Helping Stuart
After the Australian Open, winter set in. I mean, really set in. In a Boston kind of way. Cold, nasty winds off the ocean. Snow and rain and sleet and some other precipitation I didn't know the fucking name of. When Chris wasn't training and I wasn't teaching, we spent long hours in bed staying warm. And not just fucking, although that certainly took our minds off the weather.
We zoomed with Goran almost every week just to check in and he said the weather wasn't any better in the Czech Republic. We had a threeway jerk off session with him a couple of times and he watched me suck Chris' cock. You have to make the fun where you can in that kind of weather.
One Sunday we lay in my bed drinking coffee and I was trying to read a book. Chris was scrolling on his phone and I assumed he was looking at social media or porn or both, but it turned out he was checking out real estate listings.
I leaned over his shoulder and said, “You still looking for a place for us to live?”
“Yeah...I think we really need to. And Mike...I think we need to leave Boston.”
I felt the same way. Boston is by no means known for tennis. I said, “Where were you thinking?”
He looked at me and I could tell he was thinking. He said, “I was speaking with Brad and he gave me some ideas. He knows where a lot of the players end up. I suppose you do, too?”
I nodded and said, “Monte Carlo: That's the most popular one among the top seeds. No taxes.”
He scrolled on his phone saying, “I don't even know where the fuck Monte Carlo is.”
Laughing, I kissed his cheek, then said, “We would be close to Goran...”
He looked interested. “Really?” He found it on his phone. “Right. Mediterranean and all that. The Czech Republic is not far at all.
Then I said, “The Bahamas I think is another...but Chris. We can live wherever the hell we want. Wherever is convenient. It looks like you're going to have the cash.”
He grabbed my face and said, “We are going to have the cash.” He kissed me and licked my nose. Very sweet. I could tell I was blushing and he kissed me again.
I thought about getting under the covers and going for his cock, but since we had had sex a few hours before, it seemed greedy. I said, “Maybe we should think about it this way.” I pointed out the window to the sheets of some freezing precipitation blowing by. “Do we want someplace warm?”
“Fuck yeah! Warm. If I miss anything about Australia, it's that.”
“Right. Agreed. I've always wanted to live somewhere warm. Do we want to live in Europe or on this side of the Atlantic?”
He looked at me, but I could tell he was still thinking. “I don't know. There's more matches in Europe. Or at least the majors. And there's Goran...but we can't make him the reason, right?”
“Yeah, I know. But he's becoming a good friend. It would be awesome.”
“You just want his dick.”
“Is that so bad?”
He chuckled, but kept scrolling on his phone. We obviously weren't going to figure this out in one conversation. I went back to my book.
--
The next day I went to the tennis school. It was still raining/snowing and the sky was this colour of grey I can't even describe. I realized we couldn't get out of this fucking place soon enough. But then again, we would miss our friends.
I taught a few students and then went to the coffee room. Stuart was sitting with a big mug of coffee. I didn't see any other teachers. I felt like I hadn't talked to him in weeks, which was probably true. We rarely talked. I sighed inwardly and sat down. “Hey, Stuart.”
He looked up from his phone and gave me a half-smile. That was unusual. He said, “How are you, Mike?” I stared at him as if he wasn't speaking English.
What was going on? I said, “Oh, fine. This weather is getting me down.”
“I know, right? How is Chris?”
He never asked me about anything. It was freaking me out. “He's good. Training hard. Brad is keeping him busy.”
He nodded. Brad was only working half-time at the school now and the owner was looking for another teacher. Stuart cleared his throat and said, “Uh...Mike...do you want to grab lunch?”
I almost fell off my chair. What the fuck was going on? “Really?”
He looked pained, then said, “Yeah, I know. You and I haven't really clicked, right? I just thought...well...it might be nice to get to know you.”
I swallowed all kinds of snarky comments and said, “Sure, Stuart...let's go to Midge's.”
It was a sandwich place down the street the teachers – and students – often went to.
We put on our rain gear and headed out into the weather. We got to Midge's and ordered our lunch and sat down. I decided to wait and see what was on his mind. He took a bite of his sandwich and chewed for a minutes, then said, “So, you and Chris...you've really got a good thing going, right?”
He seemed genuine. I was half-expecting something homophobic, but this was anything but. “Yeah, we do. Love, and all that.”
He smiled. I mean he really smiled. His eyes smiled. And you know the thing that really floored me, that somehow in the few years I had known him and hung out with him, was the fact that his smile was beautiful. His face became all elfin and lovely and his short red hair and his freckled face was actually adorable. How had I never noticed? I thought about the fact that when you don't like someone, you don't really see them. You just see what you don't like, not the person. He said, “That's awesome, Mike. I'm really happy for you.”
I had to say something now. “Ok, Stuart. What the fuck? You and I have never had a real conversation in what? Three years? I've always had the feeling you thought I was an idiot and that you were a homophobic ass. When I came out, I expected you to stab me or something. What gives?”
He looked really sad and then I felt like a shit. But my point still stood. He took a sip of his water and looked around the restaurant for a second, then back to me. He finally said quietly, “I'm sorry, Mike...”
He stopped. He was clearly torn up about something. I said, “You're sorry?”
“Yeah. The thing is...well...I'm gay. But even at age twenty-nine and in this world where everyone and their dog is coming out as whatever, I've been afraid to do it. Come out. And that has made it even harder because I feel like there's something wrong with me. It's so easy, right? Why can't I just do it?”
I was stunned. But I kept with it. “That's a good question. Why do you think?”'
“I don't know. Well, I guess I do. My parents are born again fucking Christians. They were all about me being a tennis star, but there was no room in their world for a gay son.”
“That's shitty. I'm sorry. Have you...had any relationships?” I realized I was afraid to ask
“Oh, here and there. You remember Sean Franco?”
I did. He was a teacher at our school when I first got there. Cute guy. “Yeah...did you and he...”
“We did. But I was too scared and he didn't want to wait for me to calm down and come out.”
I remember that he left the school all of a sudden. Now I understood why. “That sucks, Stuart.”
“It did. It really did.”
He had this sad look on his face and I wanted to hug him. I looked at him for a moment. His eyebrows and lashes were so light they reminded me of Chris. But Stuart's were reddish. He had a million freckles. Fucking cute guy. Again, how the hell did I not see it? I felt bad. I said, “Stuart...talking to you this way...I'm seeing you in a totally different way. It's freaking me out.”
“You're not the first person to say that to me. Sean said that to me. I think I do a really good job of being invisible. People just see the cranky version of me. And I do get cranky. You've seen it.”
“Yeah. You are a shit sometimes.”
“I know. But it's because I'm scared. I feel intimidated by everyone. You're all so...I don't know...happy.”
That really hit me. Then I said, “So why are we having this conversation, Stuart? Why now?”
He swallowed some more sandwich and said, “Because you and Chris...seem so good together. And now that Brad and Seamus have told everyone they're together and they seem so happy...well I just thought, what the fuck am I doing? Why can't I just try to be happy?”
That silenced me. I felt sad and guilty and a bunch of things. Not that it was my fault, but I realized that seeing Chris and I, seeing Brad and Seamus...it must have been agonizing for him. I eventually said, “So...you're in the market for a guy, then, right?”
He laughed and said, “Something like that.”
I said, “Stuart...I gotta say this. You are hot. You are adorable. I have no idea why I never noticed before. You could have guys falling over themselves to get into your pants.”
He seemed surprised. “Really?”
“Yeah, really. I would fuck you.”
That got him. He blushed. I mean he blushed all over his face and neck. I imagined he whole body was blushing. And he had a lovely body, that much I knew. He had quit competing a few years ago, but he kept himself in good shape. And I would. I would totally fuck him. In fact I wondered if I should suggest it. But instead I said, “Let's find you a boyfriend.”
“Yeah, whatever, Mike. It doesn't work like that except in movies.”
I ate the rest of my sandwich and said, “You never know...”
We went back to the school and I spent the rest of the day processing this totally unexpected conversation.
--
Later, having dinner with Chris in his apartment, I told him about it. He laughed and said, “I knew it! I just knew it!”
“You did? How the fuck?”
“There was just something about him. I can't explain it. But I'm really happy for him. That he let you know. Let's set him up!”
“Slow down there, Chris. That's not our job.”
He grinned at me and said, “Jack.”
I looked at him, amazed. He was right. “Holy fuck. That's perfect.”
With a sly smile, he leaned over and kissed me. “I'm perfect, aren't I?”
“Yeah, yeah. You are.”
--
So I set them up. I mean, I kind of set them up. I felt like an evil matchmaker. I convinced Jack to come to Boston and stay in the hotel down the street from me, saying we would hang out for the weekend. I convinced Stuart to go out to dinner with me. All friendly, nothing flirty. Then at the last minute I texted Stuart and said that a friend of mine had just got into town and did he mind if he joined us for dinner. Done.
I got to The Ocean Grill early and got a nice quiet table. Stuart came in and I could tell he was nervous. I wasn't sure why, but he sat down and looked tense. “You all right?”
“I never go out for dinner, Mike. Who is this friend of yours anyway?”
He looked suspicious. I said, “Oh...he's someone I've known for ages. We had sex a few times but he's just a friend. Jack Foster.”
Just then, Jack strode in. He looked amazing, as always. His hair was a little shorter, but still artfully arranged in brown waves. He was in this tight black shirt and even tighter brown trousers that showed off everything. I could almost see the outline of his cock in them. Wow. He got to the table and looked from me to Stuart. He said, “Hi, Mike...and this is?”
I said, “Stuart McFarlane. He's a fellow teacher.”
Stuart looked at Jack and I could tell he was impressed. Then he said, “You used to be a real star when we were young...I remember you.”
Jack looked uncomfortable, but gamely said, “Yeah. I left tennis.”
Stuart got up and shook his hand. “It's nice to meet you.”
Jack, for his part, was clearly checking Stuart out. Stuart was shorter than him, and slimmer, but like I said before, almost magically sexy. I felt good about the chemistry I was seeing.
We all sat down and had a nice dinner. The conversation flowed and Jack and Stuart seemed to be hitting it off. But I could also tell that they were both interacting with me in a slightly flirty way. Subtle, but there. From Jack, I could understand why, since we had traded cum a few times. But Stuart? I wondered if this was going to get complicated.
When dinner was done and we paid the bill, Jack suggested something I hadn't expected. He said, “Do you two want to come to my room...I've got some nice cognac...”
Jack had become a different person. Stuart said, “Room...?”
“Yeah. I live in New York so I have a room at the Brandeis Hotel.”
Stuart didn't say anything, but I could tell he was impressed that Jack was in one of the most expensive hotels in the city. We got up and walked the few blocks to the Brandeis and up to Jack's room. Well, it was more of a suite. He got the biggest room in the place. Three rooms, really. A bedroom, a little sitting room, and a tiny kitchen.
He poured us cognac and he and I sat on the sofa and Stuart perched on a chair across from us. We toasted to the shitty winter weather and had a sip. There was an awkward silence, so I decided to take charge and see where this was all going to lead. I turned to Jack and put my hand on his big, thick thigh. I said, “So Jack...it's nice to see you.”
He grinned at me. He knew what I was up to. Jack turned to Stuart and said, “It's great to meet you, Stuart. Why don't you come over and sit beside me.”
For a minute I worried that Stuart would bail. But he got up and sat awkwardly beside Jack who put his arm around his shoulders. I was struck by the contrast between Jack's brown hair and Stuart's short red buzz, by Jack's tanned face and Stuart's pale skin and its million freckles. Stuart's eyes seemed to bore into Jack's. I could tell he was turned on.
I ran my hand over Jack's crotch, massaging that amazing fucking instrument that was concealed by his pants. I reached over and took Stuart's hand and placed it where mine had been. Stuart went with it. He started to massage Jack slowly and Jack gasped. He pulled Stuart to him and – hallelujah – they started to kiss. Really kiss. Sloppy and deep. Stuart, for all his semi-closeted persona, certainly knew how to use his mouth.
I undid Jack's pants and hauled them down. He was in black boxer briefs that were full of his cock. The bulge was impressive. I pulled them down and his massive prick sprang out. It was throbbing. Stuart looked down at it and his eyes literally widened. To give him all the credit, he fucking grinned and got up. Just like that he started to shed his clothes. Soon he stood there naked, all pale and wiry and taut like the tennis player he was. His cock was a really nice size, much like mine and Chris. He was uncut and it was pale and pink at the same time.
Jack reached out and took it in his hand. He looked up at Stuart and said, “You are a sexy guy, you know that?”
Stuart gave it right back and said, “So are you.”
I decided to join the fun and I shed my pants and shirt and got down between them. I wanted cock. I got Jack to stand up and I fisted both of them, jacking them a few times while I sucked on their balls one after the other. Jack pushed my face down on his cock and gave me a few fucks which made me gag a little. Then I spat him out and turned to Stuart. I wanted to taste him. His cock was thinner and I was able to swallow it all, but it still hit the back of my throat and further. He took my head in his hands and he also fucked my face. I could tell I didn't need to encourage him in that department.
I glanced up and they were kissed really intensely, their mouths making all sorts of wet noised. Jack's cock was pressed against my face and I could feel it oozing precum that ran down my cheek. I came off Stuart and went back to Jack. I mentally relaxed my jaw and swallowed him, but his dick, that fucking long dick, pushed into my throat and I worked really hard not to gag. For myself, yes, but I didn't want Stuart to get freaked out.
Jack slid his cock in my throat a few times but I had to spit him out. I got up and pushed Stuart down and fed him my cock. I wanted to know what his mouth felt like. He didn't hesitate and grabbed the base of my dick and pushed it into his mouth, his tongue moving everywhere. He had clearly sucked cock before.
Jack kissed me a bunch and licked my neck, and then moved to my nipples, biting them and sucking them and then doing both. There was a lot going on in my body. But I still had a plan.
I said, “Let's hit the bed.”
I pulled Stuart up and necked with him for a moment while Jack jerked us both off, but then I pulled them both to the bedroom and we all piled on the bed. Jack said, almost shyly, “Stuart...can you fuck me?
Now that's exactly what I wanted to happen.
Jack got some lube and handed it to Stuart who seemed totally into it. He lubed himself up and jammed some fingers into Jack who was on his back with his legs spread. I moved up and fed my cock to him and watched Stuart slide into him deep. He bent forward and they were looking at each other. I said, “You are so fucking hot, Stuart. I wish we had done this sooner.”
He looked at me and said, “I totally fantasized about fucking you a bunch of times...”
I laughed and said, “Well, you may get your chance. But right now, you've got a job to do.”
Stuart actually giggled. It was sweet. But he was also the sexiest little fucker – next to Chris, of course – I had seen in a while. He looked down at Jack and said, “You want my cock, Jack? You want this cock to take you?”
Jack's eyes widened, shocked by this Celtic demon who just appeared. Remember what I said about the quiet ones? But Jack, ever eager said, “Yeah, give it to me, Stuart. Give me that cock.”
And Stuart did. He started to fuck and not gently. I was startled. I had expected him to be a total bottom, but he was clearly more complicated than that. I slid my prick into Jack's mouth again and watched the show. There was sweat starting to fun down Stuart's freckled face and Jack's hair was all over the place, his careful arrangement long gone. They stared at each other: electric blue and deep brown. I was as turned on by that as anything. I like watching two people really into each other. It's fucking fantastic to watch. I realized I almost came in Jack's mouth, so I pulled out.
Stuart was fucking hard and fast and Jack was just staring at him. Like he had discovered a new species. I thought: that's a good start. That's how I felt with Chris at first. Like: who is this guy?
So I got off the bed and quietly left the room. They didn't seem to notice. I put my clothes on and just before I left, I heard Stuart's voice. “Thanks, Mike.”
I grinned to myself and said, “You're welcome.”
I walked over to Chris' place. I had told him my plan, of course, and I was excited to tell him how it went. And I was fucking turned on, so I also wanted a lot more than that.
I got into his tiny apartment – which we would be happily losing as soon as we figured out where – and he was lying on his couch wearing nothing but really tight briefs, watching something on tv. I said, “I am a matchmaker extraordinaire. I left them with Stuart's cock in Jack's ass.”
Chris got up and immediately started to undo my pants. He said, “And you must be all horned up.”
“How did you guess?”
He pulled my pants off and I shed my shirt. I said, “Fuck me, Chris. I'm so turned on I think I might explode.”
Chuckling, he threw me on the sofa. He pulled the lube from under the sofa, left there when we fucked that morning and got us ready. He slid into me and pushed my legs up all in one motion. We were getting really good at this. He looked down at me and said, “Tell me what happened.”
“While you're stuffing that thing in me?”
“Yeah, while I fuck you. It's hot, right?”
“It is. Well first I got into Jack's pants and sucked him off for while. You know what that's like, right?”
“Fuck, do I ever. Did you take him?”
“More or less. He fucked my face...but it was hard. Remember?”
Chris kissed me, then said, “Oh yeah. That cock of his. Anyway, next?” His pale blue eyes were bright with lust. I love it when he's like that.
I kissed him with some tongue, then continued. “I got down and sucked them both for a while. Stuart totally used my face. But they were necking like crazy.”
Chris fucked me a little faster and said, “And Jack fucked your face?”
“He did. You have a thing for Jack's cock, don't you?”
“Who wouldn't? It's epic!”
I laughed and looked down and watched Chris' cock slide into me, his strong torso working, his thighs flexing. My Chris. I said, “I made Stuart suck me off for a while, which he did really well.”
“I bet he did. I wish I had been there to watch.”
We kissed some more and I took Chris ass in my hands, massaging his strong glutes, then snaked one of my fingers into his hole, circling it around. He groaned and fucked me harder.
I said, “Then it was the main event. Stuart turned into a sex god. I mean he fucking grabbed the lube and went to town on Jack's ass. He fucked like a pro. I think Jack was shocked. I mean, I was shocked.”
Chris smiled and he was clearly having trouble listening or talking because he was fucking me so hard and fast. His breathing was getting harsh. He was staring at me, a little grin on his face. He was almost there. I could tell. I said, “And then I came here. I came here to take your cum, Chris. Give me your fucking cum.”
And he did. He fucked really fast and his body tensed and I could tell he was doing just that. I grabbed my dick and in a few strokes, my cock did this thing it rarely does. It shot cum like a cannon. Each shot streaked out and hit my nose, my mouth, my chin and a few more onto my chest. It was nuts. Chris started to laugh while he filled my ass. He pulled out and licked my face, and then cleaned all the cum off me, and then fed it back to me in one big blog of cum that he spit in my mouth.
We kissed and writhed around the bed until we ran out of energy and just held each other. He raised his head off my chest and said, “Fucking hot. That's another reason I love you.” And he kissed me very chastely and I said, “And that's another reason I love you.”
