James had always been a bit cocky. True, he had a reason to be with his chiseled face, tight bubble butt and successful accounting business. But mixing his usual bravado with a new interest in all things western was proving an unbearable combination. Shit, I liked a good pair of chaps as much as any other red-blooded, thirty year-old gay American man, but James’s dressing-up and southern drawl would have been a bit much even if we lived in Texas… but in Connecticut?!
Saturday morning I called him early, a naughty idea having kept me _up_ the night previous. I had fantasized taking advantage of my friend’s sudden ‘cowboy-ness’ and have a little honest-to-goodness cock hardening fun in the process. We’d never been intimate James and I, but maybe the time had come.
“Come by around eight,” I said to him; we were planning to continue our weekend partying. “I’ll make us something to eat before we go to the club.”
I wasn’t really sure I would have to guts to make my budding plan a reality but when I began to scour the shops that late morning I was sporting quite a heavy erection. Although I had never treated a man the way I was planning on treating James the thoughts delighted me as I bought my outfit and the toys. I even joked to the tongue-pierced salesman at the sex shop (not a shop I had ever been in, by the way) that I might very well, be back for a cock ring.
I strolled to the front door when I heard my best friend’s knock. I knew how James would be dressed, but I delighted in the fact that when I opened my door and James set his baby-blues on me, he would be bowled over by how I _was_ dressed.
“Wow,” he said when I flung open my front door.
I was wearing tight, black shorts; my broad chest and tight belly bare under a leather fringed vest; black cowboy boots, and a hat, under which I had gathered my long curly brown mane. James stepped into my house and just drank me in from head to toe.
“Can’t handle it, cowboy?” I asked, slowly turning to afford my friend a full long view.
“I can handle anything par-ner” James declared.
“You sure about that?” I asked, spying the black bag lying on my couch.
“Stevie” James said, grabbing my shoulders and spinning me to him. For the first time ever my friend held me close.
He was ready; tight jeans tell no lies.
“James…” I said, feigning surprise. I breaking from his loose hug…hard as that was to do, to add: “…I never knew you cared!”
“When you look like this…” he began as I spun and crossed the thin carpet to my couch. “I mean, you’ve looked hot before, but…”
“Yeah, I know,” I agreed, reaching for the black bag. Buying and planning was one thing, but now with the moment upon me I was nervous about using the toys I had bought.
Not so nervous though not to do it.
“Why don’t you show me your big saddle-horn?” I said to my couch, fondling the anal toy through the bag
Relying on James ego, I knew it’d take no time to get my best friend to “shunk” down’ his zipper, “flump-flump” his boots off, “shlip-pa” his jeans off.
“Whenever you’re ready,” he announced and I slowly turned, plucking the red pony-tailed butt-plug from the bag.
“What’s tha…?” James exclaimed as I faced him.
Completely naked, my best friend stood with his thick erection at a growing half-mast as I held the anal intruder up for his perusal.
“You said you can ‘handle anything’,” I said imitating James’ drawl. His wide smile faded just a bit…but not his thick erection. I reached down with my free hand, keeping eyes on his and tickled his big cock even harder.
“Stevie, Stevie,” he sighed leaning in to me.
I looked down, determined to take as many moments as I could to look James over while I kept up keeping him up. He really did have a nice thick cock.
“Let’s see if we can get this up you,” I said, letting him go, stepping back and reaching into the bag for a little ‘squirty’ pouch of lube.
“Y’all really wanna do this,” James said, his eyes even wider.
Damn, this far in, obviously turned-on, shocked even with what I was doing, and he was till drawling like some underpaid extra from _Urban Cowboy_!
I don’t know what James was thinking as I lubed the red butt plug, stood their smiling, not saying a word, both of us knowing he was growing harder by the second. When I was done, I dropped everything I had been holding except the now lubed plug.
“Come on, a rough and tumble cowboy like you has had to have had a few things up his ass,” I said, and James smiled one last time, gulped and turned to my challenge.
“Stevie…” he said as reached down and spread his little hairy butt.
“I just thought,” I said, pressing into him, feeding the wet cool tip of the plug between his cheeks. “…I just thought maybe a cowboy should know how a horse feels.”
“Ah ha…” James exclaimed as I pushed through and up, deep into that pruned spot, inserting the tip of the plug just inside his ass. I stepped back and the synthetic tail of the plug, the ‘ponytail’ swished down between us.
“Now you’re a real cowboy, you really know what it feels like to be a horse.”