Hard Hal's Heaven and Hell
by
Pamela (
[email protected])
"What's the matter, Hal?" Debbie said. She was lying in bed naked
and Hal was above her futilely trying to get his limp member inside
her.
"Just a second honey, I know I can do it."
"You've been trying for ten minutes."
"I know, I know."
"I've got to get to my class."
"I know, just give me one more chance. I think it's getting harder."
Hal desperately tried to force his penis inside her and finally gave
up. With a loud sigh he rolled off her and said, "I honestly don't
know what's the matter. I really want to make love to you. I'm so
horny."
"I know, Hal. I believe you."
"I guess I need Viagra."
"Hal, you're only 36 years old. You definitely shouldn't need it."
"Maybe I have a medical condition."
"What about your beating off?"
"Beating off? What do you mean?"
"Get real Hal. All men beat off. I know you beat off sometimes."
"Well I have no problem doing that."
"So what's the problem when you're doing it with me?" Debbie said as
she got up and began dressing.
"Why do you have to go to class?" Hal said. He loved looking at her
full breasts, especially while she leaned over. He watched her pick
up her bra and then his favorite moment came when she captured her
breasts in it and clipped the bra behind her back. As always, he felt
a pulse in his penis. He wondered if his impotence problem could be
fixed merely by her wearing a bra while they made love.
"What are you asking? Do you have a problem with me going to class?"
"I mean, all of a sudden the last few months you have to go to your
exercise class."
"I just want to keep healthy and get a nice physique. I like the way
the workout makes me feel young and strong. What's the problem with
that?"
"Sometimes I think you're going out to have a rendezvous with
someone."
Debbie stopped what she was doing and looked angrily at Hal. "If you
say something like that again, I think you're going to seriously
regret it."
Hal shivered. "I'm sorry Debbie. I didn't mean that. I do trust you."
Debbie continued getting dressed. When her bra and panties were
covered over by her gym outfit, Hal felt disappointed. It was that
way every time. He so enjoyed seeing Debbie being feminine in her
underwear.
"I'll never understand why you bother to work out when nature
doesn't really intend for you to get bulging muscles. Not like mine
or men's for that matter."
Hal knew he was being provocative. Sometimes he felt that Debbie had
a place inside her mind that he was never allowed to know. Despite
his best effort at self-control he couldn't resist trying to catch
her by surprise and maybe get a glimpse of the secret place.
Debbie approached him with a strange look on her face. Ok, he
thought to himself, now I've got this shit to deal with. When will I
ever learn?
Silently, Debbie rolled up the sleeve covering her right arm and
made a muscle. Her biceps literally popped up out of her arm and
rigidly knotted up. It was much bigger than Hal had ever seen it
before or even imagined she could acquire.
"Go ahead and touch it Hal," Debbie said and Hal gently laid his
hand upon it and stroked it. It was like granite.
"Let's see yours Hal." Debbie said.
"Honey, we don't have to go through this. I don't want to make you
feel bad."
Debbie laughed. "Feel bad? Hal, you must be living in a fantasy
world. Let me feel your muscle."
"Fine," Hal said. He pulled up his shirt sleeve exposing his upper
arm and flexed his arm making a muscle.
Still laughing Debbie said, "I don't even see a bulge Hal." She
touched his arm and said, "gosh, it's soft like a girl's arm. I
figured you were weak, but I had no idea you were this weak."
"Look Debbie. I haven't had much time to exercise and I've just
gotten a bit out of shape. Don't worry about it. I'm still stronger
than you."
"How much can you lift? At the gym I'm up to 140 pounds."
"What do you mean by lift?"
"A barbell weighing 140 pounds. I can lift it straight over my head
from the ground."
Hal felt a stab of worry in his chest. He knew he'd have trouble
lifting 50 pounds. How had things changed so much? He remembered that
when he was in his early twenties he was as strong as the other guys.
"How much Hal?"
"OK Debbie. I'm sorry for what I said. It is chauvinistic. Maybe I
need to work out also. Sort of regain my former fitness."
"Hal, I don't mind how weak you are. Just don't interfere with my
interests. OK?"
"Maybe it has something to do with me being impotent."
"Like what?"
"Maybe I'm sensing that you're less feminine as you get more muscles."
"So you're blaming me for your impotence? That's a neat one."
"No, I'm not blaming you the way you mean. It may be a very subtle
thing."
"Look Hal. I've got to leave in a few minutes and I don't have time
to listen to this."
"But it could be true."
"Then you'll just have to get used to it."
"So what you're saying is that it's OK with you if you're becoming
strong undoes my subliminal desire to be attracted to you as a woman?"
"Hal, I know how your eyes follow my body around when I'm dressing.
You obviously see me as all woman."
"That's just at one level."
"Hal, you're starting to sound like a little whiney girl."
"Hey, that's not nice. How can you talk to your husband that way?"
"Don't act like a little girl and I won't call you one!"
"Debbie!"
"Hal!"
This was turning into an argument that neither of them wanted to have.
"I'm sorry Hal, I didn't mean to be so cruel, but there is some
truth to what I was saying. Isn't there?"
She came over to him. He was still naked and she put her arms around
him. Whispering in his ear she said, "you're weak, much weaker than
I. You can't get an erection. It's almost as if you had a vagina.
It's like there's nothing there. No manhood."
Hal felt his penis getting hard. It was shooting up a bit. From the
angle Debbie was sitting she plainly saw what was happening.
"I think it's safe to say that I've become the man of this family."
Hal's penis became rigid. "And since I'm the man and you're the girl
its not smart for you to give me a lot of lip since I'll have no
choice but to hurt you until you cut it out."
The degree of hardness in his prick became so intense Hal thought it
might cause a rupture in the muscles that kept it up.
"Well look at that," Debbie continued in a soft voice next to Hal's
ear. "It's hard. Boy is it hard. It's Hard Hal who's going to be my
obedient and sweet little girl wife. Isn't she?"
"Debbie!" Hal said in a contorted passion. Debbie stood up and
looked down on Hal and his monster erection pointing straight up in
the air.
"I see the answer to my question right there," Debbie said and
touched the tip of his penis with her finger, "and with an
exclamation point no less."
Debbie laughed at her joke and said, "unlike you're phony bravado, I
am stronger than you, a lot stronger, and with that strength comes
the simple fact that I don't have to take the feminine role in our
relationship any more if I choose not to. So here's what Hal. I'm
going to my exercise class now. I'll be back in two hours. While I'm
gone you're to do the laundry. The soap is in the shelf above the
kitchen sink. I know you've never done it before but you can figure
it out. The machines take quarters and dimes that I keep in a jar on
the counter. Oh, and of course you need to wash my bras by hand. In
fact, that gives me an idea." Debbie went to the dresser, opened a
drawer and took out a white bra and panty. "Just to help remind you
who's going to be the man in our family and who's going to be the
girl, you can put these on. We'll figure out some other clothes
later. I want you to fit my idea of a wife - I want you sexy, gentle
and available. Got to go now." Debbie abruptly turned and headed to
the door. Just before she left she said, "and when I get back, I
might want to have my way with you. So be cute and inviting."
***
Hal starred at the bra and panties Debbie had given him. The bra was
one of her older ones. He tried going back over in his mind the
sudden series of events that left him holding this bra and panties
with instructions to wear them. Everything had developed so fast it
was as if Debbie had planned everything. But then again, it was he
who was impotent; it was he was arrogant and chauvinistic.
He put the bra and panties aside and got dressed in his own clothes
and emptied the clothes from the laundry hamper into a laundry bag
being careful to separate out Debbie's bras. There were six of them.
One of them was a sports bra. Carrying the laundry bag he headed to
the laundry room downstairs in the basement of the apartment
building. While waiting for the elevator his cell phone rang and he
saw that it was Debbie calling.
"Hi, what's up?" Hal said.
"I forgot to mention that you need to wash my bras with Woolite.
It's under the sink. Then hang them up to dry on the rack. OK?"
"Sure, no problem," Hal said tersely.
"Are you wearing my bra and panties?"
"No, not exactly."
"That's not good Hal. Why not?"
"I didn't think you were serious."
"I am serious. I want you in a bra and panties when I come home."
"Debbie!"
"What's it going to be Hal?"
"But Debbie, it doesn't make sense."
"You will have the bra and panties on when I get home? Right?"
"OK, Debbie. Just this once I'll give you the benefit of the doubt
and wear it."
"It won't just be this once. It's going to be whenever I want you
to, which might be always. I haven't decided."
Hal felt his penis rising. "OK, whatever. Just don't make fun of me."
"Hal, if I want to make fun of you I will."
Hal felt strangely sad and confused. He wanted to curl up into a
ball and sleep. "OK Debbie. See you later."
"In my bra and panties?"
"Yes, Debbie."
"Bye Hal."
"Bye."
The elevator came and Hal went down to the laundry room that was in
the basement of the apartment complex. He couldn't recall ever
feeling as strange as he felt then. It seemed like the ground was
shifting underneath him and he didn't know where he might end up
falling.
***
When he entered the laundry room he saw that Lila was there. She and
Brock were his next door neighbors. Occasionally Hal could hear
sounds of their lovemaking through the thin apartment walls. Brock
was tall and hard edged and worked as a lineman for the telephone
company. Working outside kept him well tanned all year round. In
contrast, Lila was thin, pale but very pretty as far as Hal was
concerned.
"Hi Hal," Lila said while folding some clean and dry laundry.
"Where's Debbie? I've never seen you doing the laundry before."
"It's my first time believe it or not."
"Wow, Debbie sure treats you well."
"I guess I have been spoiled by her. Anyway, it looks like I'm in
charge of the laundry now."
"Did something happen?"
"Oh nothing really. She had to go out to her exercise class tonight."
Lila was a gentle and feminine woman. Hal watched her hands
delicately and girlishly fold the laundry. Her nails were perfectly
done. She was wearing a sleeveless pink blouse and it was clear that
unlike Debbie she certainly hadn't even a hint of a muscle in her
thin arms. Hal had always liked Lila and wished he had gotten to know
her better. It was mainly Debbie who spoke to Lila and she rarely
shared with him whatever she gossiped about with her.
"How's Brock?" Hal asked.
"Oh, OK, I guess. He's pretty constant." She said this with a slight
trace of resignation that Hal picked up. One time Debbie had been mad
at Brock for something he had done to Lila, but Hal couldn't remember
what it had been.
Lila looked off into space and then said to Hal, "you're a man.
Maybe I need a man's perspective on things."
"Sure, Lila, I'll be happy to give you my two cents."
"You know Brock is sort of a tough guy you could say."
"Tough?"
"Yeah, he kinda doesn't give me much room to ? I don't know ? maybe
do what I want to do. It's sort of always what he wants."
"That's too bad," Hal said.
"No, I don't want to give you the wrong impression. I do love Brock.
It's just... Tell me, do all men have to be so in charge as far as
the you-know-what goes. I feel embarrassed telling you this, but I
think you're different from Brock."
Hal blushed a little. He felt compassionate toward Lila. "Don't feel
embarrassed. I'm happy to be a sounding board."
"Well it's just that, in bed, do all men have to be in charge? Am I
being too forward?"
"No, not at all."
"Thanks for saying that," Lila said and smiled.
"Let me answer your question. No, I think there are plenty of men
who don't have to control things in bed. I know I don't."
"Really?" Lila said with her voice conveying discouragement.
"Does he hurt you?" Hal said feeling bold.
"No, well not exactly. Just once. I feel so embarrassed."
"You poor dear," Hal said. He wanted to walk over to her and hold
her but couldn't find the nerve, thinking it might be misinterpreted.
Hal saw a tear forming in Lila's eyes. "I'm happy to listen, if you
want to talk. Has Debbie been someone you can talk to?"
Lila regained her composure. "I like Debbie but it's not because
we're confidants. She's so self confidant, so assured of herself.
I've liked sort of feeling strength in her that I know I don't have.
If I did, I think I might have left Brock. There I go again, I'm
sorry."
"Don't be sorry," Hal said tenderly. This time he did go over to her
and gently put his arm around her.
There were many more tears in Lila's eyes. She sniffled and said, "I
will tell you about Brock and me. I know I can trust you. You see one
day after we were married about a year he said our sex had to be
better than it was. He wanted to have me anyway he wanted. Well what
he really had in mind then was entering my rear. Are you sure this
isn't too embarrassing for you?"
"No Lila. You're making me cry inside. You're such a sweet woman. Go
on."
"One day he forced me to lie on my stomach, then had me stick my
rear end in the air and he came at me from behind. When it started to
hurt I resisted. He got angry and then the next thing I knew he
punched me hard and gave me a black eye. It hurt like crazy and I was
so scared I basically just let him do whatever he wanted with me. He
got himself all the way inside me, had his fun. It hurt at first then
stopped I guess. I cried the rest of that night. I thought of calling
the police or any one else who might listen. But the next morning
Brock danced around the apartment completely happy with himself, like
he had no guilt what so ever. He did say he was sorry that he had had
to hit me, but he also said that it was great that I finally
understood what he was entitled to as my husband. I was so confused I
didn't do anything. The black eye healed, and ever since, and it's
been three years, he always just tells me what he wants and I do it.
He puts his thing anywhere he wants whenever he wants. He's really
quite powerful. With one finger he can hold me down. Lately he's
gotten me into giving him constant blow jobs. During dinner, during
breakfast. When he comes home. Half the time he cums on my face or on
my hair. Sometimes I feel like I'm drowning in the stuff. All the
time I'm blowing him I'm wishing I had been a lesbian so I wouldn't
have ended up with a Brock in my life."
"Oh my God," Hal said, utterly shocked, but not just by what she was
saying. He felt elated inside that she could trust in him so much
that she would say the most personal and intimate things to him. She
must have had him on her radar screen for a long time. He wiped away
a tear of his own and said, "sometimes through the wall I can hear
you having sex. I'll never be able to hear it again without my heart
going out to you. Please Lila; if there is anything I can do to help
you, you have to let me know." Hal's eyes teared up again as he said
this and Lila saw it and they hugged for a minute.
"I better get back to Brock. I hope we can talk again."
"We must," Hal said.
"Bye."
"Bye."
Hal had a hard time concentrating on doing the laundry after Lila
left, but he finally got it done. Neatly folded he brought it
upstairs to the apartment. He then washed Debbie's bras in the sink
and hung them to dry. When he was done he saw by the clock that
Debbie would be home soon. After debating what to do for a few
minutes, he finally decided he would take the path of least
resistance and put on Debbie's bra and panties, and then put his
shirt and jeans over them.
When Debbie came home she had the relaxed and invigorated look of
someone who had been working out hard. "How's my cutie?" she said.
Hal couldn't remember her ever addressing him like that before.
"Cutie? Just fine Debbie."
"I had one fantastic workout tonight. I finally broke the 150
barrier. I was so pumped!"
"Great!" Hal said with feigned enthusiasm. 150 pounds. The thought
of lifting that much weight made his arms hurt. He doubted if he
could even lift one end of the barbell off the ground.
Debbie walked into the bedroom, checked out the clean laundry and
then inspected her bras drying in the bathroom. "Very good Hal." She
went to her bureau and took out a white slip. "I want you prettier
Hal. Wearing a bra and panties under your shirt and jeans sort of
defeats the purpose for me. Put on this slip." She handed it to him
and continued on into the bathroom to take a shower.
Hal ran after her. "Debbie. Wait a minute."
"What Hal? I'm all sweaty I need to shower."
"You've obviously been doing some kind of plotting about all this
stuff."
"Stuff?"
"You know. Making me dress up. Like all of sudden you just decided
all this. I don't believe it. I think you've planned this, and I want
to know why."
Debbie looked at him. "Put the slip on and we'll talk after I get
out of the shower."
Hal felt hot in his face, but said, "OK."
Debbie went into the bathroom. He wondered what she was going to
say. He took off his shirt and pants and put the slip on and lay on
the bed. He could hear the water running in the bathroom. What was he
doing in a bra, slip and panties? It was crazy. Debbie had no right
to do that to him. He thought he had better take off the clothes and
confront her. Don't let it become a precedent. Through the wall he
heard the sound of a bed rocking. Then, very muffled he heard what
could have been Lila's voice saying, "gentler Brock. Not so rough." A
minute later there was a kind of yelp that was distinctly Brock's
voice.
Poor Lila, it was terrible what was happening to her. The water
stopped in the bathroom and Hal decided he would stay as he was.
Debbie came out of the bathroom naked and said, "that's a lot
better. You have a decent figure. A bit skinny I think. We need some
hips and boobs I suppose. But you do have a cute little butt."
Hal felt a little pulse in his penis. He watched as Debbie put on
panties and then a man's "wife beater" style undershirt that she took
from Hal's drawer.
"I didn't know you wear my undershirts," Hal said.
"All the guys wear these at the gym. I think they're nice for
showing off muscles."
Hal rolled his eyes and shook his head. What's next he wondered?
"Those hairy legs have got to go." Debbie said.
"You said you were going to confess to me about your planning all
this."
"Oh Hal, you're so dramatic. Look. I've been thinking that I like
men so why not get some thrills sort of acting like I'm a man. And if
I'm going to be the man, then it fits in well if you're the girl.
Anyway, since you're so feminine and powerless like a girl, I think
it works out well. You can think of me as a latent homosexual if you
want."
"This doesn't make you bisexual Debbie. Everyone has homosexual type
fantasies from time to time."
Debbie looked at him. "You fantasize about men?"
"This isn't about me."
"But it is about you. I want you as a girl and as luck would have
it, I can get what I want. I suppose if it's of any help to you, you
can fantasize about me being the man you've always wanted to have sex
with. Now come with me. First on the agenda is, I really need to get
rid of your leg and chest hair, then I'm going to fuck you."
Debbie went to the bathroom and Hal stayed put on the bed.
"Come here," Debbie said in a sharp voice and Hal got up and went to
the bathroom. He saw that Debbie was holding a bottle of Skintimate.
"Take off your slip and put your leg on the counter." Hal did like
she said and Debbie covered his leg with shaving cream.
"I can't believe you're doing this," Hal said.
Debbie ignored him, got her razor and began shaving his leg. "I
can't let you do this," Hal said.
Debbie laughed slightly. "Hush Hal, this won't take long.
Fortunately you're no gorilla."
Hal acted as if to take away his leg and Debbie gave him a sharp
look and he stopped. Suddenly Hal collapsed to the bathroom floor. "I
don't like what you're doing. I don't like this game. You've got to
stop."
Debbie stood over him holding the razor. "You're getting shaving
cream on the floor Hal. Get up now. We can either do this calmly, or
we can do this in a very unpleasant way."
Hal ignored her. "Hal?" Debbie said.
Hal looked up and just as he did so she punched him hard in the
face. He then struggled to his feet with tears pouring from his eyes.
While the pain coursed through his head he remembered what Lila had
said about how Brock had punched her. But this was too fantastical.
It was monstrous.
"Get your leg up," Debbie said and Hal put it back up. With his leg
propped up on the counter, the mirror reflected the fact he had an
enormous erection again. It was pointing up toward Debbie.
"You do have very pretty legs, Hal. Your skin is young and smooth
and your legs are very shapely."
She resumed shaving him. Hal's head hurt and though he fought back
tears they kept on coming. He felt like a little child. In the
morning he would have quite a shiner.
"We'll take care of that," Debbie said indicating his penis, "after
I'm done shaving you."
Debbie worked methodically and quickly and before long both of Hal's
legs were shaved and smooth. They looked pale in the harsh light of
the bathroom. Debbie then put shaving lotion on Hal's chest and
shaved it free of hair.
"I almost forgot your underarms," she said, and put some shaving gel
in his arm pits and shaved them bare. When she was done she said,
"now lie down on the bed," and Hal followed her instruction without
resistance. While he lay on his back wearing bra and panties, Debbie
pulled his panties down. She scowled at him and slightly raised her
fist in a threatening manor and Hal's penis which had been half erect
grew until it was straight up. Debbie grabbed the end of his penis
and pushed it up against her vagina so as to lubricate both of the
organs. Then she mounted Hal. Her hands pinned his hands down to the
bed.
"Now I fuck my girl," Debbie said and forcefully moved her hips up
and down forcing his penis inside her. Hal looked at her impossibly
large, hard knotted biceps as she pinned him to the bed. She pushed
down so hard he couldn't move anything above his hips.
"I fuck my little girl into oblivion," Debbie said with growing
excitement. Hal's penis was beyond stiff, if was a steel bar. "I fuck
her, I fuck her," Debbie said rhythmically and then reached orgasm
and her body shuddered over Hal's. When she was done, she rolled off
him. While it had felt very good, Hal was still hard as a rock and
far from having reached a climax.
"What about me," Hal asked.
"I'm tired," Debbie said and moved over to her side of the bed and
shut out the light.
"How can you not care about me?"
"Welcome to the club Hal. Now you know how girls feel."
"I'll get blue balls," Hal said trying not to sound like he was
whining.
"Balls Hal? You have balls?" Debbie laughed to herself in the semi-
dark. "Balls, that's a good one."
Hal cringed. Afraid to annoy her and risk another punch, he went to
the bathroom and took care of himself. Somewhat to his consternation,
while he manipulated himself he found himself admiring the way he
looked in the bra. As he was cuming he found himself thinking of both
Lila and Debbie. After he cleaned up he sat on the closed toilet lid
for a long time going over in his mind the tumultuous events of the
evening. Clearly his life had changed. His marriage had changed. How
had he missed so many signals that Debbie was becoming the man in
their relationship? Hal took off the bra, finished his ablutions and
went to bed. On his side of the bed he saw a silky, pink gown lying
on the coverlet that Debbie must have put there.
Without looking at him Debbie said in the semi-darkness. "Put on
your pretty gown."
Resigned to his fate, at least for this night, Hal but on the robe
and climbed into bed. The robe smelled of a sweet delicate perfume.
Hal felt enveloped by it. He said, "do you still love me Debbie?"
He felt Debbie's hand touch his thigh and squeeze it gently. "Of
course I do, you big baby."
Hal didn't know if he should feel happy or sad by the answer. In a
short while he fell asleep.
***
The next day when Hal looked in the mirror he saw that he had quite
a shiner. Debbie noticed it also when he came to the kitchen for
breakfast. He was wearing the pink gown and pink velvet slippers with
a little bow that Debbie had also left for him to wear.
"Oh my god, Hal, did I do that?"
Without saying anything Hal thought that that was a fairly dumb
thing to say.
"I feel so bad Hal. Can you ever forgive me?"
Debbie's contriteness was confusing since it wasn't expected.
"Sure Debbie. I just hope that you don't ever want to hit me again."
Debbie came over to him and smiled at him. "I never want to hit you.
You know that don't you?"
"Yes."
"Good. I hope that black eye doesn't hurt you too much."
"It's just a little sore, but nothing that I can't get over."
"You look very pretty in the gown Hal. Pink suits you."
"Thanks," Hal said wondering if that was what he really wanted to say.
"How do the slippers fit?"
"Not bad."
"You look absolutely hot!"
Hal smiled coyly.
"Come, I want a quickie before work," Debbie said and she took Hal
by the hand and dragged him back to the bedroom.
"C'mon Debbie, I'm only half awake," Hal protested.
Even though she had already dressed for work, Debbie took off her
blouse and suit pants. "This won't take long. Lie on the bed."
Hal lay down and Debbie climbed on top of him. Hal took in the view
of her breasts held in a black silky bra and felt a slight erection
starting. Debbie yanked his gown up, pulled down his panties until
they came off one of his legs. She made no attempt at being gentle.
"I need you hard NOW Hal," she said sternly and held a fist over him
causing his penis to immediately harden.
"Good girl," Debbie said. His penis was stiff enough now for her to
impale herself and she did. As soon as she got his penis in her she
sat up on her haunches and pumped up and down rhythmically. It didn't
take her long until she was shouting in ecstasy and like the night
before she came forcefully. Barely a minute after she had orgasmed
she jumped off him, leaving him lying on his back with his erection
pointing to the ceiling.
"Man that was great honey. Yum. I've got to straighten myself back
up and get to work. Bye."
"But," Hal said.
"But?"
"But what about me?" Hal tried to keep his voice calm and not whiney.
"You're job is to be available for my pleasure. We discussed that
yesterday. When I come home I wouldn't be surprised if I need you
again. We'll see."
Debbie put on her blouse and pants while he watched her.
There was a lot he wanted to say but said nothing.
"There's just one more thing Hal."
"What's that?"
"As long as I'm home I want you dressed as my girl. That means bra
and panties, slip, and I'll point you to some old dresses of mine
that you can wear. I also want your pretty legs in pantyhose. I have
some extra in my drawer you can put on. The shoes might be a problem.
I'll look into getting you some. You can wear the slippers anyway."
Hal shook his head in disbelief. "You mean I'm going to be dressed
like a girl all the time from now on?"
Debbie leaned down close to Hal and said in a quiet voice, "Hal, how
can I say this delicately. Let me see." Suddenly she laughed and
said, "I think people would call you my bitch now. You're my bitch,
Hal. I want my bitch in a pretty dress, so my bitch is going to be
wearing a pretty dress. Got it? Comprenez vous?"
Hal nodded his head slowly. His penis was rigid and begging for
attention, but Debbie was clearly not going to be bothering with it
any more. "Bitch?" Hal said.
"Bitch," Debbie said. "When I'm not here, I don't give a rat's ass
what you do. But the moment my key hits the lock I expect to open the
door to my pretty girl Hal. I want you as my red hot bitch."
"Uh, huh," Hal said.
"Now, I'm going to work. You can house clean and make me a nice
dinner when I get back."
"OK," Hal said.
"I want you to be pretty. Work on it Hal. There's a ton of makeup in
the bathroom. You can go shopping for some sexy outfits. Whatever it
takes. I want my girl to be pretty."
"OK."
"Good," Debbie said and she finished getting herself ready for work
and left the apartment.
Staying at home was routine for Hal. He was self-employed as a
health care agent, devising health plans for medium to small size
businesses. It paid modestly and with Debbie's salary as a contract
specialist for an architectural/engineering firm they had enough to
live reasonably well.
Hal cleaned up the breakfast dishes and when he was done he put on a
CD of Mozart arias and reflected upon what he ought to do about being
"Debbie's bitch." Too bad he couldn't talk it over with Lila. She'd
probably understand what he was going through and offer him some
comfort. The conversation with her in the laundry room had been
magical. If he didn't watch himself he'd probably fall in love with
her.
On the other hand, he did love Debbie, and for the same traits that
Lila had described about her. She was strong, confidant, direct. Even
honest. Yes, Debbie was very honest and he always knew where he stood
with her. She was also very sexy; except he wasn't so sure he liked
her new found musculature... Well he wasn't totally sure about that.
There was something exciting about her physical strength. He even
felt proud that he was married to someone who had the guts to
accomplish whatever she set her mind to doing, even if it was
becoming a bodybuilder.
In an hour Hal snapped out of his reverie and went to his computer
to see what work he had to do. Nothing. It was a slow time of the
year. He could try and make some new contacts or just relax. The
thought that Debbie could appear at any moment, gave him anxiety and
he decided he'd be a lot more relaxed if he just got dressed like she
wanted and then he could forget about it for the day.
He looked through the few dresses Debbie had indicated and picked
out a turquoise one. It had a full skirt, and in fact he noticed that
all the dresses had full skirts. Donna Reed. He was going to look
like Donna Reed, he chuckled to himself. He put his bra back on and
panties. He took pantyhose out of Debbie's drawer and put them on. It
was not hard to do, since he had watched Debbie do it so many times
that he had the whole procedure memorized. He felt proud when he
stood up and saw they were on without any twisting.
Next he donned the slip and finally the dress and then put on the
slippers. In the bathroom he found Debbie's makeup and put a little
on. He didn't know what he was doing, but it seemed like fun. The
shiner was very visible and he tried putting some powder over it. The
parallel between his shiner and Lila's seemed eerily similar. He
hoped he would run into her again and maybe he would be as courageous
as she and tell her the story of how Debbie had punched him. The last
thing he did was put some perfume behind his ears and on his neck.
His erection from the morning had subsided after Debbie had left and
so had the pain in his balls. While getting dressed he noticed an
erection forming again. There wasn't much room inside the pantyhose
for that, but by a little adjustment it seemed to work. He took a
long look at himself in the mirror. He had straight hair that, after
it grew out, could easily be made to be feminine. He was surely flat
chested and his butt was not a woman's. Still all and all, he had a
sort of delicacy, a slight softness in the way he moved and looked
that said that he was at least part way a girl. Maybe it was
something that Debbie had sensed a long time ago.
One thing was very clear, and that was by asserting his manhood to
Debbie he only accomplished the exact opposite: it exposed to the
light of day exactly how helpless he was in the face of her strength
and personality. He saw that he had three choices in front of him. He
could try and fight Debbie, escape the apartment for good, or else
succumb to being her "bitch". He thought again of Lila. She had been
faced with the same three choices also, and today she lived to
satisfy Brock.
Hal decided that maybe there was a fourth route: use reason to
undermine Debbie's control. As soon as she came home from work he
would see if this worked.
***
"Debbie, I don't think I can live under these circumstances," Hal
said that night while he was serving Debbie dinner. He was wearing
the turquoise dress with an apron over it. Debbie had insisted he
wear the frilly apron to make sure he didn't soil the dress.
"Come over here Hal," Debbie said nonchalantly.
Half protecting his face with his hands, Hal came over.
"I'm not going to hit you Hal," Debbie said laughing. "Sometimes
you're so cute. No, what I want to point out to you is this."
Debbie lifted up Hal's skirt and pulled down his panty hose. Then
she made a fist and acted as if she was going to strike him. Hal
instinctively cowered and as he did so he felt an erection coming on.
Debbie laughed gaily and pulled his pantyhose back up and resumed
eating her dinner.
"That's one reason why you'll never be going anywhere. But Hal,
you're not a prisoner. You can go anytime."
Hal didn't have much appetite for the fish he had broiled. He gave
himself a small serving and sat down to eat it.
"I want you more feminine," Debbie said after awhile. "You need to
grow your hair out and wear some jewelry. You can wear my pearl
necklace and we'll have to get your ears pierced. This weekend I'll
take you."
***
The days went by. On the weekend, as promised, Debbie took Hal to a
jewelry store to get his ears pierced.
"Gold studs or silver studs?" Debbie said repeating to Hal what the
young girl behind the counter had asked him.
"What's the difference?" Hal said.
"You'll have to excuse him," Debbie said conspiratorially. "Hal, one
is gold and the other is silver, it's not complicated."
"I mean I don't understand about studs," Hal said.
"What's there to understand?" Debbie said, "they first put studs in
until the wound heals."
"Wound?" Hal said nervously.
To the salesgirl Debbie said, "he's like a twelve year old girl. You
have to spell everything out for him. Sometimes Hal you make me
wonder if you even have enough smarts to be a girl."
Under his breath Hal said, "you're showing off in front of her. I
don't see why you have to be so mean to me."
"He'll take gold studs," Debbie said and to Hal she said, "sit down
here and let the girl insert them."
Hal sat down and the girl came over with the piercing machine. She
couldn't have been more than eighteen, and Hal wondered if she really
knew what she was doing.
Hal had a terrified look on his face and Debbie took his hand.
"Mommy will hold your hand while the lady pierces your ears. Try and
be a big girl and sit still for her." Debbie laughed at her own joke
and Hal could see from the expression on the girl's face that she
regarded the two of them as nuts.
It took just a few moments and the studs were in his ears. The girl
repeated the instructions for cleaning them. While he looked in a
mirror at what she had done, Debbie was telling the girl, "he's my
bitch. Sometimes a pain in the ass, but usually he's quite sweet and
well behaved."
Hal saw the girl shake her head. To Hal Debbie said, "go look around
the shop and find yourself a pretty pair of earrings to wear after
the studs come out."
Hal stood up and wandered around the display cases looking. He saw a
pair of simple, dangly earrings and pointed them out to Debbie. She
took a look at them and said, "no Hal. What about these cute ones
here. See the little ballet slippers dangling on the end of little
gold chains. They'll be very cute on you."
"I thought you said I could pick them out?"
Ignoring him, Debbie told the sales girl that they would take the
ballet slipper earrings and Hal swore under his breath and backed
away.
On the way home Hal said, "Maybe you can beat me up or make me have
sex with you any time you want and maybe I'm not able to leave you
but..."
"But what Hal?"
"But I don't think that public humiliation should be part of it."
"You don't think so?"
"No I don't. And I really don't understand how you would even want
to humiliate someone you say you love."
"Hal, I would never want to humiliate someone I don't love."
"What does that mean?"
"It means that because I love you, I'll always be there to protect
you when you're humiliated. You see, my love becomes the strongest
when I'm there for you while you're being humiliated. Others are
looking at you as being humiliated, but I'm with you. I haven't
abandoned you. I'm not with them."
"That's so convoluted Debbie. I don't understand anything you're
saying."
"Its no more convoluted than your being Hard Hal. Explain that."
Debbie, of course was right. Hal wondered if a philosopher sometime
and someplace had ever said something like "an erection is worth a
thousand words," because for Debbie and him it could not be more true.
***
On Wednesday, one week after he had first done the laundry, he again
ran into Lila in the laundry room. Debbie had gone off to her class
and she had given him the same instructions as the week before: do
the laundry and wash her bras. Hal was overjoyed that Lila was there
and by the way she acted it seemed as if she had had the same hope
that he would be there also.
"My god Hal, what happened to your eye?" Lila asked as soon as she
saw him.
The pain had left put the black and blue mark was still very
distinct. "Nothing Lila. I ran into a door."
"Hal, if you can't tell me the truth than what kind of friendship
can we have."
"I'm sorry Lila. I got hit."
"Hit?"
"Yeah, Debbie punched me very hard. I don't know, it happened so
fast."
"Did you provoke it?"
"What do you think Lila? Is there anything I could do to deserve her
hitting me?"
"Of course not."
"It's strangely like what you said about Brock. She's decided she
wants complete control of me sexually. I rebelled and she hit me."
"You couldn't stop her?"
"You mean as the man in the relationship I should have been able to
out muscle her? Well, it turns out she's been working out so hard she
can pretty much do anything she wants to me physically. She has
gotten unbelievably strong. Her biceps and calves are like iron.
And..."
"And what Hal?"
"And you're probably wondering why I don't just leave. Well actually
Debbie told me I could leave. She said she wouldn't stop me. She also
said I'd never have the courage to leave her. She knows that I'd be
scared to have to start my life over. She is so much tougher than I.
She'll get some high priced lawyer and skewer me. I bet Ill end up
with nothing. I'm scared to think where I could end up living.
There's also the fact I probably still love her. I mean we have been
together a long time. I have to trust that what's happening now will
not be permanent."
"I can honestly understand where you're coming from. In fact I could
probably say a lot of the same things, only maybe Brock would not let
me go. He'd probably really hurt me physically if I tried to. He gets
off on me being his prisoner and receptacle. I'm like his little
private whore."
"Yeah, it's so weird. My relationship with Debbie is falling into
the same pattern that you have with Brock."
They embraced and Hal made no attempt to separate and he felt happy
that Lila was holding him more than perfunctorily.
"Debbie has sex with me anytime she feels like it. Nothing so much
as a pleasant request or some foreplay. No, its just get in the
bedroom, take your clothes off and boom. Then she's never concerned
about my sexual frustration or anything. And I haven't told you the
worst of it."
"What's that Hal? Something worse?"
"You see these studs in my ears?"
"Yeah, I saw them. A lot of men get an earring."
"Both ears?"
"No, usually one."
"Look closely. I've got them in both ears."
"Oh, my God you're right."
"Yeah because Debbie is like basically turning me into a girl. She
calls me her bitch. She makes me wear her clothes. I spend the day in
a dress, pantyhose, you name it."
Incredulously Lila asked, "a bra?"
Hal shook his head up and down. "Now you're really repulsed by me."
"Don't say that Hal. I don't want to be judgmental. I trust that
whatever is going on with Debbie, you're trying to do the best that
you can under the circumstances."
"Gosh Lila, you really are a nice person."
"Its not that I'm nice Hal it's just that you deserve to be treated
nicely. We all do."
Hal desperately wanted to embrace her again and he did so. Standing,
holding this woman made his heart race and he knew that if he was
totally honest with himself he had already started loving her.
"I also don't have an issue with cross dressing," Lila said.
"Actually my younger brother was a cross dresser and I pretty much
grew up knowing that he was always into my things. It was actually
pretty funny after awhile."
"I don't know if I'm really a cross dresser," Hal said. "I mean it's
Debbie who's forcing me to, but to tell you the truth it doesn't
bother me all that much. Debbie says that she sees a lot of girl
inside me. Well, in comparison to her I guess I do appear to be
girlish."
"Do you think there is a lot of girl inside you?" Lila asked.
"I suppose so. Even if there is not a lot of girl, there is
definitely not a lot of man. I don't enjoy being manly. I guess I
never have."
"I think I'm really enjoying that fact. I mean I could like you even
if you were manly, but the way you are is maybe even better. I think
we can connect better because of your feminine side. I hope you don't
take that the wrong way."
"I understand what you're saying and I agree with you."
Lila was making no move to stop the embrace and Hal's heart soared
with the knowledge that Lila must be feeling every bit as much for
him as he was for her.
Finally he said, "if one day I show up here in a dress, would you be
freaked?"
"What kind of dress?" Lila asked jokingly.
"So far Debbie has me looking like Donna Reed."
Lila laughed. "I like Donna Reed."
There was a long pause and Hal said, "I guess we had better do our
laundry."
"You're right. Brock tends to get real edgy if I do anything
unpredictable, like taking an extra minute down here."
"You swear that he's not hurting you, right?"
"Not in so many words. I think the worst of it is how hungry he is
for my body all the time. He never seems to get enough and he doesn't
care about me at all."
"I think Debbie is the same way. We've never had so much sex as this
week, and it's always her just telling me to get in the bed, spread
my legs and then a minute later she's done and forgotten about me."
"Boy that could be Brock."
"I wanted to tell you that last week after we spoke, I could hear
Brock and you through the wall. I had the definite impression that
you said something like "gentler Brock. Not so rough."
"I wouldn't be surprised if that was what I said. He's got an
unusually large organ. It gets sort of unbelievably big when excited
and it can barely fit inside me. But that never slows him down."
An image of a colossal penis appeared in Hal's imagination, and he
doubted if he'd be able to not think about that the next time he saw
Brock.
"I've got to go," Lila said. "I've really enjoyed talking to you.
Maybe we could have coffee during the day one day. I mean Brock and
Debbie are out working and we're right next door."
Hal smiled. "Of course Lila that would be wonderful. I'll give you a
call one day."
"Bye."
"Bye."
When Lila left Hal wondered when he ought to call her. It was
definitely a dangerous thing. Alone in an apartment together, what
would stop them from really falling in love?"
***
Hal decided that he had best wait until Monday before calling Lila.
After a whole weekend of dealing with Debbie, and she with Brock,
they would both need the opportunity to commiserate with each other.
The weekend for Hal turned out to be filled with trips to buy ladies
clothing and an ever increasing pressure from Debbie to be more
feminine. She made him comb his hair in a style that would anticipate
the day when it was long enough to be womanly. Debbie went over the
do's and don'ts of makeup until he was confidant he could put on
lipstick, mascara, rouge, and eyeliner as well as most women could.
In what turned out to be a hard adjustment he learned to become
aware of his hands and how he touched things or reached for things so
that his gestures were gentle and graceful. According to Debbie that
had the ancillary benefit of reducing the frequency with which he
might break a nail. She put nail strengthening solution on his finger
and toe nails and then a shade of pink polish.
Hal's wardrobe of women's clothing expanded well beyond the first
hand me downs that Debbie had given him. He had several new dresses,
several boxes of stockings, and a number of new bras. Debbie even got
him an all-in-one girdle and bustier and entertained herself watching
him put it on and fasten stockings to the garters.
"It's very constraining," Hal said. The garment seemed to have a
mind of its own; various lace panels pushed in his tummy and rounded
his butt.
"Tell me about it," Debbie said.
After awhile he got used to wearing it under his dress. In fact, he
no longer thought much of putting on anything other than a bra,
panties, hose and a slip each day that he got up. Debbie brought home
some low heels which he wore mainly when she was home. Otherwise he
wore flats that he thought were more comfortable.
Hal found that he preferred wearing a garter belt to hold up
stockings. Together with wearing a dress it was especially convenient
for the many times that Debbie wanted sex from him. It was easy to
lie on the bed, have her raise his skirt, yank down his panties and
then have her way with him. When she was done, he could go about his
business until the next time. The weekends were particularly tough,
since Debbie sometimes wanted him many times during the day, and he
would lose count of how many times she had made him get hard and had
her quick orgasm. He could only safely relieve his own sexual desire
at night after she was asleep.
When Monday morning rolled around, Hal had lost his nerve about
calling Lila. He decided he would wait to see her one more time in
the laundry room just to make really sure that she wanted to get
together during the day.
When Wednesday rolled around and Debbie had left for her class, Hal
raced down to the laundry room only to find out that Lila was not
there. Nor did she come though he spent an hour doing the laundry.
When he got back to the apartment he put his ear to the wall to see
if he could hear if Lila was home. Right off the bat he heard what
was definitely her voice. She was crying out as if in pain. Plain as
day he heard her saying, "don't. It hurts. It's way too big Brock.
It's a lot bigger than yours and with yours at the same time. I
can't."
Quaking in fear Hal heard another man's voice, it was definitely not
Brock saying, "you sure she can take both of them, buddy."
"Don't mind her Cal. She loves it. Don't you baby?"
"No, Brock, you know I don't."
Hal heard Brock laughing. Then Cal said, "she can just suck on my
dick while you get her butt."
"Yeah Brock. Just let me suck it. I think I can get it in my mouth."
"No man. She gets yours up her pussy and mine up her butt. Don't
worry; she's going to love it once we work out the kinks. Aren't you
honey?"
"No, Brock. He's way too big. You're both too big. You need smaller
ones." Hal heard her whimpering and crying out softly in pain. In a
panic he didn't know what to do. He put on his jeans and shirt and
shoes, ran out the door, and down the stairway three flights, out
into the hall and yanked the lever on the building fire alarm. Then
nonchalantly he continued on his way down the stairway. As he
descended other people joined him and outside they merged into a
growing crowd of residents that formed on the lawn in front of the
building. In the distance Hal heard a fire truck coming. A minute
later he saw Brock and Lila appear, followed by a guy in jeans and a
cowboy hat. Hal hid partly behind other people so he wouldn't be
seen. Cal and Brock appeared to be talking and then Cal walked away
toward the parking lot where he got into a pick up truck and drove
off. As Cal was leaving, Hal saw Debbie's car pull up and park. Close
behind her was the fire truck.
"Another fire alarm?" Debbie said to Hal when she joined the group
in front of the building.
"Yeah, I had just finished with the laundry when it went off."
Debbie looked him over. "I don't recognize you without a dress."
"I'm sorry, I was afraid to run out of the building in a dress."
"The next time you will."
"Sure Debbie. I promise. The next time I'll just keep my dress on."
"Hey, there's Brock and Lila," Debbie said, "let's say hi."
Nervously Hal followed Debbie to them.
"Hey, Deb," Brock said and exchanged a small kiss with her. It
looked so familiar that Hal was surprised.
"Hi Brock, Hi Lila," Debbie said.
Lila smiled weakly and said, "hi Debbie, and Hal too."
"Hey it's my man, Hal," Brock said and extended his hand to Hal.
"Hi guys," Hal said and self consciously took Brock's hand certain
that he would see the pink polish on his fingernails. Hal tried to be
firm with his handshake, but felt it give way under Brock's vise-like
grip that painfully cracked his knuckles. Hal attempted to smile
through his pain.
"Another damn fire alarm," Brock said.
"They're too frequent," Hal said.
"Probably just kids," Debbie said.
"They've got a new video surveillance system set up that I hope
catches the bastards," Brock said. He said this to Debbie as if Hal
wasn't there. Hal only half-listened, instead thinking about Lila. He
glanced over at her while Brock continued "how's class? Doin your
reps?"
Lila looked at Hal with a mournful look and he went over to stand
next to her. Brock and Debbie wandered off to talk to a fireman and
Hal said, "I missed you at the laundry."
"Yeah, Brock had a friend over. Maybe you saw him leave."
It looked to Hal that Lila was fighting back tears.
"Yeah I saw him. In fact..."
"Oh, no, I hope you couldn't hear..."
"I could Lila. I couldn't take it and I ran out and pulled the fire
alarm."
Lila's jaw dropped in surprise and she said, "that's got to be the
nicest thing anyone has ever done for me. They were ripping me apart.
You heard what they were doing."
"I know it's really gross."
"It's a sick thing that Brock cooked up. He gets his friend on the
bed and I have to take him in me and then Brock comes at my rear. I
don't know where he found this guy Cal but he's got a bigger prick
than Brock's. I mean when I saw the two of them standing there naked
flaunting there big dicks in front of me I figured I'd never live
through it."
"I'm scared for you Lila. I won't always be hearing what's
happening. I don't know. I feel so bad."
"I don't think this is going to be anything more than a one time
deal. Cal was saying he had second thoughts. He doesn't like looking
at Brock's penis. He said he'd much rather have two girls."
"I hope that's true," Hal said.
Brock and Debbie came back. "The fireman says it'll be a minute
longer," Brock said.
Hal wished he had said something to Lila about still wanting to
phone her but it was now too late. First Brock and Lila and then he
and Debbie filed back into the building after the fireman gave the
all clear signal.
***
Sunday at exactly 11:11 AM, Debbie announced that she was taking Hal
to Dr. Silverman, a cosmetic surgeon, to get him fitted with boobs.
Hal knew the exact time, since the impact of her casual remark had
been so powerful that he was unable to take his eyes off the clock he
happened to be looking at when she made the announcement. Her
statement had taken his breath away and while he fought to regain his
composure she said, "What kind of breasts would you want? Definitely
not a cow, but not Twiggy either. Something feminine without being
ridiculous. I'm sure you'll be overjoyed to finally fill out your
bras. We'll talk it over with the doctor."
Hal felt like he was trapped in a tight space. He toyed with the
idea of standing up to Debbie. Telling her he would leave her rather
than get breasts, but the reality was that he felt so inadequate
around her that his only response was to cry.
"I can see your tears Hal. Why are you crying?"
Her question made him feel even more like crying. "I don't know,
Debbie. It's because I don't know."
"You don't know because you don't know? If you're crying about the
pain, there won't be any. In fact, the operation is routine nowadays.
There's no danger. Millions of women a year get boob enhancements and
I know that Dr. Silverman is the absolute best."
"But I'm not a woman," Hal said so inaudibly it was as if he just
mouthed the words.
"Speak up," Debbie said.
"Isn't it my body?" was all he could say.
"Not anymore," Debbie said. "You're not going to be difficult are
you? We've been getting along so great, it would be a shame to take a
step back."
"I'm sorry Debbie."
"It's OK. Come. Watching you cry always makes me horny. Anyway, I
wanted to show you my new toy which you're going to grow to love."
In the bedroom she took a strange object out of a plastic bag. It
consisted of two replicas of a penis with some straps on one side.
Hal was terrified by the sight of it.
"There's no reason to be afraid. Like I said, this is going to
become your friend. Let me show you how it works. I put the one penis
inside me, tie the straps around my legs and now I've got a cock just
like you, well actually a bit bigger than yours."
"I don't understand," Hal said. "Why do you need a penis?"
"Gosh Hal, sometimes you're so dense."
"You mean you're going to..." Hal vaguely pointed in the direction
of his rear end.
"Bingo, Hal. Only let's first have lunch. Then we'll get down to
business."
While Debbie nonchalantly ate the turkeycado sandwich that Hal had
prepared and remarked at how nicely it tasted, Hal nervously looked
at his own sandwich without eating it. He had been hungry but he no
longer had an appetite. He wanted to run away somewhere to protect
his butt from what looked like was going to be a savage attack by
Debbie. He got up from the table and went into the bathroom, sat down
and sobbed.
This day he had been wearing a new pink dress with a floral trim in
white daisies. It had an attached starched crinoline that held it
out. When Hal had first seen it, he had wondered how Debbie had ever
found a dress of that style that would fit him. Surely only young
girls going to Communion or Confirmation ever wore such dainty
outfits. When he first put it on, he felt silly wearing it. But by
the time lunch had rolled around he had come to see that it was
probably exactly the sort of dress he ought to be wearing, since it
presented him in the delicate and subservient manner that Debbie got
off on.
Debbie took the last bite of her sandwich, drank the last of her
coffee and got up from the table. "Come my puppy, the bedroom awaits
us." Without a second thought Hal lifted up his dress, lay down on
the bed and pulled down his panties. He could feel his penis already
starting to stiffen. "No Hal," Debbie said, "we're going to have some
fun today with out new friend."
"I'm sorry Debbie. That thing scares me. I'm terrified of it. It's
going to hurt me and probably permanently deform me or something."
"Don't be so dramatic. I guarantee you that after the initial pain,
you'll be begging me to bugger you. If it makes you feel any better,
just think of it like you're a bitch in heat and until you get that
big cock inside of you, you're desperate."
Debbie directed Hal to lie on his stomach on the bed and then had
him raise his hips sticking his ass up into the air. She placed two
stacked pillows under his chest so his face wouldn't be forced down
into the comforter.
"I love how submissive you are Hal. I love the way you cower."
She placed a fist right next to his face and he reacted instantly by
shutting his eyes and turning his head. He felt his penis stiffen
more.
"You are a great cowerer," Debbie said.
Debbie carefully arranged Hal's dress so it fell over his back up to
his head. Hal shook like a leaf with fear.
"Take your panties off, it'll be easier. I need to spread your
cheeks apart."
While Hal did that Debbie got the dildo in position between her legs
and tied the straps on.
"Do we really have to do this?" Hal said.
Debbie laughed. "You're in a good position now. I put a little jelly
stuff on my big cock and then all I have to do is aim it at your
little hole."
Hal felt the tip of the dildo as she put it against him.
"Now that doesn't hurt does it?"
Hal felt the pressure slowly increase as Debbie pushed harder and
harder against him.
"Reach your arms back toward me," she said.
Hal did like she said and Debbie took hold of his arms using them to
gain more leverage as she pushed harder still on the dildo. Hal felt
his hole starting to give and the dildo begin to enter.
"Man, you're a tight one," Debbie said, keeping up the continuous
pressure. "What's really nice is that this doo-dad gives me a jolt of
pleasure every time I push in on you. God this is so neat."
"It's starting to hurt," Hal said. Debbie held his arms firmly and
he found that there was no way he could turn or move. All he was
aware of was the relentless pressure of the dildo that Debbie
steadily pushed into him. The dildo slipped forward a bit and Hal
yelped in pain. Debbie eased up her advance.
"I think the expression tight ass was invented with you in mind,"
Debbie said, "man this is hard work."
"Your penis is too big!" Hal cried out.
"Easy does it Hal, we'll soon be getting there." Debbie started
pushing again. "You really have a gorgeous butt and such sexy thighs.
I mean if I didn't see you're rod sticking out, I'd think you were a
girl."
Debbie was right about one thing; his own penis seemed to swell up
along with the pain in his bottom.
"After this time we'll have another great option. I'll be able to
bugger you or screw you. Even better, I'll be able to bugger you and
then screw you."
Hal's sphincter muscle slowly relaxed under the onslaught of the
large dildo until it now seemed like it would be possible to get the
whole thing inside. The top part of Debbie's "penis" was buried
inside him and Debbie said, "OK bitch, now I'm going to stick my cock
in you up to your tonsils," and she pushed forward hard.
At first Hal felt another sharp pain and then the whole dildo
suddenly slid all the way inside him. The pain now mingled with a
feeling of being filled up inside. It was as if a warm fluid had
seeping into his lower abdomen. He also had the impression that some
fluid had run out of his penis. The sensation of having been
conquered by Debbie overwhelmed Hal. The sensation of being filled up
joined with one of being trapped and he was powerless to stop Debbie
from doing whatever she wanted to do with him.
"Oh my goodness," Debbie said, "I don't think I've ever felt so
hot." She pulsed the dildo through a small oscillation and waves of
pleasure crept through Hal's prostate and up into his penis. Debbie
let go of his arms and grabbed his shoulders with her hands. This
gave her a chance to move more rapidly in larger arcs in and out.
Debbie kept up a continuous stream of excited yelps of pleasure. She
varied the pace and length of her strokes as she slid the dildo in
and out of his bottom. All Hal could see was the bed in front of him
and he felt like the act was impersonal, like he was a whore,
sticking his bottom up in the air so some random stranger could have
their fun. He imagined that Lila might very well be in the same
position right across the wall with Brock ramming his penis into her
rear. Luckily for himself, he didn't have to worry about giving
Debbie blow jobs on demand. He would have to see Lila again and tell
her all that has happened to him.
Debbie frantically moved at a feverish pitch until Hal felt her pull
the big dildo out of him and heard her run to the bathroom. He waited
with his ass up in the air for her to return. When she did she told
him to get on his back. He saw that she had taken off her device.
With his penis standing straight up she then fucked him her normal
way. She was satisfied in a matter of a minute or two and then
climbed off him.
"Thanks Hal. That was probably the best ever," Debbie said. Hal's
bottom tingled with both pleasure and pain. Even though the dildo was
no longer in him, it felt like it still was. It was a feeling that
was not going to go away for quite some time. He imagined that he was
like a new bride after losing her virginity. Even though it had only
been a dildo inside him, he felt like his rear end had been filled up
with semen, that somehow Debbie had had a real cock and had shot a
huge load of cum into his backside.
Hal was exhausted and dozed off. When he awoke his mind filled back
up with remembrances of what just transpired. He would probably be
able to manage with Debbie having at his bottom. The bigger problem
was her reference to him getting boobs. It didn't seem right that she
should make such a major decision without even asking him his
opinion. To say the least that was highly inconsiderate. He had
gotten used to wearing bras but the fact that he was flat chested had
been a source of at least some concern to him since it was plainly
obvious, every time he looked in a mirror while wearing a dress, that
even a small suggestion of a bulge across his chest would make him
look better. Perhaps that was all that Debbie had in mind. Some small
implants that would just take him away from being totally flat,
enough breast to at least puff out the cups of his bras a little bit.
***
As promised, Monday afternoon Debbie took Hal to Dr. Silverman, a
plastic surgeon to arrange for his breast implants. For the first
time she had him leave the apartment dressed as a woman.
"It's important for Dr. Silverman to know that you're a transsexual
before he'll consent to do the operation. They don't let just anybody
walk in off the street and get boobs."
"Am I a transsexual?" Hal said.
"I think you are. Let's face it Hal, you surely aren't a man. I mean
if you were, would we be going to Dr. Silverman today, and would you
be dressed so prettily?"
"I don't feel like I had any choice. You punched me that time. I've
been very afraid of crossing you. I'd rather try and make you happy
then risk getting you angry."
"You act and sound just like Lila next door."
They had gotten to the car. Debbie held the door for Hal and he
neatly sat in the front passenger seat after first gathering his
skirt so it wouldn't touch the ground." At the sound of Lila's name
Hal gr