Full Day of Firsts - 01

Nick had told himself he was done with his "exciting but temporary kink interest" nearly a year ago, yet the locked suitcase with his "hobby supplies" was still tucked away in the back corner of his closet, and his thoughts went to it instantly on a Saturday morning when his text alert chimed and a familiar message appeared: "I'm in town, time for your services."

At first, ignoring the summons seemed like the best bet. He managed to do so for about five minutes before old habits and the pull of an old compulsion took hold and he realized that simply not answering wasn't acceptable. Even with the contact info deleted he knew from the content of the message that the unfamiliar number was Mr. Chase, and it wasn't appropriate to ignore Mr. Chase. Even if he was going to turn him down.

"I'm sorry, I don't do that anymore," Nick responded.

The reply was immediate: "Bullshit. Here's my location, get over here." An address followed.

"Really," Nick typed, "I haven't done it since the last time you were here."

"Good, that earns you some special rewards. I've got a day of firsts planned for you."

Nick simultaneously felt a sinking in his stomach and a stirring sensation a bit lower. He pushed the latter aside and wrote, "I'm just not into that anymore."

There was a pause, then, "Do you still have that suitcase?"

Nick froze, not wanting to answer. After a minute of silence the text alert chimed again and he read, "That's what I thought. Put it in the car, get over here, and park next to the semis. Then text me when you're ready."

Ten minutes later, he was in the car.

Twenty minutes after that he pulled into the parking lot of an extended stay business hotel. He saw the semis right away, parked in the corner of the lot.

Pulling in next to them, he debated once more just turning the car around, as he had virtually once per mile on the way over, but the commanding tone of the last text and the feel of the suitcase had completely awoken the old compulsion. Instead of leaving, he climbed into the backseat of his car, opened the suitcase, and very efficiently changed clothes.

In minutes he'd completely transformed. Instead of his masculine weekend sweats and t-shirt, he now wore high heels, fishnet stockings, a g-string that would be almost visible when standing because the skirt over it was so short, a halter top, and a feminine wig. He also put on a lace eye mask; it helped make a feminine touch since he didn't know how to do makeup. Of course, Mr. Chase would very likely have him put a blindfold on over that, once he texted the real location for their encounter. Nick figured his domineering playmate had just told him to pull over and change here so that he'd have to drive to some secluded area across town, nervous the whole time that he'd be seen or even pulled over in his femme clothes.

The text alert chimed again: "Good job, I knew you still wanted to be a slut. Come in the sliding door, last one on the ground floor."

Horrified, Nick looked up and realized that each of the rooms did indeed have an exterior, porch-style door. The one furthest from his car was clearly open; the curtains inside billowed out slightly.

"Don't even think about moving your car," came the next message.

He'd have to walk past nearly a dozen hotel rooms and thirty cars to reach that door. Plus the three semis beside him were of the sleeper cab variety and could very well have someone in them. There was no way--

"I'm counting seconds and have my belt," said the next message.

Nick hurried from the car and across the lot as fast as he could on the tall heels, aware that the loose skirt barely covered his ass normally, and the breeze across the pavement seemed to be constantly blowing it even higher.

One car engine came to life as he passed and he turned his head just in time to lock eyes with a very surprised looking older guy, then Nick was finally up on the sidewalk and pushing his way past the blowing curtains and into the hotel room. He turned and reached for the door to slide it shut.

"Did I tell you to close the door?" asked Mr. Chase.

Nick abandoned the door and rushed to the middle of the room, dropping to his knees at the foot of the bed, next to where Mr. Chase stood. The other man wore a white hotel bathrobe. Standing, he was a few inches taller than Nick, but Nick rarely stood in his presence. His dom hadn't changed much in the previous year; he was probably 50 or 55, and in the kind of shape that indicated almost daily workouts and healthy eating.

Nick expected the robe to open next and despite his earlier attempt to convince himself he was done with this life, his mouth started to water. Instead, though, Mr. Chase picked up the thick leather belt lying on the bed.

"It looks like Slut's forgotten her manners," he said. "And you took way too long in that parking lot. Put your shoulders on the floor."

Nick leaned forward, still on his knees, lowering his shoulders and face to the floor. The movement pulled the hem of his skirt almost up to this waist, and Mr. Chase flipped it the rest of the way over with one hand. "Here we go," he said, and without any other ceremony the first stroke of the belt cracked across Nick's ass.

He yelped involuntarily; it was a hard stroke, and it had been a long time since he'd taken a spanking. Mr Chase laughed. "Been a while, has it?" He swung the belt again, hard, and despite bracing himself Nick cried out again. "That's okay; if your screaming brings a cop in, we'll just invite him to use the nightstick on your ass."

Two more strokes and Nick's ass burned, but he managed not to make any more audible reactions.

Finally, Mr. Chase dropped the belt on the bed and told him to get back on his knees. The robe was already open, and when Mr. Chase said, "Open," Nick stuck his tongue out, lips wide. Mr. Chase put one hand on the back of Nick's head and drove his semi-hard cock directly down Nick's throat in one fast thrust.

Nick gagged and struggled for a moment, choking on the fast intrusion, but Mr. Chase didn't let him back off one bit. His nose remained smashed against the other man's smoothly shaved pubic bone, and he felt the heavy balls pressed against his chin. The cock in his throat pulsed two or three times, growing harder with each heartbeat driving blood into it.

Finally, Mr. Chase pushed Nick's head back off. His wig was anchored in place with a solid array of bobby pins and Mr. Chase knew he could manhandle his crossdressed slut pretty roughly without dislodging it. With a hand firmly squeezing each side of Nick's head, the dom fucked his mouth hard and fast, like he would any other slut's pussy.

"Oh, I missed this," said Mr. Chase as the wet, smacking sounds filled the hotel room and spit flew out of Nick's mouth. It dripped down his chin an onto his women's blouse, and he tried desperately to keep catching his breath very time the thick cock partially withdrew.

Abruptly, Chase shoved Nick's head completely off his cock and turned to the desk. He handed Nick a suction cup dildo shaped very realistically like a cock somewhat smaller than his own. He also tossed Nick a small bottle.

"Slather that up, set it on the floor, and start riding," he said.

"I don't--" started Nick.

"You didn't do anal," Chase corrected him. "But I told you you're in for a first experience today. Get that lubed up and get your ass on it before I bend you over and just shove it in."

Nick briefly considered calling the scene off entirely. He'd never had anything other than a former girlfriend's finger in his ass before and had always been staunchly "nothing anal" when playing with other men. But now that he'd had a cock in his mouth again he found he wanted to keep going, so he squirted a ton of the lube onto the cock, then awkwardly rose up on his knees and tried to brace the suction cup end on the cheap faux-wood floor.

"Let's go, Slut. I'm going to see you bouncing up and down on that thing before the day's over. And I might get the bigger ones out too."

Nick finally felt like he'd positioned the tip of the dildo correctly, so he slowly sank back down on his knees a bit. The tapered end pushed straight into his anal ring, so lubed up that even when he tried to squeeze his ass tight the toy encountered little resistance. He froze instantly, afraid to go too far, too fast.

Mr. Chase laughed. "There we go. You're going to be begging for it by the time I'm done with you, but for now I suppose I'll let you go at your own pace." He grabbed Nick's head again and without warning shoved his cock right back down to the hilt in Nick's mouth. As he started fucking his sub's throat again he said, "You'd better keep working your way down that. I expect to see the toy's balls touching yours shortly."

So saying, he started fucking Nick's mouth with a very familiar intensity. With each stroke he'd pull out until the tip of his cock was right at Nick's lips, then drive enough of the length into his throat that Nick had to gasp for breath and pray he wouldn't gag each time. It was even more difficult than usual with one hand bracing the dildo against the floor; he was slowly sinking down on the toy, and each time he tried to rise up on his knees to give his ass a bit of a reprieve, Chase's cock went that much deeper into his throat. Nick kept working his own body up and down, lowering himself a bit more with every repetition, until he realized that the thick base of the toy was pushing against his ass each time.

"Oh, yeah, there we go," said Mr. Chase. "Turn and put your back to the bed."

Nick pivoted awkwardly, the dildo still lodged in his ass, until his back was straight against the foot of the bed. From there, Chase made me stretch his legs out and spread them, so that he was sitting flat on the floor, completely impaled on the fake shaft.

He was also completely impaled on Mr. Chase's real cock. With the back of his head pressed up to the bed, he couldn't retreat at all from the other man's thrusts. Chase fucked his mouth for a few minutes in that position, then stopped with his cock still fixing Nick in place. He reached into the pocket of his robe and puled out a long, silky blindfold, which he wrapped twice around Nick's eyes and tied off behind his head.

"All right, now we can get down to some more fun," the dom said as he resumed his face fucking. "If I remember correctly, you're the slut who claims she doesn't like cum. Always just want it on your face..."

Nick tried to say "Yes sir" but the throbbing shaft in his mouth muffled his words too much. Besides, Mr. Chase knew Nick's preferences and limitations damned well. Nick was sure this was just rhetorical talk. Throughout the dozens of meetings they'd had over a two-year stretch he'd always finished by covering Nick's face with a huge coating of cum.

"Time to change that bullshit," Chase said. "You can't be a proper Slut without a healthy craving for cum."

Suddenly, Nick felt Mr. Chase's body tense up. He panicked, raised his hands to try to push the other man off, but Chase caught his wrists easily and pinned them to the bed. He pulled his hips back slightly and Nick felt the cock retract from his throat, leaving just the tip inside his lips. But that realization was pushed aside immediately as pulse after pulse of thick, salty liquid splashed over his tongue.

"Don't you spill a goddamn drop," grunted Mr. Chase, still blasting his cum into his captive's mouth.

Nick tried to protest but had to clamp his lips down to keep the load from escaping his lips; he couldn't believe how much liquid was filling his mouth. Just when he thought he was going to start choking and spraying the cum everywhere, the torrent finally abated and he felt Mr. Chase relax. The dom's cock stayed partially lodged in his mouth, though.

"Next step, Slut," Chase said. "Swallow that down."

Nick shook his head the tiny amount he could in his pinned position and made a sound like "Mm, mm."

"Swallow," commanded Mr. Chase.

He wasn't going to get out of there without following orders, Nick realized. They'd established safe words long ago, of course, but he'd never anticipated a situation where his mouth was so full of cum and cock that he couldn't invoke one. Besides, if he did use the safe word, even after swallowing, their encounters would be done. And despite the two unexpected firsts he realized that he'd truly missed being Slut and didn't want the arrangement to just end.

So, he swallowed. His first time of tasting a man's load and feeling it completely coat his throat nearly made him gag, then he DID choke just a bit as Mr. Chase drove his cock completely back down again. He pulled out quickly, though, halfway.

"Clean it, Slut. Let me feel that cum-swallowing tongue."

Nick bobbed up and down, swirling his tongue around the thick shaft. Mr. Chase's hands were still locked around his head, so when he heard applause he realized with horror it wasn't just the two of them in the room.

"Thank you gentlemen," said Mr. Chase, still pumping away at Nick's mouth. "I'm glad you enjoyed that. Who's next?"