Secret Sissy Stockings

It's hard to explain why Steven enjoyed it so much. Maybe it was the thrill of being in public. Maybe it was the thought of getting caught. Regardless, it certainly made passing the time at work more fun.

Steven was a nighttime stockroom employee for a 24-hour grocery store in his college town. It was an easy way to pick up money while still being a full-time student. And since he worked at night, he rarely had to interact with many customers. It was peaceful, but also quite boring. And it was that boredom that led Steven to spice up his work hours with some covert eroticism.

He started with small things. A pair of lacy underwear wouldn’t be noticed by customers and coworkers alike, but Steven certainly noticed with every step. The constant feel of the soft, satin panties gently caressing his genitals was enough to add some genuine excitement into his long work shifts.

However, it wasn’t long before Steven would start getting bored with just a pair of panties under his trousers. He wanted to step it up. Tonight, he would do just that.

Under his work clothes, Steven wore his favorite pair of black, nylon stockings, along with a new two-piece set of silky black lingerie he had purchased online. He was on cloud nine as he went about stocking the shelves, barely able to contain his erection that had begun to leak pre-cum. Nothing could stop Steven from indulging in his feminine fetish.

“Hi Stevie!”

The hairs on the back of Steven’s neck stood up. As he stood in the incontinence aisle, loading boxes of baby diapers onto the shelves, who else but Mrs. Roberts would come up behind him and whisper his name seductively into his ear.

Mrs. Roberts was a rich divorcee who was the absolute definition of a MILF. She was very curvy and stood head and shoulders above Steven, who was quite short for his age. One of her boobs must’ve weighed about as much as his head. Plus, she was incredibly young looking for someone whose kids were already out of the house.

Placing a hand softly on Steven’s shoulder, Mrs. Robert looked down at him with a sultry smile, “Silly me, I’ve forgotten where to find the flour. What aisle would that be in?”

Steven's erection was now at full swing. He gulped, not wanting to turn around to see her, which would only increase his blood flow. “A-aisle five, Mrs. Roberts.”

“Thank you, sweetie.” Mrs. Roberts gave Steven a pat on the butt, causing an aroused yelp to escape from his lips. Mrs. Roberts giggled at his reaction. “You’re always so much fun to tease, you know that.”

Steven tried to keep working, reaching over to the pallet of diapers to grab another box. In the process, he accidentally knocked one box off the top, causing both him and Mrs. Roberts to jump in surprise.

“I’m s-so sorry about that,” Steven stuttered as he rushed to pick up the box off the ground. Unfortunately, in his haste, the back of his shirt ended up getting caught on one of the shelves. It only took him a second to pull down his shirt, but the damage was done. Mrs. Roberts was given full view of the black lingerie he was wearing. He froze in place, nervous for what the middle-aged woman would do next.

The last thing Steven expected, however, was for Mrs. Roberts to reach her arms around Steven and begin rubbing her hands along his torso. “M-M-Mrs. Roberts?!” he yelled in a whispered volume.

“You’ve been a naughty little boy, haven’t you?” Mrs. Roberts cooed in Steven’s ear. Her hands methodically rubbed the young stock boy’s nipples, causing involuntary moans to squeak out from between his lips.

Steven was losing his mind. A combination of insane arousal and fear filled the brain. His head whipped back and forth, praying that no one would need to come to an incontinence aisle at 11pm.

It wasn’t long before Mrs. Roberts’ hands travelled south and began stroking his stocking-clad inner thighs. His hands shot up to cover his mouth, preventing his moaning from growing any more audible. His penis was stretching out his pants and panties to their limits. A minute more of this and Steven would have a definite clean up on aisle 3.

“P-please...s-top,” Steven muttered, hoping Mrs. Roberts would have mercy and not make him cream his jeans.

“Are you sure? Because…” At last, Mrs. Roberts’ hand found itself hovering directly above Steven’s swollen member. “...it doesn’t really seem like you want me to stop.”

Steven’s toes curled in his comfortable sneakers, pinching the bottoms of his smooth stockings between each piggie.

“Do you want me to stop?” Mrs. Roberts’ electric voice echoed in Steven’s ear. Of course he didn’t want her to stop, but he was at work. His brain felt like it was going to short circuit. He was so lost in pleasure that he couldn’t string a complete thought together. All he could do was feebly cry out, “N-no.”

That was all the permission that Mrs. Roberts needed. Her hands met the ridges of Steven’s shaft, and began to rub him within the confines of his silk panty paradise. It wasn’t even a full minute before Steven ejaculated the largest load of cum in his life. He gasped as he pumped squirt after squirt of the murky white cream all over his new lingerie, soaking through his pants and creating a massive wet spot.

Steven thought this would be the end, but Mrs. Roberts had other plans, as her hands continued milking his cock. The feeling of his wet, silky panties coating his dick in his own love nector was too much for the poor college boy. Soon, an even more powerful second climax occurred, flooding his pants with even more sticky jizz.

Finally, Mrs. Roberts removed her hands. Steven nearly collapsed to the floor. His legs were shaking profusely.

“Uh oh, looks like someone had a little accident.” Mrs. Roberts teased, which only caused Steven’s little buddy to twitch with excitement. “I don’t think you’re ready for a big boy job like this.”

Mrs. Roberts stepped down the aisle, reached up high on the shelf, and grabbed a box of incontinence underwear that looked like it would fit Steven perfectly. “I think it’s time you come home with mommy, don’t you agree?”

Steven’s mind was too far gone to say anything. All he could do was helplessly nod at the domineering woman.

Mrs. Roberts took Steven by the hand much like a parent would to a child and led him to the front of the store. She made sure to make a big deal out of buying him diapers so that all of his coworkers working at the registers would get to see what a big baby he was. “Looks like it’s gonna be back to diapers for my little boy until he can learn to control himself,” she stated with no regard to the sheer humiliation that Steven was feeling.

Steven didn’t even get to clock out as the two left the store, arriving at Mrs. Roberts’ minivan. She popped open the back hatch of the car. “Lay down here, sweetie. Let’s get you out of those icky clothes.”

Steven did as he was told, allowing Mrs. Roberts to slide off his slime covered pants and panties. She avoided dripping any cum onto his pretty stockings, which she made sure to run her hands across as she pulled a pair of incontinence briefs up his legs.

“There! No need to worry about accidents anymore,” Melissa said, patting the front of his slightly pointed diaper. His face got so red that he thought he would melt.

Melissa didn’t remove her hand from the front of his diaper, instead she held it over his penis and leaned into his ear, “Go ahead and prove to me that you're my baby. Mommy says wet your diaper.”

Steven couldn’t believe his ears. Just 20 minutes ago, he was working his job just like any other day. Now, he was laying in the back of Mrs. Roberts’ van, with her hand fondling his diaper-covered crotch.

Steven was in just blissfully horny state that he was powerless to refuse her. He closed his eyes and began to push. It took a few attempts of squeezing out small trickles before his body allowed him to flood his diaper in a steady stream.

Mrs. Roberts grinned devilishly as she felt the padding beneath her hand grow warm and wet. She leaned forward and kissed him passionately on the lips as he continued to urinate.

“I think we’re gonna have a lot of fun together, baby.”