Matt and Oliver Ch. 01

I have to admit, I never thought that i would lose my virginity to a guy. Being bi, I always just assumed I'd lose it to a girl since there are a hell of a lot more straight girls than gay guys. I'm surprised that I lost my virginity to a man, but that doesn't mean that I'm not happy about it.

His name is Matt, and he is amazing.

Matt and I had been friends for years leading up to this. He moved to my town when we were in first grade, but we never really talked until we were in third. He was actually my first crush. I didn't know it at the time, but he would easily be the main reason I discovered my sexuality. For the past fifteen years he and I have been best friends, hanging out at least once a week and frequently texting or calling each other, whichever is convenient at the time.

Now that I look back on it, I see all the signs. But up until yesterday, I was blissfully unaware to the fact that he liked me.

About four or five years ago, I can't remember, I came out to Matt as bisexual. He helped me through it all and was very accepting. He was always there for me, trying to be my wingman and find me a boyfriend.

Sadly, he isn't very good at it, but I guess that doesn't matter now that he's my boyfriend. Is he my boyfriend? I'm not really sure. We'll figure that out later.

For almost a year he's been crushing on me really hard, but I never realized until just now, one of the best moments I've had in a long time.

We were both at my apartment with another friend, Nicole. She graduated the same year as us and we even share a birthday. She hates admitting it, but I'll always be at least twenty three minutes older than her, a fact I was glad to remind her of on her twenty first birthday. We did what we always do whenever the three of us are together, played cards, video games, screwed around, and just talked. Around six o'clock Nicole told us she had to go.

"Work doesn't wait," she said, looking straight at me. "Of course you'd know that if you ever got a job, Ollie."

"Oliver's fine," Matt said, butting into the conversation.

"Mmhm," Nicole retorted just before leaving.

Matt and I decided that without Nicole around, there wasn't much we could do, so we just decided to watch a movie. I bent over and reached into a movie bin I keep by my TV. Matt sat on the couch, waiting for me to pick a movie.

When I stood back up and turned around, I couldn't help but notice that Matt quickly turned his head away from me. Was he looking?

I was wearing skinny jeans which were extremely tight, especially around my butt. They were tight enough that whenever I bent over, you could see the outline of my panties through the denim.

I never really liked wearing guy's underwear. It makes me feel too masculine, and that's not something I tend to enjoy. I find wearing panties to be a lot more comfortable and exciting. Yesterday I was wearing purple cotton panties. They were really soft and comfortable, especially around my crotch because they didn't require too much tucking.

Ignoring the fact that Matt may have just been checking me out, I walked over to the couch and take a seat next to him, folding my legs up to my side and sitting down leaning against the back of the couch in the seat directly next to Matt.

The movie began to play, and for the next hour and a half the two of us just sat there, watching the movie and occasionally making comments about what's happening. It wasn't until I woke up with my head on his shoulder that I remembered we were watching a movie.

Confused and worried that I made Matt uncomfortable, I quickly straightened myself up and apologized, looking at Matt who seemed a bit distressed and startled at my sudden movement.

"Why are you sorry?," he asked, looking at me as I blushed from embarrassment.

"For falling asleep on you."

"I didn't mind," Matt said, smiling at me.

I just sat there, confused at what Matt was saying. What did any of this mean? I didn't know it yet, but I was really going to like the answer.

"What do you mean?," I asked, looking for clarification on what he was saying.

I asked the question and before I knew it I was in his lap, kissing him while his hands were rested on my hips.

This is where I am now, and I couldn't be happier.

It isn't too long before I'm on my back, him over me with my legs around his waist. He keeps kissing me, using his tongue more progressively the longer the kissing goes on.

With my legs around him, I can feel him getting harder and harder as we keep kissing. I can tell he wants more than just kissing, and I am fully prepared to give him a lot more than just kissing.

I use my hands to guide his to my shirt, telling him without words to take it off. He pulls my shirt off just before taking off his own. He then immediately goes back to kissing me, getting as hard as humanly possible while doing it.

I decide that the best course of action from here is to let my hands wander. I know that I'm not the only one that wants this, but I definitely am the one that wants to be the one doing stuff more.

I slide my hand down Matt's chest and onto his crotch, staying above his pants just in case that's not where he wants this to go. I grab what I can from outside and then slowly begin stroking, feeling his hard cock in my hand while our tongues wrestle.

After around five more minutes of kissing, I put my hands on Matt's chest and gently push up, getting him off of me before leaning him back in the couch.

I kneel on the ground, spreading his legs out and getting between them. I then go for his belt buckle, undoing it before unbuttoning his pants. I then unzip his jeans, revealing his underwear that is doing a pretty poor job of hiding his hardon at this point.

As I slide his pants and underwear off, I realize what it is I'm about to do. I've never given a blowjob before, not to a real person at least. The most I've ever done is suck off one of my dildos, and those certainly are not the same thing.

Swallowing my pride, and hopefully something else later, I take Matt's pants completely off and then grab his cock, stroking it gently with me right hand as I run my left up and down his thigh before using it to massage his balls.

Scared yet very curious, I wrap my lips around the head of his cock. I then begin to slide down, letting his dick fill my mouth. I run my tongue along the bottom of it, tasting every inch of his nice hard shaft as I stuff my mouth with it.

I suck Matt's dick for multiple minutes, listening to him moan and breathe more heavily the longer I go on.

After about four minutes, Matt tells me to take my pants off, but leave my underwear on. He knows I wear panties, and no doubt wants to see how I look in them.

I remove my pants, exposing my ass and cock that are being covered up only by a pair of purple panties, soft and tight in all the right places.

Matt puts his hands on my hips and then lays me down on the couch. He lies down on his chest in between my legs. He grabs the waistband of my panties and begins to pull it down, letting my cock come out and get harder as he slides my panties down my hairless legs.

He then sticks a finger in his mouth, getting it nice and wet before lifting my legs up and staring straight at my asshole. I stare down between my legs, watching as he sticks his tongue straight inside of me and begins to eat me out.

I keep getting harder and harder the longer he licks my asshole. After about a minute of eating me out I feel a few fingers enter me, and I love it.

Matt just continues to finger me for the next few minutes, sucking on my balls while he does so. The feeling of his fingers slowly going back and forth inside of me is enough to make me moan. I moan loudly and notice my breathing is getting heavier and heavier.

If this is how I react to his fingers, how am I going to react to his cock?

Luckily, I don't have to wait to find out. I feel Matt pull his fingers out of me and watch as he starts to suck on them. He then begins rubbing the top of his cock against my asshole, making sure that I know what he's doing as he does it.

It isn't too long before I feel him pushing, and I want nothing more than for him to just be inside of me.

He slowly slides his cock in, first the head, then the other six inches made of just his shaft.

The feeling I get as I feel him enter me is easily the most amazing thing I've ever felt. At this point, it can only get better if he cums in me.

He slowly begins to thrust, but this thrusting doesn't stay slow for very long. After only a couple of seconds it progresses to hard thrusting as he pounds me.

I lay down on the couch, my legs in the air as his hips slap against me. His cock slides along my insides, making me want to cum, but all I can do is moan.

He continues to fuck me while I'm on my back for several minutes, before pulling out and telling me to stand up.

I oblige, knowing that whatever he wants to do I'm fully prepared to do. He then bends me over the arm of the couch and shoves his cock inside of me once again, fucking me even harder now than he was before.

He fucks me for a while in this position, and I can tell that he's getting close to finishing. I don't want to risk losing this chance, so I need to tell him now rather than risk him not doing it.

"Cum in me."

Matt listens to this of course, fucking me for only around thirty more seconds before finally finishing. He fills my insides with his cum and then pulls out, watching as his cum drips out of my asshole and onto the floor.

I immediately turn around and squat down on the floor, putting his cock in my mouth as I stroke mine with my right hand. He continues to stare at my ass, cum dripping out of it.

I spend the rest of the night sucking him off, getting every last drop of cum I can out of his cock, before swallowing it all. The two of us then took a little journey to my bedroom, where we had sex one more time before falling asleep together, him holding me in his arms.

Surely, this will be the start of something great.