Taking My First V-Card

While losing my virginity was no John Hughes film, I’d like to think that when it’s been my turn to deflower a guy, I’ve usually provided a decent experience.

All characters in this story are 18 or older.

The summer after my freshman year in college was annoying.  I’d been openly gay when I went to school and I’d had no push back at all (the perks of going to a hippy school in a hippy town can’t be underrated).  I’d gone on plenty of dates and hooked up with a lot of cute guys so it’d been a success in that dept.  But that summer I was back home and at this point the small southern town my parents lived was stifling.  I didn’t have many friends at the end of highschool so I was usually hanging by myself and on top of that, every hot guy that was on Grindr was in the closet, couldn’t host or drive, and usually lived 30-60 mins away.  T’was a dry summer if I ever had one. 

That changed when I took the chance to go and stay with my grandma up in Ohio that July.  While the area my family was from in Ohio wasn’t a booming metropolis, there were way more things to do and guys to meet than back home.  One particular guy stands out though in my memory because he was the first virgin I ever fucked. 

We matched on Tindr while I was swiping the app at my grandma’s.  This guy was beyond stunning.  His lips were broad, his eyes were chestnut brown, and his nose and jaw were sharp while he still had a sweet ass smile in his pictures.  He kept his brown hair a little past his ears and he might as well have had a halo above it because this was the most beautiful guy I’d ever seen. 

His name was Chase and he lived about 20 miles down the highway from my grandma’s. We chatted a bit and he mentioned he had just graduated highschool and was still with his parents.  I asked if he wanted to hang out and he said he’d like to but could only meet up late at night because his parents weren’t happy about him meeting up with guys yet.  Luckily, I had my car with me, my grandma went to bed early, and she didn’t mind me going out late.  She also didn’t usually wake up after bed since she had a hard time getting around and wouldn’t notice just how late I was out. 

That night I drove down to his town and got there around 10:30-11 pm.  His house stacked up against a large hill that the road wrapped around and a little ways down from his house was a gravel lot that he told me to park in.  I let him know I was there and he made his way to the lot 5 mins later. 

He looked exactly like his pictures and his voice was soft and sweet.  He smiled as he sat in the car and said he wasn’t sure if I’d come.  

We sat in the car for an hour or so and just talked a bit.  He was going to be starting community college the next month, he lived with his parents and 2 siblings.  He liked playing video games and had only ever made out with one guy before at a summer camp the year before.  I didn’t actually know he was a virgin before then, but at this point I decided I definitely needed to fuck him before I left Ohio.

I went ahead and asked if I could kiss him and with that drop dead smile he said yes.  I leaned over and we started to make out slowly.  He tasted so good and those soft lips drew me in even more.  After a few mins we hit my back seat so he could sit in my lap.  This was already dangerous because that left my hands right on his ass and once I copped a feel, I knew I was done for.  On top of being pretty beyond belief, and having a snatched waist, this boy had the roundest and smoothest pair of cheeks I’d ever held in my hands.  

While we made out I squeezed his cheeks, running my hands slowly under his shorts and back out until I slid them all the way in and realized he didn’t have any underwear on.  Ok, maybe this guy wasn’t so innocent after all.  

At this point I was kissing both sides of his neck, grazing my teeth against his skin as I went up and down.  He moaned low and gasped when I hit his collar bone.  I gently tapped my finger against his hole while I massaged his ass.  He let out a whimper. 

We took off our shirts then went horizontal in the back seat.  With him on his back I started kissing and biting down from his collarbone to his chest then stomach.  Finally at his hips I kissed them then went back to his lips and asked, “So can I eat you out?”

He smiled again, “I did shower earlier.  But like, I’m not ready to go beyond that”

Bingo we have a winner.

I nodded and said between kisses, “And that is totally fine.” 

With that, I pulled off his shorts and worked my mouth down his thick thighs and at last to his hole.  Biting both cheeks a bit, I started slurping up and down his hole and lapping him up. This turned his moaning and gasps up another level and that got me going even more. After a couple mins I told him to sit on my face.  From there he pulled out my dick from my shorts and we were 69ing.  For a virgin, he did a great job sucking on me and working my balls with his hands. 

This went on for a bit until I came in his mouth and he swallowed me up. I sat up against the car door and he moved onto my chest as I wrapped my arms around him.  We laid there for a while as I ran my fingers through his hair and across his back while we caught our breaths.  We talked for a little bit and agreed I’d come out the next night.  We kissed a little more then got our clothes back on, and I dropped him off at his house as I headed back to my grandma’s.

The next night I came prepared with a blanket I’d snagged from my grandma’s and we posted up on a hill across the street from the gravel parking lot.  We were far enough off the road that the street lamps dimmed in the distance and you could see the stars perfectly clear above as we crashed back on the blanket.  

After the previous night, we didn’t waste much time.  We were rolling around with one another, grabbing each other and kissing in a frenzy as clothes were slowly removed and our mouths found new places to go. This all led to us being butt ass naked in the dark in the open air and tangled up with one another. 

During the day we’d texted a bit and he said he’d be down to go all the way.  So as my mouth found his hole this time I knew I needed to get him as ready as possible.  I stroked his holed up and down with my tongue, slowly prodding inside here and there just to get him to open up some.  After fifteen mins I put him on his back, threw on a condom, lubed us both up and tried to slide in him. 

Unfortunately, missionary didn’t work for him starting out and he swung into doggy.  I tried again, moving my dick up and down his hole and slowly pressing in. Again, he said it felt uncomfortable.  At this point, I thought the problem may have been the condom since I’d had that issue when I tried bottoming at points.  Thankfully, I’d gotten tested and cleared of everything right before summer, so I asked him if he’d want to try without one.  He said he was down. 

So I rolled the condom off, lubed us back up, and this time slowly entered into him.  He gasped and I held steady, trying not to move so he could adjust to me.  I leaned over him and kissed his jaw and down his neck from the side. After a little bit I started slow thrusting in and out, feeling his hole open up as it gripped my dick.  God he felt amazing and the sight of my dick sliding into his perfect ass was driving me fucking crazy.  I checked in to see how he was doing and he said it felt good through a soft moan. 

Picking up pace, I held his cheeks in my hands and really started to work him out.  All the while you could hear the light clapping of his cheeks as I dived in and out.  Slowly he collapsed onto his stomach and I continued to dig him out, feeling myself get deeper in him as I kissed his back and neck.  Here I was under a beautiful night sky, balls deep in one of the most beautiful guys I’d ever met.  I must’ve been doing something right.

I started to get close and asked him if I could cum in him and he said “Please”.  I wrapped my arm around his neck from the back and thrusted as deep as I could over and over until I felt my starting to cum in him. When I tell you it was basically a religious experience, I’m not fucking kidding.

I fell on him and wrapped my arms around him from behind as we rolled to our sides huffing.  It took us sometime to catch our breaths after, but the rest of the night we spent cuddling like that and then fucking two more times.  I really just could not get enough of this boy. 

Unfortunately, around 3 am we had to pack up and get him back to his place again. On the car ride home though, I could not stop smiling.  

Notes:

Being someone’s first isn’t an easy thing to do if you wanna do it right.  It means taking a lot of time and getting their input through the process so you can make sure it’s as fun and pleasurable as possible.  If you do it right, you’ll be able to leave a good impression.  Over 5 years after that first time, I talked to Chase again, and he said he had yet to find someone who could eat him out as well as I had. 

Another component of being someone’s first time is the sensual side of things.  Kissing, body contact, and cuddling are important if they’re down for it.  It helps establish trust and an actual bonding experience instead of a quick fuck. Now, some guys may want the whirlwind fucking to be how they lose it, but let them spell that out for you.  Otherwise, be prepared to put in the time and work to make it a sweet and enjoyable first time. 

I think that while virginity has been overblown in western culture, maybe we over think the wrong things and underestimate the right ones.  Rather than it being some magical and perfect romantic experience, maybe it’s best just to make it as comfortable, fun, and relaxed as possible.  Sure, chemistry matters, but a lot of times this may not be your future husband.  Instead, it could just be someone that you’re going to set the bar for, and it’d be better that they have good standards to judge their experiences going forward.

- Darian Black

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