Almost Damsel Almost in Distress Ch. 06

He murmured his approval and grunted as I took him all the way down, holding him deep in my throat as I massaged him with my throat. He groaned and grunted as I deep throated him a few times, before I looked up and laid back on the seat, my legs up in the air.

I slipped my plug out of my ass, as he positioned his cock at my crack.

I whispered, "Take me, baby."

He obliged and slid himself deep in my sissy hole. I groaned as he slid balls deep on the first stroke. The plug leaving me open and the condom giving lots of lube for things to slide around.

He grunted in surprise, "Damn, you are tight."

"Oh, yeah," I looked up as he looked down. "Then tear my sissy ass open, baby."

He smiled and pulled out before slamming back in, grunting as he slammed into me. He began pumping and finding a nice pace. The sounds of skin slapping together as he pounded into me, I thrashed about and moaned and groaned like it was the best sex I ever had. It was a bit tame compared to what Alex and I routinely did really, but I was so horny I didn't care. Of course, the fact that I was whoring myself out had my arousal into the stratosphere.

"You gonna cum baby?" he grunted out between thrusts.

I bit my lip and nodded my head, I wasn't sure, but I was close, so I was going to make a show of it either way. My customer sped up, the sound of our slapping bodies matching my groans. As he slammed into me hard, I finally crested and came hard, feeling my lover pound hard into me. Since I was cumming, it took me a moment to realize I missed the feeling of being filled with cum because of the condom, but better safe than sorry, I guess.

My lover finally finished his orgasm and collapsed on top of me. It was strange to feel and see a different guy on top of me. It made me realize how much I was falling for Alex. I also wanted to be a good whore and please my customer and my Master, so I rubbed my client's shoulders and arms as he panted for air.

He finally lifted himself up and looked at me, "Sorry, but wow! That was fucking amazing. I haven't cum that hard in forever." He had been shrinking and popped out of my ass. He took the condom off and I took it from him to dispose in the wrapper. I slid my panties back on as we climbed back into the front and he soon dropped me back at my corner.

"I hope I'll see you again," he called as he drove off. He was watching me more than he was watching the road, so I was worried he was going crash, but he made it out of the area okay.

I got a message from Alex a moment later. "How was it? Enjoy your whoring?"

I texted him back, "It was fucking amazing. I was so turned on."

"Good," he replied back. "You'll be on duty for a few hours."

That reply made me squirt with excitement and shiver with fear. Sure enough a few minutes later another car pulled up. I went back to work.

All total I made sixty dollars over the next few hours, and I did sissygasm once more, so it was a very wild, very exciting time. It was also a lot of work. Anyone that thinks hookers and prostitutes don't work, should try selling themselves for a few hours. Just having sex for money sounds like a dream until your on your feet for hours and dealing with some smelly or not clean guys.

After my last John dropped me off, Alex pulled up and I was happy to get off my feet. I settled back in and took all the money out of my top and gave it to Alex.

Alex grinned, "You've been a busy bee."

"I've definitely been buzzing," I replied settling back into the seat.

"Tired, girl?" he asked gently.

I nodded, my eyes closing, "Yes, Sir."

"Well, you can't go to sleep yet. We have an appointment to keep," Alex smiled slyly.

What was he up to now? And why did him saying that make my heart flutter and my clit throb.

I nodded, "As you wish, Sir."

I dozed a bit as Alex drove. Clearly we weren't headed home, but it took me a little while to realize where we were going. We were headed to Ken's tattoo studio. It was getting late on a Sunday, I wasn't sure he'd still be open.

When I mentioned that concern to Alex, he just smiled and said, "We have an appointment."

Well, I certainly wasn't going to argue and before long we had pulled into the parking lot. Alex reminded me to bring my purse. As I grabbed it, he helped me out of the car and I tottered along with him into the shop. The overhead sign was off, but the lights were still on inside.

We came up to the door and Alex headed in. We both greeted Ken and he gave me an approving look. I came up and he kissed me on the cheek, "You look sexy as hell, Chrissy."

I giggled and played the bimbo a bit more, "Thank you."

I looked at Alex to make sure he was okay, but he was grinning as he watched us. I smiled at him and something about his look made my heart flutter and my clit throb.

Ken looked at me, "So, what are you looking for tonight?"

I smiled at him shyly as I toyed with my hair, I pointedly looked down at his crotch and licked my lips seductively.

"He means for your tattoos and piercings, girl," Alex's voice piped in.

I looked at him and stuck out my tongue. I was pretty sure I was going to get in trouble for that, but I was looking forward to the punishment, well, a little bit anyway. I turned back to Ken, "I'd like to get my ears, belly button and my nipples pierced."

Ken quickly set things up and with the piercing gun and before long, I had small silver studs in my earlobes. It was quick and easy, and yeah it pinched for a moment, but it wasn't bad at all. I wondered about a nose ring, too. But I figured I'd start with small changes for now. I didn't want to get too crazy, even though my horny brain was saying to do all the stuff I wanted.

Ken then had me undo my top and I sat back in the seat. He lined up and quickly had a barbell in my belly button. That was only a slight pinch. I then slid my falsies out of the way. It was only a moment later that Ken put the needle to my left nipple and had me count to three. As I counted three he quickly pierced it through and followed it with a silver barbell. Now that I knew what to expect, he pierced my right nipple. The pain was pretty bad, but was over in a flash, with me hissing and doing my breathing to ease the pain.

Ken went through the usual warnings about infection, watching for redness and irritation. I looked at myself in the mirror. The flash of the piercings was really amazing to see. I was even a little thrilled about the ear piercings.

Alex came up me and kissed my ear, gently, at the top, "They look great. Do you like them?"

I nodded, smiling up, "Yes, Sir. I love them. I can't wait to get more."

"I'm glad, I can't wait to play with them," he said. "Ready for your next tattoo?"

"Oh yes! Am I getting my tramp stamp?" I smiled biting my lip with my excitement.

"Are you ready for that?" Alex asked seriously.

I thought for a moment, my horny brain screaming to get dozens of tattoos all over. My reality kicked in from Alex's serious tone. It was nice to have him grounding me. I shook my head, "No, probably not. Its a nice idea, but I should probably get something else a little less intense to start."

"Any ideas?" Alex asked.

"No," I said. Then I looked up, "Actually, yeah. How about a heart on my ass?"

"A heart?" Alex sounded puzzled.

"Yeah," I smiled. "It will just be a red outline of a heart, then when I... get punished... the red of my cheek will fill in the color."

Alex laughed softly, "That's kind of wild. Are you sure that's what you want?"

"Yes, Sir!" I replied, really excited about the idea suddenly.

I moved back over to the chair and Alex explained what I wanted. Ken nodded and asked a few questions, but didn't show any reaction to the actual idea. I guess that's why he's a professional. Nothing people want will shock him.

Alex told me to lay face down across the chair and to hike my skirt up. I laid so my chest was over the chair, but my ass was hanging over the one side. I felt pretty vulnerable, so of course, that got me turned on, too.

Alex smiled, "I need to secure you to make sure you don't move while Ken's working on you."

I looked up, smiling slightly, my clit dripping with excitement, "Yes, Sir. As you wish."

He pulled the cuffs from my purse and cuffed my hands and ankles to the chair. Needless to say, I was almost panting with my arousal. Ken talked me through the process noting that this would be a little different, "The good news is you have lots of cushion back here, so it shouldn't hurt too bad, though I get the feeling you'd be okay if it did hurt a little."

I wiggled my well-cushioned ass, "Or a lot."

A smack on my ass from Alex, got my attention, "Behave, girl. Or I'll show Ken the color your ass will be when we fill in the heart."

I absolutely squirted in my panties at that point, "You can still show him, if you'd like, Sir."

"You naughty little minx," Alex laughed. "Its your ass. I'll just tan the one cheek."

With that he began smacking my ass, softly at first, but quickly building up until I could feel the heat radiating off my ass cheek. He gave me very little time between swats to recover, so I was slightly out of breath when he stopped.

"That's the color you want the outside of the heart to be?" Ken asked matter-of-factly.

Alex laughed holding my chin in his hands and looking in my face, "Yup, that should be a great match. Almost the same color as her face now."

I could feel the flush of embarrassment coloring my cheeks red at my public spanking. I knew Ken was the only one there, but somehow having an audience made it more embarrassing. Ken the professional had the tattoo needle loaded with the red color in a moment and he began inking my ass.

Bound as I was, I could really only hang helplessly as Ken moved the needle over my butt. Obviously this was a bit larger than my butterfly, so it took a lot longer. Thankfully, as Ken said, it didn't hurt much at all. There must have a nerve near one spot since it hurt a little more, but it wasn't as bad as the one spot on my butterfly shoulder tattoo.

I'm not sure how long it was since I kind of faded into my bondage mental space, but eventually Ken wiped my ass and announced simply, "All done. Want to get a picture?

Alex snapped a few photos of my bare, plugged ass then gave me another smack on my other cheek right on the spot that was red and sore from the spanking earlier. I gasped in surprise and pain.

Alex stepped in front of me, "Are you ready to 'take care of things' again, girl?"

I nodded, "Oh yes, Master. Please let me be a good sissy whore."

Alex then pushed the ring gag into my mouth and I squirted with excitement. Ken stepped around front and undid his pants. He stepped up to my helpless mouth and I stuck out my tongue. Teasing the hardening and already dripping tip. He groaned as I teased him with my tongue for a few minutes, until he wanted more and pushed himself into my defenseless mouth. He pushed in and I grunted with excitement as his long, thick cock quickly slipped most of the way through my mouth and partly into my throat.

As I began massaging the underside with my tongue as Alex began doing something with my plug. At first, he started vibrating it, varying the intensity and making me try to moan around the dick plugging my airway. Ken seemed to like that since he grabbed my head and began fucking my face very hard. He and Alex were saying something to each other, but I couldn't really hear it over the sounds of this cock sliding in and out of my throat. Whatever it was, Alex turned the vibe all way up making me buck against my cuffs and I really began pushing myself onto the meat gagging me.

After a few moments of that, Ken slid out of my mouth. I gasped for air, but I was also cock hungry and ready to be filled again. Ken stepped around behind me yanked out the plug and slid his cock home in my ass. I groaned through my gag with relief.

As Ken began slowly slipping in and out my ass, I looked desperately at Alex. He was smiling clearly enjoying watching me be my slutty self. I stuck my tongue though the ring gag, trying to beg for his cock in my mouth.

Alex stepped up to my helpless face, cupping my chin, asking, "You want your slutty mouth filled, girl?"

I nodded, moaning and running my tongue around the ring, trying to convey my desperation. Ken found a nice pace and was sawing in and out of my well-used ass as Alex teased me by just putting his finger in my mouth. I twirled my tongue around it desperately. He eventually pushed a second finger in and began gagging me with his fingers. This wasn't quite scratching my itch, but it was pretty good. So, I threw myself into it forcing my mouth down on his fingers, getting one into my throat.

"My goodness, sissy girl," Alex teased. "You really are desperate."

I nodded and kept pushing myself on his fingers as Alex plowed my asshole. Damn, he was fucking me hard and fast and with his big cock, I felt wonderfully full.

Finally Alex took pity on me and pulled out his cock and teased me for a few more moments before finally driving deep into my throat. I grunted in relief and Alex quickly began matching Ken's thrusts and I was getting spit-roasted by two large cocks, putting me deep in sissy bliss. It only took a few minutes of this treatment before I was thrashing and building to one tremendous sissygasm.

I shook, squirted and thrashed my way through a mind-blowing sissygasm that lasted for a good thirty or forty seconds. When I finally came back down, both guys were steadily plowing away at me and I threw myself into pushing back on both of them, squeezing my throat and ass, trying to make myself the best cock sleeve I could.

Even with my working hard the guys lasted for a while longer before Ken began to pick up and really started pounding my ass. I could barely hear the loud slapping over my gagging on Alex' cock, but after a few minutes of that pace Ken yelled and buried himself deep in my ass, I could feel his cum shooting deep in me. I was actually relishing the feeling of being so filled.

Alex pulled out of my gagged mouth with a soft plop, my drool running down my chin and dripping down.

Alex said, "You want to use her mouth to clean up?"

"Really? She's cool with that?" Ken asked.

Before Alex could even say anything, I started nodding, looking back to Ken and running my tongue around the ring.

The guys traded places and soon Alex was plowing away at my slippery ass while Ken used my mouth and tongue to clean his cock of his cum and my ass.

"Damn girl, with that mouth, I might have to cum again," Ken said. "I have to piss first."

"You can just use her," Alex laughed. "She likes it."

Ken looked down, but already knew the answer before I begged with my grunts and eyes. It only took a moment before he was using my mouth as a urinal. The sheer humiliation of it along with Alex pounding my ass had me on the verge again.

Alex began picking up his pace and was soon cumming in my ass which set me off again. I came even longer and harder this time and was panting breathlessly on the chair as Alex used my mouth to clean up.

I was suddenly very tired and rested my head on the chair. I don't really remember much, but soon I was uncuffed and stretching out my limbs. We said good night to Ken and I gave him a sweet kiss on the cheek with a thank you.

Alex pulled me close and supported me to the car and we headed for home. I leaned on his shoulder and dozed. That position had the advantage of keeping my tattooed cheek off the seat. Of course, that meant I was sitting on the spanked cheek. Ouch! I guess you can't have everything.

Alex supported me back up to my apartment. He opened the door and pulled me in for a kiss.

"I hope you had as much fun as I did tonight, girl," Alex said softly in my ear as I nuzzled into his shoulder.

"Oh hell yes! I hope we can do some more after we get the house fixed," I replied.

"Absolutely, my sweet, sexy, slutty girl," Alex kissed me sweetly. "Have a good..."

"Oh wait!" I said and scurried off to the kitchen.

I came back with a bottle a moment later and handed it to Alex, "Would you do me the honor of holding my chastity keys?"

Alex smiled softly at me, "It would be my pleasure, girl."

He took the frozen bottle with the small keys in the bottom and kissed me good night.

I wished he could stay, but I took solace that this was his last week on night shifts and we could hopefully start staying together more next week. I was sore. Well, tired and sore. I barely remembered peeling off my slutwear and climbing into bed, but I dropped off in no time.

To be continued...