I knew a guy that would say, “You never know where your blessings are going to come from. Some people might find the use of this phrase objectionable or offensive, I for one think it’s spot on for what I am about to tell you.
My sister Lisa's friend's boyfriend's brother, Tommy, showed up for my carefully planned beach trip, invited by the boyfriend who did not think I needed to know. The car we planned to take wouldn't hold all of us and our stuff so instead of being a bitch (which was plan A) and telling him to take a hike we drove two cars. The boyfriend paid for gas as his punishment.
My sister and her friend wouldn't ride separately, and the boyfriend had to ride with them so that left me with a perfect stranger wearing an ugly ball cap climbed into the car with me. He was stoked, because I had the coolest car he’s ever seen and he’s seen a lot of cars, apparently. I’m sure it had nothing to do with the 3 beers he'd consumed while we rearranged the cars.
We were driving for maybe an hour and Tommy told me all about his fitness regimen (involves staring at girls in yoga pants at the gym and occasionally lifting some free weights) or his mint condition (except for some rust) 1984 Ford something or other and the time he almost got backstage at a Coldplay concert, before he had to piss ("like a racehorse," naturally.)
I pulled into the first gas station I saw and sat in the car, enjoying the respite from the stream of slightly-drunken consciousness that I'd been subjected to for the last 75-odd miles. When Tommy climbed back in, he flashed his guns at me and stuck out his tongue.
"That chick in there almost gave me my Mountain Dew for
free for a glance at these babies, but her boss was in there so she couldn't.
She wanted a mustache ride, I could tell," he said.
His nipple popped out of his makeshift muscle tee shirt and the picture was
equal parts absurd and hot. Sure, Tommy was an obnoxious good ole boy, but he
had hair in all the right places and when he slouched in his seat his cargo
shorts rode up just enough to outline his beer can size dick. I filed this info
into my spank bank for later use and pulled out of the parking lot.
Apparently, Tommy's aborted mustache ride got him going
because he could talk about nothing but all the chicks he'd banged, eaten out
or gotten head from (or totally could have if their boyfriends hadn't been
there) for the next hour. I was beginning to think he didn't realized he was
chatting with a gay guy who had little interest in cup sizes and descriptions
of vaginal scents so his question seemed to come from nowhere.
"So, what’s it like to suck a dick?
I laughed at the non-sequitur and replied, "Why, you thinking of trying it
out sometime?"
"Dude, if I thought I could get off with a guy I'd do it in a heartbeat.
Double the number of mouths I can get to suck me off? I can get down with
that."
I decided against explaining how his math was flawed and segued into seduction
mode.
"How do you know if you've never tried it?"
He raised his arms above his head and placed his hands behind it. His nipple
popped out again, as if to let me know I was on the right path.
"You tryina hop on this dick, aintcha?"
"You offering a ride?"
The look in his eyes was like none I'd seen before. Arousal was there, but so was
confusion and a little fear. I pulled into an abandoned strip mall and parked
behind the building.
"I will stop any time you ask me to, but I think you will enjoy what's
about to happen if you go with the flow."
I cupped his crotch with my hand and the firmness of what was under his shorts
let me know I wasn't about to be rejected at this point. I nuzzled the fuzz on
his chest and flicked a tongue across his still exposed nipple. With a moan, he
let out the breath he'd been holding.
When I felt his erection poking me in the stomach, I knew it was time to move
on to the main event. Not wanting to waste the horniness-and-beer-clouded lack
of rejection, I yanked his shorts down and teased his underwear-shrouded cock
head. I was right; it was thick but not real long and his Walmart special navy-blue
boxer briefs showed a big dot of precum leaking from it.
Thoughts of Andrew Christians left my head as a fat cock filled it instead.
Tommy bucked his hips and pushed it into my mouth, and I wrapped my wanting
lips around the head. I took about half of him in my mouth and then I tightened
my lips about midway down his shaft and he took in a sharp breath.
"I've never gotten head like this before!" he was finally able to
say.
I quickly said, "You've never gotten head from me before."
Returning his cock to its new home, I began to gently massage his taint while
continuing to slather his dick with my saliva. I knew he was close; I could
feel it in his balls. I pulled away; tempted to see how much further I could
take this.
"You think you could help me out? Fair is fair, after all."
That look of confusion and fear appeared on his face again before he said, "Like
how and are you trying to get fucked?”"
I told him that was on the table, but he would have to get me ready first.
"What are you talking about? I thought gay guys were always ready for a
dick in the ass?"
"First, not all gay guys even like dick in the ass. Luckily for you, I do
like dick in my ass. I also like putting my dick in an ass, but I would
understand if you were not interested in that scenario." His eyes widened.
"But, like girls, you can't just wink, and our holes are open for
business. Plus, an asshole is extra tight and needs extra persuasion to accept
that fat dick."
"Dude, you had me at 'I do like dick in the ass.' What do I have to do to
fuck you?"
"First, climb in the back seat."
I pulled off my own shorts to reveal the jock brief I had luckily decided to
wear. Don't ask me why, car rides make me horny, and I had planned to take care
of myself when we got to the beach, so I dressed slutty for myself. Don't judge
me.
Tommy was ready and raring to go and before I could guide him, he reached over
and gave me a slap on the ass. Oh yeah, this was gonna be good.
"I'm clean as a whistle down there, so either get that tongue and/or that
finger and start working me out."
I bent over, purposefully spreading my cheeks in Tommy's face in hopes he would
just dive in mouth first, in which he did. His beard felt rough on my crack but
in an effective way. His tongue was fat like his dick, and he was working my
hole like he had been doing it for years. I'm guessing eating ass and eating
pussy isn't that different.
Soon, I was the one groaning. Tommy breathing was heavy as well, I could feel
the cool air expelling onto my taint and combined with the tickle of his beard
it was almost enough to make me cum. I cried out "fuck me, dude."
I didn't have to ask twice. He opened the car door to give himself some
leverage by stepping outside the car. Grabbing me from behind he pulled me
towards himself and wrapping his hairy arms around my chest, he began to poke his
cock around my eager hole.
"Wait," I said and reached across the front seat to the glove box to
pull out a glove of the Trojan variety. I don't think that's why they call them
glove boxes, but it worked for me. I had stashed a freebie pack of lube from
some Pride event in there as well and without dislodging Tommy's arms from me I
squeezed some into my ass and handed him the condom.
Safe and still horny, he entered me. I hadn't been ridden in a while, I'd been
playing top (OK, been taking care of my own business) since that New Year's Eve
kiss with Lisa's trainer that turned out to be an all-night flip flop event
followed by a dozen unreturned texts. Bastard. But that's another story.
Right now, I'm getting reamed by a hairy, soft-bellied, camo-hat-wearing good
ole boy with a fat cock and, it turns out, a fetish for earlobe biting.
Just when I thought I couldn't take another thrust, Tommy stopped. I turned my
head with a quizzical look.
"Can I cum on your back, or do I have to do it in the rubber?" He
looked like a little boy asking daddy if he could have a piece of candy before
dinner. I'm nobody's dad so I don't like to disappoint little boys, and I
rarely disappoint horny men for that matter.
"You can cum on my face for all I care. Just not inside my ass, safety
first."
His face lit up and he rolled me over. We both began stroking, him standing
just outside the car and I lying on the car seat, legs hanging out of the car.
He shuddered and I sat up and licked the tip of his dick, sending him over the
edge. Hot cum spurt all over my cheek and ear and onto my neck.
It was the motivation I needed to cum as well, spilling my load onto the
gravel.
As I wiped the jizz from my face, Tommy leaned onto the car beside my open
door. He stared off into space for a moment and finally spoke.
"I've never fucked an ass before and no girl would ever let me do
that," he said, gesturing to my slightly sticky complexion. "I liked
it. And, if you like it too, maybe we could do it again sometime. Maybe I'll
even try sucking your dick but I'm not making any promises."
"Dude, if you wanted to try it, I'm still hard."
His eyes widened.
"I'm kidding; we still have to get to the beach with an excuse for why
we're..." I checked my phone, "holy shit, and 40 minutes behind schedule!"
Tommy grinned. "Just tell 'em we both had to drain the main vein. It's not
even a lie; because you drained me."
