First Date Second Test

Author's note:

Thank you for reading! I am new at this and appreciate you. Enjoy!

Adrian stood outside the coffee bar, his heart beating out of his chest and up into his throat, and checked his phone. It was 7:57 p.m. He wondered if he'd ever been this nervous before in his life. He couldn't recall. Anything, really. His mind was unfocused and overwhelmed. He pulled at the hair behind his ear, and tried to take a shakey big breath. "It's just a first date you dork."

This earned a strange stare from a woman he didn't notice who was walking around him and into the shop. It brought Adrian back down to Earth. It wasn't just another first date. Not at all. He'd had plenty of those and while they were always a bit nerve-wracking it was nonexistent compared to the pressure he was putting on himself now. They'd been speaking for weeks after he answered her ad. First over email and then on the phone. Tonight was the night their schedules had finally aligned and she had been quite clear in her expectations for it. But that was only part of the pressure.

Mostly it was Margot. He had never connected with someone so strongly and quickly before. Adrian was hopelessly crushing. He had never gotten the attention of a woman of this caliber before. His eagerness wrestling his nervousness. He checked his phone again. 7:59 p.m. Fear of being late overrode the anxiety and he steeled himself. Now or never. He stuffed his phone into his pocket and pulled open the door.

Despite its location geographically inside of a strip mall, inside of

The Sapienza

was all old-world warmth. Adrian had never been here before, never even to this side of town. His Uber ride had been long and it had given him plenty of time to overthink and overanalyze. It was no wonder he felt like a nervous wreck, but the low lighting here and din of conversation was bracing. He took strength from the crowd of people having normal nights and normal dates. If he was lucky maybe this would be the start of a new normal for him too but he didn't dare dwell on it. Dreaming too much made him nervous.

Margot wasn't hard to find, the espresso bar wasn't very big. Dressed just how she described, a houndstooth peacoat and red hairband, and sitting in a cozy part of the bar at a table for two, she had spotted Adrian as well. She was short and curvy, almost head shorter than Adrian, but the predatory look she was looking at him with made him feel like the small one. He maneuvered across the room and pulled the chair across from her out before introducing himself.

"Hey... ah, hello Margot. I'm Adrian, obviously... it's so good to finally meet." He stammered.

She just smiled and nodded for him to sit. Then, sitting in silence they just drank each other in. She had seen plenty of Adrian at this point but only sent had him a single picture, a professional headshot, in return. She kept locking eyes and it was flustering him, making him nervous like he was still standing outside in the cold. There was hunger in her eyes that would consume him then and there. He looked down instead, uncertain where he should be staring, willing himself to think of something to say. Much to Adrian's relief, she made the first move, reaching across the table and taking his hand.

"You look very nice tonight."

It made Adrian blush. He was wearing light grey slacks and a green polo. They were both a little too small, and he felt underdressed and young next to Margot. He didn't even know what she was wearing under the coat she had on. She continued, "You're bigger than I expected. Taller, broader, you look so sturdy. It makes me really happy."

Adrian tried to reply but there was no oxygen left in the room, ostensibly. He felt flustered, and knew he had start to blush. Margot smiled wickedly and squeezed his hands, like she was trying to pulse energy back into him.

"I should've had you stand next to your fridge for scale. It will make things even more interesting. Why don't you tell me about your day."

So Adrian did, it helped that it wasn't anything special. it suddenly relaxed him to talk about the mundane. His work, his lunch. He looked at Margot while he spoke, appreciating her heart-shaped face and green eyes. Eyes that had softened enough to start pulling him in head-over-heel. Had anyone ever looked at him like this? He couldn't recall, and felt like he was getting lost again. He asked about her day and her work. Just being physically present with her after building it up so much to himself was intense, he needed to keep his head above water and hoped just listening for a bit would help.

She talked about her day, Adrian watched her mouth. It did not help.

They sipped their coffee. She's ordered him a sweet cappuccino of some sort, it was a good distraction. Adrian was feeling good. He'd just started mulling what next generic ice-breaker to throw Margot's way when he looked and caught the return of the hunger in her eyes. it stopped him cold. Her voice had a harder edge when she spoke.

"Frankly, I'm finding this quite boring."

Adrian felt like he'd been punched right in the diaphragm. He almost felt himself physically reel. Boring? He certainly hadn't heard that on a date before. As far as dates went, this one had been off to a fine start.

"I-- what do you mean?"

"This feels like a waste of my time. Especially the chit-chat, the pleasantries, all this slow dance--"

"I'm sorry I'm just nervous and--"

"And I'd rather be fucking you."

"What?" Adrian felt like he had whiplash. He felt her foot push up against his groin under the table, pressing hard. That wicked smile again.

"Yes dear, I thought you remembered what I was interested in, I was quite clear in my intentions in using you up. Wasn't I?"

Adrian was blushing furiously. He was suddenly aware of both crowded room and forceful command in her voice. He had no idea what to say. Of course he remembered her intentions. They consumed his thoughts this week and almost every night for months. She squeezed his hand again, mercifully taking the lead.

"You passed the first test so well darling, so willingly. And I do want to fuck you quite badly. But there is the matter of the Second Test. You remember I told you about that?"

"Yes"

"And that I'd be testing you here, and now?"Grinding her foot now.

"Yes, Margot"

She smiled and bit her lip and pushed a small, shiny, pink bag across the table. She gave a last little push with foot and removed it. She was the one who looked a little nervous now. This time when she spoke her voice was soft,

"Take this to the bathroom and read the card."

Margot rose from the table and leaned over Adrian, biting his ear playfully. "Don't disappoint me." She whispered. Adrian gasped in reply and tried to catch his breath, and she sauntered back toward the front counter. Adrian watched her for a moment, then shot out of his seat with the pink bag and headed towards the bathrooms. He found it a strange comfort upon entering that the men's room was well-appointed and comfortable. He moved immediately to hide in one of the stalls and sat down on the toliet. He considered the bag for a moment. It looked like something from a perfume counter or lingerie store, but was surprisingly heavy. Adrian felt his pulse pound as he opened the card at the top of the bag and read:

Darling,

Time for your Second Test. If you are reading this it is because you passed the first test. I just know you did wonderfully. Now, take what is in the bag and put it on. Then start playing with yourself. I want you ALL worked up. Ten minutes at least, no cumming. Then come find me. Do not take off what I have given you. It is mine and you must return it to me. See you soon little pet.

-M

Adrian was breathing hard. Just getting instructions from Margot was enough to start engorging him. It strained against his slacks and he unzipped to release himself. He couldn't risk precum staining the front. He hadn't worn underwear. That had been up to her and she decided no boxer-briefs would be more fun.

Her first test had been easy and thrilling. Pictures for her. Of Adrian, of his wardrobe, of any sex toys or pornography he possessed. Then, a week later, more intimate photos. Poses he would never have dreamed someone would want to see him in. All shot himself at her command. When the time for the date came she picked his outfit. Exactly what he would and critically wouldn't be wearing. The slacks she had picked were too small, shrunk in the wash. His bulge was snugly outlined and light grey material wasn't interested in hiding any details. He'd been so happy to share himself like this with Margot and let her control him. It had hardly been a test.

This was more intense. With no boxer-briefs and ten minutes of playing with himself he would look plainly distressed when he left the stall. Not that anyone would notice, not with what was in the dainty, pink bag that he would be wearing. It was a collar. Heavy and black and made of two kinds of shiny leather. It had a heavy ring in the front of stainless steel. There would be no hiding it. No hiding what he was or how much it turned him on. He felt lightheaded. Could he do this?

The playing with himself part, getting all worked up, that had already begun. He'd started stroking himself the moment he had the collar out. He needed to stop and put it on. It felt important to follow her lead even if he logically knew she wouldn't know the difference. He placed the collar around his neck and gingerly tightened it. He didn't have a thick neck, but clearly Margot had thought he'd be smaller. The collar was tight. He got out his phone to time his pleasure out, and saw he had a text.

"Picture. NOW"

He fumbled and stood and turned and took a selfie. With a leather collar on and his cock hanging out the front of his slacks, he never looked more pathetically needy. It was the sort of picture that could haunt you in the wrong hands. He hit send. Margot reacted with a heart and another text.

"Oh my, best hurry up. Only five minutes of touching yourself. I don't want to waste anymore time."

Adrian unbuttoned his pants and let them fall to his knees and he sat back down in the stall. With one hand he worked his cock, shocked at how hard he was. His other hand went to the collar, pulling at it and feeling the pressure around his neck. The metal ring jingled as he jerked off. He realized it gave the act an unmistakeable rhythm anyone who came into the bathroom would hear. Instead he held the ring and pulled himself into a breathing exercise. It was important to have enough heat to keep the simmer going but he couldn't risk boiling over. Margot already knew what state this test would leave him in, if he went out having finished she would be able to tell. The thought made him shudder.

Mercifully no one else needed the men's room while the five minutes passed. He tried to find the least obscene way of containing his erection back in his slacks and ultimately gave up, stuffing it to the side and trying not to look at the prominent outline it had created. He adjusted the collar, wanting it nice and straightened. Margot appreciated attention to detail. Adrian steeled himself and walked back out into the coffee bar, head held high. He wanted to hurry to her side, being next to her made the collar make sense. People would understand.

But Margot plainly wasn't in the coffee bar anymore. Or maybe it was bad timing and now she was the one in the restroom. It wasn't a large enough room for a person to hide in. Under normal circumstances waiting a few moments to see if his beautiful date emerged would the polite thing to do, but these were not normal circumstances. There was a group of college girls who clocked him immediately and started giggling. Across the room a woman urgently trying to get her partner to look. More eyes on him as he scanned for Margot. The room felt sweltering now, Adrian needs some air and prayed he'd find he'd find her outside.

If the collar had been a little heavy in his hand it was doubly so around Adrian's neck, he felt every ounce as he moved back through the room. It made him want to hang his head. But he wasn't sure if that was the weight of the collar or the weight of the people staring. Outside the air was crisp and cold and made his nipples stand on end. His whole body was normally sensitive but even just the fuzzy trim on the collar was sending him into overdrive. He felt his cock throb in his pants. He still couldn't find Margot and was about to head back to look again when a car pulled up and rolled its window down.

"You're Addy right? Get in'"

It wasn't Margot. It was a man he'd never seen calling him a name no one called him. "You might have the wrong guy i think. I'm waiting for a friend." The man just sighed and tapped a sign in his dashboard.

"Hey my man. I was sent to get you and I don't want to embarrass you but the description given of what you'd be wearing was pretty... specific. It's for you. Get in man."

Adrian was blushing hard again. Was this the next part of his test? It had to be. He scrambled in through the side door and felt his core temperature drop a few degrees; he wasn't alone in the fan. This was some sort of carpool and the shocked expressions of the two women already in the minivan told Adrian they had clocked the collar the moment he got in the car. He sat quickly hoping to hide his erection, but he was only getting harder. He was very glad Margot had picked a spot so far from his part of town. He tried to wear his anonymity as an armor against their stares.

"You don't want to take that off? It looks tight."

Adrian was mortified and incredibly turned on at the same time. He didn't meet the woman's gaze but turned to nod negatively. The ring on the collar clinked. He didn't want to take it off at all. He wished the driver had music on. They were blonde and brunette and looked very professional and distinguished, like they had just left a dinner meeting. Now they were unwinding and that apparently included trying to embarrass Adrian as possible. The blonde kept asking questions. Was it heavy, was it hot, how long had he had it on. The brunette just giggled.

Mercy came in the form of a stop, another younger woman got on. She looked at Adrian and blushed, immediately feeling a sympathetic embarrassment. It had a chilling effect and the ladies in the back of the van quieted. A few minutes they pulled into a quiet-looking neighborhood, and they pulled up to a small ranch-style house. The driver let everyone know it was Addy's stop. The brunette laughed and told him to not forget his leash next time. Adrian just got out of the van as quickly as he could, so thankful he'd been the first drop-off.

~~~

The house was quiet, with one light on above the front door. Adrian panicked a little realizing he had no clue where he was currently. Margot wanted him out of his comfort zone, wanted to push him. He gulped and walked towards the door of the house. Before he rang the bell he was glad the houses in this neighborhood had such large yards, it reduced the chance the rideshare dropped him somewhere else. He didn't have to ring the bell because the door swung open to reveal Margot's silhouette. It was such a relief to see her. Adrian wanted to push her up against the wall and kiss her with everything he had. He wanted to fall at her feet and cry. Instead he just numbly moved into her entryway as she stood aside.

"I'm so glad you made it, was a it nice ride?" She said in a teasing voice. Adrian thanked her profusely for having him over and looked around. It was a cute home, well decorated and full of character. He was so lucky to be with someone with such good taste. He saw her pea coat hanging from a coat rack over a bin of varied collars. If you didn't know better you'd think Margot owned a few dogs. She noticed him staring.

"Different collars for different moods, pet. The one you have on now is the most controlling, I use it when I really want someone to feel owned. How does it make you feel Darling?"

Adrian nodded, "Owned, aroused, nervous--"

Adrian doubled over in pain. Margot had just struck him in the balls with her backhand and he went to his knees. Mostly out of shock.

"Proud, you should be proud I let a slut like you wear my collar for even an instant"

"I'm sorry, Margot I'm so proud and lucky"

She grabbed his hair and wrenched his head back. "You'll call me Goddess from now on, is that clear?"

"Very clear, Goddess."

"When talking with others and in public, refer to me as your owner."

"Yes, Goddess."

"Perfect. Now strip, come into the living room and kneel."

So, Adrian immediately worked quickly to undress while Margot left the entryway. He'd never stripped faster. He made a hasty pile of his garments and then took the extra time to fold them, he didn't want him or his things to be out of place in her world. He got goosebumps all over, his ass felt cold. Being naked in the entryway of a home felt extra naked, and Adrian contemplated how he should walk into the room. He wanted to appear eager and excited but he was also working through some shame and embarrassment too. He decided he wouldn't cover up as he walked out, the state of his cock communicated his excitement better than any body language could.

The living room of Margot's home was cozy and warm. It had a sitting area and dining table against a half-wall that opened into the kitchen. The furniture in the sitting area had been pushed to the side except for a love seat and ottoman Margot was currently occupying, legs crossed. His eyes were drawn to hers, and then looked with her at the coffee table, full of fun and frightening things. Adrian gulped. The time for backing out had been before he walked into the room naked. In the center of the room was a soft throw blanket that had been folded in quarters. He kneeled on it and looked up at his owner with pleading eyes.

It was the first time he'd taken a moment to appreciate Margot's outfit: a Lacey red and black corset, with a silky mid-length black skirt. He could see the hint of tattoos on her legs and shoulders he never would've dreamed she had behind her cute bob and peacoat cat's eye glasses. She uncrossed her legs and leaned forward in a positively predatory manner and Adrian felt his cock start to leak precum. The view of her breasts was overwhelming, but it was the objects she was holding that drew his attention now: a long, stiff leather-tipped riding crop and a not-very-long leather leash. His cock was twitching reflexively as he thought about what was in store for him. "It's time for fun, pet. I'm going to have my way with you. I finally get my hands on you and I'm not going to hold back I promise. You're going to cum so much" she said in a sing-song voice. Her eyes were telling a different, darker story.

She stood now, and left the riding crop on the edge of the ottoman. Taking the leash in one hand she pulled Adrian into a deep kiss, putting her thumb on his chin. He took the cue and opened his mouth, Margot forced her tongue deep into it and left him gasping for air. The kiss ended with a metal clink of the leash being attached to his collar. He felt the slack fall against his body as Margot nibbled on his bottom lip. Leash in hand, she strolled around to his backside and pulled until Adrian started to lose his balance. After putting his hands out to stabilize himself he found himself bent back, cock sticking wantonly into the air.

From behind him, he heard her start to speak as she walked over to the coffee table. "You know pet, I'm not even sure if I should tell you this, but your cock looks truly ideal. I needed to see it to be sure." She said in the same voice she ordered coffee in. Adrian hear the crack of a bottle opening and smelled a sweet oil in the air. She appear at his side and kneeled, before firmly gripping his shaft in her hands. "Adequate length, but such phenomenal thickness." she punctuated syllables with hard squeezes of his cock and it was driving Adrian wild and unable to contain his little breathy moans. "But what really takes it over the top to me is the sensitivity."