About The Author
Richard Saw is an Australian ex-pat with a British passport, who works for an American multi-national and does a very good impression of a Londoner when on the escalator at Piccadilly Circus.
His original piece of writing was The Eating Guide to Soho (now in its 4th Edition). So for the past twelve years he has been eating and drinking his way through London and only his sense of the surreal has stopped him becoming a huge food snob.
The author's Twitter can be found here https://twitter.com/gayjockgeek
Gary and I had played tennis against each other for years. We’d met in our twenties in a tennis group when we’d both lived in a big city and we instantly bonded. We had both grown up playing tennis, playing tournaments and following the professional events like the soap operas they were. I was better than Gary was, that was never in question, but we never thought that should stop us having regular hits. We’d meet up early in the morning on city courts and smack the crap out of the ball, me performing miracles at the net, Gary slamming laser-like groundstrokes from the baseline.
And then we’d go have breakfast together and talk about the various men we were shagging. Gary and I fooled around a few times in the early days. After all we were fit gay men in a big city. It was all good fun to be had. But we never were at the same place in our lives at the same times, so we never dated, and the sex drifted away as a fond memory down the years.
We were still catching up for regular hits on the court years later, when Gary sent me a picture of some fashion brand that was using the tennis look from the 1970’s… wooden rackets, tight polo shirts, you know the look. The only tennis look that had impacted fashion. Unfortunately.
‘So cute’ I texted back, talking of the model.
‘We should do that,’ Gary messaged back.
‘Do what?’
‘Get some old wooden rackets. Get the polo shirts and little shorts, some canvas shoes. And then play a match dressed like that.’
I laughed aloud. That was a genius idea. If we could find the gear, that is. ‘We gotta do it, I agree. I’ll get the rackets. You get the gear. That’ll be our mission.’
‘It’s a plan.’
Of course, it took longer than hoped for. I had to eventually purchase some old rackets in an auction and then convince a friend of mine to re-string them, so we could actually play with them. The clothing was a little easier but even then Greg told me he’d struggled. When we both declared that we were ready, Greg messaged me to come to his place early Sunday morning and we’d get changed at his place before going to a tennis court near his place in a school where we didn’t even have to book because no one used them.
The temperature was already climbing into the low 30’s as I jogged around to Greg’s. I was so impressed with the rackets I had, and how I’d got them ready to play. I couldn’t wait to play this match. I mean, I knew I would win, that was easy. I’d never come close to losing to Greg, but it wasn’t about winning.
“Greg! Buddy!” I greeted him at the door. “Holy crap!” I exclaimed as I took it all in. Greg was wearing a tight white polo shirt, perfectly pressed little white shorts that didn’t leave much to the imagination, white socks pulled up thigh-high and a pair of Dunlop volleys. It was iconic.
“What do you think?” He laughed.
“This isn’t retro,” I chuckled. “This is vintage. Here,” and I gave him his racket. “Have a swing with this.”
“Perfect,” he said as he swung the racket. “Damn it’s heavy.”
“I know!” I chuckled. “I had a little hit myself. It’s gunna be tough. So, where’s my gear?”
“In the bedroom,” Gary said, pointing.
I hurried in, closed the door behind me and picked up the… no. I couldn’t believe it. This was some joke. He wouldn’t…
“Gary!” I stuck my head around the door.
“Yeah?” He looked at me, all innocence.
“Very funny. Now where’s my shirt and shorts?” I asked him.
“You told me to buy the vintage tennis gear,” he smirked. “You didn’t say it had to be men’s clothing.”
“But I can’t…” I protested.
“No one well see,” Gary assured me. “I had to think of a way to even the odds. And I saw the dress in a vintage shop when I was getting my shorts and I thought, I know who will think this is funny.”
“Yeah, it is,” I admitted. And it was, and did I care? You could do these sorts of things with a real mate, and Gary was definitely the person to have a laugh with. “Fine,” I chuckled. “But your Bjorn Borg is definitely going down to my Billie Jean King.” I ducked back into the bedroom and stripped off out of my street clothes. There didn’t seem much fabric with these tennis dresses, and it was well tight over my big pecs, even if it was made with a woman’s tits in mind. And boy it finished short. Just over my bum crack…
“Gary?” I called out again.
“Yes?” he stuck his head around the door with a big grin.
“I can’t wear this. I didn’t bring any underwear with me,” and I gestured that you could see the tip of my cock underneath my dress.
“Here,” and he threw a pair of … frilly knickers at me. “I knew you never wear underwear. So, I was prepared.”
“You are too fucking bad for words,” I laughed, pulling the knickers up underneath the tennis dress. He’d even gone to the effort of getting my little socks with the pom-poms on the back. Damn that man.
Gary couldn’t stop grinning as I stood in front of him. “Satisfied?” I laughed. “You’re going down you male chauvinist pig,” I teased him. “Billie Jean is going to thrash you.”
We headed out of the apartment, across to the school playing fields and onto the tennis court. As always there was no one around, so we took some selfies of us in our kit and started to hit some balls. It was tougher than either of us imagined. So used to modern equipment were we, that we struggled to find the sweet spot of the racket or put the ball in the corners like we used to. Gary was taller and heavier than I was, and it seemed that while we both struggled, it was easier for him to swing at the ball and strike it heavier. I was used to rushing the net but I found my balls landed in the middle of the court and if Gary didn’t hit it past me, I struggled to hit a winning volley. Plus, my much better serve was totally negated, they seemed to land in the middle of the box, right into Gary’s hitting zone.
It wasn’t the only problem. The damn tennis dress kept restricting me as I tried to serve. And when I lunged for a backhand volley my big pecs, pushed up by the dress, kept getting in the way. It was weird too, feeling the dress creep up, exposing the frilly knickers. Did girls go through this? And where was I supposed to put the second ball? I’d seen girls put it up their knickers, but it kept popping out when I did it. Plus… and I couldn’t quite believe this, but Gary’s shorts were so tight I could see the outline of his cock. As I double-faulted to go behind 4-3, we crossed over at the net. I was sweating like anything, the leather grip on the racket frustrating me. Gary on the other hand looked cool and calm, in his perfect whites. I bent over to pick up the tennis balls – these damn rackets made it difficult to scoop them up – and I could feel Gary standing behind me. Oh god, I could feel his semi-hard cock against my arse in these silly, frilly knickers. That boy would do anything to break my rhythm.
“How’s it going Billie-Jean?” he whispered. “Maybe you shouldn’t be on a court with a man. Only place for a girl like you is on her back.”
I laughed. “It’s these damn knickers. So small.”
“I don’t know what you’re worried about,” Gary laughed as he took the balls off me. “Your cock is so little you don’t even need the knickers.”
I gasped. My dick was a perfectly good size, thank you very much. Sure, it was a grower and not a shower, and sure nothing like Gary’s thick 8 inches but… Now this should have inspired me to crush him. We always teased each other, and I never let a good insult get in the way of kicking his arse. But as I took up position to receive, I stared down the other end of the court. Gary smirked at me and stroked his cock. By the time he served I was still thinking about his cock and my return didn’t make the net. It seemed to inspire him on and three more hard serves later, Gary had the game. I hadn’t given up a set to Gary in years but here I was, struggling and as he strutted around the court, I made error after error, to give him my serve and the set.
We went to the net to grab a drink and change ends. This had to end, I had to take control of the match. “Well one set to me,” Gary teased. “That means your knickers are mine. Com’n, hand em over.”
“What?” I blustered. “What do you mean?”
“One set down, you lose your shorts. You can win ‘em back in the second.”
Gary sounded so confident that I never thought to challenge him, except to say, “But what if someone sees?”
“Can you see anyone around?” Gary pointed out. “Plus, your cock’s so little. No one is going to see it.”
I blushed again and without thinking, I put my racket down and peeled my knickers down, handing them to Gary.
“Good girl,” he chuckled as he put them in the pocket of his tight tennis shorts.
We got into the second set and I was determined to get ahead. Twice I broke his serve, but each time I immediately surrendered my own. The slippery leather grip of my racket meant I couldn’t serve like I expected to. When Gary held serve to take a 5-4 lead we changed over. “I break you here, I want the title as the better player,” Gary demanded.
“Not a chance,” I protested.
“Why? We’re playing tennis as it should be,” he claimed.
I don’t know what it was, but Gary had thrown me for a loop today. He had me thinking up was down, and left was right. I found myself unable to argue. “Oh, you can’t!” I protested. “You’ve got to let me have that.”
“All this time,” Gary smirked, “You’ve claimed you were the better player. And now we’ve stripped it back to proper tennis it turns out you’re just a little princess with a tiny cock trying to play on a man’s court.”
I blushed and stammered. “No Gary, please.”
Gary eyed me up and down, as I found myself trying to pull my dress down a little to cover my dick which – traitor it was – was staying as small as it could be. “Very well,” he said, taking a step closer to me, making me feel even smaller. His racket swung between my legs and nestled in my arse crack. “I’ll protect your reputation. I won’t tell everyone you’re not the player they think you are. But in return you’re going to lift that dress like a girl and I’m going to fuck you right here on this court. I’ll have your big arse out on show, begging for my cock, with that little tennis dress riding up as I slam into your arse.”
“But… but… my boyfriend!” I protested. “And we’re mates…”
“And we both know your big arse has been begging for a proper fucking for years, hasn’t it?” Gary pointed out. “And there you are running around town being the big top. We both know you need this. I just had to get you into a tennis dress to make you realise what you need.”
I gasped. Had Gary played me from the very beginning? “I don’t have much choice, do I?” I protested.
Gary just grinned back and gave me the balls to serve. There was no way I was going to lose this game. Five times Gary had match points and each time I ran balls down, striking winners. But Gary wanted the win even more than I didn’t want to lose. I slipped on the next point and my passing shot just fell wide. Gary rocked from side to side, cupping his huge cock in his tiny shorts and licking his lips. But I knew he was nervous and so I pushed him back and came forward confidently. His weak return floated but with him out of position I tried to be a little too clever and my volley floated just wide. Gary pumped his arms in victory, “Fuck yeah!” he roared. Gary never spoke like that and now I found myself staring at his biceps. How had I not known they were so big?
Gary walked to the net, calm as ever. As if this was his right, as if he had expected to win the whole time. I went to shake his hand, but he ignored it, as if to indicate we were not equals, instead he grabbed my head and brought his lips to mine. I almost melted in his arms as his tongue slipped into my mouth. “Come over here,” he whispered, as he took me to the side of the court where there was a single plastic chair. He sat down, spreading his legs as he did. “Go on,” he said. “Get it nice and wet and hard.”
There was nothing for me to do, but to get down on my knees, my big arse forcing my tennis dress up to leave me exposed, as I un-zipped his shorts and pulled out his cock. God it was bigger than I remembered. How had I not given into this cock when we were young? How had I not begged to suck it every day and spread my big arse for it? I took it in my mouth, and it tasted as salty and as masculine as I’d ever wished a cock to be. I licked around the head and struggled to get the shaft down my throat. It was bliss and I would have stayed that way had Gary not reminded me what I owed him.
“Time for you to give the man what he deserves,” he smiled, standing up and forcing me to do the same. One of his big hands pushed me against the wire fence, while the other lifted my dress up. Even though it had been exposed during that second set, now my arse was totally open, I could feel the cool breeze against it and I shivered. He slipped a couple of fingers in my mouth, forcing me to suck on them. And then Gary slipped them around to my hole.
“So tight,” he smiled. And he slipped down, burying his face in my arse. “Ohhh, ohh, ohhh,” I couldn’t stop myself from moaning as his tongue opened me up and got me even wetter.
“Are you ready for a big cock?” I heard him ask.
“Yes, yes, please, yes.”
“What do you say?”
“You’re the better tennis player,” I gabbled. “I admit it. I’m a little girl on the court against your man. Please fuck me, take my big arse and show it what it’s there for.”
“You need it bad,” Gary declared. “I knew you did. So good to hear you admit that I’m a bigger man and a better player. I’m gunna keep this tennis dress around. Don’t worry, I won’t make you wear it when we play tennis. I’ll just look at it to remind me what a little girl you are. And maybe I’ll make you put it on whenever I feel a nice big arse to drop a load up.”
“Yes, yes,” I agreed.
“And when you put that tennis dress on you’re going to take my dick any way I want to, aren’t you? I’m gunna fuck you nice and raw, dump a big load of my swimmers up there. Maybe get you pregnant.”
“Oh please!” I moaned as I could finally feel Gary’s cock resting at the opening of my hole. He was right, I hadn’t been fucked in a long time, but I’d spent all morning – from the moment I squeezed into this tennis dress – desperate for a cock to be inside me. I opened up for him, right there. “Aww fuck,” I groaned as I felt him enter me.
“That’s it,” he whispered. “Take it nice and deep.” Gary brought me back down on his cock and then lifted me up onto my tippy-toes, my little pom-poms pointing to either side as I let out a squeal, before sliding me all the way down, his huge cock filling me.
“Oh! Oh! Oh!” I had been missing cock like this and now I barely knew how to handle it. But Gary was there to teach me all over again. He kept sliding into me, not letting me catch my breath, not letting my prostrate have a seconds rest. Eventually though he lent back a little and without thinking, I sat back on him, and started to ride the cock all by myself.
“Oh baby,” Gary growled. He slapped my arse several times as I milked him, before grabbing my waist and holding my down as his cock throbbed and shot inside me. As he did, I felt my body react in pleasure and I felt my own dick, which hadn’t so much as grown an inch, start dribbling cum down my leg.
“That was amazing,” I whispered as Gary slowly withdrew. And it was true. It had been great sex.
“Come on,” Gary smiled. “Let’s get back to mine before anyone sees us.”
We both found ourselves looking around, realising we’d taken quite a risk and she grabbed our gear and hurried back to Gary’s place. We both chuckled and smiled at the whole scene, showering to get the sweat and cum off. It was like it had been great fun between friends, and great tennis. “That was a one off, wasn’t it?” Gary asked.
“Yeah definitely,” I laughed. “But an awesome one.”
We both agreed and I got back into my street clothes and picked up the wooden rackets. We hugged, a quick kiss on both cheeks and I headed off home.
But I’d taken two steps out the door and I found myself stopping. I couldn’t. I shouldn’t. But I turned around and knocked on Gary’s door. He opened it and I found myself trembling. “Please Gary I need your dick. I just need it bad.”
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