The Sissy in the Loft

*All characters are 18+

***

James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look from behind the counter on the right side of the room, the kind of look he would expect from her given the circumstance. On the left wall was a collection of lingeries, kink outfits, plus some harness and straps for more adventurous topics. On the back wall was many tools for the similar topics, whips, harnesses, gags, etc. On the back left corner was the collection of sex objects like veiny dildos in a range of sizes, plugs, vibrators, etc.

James nearly held his breath and barred his mind in order to keep walking forward down the left wall, refusing to look at the shopkeeper. Out of the corner of his eye, she was a black woman airing on the slightly larger side. Her hair was up in a long black ponytail, and she appeared to be wearing little makeup save for some bright red lipstick. James walked into the corner and looked over in awe at the store's collection of toys. His mind raced with his options, but he had known it would, which is why he had come with a very strict list of what he was getting. He saw the pink, 6", suction cup dildo wrapped in its frilly packaging. He grabbed it and tucked it under an arm. Then, he grabbed the black realistic 9" dildo. Lastly he grabbed a medium prostate massager butt plug.

He hesitated for a second, knowing the shopkeeper was looking at him, he worried that he looked too prepared with what he was getting. He knew he was giving away that he had put some thought into this, and had been a man on a mission. But he just sighed, turned and faced the shopkeeper. Her expression had changed, from surprise and suspicion to a strangely cocky and amused grin. He walked up to the counter and set the items down. She began to scan them and asked without looking at him, "Want these in a bag honey?"

James squeaked, "Yes please..."

She went on to start putting the in a bag. James was fighting back sweat as he finally asked her the question he had been waiting to ask, "When does the sex arcade open, and when does it close?"

She looked back up at him with that same grin but wider this time, "Oh. It, uh, starts after we technically close at 9 and goes until 12:30. It's $30 to get in."

"Okay, thank you..." James said as he paid for the toys and grabbed the bag.

James hurried out of the shop and practically ran back to his car. He hopped in and drove the 45 minute drive back to his house. It was an annoyingly long drive, but that's just how things are living in a small town a ways out from the denser cities. He had told himself once that he would never make that drive for this reason, then again he had also told himself he would grow out of this fetish. When he got home, he walked inside then immediately opened the door to the garage. He turned the light on and began to climb the wooden stairs up to the loft, his room. He walked to his door and stepped inside the slightly colder realm of his room.

He flicked the lights on and turned to throw the bag onto his bed. It landed next to a few other items of notice: A collection of female clothes ranging in sluttiness, a bag of makeup, and a bag containing his just arrived red bob-cut wig. James looked in the mirror to begin thinking about his look all together, he was a skinny average height white boy with short blonde hair, blue eyes, soft facial features, a thin feeble frame, a strangely skinny waist, and a surprisingly plump rear end with fit legs. He twisted his body to squeeze and examine his butt, admiring the results of his squats and other workouts. In his boy clothes he could never really see these results. But once he gets ready, and he lets Jasmine out, then it's a whole different story.

James lived with his parents in his small house in his small home town. He was attending the local community college and was planning to transfer after that year. He was coming on twenty-one soon, but really didn't resemble that age. He either looked like a well developed 13 year old boy, or a sleek, under dressed, tomboyish female 18-year old girl. He had begun dressing up as a girl three years ago out of sexual desperation. In high school he hadn't ever had sex, nor had he even kissed a girl, which lead him to extreme lust and eventually extreme apathy to how he could sate this sexual hunger. It began as all fetishes do, starting with regular porn and watching it so frequently that it grows tiresome. Out of curiosity he began to explore more interesting genres, more adventurous avenues of fetish, and soon he found himself looking at photos of boys strangely similar to him dressed like girls with chastity cages and dildos. He had found sissies.

Originally these pictures and the genre was disgusting. He didn't like men and was completely straight. But out of pure shock and disgusting curiosity he kept returning to them. Slowly he began to grow an appreciation. In his mind at first, he began to feel attracted to the idea emasculated men, so weak that their manhood could be stripped of them by real men. Turned into feminine fuck-sluts. Of course, originally he also saw himself as the strong man able to emasculate the sissy boy. But soon he began to crave trying out dressing as a girl, maybe even sucking another man's cock. And before he could even realize it, his mind had shifted to being the emasculated sissy craving cock.

His sister was two years older than him and wildly more successful. She was living with her boyfriend, who showered her in clothes and gifts. For that reason, she still had a full wardrobe of her old clothes stored in her old room in their parents house. On top of that, the bathroom they used to share still stored tons of her old makeup and jewelry. James began his dive into sissy-life by picking panties from his sisters storage. Soon dresses, skirts, stockings, and shoes. Then he began diving into learning how to do his makeup. He began shaving every inch of his body and following specific workout routines he saw online to form his body to be more feminine. The final step in his transformation was downloading kik and beginning to advertise himself on message boards like 4chan. Soon, he was dressing up completely and indulging in full photo shoots for strangers online who would degrade and drool over him. It made him feel amazing inside, finally the nail in the coffin to make him addicted.

After months and months of this, his mind was mush while he was alone in his room. Completely hooked on his sissy fetish, unable to think about anything else than when and how he was next going to dress up and message his "Daddies" on kik. It was one of those men that actually gave him the name Jasmine. He even began to refer to himself as such, identifying as a 'she' wherever possible. Of course, his parents were none the wiser. This was still James' secret, and he couldn't stand to see the disappointment on their faces if he ever told them. And so it stayed that way, ever torturing him more to know Jasmine was confined to his room. Never to go out and truly experience what she craved. That is until this weekend.

His parents didn't often travel, but finally they told him that they were going to go visit his aunt in Texas. They told him he would be in charge of looking after the house for five days starting Saturday. He managed to keep his cool and assure them that he could handle it. Then the second he got back up to his room he began his plot. He finally ordered the red wig he had been wanting and set it to arrive the day they left, then began collecting everything he would need. Finally they left, the wig arrived, he went to the shop he had heard about 45 mins away, and there he was. He had been waiting for this moment for so long, and finally it was here.

He started with the usual, a shower, a shave, and lotion. He showered with frilly feminine smelling soaps, shaved every inch possible, and used a lavender scented lotion. Then he started dressing himself. He pulled a pink lace thong up his smooth legs to cover his small 3" penis. Then he put on a matching bra and stuffed it with a few pads to resemble small A-cup breasts. He rolled his white stockings up to connect to his white garter belt. He looked over his dresses and chose a tight black dress with long sleeves that clung to his body all the way down until it flayed out at his waist and covered just past his butt. Now that he was that far, he went back to do his makeup. He applied every trick he had learned to make him look like a hot slut. He brought a bit of red to his cheeks, added thin cat-eyes, long black mascara, a bit of gold above his eyes, and some fire-truck red lipstick to finish it off. He put the hair net on to hide his short blonde hair, then slipped the red wig over his head. And suddenly, looking in the mirror Jasmine had arrived and was looking as hot as ever.

She began putting the finishing touches on, like painting her nails red, slipping some black 5" heels on, and even clipping on some old earrings her sister had once worn before she had actual piercings. But she did have one thing she couldn't forget, she lubed up her butt plug, moved aside her clothes, and pressed it into her boi pussy. She pulled out her phone and took some sexy photos of herself, sending them to her daddies along with telling them that she was finally going to commit and suck some dick. She then grabbed a small purse from her sisters room and threw everything she needed into it, phone, wallet, keys, lube, condoms, and her dildos.

She finally got in her car and began driving back down. She felt butterflies sting her insides every time a pair of headlights passed her, knowing they could see her and wondering if they could tell she was a boy. The drive went by in a flash as she found herself pulling back into a parking spot by the shop. Everything was calm, and there were only a few people she could notice out on the street. She could feel her face burning red with anxiety and fear, but she took a few deep breaths and stepped out of the car. She then walked up to the door and opened it, again hearing the bell ring from above her.

The same black woman was sitting behind the desk. Jasmine began walking up to her, and at first it seemed as though the woman didn't recognize her. Once it clicked, her face lit up with shock, then once again a Cheshire grin. No one said anything while Jasmine pulled out her wallet and placed the $30 on the counter. The woman looked at it, then at Jasmine, then began to put the money into the register.

"So, I'm impressed. You make for a really cute girly boi." The woman than abruptly said.

"... Thanks... Is it obvious?" Jasmine said coyly as her cheeks flared red again.

"Oh don't worry honey, you're a real cutie. It's a little obvious from my point of view cause I've met a lot like you so I know what to look for. But really, you're easily one of the most convincing I've met."

Jasmine was a little shocked, "Really? There's a lot of people like me?"

"Hmm. Well, 'a lot' is a relative term. But yes, honey, you're definitely not the first girly boi that's walked in here wanting to suck some dick like a real girl."

"Oh..."

The woman pulled a pen then wrote something on a paper that jasmine couldn't see. She hummed for a second then looked back up and asked, "So, what exactly are you looking for here on this fine evening? Just the glory holes or full access?"

Jasmine realized that she hadn't really thought about it. She desperately wanted all of the above, but didn't now whether she should take it slow, "Um... I don't really know."

"I assume it's your first time as I haven't seen you before." The woman said.

Jasmine only nodded.

"Right. Well, given the toys you bought earlier I assume you know your way around a cock. Right?"

Jasmine nodded again.

"Okay then, honey. Here's what I'm going to do. I've already had a couple men come in tonight wonderin' if anyone was in the stalls to which I had to tell them no. It's been a slow night. I can tell you're a dirty slut, so I'm going to sign you up for a full stall. They can either use one of the two gloryholes to either wall beside you, or come right in and work with you directly. Sound good?"

Jasmines heart jumped into her throat as she nodded once more.

"Good. Now go down that hall all the way to the end door. It shouldn't be a long wait." She said pointing to a small door in the right corner of the room.

Jasmine walked over and opened the door to see a small hallway. There was a split in the hall with a sign that read, "Girls to the right, men to the left."

Jasmine followed the hall on the right and went down to the furthest door. She opened it, and entered. Inside she could see it was exactly as she expected. There was bench with a blanket and pillows along one edge, a door opposite the one she had entered, and a gloryhole on both walls to her left and right. She set her purse down and began inspecting the whole room to also spot a camera in the top corner. She figured it was for security so no one could come in and hurt her, but she also loved the idea of someone watching as she serviced real men.

Jasmine Sat down on the bench and pulled out her phone. She began messaging some of her daddies online, sending them photos of the room and herself as evidence that she was going through with it. She began to get wrapped up in her conversations as she waited. About ten minutes went by before she finally heard something. It sounded like the door opening and closing down the hall followed by footsteps along the men's side. She froze up. Her heart began to beat harder as she felt the color drain from her skin.

The man entered the stall next to her. She could tell not only from the sound of that stall opening and closing, but there was enough light and room through the gloryhole for her to see his blue jeans through. She slowly set the phone down on the bench and stood up, knowing what was about to happen but not knowing if she was ready. She took a step towards the gloryhole, and waited a moment. Sure enough, the man unzipped his pants and stuck his white dick through the hole. She was slightly shocked to see it. Maybe the fact that it was clean, girthy, and about six and a half inches long, which seemed pretty sizeable and admirable to her, or just from the fact that any of this was happening in the first place.

She stared at it for a another few seconds before she slowly got down on her knees in front of it. She felt the cold wood under her knees through her stockings. She was staring straight into the head of the stranger's cock. She was even close enough to smell it, and boy did it smell. She knew the smell from her own, slightly musky and filled and anticipating of sweet relief. When she had smelled that from her own tiny dicklette she had always been a little disgusted, always making sure to wash, scrub, and perfume it so much so that she would never smell It again. But when it was coming from another man, a real man, something about the stench was hypnotic. It filled her nostrils and began to cloud her mind. The cock was only semi-erect, but it still seemed to pulse very slightly with the beat of the stranger's heart. She noticed it, and the only thing she could think about was wanting to feel this man's heartbeat. She reached out, and lightly grabbed the shaft of the mans cock. It was warm in her hands, mostly firm but quickly growing harder as it grew to full attention in her grip. She could now feel the slight pulsating in her hand, and something finally snapped in her brain. She lost whatever string of sanity she had left from being able to feel a strangers heartbeat by holding his cock. She lost all semblance of her manhood, and all she wanted now was to be a good girl.

She leaned in and began to lick the head of the mans cock. It tasted like it smelled, which might have disgusted her by description alone but again all it did was excite her more. She could feel her own dicklette pressing against her panties at the thought. She licked it some more before closing her lips around it. She reminded herself of all the tricks and lessons she had learned practicing on her dildos and from talking to her daddies. She held back her jaw, placed her tongue under the shaft, and relaxed her throat. And suddenly, before she knew it, she kicked into auto pilot and began bobbing up and down on the strangers cock. It was just long enough to begin pressing against the back of her throat. Luckily for her, she had already practiced enough to no longer have much of a gag reflex. And so she worked.

She felt a tiny bit of precum dribble onto her tongue. The taste was manly and addicting. She wanted more and knew she could get more. She began picking up the pace, occasionally pulling off to kiss and lick the cock like a lollipop. She knew the man was enjoying it because he was moaning and grunting from behind the wall. She began to feel his cock pulsing harder and more precum dribbling. She quickly reached for her phone, flicked on the camera, and began recording as she milked the man's cock. He grunted one last time and seemed to press against the wall as he began to cum in the back of her mouth. She loved the feeling and the taste, but the showgirl in her wanted something nice to send to her daddies and pulled back, opening her mouth to catch the last few strands of cum like a fountain.

The man retracted his cock and began to zip back up while she ended the video. She still had most of the man's seed her in mouth, but she didn't want to swallow it yet. She let it sit on her tongue, tasting it, admiring it. Her mind felt numb in the sexiest way and her body was warm. She had finally done it, and that man's cum in her mouth was her reward. She cherished it before finally swallowing it down like the good slut she was.

She heard the man finish up and leave the stall. He left down the hallway and she heard the door close behind him. She sent the video to her daddies and asked of their opinions. All of the supported her endeavors and demanded that she stay for more. She got back up and sat on the bench once more, expecting another long wait. However, only a few minutes went by before she heard the door open again. Another man walked down the hall, entered the same stall, and repeated the same process. She did too.

Jasmine got down on her knees, waited for the cock, then began to service it. She took photos, and a video as the second man came in her mouth. This man even muttered, "Damn fine head, slut." Before leaving.

She was giddy with excitement knowing she had serviced two men already and hadn't even been there an hour. Unfortunately for her, it was a good twenty minute wait for another companion to join her. When she heard him come into the hallway she jumped at the occasion and dropped to her knees before the hole. But something was different this time. She heard the man walk past the door and up to hers. Her heart once again began to beat as the man opened her door and saw her there kneeling before the gloryhole.

"Ah, eager I see. That's good 'cause so am I." the man said in a gruff voice.

He was a tall, well-built man at about 6'2" with very tan skin. He seemed gruff and like he hadn't shaven in a while. He seemed to Jasmine like some kind of construction worker type. But she was less concerned with his job, and more interested in knowing what he was packing. He stepped into the stall and let the door close behind him. Jasmine shifted around on her knees and looked up at the man with begging eyes.

"So the lady in the front said you were a special kind of 'gal." He said unzipping his pants and freeing his behemoth of a cock, "Says you ain't even really a girl."