Gay Erotic Stories

Str8 Country Dude at Halloween…

First of all, guys, if you are reading the stories here, then guess what; bi, str8, gay or whatever, then enjoy life, its way too short. I don’t mean short on intelligence or safety; please life is too short, don’t help speed it along by being stupid. Second, never limit yourself or hide yourself by telling someone, “I’m x, y or z. We are limited by those self-inflicted locks that we place on our lives. Gay men are the most notorious for creating fake lives (especially on the internet or a resume). We can be anything on paper; it just doesn’t make it real. I take facts from everyone that I know, talk with or have encountered and spin stories, ideas or fantasies for each of us. Some are true and some have hints of truth. As far I am concerned, unless you know straight on yourself; then consider my word (written or spoken) to be the gospel.

The company Halloween party was last week. I still don’t know what possessed me to let myself be talked into that costume. There we all were at the office; yeah, even country boys can have a college education and hold down respectable office jobs.

There were a lot of arguments over making the party a mandatory, costume party. Everyone had their reasons. I simply didn’t know what to go in costume. I thought man it would be so easy to go as a cowboy. I have tons of boots and denim shirts, etc. Sandy, my best friend, looked at me and said, “Don’t even think it!”

“What I asked?”

“You’re not getting off that easy. I already see you trying to come in something that you wear all the time.” Sandy tells me, “You are coming over to my house on Friday and we are putting together something for you, so that you and I can win that $5,000 costume contest.”

On Friday after work, I stopped off at the local liquor store and picked up a large bottle of Jack Daniels and a couple of 2 liters of diet coke; then headed to Sandy’s. We sat around for about two hours discussing the options. She finally says to me, “I know what the perfect answer is; a cop and hooker!”

Now Sandy has some huge tits but I’m not the biggest of guys. I’m only about 5’8 and weigh about 160; very lean, very trim gymnast type from my working out. Sandy saw the look on my face and said; “Nope you have it wrong again. I’m going to be the cop and you’re going to be the hooker!” I spit and sputtered first and then started laughing until I cried. First, there’s no way I’m dressing up like a hooker. Second, there’s no way, I would pass as a woman, even with my build. I am a hairy little so and so. It’s all over from my legs, to my stomach/chest, up to my goatee and mustache.

Sandy starts her whining that on any given day has been known to break windows and set off car alarms. She finally has me talked into at least trying the silly idea. If it doesn’t work, we will switch roles. Thinking that I’d won, I agreed to the trial.

Sandy pours me a huge double straight of Jack and one for herself. We down them both, and mine immediately on top of the rest I’ve drank, causes my brain to go to mush. We go into her bathroom; she has me strip to my jock. Now, though we are both straight, she is my best friend. We’ve never dated or anything. It’s more of a sister/brother relationship.

She tells me to stand in the shower stall; puts an eye mask on me and tells me to simply stand still. All of a sudden I feel her smearing something on me from my feet/toes to my face; front and back. After what seems like forever, Sandy turns on the water and washes it off. When she takes off the mask, I look down and see that except for my pubes, that there isn’t any hair on my body anywhere. I start yelling in disbelief, “What the hell?”

Sandy hands me another Jack and we down that one. Now, for the sake of time, basically while my brain is still shutting down; she tweezes my eyebrows, takes down my pony tail, mullet hair and applies the makeup. Then after curling my hair, she leads, me into her bedroom and starts putting all kinds of crap on me. First, there was the corset, the fishnet stockings, the mini skirt, etc. Then she set me down on the bed and puts on the stiletto heels. During this makeover she had swapped my jock for a thong and had me push my beautiful dick back between my legs.

After all was said and done, she led me to a mirror and says, “Take a look.”

I opened my eyes, “Oh my God!” The woman in the mirror was a little slutty looking, but erotic, hot and beautiful. I looked at Sandy and said, “That’s me?”

She giggled and says, “Yeah, can you believe it? God, you could actually be a hooker or an escort!” Sandy left me there looking to shower, dress in her cop uniform and said when she was through, “Let’s go.”

We got to the boss’s house with the party in full swing. As we walked in, I kept noticing all the guys watching me. I started sweating, and feeling out of place. Then I noticed Greg, my cubicle buddy, looking at me with a funny look; like “I know you don’t I?”

He walked over to Sandy and says, “Who’s the fox that you brought with you?”

Sandy, says, “Greg don’t you recognize Tony?”

Greg, who is dressed like a Cowboy says, “What? No way!”

I look at him, smile and say, “Way…” with my drunken smile.

Greg yells out, “Hey everybody it’s Tony!” All of sudden, we’re surrounded by people asking a million questions. Sandy has become more popular with women wanting tips and men asking lewd questions. I tell her that I need a drink. Greg follows behind me to the bar.

I turn around in time to see Greg watching my ass. I ask him, “What’s up?”

Greg laughs and says, “Me man; I would never have guessed.”

“What?” I ask him.

He says, “If I saw you at a bar or on the street; I would think ‘hot chick’ or ‘let’s fuck’ or something; not oh my God, Tony, my straight, happy hour, cubicle buddy!”

We both laugh. I say, “Well I guess Sandy did an excellent job.”

He sighs, with a scary lustful sound and says, “Most definitely!”

After making the rounds, more drinks and lots of questions; I tell Sandy that I need some air. She is in the meantime talking to our boss about some project and trip and has lost her attention on me.

I grab the bottle of Jack from the bar, the bartender winks, I laugh and head outside. I find Greg outside getting air also. He sees my bottle and asks me to refill his glass. We go out for a walk around our boss’ estate gardens; finding a bench I tell him that I need to sit. While there, Greg says, “Can I ask what its like?”

I tell him, “At first? Nerve racking, but now, feels normal, I guess.”

Greg says to me, “You really don’t realize how hot you look do you?”

I look at him and say, “What?”

He says, “I never told you, but I’m bi and damn you combine the best of both worlds. I have a friend that I can talk shop with, drink with and who’s hot as a man and now a woman.” I look down, embarrassed. Greg, says, “Tony, don’t worry, I expect nothing more than our friendship.” He puts an arm around me and without a blink, I turn to him and we kiss. Next thing I know, we’re making out.

After a few minutes of this, Greg says, “Would you like to go back to my place and let’s see where this goes?” I simply take his hand and off we walk to his car. At Greg’s apartment we sit down in front of the fireplace and he slowly takes off my heels, sliding his hands up my stockings to my “hidden treasure.” He undresses me from the waist down and carries me into his bedroom. He then begins to suck my dick while running his hands all over my body. Greg reaches next to the bed and brings out lube and a rubber.

I put it on him. From there, he lifts my legs and slowly, erotically, rubs his dick in my crack. Once in me, we start making out again. Eventually, Greg starts moaning, and I can feel him filling the rubber that is inside me. Greg then reaches down and takes me in his mouth, and then it’s my turn to moan and shake as I fill his mouth.

We lie together and eventually drift off to sleep. During the night, I wake up, go into the bathroom, remove all the makeup, scrub myself clean and climb back into bed. I did think about leaving, but didn’t feel that I wanted to jeopardize my friendship.

In the morning, I wake up and there is Greg lying there watching me. He says, “You know, I think the chest hair would be hot if you let it grow back. The facial hair though is a no. You look younger without it.”

I lean over and kiss him, saying ‘thanks’. I tell him that I am glad that my experiment of alternative sex was with him. “Alternative sex?” he says, looking sad. “We made love.”

I realize that I’ve hurt him. “I didn’t mean to hurt you,” I tell him. “I’m still not sure what to say or how to say it.”

Greg says, “Let me ask you; do you like me?”

“Yes,” I tell him.

“Did you like last night?”

“Yes, again.”

“ Would you date me?”

I think for a minute and say, “Of course. You’re my friend and you made me feel more special than I have in a long time. Just don’t expect that version of me to show up often. I am a man, not a woman.”

Greg, says, “Dude, the country man version of you that I see right now, is as hot as anyone and he’s my friend.”

We kiss and then I feel Greg sliding a rubber on my dick. He says, “Tony, your turn to see what this ‘alternative’ version of our love is all about.”

Later, more about two cowboys knocking boots.