Torment Ch. 05

Barbara still didn't have a pair of women's sneakers for general wear around the yard and garden. She had been meaning to get Barbara her first pair as she didn't have them yet.

Sasha knew she also needed a new pair of women's sneakers and hoped her femme husband would find shopping as fun and enjoyable as she did.

Shopping alone could sometimes be boring but shopping with a friend was almost always more fun.

**

The drive to the ferry was quick and traffic was sparse for that time of day. The line of cars was short and they were able to board the next ferry easily. They stayed in the car for the 30 minute crossing to the city. Both women...Sasha smirked; her femme husband was certainly a woman right now, were playing on their phones as the trip passed mostly in silence.

Sasha was momentarily distracted from her phone when she took a second to admire his legs. When he got into the car she saw how he scooped the skirt under him when he sat down so as not to wrinkle the skirt. Very important as it was nearly impossible to get a crease out of leather once it was folded. Then there was the way she fussed with the hem of her skirt, just above her knees. She watched as she also ran a hand over her leg, perhaps feeling the silky smoothness of her stockings.

Her gestures and mannerisms were so cute!

"We should probably discuss your voice." Sasha said, breaking the comfortable silence.

"My voice?"

"Yes, I loved the breathy Marilyn Monroe voice you did yesterday but not sure how believable that is."

"Well, what should I do?"

"To lighten your voice, just speak softly, and more from your upper chest." Sasha advised. Sasha spoke reassuringly so as not to cause Barbara to feel any trepidation.

"I think you were really onto something last night and with a bit of practice we can have a voice more feminine and less...androgynous."

"I do have a question.' Barbara asked, practicing her voice.

"What is it?"

"The contents of my purse. I understand why the hairbrush, lipstick, mascara, and simple eye-shadow palate, would be in here. I also have my phone and my wallet. But could you explain to me why you have a pair of thong Panties, a condom, a small bottle of lube, and...tampons?"

Sasha burst out laughing.

"Well not that I think you'll need them but a girl should always have those things. You never know when or if you will need a cute guy."

"You remember the rules though; nothing that breaks the law or could result in arrest." Barbara replied levelly.

"I know, so no, I'm not going to ruin what we have over a reckless something" Sasha reassured her "but it's still fun to fantasize."

Barbara blushed furiously.

"And tampons are 'just because' as well. Imagine you are in the ladies room and someone needs one. Complete strangers will hand one over. It kind of funny, even if the woman is your worst enemy, if she needs to borrow a tampon, you just hand it over without comment."

**

"Don't you see anything you like? There are a lot of really cute dresses here." Sasha commented, perusing the racks of clothing. They had been in two stores already and while Sasha had found things she wanted her feminized husband had not. So far she had claimed that nothing interested her.

Her apparent disinterest broke quickly as Sasha saw her reach suddenly into the rack and pull out a dress.

"This one." Barbara said with barely contained excitement.

Sasha looked to see Barbara was holding a golden sequined mini dress. She saw a look of wonder on her femme husband's face as he was admiring the gown. The sequins of the dress were sparkling in the store lighting. The short dress looked figure hugging

"When would you wear it?"

"Christmas!" Barbara said seriously.

Sasha smiled. "Yes. That would be perfect for the holidays." Sasha admired the dress. The holidays were still 5 months away, and Sasha hadn't even begun to think of what they would do for Halloween, much less Christmas. But the dress did look cute. If it fit it would be perfect.

"You need to try it on."

Barbara's happy face fell slightly and she started to put the dress away.

"I'm not sure I can...the changing rooms..."

Sasha acted quickly. She took the dress and put it back in Barbara's hand. She grabbed the next dress one size up as well. She then took her by his hand and started moving her towards the changing rooms.

"Yes you can. You are beautiful, and you can pass. No one will know. You are going to try these on and see which one fits best." Sasha spoke softly. The store wasn't crowded but there was no need to draw attention. She spoke casually as she easily gave Barbara the reassurance she needed.

Barbara didn't look convinced.

"It will be ok. I'll go in with you." Sasha reassured. "Besides, you helped me in the other stores. It's not that different for you to try on something than it was when you were with me trying things on."

Sasha led the way as Barbara followed, their heels tapping reassuringly on the tile flooring. Sasha had with her another dress besides the two gold sequined dresses Barbara would try on. She had selected a black body con mini dress earlier as it was on sale. She had originally intended to try and coerce Barbara into trying it on as a way to experience the thrill of trying on new clothes but now that she had found a dress on her own it would not be necessary.

Once they checked in with the attendant they made their way to a changing booth. Once the booth door was closed Barbara stripped down to her bra and panties and laid her blouse and skirt on the bench. Sasha admired Barbara's figure.

Standing before her in bra, panties, thigh highs and heels Barbara looked hot! Sasha especially like the way her panties clung to her butt and the way her panties covered her bulging cock cage. The cage, invisible under her skirt it was now prominently displayed. Sasha found the eroticism undeniable seeing her caged, femme husband stand demurely before her in her intimate attire.

Dressed as she was she also displayed a feminine athletic physique. Her long strong legs and firm round bottom lengthened and emphasized by her heels.

Sasha noted Barbara's waist. While her waist to hip ratio was acceptable, halfway in between the feminine and masculine ideal, it could be better. Sasha found that she was idly wondering if a basque or waist nipper would help cinch her waist and bring Barbara's figure closer to the feminine ideal.

Trying the black bodycon dress first both she and Sasha were disappointed.

The dress would have looked fantastic except the lump formed by her caged cock was proudly bulging near the hem of the dress. If she wanted to parade with her caged cock clearly outlined then the body con dress would certainly allow for it.

Sasha was at least pleased with her eye for sizing as the dress otherwise fit Barbara perfectly.

Barbara doffed the black bodycon dress and now tried on the gold sequin dress. It was also a short dress. Once Sasha zipped up the back zipper the hem only came to mid thigh. The flare of the dress skirt section did cover her caged penis and showed no evidence of her bulge. The two of them went out into the common area of the changing room to admire it in the mirrors.

"This size fits well." Sasha noted. The dress Barbara had picked fit perfectly. There would be no need to try on the next size.

Barbara turned side to side to admire the dress. It was very flattering to her figure. The sequins sparkled in the room lighting.

"Yes." Barbara looked enamored with her reflection.

"Maybe some shoes to go with it?" Sasha prompted.

"Yes. That would be nice." Barbara replied, still admiring herself in the mirror.

Sasha smiled. She knew they would have fun together!

**

Barbara sat in the passenger seat as Sasha drove them to their next destination. It came as a surprise to her how much fun this shopping trip really was!

Initial nervous and hesitant Barbara followed Sasha's lead as she was led through the stores. The thrift store was a bust as nothing there that day interested either her or Sasha. The discount department store had a variety of wares but nothing there truly captivated her or caught her attention. Sasha had purchased a few home and house ware items but nothing really memorable.

The flagship luxury department store was an entirely different world altogether. Everything was so nice and new, yet so much more expensive! Finding the gold sequin dress was an amazing experience. Even the bag the clerk placed the dress into was nice. The clerk carefully wrapped the dress in tissue paper and then placed it into a heavy paper bag with string handles and the store logo printed upon it.

Walking away with the bag in her hand felt so...intense...good...arousing!

Being dressed en femme and out and about during day time Barbara was highly aware of her surroundings and did notice when other women noticed her. She noted how they seemed to look at her legs, as if evaluating her, but then look away and continue with their own interests and shopping. Barbara didn't see any other women wearing stockings and decided that was what they noticed.

The oddest part were the men. They also noticed her legs and seemed to stare more...appreciatively. One older gentleman actually approached her and complimented her.

"It's so sad. You don't see women these days taking pride in their appearance and dressing well." He said. "You look very pretty and well put together. Such a shame young women don't dress as well as they did back in my day."

Sasha had watched from the side and looked conflicted. On the one hand she seemed to want to burst into laughter, while on the other hand she seemed...proud. She seemed to preen a bit when Barbara was complimented.

Barbara also could not help her intermittent arousal. Trying on the gold sequin dress and posing before the mirror caused her pain as her cock cage constrained her bodies attempt at an erection.

It happened again after the compliment from the elderly man. When the man left Barbara turned and saw Sasha's pride. Seeing her happy Barbara's cock once again tried to become erect, with predictable results.

Barbara hardly ever got erections during the day, at least not that she noticed. When at work or when out and about as her normal male self she never really thought about it. But en femme, dressed up for Sasha, she found her body felt arousal more often and her cock was trying to get hard a lot!

She also admitted to herself that the bra, the breast forms and their weight upon her chest felt incredible. The way they would jiggle and sway when she moved caused intermittent arousal.

There was also the soft feeling of her panties, which had somehow wedged between the cleft of her bottom. Soft gusts of cool air would occasionally waft up under her skirt and past her panty clad bottom, surprising her each and every time with a pleasant sensation upon her exposed skin.

Then there was the way her legs brushed past each other and the soft swish sound of her thigh high stockings when they occasionally brushed nylon against nylon. The feminine tapping sounds of their high heels on the tile floors or concrete sidewalk.

The moment she caught her reflection walking past some windows, seeing the flip of her skirt and the sway of her hips wearing high heels induced in her walking stride, was indescribable.

Barbara had to admit it. Going out dressed en femme, passing as a woman...the experience was amazing and just so much fun!

Half way through their day they stopped for a light lunch. Barbara appreciated the rest. Her heels were comfort fit but still, she and Sasha had been on their feet almost the entire time.

"Have you had a good time?" Sasha asked. She had ordered their food and they were waiting upon the waitress now.

"Yes. God I was so nervous at first but this day has been so incredible. I can't believe that no one has read me."

Sasha smiled again. "Your doing great with your voice and your makeup is perfect. Without makeup, sure, it would be obvious, but your androgynous features help. Once you've contoured though, that's the point where you look feminine. The rest is just icing on the cake."

Their conversation paused as their food arrived; a Cobb salad for Barbara with an iced tea while Sasha savored a club sandwich with lemonade.

"You really haven't found much though." Sasha commented.

"I tend to think that separates work best for me." Barbara stated. "Most of what we saw was amazing but it's hard to justify the expense. Where will I wear it? And it's just so cheap and convenient to order skirts and tops on line."

"You just like showing off your legs. If I left it to you you'd have nothing but miniskirts and crop tops." Sasha accused.

"Those are for home, although I can't say that I haven't thought about it now, especially after today." Barbara teased back.

"What's next on the agenda?" Barbara asked.

"I've planned a shoe store, then a lingerie store, a vintage clothing store, and then an adult store." Sasha commented casually between bites.

Barbara looked concerned when she mentioned the adult store, and then simply shrugged her shoulders.

"Fuck it. I'm game." She said, sipping her iced tea.

**

At the shoe store Sasha noticed Barbara's attitude change. She was really into it and was searching for something like a woman on a mission.

"What are you looking for anyway?" Sasha asked. She had found sneakers for both of them as well as a new pair of heels that at that moment she was currently trying on and walking around in. They felt comfortable, looked cute and were reasonably priced. She decided to buy them.

"I'm not sure but I'll know it when I see it." Barbara answered.

"So you don't like any of these?"

"I like them all but I know what looks best on me." Barbara answered seriously.

Barbara suddenly paused when she found a pair of red slingback heels. She selected a pair in her size and took them to a chair to try on. She had also found a pair of sparkly gold stiletto pumps with a four inch heel.

"What are those for?" Sasha asked. She was pleased that Barbara found something and was curious if Barbara was picking them because they were cute or if she had a plan for them already.

"The red are for the tartan red mini skirt at home, and these are for the new gold sequin dress we bought." Barbara answered.

Sasha just gave Barbara a look and smirked. She looked so happy with her finds and eager to try them on to see if they fit.

"I'm a simple girl, I have simple tastes." Barbara confessed, seriously.

**

After buying their new shoes Sasha took Barbara to the Victoria's Secrets Store. Sasha knew Barbara loved their panties and bras and made her purchases on line but there was always something special about going to a brick and mortar store. The lighting, the displays, the selection and actually seeing things before deciding all made a trip to the store a more fulfilling experience compared to buying on line.

Sasha and Barbara both made several purchases and Sasha was not mistaken in her impression of Barbara when she left the store happily carrying her pink and white striped bag full of new panties and bras.

Dropping their purchases into the trunk of their car they walked to their ext destination. A few more doors down was the vintage clothing store specializing in women's clothing from the 1940s, 50s and 60s as well as new vintage style intimate attire.

There was no mistaking that look of amazement on Barbara's face. The vintage clothing store was definitely attracting her interest. She walked slowly through the aisles, clothing racks and displays, almost like a girl in a candy store, not sure what to look at first.

Sasha let her enjoy herself for a bit and followed her through the store. Barbara seemed to gravitate to the 50's era clothing. She gently, delicately searched through the racks of dresses. Once again, just like at the flagship store earlier, she appeared almost gleeful when she came across something that caught her eye and interested her.

Immediately, Sasha appeared and took the lead, guiding her to the changing rooms and made her try it on.

The 50s style dress had a blue floral print, a pinched waist, an exaggerated hourglass silhouette, rounded shoulders, exaggerated hips and a full skirt ending at her mid calf. The dress had short sleeves that covered her arms almost to the elbow. It also had a wide ribbon like design around the waist and a large bow at the back that made her waist appear smaller. The dress bodice had three large buttons up the front and a v-shaped collar that plunged down to between her breasts, showcasing her décolletage.

Sasha adored the bow. She really wanted to buy this for Barbara and have her wear it for her amusement and adoration. Sasha felt that ribbons and bows worked really well for her femme husbands presentation.

"It doesn't seem to fit too well though." Barbara remarked as she checked out he reflection in the mirrors.

"You need to have the right bra on as well as the petticoats. Wait here!" Sasha said as she darted out from the changing rooms. She quickly selected a white petticoat that would loft the dress skirt as well as a black bullet bra.

Joining Barbara back in the changing room she had her change out of her modern bra and into the 50's bra, slipping her breast forms into the new bra.

"You need a garter belt and stockings. Wait here again." Sasha found she was getting more excited. Darting out into the store she picked up a pair of white vintage high waisted nylon panties that had delicate black lacing details.

Checking with the store clerk she also took a pair of sheer champagne stockings with a black thigh hem and the black 50s style 6 strap garter belt back to the changing room. She was pleased to see Barbara had already removed her shoes and her stay up thigh high stockings in anticipation. With the new vintage panties she had to remove her hipster panties Sasha noted Barbara's caged cock appeared to strain enormously against its confinement.

Once fully dressed in her vintage intimate attire, high waisted panties, garter belt, champagne stockings, petticoat and bullet bra with its aggressive underwire, Sasha helped Barbara as she stepped back into her dress and lift it up onto her. Sasha heard Barbara's gasp of discomfort.

"Cage tight?" Sasha asked, whispering.

"Yes." Barbara answered, also in a whisper.

"Understandable. This ensemble is hot." Sasha teased as she zipped up the back zipper of the dress. She fluffed out the skit so it lay evenly over the petticoat. Barbara and Sasha went back out into the common area to check out her appearance in the multiple large mirrors.

Both of them were amazed and inspired by the flattering effect the dress had on Barbara. With the exaggerated hips and narrow waist, and the petticoat lifting the dress skirt, she looked like a well groomed, healthy and sexy woman. Her blonde wig and subtle makeup worked out well with the vintage dress, even better than with her original grey skirt and top.

Sasha could completely understand how her femme husband would be excited from seeing the vision of loveliness in the mirror. She felt ambivalence as she hoped his cage was causing him some discomfort at the same time hoping it wasn't too much discomfort.

"If you'd like to wear it out we do have vintage heels to complete this look." The store clerk said, surprising them and interrupting their admiration and fascination.

Barbara gasped slightly as she turned side to side in the mirror, admiring the dress, the strain on her cock struggling against its confinement distracting and arousing her more.

"Yes. That would be nice."

**

Walking back to their car from the vintage clothing store Barbara and Sasha both noticed the increase attention Barbara received. Carrying her previous outfit of grey leather skirt, top, bra, panties, heels and thigh highs in the store bag she stood out among the many people going to a fro in the downtown shopping core.