I can’t believe this is happening.
So I’m going to write this story as it happens because it’s happening to me RIGHT NOW and I’m freaking the fuck out and it’s helping me to pretend I’m busy on my phone because holy mother fucking holy shit balls.
I’m on a cross-County road trip with my 22-year-old college girlfriend Kelly, and her family. We’re traveling in their three row Honda Pilot as we transport some of the family’s artwork to a fairly well known gallery in Chicago where my girlfriend’s dad is having some of his work featured this upcoming weekend. Currently, I’m sitting in the very back row next to him. I had started the trip next to my girlfriend but after two driving legs, it was her turn to drive and her mom was already asleep in the front passenger seat, so her dad just climbed back with me to make things easier.
When he’d first gotten into the backseat with me, we’d both realized the issue, the back bench seat wasn’t that long and both of us wanted to stretch our legs out and get some shuteye.
We both had the various pillows and blankets that been brought along for the long drive east, and soon we seemed to figure out something that worked, even if it was a tad awkward.
As my girlfriend changed the Bluetooth over to her list of favorite music and the car pulled onto the freeway, her dad whispered that he had an idea.
He moved his pillow up against the side panel and window and sat facing me. He had me do the same. Then he moved his left leg under my right leg (he was on the left side so this was his outside leg), and his right leg under my left. We both figured out the logistics and he scooted down more into a laying position with me doing the same.
It was way comfier this way for sure, and we both seemed to be able to lay down now with just our heads propped up against the pillows by the seats. Although I also realized that we were basically scissoring each other as our crotches naturally pressed together from the pressure of our intertwined legs.
I almost giggled when I realized that I could actually feel my girlfriend’s dad’s bulge of a cock pressing up against my thigh. We were both wearing comfy sweats for the drive and it was unmistakably a squishy cock tucked up against the inner half of my thigh—even through both of our sweatpants I could feel it. I had also taken a large hit off my weed pen at the last rest stop and my stoned brain couldn’t help but be kind of humored by this strange predicament.
I almost decided to change positions, but it would’ve just made this all even more awkward so I tried to just fall asleep. We were both very comfy so there should be no reason why I couldn’t just ignore it.
But I couldn’t fall asleep, because I was literally pressed up against another guys cock for the first time in my life and it was absolutely crazy. He must’ve thought nothing of it because he fell right asleep wedged tight against me.
And after a long while of strangely nervous energy, I was literally almost asleep too, and then I felt it.
His cock felt harder. It was growing—getting bigger against me. It was pushing firmer into my inner thigh and balls as we lay pretzeled on that backseat. He was getting really hard in his sleep. His cock felt big, even through the pants. He must’ve been having a really great sex dream. Ugh
I took out my phone just now to try and distract myself. What am I supposed to do, wake up my girlfriend’s dad and tell him that he’s pressing into me with his boner? Fuck that!
The backseat was completely blocked by the large paintings they were transporting in the middle row so I was thankful for that at least. But there was something else weird happening. I was getting hard as I lay like this. I think I had gotten way too stoned or something. I was horny high.
The sudden firmness of his crotch pushed against me like that was feeling really good for some reason.
I had never done anything sexual with another dude, but I was getting hard from my girlfriend’s dad’s boner.
What in the crazy fuck?!
Then he surprised me. I felt him bring his hands downs and place them on my upper leg and his leg.
His large hand lightly held my upper thigh muscle. And I was suddenly very aware of how close his thumb was to the boner that inflated like a pipe down the inner theme of that very same leg.
I glanced past my phone screen and I could see that his eyes were open, looking at me. I swear I could feel him flex his legs against mine. And then I couldn’t believe it, but I flexed my legs back against his.
When I did that, he began to rub my thigh with his hand.
And that’s where we currently are. You’re all caught up now, and I’ve been rapidly typing this all out to pretend as if it’s just happening completely without my knowledge, even though I’m breathing very deeply and even though his thumb just rubbed against the outline of my cock for the first time and I think he’s actually doing this on purpose, holy fuck. Fuck. Fuck. Fuck.
Fuck. I’m so horny and I’m so nervous, but fuck, it feels really good. He’s bringing his hand fully over my cock and I love the way his hand feels fondling me like this.
FUCK, WHAT AM I DOING?!
I gasped a little cuz he just grabbed my shaft through my thin soccer sweats a second ago.
My girlfriend just turned the window defogger on in the pitch-black car which I feel says just about everything about how heavy we’re breathing. Maroon 5’s ‘Secret’ is ironically playing from the nearby speakers. My girlfriend loves that song. And now her Dad is fucking touching my hard-on through my sweatpants, so, ya know, holy fucking-fuck.
I’m still just typing away on my phone telling this story in real time because I’m so fucking nervous and I can’t believe this is happening right now. What is happening right now? My girlfriend’s fairly attractive father is rubbing my penis through my sweats, and he is starting to grind against me now with his own crotch and I can feel that too.
I’m holding my phone with both hands now, trying to contain my excitement, or continue whatever this game is. I’m covering his face with my screen so I don’t freak out.
He’s pulling his inner leg back now and he’s, oh wow, he’s pushing that one under me too. I’m sort of laying over the top of his lap now and I can feel what he’s doing. He bends my legs up carefully and quietly and pulls my sweats off my body. The cool air feels dangerous on my skin. Then he crumpled them onto the floor. Now he’s pulling his sweats off below us. I lift my ass up to give him room.
I’m still life like that when I feel him pulling my boxers off and now I realize he wants my lower half completely naked. I’m not stopping him.
He’s pulling his own boxers off and then sitting me back down and now the bottom of my balls immediately come into contact with his hard shaft.
He licks his fingers and brings them down and I feel both of his hands take hold of my very hard cock. I catch my breath as he begins to slowly jack me off in the dark like this with both of his hands.
I’m so fucking horny. My precum is lathering up my cock as he jacks me off and I’m still typing away on my phone to keep myself calm, as if I’m not currently getting a really sexy hand-job.
But I’m not calm. I can feel him pressing his cock against me and it’s turning me on.
He feels big. I feel him wedge himself further under me as he pulls my cock closer to him. His shaft is pressing up against my ass now. His length runs up against the sensitive skin of my buns and crack and I shudder.
Fuck. I didn’t expect anything like this. I can feel the head of his cock lodging closely toward my very virgin anus and I think I might want him to fuck me.
Yeah. Fuck. I do.
I look up from my phone screen at him now and make eye contact. He is pushing forward and making the head of his dick press against my hole. I can feel the perfect curve of his helmet head rubbing my very sensitive ring now.
I have never wanted to do anything sexual with a guy in my life before, and here I am with my girlfriend’s dad rubbing his very gorgeous cock right up against my sweaty butthole and I want him to put his cock inside of me.
Fuck. I want him to fuck me. I need him to fuck me.
I can’t focus on typing anymore. I need to put my phone down, oh fuck, he’s spitting on his fingers. I’ll finish this later. FUCK!!
Two hours later:
Here’s how it ended, holy shit. I mean, legitimately, this actually happened, holy wow.
Okay, so. . .
He made his cock super wet and slippery with his own spit as the car continued along on the mostly empty early-morning highway. He was absolutely locked into my face now, smiling at me in a devilish way as he rubbed himself against my spreading tightness.
I’d put my phone under the pillow and was now staring my girlfriend’s dad in the face. He had a very naughty look—the invitation was clear.
Did I want him to fuck me? He leaned downed and grabbed the base of his cock like an arcade joystick. He rubbed the head of his spit-covered bar up and down my sensitive butt, spreading the juicy saliva and pre-cum around as his helmet would get caught on my hole and bend over my opening, glazing me more and more each time with preparatory lubricant.
He centered his aim closer now and I felt him push his head inside of me, but only just the very tip. It hurt, but he had gotten me so fucking wet and so fucking horny that I actually kind of liked it. The weed was probably helping. Holy fuck, I really liked this. I was going to be fucked. I was thrilled. I still could barely breath. It was my first time with another guy. I was going to let him do this.
He nodded his head slowly twice as if to ask me, and I told him yes with one nod back. I gripped his legs below me with both hands to steady myself as he pushed further into me.
The only audible moment of the entire sexual encounter came out of my mouth the second that his lollipop-sized helmet finally pushed past the last remaining straight-guy resistances of my Holy Fire-Pain sphincter.
I moaned and my girlfriend whispered back over the mid-row paintings barrier to see if I was okay.