Losing My Virginity

When I was younger, I wanted my first sexual experience to be for love, not simply a buildup of teenaged hormones. Unfortunately, my stepdad was incredibly homophobic, going so far as to tell my mother when he caught me watching the musical film Chicago at age twelve that if I came home with a boyfriend, he was going to kick me out. When my mother passed it on it didn't even occur to me to be upset with her for not only telling me about it, but for not punching him in the face like he deserved. Growing up knowing that the way I was was wrong, I learned to deny it as much as humanly possible; I didn't feel that I could trust anyone with my deepest, darkest secret. In high school, there was a lot of speculation about my sexuality - I was the guy who hung out almost exclusively with girls and loved musical theater and Madonna - but I didn't feel that I could be open and honest about my sexuality even then, so instead, I fervently denied it. I kept all of my gay crushes hidden away, afraid to even act on them lest my stepdad find out and kick me to the curb.

There was a period - the year after I graduated - when I could have done a lot of experimenting if I'd had the wherewithal and had known about Grindr. My stepdad took a job in Fort Wayne, Indiana, and my mom worked overnight stock at Kohl's; it was just my autistic brother and I at home most nights. If I'd been more aware of the world around me, I could have been on Grindr getting comfortable with talking to guys and being open about my true proclivities.

The year that I moved in with my grandma, I never got to have the house to myself; my uncle also lived with us, along with his drugged-up kleptomaniac girlfriend and their four-year-old son. I was the only person in the house who worked - Grandma was retired by then - so even when my grandma would go on trips to Colorado to visit my aunt and uncle, I didn't have an opportunity to explore my sexuality.

Right around the time of my twenty-first birthday, my uncle got kicked out; it was just my grandmother and me. Later that month, she went on a weekend trip to UP with her friend; I had met a guy named Ray online, but hadn't gotten around to meeting him in person. I ended up inviting him over, but he knew I was inexperienced and nervous as hell; he gave me head and I jerked him off. I was embarrassed at my lack of experience and general nervousness.

I developed crushes over the years, but unfortunately for me, the majority of them were on straight guys, or at least, guys who were bisexual but were too afraid to act on it. I still wanted to save my virginity for someone special; I wanted it to matter. As the years went by, I continued to meet up with guys once or twice a year to get head.

Pre-Grindr, I found a gay online dating site called Manhunt. It wasn't as sophisticated as Grindr, nor was there an app for it; it was an old-fashioned computer site. I was uncomfortable with the amount of creepy older men who hit on me and sent me nudes, but I figured that it was all part of the process. I had to get comfortable enough to exchange nudes and learn how to flirt with a guy, how to turn someone down without being mean. After a bit of trial and error, I found a man who lived in the same town as me; he was about ten years older than I, and honestly, not bad looking. He wasn't drop dead gorgeous or anything, but I definitely could have done worse. His name was Noel; we exchanged nudes and numbers; when I confessed to him that I was a virgin, he offered to help me out. He was verse, meaning he could top or bottom; he wanted to top me, but was also down for me to top him, which was more along the lines of what I was looking for. He was open to the idea of dating, but I wasn't sure that I wanted to actually date him; I'd gotten over my older guy fetish when I was twenty-two. That year for Thanksgiving my grandma flew out to Colorado; Noel and I made plans for him to come over on Thanksgiving and take my virginity. I wasn't entirely into it because while he seemed like a nice guy and everything, I didn't love him; I didn't want to kiss him or cuddle with him. I just liked the thrill of the idea of it all. The night before the deed was supposed to take place, I tried an edible - br0wnie - for the first time and got so high that I slept until early evening. Noel had said that he wouldn't be free until after he'd done his family dinner, so I didn't feel bad about sleeping half of the day away. As the evening turned into night and I received no word from him I couldn't help but feel relieved.

Noel and I talked occassionally throughout the following years; I never got an explanation as to why he blew me off, but it didn't really matter. Noel ended up taking on one of my annoyingly obsessed online dating stalkers for me; the kid was not attractive, but really wanted to me to take his virginity. Thankfully, Noel didn't mind that he was chunky and rather homely looking; Noel took his anal virginity and I never heard from him again. I learned that Noel and I had friends in common, too; he and Ray had hooked up quite a few times when they were younger, also, Noel was best friends with the mother of the cute straight guy I was crushing on at work at the time.

By the time I turned twenty-five I was over it. I had patiently waited for love to find me, but it was not happening, no matter what I did. I didn't want to be a virgin anymore, it was embarrassing enough that my friends all knew that I still hadn't had sex; some said that I was being too picky, or that I needed to forget about love and just focus on sex. The truth was, I wasn't sure that I could sleep with someone I didn't love; for all my jokes and pretend sluttiness, at my core I am very much someone who wants meaningful sex. I worried that if I didn't lose my virginity soon - by any means necessary - I'd be a thirty-year-old virgin; that did not sit well with me at all.

Noel and I had started talking again; he mentioned that he had been single for awhile and was looking for a hookup to satiate his needs. By then, we'd been talking on and off for about three years and I really wanted to have sex, if for no other reason than to not only prove that I could, but also to feel like a normal human being for once. The more we flirted the more I started to warm to the idea; there was almost no chance of me falling in love with Noel; it could be quick in and out job that would help me a out a lot. He was an experienced bottom; any questions or concerns I had would be taken care of. Sure, he'd put on weight since we'd first started talking in my early-twenties but so had I; I couldn't judge him for his lack of hair, either.

The day of Devil's Night in 2015, I drove to work early, telling my grandma that I had to go in early to prep. I wanted to have enough time to be able to relax and enjoy the experience without worrying about being late for work. I parked in my normal spot and a few minutes later, Noel pulled up next to me, holding a lit cigarette. I was incredibly nervous, but I swallowed the butterflies and got into his car. He drove the two blocks to his house and then we went in. I wasn't sure if I should just get naked right away or not, but Noel took charge, leaning in to kiss me before leading me into his bedroom. I stood awkwardly in the doorway as he stripped naked and got into the bed. "I'm gonna put some porn on," he declared, not even looking at me.

"Okay." I slid out of my work clothes and climbed onto the bed, trying to ignore my heart thundering in my chest.

"What kind of porn do you like?" he asked, his eyes scanning the myriad of porn options available on the screen.

"Um, I don't know," I confessed, "I don't really watch porn that much. It makes me feel insecure."

"Why?" He turned to looked at me quizzically. I watched as his eyes roamed over my naked body; I was so self-conscious that I wished that I could turn invisible.

"It makes me feel bad about myself."

"Why"

"Because I'm not hot like the guys in the videos," I explained, feeling my cheeks warm as heat rose and turned them red. "I can't do the things they do. I can't do it all as well as they can."

"It's not about being as hot as them or being able to do what they can do," he said, his voice gentle and soothing, "it's about the fantasty. It's about knowing what turns you on, getting ideas for new things to try."

"I still haven't really done anything other than hand jobs and blowjobs," I confessed. "I've given, like, one blow job."

"Want to give another one?" he asked, quirking a suggestive eyebrow.

I didn't really want to, but I knew that it would help get things going, so I scooted down on the bed and took his erect cock into my mouth. As I sucked him slowly, I hear him moan over the sounds of the moans from the porn. "You're really good at that," he gasped, grinning ecstatically.

After a couple of minutes, he sucked me. He had bragged before about how good his head game was, that he could make my toes curl; in the moment, it wasn't terrible, but it certainly wasn't the best head that I'd ever gotten.

"Can I finger you?" I asked, curious what that would feel like.

"Mmmmm, of course," he purred, rolling onto his stomach and arching his back so that his ass was jutted out in front of me. I squirted some lube on my right index finger and pressed against his hole. At first there was resistance, but before I knew it my finger was being sucked into his warm ass. I moved it slowly, smiling as I touched his prostrate and he moaned. After a few moments I added another digit. Fingering him was turning me on, but not quite enough to distill my anxiety completely.

Noel rolled onto his back and put his legs up on my shoulders as I slipped three fingers into his ass. "Oh, fuck," he gasped, his eyes closed in ecstasy. I glanced down to watch what I was doing and noticed that blood was dripping out of his ass onto the white comforter than he was laying on. I tried to stop, pull my fingers out, but he clenched his sphincter around my fingers, holding me firmly inside of him. I wanted to ask if he was okay, but he kept moaning and writhing with pleasure, so I assumed it was normal. Why hadn't anyone told me about this? I was even more turned off and confused when I saw beads of sweat start to form on his forehead and then trickle down his face. Who sweats from getting fingered!?

"I want you to fuck me," he moaned after a while, gazing up at me through lust-laden eyes. "I know you're a virgin, so you don't have to wear a condom. I'm all cleaned out."

"I probably should anyway," I replied, casting a quick glance down at the blood. I could smell the tang of iron in the air; it was making my boner soften a little. "I don't want to cum too quickly."

"Mmmm, the quicker you cum the first time, the longer you last the second time." He rolled over and grabbed a condom from the nightstand. Did he really think that we would be having sex more than once today? As I slid the condom on, he lubed up his hole and looked at me. "How do you want to do it?" he asked.

"I don't know..."

"Let me try riding it."

He climbed on top of me and reached behind himself to grab my cock. He held it steady as he slowly sat himself on it. After a slight struggle, it went in. All I felt was warmth as he started to move his hips. Is this it? I silently wondered, is this sex? Seriously? People ruin their lives over this shit?

I must have started to go soft because Noel quickly climbed off of me. "It's not hard enough," he said, which kicked my embarrassment up another ten notches.

"It's not?" I asked lamely. I glanced down; my dick was about as hard as it was when I jerked off.

"You don't want it to be able to bend so much." He reached down and demonstrated that it wasn't fully erect. "It's okay, though, I know you're nervous and it's your first time. It's normal."

"Is it?" I asked, once again wishing that I could just turn invisible and vanish, never to be seen again.

"Yeah, we've just gotta get you to relax." He took my cock in his hand and started jerking it. "Tell me about what turns you on."

"This," I replied, biting my lip. "I just always pictured doing this with someone I liked - no offense."

"None taken." He smiled as he continued jerking my cock.

"I like Zach," I admitted, closing my eyes. I knew that it was stupid of me to have developed another crush on a straight guy, but I couldn't help myself. Although Zach didn't work with me anymore, we kept in regular contact. He was really cute - at least in my opinion - with dark brown eyes and hair, a short, slim build, tattoos on his arms, and a smile that made me melt. He had been very nice to me when he hired in and we'd quickly become friends, so close that his girlfriend at the time had often joked that she thought he was in love with me and that if I wanted him, I could have him.

"He is super cute," Noel agreed. "Do you think you could get him to play with us?"

"I don't know. I don't think he's even gay..."

"I heard that he lost his virginity to a guy."

"What?" I almost sat up in shock. Zach had lost his virginity to a guy but wouldn't make a solid move on me!?

"That's what I heard from Richard Craven."

I didn't know Richard Craven well, but I knew enough to take what he said with a grain of salt. Besides, he had raped his younger cousin when they were kids, hated women, and even as adult, insisted on being called 'Richie.'

"I didn't know that." I hated to admit it, but jealousy started to burn in my gut. Why couldn't Zach have lost his virginity to me? I bet if he had he wouldn't be straight now.

"If you could, I'd be so down. Let him know that I'd keep it between us."

"I really want to suck his dick. I bet it's nice," I murmured, picturing his perfect dick.

"Oh, yeah, definitely. Skinny guys always have big dicks," Noel agreed.

"We've talked about him coming over to hang out with me. I secretly wonder if he'd consider letting me suck him."

"You should ask him. You'd look so hot with his cock in your mouth."

The talk of Zach must have done the trick, because Noel grinned at me and said, "there, I think you're ready again."

I looked down and saw that I was in fact rock hard. He got on all fours as I lined myself up behind him and lubed up my cock a little bit more. I leaned in, staring at the back of his head as my cock eased into his hole.

Immediately - despite the condom - I knew what all the fuss was about. It was like my cock was being gripped by something warm and tight - not at all threatening. This is what it's all about! Oh, my God!!! As I moved inside of him, I forgot all about my nerves, the blood, the iron-y tang in the air; I even forgot about my boss's advice to think about anything but what I was doing so that I wouldn't cum too fast.

"Oh, fuck, yeah," Noel moaned, his headboard creaking rhythmically into the wall. "Pound me!"

I had been trying to go slowly, to pace myself, but if he wanted to be pounded then, I guess I would oblige him. After all, as he'd said the before, the sooner I came the first time, the longer I'd last the second time. Did I have it in me to go two consecutive rounds my first time out on the field? We had given ourselves an hour to do this so that I wouldn't be late to work; I still had to get him off as well.

I started to pound him deeper and faster, spurred on by his moans and cries of ecstasy. A small part of my mind that wasn't totally focused on the feeling of pleasure gripping my dick wondered if there was going to be a dent in the wall from how furiously the headboard was now slamming into it.

When I finally came it was like no orgasm I had ever had before. Normally, I'm pretty quiet, but it felt so amazing that I couldn't resist a gasp and an audible groan. As soon as I'd pumped my seed into the condom in his ass, I collapsed onto the bed like a ragdoll. My heart was pounding - in a good way for once - and I felt relaxed in a way that I hadn't since I was still living at home with little to no responsibility.

Noel grinned at me. "How did it feel?" he asked, peeling the condom off of my dick.

"Good!" I gasped, laughing. "How was it for you?"

"Really good," he replied. "You lasted quite a while too. Next time you'll be able to last even longer."

"Was I really good? You can be honest," I insisted. I didn't want him to sugarcoat it or tell me I was good to spare my feelings; I felt like I was in school again and was getting critiqued on one of my art projects.

"Honestly," he assured me with an amused chuckle, "you were really good. You did better than I thought you would."

I beamed, so aglow in my rave review that I failed to notice that Noel wasn't throwing the used condom away until I saw him tip it so that my thick load drizzled out onto his hard cock. Oh, wait is he gonna....? Oh fuck! I found myself getting aroused again as he used my cum as lube to start jerking himself off.

I propped my head up on my hand and watched for a few minutes before I offered to finger him again. By that point, the blood was completely irrelevant to me. I happily slid three fingers into him again while he worked his cock.

We were both having a good time - too good in fact. When Noel took a break because he was having trouble cumming, we realized that I had about twenty minutes before I had to be at work. We hurried down the hall to his bathroom, where I furiously washed my hands while he squatted in the tub and used his hands to dump warm water on himself.

"My shower is broken," he explained, catching me watching me curiously. "I shower at my friend Tonya's house, but the bath part still works."

"I miss baths," I confessed. In the house I'd grown up in, I'd had my own bathroom upstairs; about once a month or so I'd run a hot bath and relax into it while I read a book. The bathroom at my grandma's house only had a shower.

I rinsed off my dick and stomach and then washed my hands again before padding back into his bedroom to get dressed again.

As we were driving back to my car, Noel lit up a cigarette. "I thought you quit," I said, secretly wishing that I could have one. I'd quit - for the second or third time - by then and was trying to stay strong,

"I quit a lot," he admitted, blowing smoke out the window. "It's a hard habit to break. I keep some in my freezer for emergencies."

"I know how hard it is," I agreed. "I've quit a few times now. I'm usually good until I'm around someone who's smoking."

"Do you want one?" he asked, holding one out to me.

I should have said - wanted to be strong enough to say - no, but I felt like losing my virginity was a big enough event that celebrating with a cigarette wouldn't kill me. And besides, if I was bumming one from Noel, I wasn't going to get addicted again because it was just one, not a whole pack.

He dropped me off and headed back home, leaving me to beam in the parking lot, smoking my cigarette and feeling like the greatest thing in the entire world had just happened to me.

Looking back on the whole endeavor I feel rather indifferent. Part of me is disappointed in myself that I didn't save my virginity for someone I had feelings for, someone special, but the more logical part of my brain knows that had I not bitten the bullet so to speak, I'd still be a virgin today, at thirty-five. I've still never had an actual relationship; even being sexually active since I was twenty-five, I've only had sex eight more times with four other guys, two of those being with Noel. The only thing worse than being thirty-year-old virgin is being a forty-year-old virgin.

I do wish I'd saved my virginity for someone closer to my age, someone I was more attracted to, but the dichotomy there is that as much as I am not attracted to Noel, I have had the best sex with him all three times we've met up. Maybe it's because I'm not attracted to him and there's no pressure to date, so I'm more relaxed and uninhibited, or maybe because he was my first, but when I get inside of him - as long as I don't look at his face - it's like Wonderland.

I remain hopeful that someday I will find a guy that steals my heart so that I can have the whole package - the love and devotion I crave on top of great sex. If I could just get over my fear of rejection, of being other than I could go out into the real world and have normal, healthy interactions and relationships. In fourteen years on Grindr, I've had barely any luck, especially in the dating department. As I've gotten older, I've come to realize that I don't even necessarily have to be in love with the guy to have good sex with him, I just have to comfortable enough with him that I can let myself go and get out of my head; I am my own worst enemy.

If I could travel back in time to my younger self, I would tell him to stop worrying if people found out and cared that he was gay; I'd tell him to try for a relationship in high school, to take advantage of being awkward and unsure at a time when everyone is awwkard and unsure. I'd tell him to download an app called Grindr and take advantage of those nights after he'd put his brother to bed and had an entire house - a nice house at that - to himself. But most of all I'd tell him that the best thing he could ever do - will ever d0 - is to be himself, no matter the consquences. Life is too short to live in fear of being your authentic self; you owe to it the world and yourself to let your light shine as brightly as it can, like beacon guiding you home.