Like A Virgin

There is something undeniably sexy about taking someone's virginity; for centuries, creepy old men have forged alliances and waged wars for the privilege of deflowering a young maiden. I wasn't out - or sexually active - in high school, but in my early twenties, a few opportunities to take a guy's virginity were presented to me, though I never followed through. As I have gotten older, it has become incredibly inappropriate for me to be taking anyone's virginity, unless, of course, I happen to stumble across a guy in his twenties or thirties who is still a virgin, though that opens up a completely different can of worms.

A few years ago, I started talking to a guy on Grindr. His username was Mr. Lonely; he was around my age but was an anal virgin. His profile said he was just looking to get some good head, which I knew I could provide. He explained to me that he and his wife were in the beginning stages of a divorce and that he was finally ready to explore the "gay" parts of himself; he'd never done anything with a guy, but he was incredibly curious. He'd even experimented with a dildo, finding out that he was definitely interested in trying anal sex. He was cute, with kind blue eyes, and short, sandy blond hair and a beard that only grew along his jawline.

We talked for hours. He told me how he and his wife had been together nine years but hadn't had sex for the last three. He wanted to try getting eaten out - which I wouldn't do with a stranger - as well as getting sucked and sucking. He also wanted to try fucking an ass, but that was also completely off of the table with me.

One night, our schedules happen to align. He was incredibly horny and asked if I wanted him to come suck my dick after I had dinner. As we talked, I learned that his name was Andrew, and after some deliberation I invited him over; I figured we'd just mess around, maybe exchange head, especially since I tended to be awkward around strangers, which made penetrative sex difficult. It didn't bother me too much, since I was much more oral-minded anyway. Besides, the guy was a gay virgin in every way, why not start him out gently?

When he got to my place. we went right to the bedroom and got into bed. I always had issues getting it started, since I didn't want to just get naked and start going at each other like two animals in heat; conversely, I didn't want to kiss him or be too intimate, since I had just met him and had absolutely no emotional attachment to him whatsoever. I laid in bed, staring up at the ceiling, wishing that I could just be a normal guy, take charge, and give him what he wanted. It didn't help that I'd smoked a bowl or two when I'd gotten home from work.

He suggested we take our clothes off; I grudgingly obeyed, though I hate being seen naked. I couldn't help but notice that he was slim - not muscular - with no extra weight on him, while I had fallen off the wagon with my diet and was quickly regaining the weight I'd worked so hard to lose. I wanted to hide under the blankets, but he didn't seem to mind that I wasn't a twink or as tight - body wise as he was; all he seemed to care about was that for the first time in his life, he was in a position to experiment with a guy. If I was being honest, I missed those days when everything was new and exciting and I could overcome my nervousness, desperate to experience the proverbial forbidden fruit.

He was already hard when I reached over and started stroking his dick. It was a decent size, and I couldn't help but imagine it sliding in and out of a wet vagina. Had he enjoyed it? Had he always had a curiosity about men, or was he just interested in anal and assumed - perhaps correctly - that men would be more understanding and willing to help him than a woman would? From everything he'd said, it sounded like the divorce was completely amicable, which didn't seem like a lie; he seemed very kind and sweet.

"Will you finger me?" he asked, his eyes lit with pure lust.

I should have asked him if he was cleaned out, but instead, I shrugged and said, "sure."

I moved over to the right side of the bed and positioned myself between his legs. He spread them apart, revealing his tiny, pink hole. There wasn't any hair down there, which made me wonder if he shaved or if he just was incapable of growing hair there. Regardless, I grabbed the lube from the end table and squirted some into the palm of my hand. As I spread it around my fingers, I noticed that he was looking down at me, absolutely no nervousness visible on his face; I wished that I could be like that.

The first finger went in after some slight resistance. I moved slowly, careful not to force it; I didn't want to scratch him or go too deeply too soon. As my finger was enveloped by his warmth, I felt him stretch to accommodate me. I kept my eyes glued to his face, looking for any sign or pain or discomfort; instead, he was chewing his lip, his brow knit.

"Ready for another finger?" I asked, slowly moving my finger deeper inside of him, grazing his prostate.

"Mmmm, yeah," he moaned, his eyes closed in ecstasy.

The second finger seemed to be swallowed into him. With two fingers inside him, Andrew was moaning louder, moving his hips a little to match the rhythm of my fingers. He definitely wanted it, which really turned me on; even though he wasn't touching me, when I glanced down, I noticed that I was rock hard.

As I continued to spread him open with two - and eventually three - fingers, I started to warm to the idea of putting more in him.

"I want you to fuck me," he panted, his face screwed up in - pain? pleasure?

Without thinking too much about it, I pulled him down a little so that I was perched over him. I lubed up my dick, sure that it would just go to waste, but was surprised when it made contact with his hole and slid in. I'd never done missionary before, only doggy and cowgirl, but I'd always wanted to try. It was true that I wanted to do missionary because it was more intimate - I could kiss my partner and watch his face as I fucked him - but even though Andrew was a relative stranger, it felt right. I wanted to make sure that he had the amazing first time that I would hopefully have - if and when I let a guy inside of me.

He felt warm and tight on my dick, easing my nerves. I could still hear the voices of my loved ones in my head - telling me that I should be wearing a condom, that I had more to worry about than just HIV/AIDS and shit dick, but I knew that condoms instantly killed my erections. The only way this was going to work was if I barebacked him. He hadn't been with anyone sexually in three years, I told myself that if I had something, he'd know by now; there was always the possibility that he was lying, but I didn't allow myself to even consider that option.

I lost myself in the moment, chewing my lip as I fucked him gently. I was spurred on by his moans, and as I picked up the pace, going deeper and more intensely, I saw that his lips tugged up into a smile; I had never heard of someone laying there, smiling during sex. Any doubts I had that I wasn't experienced or couldn't perform adequately evaporated. I locked onto that smile, fucking him harder and faster, making the smile widen.

Eventually, I felt myself getting close. I wanted to cum inside of him, but I wasn't sure if that was allowed. The few times that bisexual Tyler had let me fuck him, he'd always told me not to cum in him, to pull out and cum on his hole instead.

"I'm getting close," I muttered, going harder and faster still.

"Mmm, cum in me!" Andrew cried, still smiling despite the fact that his mouth was open.

All thoughts ceased as I felt myself exploding inside of him. I'd never cum in a guy before - not without a condom. I could see why everyone said that raw was so much better. Holy fuck! I had just had unprotected sex and it felt amazing!

I pulled out of Andrew and went to grab a towel to wipe myself off with. When I came back, he was still laying there smiling, basking in the afterglow. Even though I knew that I'd probably never see him again, it filled me with warmth to know that I had given him a great first time.

"How was it?" I asked, sliding into the left side of the bed and pulling my clothes back on.

"Amazing!" he said, laughing. "So much better than a dildo."

"Glad I could be of service," I joked, laughing. "Want me to..." I gestured toward his dick; he had not cum.

"No, no, I'm good." He laughed. "Fuck that was good."

"Good."

I wanted to suggest that he get up and go to the bathroom to relieve himself of my seed, but I figured that that would be entering uncomfortable territory - for both of us.

"Oh, shit," he said, chuckling again. "Some of it slipped out."

I looked over to see that a pool of jizz had leaked out of his ass onto the clean sheets. I was a little annoyed - I'd just put fresh sheets on - but I knew that after having sex, I would have to change them anyway. Still, didn't he know how to tighten his sphincter enough to keep that shit in?

As he sat up to start putting his clothes on, I saw his back for the first time. On the back of his left shoulder was a giant skin tag that resembled a cartoon chicken wing; I instantly cringed, grateful I hadn't seen that before we'd had sex. If I had seen that, I would have definitely lost my hard on and wouldn't have gotten to experience the joys of breeding a hole.

Andrew got dressed and then said that he needed to head out; I wasn't offended. Had we had a connection, I'd have gladly laid there and cuddled him, basking in bliss, but the reality was that we were relative strangers and we'd both gotten what we wanted from the situation; what else was there?

I walked him out. Even though he said that he would keep in touch and that he wanted to see each other again, I knew that chances were slim that we'd ever actually do it. When I was younger it really used to bother me, I'd feel used and worthless post-orgasm, but now, I felt numb to it; I'd been around too long to be the sweet, caring guy I'd been when I started my gay journey. I'd had to learn how to emotionally detach and just enjoy the fun when it came to me. I didn't have to have a lifelong relationship with every person I shared a bed with; not everyone was a life changer.

It's been a few years now. I messaged Andrew one time after that night, trying to get him to come over again, but I never heard back. I never saw him online again after that night, but his account still exists, so I know that he didn't block me. I wonder if he had lied to me about his wife, if it had just been something he'd wanted to try, or if they had decided to make things work out after all. If memory serves, he did tell me that they had a kid or two together. At the end of the day, it doesn't really matter; if it was meant to be a recurring thing - or anything else - it would have happened. I don't regret it, though. I've been a lot more confident - in the bedroom - since then. I know it's not smart to have unprotected sex, but knowing that condoms make me go soft, I don't really have a choice; thankfully, I don't make a habit of having sex with random guys, so at least in that regard, I'm safe.