Losing My Virginity - Again

Even though I had always assumed - especially in my days as a baby gay - that I was a bottom, as I got older and gained more sexual experience, I realized that I liked the idea of topping. Not only does bottoming require meticulous preparation - if you want a clean, pleasant experience - but it also looks and sounds incredibly painful. With my long history of stomach issues, any kind of sensation involving my back door immediately makes me think of my mad stomach attacks - not something I want to think about during sex. I was fine not ever experiencing the alleged wonders of receiving anal sex, but recently, that changed and I'm still not sure how I feel about it.

Several guys have tried to top me - one even offering me $20 to let him - but I was never very receptive to the idea. Santiago talked me into letting him try one night, and when he wasn't able to get it in, I was extremely grateful. Having a straight guy with little to no gay experience take my anal virginity sounded like a recipe for disaster. Even when I was having sex with experienced bottoms, I made sure to slowly enter them and hold still, allowing their body time to get used to my dick; I feared that Santiago would just go all in and cause me immense pain.

While Zane had primarily been a bottom, he still had a desire to top me. Given how thick his appendage was - thick enough to hurt my jaw rather quickly when I blew him - I could only imagine how painful being penetrated by him would be. He assured me that anal sex didn't have to hurt, especially if it was done patiently and correctly, but even the idea of taking that girth made me clam up in fear. I allowed Zane to finger me - the first guy ever to do that - and found it to be a rather unpleasant experience. Even when it was supposed to feel good - when my prostate was being stimulated - I had the uncomfortable sensation I got if I masturbated without peeing first. I wanted to try for Zane, but the last thing I wanted was to halt the process once it had started and have to live with the shame and disappointment.

A couple of weeks ago, my DL bi/straight guy friend Tyler - the one who lived downstate with his girlfriend and baby - got ahold of me. He was up my way working and was wondering if I wanted him to stop by on his way through. I had told myself that continuing my no-strings attached situationship with him was wrong and had to stop, after all, his girlfriend presumably had no idea that he was bi, let alone cheating on her, but amidst a dry spell, the idea of Tyler getting me off was too good to pass up. I'm not sure why, but Tyler has always been able to make me cum very quickly and harder than pretty much any other guy. Maybe his masculinity turned me on more than that of any of the average gay guys I've been with over the years, maybe he just was really good with mouth, who can say? I decided to give into temptation, after all, I was single and working six days a week in a one-hundred-degree kitchen - I deserved a little bit of ecstasy.

I hurriedly brushed my teeth and took a shower, knowing that Tyler was only about ten minutes away. I answered the door in just a towel, figuring it wouldn't be on long anyway and it was much too hot to bother with clothes. I led him to the bedroom - lights off - and watched as he stripped naked. It always turned me on to watch him get undressed and see that he was already rock hard - no stimulation whatsoever. He crawled into the bed and climbed on top of me, burying his face in my neck. A sigh of pleasure escaped my lips as I wrapped my legs around his torso and held him tightly. I wanted him to kiss my neck and suck on my nipples, but he stayed where he was. Honestly, the weight of him on top of me felt amazing - not in a sexual way. He turned his head so that I could kiss him - he maintained loose, lifeless lips - before he scooted down and started sucking my dick. As wonderful as it felt, I didn't want it to be over yet, I wanted to enjoy the feeling of him on top of me.

"Are you in a hurry?" I asked, glancing down to watch him sucking my dick.

He popped my dick out of his mouth and said, "not really," in a deep, husky voice. "Why?"

"I just really like the feeling of you on top of me. I'd like more of that," I replied, shyly, grateful that the room was dark, and he wouldn't see the embarrassment flaming in my cheeks.

Tyler climbed back on top of me; I kissed his limp lips again as I wrapped my legs around him, trying to merge our bodies as much as humanly possible. Despite the overwhelming summer heat, the contact left me feeling incredibly calm and horny. He started to move his hips, his dick sliding against mine. The movement caused groans to escape my lips, which spurred him on as he picked up the pace. I found myself kissing him, holding him in place as he dry humped me.

"I bet you fuck good," I murmured, not really thinking about anything but sex.

"Wanna find out?" he asked, dry humping me harder and faster.

"I've still never bottomed," I reminded him, already feeling like an idiot for letting him think it would happen.

He put his arms on the headboard and lifted himself up, his dick slipping into my mouth as he started thrusting rapidly. "Do you have a condom?"

"No. The condoms I had were expired, so I threw them out a while ago. I have lube, though," I answered, once he pulled back enough for his dick to flop out of my mouth.

As Tyler continued to thrust against me, I couldn't help but wonder what it would be like to have him inside of me. I knew that he never lasted long with me - barely more than a minute - but I wasn't entirely sure how I felt about allowing myself to be vulnerable in that way with someone I wasn't dating and who was cheating on his girlfriend by being with me. I wanted to remind him that I wasn't cleaned out - although technically my stomach had been upset when I'd woken up and I was fairly confident that I had cleared myself out for the moment - and that he should probably finger me if he wanted to actually enter me, but his body felt so good on mine that I pushed the thoughts away. I longed for him to go down and eat me out, but something told me that while he was okay with sucking dick, eating ass was a completely different ball game. Honestly, his thick strawberry blond beard would scrape the sensitive skin down there and mar the experience for me anyway.

"I love your hands on my ass," Tyler moaned into my neck. I hadn't even realized that my hands were on his ass, squeezing the cheeks as he stimulated himself on me. "Fuck, where's that lube?"

As if I was not myself, I reached over for the lube and handed it to him. I watched as he poured a little into his hand before slicking his dick with it. I had always thought that when - if - the moment came when I was about to bottom, that I would be overcome with nervousness, that my stomach would twist into knots and my pulse would thunder in my ear; instead, I felt calm, as if this was something completely natural for me.

"Remember, I've never done this before, you have to be very gentle," I murmured as he lined his dick up with my hole and started to push in.

As he slid into me there wasn't nearly as much pain as I had thought there would be; I had always imagined intense agony as soon as the sphincter started to stretch. The pain didn't start until he continued to press into me, forcing all of himself into me. I gasped as his entire length slid into me and then he started moving his hips rapidly. It felt like I was being split in half from the inside out.

"Ah!" I cried, tightening my grip on his shoulder. "Stop! Stop, I need you to stop for a minute."

Thankfully, Tyler listened and pulled out, hovering over me with lust laden eyes.

"I need you to be gentler and go slower," I said as he started working his way back inside of me.

It hurt a lot less this time, only causing any real discomfort once he was all the way in and moving with any kind of speed.

"Fuck," he panted, thrusting into me with abandon.

As the pain started to wane and I could just start to feel a sensation that was something next to pleasurable, Tyler started breathing more quickly. Before I fully knew what was happening, I felt him pull out of me and then he groaned.

"Did you cum in me?" I asked, dazed.

"No," he replied, shaking his head. "Where's that lube?"

My fingers splayed out, skimming the sheets for a sign of the small plastic bottle. When they hit it, I grabbed it and handed it to him, unsure of what was going to happen.

"Do I get to fuck you now?"

Back when Tyler and I had started meeting up - about four or five years ago - he'd let me top him. He'd ridden my dick for almost an hour, his cold sweat dripping onto my skin and grossing me out.

"No." He poured more lube onto his palm and then spread it around before grabbing my dick and jerking me. It felt good - I didn't use lube often - helping me to forget the pain of only a minute before. I was crying out as I shot my load all over my stomach and his hand, quivering in ecstasy.

I grabbed a towel for us to clean up with and then Tyler pulled his clothes back on and left with a noncommittal, "see ya."

I immediately got into the tub and filled it with ice cold water. I didn't hurt down there like I feared I might, but I was worried that with as rough as Tyler was there might be some tearing and bleeding; on top of all that, with the heat, a nice cold bath sounded heavenly.

As I sat there in the freezing cold water, I replayed the entire event over and over in my head. It had finally happened; I had finally lost my anal virginity. While it had hurt, it hadn't been as terrible an experience as I had hyped it up to be. The entire thing had lasted less than two minutes, which made me wonder if Tyler came quickly every time or if it was because of me. Had he lasted longer, I might have gotten to properly enjoy the experience and make a concrete decision on whether or not I was open to doing it again.

I consulted with several of my gay friends, regaling them with my experience. They all agreed that I should not have let a straight guy who had no clue what he was doing break me in; they also confirmed my theory that he had been too rough and hadn't been patient enough. One friend assured me that Tyler pulling out and sliding back in had been a good thing, that it can help with the pain and the entire process. Overall, it wasn't the horrible, life-altering endeavor that I had built it up to be, but I stand firm in my belief that I would be more comfortable and enjoy it more if I tried with someone I was dating or was very close to.

I know it sounds cliched, but ever since then my entire perspective on life has changed. How could something so trivial as being penetrated completely open my eyes to things that I'd been so blind to before? Lately, I've been longing for a relationship again, a true, can't-live-without-each other romance; I know that those really only exist in movies and books, and that at my age, I'd be hard pressed to find the kind of innocent teenaged first love that I'm looking for. Logic tells me to give up on that fantasy, to face the truth and accept that all I can settle for is a decent relationship, but my heart doesn't want that. I don't want mediocre; I want fireworks and sparks, and a love that shakes me to my core. If I'd been able to be out and be my authentic self in high school, I might have gotten to experience the kind of love I crave at a time when it would have been possible; I fear that at this point in my life it's too late, that it's impossible to find a love as innocent and pure as what I want. Am I doomed to spend the rest of my life on a pointless quest, or could it be that somewhere out there in this beautiful, wide world, what I want is out there waiting for me?