Chapter 5
Ross
I was a bit on guard with my first job, and I kept a close eye over my shoulder and at my back as I walked into the hotel. I trusted Melanie, but this all seemed a bit too good to be true. I hoped that these clients were good people and not some crazy fuckers who would tie me up and take all of my money. I wasn’t for getting rolled, and even though I knew people hooked up like this every day, one still had to be careful, male or female.
I thought about the men that Melanie serviced and wondered if she ever got scared or had anyone get rough with her. She wasn’t exactly a tiny woman, but she was still not muscular or strong enough to manhandle anyone or get herself out of a situation.
I approached the door to the room number on the card that Melanie had given me and knocked.
A few moments later, a woman, who looked to be around thirty-five, slender and attractive, opened the door and smiled. “Hello, you must be Ross. I’m Claire Richard.” She stepped aside, and I went into the room with her.
“Yes. Melanie told me that you were attractive, but I had no idea you’d be so beautiful.” The woman was pretty, but I was just buttering her up. She was definitely above average, but she wasn’t the most gorgeous woman I’d ever seen. I might pick her up in a bar, fuck her for one night, but she wasn’t my type. But that wasn’t what this was about at all. I didn’t have to be attracted to her in any sense; I didn’t want ever to see her again, all I had to do was ram my cock in her and make her come like a fountain.
“You’re sweet and very handsome.” She walked across the room and lowered herself onto the bed. “Melanie tells me that you’re also very talented, and you can guarantee me a nice, wet time?” She lifted a brow, and I nodded. I was confident that I could give her what she wanted and she wasted no time undressing and lying back on the bed.
She was a pretty blonde with nice, plump lips, a small waist and big, though fake, breasts. The little tuft of hair that covered her mound was a perfect match, which told me her blond hair was one of the only natural things about her.
I stood at the end of the bed as she rubbed her legs together and parted them as if playing peek-a-boo with me and undressed. Her eyes followed my body down and up again, meeting my eyes with a look of approval. “Very impressive.”
My stiff cock was ready to do its job, and I decided I’d prime her with the vibrator she left on the bed. Melanie had told me she would encourage the customers to bring their toys, but just in case, I had brought a tiny egg vibrator to stimulate her clit. It was vital to a good, splashy orgasm, and made my work a hell of a lot easier.
I turned it on, and the hum was nice and steady as I lay it across her clit. “Good luck with that thing. I’ve tried a hundred times to make myself come with it, and I can’t make it happen.”
I rubbed it around, and she moaned, grinding her hips upward. I slipped the vibe in and worked it in an upward position. She cried out and covered her mouth. “Oh, my, Ross. You do know right where to touch a woman.”
“Just wait until I get my big cock in you, you’re going to come your head off.” Her eyes widened, and she squealed with excitement as I worked her. Then I let her hold the vibrator a moment while I sheathed my cock and then I took it over again. I spread her legs wide and tilted her hips as I centered my cock into position.
“Mm. I almost forgot, will you use the clamps and cuffs on the nightstand?” I glanced over to see that she’d brought along some nipple clamps and fuzzy hot pink handcuffs. I lifted a brow, and she smiled. “I’ll pay you a hundred more.”
“Sure.” I took the handcuffs and brought her wrists together above her head and locked them. She let them fall back over her head, and I knew she’d be helpless to do anything about the nipple clamps. “You sure you want these?”
“Yes, please. And if you could spank my tits and jerk those off during my orgasm?” She wasn’t fazed at all about her requests, and I shrugged.
“Which orgasm? You’re going to have many.” I set the clamps in place, and they were attached by a loose chain which lay against her breasts.
“Whichever you like, Sir.” Something about the way she’d said sir had my dick even harder than I’d imagined and once I had her clamped and tied, I centered myself back against her wet slit and nudged my cock in. She was a tight fit, and I wasn’t sure I’d be able to get all the way in, but that wouldn’t matter, what I needed was only about two inches inside and upward. The magic button, also known as the g-spot.
I thrust my cock hard, and she jumped and cried out, “It’s so big and hard, Ross. I’ve never known one so hard. Ever.” She winced as I worked it in and then soon enough I was fucking her nice and steady. I worked her hole a bit, and she came once, giving me what I’d need. That initial come, no matter how minuscule it was, was like a doorway to the floodgates, and after that, I had her worked into a frenzy.
She brought her hands down and rubbed her tits, teasing the nipple clamps which I wasn’t quite ready to rip off. I wanted her to be good and tender first.
Her channel tightened and the grip of her button, which was super spongy against my cock, told me that she was almost ready so, I held that vibrator on her clit relentlessly until she was begging.
I met her eyes as I steady fucked her. “Do you feel that pinch?”
“I feel like I’ve got to pee.” She tightened her walls, and I shook my head.
“That’s not pee; you’re about to come, let it come, Claire. Don’t hold back.” I ground my hips against her button and pulled away allowing the dam to break free. Her soaking come gushed, and her eyes widened.
“Oh, my! I did it!” She celebrated as I continued to fuck her and I couldn’t help but belt a laugh. She did too and then, in a moment, she relaxed, and I thrust hard against her, pulling my cock back only as needed to give her room to spray. As she cried out, her pussy spurting more hot come all over my cock, soaking my balls, I reached up and jerked her clamps off, and she came again, this time getting splashed in the face as I thrust against her with a wet slapping noise.
The hotel’s room service would be angry, but by the end of the session, I had her laying in soaked sheets, panting for breath with tears in her eyes.
“I never thought I could. Thank you so much. Your dick is so hot and so incredible. I’d like to have you again next week if possible. Maybe midweek?” She kept twisting and pinching her legs together, and I could tell that there was something going on.
“Midweek isn’t going to work for me.” I leaned in and rubbed her mound. “Are you sure you’re finished?” I slipped my hand up her thigh and parted her, inserting three fingers into her channel and sure enough as soon as I touched it, she gushed as a dam had burst, her come soaking my hand.
She writhed on the bed with tears flowing steadily. “Thank you. Oh, you’re so amazing. I’ll pay you double if you can do midweek. Please.” She was breathless, and her money was good. It wasn’t like I had a lot of people willing to pay me that kind of money for my time or my body. Yet. Melanie seemed to think that it was all going to work out, and how could I turn down money?
“Okay, Wednesday?”
“Yes, please. And I’ll make sure to put new batteries in my vibrator. You sure gave it a workout. And me one as well.” She let loose a soft giggle.
“Well, I’m glad you enjoyed yourself.” She handed me the money, and I counted my hundreds before I stuffed them into my pocket, and sure enough, she’d slipped in a couple of extra crisp hundreds.
I raised a brow, but she held up her hand. “You’re so worth it.” Too much of that type of praise was going to have my ego soaring.
I waited for her to shower and leave before I got cleaned up and then I got in the car to head home. I decided to call Melanie and tell her thanks and to let her know how it went.
She let out a long sigh. “Ross, please tell me you’re in a good mood, and all went well.”
“I’m in a fantastic mood, and all went according to plan, and it was so successful that Claire tipped me two-hundred extra, and booked me for Wednesday.”
“That’s great. So, it wasn’t that bad, huh?”
She sounded a bit out of breath, and I had to wonder what her night had been like.
“No, it wasn’t. I’ll do it again. It’s the easiest money I’ve ever made in my life. I just wanted to say thanks. I finally feel like things are looking up.” I let out a sigh of relief, and she let loose a giggle.
“I’m so relieved. I worried you’d hate it and then I’d have to disappoint the others. You have quite the schedule building, and I’m sure that they’ll want to see you again after. The next job is a bit different. It’s the one where the lady would like her husband to watch. Is that going to be a problem? They are a nice couple, he’s in his fifties, and she’s twenty-nine.” The age difference seemed okay, and no one was too young, so I’d play along.
“Sounds good to me, especially since I saw the rates.”
“It is always going to be more money anytime there is more than one person. The parties are the best rates. You’ll make a killing and the best thing about those, once one person has a party like that, then the others at the party will want to have their fun too and you’ll get other bookings. Just wait, you’re going to have some fun, especially when you get used to the clients. You’ll be like family.” She let loose another giggle, and I couldn’t imagine being so intimate with another couple that I stopped seeming like a job. I trusted her though.
“It’s exciting, to say the least. I’ll see you for our weekly appointment?” She said she wanted to continue seeing me for our fun.
“Yes, I can’t let these girls have all the fun. Be sure and save a nice big load for me. Don’t go giving it all away.” Her voice was a scolding tone, and I laughed.
“Oh, I promise I won’t give it away, but I can’t promise I won’t sell it.” We shared a laugh, and when we said goodbye, I had hope that things would be okay for the first time since losing my job.
I just couldn’t let anyone close to me find out what I was doing. Above all, I had to protect Katie, and she could never know the lengths I’d gone through to take care of her.