Jack could feel the tightness of the ball-gag his arms behind his back held in place with his wrists cuffed he looked on as he sat on the bench seat in the bathroom while Marilyn slowly ran the shaver along his leg. It was the last of the hair to be removed on a body that was becoming thinner and less manly looking.
"Sweetie there you are....all smooth and hairless...I like the little triangle patch on your mound...it looks so cute I wonder how a floral tattoo would look right at the bikini line....now for some body oil...you'll love the feeling of it on your smooth legs before we move to your tummy and bosom."
Tummy and bosom?...he never called it that.
The woman cupped his balls briefly letting her fingers delicately jostle the sensitive pair heightening his arousal. A flower tattoo...bikini line... his mind thought about what she said as he looked at the femme triangle of pubic hair. Jack knew he couldn't let any of his friends ever see it.
Holding the bottle up the words 'estrogen and progestin' popped out among the others as he read them watching Marilyn take her birth control pill. Her hand brushing along his smooth face she smiled.
"Some days it's hard to be a woman...yet I've never grown tired of the feeling of estrogen."
Ever since the chat between Naoma and his Marilyn a few weeks back he suspected he'd been on feminizing hormones since the morning she confronted him months earlier. The day after their argument he had wondered why his medical records lay printed out on the kitchen table as she went over his blood work while on the phone with a female doctor Marilyn knew.
Becoming less assertive as the days past if he was on estrogen what kind of scared him was that he enjoyed the feeling.
"Ok dear we'll play the 'Q' and 'A' game my friend Naoma suggested....after all marriage is about communication and growth ...I'll play with these orbs and ask you questions and you answer truthfully....sometimes I wonder how you'd look without these...don't they get in the way when you walk?"
Marilyn stood up reaching in back she unclasped her bra and lowered her panties seconds later.
"I want you to think of a pussy and how beautiful it is...look at my breasts....don't they look lovely....you ever think of how fun it would be to have your own?"
Her hand ran along the labia folds of her vagina slipping inside past the slit of her lips. The feminine aroma soon filled the air in the bathroom. Marilyn ran her finger under his nose letting its scent stay there for him to take in.
"Thinking how to improve our relationship we should learn to communicate better ...so tell me. ...a real man can control his orgasms right?"
Jack nodded his head gurgling out a 'esssss' from behind the ball-gag.
"If that's true....conversely if he can't control his orgasm then he's not a real man....if he's not a real man then what does that leave?"
The inquiry hung in the air.
Jack seemed to be contemplating the logic-chain. Looking at Marilyn he watched her lather up an anal plug with lube. Like the 'fishes and the loafs' a little went a long way as the 'Uber-lube' magically spread out all over the whole piece.
"Do you like doing things that make you feel good?"
"Then if you are open-minded and try somethings you never had before and like then you'd most likely want to continue them correct?....Baby your skin feels so soft with all that hair gone."
His head bobbing a 'yes' again Jack let out a moan on feeling her hand run along his thigh. He wasn't used to being man-handled yet Marilyn easily moved him by the hips exposing his rosebud entrance.
Her breasts were beautiful the more he stared at them as they swayed he wondered why he had taken them for granted all these years.
"They're lovely...aren't they?...they feel so nice to have especially when my nipples are sucked...once a woman makes the connection between her breasts and her mind and her sexuality she develops a whole new level of femininity....and then there is the pretty bras we get to wear."
Her finger slick with lube slid in past his rosebud moments later a 2nd finger slipped in as she used them to spread the opening wider before gently easing the butt plug in. Spreading out from the pointed tip once it accepted the widest part of the width the suction of his entryway pulled the entire length in without Marilyn using her hand.
The sensation different but not painful the end of the piece large and round spread his cheeks wider. Lifting his head Jack saw Marilyn taking a few pictures with her phone.
Hairless, a chastity cage on with a butt plug in he drew a level of concern wondering if anyone he knew would ever view them.
Marilyn slid the panties along his skin only to see his flaccid penis stretch to the end of the metal restriction of his cage.
"Does that feel nice on your skin?....panties are such a delight."
He let an 'eeesssss Ma'am' escape.
"Good...so you like it?"
Jack nodded his head moments before Marilyn continued making her point.
"What'd we agree on? if you like it then you'll only want more of the same ....panties...I'm afraid from here on out I'm going to insist on it but i do think you'll come to enjoy wearing them every day."
The declaration made him think about it.
"Let's see how much you like feeling them on your mound...now if you are a real man you won't come...you did say you control it not to mention their panties ....womens panties...very feminine panties....do real men wear panties? .... hmmmm?"
Marilyn bent down letting her lips surround his areola as she rubbed the panties on the hairless mound. His butt cheeks clenched pulling the anal plug deeper as he saw the woman suck and lick. Sensing a feeling of feminine-like penetration he felt his arousal suddenly spiking out of control.
Jack hadn't thought it possible yet he watched as cream spurted out from behind his chastity cage.
The act had brought him into a new paradigm awareness. Not only had he not control it he had orgasmed with his cock locked and a butt plug in his rear.
He stared at Marilyn realizing she had made him come by treating his nipples like a woman's without once touching his dick. The feeling of panties caressing his skin somehow it help further shatter his long held illusion of male superiority
Drained of his seed and energy butt plug in place a few minutes later her husband held still as she lowered the nightgown down on his body. He went to bed free of any objection quickly falling asleep wearing a nightie and pair of panties.
In the small early morning light what Marilyn liked was how much the base of the anal plug spread his ass cheeks wider. It gave them more of a feminine look and feel as she ran her hand gently on his bottom. The touch was enough to wake Jack as he held still enjoying the feel of it.
The strap-on slipped in so easily both on their sides with their hips and knees stacked Marilyn let her hand rest on his waist as she pushed and pulled. The softness of the nightie on his skin mingled with the inner sensations.
'That's it darling....just lie there and leave everything to me....Honey it feels so nice fucking you....you go right ahead and cream for me whenever it feels like you're going to get wet."
"Ohhh Marilyn...I like it...it scares me to say it...but it feels good."
"Just like sleeping in your nightie and panties....Hmmm baby?...the feeling of the softness sleeping in nightgowns and tulle babydoll's is sooo addictive....once a girl starts wearing them she'll always want to be in nighties. "
It was the only sound in the bedroom slapping against his butt the noise sounded out. It shouldn't feel like that yet his nipples brushing against the nightie's fabric made them come alive.
Jack knew if he said it Marilyn wouldn't look at him the same way any longer.
"Marilyn....my nipples....Oh god your cock feels nice....can you touch them...please?"
"Sure honey...I'm just going to push this in a little deeper...it's going in and out so easily...that's it just lay there...damn you know you have all 6" inside you...I'll do better than kiss them...pull your nightie up darling and turn a little...I don't want to take my cock out....that's it....sweetie they look delicious is there a little jiggle to them?...here feel this."
Her mouth dropped down surrounding his areola with as much tension as the woman could muster she pulled the nipple past her lips. Inside she flicked her tongue and playfully teased the nub with her teeth.
Arching his back he pouted his lips looking so girlish as he did it.
"Oh my panties...I'm getting them wet...Eeewwww your cock...you're making me climax."
"Yessss that's my honey...don't worry I have plenty more panties for you to wear ...panties along with other lovely lingerie too."
"All things feminine....the Everleigh twins are on the air."
Trixie always made the declaration before they started. The two were wearing pretty corset's and stockings to go with their look as beautiful Cd's as Trixie and Matilda readied to record their latest Everleigh sisters ATF 'All things feminine' podcast. Even though no one would see them each took it upon themselves to look their best.
Naoma adjusted the sound on her laptop before putting in her earbuds.
"So Trixie I was reading this piece out of the Chicago Sun-times Dear Abby column October 15th.
Looking at her Matilda made a motion like her hands were shooting off 2 pistols.
"Yes you know ...Chicago 'bang bang'....Al Capone...gangsters ... speakeasys... brothels ....our namesake...The real Everleigh sisters....any way it seems a husband has upset his wife....she writes...Dear Abby my husband and I have been married for 11 years....yada yada yada...recently he discovered he likes to wear women's clothing...it started with wearing women's underwear under his clothes and has quickly progressed...."
"Join the club...what took him so long?"
"Now Trixie be nice...any way ....yada, yada, yada...I'm terrified this is the beginning of the end of our marriage."
"So what was Dear Abby's response?"
"She suggests the woman learn all she can about crossdressing..."
"My first wife would have benefited from doing that...maybe we'd still be married .... then again...I wouldn't have met you Matilda."
"Dear Abby goes on to say 'more men than you think may engage in it'..."
"I'd say we are definitely engaging in it..."
"She suggest she reach out for an excellent support group called the Society for the second Self....Tri-ess...its website ... tri-ess.org"
"They are a shelter in the storm of ignorance and intolerance...Ok so that ends our public service announcement portion of our show...."
"Now Trixie...the thing is I can't understand why more women don't accept it...why lock him in a chastity cage and let him dress and clean the home...throw in a little vagina worship and bingo happy marriage....after all 'every woman needs a housewife'."
Naoma couldn't help yet think it was a timely statement.
End of part 4 ...