Thrift Store Sissy


A story by wendi marie st.clair

She was looking at girl’s blouses the first time He saw her. Of course, most of the world wouldn’t have seen her as a “she” at the moment, but wearing her flare-leg, hip-hugging jeans that were obviously from the junior miss department and the androgynous purple t-shirt that showed that she shaved her body, she looked like a “she” to Him. Everyone else would have seen a twink; a very flamboyant, faggy, gay guy, but He knew better.

He knew because He could see that He was there at the thrift store to do the exact same thing. She was shopping for girly clothes, and so was He. He felt that he was about smack in the middle of the touted “gender continuum,” but He could see that she was way towards the female end of the spectrum in spite of the body Providence gave her.

He casually watched her looking and picking through the racks as He did the same. He kept drawing nearer and nearer to her and sensed her discomfort because of it. He was sure she just wanted to be left alone as she shopped, feeling like a freak as the rest of the vanilla world flowed around her. He was sure He was about to chase her away as He approached. His mind was spinning with a way to break the huge layer of awkward and slippery ice. He knew He had to do something now before she made a subtle bolt to the exit.

“Hi, sweetheart,” He blurted, feeling like an idiot. He thought that if His shadowing her had been off-putting, then coming right up to her with a pathetic line like some mook would surely run her off forever.

She met him with a stricken, deer-in-the-headlights look in her green eyes, but there was a glimmer of hope that maybe she had been approached by someone who understood and accepted her at least in part.

“Hello,” she said, with her lips turning up into a thin, self-conscious smile.

He smiled and showed her a couple of skirts draped over His arm and said, “Looks like we shop for the same types of things here!”

The look in the girls eyes was just like a sunrise. “Yes, i think we do!” she said.

After that, it would not do but that they would shop together – not only there, but at a couple of other stores until He talked her into going to a local pub that had an accepting staff and clientele. They ordered their drinks and sat down for a little small talk at a table off of the small dance floor. She had been checking Him out all day. He was handsome as a Man, and she thought He would also cut an excellent figure when draped in elegant lines and silky material.

He also enjoyed being with her all day. He found her very attractive and had an intuitive intelligence that he enjoyed. It became well established in His mind through the course of the afternoon that she was naturally submissive and demure, always respectful when making a suggestion as to colors that suited Him or the fit of a certain garment. He found that He wanted to woo and possess her; to make her His own.

She told Him that she was in town for business and was working during the day, but was staying overnight to just enjoy her femme self. After more small talk, they decided that they might go back to the room she had to try on what they scored in the shops around the city.

When they arrived, she begged leave to go to the bathroom to freshen up and put on her makeup. She turned on the television for Him and got Him a drink out of the little fridge. After making sure He was comfortable, she turned to the back of the room, giving him a coquettish smile.

As she made sure she was all prepared for whatever may happen, she was giddy in thought about the soul in the room with her. She could feel the presence of both His femme and masculine sides. It did a wonderful job of bringing warmth to a smoothly Dominant personality. She wondered what would happen sex hikayeleri and found herself berating herself as a trollop speculating on what He might do – and what she would let Him do.

He was able to watch her across the room as she concentrated on the mirror, applying base, then contouring and eye makeup. Her actions were so naturally feminine, He wondered why anyone would think of her as anything but a woman. He had forgotten the TV as he slowly made His way to the corner of the bed and just watched her.

“You know, sissy, there is no way in the world that I could ever see you as a man.” He said.

It caught her short, and she stopped applying the mascara to just look at Him, her eyes seeming bigger because of the eyeliner.

“No one has ever called me that before without making it a vile insult.” She said, “I can tell that You didn’t mean it as an insult. You called me that because it is what i am.”

“Yes,” He said. “Why can you not say it, sissy?”

“Say what?”

“Sissy; I called you sissy, but you didn’t say the word at all. I want you to say it.”

“Why? “She asked.

“Because you need to; you need to acknowledge this to someone out loud. Say it. What are you, sweetheart?”

“A…sissy,” she said, diffidently.

“You are a what?”

“A sissy.” She said, again, but still sounded tentative.

“There is nothing wrong with you.” he told her. “This is a part of who you are. I haven’t treated you like a man all day. It doesn’t mean I don’t respect you, I just have a different kind of respect. To me, a sissy is one of the most beautiful things on the earth, and you are beautiful for a sissy. So, tell me now, with confidence. What are you?”

“A sissy,” she said, grinning shyly.

“Better, sweetheart, now let me watch you finish making yourself pretty for me.”

When she was done, she was a vision of sex in little black patent leather heels, thigh high stockings held up by garters that hung from the black corset. A little black lace pair of panties covered a small “boi clitty.” Her face was pretty with ruby red lipstick matching the lacquered toenails that peeked out of the peep-toe heels. Topping it all off was a pretty mane of brown hair in a wig that matched her natural hair color.

He was very aroused at the sight and wanted to kiss her. He approached to do just that when she laid her hand daintily on His chest and said, “Your turn!”

It was now His turn to be a bit taken aback. He had not actually given that much thought into slipping into his femme side this evening, but he had plenty of brand new things to wear and had brought a little bit of lingerie to wear underneath it.

“Come on,” she cajoled, “Let Her out tonight! I dressed for You, and I love it…because I am a sissy. I know you are not. You are – I don’t know – something else, but You can express Yourself here. Let me make You up and bring out the Woman inside You.”

He knew He was about to do this; to actually get dressed en-femme in front of somebody who accepted Him as a Dom/Domme whether she actually knew it or not. His clothing wasn’t going to affect how this sissy saw Him.

He went into the bathroom and slipped on a pretty lace racerback bra in black and some matching panties. She passed him some clothes through the door as outerwear. It was a black sheath dress that somehow managed to make him seem both pretty and strong with the cap sleeves and the found neckline. The skirt of the dress had a bit of a swing to it. He stepped out of the bathroom to sit in a chair she had pulled out for him so she could do Her face. The base wasn’t quite right, she said, but she added that they could shop for her some makeup sometime. She concentrated as she did eye makeup and contouring. The Domme noticed how the sissy’s movements porno hikayeleri were naturally dainty and super feminine as she deftly applied makeup.

She had thought She was aroused looking at the sissy before, but it was nothing compared to standing before her in a dress and lingerie. The sissy was standing there with her hands arranged in a fig leaf, her eyes downcast. She had fully dressed the Domme while the sissy had remained in lingerie. She wondered if the sissy even noticed she did that, naturally submissive as she was.

The Domme looked in the mirror. “Very good job, sweetheart, but you are right that the base was not quite right. I know it’s not your fault, but I’m afraid I will have to punish you anyway.”

The sissy looked up again with that deer-in-the-headlights look again.

“What did you think would happen when you brought me here, sissy?” the Domme said, not unkindly.

The sissy cast her eyes back downward in submissive acceptance.

The Domme make her elegant way over to the foot of the bed and beckoned to the sissy. “Come here, little one, over my knees,” she ordered.

The sissy didn’t meet her Dommes eyes as she sashayed her way over to the elegant Woman. She arranged her body to drape across the legs of the Domme and waited in breathless anticipation.


t started with caresses. Dominant hands stroking and exploring smooth, nylon covered legs and lace covered derriere. The Dominant made an approving noise when she found that the little knickers had a slit in them that exposed the sissy’s delicate opening. The stroking and caressed continued. It lasted longer than the sissy had thought it would. It turned into an agony of anticipation as she wondered in her mind: would She be rough and cruel? Would it hurt? Would She make her cry? Did she want Her to?

The smack of hand against soft, smooth flesh was unbelievably loud in the quiet room. The sissy’s whole body jolted more in surprise than pain. So began a litany of tush-reddening blows from the bare hand of her Domme. The Domme built the intensity up slowly until the sissy was whimpering through clenched teeth. Again and again the tireless hand found the receptive buns until the Domme stopped abruptly, nudging the sissy off.

“On your knees, sweetheart,” the Domme ordered, raising the skirt of the dress, “You know how to thank me for your spanking, honey.”

The sissy did , indeed know how to thank her Domme. She was panting with a new anticipation as the sissy reached with trambling fingers to the now distended front of the panties. The Domme’s shaft sprung into her face as she moved the barrier keeping the majestic flesh from her ruby lips. The sissy looked up into Dominant eyes as she opened up her warm, receptive mouth, engulfing the phallus, all the way down to the massive balls – on her knees…in her proper place.

The sissy’s eyes closed in pleasure as the Domme placed Her hand at the back of the sissy’s head. The Domme was so aroused that she had to be careful not to cum too quickly, so She would have to force the sissy to give a very deep and very slow blowjob.

The sissy was totally at peace. The smooth hardness that filled her mouth and throat made her feel somehow full and complete; like she was finally fulfilling her purpose and occupying her rightful place. Presently, she felt the Domme’s hands move her and urge her to move and work her mouth slowly. She could feel that her lipstick was smearing on the tasty phallus as she undertook her ministrations, being fed the imposing body of a Dominant Woman.

The Dominant saw a little bottle of lube in the sissy’s handbag and brought it out, noting that there was a sizeable butt plug beside it. The sissy heard the unmistakeable click of the tube of smooth lubricant as she served seks hikayeleri there on her knees. She felt the Domme bend and using her strong fingers to apply some of the lube to her sweet little pucker nestled between here smooth globes. The sissy continued her slow, deep sucking, as she had not been told to stop. Serving this elegant woman simply felt too wonderful to stop.

Soon, the Domme gently withdrew her phallus and ordered the sissy onto the bed on her hands and knees. It was finally time, the sissy thought as she tried to present herself as sexily as possible, arching her back and putting her little tushy up like a cat.

There was warmth at the opening of her puckered portal. She concentrated on relaxing and submitting to the Dominant rod pushing slowly into her. She whimpered and moaned as she stretched around the invading tool.

The Domme watched the perfect circle of the sissy’s anus goggle down Her shaft time after time as She worked it slowly in and out of her in an unhurried way. She had already triumphed and was claiming her prize now. There was no need of great haste. The whimpering submissive had laid her face down on the matress and was sucking her thumb in an adorable jesture as she was being smoothly sodomised. Her long lashes winked elegantly like butterfly wings as she winced with the invasive motion of the shaft. The Domme had a knowing look upon Her face. The sissy was Hers, body and soul. Even if she went off of her little rocker and decided to try to act like a man again, this Domme could look into her eyes, and both would know that the Domme could describe the feel of her tonsils on the head of Her shaft, and the warmth of her accommodating bowels. Soon, Her potent seed would be swimming around inside the precious sissy. This was permanent in a very

real way.

The Domme pulled out and rearranged her sissy on her back. She placed the sissy’s heeled and stockinged ankles on Her shoulders and plunged the phallus back into the sissy’s receptive and tight orifice. Once the head breached the ring, it seemed like her canal actually sucked the Domme inside, hugging the shaft with gratitude as she began a faster piston like movement, slapping her front against the delicate cheeks and thighs of the submissive. The sissy writhed and moaned whimpering sweet nothing and encouragement as the Domme took Her pleasure. This charge of seed had been welling within for far too long and put immense pressure on her super hard phallus as She was slamming into the poor sissy’s yielding flesh.

Their eyes locked as the sissy whimpered and the Domme roared, it seemed like gallons of virile semen pumped into warm, tight heaven as the sissy took the seed of her Domme deep into her smooth body.

“Oh, right in your pretty sissy ASS!” the Domme said between teeth clenched in exquisite pleasure and triumph.

“Yes!” the sissy replied, happy in her own way to accept the life giving fluid from her Domme.

They lay locked together like that for a long time as the both re-learned how to breathe, their hearts beating a rhythm they could both feel at the point of their joining.

Eventually, the Domme had her sissy get back into the position, with her face on the matress, propped up on her knees, sissy ass high in the air. She slipped the butt plug from the sissy’s handbag into her delicate, receptive ass, watching as the tight hole swallowed the bulb and tightened against the neck, pulling it deep inside.

“Honey,” said the Domme, “I want this to stay in all night. I want me swimming around in you trying to breed your sissy body for as long as my seed can.”

“Yes, Ma’am,” the sissy replied with a smile.

After washing Her face and replacing Her dress and lingerie with Her Man clothes, the Dom gave the sissy a kiss. He tucked the sissy in and sat on the side of the bed, caressing her smooth body and talking for a while before He had to leave.

“Sweet dreams, little one,” the Dom said, “you will be in My care next time.”

“Yes, sir,” the sleepy, becalmed sissy replied.

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