Monday flew by. I dealt with a wardrobe that needed to be put away, priced tickets home and cleaned up the place after my trip to the gym. The workout was great, no one tried to get me to go home with them and I was eager for Terry to get home so I could feel out how he felt about coming with me to my Mom's.
At dinner I brought it up without being sneaky. "Terry, are you interested in coming home with me for Christmas? Really interested?"
He looked at me. "Are you really asking me to? I mean, you want your Mom to meet me?"
"Yes. I want you to come along. I want you to meet my Mom. She wants to meet you. We want you there, if you want to come."
The look on his face was a combination of joy and sadness. "Ok."
"Ok? Tomorrow I book tickets, my present to you."
If we hadn't been in the middle of a typical dinner rush I am sure he would have cried. Walking back to his apartment we held hands and walked in step. I felt wonderful. He asked several times if I really meant it. We made love that night and once again shared his bed while sleeping. Sleeping together is underrated.
Tuesday morning we were up early. Terry had things to do and I had to get to the gym. He gave me shit because he knew I was going to be well fucked by Scott after my workout. I told him I would be glad to come home and do to him what Scott did to me. He smiled and said to save it for Friday. What I didn't realize is I wouldn't see him until Friday.
Timothy was friendly and we worked out together. After we finished he said I should shower so we dressed and went to the loft. He went in first. I followed five minutes later. Scott, I never called him that to his face or to Timothy, made me wait longer than normal. When he finally walked up to be he was carrying a tray. Without speaking I put on the nipple clamps, the ankle cuffs, the wrist cuffs, the cockring and inserted the butt plug. The ball gag followed and finally a blindfold. I stood at attention and waited. He pulled the chain hanging from the clamps forcing me to follow him. My cock was raging at this point knowing he would bring me to heaven.
Restrained, spanked and fucked by dildos and his cock I had three orgasms. The entire time I was gagged. When he finished cumming on me he left. I was still restrained and unable to move. Lying patiently I waited. A pair of hands spread my ass open and a cock entered. Not a word was said as the mystery cock fucked me. It was a hard fuck, determined to give the owner maximum pleasure while giving no consideration to the bottom, me. If I had any cum left in me I would have shot again, it turned me on. When the warm cum hit my ass I wondered if it was Timothy. Whoever it was left. I waited. At least ten minutes passed before the restraints were released. The sound of footsteps leaving followed by silence. Standing up I removed the items in the same order I had put them on. The tray had been placed next to me. There was no rag or towel. I dressed with the two loads of cum still on my ass.
Once I was home I showered and then looked for tickets. Calling Jude to confirm he was traveling with us and the dates I ordered them and sent a text to both with the dates. I was thrilled to have bought the tickets, gifts to both of them whether Jude liked it or not, and have the money to pay for them. It was a lot more than I expected but it was a week away. Fuck it, I thought, I haven't paid rent since I arrived.
Terry told me he would be able to meet up that night. He didn't mention the rest of the week. Spending the rest of the day on line surfing porn, looking for pictures of me or Terry, I was relieved when Jude returned from work. We ate dinner and watched a movie, something we rarely did and went to bed. The fuck at Scott's place was enough for me to fall asleep without jerking off.
The rest of the week passed by slowly. Steve was happy to see me, didn't mention the surprise fuck, or his filming it. He was eager for a blowjob and I was eager to swallow his load, which tasted rather good. Terry bowed out daily leaving me bummed and I wondered if I would actually end up not having sex on Thursday, it would have been the first time since I had lost my virginity.
Thankfully Craig came through and had time to give me the relief I needed. Jude's cock received oral attention and I was hoping to spend the night with Terry on Friday. Once again he wasn't able to meet up. Jude was going out with some friends and invited me along. After dinner they decided to go out for a drink. Being underage I was embarrassed to have to decline. Getting into a cab I was feeling a little sorry for myself. Sure I had a fun time but I wanted to spend my Friday night with my boyfriend or at least a friend.
Leaving the cab I walked slowly up the front stoop. A man was standing by the door and turned when I was halfway up the steps. It was Charles, one of the guys from dinner. "Hi Sam. Hated to think of you spending the rest of the evening all alone."
It was easy to smile. Charles was easy to smile at. The entire evening I tried not to think about sex and done pretty well. Not once did I scheme about getting naked with any of the guys. Seconds after he spoke my phone rang. It was Jude.
"Hey Sam. Is Charles there?"
"Yes." How did he know?
"Do me a favor. He has had a really shitty week. This is a lot to ask and you can tell me to fuck off but would you ask him in and beg him to fuck you silly? He could really use it and I think you could too."
Surprised is an understatement. Shocked is closer to what I suddenly felt. "Ah, Sure." I barely go the words out before he interrupted.
"Excellent, thanks stud, I owe you." And he hung up.
"Everything alright?" Charles asked with a slight smile that just hinted at his pearly whites and his eyebrows raised.
"Yep. Just Jude wanting to tell me he would be late, not to wait up." I chuckled. "As if I was his dad or something."
Charles smiled a full smile and wow, my legs felt a little weak. Helping Jude out with this favor, which was a crock of shit, would not be a problem. I walked to the door, Charles stepped out of the way, and we went inside. At the door to the condo I looked at him, "Come in."
Turning on the light I removed my coat and scarf and took Charles' coat to hang up.
"Place looks good, different, haven't been here in a while." He started the conversation after my complete silence. Was I nervous? Hell no, I was horny and just knowing this stud needed to fuck was enough to bring my cock to life.
"It does? Different I mean."
"He has new furniture. It was well overdue, you should have seen the shit he had before, all second hand stuff that had been well used." We stepped in to the living area and he checked out the room while I checked out his ass. Damn.
"Really? Jude had crappy furniture? Doesn't seem like his style."
Charles laughed, "Oh Sam, you don't know how style less he was. Shit, he thought a chair was great if all four legs were the same height."
"No way! You have got to tell me more, I would love to have some dirt on him."
"It'll cost ya."
What? A blowjob? Fucking me in the window? "You want a bribe huh, how about a beer?" I had to keep it a little civil.
"Beer won't cut it, this is prime information. How about a Manhattan?"
"Manhattan? I think..." shit, what was a Manhattan?
"Sorry, I forgot you haven't spent time in the bars. Where's the liquor cabinet?"
I felt like a complete idiot, stupid, young and foolish. "Over here."
Stopping in front of the counter that served as our drink station I felt that wonderful jolt of sexual energy as his hand touched my shoulder blade.
"Let's see what you have."
It took about five minutes to mix the Manhattans. Charles explained what they were and how you can make the simple lower end, TFI Friday's version, coke and a maraschino cherry, or you can make the real thing. He had a way of speaking that was intelligent, almost refined, yet cutting when he intended to be.
"Here, taste it." He handed me a glass.
"Oh wow! That is amazing! Damn, it's strong too." The first sip was outstanding but much stronger than what I normally drink. "Is it always so strong?"
"Well, it is what you would call a sipping drink. I can't stand the word sipping, sounds so prissy, but it is something you drink slowly. Drink it too fast and you will end up stupid in no time."
"No kidding." Walking to the sofa and sitting down I wondered where he would sit.
"Learning to mix cocktails properly is a great skill Sam. Anyone can pour some coke into a glass and add rum, but mixing a cocktail to make it stand out will serve you well. There is a lot I can teach you Sam. Cheers!"
I raised my glass and wondered if all the innuendo was intentional or if I was just horny. He sat across from me on the nice leather chair, so soft it was buttery.
"Thanks for deciding to be here, I wasn't really up for sitting here alone."
"The look on your face said that and a whole lot more. I didn't feel up for fountain pours tonight and knew Jude had top shelf."
He lost me on his comment but I smiled as if I understood. "So tell me about Jude's terrible style!" My voice was that of an eager naïve kid, damn.
Thankfully Charles let my childish response slid and he began to tell me all about the condo prior to Jude upgrading. Funny, smart and a smart ass he had me laughing in seconds.
"Damn! That went down fast!" I looked at my empty glass and was surprised I had sucked it down already.
"Yeah Sam, it did. Remember this is a slow cocktail. Enjoy it."
"I will, at least the next one. Wait here, I want to try it myself." I went to mix my first Manhattan. It took me five minutes and I wanted to taste it but didn't.
"Here, let me know how I did." I handed the glass to Charles.
He took it, his hands large and strong. He held the glass for a moment and then took a sip. "Not bad for a beginner. Here, let's try it again." He stood up. I followed his fantastic ass.
"First thing about making another drink, use a fresh clean glass. Sort of like a condom, you only use it once." He didn't look at me when he said it but he did smile just a little bit. He made another cocktail and set it down. "Your turn." He said as he stepped to the side just enough to allow me to step in. The heat from his body warmed me.
Doing my best to follow every step I completed my cocktail. "There."
"Ok. Back to the living room."
"Aren't you going to taste it?" I was curious how I did.
"Not yet, but..." He picked up his first cocktail. Barely anything drank from it yet and downed it. "Another tip. Bars will push another drink before you finish the one you have, it makes them money. If the place has any class they wait to bring the fresh one until after you finish the first."
Picking up the first cocktail I mixed I took a sip then downed the rest. My throat burned. "That wasn't as good as yours."
He patted my back, energy charge! And we returned to the living room. Standing by the ottoman he held up his glass. I followed suit. "Taste it Sam." I took a very small taste. "Yeah, that is good." I smiled. He reached for my glass and took it from my hand.
"Very nice Sam. You are a quick study. Thank you." He handed me the cocktail he had mixed and sat down. "Back to Jude's taste. He has great taste in a few things, always did, people mostly. He knew good people and would keep the freaks and negative shits at a distance. Pretty sure most of his friends he has known for at least ten years. But fashion, decorating, food, liquor, his taste was typical small town. No offense Sam, but he stood out like a kid from the sticks. He was all over cheap and quantity."
Charles continued to weave a tale of Jude's transformation from a kid from the sticks to a man who looked like he was born into taste and refinement. It was interesting to me that he didn't mention anything about Jude's love life, sex life or porn past. Regardless I was loving the stories. Even more so I was loving the opportunity to watch Charles. Just under six foot, thick dark brown hair in a great cut and style, full lips, manly nose, a hint of stubble that likely had grown since he shaved this morning, he was a handsome man.
Then there was his body. He was more than solid. Jude worked out and looked great. Charles filled his clothing like a man who really worked out. He wasn't quite a weightlifter but he had the breadth and depth in his chest to signify a man who could life twice his weight without a struggle. His midsection was also solid but thick, strong. His legs matched his upper body so he wasn't into just the pecs and biceps. Oh, his biceps. Fuck they moved in his sleeve like a snake in its skin. Sexy was an understatement.
If Jude hadn't told me he was gay I wouldn't have guessed by looking at him. Yes he was handsome and built, but his manner of speech, voice, movements, and the things he said, nothing gave away that he liked dick. By the time we had finished the second cocktail I was feeling more than relaxed and offered to try again on the third.
"You trying to get me drunk Sam?" He joked.
"I don't think I need to get you drink and you probably can hold your liquor better than most." I winked and went to mix.
When I returned, fresh glasses this time, he stood and took off the cashmere sweater he was wearing. My mouth dropped open. Fuck me he was hot. He was wearing a dark red shirt, closer to maroon that was more dressy than casual but not too dressy. He smiled, folded the sweater and placed it on the back of the chair. Taking a glass he raised it and smiled. "Let's see how you did?"
"Very nice Sam. You have learned well." His smile was enough to melt my insides. Sitting down I wanted to ask him about Jude's sex life, but I resisted.
"Charles. Thank you so much for tonight." I honestly was very happy he was here and spending time with me.
"No need to thank me yet, the night is still young." He raised his glass to his lips and I swear he winked.