Gary's Golf "Outing" Chapter 9 Hair of the Dog

by: Germaine 
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Rating: XXX Add Review    Added: 04/19/2007
Complete: no 
Synopsis:Gary plays his first game of golf in drag.
Categories: Crossdressing / TV  Humor  She Males 
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Gary's Golf "Outing" Chapter Nine -- Hair of the Dog

Back in the bed room Christie and Kimberly laid out my outfit for my first round of golf in drag. I put on a pair of pink silk bikini panties and a matching pink silk bra. Kimberly put breast forms in the bra that looked like real breasts; they even had nipples. I put on a short-sleeved pink golf shirt, but balked at the short black skirt that lay on the bed. "I can't wear that; I never saw a skirt that short. Everybody will see my panties."

"That's not a skirt, sweetie. That's a skort."

"What the hell is a skort?" I asked.

"Look. A skort is a short skirt with shorts under it. See? Nobody will see anything but your beautiful legs," she said as she spread the skort for me to step into. I did and she pulled them up and zipped them up on the side. I looked into the mirror and started to get a hard on. They really looked sexy. I put on little footies that had little pink pom-poms at the heels and white sneakers. Then Kimberly put the wig on me that I had worn last night and brushed it down on one side, almost over my eye, and back on the other side. She said that would let me keep one eye on the ball and keep me from being distracted. She helped me with my makeup and I was ready to face the world.

Christie looked fantastic in a white cotton short-sleeved golf shirt and bright red shorts. She wore a bright red matching ribbon in her hair that would keep her hair from falling into her eyes. I helped Kimberly hook her black bra and helped her tuck her tits into the cups. Now I really had a hard on. She put on a short-sleeved black golf shirt, white satin bikini panties and a short white skirt; not as short as my skort. "Okay, ladies, are we ready?"

"As ready as we'll ever be," I said.

Christie and I got into one cart, Kimberly took the other and off we went. This was my first time out in drag in daylight and I was more scared than I was last night. I almost had a panic attack when the cart sputtered and died half way to the club house. I got into Kimberly's cart to make the broken down cart lighter. Christie steered the disabled cart and Kimberly pushed it with hers. We kept our fingers crossed, hoping this one wouldn't break down, too.

Actually, Kimberly didn't keep her fingers crossed. She put her hand on my bare leg and said, "Bob will cream in his pants when he sees these legs. He didn't get a good look at them last night; they're gorgeous."

"Oh shit, I forgot all about Bob," I said.

"You forgot about Bob?" she said incredulously.

"Well, I didn't actually forget him. How could I? That was I night I'll never forget, nor do I want to. It was fantastic. Thanks for all you two have done for me. This is the wildest weekend I've ever had."

I patted her hand and she moved it up under my skort and caressed my hard cock. "Actually, sweetheart, this has been pretty mild. Stick with us and we'll really show you wild."

"Do you think Bob will really think I'm a girl?"

"The only way he could tell is by your voice. You'll just have to keep pretending you have a sore throat. Oh, he might be able to tell one other way," and she shook my cock and laughed. I laughed, too.

"There is one other way he could tell. Don't let him kiss you on the cheek. He might feel some stubble, especially this afternoon. Make sure he kisses you on the mouth. He'll like that better anyhow."

"I will, too," I said.

"You little vixen, you," she laughed and she shook my cock again and squeezed it. "You liked sucking his cock, too, didn't you?"

"Couldn't you tell?" I said.

"I think we may have created a monster," she said, laughing at the double entendre as she squeezed my monstrous cock again.

"You better watch it or that thing's going to spit at you."

"Okay, okay," she said as she removed her hand and slid it seductively down my bare leg. "I don't want you creaming all over my skort."

We made it to the club house and now I had to face Bob. Now I was really scared. He was busy with some customers when we walked in, but he waved and smiled as we walked over to look at the clothes hanging on the racks. We examined them like real women do, and held them up to one another to see how they would look on us. When the foursome left Bob's counter, we went over and said good morning. Kimberly and Christie both kissed him on the mouth, so I did, too. He held my hand and slipped his tongue into my mouth, so I returned the favor. God, right here in broad daylight! They have created a monster.

He said, "You ladies have a 35 minute wait for your tee time, so why don't you go out to the putting green and I'll call you when it's your turn." I started to follow Christie and Kimberly but Bob said, "Wait a minute, Gabrielle, I want to show you something. Come on around here. I went around the other side of the counter and he said, "I told you you would need another dose of medicine for that sore throat. Get under the counter; I want to show you something. Wow! You have beautiful legs!" I blushed a little and got down on my knees under the counter so nobody would see me. I could see Bob's cock was hard and he trembled as I brushed my hand across it. I reached up and unzipped his fly and took his pulsating prick out of his pants.

"Do you see what's on the head of my cock?" he whispered.

"Yes I do," I said, "But it's not going to be there long."

God, this thing looked even bigger in broad daylight than it did last night. And it felt harder, if that could be possible, I thought, as I took his man meat and guided the lipstick covered head to my eager lips. I kissed it tenderly on the little pee hole and licked the head with my tongue. Bob moaned and leaned into me and I sucked the smooth head into my mouth and laved it with my tongue to remove the lipstick. He trembled again and began thrusting into my mouth. Then he jumped like I had bitten him and said good morning to an approaching customer.

"Good morning," I heard a cheerful woman's voice reply. "Can you fit me in somewhere? I'm by myself today."

"This is perfect timing; I just signed in three ladies. I'm sure they'll enjoy having you in their foursome." He jumped again because this time I did bite him. He was teaming us up with a real woman! She'll surely know I'm not a real girl.

"You mean those two dykes on the putting green?"

"They're not dykes," Bob said indignantly.

"They're not? You should have seen them when you were dancing with their girl friend. They were whispering and giggling like two school girls. By the way, where is their girl friend?"

"She came in with them. She must be around here somewhere."

"Maybe she's in the ladies' room. I'll go take a look. I wouldn't mind getting into her pants."

"Holy shit! They're talking about me!" I thought, and it was turning me on. I began to suck Bob's cock in earnest and he was having a hard time controlling himself.

"Did you get into her pants last night?"

"No, I didn't and you shouldn't ask. She's a real lady."

"Or maybe she's a dyke, too, like her girl friends. Well, I'm going to find out before this day's over. I'll let you know," and she went to look for me in the ladies' room.

"Whew! That was close," Bob whispered. "Does she have you pegged wrong! She has no idea you're the greatest cock sucker in the world and you were sucking mine right under her nose." This was more exciting than last night, I thought as I sucked and bobbed my head up and down on Bob's sweet shaft. I knew he was getting close to cumming and I wanted to taste his sweet syrup before that bitch came back from the ladies' room.

"H-h-hi," he said to someone who came in to register to play. He went about his business as I went about mine. He was trembling all the time he was talking to his customer, and as he said, "Have a good day" to him, Bob had a good day right in my mouth. He filled it with the warmest, sweetest load of love juice I had ever experienced. Of course, I hadn't been sucking cocks for a full day yet, but this was sheer ecstasy. His cock exploded like a fire hose and filled my mouth to overflowing. I wanted to keep it in my mouth and savor the flavor but I was afraid I would spill some and stain my pretty pink shirt, so I had to swallow it before I had drained his dragon of all it had to offer. No sooner did I swallow a load than it filled my mouth with another load. I loved it, and when he was finished cumming and I had licked every pearly drop off his softening schlong, I had an idea. I kissed its head tenderly and put his prick back in his pants. And then I asked him if he wanted me to stay here for the rest of the day. He said that was a great idea, but he had to give some lessons so we'd have to do that some other time.

He took my hand and held it, then pulled gently as he said it was safe to come out. I kissed him on the mouth and forced my cum-covered tongue into his mouth. He sucked on it and cupped my ass cheeks and pulled me tightly into his crotch. I thanked him for starting my day right and went out to play my first round of golf as a woman.