by Alexa Land
Finally I reached the hotel, and as I crossed the lobby, the middle-aged guy behind the reception desk watched me carefully. He’d also been working the first time I was here and was probably putting two and two together, figuring out what I was. I’d been kicked out of more hotels than I could count, and the confrontation always made me feel like trash. I was worried that was about to happen again, but he let me go without incident.
Finn was waiting in the open doorway when I got upstairs. His face lit up as soon as he saw me. The moment I was inside the room and the door was closed behind us, he scooped me up into an embrace. He actually lifted me off my feet, and I wrapped my arms and legs around him and held on tight.
“I’m glad you’re here,” Finn whispered, rubbing his cheek against my hair.
“Me too.” I said, nuzzling his shoulder. He smelled good, like soap. His hair was still slightly damp, too. He’d gotten cleaned up for me.
“You don’t have to say that.”
“I know.”
He pulled back a few inches to look at me, then kissed me tenderly before carrying me to the bed. Another little white envelope was lined up on the nightstand beside the lube and the box of condoms. After we kissed for a while, he looked in my eyes and asked, “Is it okay if I undress you?”
“Of course. You don’t have to ask.”
“It feels wrong not to.”
He started with my shoes and socks, kissing each foot as he uncovered it. My jacket was next, and I raised my arms for him so he could pull my t-shirt over my head. He kissed my chest and stomach, then took off his short-sleeved button-down shirt before stripping off my jeans and briefs.
He ran his palm over my stomach, but then he hesitated. During our first session, he hadn’t touched my cock. Not that that was unusual. The men who paid me were there to get themselves off, not me. He laid down on his side beside me and said quietly, his palm still on my stomach, “I want to make you feel good, but I’m worried about doing something wrong.”
“You can’t really mess this up. Just touch me the same way you’d touch yourself.”
“I…um…I don’t just want to use my hand,” he said, clearly embarrassed by that admission.
“You can’t really mess that up, either,” I said, “unless teeth are involved.”
“That’s exactly what I’m worried about, not being careful enough and hurting you that way.”
“Don’t overthink it.”
“I overthink everything. I also feel guilty about how one-sided everything was last time. You didn’t even cum when we were having sex.”
“If you want me to, I can jerk off while you’re fucking me and cum for you.”
“No, see,” Finn said as he sat up, “that’s the problem. I want you to cum because what’s happening feels good, not because you’re putting on a show for me. I know I’m paying you, but I hate feeling like you’re just enduring it and not enjoying yourself at all.”
I sat up too and said, “I do enjoy it. I like being with you.”
“Really?” I nodded as he studied me closely. He asked, “What would make it even better for you?”
“Honestly, you and I would both enjoy it more if you let me initiate a bit. You can tell me what to avoid, and also just tell me to stop if I do something you don’t like. As it stands right now, I’m pretty limited in the ways I can give you pleasure.”
“I didn’t want to feel out of control of the situation. It’s probably pretty obvious that I don’t know what I’m doing though, so I forget what I said. Just don’t…um….” A blush rose in his cheeks and he looked away.
“Don’t what?”
“God this is embarrassing,” he muttered, but finally he admitted, “I’m not used to having stuff inside me. I was worried you’d do something before I was ready.”
“I’m glad you told me. I’ll be sure not to finger you or—”
“No, see,” he interrupted, “the thing is, I, um…I want you to do that.” He put his hand over his face. “This is the most embarrassing conversation ever. I knew it’d be incredibly awkward to try to tell you what I wanted. It was part of the reason for my rule about not doing a lot of talking. I was trying to avoid this.”
I knew I should give him some space, but for some reason I did the exact opposite, curling up against him and nuzzling his shoulder with my cheek. “You never have to be embarrassed with me, Finn. I’m here to make you feel good, and the more you can open up to me about what you want, the more fun you’ll have.”
“I’m not really an opening up kind of guy. In fact, I’m the exact opposite.”
“Try to let this be your one exception. I mean, you’re spending a ton of money and I feel guilty about last time. No way was what we did worth a thousand dollars. I really want you to get your money’s worth this time around.”
Finn dropped his hand and looked at me. “You’re right, it wasn’t worth a thousand dollars. It was worth a million. That was the best night of my life. On top of that, I took up ten hours of your time, which deserves compensation.”
“Still though, I don’t want to feel like I’m taking advantage of you. Let me earn my pay this time.”
A little smile played around his lips. “You don’t want to feel like you’re taking advantage of me?”
I grinned, too. “That’s right. Now how about laying back and letting me show you what I’m capable of?”
His lips parted and he drew in his breath. “One sentence and I’m instantly hard.”
“Good.” I rubbed him through his jeans as he kissed me. He hadn’t been kidding.
Finn stripped himself quickly and settled back against the pillows. I slid between his legs, took his cock in my mouth, and slid my lips to its base before dragging them slowly back to the tip. “Holy shit,” he exclaimed. Already? He had no idea what he was in for.
I concentrated on giving him the best blow job of his life over the next half hour, bringing him right to the edge before easing him down again. I did that again and again, and it was really gratifying to watch the way he responded. Finn started out trying to keep it together, but toward the end he was crying out and writhing beneath me, both hands gripping the bedding.
I could have just left it at that and finished him off, but based on what he’d said earlier, I eased my mouth off him, stroking his cock with my hand as I asked, “Do you want me to finger you?”
He could barely speak, but managed to rasp, “Yes. Fuck yes. Please.” He parted his legs for me and I squirted some lube on my hand before letting a little run over his hole.
I took his cock in my mouth again before sliding my index finger inside him. He was incredibly tight, but I felt him trying to relax and let me in. Before long, he opened up enough to let me slide my finger in and out of him as I sucked him. When I grazed his prostate, he bucked his hips and moaned, low and deep.
I built him up again, then eased him down, sucking him as I worked his hole. Finn’s entire body was shaking and his head was thrown back. I was surprised he hadn’t asked me to finish him off, but I decided it was time to do just that. I began sucking him hard and fast as I massaged his prostate.
He cried out when he started to cum, arching off the bed. I slid my mouth from his cock and he erupted all over his belly, then onto his face and hair and the wooden headboard behind him. I wrapped my hand around his shaft and milked his orgasm, my finger still inside him as he bucked and thrashed around. His yells were almost sobs, his hips pushing his cock into my fist again and again, both hands white-knuckling the bedding beneath him as his muscular body glistened with sweat. He looked incredibly beautiful, totally lost to his pleasure like that.
I brought him down slowly, eventually easing my finger from him. When it was all over he laid on the bed shaking and gasping for breath, his chest rising and falling rapidly. One of his legs had been bent and he let it fall to the side, totally exposing himself to me and completely oblivious to it. “I’ll be right back,” I said, rolling off the bed and heading to the bathroom
.
I washed up, then dampened a cloth with warm water and brought it and a hand towel back to bed with me. As I sat beside him on the mattress and wiped the cum from his face and hair, he whispered, “Thank you.” I grinned at him and washed his chest and stomach, then quickly wiped down the headboard. I tossed the wet washcloth through the open bathroom door and dried him off with the hand towel. Once I’d tossed that too, he pulled me into his arms. “I mean it,” he said, his voice a bit raspy. “Thank you. I just….” He shook his head. “I had no idea. Absolutely none. I thought an orgasm was an orgasm. That was…my God. How did you do that?”
I said softly, “I’m glad you liked it.”
He rolled over so he was facing me, cocooned me with his big arms and draped his thigh over mine. I settled in comfortably as he lost the battle with his heavy eyelids. “Liked it,” he murmured. “Huge understatement. Huge. That was life-changing. It was…my God.” His voice trailed off. He was asleep in the next moment. I felt surprisingly content as I let my eyes shut.
*****
Sometime in the middle of the night, a tender kiss on my cheek pulled me out of a deep sleep. The room was dark, and Finn’s arms were still around me. He kissed my cheek again, then ran a line of kisses along my jaw. When I stirred, he said, “Sorry to wake you.”
“It’s fine.”
He nuzzled my ear and said, “Do you think it’d be okay if I did the same thing to you that you did to me? I mean, it won’t be the same. Not even close. You’re extraordinary and I’m, well, me. But is it okay if I suck you? I need to make you feel good, Chance. I need that so bad right now.”
“Of course.” I kissed him, cupping his face with my hand, and he returned the kiss before shifting around and kneeling between my legs. He kissed and licked the tip of my cock, then wrapped his hand around my shaft and began jerking me off. His movements were hesitant, but when I said, “That feels really good,” he seemed to gain a little confidence.
Finn took a couple inches of my cock between his lips and tried sucking on it, his hand still wrapped around my hardening shaft. I pulled a couple pillows behind my head and stroked his short hair as he explored me with his lips and tongue. Gradually he got bolder, taking a little more of my cock in his mouth and sucking harder, encouraged when I moaned softly. What he was doing really did feel terrific, and I relaxed and let myself enjoy it.
He was trying hard, even to the point of accidentally gagging himself a couple times, and his efforts were paying off. I felt my orgasm building after a while and whispered, “I’m close, Finn. You might want to pull off.”
He did, but only long enough to look up at me in the darkness and say, “I want to taste you, is there any reason not to?”
“No.”
That one-word answer was all he needed. He wrapped his lips around my cock again and started sucking me hard. “Fuck,” I muttered, letting my eyes close as I threaded my fingers into his hair. I needed just a push to take me over the top, and when he cupped my balls, that did it. I moaned as I came, shooting again and again, my cock twitching in his wet mouth.
Afterward, as I caught my breath, he gathered me gently in his arms again and asked, “Was that okay?”
“It was so good. I guess it’d been a while since my last orgasm, sorry. That was probably more than you bargained for.”
“I loved it,” he said, reaching up to stroke my hair as I put my head on his chest.
After a pause I said, “Here’s a little public service announcement for next time you give someone a blow job, just because you seemed concerned. The rule to remember is ‘spit or swallow, don’t let it wallow.’ I learned that from the San Francisco AIDS Foundation. In other words, if you hold cum in your mouth, it increases your risk of infection. Sorry to, you know, get all over-explanatory on you.”
“That’s fine. Thanks for caring.”
“Just so you know, I get tested every six months and I haven’t had unprotected sex in years, so you don’t have to worry all that much with me. But it’s just something to know in general, especially if you visit another prostitute.” I felt kind of stupid for rambling on like that and added, “I didn’t mean to get all after school special on you.”
Finn chuckled a bit, his chest rumbling beneath me. “If only there had been an after school special about blow jobs. That would have been really beneficial. And thanks for looking out for me, but I actually already knew that. I’m a firm believer in doing my homework.”
“That’s good. Safety first,” I said.
“Mmhmm,” he murmured as he leaned in and kissed me.
His erection grazed my thigh and I reached down to stroke him as we kissed. After a while I asked, “Feel like fucking me?”
“I will if you do that for two more seconds,” he said. Then he smiled, his teeth a flash of white in the darkness, and said, “Aaaand, we’re there. What should we do? I’m open to suggestions. You could continue your educational programming.”
I sat up and swung my leg over him, straddling his hips. “You might enjoy a program called Chance Rides Like a Cowboy.”
That made him chuckle again. “Perfect.” I fumbled for the lube and condoms, and he reached over and turned on the lamp on the nightstand. “I really should watch you do this, for purely educational purposes,” he said with a smile, and I grinned at him.
I rolled a condom over his cock and slicked it with lube before lowering myself onto it. Finn moaned as I took all of him in me and started to ride him. He stared up at me with an awe-struck expression, and I rested my hands on his shoulders to steady myself.
He maintained eye contact as he reached between us and gently stroked my cock, asking, “Is it too soon after the last time, or do you think you could cum again?”
“I know I can.” Between his thick cock massaging my prostate and the hand-job he was giving me, I was proven right a few minutes later. I shot onto his chest and he came soon after, thrusting up into me as he moaned and grasped my hips.
My legs were shaking when I slid off of him and removed the condom. “Back in a minute,” I said, then hurried to the bathroom and repeated the wash cloth and hand towel routine, cleaning Finn up before snuggling into his arms.
“You’re so incredibly sweet,” he told me.
“So are you.”
He chuckled at that. “If you said that to anyone who knew me, they’d call you crazy.”
“Well, you’re sweet to me.”
“I feel better with you than I do with anyone else. You’ve even got me talking! I don’t do that.”
I grinned and said, “You don’t talk?”
“Not much. I usually limit small-talk to reciting the Miranda rights.”
Now it was my turn to chuckle. “You’re funny, too.”
“Again, no one would ever believe you if you tried to tell them that.”
“Well, then I’m lucky that I get to see what no one else does,” I said as he hugged me and rubbed his cheek against my hair.
*****
There was another note waiting for me the next morning. It said: Thank you again for last night. It was perfect. I don’t have my schedule yet for next week, but I’ll call you when I know my days off. I’d love to see you again.
I was both pleased and surprised that it seemed to be becoming an ongoing thing. I liked the overnighters with Finn, though I wondered how long he’d be able to afford them. I rolled out of bed and headed to the shower, looking forward to the luxurious orange-scented soap and shampoo.
Chapter Seven
“Oh my God,” Zachary whispered as we stood on the sidewalk in front of Nana’s house, pushing his once-again-black hair out of his eyes. Granted, it was a lot to take in. The three-story Queen Anne mansion was both regal and whimsical at the same time, the latter because it had been painted top to bottom in a sheer rainbow. Since the trim had all been left white, the effect was actually really pretty, and less ‘the circus is coming to town’ than it could have been.
“Explain Nana to me,” he
said as he stared up at the façade.
“Well, let’s see. Some of her grandsons are gay, and I think that’s what pushed her to be such a strong ally. That kind of explains the giant rainbow. Also, her family used to be in the mafia, that’s how they made their money. I guess they’re basically retired now, but that explains the mansion. Other than that…well, you just have to meet her and see for yourself. Nana as a whole kind of defies explanation.”
Zachary looked concerned as he glanced at me, but I said, “You’ll love her. Jessie, too. Come on.” I led the way up to the front door and he trailed a couple steps behind me.
Nothing happened for a couple minutes after I rang the doorbell. When I rang it again, there was another pause before the big, white door swung open and muted, pulsating techno music spilled out. “Hi Chance,” Nico said, stepping back and holding the door open for me. “I hope you weren’t out here long. Everyone’s upstairs and I was studying in my room. I wasn’t quite sure I heard the bell at first.”
“It wasn’t long at all,” I said, stepping into the huge foyer as Zachary took my hand. When I glanced at him, he looked dazed. I’d been like that too, the first time I came here.
“It’s like something out of a movie,” Zachary whispered, standing so close to me that our bodies touched. That about summed it up, between the marble floor, the huge crystal chandelier, and the sweeping staircase on the right curving up to a second floor gallery.
“Nico Dombruso, I’d like you to meet Zachary Paleki. We’re supposed to be meeting Jessie, he wanted to work on my car.”
“Yeah he mentioned that. Jessie’s really excited about it,” Nico said. He extended a hand to my companion and gave him a friendly smile. “It’s nice to meet you, Zachary.”
He looked up at Nico with wide eyes. “You too,” he said softly as they shook hands.
“Nana’s leading an exercise class upstairs in the grand ballroom and last I saw, Jessie was DJing for her. Come on, I’ll take you to him.” With that, Nico turned and led the way up the staircase. Zachary and I both checked him out automatically. He had a pretty incredible body, and the rear view was impressive.