Torment Ch. 03

The following contains themes of feminization, cross-dressing, sodomy and other adult topics, so before we begin here are the usual disclaimers. This is porn, you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is. You're an adult, life is short, find porn you like and read that instead. But if this is a style you enjoy, then feel free to comment and provide constructive criticism and feedback. I need to grow as an author and honest constructive criticism is always welcome.

**

Since dressing him up that one night Sasha couldn't stop thinking about it. His figure was truly amazing, fit and toned. His full butt and narrow waist were half way between the masculine and feminine ideal. Her husband had been athletic all his life, mostly a runner but with lots of weight lifting mixed in, his ectomorphic body style meant he never bulked up. Indeed, both of them now in their 40s with grown children now out of the house still looked 10 years younger than they really were. Both of them still kept in shape and worked out.

Sasha's workouts also focused on maintaining health and fitness. She was blessed perhaps that she was only over her ideal bodyweight by 10 lbs; for a fit and healthy woman her height that was really saying something. She blamed those few pounds on having had children. Despite being her own worst critic her figure looked amazing and femininely soft. Her breasts had barely any sag, a fact she knew was entirely luck or genetic rather than anything she did with diet and exercise but still she could appreciate the small miracles.

Her thoughts wandered back to dressing up her husband. Truly she worried that she was becoming a little bit obsessive about it. Her thoughts were sometimes tormented as she struggled to reconcile her fascination with reality. She needed reassurance from her husband that she wasn't pushing him too far.

She struggled to reconcile her desires and her fascination with domination and worried how it affected what she felt was the innate goodness that she strived for in her life.

Making her husband into her feminized dress up doll...Sasha's breath hitched and she took another deep breath as her arousal swelled inside her. All her life she had always thought than men should be manly and women should be girly. And then she happened upon chastity for him, which led to panties, and then to dressing up, each a stepping stone to greater feminization.

Sasha loved the contradictions in having her husband dressed femininely. She did feel tormented at how his feminized appearance affected her arousal. The control he gave her letting her dominate him.

Sasha's thoughts paused again. That was it!

She now realized that was exactly what it was. She liked...no...she loved having control.

She loved the feeling of power and control. She knew the power she was given came from the consent of her husband but for some reason that made it even more arousing.

**

Sasha woke to the sounds of her husband's discomfort and a glance at the clock showed it was only 2 AM. He had been tossing and turning and now lay on his back probably trying and failing to go back to sleep.

Sasha knew his torment was from his captive erection struggling to find freedom from its plastic confinement. She grinned but feigned sleep as her husband sighed and apparently resigned himself to getting up out of bed to go urinate and relieve the strain on his cock. She listened as his bare feet padded across the floor to their master bathroom and glanced over at the last minute to appreciate his panty covered ass.

Quietly he closed the door, probably thinking she was still asleep so as not to disturb her or wake her. Sasha heard him lower the toilet seat. With his cock caged he had to sit to pee just like a woman.

Before discovering chastity Sasha had always been annoyed when he woke her up but after discovering chastity Sasha relished these moments when she was assured of his chasteness and the simple reassurance of his restraint from self pleasuring.

His cock was saved and reserved for when she was ready and wanting him and frivolous physical indulgences were prevented.

Tomorrow was her massage night and Sasha was eager to enhance the experience with beauty and body care routines she had planned for him.

During the past week she had taken steps to improve his appearance for the upcoming weekend. She made sure he shaved his legs and body. That was quite the feat as his usual body hair was coarser and more prolific than a woman's body hair. He had used his beard trimmer electric razor to clip back all his body hair before shaving with a disposable safety razor.

For as long as she had known him he had always given maintained a porn star trim. His pubic hair was clipped back so as to make his already impressive eight inch cock look even bigger. Now the complete shave and removal of his pubic hair hadn't really changed that. His shorn cock and balls did make his cage look more intimidating however so that was something.

The overall effect afterwards on his look was nakedly impressive. She urged him to use lotion to sooth his dry skin from the soaps and shaving creams he had used to remove all body hair and noted his appreciation for how smooth and silky his skin was after application.

Sasha heard to toilet flush and the lights switch off as he quietly returned from the bathroom, came back to bed and lay back to fall asleep.

Now awakened, the anticipation for their upcoming weekend kept her awake for quite some time.

Sasha was a very feminine woman. Growing up she played with dolls as a young girl, took to cosmetics, makeup and boys at an appropriate age, and never had any serious flirtations with girl-crush lesbianism.

Well, except for that one time, at band camp...

Sasha shook her head to clear away past reminiscences to focus on her present interest, her sudden attraction, newfound passion and devotion to dressing up her husband. She was eager to play with her husband, feminizing him and making him up into her new toy, her feminized husband.

Sasha took a deep breath to calm herself and bring her lustful emotions under control. She had to restrain herself. She knew today she would go out shopping again as she needed to buy a few more things to make their latest adventure successful.

Sasha even noticed a change in her behavior when shopping. Before when she went shopping for things for herself it was routine, mundane, typical and a bit boring. Now though when she saw something cute she would think and wonder if her husband might like it or how cute something would look on her...him...ugh!

Buying new outfits for the both of them brought its own sense of thrills.

Sasha purchased cosmetics and a wig locally but finding heels that fit meant shopping on line. She didn't want to kill him on his first attempt but stilettos are stilettos and she really wanted to see the feminizing effect they would have on his legs and ass. She did feel proud for exercising some self restraint and only buying 3" heels and not the 4 or 5 inch heels she really had her eyes on.

The glossy black 3 inch heel stiletto pumps would pair well with almost any outfit or ensemble she...he, dressed in. They had been delivered only the day before and she quickly squired them away in the closet so her husband wouldn't see them until she was ready.

**

"You don't want me to wear the tartan pleated mini and blouse again?" he asked.

Sasha pretended to sadness. "You look so cute in your school girl outfit. I've even ordered a tartan COVID mask to match, but tonight I have something new for you."

Sasha saw the glimmer of curiosity in his eye and playful smirk on his mouth.

"No, a new scene deserves a new outfit." She said as she retrieved and revealed the dress with a flourish. "I found this today and immediately thought of you and wanted you to have it."

Sasha held up a pink and white floral print A-line dress with sweetheart neckline and flutter sleeves.

"I know it's not spring anymore but I saw this on sale."

Sasha really did love this style, not for her though. It was actually too girly for her taste and that made it perfect for how she imagined dressing up her husband. She liked it best as it was the most suitable and entirely flattering for her presentation; and Sasha's appreciation.

"You've really thought this through." He said, noting the completeness of the outfit.

Sasha had selected and purchased for him a new pale pink floral panties and bra set, and had splurged for breast forms to fill out the bra cups; no more stuffing with socks. Opaque sheer thigh highs would give him feminine legs, especially now that his legs were shaved smooth and silky from lotion.

As he put on his intimate attire, bra and panties, Sasha helped and made sure the breast forms sat properly in the bra cups. She had him put on his thigh highs next. The silicon bands would let the thigh highs stay up on their own. She had him step into the dress and took place behind him.

Once she zipped up the back zipper of his dress she checked to make sure the dress flattered his figure. She was relieved at how perfect it fit. The fit over his shoulders and bosom clung perfectly into his narrow waist and then flowed back out over her full bottom. The hem of the dress sat just above her knees.

Satisfied that the dress worked she had him sit at her vanity and the real work began; a full and complete makeover.

Sasha had to use orange concealer to hide his beard and prevent beard shadow from showing though his foundation. She had successfully matched the shade of foundation with his skin tone, but then went one shade lighter to smooth and even out his complexion to create the blank canvas she wanted as a starting point.

Sasha had contoured his face according to his facial profile to maximize the feminizing effects of bronzer and highlighter thus making his appearance rounder and softer. Blush gave a healthy glow to the apples of his cheeks.

Eye makeup was always the hardest, but opting for a 'more is better' attitude she went for a dramatic smoky eye appearance with cats eyes to draw attention to his lovely blue eyes.

Eye liner to boldly outline the blue and gold smoky eye-shadow and mascara for long lush lashes finished the look and really made his eyes pop!

The final touch of course was his lips. Sasha took lip liner to outline the edges of his lips and draw details that would show through his lip stick. For his lipstick she selected a deep rich red color, of course, and once finished his normally full lips seemed fuller...and much more kissable.

Sasha helped him put on his wig. She had splurged and spent a fair amount of money on a wig with real human hair. The long luxurious blonde locks cascaded in curls from his head down to his shoulders. The style framed his face with a stray lock of hair drooped over one eye adding a demure presentation.

Stepping back Sasha could only admire her handiwork as the person looking back at her looked nothing like her husband and everything like a beautiful young woman. Fully made up and transformed her husband looked like a 25 year old college coed.

Sasha watched as he slipped his feet into the new pair of high heels, and then stood up to admire her transformation in the mirror. His lips parted in surprise as she finally turned to the mirror and saw the finished presentation. Idly her hand went up to touch her face, gently so as not to ruin the makeup, as if to confirm it really was him in the mirror.

"Wow. I can't believe it."

Sasha said nothing. She felt almost awestruck at how well her husband had turned out. She looked amazing!

"Go ahead and stand up." Sasha finally found her voice.

Sasha watched as he took a moment to find his balance in his...no, her new heels. Her husband now stood up and they both admired the full and final presentation in the mirror. Her husband even turned side to side to check out the dress fit on his thin full feminine form causing the skirt portion to flare out gently.

"So this is what it feels like to be 6 foot tall."

The heels had really done amazing things, her posture was better, her back was straighter, her legs looked longer and frankly amazing, even her ass looked rounder and fuller.

Sasha mentally blinked again as she realized that when she thought of her husband dressed as 'she', she could only think how natural and comfortable it felt to think of her this way.

"We should come up with a name."

"A name?"

"Yes, a name for when you are dressed up, a name for your feminine persona."

Sasha and her husband both admired her reflection in the mirror.

Sasha admired the demure yet slutty presentation and the name that came to her nearly made her giggle.

"You look like a Barbara." She proposed.

"Barbara?"

"Yes...Barbara Jean." She proposed, more insistently, as she played with the flutter sleeves of the dress and gently arranged locks of hair from the blond wig to drape over the bosom while the bulk of the hair hung behind her back.

"Barbara Jean." He said, sounding out the name. "Sure...I like it."

Sasha's smile could have lit up a room.

"Well, come on then Barbara. It's time for you to make dinner."

**

Sasha followed Barbara around as she cooked dinner and set the dinner table, noting how she placed Sasha at the head of the table and instead of tabling her place setting at the other end of the table, she set her own plate so she would sit side by side, in a subordinate position.

Dinner was actually really good as well. Barbara made a simple chicken parmesan dinner with Caesar salad and garlic bread sides served with a complementary red table wine. Thanks to all the practice she was getting Barbara was becoming a commendable cook.

Once dinner was over Barbara served Sasha coffee with Bailey's Irish Cream and then cleared the table, washed the dishes and cleaned the kitchen. Everything was spotless and stowed neatly away, the dishwasher running quietly, before it was finally time for Sasha's massage.

Stripped down and laying on the massage table Sasha thoroughly enjoyed the relaxing hour long whole body massage. She thoroughly enjoyed watching Barbara as she moved around her, her poise, the flutter of her dress as she tended to her body, she was just so cute!

When her massage was finished, rather than immediately shower to wash off excess massage oil Sasha had other plans. Her excitement was boiling over.

Sasha wasn't done. She needed...wanted, to lay the groundwork for future plans. Sasha rolled off the massage table and stood naked, her body coated in a sheen of massage oil, Sasha made Barbara stand before her. She put her hands up under Barbara's dress and taking her panties in hand, lowered them down to her ankles. Next, she lifted up the hem of the dress exposing Barbara's caged trapped penis struggling and frustrated trying to reach tumescence.

Unlocking the cock and removing and setting aside the cage she stroked Barbara's cock until it was full and firm in her hand. She kissed Barbara full on her lips, smudging her lipstick and only making her appearance that much hotter. She was a hot mess! Sasha broke the kiss, dropped to her knees, and kissed Barbara's...her feminized husband's hard cock, then opened her mouth and took her hardness into her mouth and sucked.

Sasha enjoyed the look of surprise and pleasure on Barbara's face as her mouth pleasured her cock. She kept up her fellatio drawing out Barbara's pleasure. When Barbara's eyes closed to savor and enjoy the oral attention Sasha was ready to act.

Her husband had never cum from a blow job before so she often didn't care to try. He considered it simply as foreplay. Sasha blamed his prior frequent masturbation for diminishing his cock's sensitivity. That irritated her more than she cared to admit and helped justify her decision to keep him chaste.

Now however, she was eager to try something new. Something that she had read about as a way to encourage her feminized husband and make him cum. While giving Barbara her blow job Sasha wet her finger with saliva and oil and slipped the finger into Barbara's ass.

Sasha looked up as Barbara's eyes opened wide in surprise. Her hands went to her ass and pressed against Sasha's hand, protected by the dress skirt. Sasha pushed her middle finger further in and buried it up to the second knuckle of her feminized husband's tight asshole.

Thrusting her finger in and out of Barbara's ass, Barbara made many ineffectual attempts to stop her. Sasha worked her finger in and out of Barbara's ass. Pleasuring and massaging her sphincter until suddenly her knees shook, then her breathing hitched as a soft moan escaped her lips and grew into a cry of pleasure. Barbara's hands now went to Sasha's shoulders and held on as her orgasm took her.

Sasha thrust her middle finger in deeply, as deep as possible, and let Barbara's cum spew into her mouth. She didn't swallow, holding the cum in her mouth until Barbara's orgasm subsided. Sasha withdrew her finger, let the cock slip from her lips and mouth and as she pulled up Barbara's panties she spit the cum from her mouth into the gusset of Barbara's panties. She stood up, pulled Barbara's head into a kiss, heedless of any residual cum still on her lips, tongue or mouth.

"I'm going to take a shower. You clean up as usual." Sasha ordered, after breaking off the kiss.

There was only a short pause as Barbara was slowly recovering from cumming.

"Yes Mistress."

**

After that night Sasha noted how much more submissive and eager her husband became. She still kept him in chastity of course, adhering to the rules they agreed upon and let events unfold naturally.

One of the first changes she made was to now insist that he dress up for chastity when he came home from work. Sasha loved finding and buying him skirts and tops and while a full cosmetic makeover was usually saved for the weekends her femme husband made a sexy and cute bit of eye candy for her to enjoy after a busy day of work.

Of course the most important bit was finding out that he could be stimulated anally Knowing this fact made her want him even more. Sasha couldn't help it. She eagerly looked for another opportunity to express her love and expand their play into even deeper submission.

A few weeks later her husband had spent all day working in the yard. Towards the end of the day all the yard waste was burning in the bonfire pit. As the branches and sticks burned Sasha sent her husband to shower and change and as the evening grew long Barbara came out to join Sasha at the bonfire.

Barbara returned wearing a pleated denim skirt that went down to mid thigh, a teal cami with spaghetti straps, a bra with breast forms, panties and sneakers. Sasha loved her youthful feminine appearance and made a mental note to buy a pair of women's sneakers for Barbara on her next shopping trip.

They both added fire wood and naturally, a bon fire means adult beverages. Soon enough Sasha and Barbara were drinking. By firelight, Sasha played music from her phone as she and Barbara flirted and even danced with each other,

"Flaunt it baby!" Sasha shouted as she teased and encouraged her feminized husband as he danced for her in the twilight. She even caught a flash of panty as he twirled once before her.

Step inside

Walk this way

You and me babe

Hey hey

"You have such a nice ass." Sasha complimented. "Panties really do look good on you. I wish my butt looked this good."

"Don't be silly, your butt looks so much better than mine, curvier, fuller, softer..." Barbara replied.

"When is the last time you even wore boxers?" Sasha was curious. It occurred to her that she had been sending Barbara to work in panties for weeks now.