face. I had heard Tony tell those guys that I was going to be
working in a whorehouse, and I was very excited. Where else could I find a
steady stream of guys that were only interested in sex? Well, that's
another story, but it would be a good place for me anyway. We arrived at
the house and Tony helped me unload my things. He introduced me to Joanie,
and I thought she was very nice. She told me that she had a large client
base that was interested in girls like me. She told me I could start
immediately. There was no rent here and food was provided, but I had to
service at least ten johns a day to earn my keep. She said my customers
would be predominately black, so I should be prepared for some large cocks.
She said this was not a high priced establishment, they charged twenty
dollars for a blow job and forty dollars for a fuck. I didn't think that
either would be a problem. The bigger the better, right?
My life follows pretty much the same pattern every day. I sleep until
about ten, wake up, exercise, take my pills, and go shopping. I come home
and start getting ready for the night's festivities around five, shower and
get ready, and then service customers until about twelve. Usually I have
not gotten my fill of cum yet, so I go out to the clubs after that and try
and suck one or two cocks. Then I come home, go to bed, and start another
day. What a life, I love it!


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