Training Bra
When LouAnn Dehen’s lubricated right thumb was inserted into her husband William’s
rectum, the rest of her fingers could basket his testicles, alternately squeezing and
releasing them, squeezing and releasing them, depending on the particular vocal response
she sought from him.
Her lubricated right thumb was thus inserted at this moment. LouAnn gave her
husband’s testicles a good, hard squeeze.
“Uuueeegh!” William squealed. “Uuueeegh!”
LouAnn smiled. Using her left hand, she skillfully fondled the head of William’s
erect, condom-covered penis which stuck out from his otherwise naked body, stiff as a
steel spring. The condom was also lubed from base to tip with the same clear, unscented
water-based gel that coated LouAnn’s right thumb.
LouAnn always made it a point to milk her husband before dressing him up in one of
his girly-girl outfits, thereby keeping the state of his arousal down to a halfway
manageable level.
William was kneeling on the chaise lounge chair that sat in one corner of their
bedroom, on all fours, his rear end level with his head. The condom’s reservoir tip poked
out from LouAnn’s hand with each thrust of his pelvis. She sat beside him, not on the
chaise lounge, but on her softly padded vanity bench.
In contrast to William’s nudity, LouAnn wore an exquisite matching bra and panty set.
The rose-colored fabric was edged in ivory lace, encircling the push up cones of LouAnn’s
bra and the waistband of her high-cut French panty.
In addition, LouAnn’s bra had elastic straps that served to lift and separate her
shapely breasts, further enhancing the contours of her fetching upper body.
In point of fact, LouAnn’s body, upper or lower, needed little in the way of
enhancement. She was now in her early thirties, blessed with a lush auburn mane which
reached her shoulders, and a sleek, lissome figure that marked her as an especially
beautiful woman.
Nor could William be described as any kind of slouch when it came to looks. He
possessed handsome features, a thick shock of dark brown hair, and a muscular body that
was slim and solid, if a bit on the short side. In his stocking feet, William stood a full
inch shorter than his five foot, nine inch wife.
On the other hand, there was something about William’s face, in his slightly receded
chin, perhaps, that bespoke a dearth of masculine aggressiveness. One of William’s male
friends had joked at their wedding that if it ever came down to a wrestling match, “LouAnn
could pin Bill three out of four falls.” Which foretold, in some small way, perhaps, the
current state of their marital dynamic.
During their marriage, LouAnn had come early to the habit of cross-dressing her
husband, although it took several more years before she came to thoroughly dominate him.
Well, better late than never, LouAnn thought.
Initially, she’d had concerns about marrying William Dehen, taking her sweet time before
deciding on his worthiness.
Nevertheless, moving her husband from dressing in women’s underwear to being LouAnn’s
absolute underling had been a surprisingly swift process.
LouAnn made the decision on the eve of their third wedding anniversary that she would
henceforth assume complete control of their marriage. The result for LouAnn had been an
even happier, satisfying union.
Because of William’s willingness to subordinate himself to his wife entirely, she
presently had almost no complaints about their relationship.
Her husband was a hard worker, the manager of a technical services company, earning more
in a single year than LouAnn’s ex-husband Brian had earned in the whole five years they
were married.
The only remaining issue was how far LouAnn and William would go into the realm of
Feminine Domination.
I intend to opt for more of the same, LouAnn thought. I’ll enforce a more effective,
more abject submission on William’s part. Continually develop new and exciting methods of
bringing him to heel and restricting his orgasms.
Likewise in his early thirties, buff, attractive William was the ideal escort for
LouAnn when they attended dinner parties, concerts, or social events. Her husband looked
dashing in black tie, and, as a rule, was always impeccably dressed.
No one but LouAnn knew that, under William’s trousers, she had him in a size seven
lace panty; and, under that, his genitals were confined in a secure polycarbonate male
chastity device. Nor would anyone know that his bodily hair was completely shaven from his
neck on down, with particular attention paid to his genitals.
That was how things were now, tonight, on the eve of their fourth wedding
anniversary, also known as Valentine’s Day.
Early in their courtship, LouAnn had learned about her future husband’s penchant for
cross-dressing. Back in the months after she’d divorced Brian and started dating William,
the latter had lived in a studio apartment near Slateville State University.
While dating, they’d come close to having sexual intercourse on two occasions, both
times at LouAnn’s house in Southwest Slateville. However, each time LouAnn had called a
halt before they did, informing him that intercourse was something that she wanted to hold
off on.
Then it occurred to LouAnn that she needed to speak frankly with William about sex
before they became intimate; and one Friday morning, she called him at work and asked if
she could come to his studio apartment for an overnight visit.
Of course, William had said yes.
As soon as William opened the door to let LouAnn in, she greeted him and kissed him.
Then, after he closed the door, she stripped down to her lingerie, making it clear that
this time she intended to have sex with him.
However, before that occurred, LouAnn told William that she wanted to have a
straightforward discussion with him about her sexual preferences. Her ex-husband Brian had
refused to give her cunnilingus, she said, a pleasure she expected, desired, and felt she
deserved. If William had similar qualms, she wanted to know about it right up front.
Should he be the kind of man who would deny LouAnn oral pleasure, their relationship was
going to be terminated immediately.
William told her of his attitude towards cunnilingus. She was pleased to learn that
he would be more than happy to provide her with the intimate service she craved.
“But now that we’re on the subject of sex,” William said, “I should probably confess
something to you.”
This was not what LouAnn had expected.
“Go ahead,” she answered, bracing herself for the worst.
What could William’s confession possibly be about? Herpes? Impotence? Compulsive
masturbation? Homosexuality?
Her mind briefly ran riot.
In the next few minutes, William confessed to LouAnn that he was obsessed with
women’s lingerie.
“You mean to look at, don’t you?” LouAnn had naively said. “On me, you mean?” She
indicated the expensive, form-fitting bridal-white set that presently adorned her body.
William pressed his full, girlish lips together nervously. “Well no,” he answered,
averting his eyes. “I mean on me, I guess.”
“What do you mean? On you?”
“What I’m saying, LouAnn, is that I enjoy wearing women’s underwear. I’m telling you
this because I believe you ought to know about it. It’s kind of a compulsion that I
have.”
LouAnn was surprised. Somewhat shocked, actually.
“I think we need to talk,” she said.
They’d had a long talk then, during which William described his women’s lingerie
fetish, and how it frequently took hold of him. LouAnn asked numerous questions—about how
often he indulged, about what he liked to wear, what he did when he was dressed in women’s
underwear, and the like.
During the course of that conversation, LouAnn learned much about her new lover that,
unaccountably, intrigued her. It also touched her because she realized William was opening
himself up to her, being vulnerable in a very personal way. For the first time, LouAnn
felt an emotional closeness with him, a closeness that exceeded what physical intimacy
offered, and a closeness that she’d never experienced with Brian.
“So, do you wear any other kinds of women’s clothing?”
William shook his head. “No, just lingerie.”
“Do you happen to have any women’s lingerie on hand? I’d like to see some on you if
you do.”
“Right now, I don’t have any. I threw it all away.”
“What? Why would you do that?”
“You see, LouAnn, I knew I was going to have you here for the evening, and I didn’t want
you seeing women’s lingerie in my drawers or in my closet. You might think it was weird,
or that I was seeing another woman. I guess I’m kind of ashamed of it. I suppose doing
what I do makes me kind of a sissy.”
LouAnn was moved. “William, you needn’t feel ashamed. I actually think it’s cute that
you’ve got this little fetish. It makes you more endearing to me.”
“Really?” William was relieved. And happy. He’d expected a much more judgmental
attitude from LouAnn, who was quite conservative about nearly everything.
“Yes, really.”
“Thank you, LouAnn.”
“You’re welcome.” And with that, LouAnn kissed him. And soon after the kiss, they
were on his bed, about to begin making love. William might like wearing lingerie, but his
desire for her was evident. He sported an enormous, bulging erection. Things grew
extremely heated until LouAnn, still wearing her bra and panties, suddenly turned her back
to William.
“Take off my bra,” she said.
“Yes, LouAnn.”
“Remove it slowly,” she added. “Once the hooks come free, don’t just yank it off. I
have very sensitive breasts, you know. Especially my nipples.”
“Yes, LouAnn.”
The city lights slanted through the window as they stretched out on the big double
bed William preferred over the fold-down that came with his apartment. With trembling
hands, he undid the hooks of LouAnn’s lacy brassiere, knowing exactly how it came off,
knowing how to undo the tiny hook and catch gizmos in back. LouAnn could tell he handled
it very adeptly.
Things were moving along at a rapid pace, and William was impressed with LouAnn’s
assertiveness. Not too many women would respond like she had, he was sure.
And the question about cunnilingus—well, William supposed she had every right to know
about his attitude towards it.
It made him desire her all the more.
From LouAnn’s perspective, their physical intimacies would be extra special because,
now, she knew a secret about William, about his penchant for wearing women’s lingerie.
William felt incredibly excited. The hooks came free and the elastic straps were in
his grasp. The satin cones in front fell away as LouAnn sat up, allowing the bra to slip
from her warm breasts. William put it on the nightstand by the bed.
Thus released from her bra, LouAnn turned over, exposing her firm, shapely,
cherry-nippled, size 38C breasts to William. In doing so, he got the full visual effect of
her mammaries.
Yes, he might enjoy wearing women’s undergarments. That was indeed true. But William
was no homosexual. Quite the contrary, in fact. The sight of LouAnn’s sleek, slim body,
with the red-crowned peaks of her breasts right there, so near his lips, had a violently
arousing effect on William.
All that was left to go before LouAnn’s body was completely nude were her pure white,
bridal-style panties. Oddly, however, she seemed in no hurry to take them off.
Rising up on one elbow, LouAnn tugged at William’s left hip, rocking him back and
forth.
“Maybe you should put my bra on,” she said. “I think it might sort of fit you.”
William’s eyes went saucer wide, wider even than they had been from staring at
LouAnn’s spectacular boobies.
“You… you wouldn’t mind?”
“No, William. I think it might be fun. No—I’m sure it’ll be fun, seeing you with my
bra on.”
William’s face lit up.
“Okay.” He didn’t need much convincing.
Both LouAnn and William were skinny as rails then, the way you are in your early
thirties. LouAnn’s bra actually fit William rather well, as it turned out. Except for the
fact that what he had up top came nowhere close to filling out the cups.
At LouAnn’s suggestion, they went to go stand in front of the ornate full length
mirror outside the bathroom.
“When I turned twelve, my mother bought me what was then called a training bra,”
LouAnn explained. “At the time, I hardly needed anything, but Mother’s sharp eye told her
that I would be needing one soon, as I had begun to develop. By the time I was thirteen, I
was ready for a regular bra.”
The mirror showed two smiling, attractive young people, the man wearing a bra and a
towering erection, the woman in bridal white panties. While gazing at their reflections,
LouAnn’s hand strayed to William’s upright penis.
She admired her bra on William, noting how the cups hid his tiny, manly nipples. Of
course, the cups were too large for his fried eggs. On the other hand, the straps were
just about right. But what William really needed was a training bra.
Another drawback was his relatively sparse chest hair. Sparse or not, it would have
to go.
Messes up the look, LouAnn thought.
“I think you should put on my panties, also,” LouAnn said. “See if they fit you.”
“Your panties?”
“Yes, see if they’ll stretch out far enough in front to cover this naughty big
thing.”
“Okay.”
And with that, LouAnn released her grip on William’s excited member and started
taking her panties down. She stepped out of them and let them drop to the floor.
“If you want to wear my panties, William, you’ll pick them up. Do you mind?”
“No, I don’t mind.”
“Go ahead then.”
William bent down and picked her panties up from the floor. Getting them over his
legs (one leg at a time) went easier than LouAnn expected. The challenge came when he
tried to pull them up past his erection. He finally got it covered, although it bulged way
out in front.
“What do you think? Is this ridiculous?”
LouAnn laughed. She couldn’t help it, not with the sight her lover presented.
William flushed beet red.
“You’re laughing at me,” he said.
Mastering herself, LouAnn quickly answered, “I’m laughing because it’s so sexy to see
you wearing my lingerie, William. I think I am getting turned on. Very turned on.”
LouAnn embraced him and they kissed. Her tongue probed his mouth, and he responded
with fervor.
“Let’s do something we haven’t done yet,” LouAnn said, her voice husky with desire.
“I want you to go down on me.”
William’s breathing became labored as he considered giving LouAnn the oral pleasure
they had just discussed.
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