I’ll always remember my first time hooking up with a straight guy. We went to high school together, and did musical theater and had the same group of friends for about seven years. He was cute and quiet, always the sober one of the group (particularly when we would get back together after most of us left for college), and was probably regarded as having the best butt in the friend group as well (between all the guys and girls).
While a year younger than me, he always had a pretty great body, and was in general an attractive soul.
He and I always had an interesting relationship. I was the only gay person in the group, and was the go-to for their questions about anything anal related. I ended up coaching a couple through their first anal sex session, actually. This friend (let’s call him Alex) always had a few odd questions for me, the ones that were sent at two in the morning over snapchat.
“What does it feel like getting rimmed?”
“How would you suggest I finger myself?”
“Does anal hurt?”
Just normal, “straight guy” questions.
The night in question happened over Christmas break during my sophomore year of college; it was six weeks long, but I was only back for a couple. A group of us got together one night for our usual festivities (4/20, drinking, playing card games, and hanging out).
As the night was going to a close, the sober ones began driving everyone else home. Alex came over and asked me if instead of heading back to my place, if I would rather spend the night at his house.
Having never been there, I accepted, and offered to bring a bit of rum I had been saving throughout the night. Alex smiled and said he’d drive a couple people home then be back.
Twenty minutes later, the two of us were breaking into the rum, both lounging on his pull-out couch and watching Bob’s Burgers. Again, Alex was always quiet, and conversations between us were simultaneously soft and poignant. He had a sweet naivety about him, bred from the small town of Michigan we call home. But the rum and good jokes helped fuel conversation, and he and I were having a great time.
Every couple of minutes, a hand of his would find itself on my leg.
About a quarter of the way through the bottle, Alex stood up and called my name.
“Can you look at this and tell me what you think?”
I watched as Alex unbuttoned his jeans and pulled down the top of his briefs, showing a well-trimmed bush.
“I did it this morning,” he said, looking at me for my approval. I had been fantasizing about seeing his dick for years, and here he was, asking me what I thought of his pubes.
“I think it looks-” I started, but before I could finish, he had taken my hand and was rubbing it over the neat area. Looking up at him from down on the couch, I kept eye contact as I moved my thumb lower, through the hem of his briefs, and started rubbing it against his noticeably growing erection. Alex just smiled, but lifted my hand before mouthing “later.”
He sat back down on the couch with me, but before he did, he slipped off his shirt, revealing a toned body I was envious of. This time, he wasn’t as subtle with his desires. His hands were always on my legs, rubbing them. Mine were on his abs, feeling them, every once in awhile letting my fingers slip and rub him, enjoying watching a look of ecstasy go over his face.
After another hour or so, and more rum, Alex asked the question: “Could you give me a massage?”
“Of course,” I responded, then paused. “But you’re going to need to take off your pants.”
Slowly, and reveling in every second of it, he complied.
I started at his shoulders, enjoying feeling his tense muscles and warm skin beneath my fingers. A part of me had been wanting this for years, and I savored every moment with him beneath me. I would press my body against his, making no effort to hide my obvious erection; rubbing it against his boxers would elicit slow, sensuous movements from. Eventually, I made my way down to his hips. I made one final run from his shoulders again, kissing his back on the way down. I perched on my knees and placed my hands on his firm, round ass.
“May I continue?” I asked.
“Please.” His voice was a little more than a moan.
Fingers trembling, I pulled down his briefs His ass was perfect, a little hairy, and splendidly round and muscular. My hands explored every inch of it, with my mouth following shortly after. Occasionally, I would let a few fingers wander, brushing over his most sensitive areas. I loved hearing him moan. Nothing, though, would prepare me for the sheer delight (his words) I brought him when I started rimming him.
It was clearly his first time doing something like this. But god did he love it. As my tongue slowly moved around him, eventually entering him, his body contorted in the most stunning of ways. His hands moved to spread himself even more open for me.
As I devoured him, I slowly moved a hand up, and slipped a finger in. I loved feeling him tense up, then relax as he let me explore him. A minute later, and he took in a second one, and finally third.
“I’m ready…” he whispered, and placing my hand on his back, I entered him.
For his first time bottoming, he was fantastic. He managed his breathing perfectly, and he had no problem taking all of me (I’m pretty thick). I loved feeling him take me, knowing I was the first he had let in. After a few minutes of pounding him while he was on his stomach, I flipped him over.
“I want to see your face.”
Alex’s body was sweaty and glistening, and I had never seen him look so vulnerable. An undeniable look of desire was in his face, and he inched his ass closer to take me again. He lifted his legs and placed them on my shoulders. As I entered him again, I loved seeing his eyes roll back into his head. I placed one hand on his chest and wrapped another around his dick, and began giving his ass the treatment it deserved.
Alex was known in the group for having the least experience, but he was a champion. The way he tightened around me as his load emptied out onto his chest, saying my name as he came was one of the hottest things I’ve ever seen. When I pulled out and came on his chest too, we both looked up at each other, locking eyes and enjoying every moment of what had just occurred.
Almost every time I return to Michigan, Alex and I will meet up for another one of our sessions. He hasn’t opened up to anyone else in the group about his questioning sexuality, but the two of us enjoy our rendezvous. We share an intimate connection now, one that is always worth exploring when the opportunity arrives.