Torment Ch. 03

"Uh...I don't know. It has been a while." Barbara allowed.

"Wait here." Sasha suddenly got up and ran toward the house. A moment later she came back with a bundle of clothes. Before Barbara could even ask what she was doing Sasha tossed the bundle into the bon fire.

"What was that?"

"Your boxers."

Barbara looked into the fire in disbelief as the cotton boxers flared brightly.

"I can't believe you did that."

"You don't need them anymore. You look so good in panties."

Barbara felt the heat from the bon fire on the front of her legs as the cool evening air on the back of her legs wafted up under her skirt and teased her panty covered bottom and her chastity caged penis. Sasha's bold action aroused her and her trapped penis swelled in excitement and caused her discomfort.

"Maybe you'll let me make love to you tonight." Barbara whispered as she danced closely. Sasha looked over Barbara's cosmetics. This evening her application was fairly simple; yet lipstick, eye shadow and mascara had certainly done wonders to feminize her appearance and soften her facial features.

"Maybe I'll take you and fuck you in the ass." Sasha teased back.

"I'm not that kind of girl." Her husband replied, practically giving her a lap dance.

"I mean, you haven't even bought me dinner and a drink first. I need to be wined and dined."

Sasha chortled embarrassingly as she nearly spit out the wine she was sipping. But his response was the seed germinating a new idea.

"Maybe I will." She replied.

Maybe she would take him, as her, out to dinner and drinks. She'd look so cute in a cocktail dress.

And maybe just maybe she will introduce him to anal intercourse after all.

Sasha sat back on the lawn chair as her feminized husband danced for her. The cool evening air coupled with her arousal making Sasha's nipples pop erect above the curve of her perky tits. Yes, maybe she will.

**

Two weeks later.

"I can't believe I let you talk me into this." Barbara said.

"Oh you know you really want to." Sasha replied.

The two were making ready for their dinner date, Sasha at her vanity and Barbara over on her side of their master bathroom.

Sasha, amazingly, was nearly done. Despite taking extra care with her makeup for their date she still finished before her feminized husband. The extra steps he needed to take to conceal his bear shadow and contour his face took a lot more time and for once, Sasha was ready before he was.

"Just like a girl to take forever to get ready." Sasha taunted as she applied the finishing touches to her makeup while Barbara still worked.

"I'll be ready shortly, now go away and don't bother me." Barbara replied.

Sasha gave her husband a kiss and left the bathroom to him. In less than an hour he will have transformed from 'him' into 'her' and play time would truly begin.

**

Barbara took a deep breath and pressed on with her makeup. Part of her could not quite believe how she was putting on makeup and making the effort to look feminine and pretty for her wife. Not even a year ago dressing up as a woman, wearing makeup, and wearing chastity would ever have entered her mind.

Now, she was getting ready to present as a woman, wear a dress, and go out in public to dinner with her wife. Her penis flinched and strained against her cage in excitement. Life certainly could be strange.

She paused at the thought. In addition to her beauty routine Sasha had asked her to use an enema solution and flush out her colon. The simple treatment was effective as only two minutes after injecting the solution into her anus she felt the uncontrollable urge to evacuate her bowels. Now completely empty back there, she then douched her backside before resuming her beauty routine. Not having much time to think about it she pushed the strange occurrence to the back of her mind and focused on getting ready for their date.

Barbara finished applying foundation and noted that the orange concealer and foundation showed no hint of beard shadow. Having taken lessons from Sasha, Barbara moved on to contouring. She took the Bronzer and highlighter and applied them to her face. With practiced moves she used a beauty blender to blend the colors to minimize her brow and her chin. Once done she had lost most of her masculine appearance and her feminine persona was now showing through.

Eye makeup was the trickiest part for Barbara. She pulled up the YouTube makeup tutorial Sasha selected for her and followed its instructions verbatim. Once her eyes were done the last vestiges of her masculine appearance disappeared.

The last two parts certainly helped her appearance but also had a profound mental effect.

Careful application of lip liner as she had been trained and then lipstick made her full lips even fuller with a hint of plumpness.

Putting the wig on top of her head though was her crossing of the Rubicon moment. Once her blond hair was in place the transformation was complete.

Barbara looked into the mirror and was happy and satisfied with her appearance. There was now no hint of masculinity. Her caged cock throbbed painfully in its plastic confines.

Barbara exited the bathroom for the bedroom to get dressed. She was almost ready for her first date en femme.

**

Barbara was naturally quite nervous and Sasha made sure to make their date as comfortable as possible.

Sasha made sure to drive of course. Barbara had never driven in heels before. Sasha still stole occasional glances over to her feminized husband wearing her conservative black cocktail dress. The long 3/4 sleeves, tight bodice, boat neck A-line dress was simple and elegant. Her new black Victoria's secret bra and her breast forms clung to her chest giving her a full womanly bust.

Underneath her dress, hidden from view, dark sheer pantyhose covered her legs and bottom to her waist. Barbara also wore a Victoria's Secret black thong with logo waistband, her first thong ever that quite frankly felt amazing. She delighted in the feeling of the thin thong strap that delved between her ass cheeks and even gently brushed against her anal star. The thong front trapped her caged penis and held it snug. The restraining thong and the drape of her A-line dress kept her bulge hidden from view.

A new pair of 4 inch sandal strap wedge heels graced her feet, and allowed her painted toenails to be seen through the sheer mesh of her pantyhose. The color matched her fingernails, a warm rich red color, glossy and smooth, that also complemented her lipstick.

Sasha made sure Barbara accessorized with her pearl necklace and pearl earrings. Special clip on adapters had been ordered reminding Sasha that maybe she might want to get Barbara's ears pierced someday.

They drove slowly to their 8 o'clock dinner reservation at a secluded restaurant.

Barbara was most nervous about walking in and being seen in public but Sasha had no doubts. Barbara's presentation was flawless. Her fear of being noticed, recognized, 'made', or outed was unfounded and her other fear of what to do if approached by strangers never materialized.

Well, there were those two cute guys at the bar but Sasha politely declined the drinks they sent to her and Barbara at their table. There was no way she was about to share her girlfriend and cross dressed husband with anyone.

They both enjoyed their dinner, candlelight and a glass of wine setting the mood. Once Barbara relaxed they both flirted unashamedly with each other. It really was the perfect date.

Sasha made sure to take Barbara to a late night coffee shop so they could spend more time out of the house and in public together. As eager as she was to take her sexy feminine husband home and make love to her Sasha wanted to show off her beautiful girlfriend as much as possible.

The opinions of strangers didn't matter and yet she enjoyed seeing their looks of appreciation and lust. Looks she made sure to point out to Barbara. By the end of the evening it was unmistakable. Barbara was enjoying her time out in public, being admired just as much as Sasha was. Still, as the hour grew late Sasha was eager to take her girlfriend home and move this date along to more intimate activities.

**

Finally returning home, Sasha firmly escorted Barbara straight to the master bedroom.

Barbara couldn't help but smile shyly and eagerly and listened to the two pairs of high heels clicking quickly across the hardwood floors as she was led to their master bedroom. She let Sasha spin her around, embrace her and press her lips onto her own.

Barbara succumbed easily to Sasha's dominant aggressive kiss and was caught by surprise when she reached behind her to unzip the back of her dress. When Sasha broke free from the kiss Barbara let he dress fall off of her shoulders and down into a puddle on the floor. She now stood before her in her black bra and breast forms, black thong, black panty hose and wedge heels, pearl earrings and pearl necklace.

Barbara moved to remove Sasha's dress but Sasha surprised her by aggressively pushing back on her shoulders. As she fell backwards her legs folded at the edge of the bed and she fell roughly onto the mattress, her blonde wig splaying slightly like a halo around her pretty face.

Sasha smiled at her sexy feminized and chaste husband as her legs also splayed out when she was knocked back. She was just so pretty...and perfect. Sasha undid the side zipper from her black pencil skirt and let it fall into the pile of clothes on the bedroom floor. She doffed her white blouse as well, adding it to the pile.

Now wearing only her white bra and panties, opaque stockings and hold-ups she stood toweringly over her reclined feminized husband.

"I have a gift for you." Sasha smirked as she said it.

"What is it?" Curiosity and lust evident in her girlfriend's eyes and voice.

Sasha went to the nightstand, opened the drawer, and pulled out a pair of handcuffs. She noticed Barbara shiver slightly seeing the gleaming metal.

"Are those...real?" Barbara asked.

"Yes. Police quality, not a cheap fetish toy." Sasha relied gleefully.

"Now, put your hands out front." Sasha commanded.

Barbara held her hands out in front as Sasha clasped first one, then the other cuff onto her wrists. She took the key and locked the safety latch so the cuffs would not tighten accidently and cut off circulation.

She let Barbara admire the fetters now shackled onto her wrists for a moment before proceeding.

"Move to the center of the bed and lay on your tummy." Sasha ordered next.

Barbara awkwardly rolled onto her tummy and crawled awkwardly, centering herself on the king sized bed.

Sasha took a moment to herself to admire the full panty clad and pantyhose clad bottom poking up before her, the firm backside, narrow waist, and the bra straps holding Barbara's fake tits in place. Her blond hair cascaded behind her back until Barbara unconsciously flipped her head to put all her hair to one side.

Sasha now crawled onto the bed as well and took Barbara's wrists by the handcuff chain and moved her wrists and arms to the head board. Pulling a short chain attached to an eyebolt bolted to the headboard and hidden by a pillow, Sasha took a small padlock, locking the chain from the head board to the handcuff chain.

"There, now you're not going anywhere." Sasha smirked vivaciously.

The look of surprise on her feminized husband's face was priceless.

"When did you do that?" Barbara asked.

"Oh, the other day, but don't you worry your pretty little head about it. It's only for your use anyway." Sasha giggled mirthfully. She had been waiting for the right moment to use that 'pretty little head' line for quite some time now.

Sasha left Barbara to struggle gently against her restraints as she walked into their closet and opened their pleasure chest. The small decorative locking chest that held all their toys they had acquired over their years of marriage. From inside she retrieved something new. Something she was eager to try out tonight...if her husband let her.

"What are you planning to do?" Barbara asked. He was a bit nervous and pulled gently on the steel handcuffs. The chains clinked softly as the links pulled against each other.

As she heard the taps of Sasha's high heels on the hardwood floors she pushed up on to her elbows and looked back over her shoulder to the closet door where Sasha had just gone and come from...and gasped in surprise.

"Like what you see?" Sasha asked mischievously.

Standing by the side of the bed Sasha, in her white bra, white panties, sheer thigh highs, garter belt and heels now sported a solid black leather belt that held a white dildo jutting obscenely from her groin area. She held a bottle of lube in one hand and waggled the dildo with her other hand.

She noticed as Barbara, he feminine husband shivered nervously.

"Wait, are you going to..." Her words trailed off.

"You did say that if I wanted to fuck you then I'd have to wine and dine you first."

Sasha watched his cheeks blush from embarrassment. Damn he is so cute like this!

"Won't it...hurt?" She asked, her voice quivering slightly.

"Sodomy? At first, if you are not careful, it can be too much Ow! and not enough Aaahh..." Sasha complained. "But you know that already from when we have anal sex."

Sasha grinned maliciously. She and her husband didn't often care for sodomy. Butt sex was absolutely a 'must be in the mood' kind of activity. Still, often when he insisted and pleaded she would yield to his persistence and make anal a part of their sexual activities and intimacy.

"You don't think turnabout is fair play? I do it for you."

Barbara merely swallowed nervously.

"I think you are interested and that maybe you are afraid that it is your turn to submit to my lust and desire for a change." Sasha rationalized for him.

Sasha watched her femme husbands face carefully. She still looked nervous, but also, interested?

"I bought this Strap-on just for you and you alone. I want to penetrate you and make love to you the same way you have fucked me before from time to time. I want to make you feel what she I feel when you make love to me." Sasha spoke softly so as to entice her husband into accepting her offer.

Sasha watched her swallow nervously again. This gave her an idea.

"Maybe we should start out easy." Sasha moved and took position between the head board and her feminized husband's beautiful face. She straddled over his arms, spreading her legs wide apart, her back and her heels against the head board, kneeling, resting her butt down onto her calves.

The strap on cock now pointed directly towards Barbara's face.

"Maybe you would like to see it up close first...maybe you'd like to suck my strap on cock."

Sasha waited. It was a serious moment. If he said no, she would respect that and would be sad but would let it go. She almost missed it when he nodded his head yes.

Sasha's heart leapt inside her chest. She watched his face as he gazed upon her strap on, getting an up close and personal view of the dildo jutting out from her groin. Her excitement at his acceptance made her juices flow and she felt a distinct sensation of wetness between her thighs soaking her panties.

"Nervous?" She asked as she brushed her blonde hair aside from her face.

"actually, yes..."

"You don't have to." She said softly, not really wanting him to quit. "Maybe I really shouldn't have surprised you like this."

"No...it's ok...it's just a piece of plastic."

He's rationalizing, she thought.

"Sure..." Sasha agreed as he slowly lowered his face to her flesh toned dildo affixed to the belt on her waist. The eight inch realistic circumcised veiny cock she picked out specifically because it reminded her of his eight inch long circumcised, girthy and veiny cock.

He opened his mouth and placed his lips on the top of he cock. Gingerly, he slowly began to suck and fellate the cock head.

Sasha could feel somewhat the push back from his oral efforts. His cuffed hands rested under her thighs and thigh high stockings as he very slowly took more and more of the cock head into his mouth.

"This must be what you see when I blow you." She breathily remarked. She could feel the wetness and excitement build between her thighs at the erotic image of her feminized husband's full red lips wrapped around her strap on cock.

Each time he bobbed down onto her strap on, just like an inexperienced woman, he tried to take more cock inside his mouth. The wet slurping sound of saliva on silicon lewdly resounded throughout the master bedroom.

Sasha appreciated his efforts. The feminine image he presented as Barbara, trying hard to orally pleasure her faux cock was erotically charged and impressive. Although he couldn't take more than half of her strap-on length into his mouth as at that point it reached his...her...gag reflex.

Still, as minutes ticked by it was an impressive effort. One that Sasha, enamored by the image playing out in front of her was in no hurry to hurry along. The amazing image would be forever seared into her memory and one that she knew she would cherish for years to come. But sensing that his jaws and mouth were getting tired, she was also eager to move on to her ultimate goal for the evening.

Pounding his sweet ass with her strap-on cock!

Sasha took him by the face and helped lift him off her cock. She actually had to help him off her cock. Was he tired and unable to back off? Was that why she went on for so long? Whatever the reasons the fantasy only stoked her desire more. Especially as strings of drool sagged from his lips and mouth to the head of her strap on dildo, before string tension broke and the saliva fell free.

Sasha move from the head board and now took position behind Barbara's panty and pantyhose covered ass. The full firm globes of her athletic yet still feminine ass lay before her, ripe and plump, just ready and begging for her taking.

"Be gentle." His voice hitched in excitement. Sasha saw her looking over her shoulder at her. Her eye makeup conveying a look of lust.

Sasha could tell he was joking and putting on a brave face at the same time. Clearly he was nervous.

"I'll go slowly." She reassured him, as she the used the sharp edge of her fingernail, poked a hole in the sewn seam of the back seat of his pantyhose, and then aggressively and easily ripped the sheer 20 denier tights apart. She spread the tear widely giving her more than enough access to his thong covered ass and fully baring the globes of his ass to her viewing pleasure.

Sasha wasn't even surprised by how aggressive she was feeling towards Barbara as she knelt between his legs and then used her knees to shove his legs further apart, giving her the room between them she needed to assail his pert sexy bottom.

Sasha popped open the bottle of lube and squeezed out a dollop of lubrication onto her finger. Setting aside the lube she looped the strap of the thong buried between her husband's ass cheeks around the finger of her other hand and pulled back hard.

She probably gave his cock cage a wedgies feeling as she pulled back, exposing the star of his ass. Sasha slid her hand with the lubricated finger between the cleft of his ass and pushed her lubricated finger against his anal star.

She was rewarded for her efforts by a yip of surprise from Barbara as her finger pushed past her defenses and invaded her dark rear entry.

With gentle insistent pressure and even strokes she slowly massaged his sphincter to relax his rear entry. Feeling a slight decrease in pressure intensity on her finger she slipped in two fingers and continued to stroke and massage the anal ring. Within another minute the ring relaxed again and exerted hardly any pressure on her fingers.

Barbara let out a soft moan as she worked her magic, gaping his ass slowly in preparation for her dildo. Sasha could respect his nervousness. She worked slowly and took her time relaxing his sphincter, building up anticipation inside him.