My First Time

I remember my first times each and every one of them. My first kiss, my first blow job given and the first time I was taken to bed.

My first kiss was with Larry. Larry lived next door to me and we played with each other everyday when he lived there. We’d play hide and seek, we’d play tag, we’d play soldier and we’d play doctor.

Two boys playing doctor is a recipe for only one thing but at the age of nine it was still innocent. We just wanted to look and see what we had and it was better looking at another person than it was looking in the mirror.

I remember the day was hot. It was summer and we were out for school. His father worked days and my parents worked days as well. On the island it wasn’t a big deal to leave your kids alone at home at that age because the neighbors kept an eye out not that it was a good idea but it was what was done.

With the day halfway gone and having hand butter on white bread for lunch we were behind his house under the coconut tree trying to figure out what next to do for the day when Larry asked me if I’d ever kissed a girl.

“No,” I said. I laughed. It wasn’t that I didn’t want to kiss a girl but what would I do? I’d seen them on television and in the movies but I knew there was more to it than just putting the lips together. They had to be.

He said, “I wanted to kiss Katie but I don’t know…” He said.

Katie was his cousin. She was cute, she was a year older than us.

“I don’t think that’s right? Kissing your cousin I mean.”

He shrugged his thin shoulders. “I’d need practice anyway. I’d want it to be good.”

I ventured forth. “Why don’t we practice?”

Larry scoffed and laughed. “Boys don’t kiss boys!” He exclaimed.

The breeze picked up and he pushed off the tree having been leaning on it all this time one leg on the ground the other braced against the tree.

“Why not? It’s only practice,” I said.

Larry had his back to me. He was wearing a pair of red shorts. They were torn and tattered but they were his favorite. The shirt he wore was also red but in better condition with the number 5 on t he back in white. He was barefoot as I was.

“I don’t know about that.”

“It’ll be better that way I mean when you kiss Katie.”

The idea of kissing him suddenly had my heart racing.

“Are you going to kiss me back?” He asked.

“She’s going to probably kiss you back.”

“With tongue?” His eyebrows were up and there was a quizzical look on his small round face.

“Yeah why not?”

He shook his head hard and fast. “I don’t know about that man. That seems so wrong.”

“It’s not as if we’re going to be doing it all day long. It’s just a kiss,” I said and stood and moved towards him one slow step at a time trying to crowd him.

“Listen,” I said, “it’s for practice.”

He shrugged again but didn’t say yes.

I closed in on him until we were inches away and waited. He didn’t move and I didn’t move. Around us anyone passing could see us exposed as we were. In retrospect I shouldn’t have done it there but we were lucky because no one passed by.

I leaned forward but he didn’t move any closer so I went further and our lips touched.

He pulled back hard after less than a second.

His lips were soft and wet. I hadn’t even notice him moisten them for me before the kiss but he had. It sent an electric tingle through my body not at all like a kiss my mother gave me or father gave me on the cheek. This was something much more delightful that sent blood rushing to my groin and sending my small shaft erect.

“Hey you need the practice not me,” I said to Larry.

He thought about it a second and moved close again.

The leaves whispered above us as the breeze picked up again and the tree swayed with it.

He kissed me then like he was kissing Katie or planned to kiss her. Under the coconut tree under a blue sky with fluffy fair weather clouds floating by I was kissed for the first time by another male.

His tongue probed my mouth with uncertainty and with out any degree of care. It was as if he was trying to see how far down my throat he could shove it. Yet as bad of a kiss it was it still sent me over the moon with delight.

“How was it?”

“You could do with some work. Too much tongue.”

We waved me away with a dismissive hand. “You just want another kiss faggot.”

“Hey let me know how that goes with Katie.”

He told me a week later she said the same thing and we practiced again under the tree. He got better with each kiss but in the end I knew the kisses weren’t for me but were for another yet it didn’t matter they served a purpose. They opened me up to the idea that my sex was for me.

My first blow job came when I was fifteen. I had moved away or Larry probably would have been the one who blew his load in my mouth.

I lived in America now having moved with my mother and father and had new friends and new ways to feed my sexual appetite in the form of online pornography pictures and videos.

No boys lived around me or at least no boys that I knew well but at school I’d grown close to one. He wasn’t from the islands and had never visited them but he liked me.

His name was Joe. He was a slender white body with blonde hair and blue eyes. He was my height which at the time was five feet eight inches tall. He was a hundred and twenty pounds while I was a little heavier by ten pounds.

The two of us were always together. We sat together in class, we hung out during free periods together and in the end we experimented orally together.

The day was a Thursday. It had been raining the entire week in Florida. It rained when school let out and looked like it would rain for the next two days. It wasn’t a torrential rain but rather a steady drizzle that saturated everything and kept it so.

“You should come over and we can do Mrs. Wilkes homework.”

“Sure,” I said. “I’ll have my mom swing by pick me up.”

Together we ran the short distance from the school to his house crossing the street between stalled traffic because of an accident further up ahead.

We were wet when we got to his house.

“I think I’ll change,” Joe said.

“Okay.”

He stopped and turned to me. “You should too. My clothes will fit you. I can put your stuff in the dryer.”

It made sense to me so I followed him up to his room.

His room was just like mine was. The window shades were pulled so the only light came from a single lamp. He had books on the floor and on the bed that was not made up. He had a desktop that was on, the screen saver dancing across the screen.

Pulling open his closet he selected something for himself and something for me.

I couldn’t resist watching him strip. He had his back to me as he peeled his shirt off and then shimmed out of his jeans. He was wearing a pair of blue boxers and he dropped those two.

He had a nice ass, it was pale not exposed to the sun much with just a touch of peach fuzz on it. He turned and looked at me.

My eyes went to his cock.

Semi erect his cock seemed long, longer than mine at least.

“Are you checking me out?” He asked moving closer.

The sound of the rain increased as the light drizzle grew.

“Maybe,” I said.

He smiled mischievously.

We weren’t naïve in knowing that we both looked at pornography and we both masturbated in our respective rooms but we’d never talked about it except to ask what each other thought of a specific girl. Joe did a lot more of that asking than me.

“You want to suck it don’t you.”

I didn’t nod I just stared at it. He held it in his hand stroking it slowly. It got hard an harder so when he let go it stayed up right.

My mouth watered and I moistened my lips.

“Come on. I mean you have me here and all…” he teased.

I reached out and took his cock in my hand. I looked at him. He was smiling and eager to be sucked off I could tell just as eager as I was to suck him off.

I’d never tasted another man’s cum before. It was my first time. I’d tasted my own and it was salty and tasted like snot the first time but I’d read that could be changed and I was working on it.

I knelt before him and rubbed him slowly moving my mouth towards it taking it into my mouth.

He was long but not thick yet I still couldn’t fit it all the way in without gagging so I decided to focus on his head.

I sucked slowly at first moving my head as I’d seen the women in the videos do. The slurping sound grew louder in the room as the rain returned to its incessant drizzle.

Pre-cum slipped down my throat. It was salty like mine. I had no doubt that he’d taste similar to how it tasted.

His hands were on his hips. He leaned backwards slightly. Looking up at him I saw his eyes were closed and he was biting his bottom lip. His teeth were digging into the flesh.

He moaned.

I grew harder myself delighted that I was controlling him so.

Stroking him with one hand and rubbing his balls with the other I sucked harder and faster my head bobbing forwards and backwards.

The carpet was soft a Berber that was light tan in color. His computer hummed loudly when the cooling fan came on.

His moans got louder. He was cumming.

I stopped stroking him with my hand and rubbing his balls and put my hands on either side of his hip.

He pushed forward into my mouth faster and harder.

I didn’t have to move anymore. In fact I remained still just sucking him waiting for it.

I didn’t have to wait long. It was hot and thick. I shot out of his circumcised cock into my mouth in waves that I was forced to swallow quickly or choke on it.

It was only at the end that I tasted him having swallowed most of him without tasting it.

When he was done he must have thought I’d ask for one but I didn’t and he seemed relieved.

While my clothes dried we did homework. We spoke nothing of it but it wouldn’t be the last time and I was thankful because I did enjoy it and for some reason being the bitch didn’t bother me.

When I loosed my virginity it was to a college professor. No different than many women before me or maybe even men it was just a fling a way for him to notch another one on his belt but at the time it didn’t matter.

His name was Mr. Eric Helms and not who’d one would expect to want to enjoy another man. He was married to a beautiful woman who if I was straight hell if I’d had a chance I would fuck. He had two daughters two years apart ten and twelve and was tenured teaching poetry at the college.

For a poetry professor he was definitely not what one would expect. He was six five and close to two hundred and fifty pounds all of it muscle and hard muscle. He seemed a man’s man and when I entered his class for the first time I saw there was a second meaning to that phrase.

Except for myself the class was filled by women. They were the beautiful college women from blacks to whites to Asians and even Hispanics but he was the only guy in the class besides the instructor.

Mr. Helms was a handsome man with bold features black hair going grey and dark brown eyes. Those brown eyes found me immediately probably because I was the only guy in the class but also I know now because he had his sights set on me from the get go.

The class went as I expected. It was an elective and I liked poetry. I hadn’t scoped out Mr. Helms in the least but from day to day I could tell he was interested in the dark skinned guy, me, in the back of the class.

After two weeks he told me to stay back much to the disappointment of many of the women I’m sure but that wouldn’t stop them from trying. No one would have guessed he was interested in men.

He liked one of my papers on Shakespeare and invited me to coffee to talk about it. I agreed and we met in an off campus coffee shop later that day.

We talked about him at first then we talked about me and from then it was mostly about me. He wanted to hear about the island I was from, my parents and what they did for a living and what I expected to get from the class.

“It’s just an elective for me,” I said.

He laughed. “Honesty I like that.”

I smiled.

When we parted company I could tell something was there but not what it was. I had no illusions that he’d be the one. I had my illusions rather on probably going to a gay bar and finding a hook up for the night so I could really see if this was for me.

The idea of having a cock up my ass aroused me to no end. I’d already bought two dildos a small narrow one that was merely a long silver tube that slipped in and out of my ass easily once lubed and then a cock made in the impression of some porn stars dick that I only managed to get in to the head and no more.

I’d lay on the bed on my back legs up like the bitch I was and have one or the other in my ass moving it slowly with my left hand while I stroked myself with my right hand to a climax.

It was delightful but cold materials weren’t the same.

After the midterm and various other meetings for not only coffee but also basketball and soccer Mr. Helms called me back to his office.

His office was small. It could barely fit the table in it and had one window that was grimy on the outside. It was night when we met. He was behind his desk sitting and I was sitting in one of the two visitors chairs he had.

He told me my mid term paper was excellent and that he wanted to use it in a publication.

I agreed.

“I’m sorry I don’t have anything to give you in return.”

“I don’t need anything really.”

Someone had to make the first move.

He stood from behind his desk and moved around to me. He sat in the other visitor’s chair and put his hand on my knee.

I was wearing a pair of blue jeans and a black polo shirt with a leather jacket. His hand was warm.

He squeezed my knee his brown eyes holding my gaze.

My heart fluttered with delight.

“Normally one of the girls would be sitting where you are begging for a better grade but there’s no better grade I can give you.”

“So what should I be begging for?”

He smiled. He leaned over and kissed me on the lips full and hard.

A shiver passed through my body.

We kissed and kissed how long I don’t know but when we broke we were eager to go further but decided it would be best to do what we intended in a motel miles away from the college.

That week we planned a trip. He gave me the cash and I was to book the place and so I did.

It was the third motel on the interstate. Paying cash and using a fake name brought privacy.

It was Fall then. The weather had turned cool and in Florida the trees didn’t really turn color even in the north of the state where I was attending college.

The room was a simple one. There was a bed and a small desk with a chair next to it. The bathroom was not much merely a stall with a shower and a sink with bars of soap in paper wrappers.

The bed wasn’t too bad though and for a place for his first time it could have been worse.

Mr. Helms told his wife he was staying late. I didn’t care what he told her.

A week waiting knowing what to expect I prepared myself as best I could and waited for him to arrive.

He arrived on time and dressed in jeans and a black turtle neck sweater.

“Hey,” he said entering.

“Hi,” I said and closed the door.

I wasn’t sure how it worked but I didn’t have to worry about it for long. Mr. Helms sat on the bed and patted next to him.

I sat down.

He kissed me soft on the lips and the neck. I felt chills wash over me. I wanted him so bad. I wanted him in me.

He made me stand and strip for him.

Not self conscious one bit I stripped.

Since my teenage years I’d grown a little. I was now five feet eight inches tall which was still much shorter than Mr. Helms and weighed a hundred and fifty pound slender but athletic.

My features hadn’t changed much over the years and I still had soft features which I didn’t try to make any harder.

He stood and peeled his turtleneck off.

I was impressed by his muscles.

He dropped his pants and I was further impressed by his member.

I knew the drill and I wanted to anyway, suck him, so I moved in and took him in my mouth without preamble.

Since Joe I’d learned a few more tricks than straight sucking. I’d learned that to stiffen the tongue and tease a man’s penile opening got quiet a reaction from some. I learned that focusing on the rim of the penis got most if not all men off quicker than anything else. I learned that sucking a man’s balls didn’t always feel nice. I used all these tricks on Mr. Helms as I’d used it on countless others.

I’d given blow jobs to many men though none had taken my ass. It wasn’t because they didn’t want to they sure did but in the end they were mostly satisfied to unload in my mouth.

Mr. Helms was not eager in just a suck. He wanted a suck and a fuck and after how long I don’t know he had me on the bed on my back facing him.

He had my legs up and a condom on.

My ass was lubed generously and teased with my own finger. He insisted I finger myself and then suck it like I sucked his cock.

I obeyed without question.

He guided his cock to my hole. It looked like nine inches or more. A white python in his pants come out to play.

Thick and engorged he pushed into me. It burned as I stretched and he filled me.

“Rub your cock,” he said.

I rubbed my cock and balls furiously. The pleasure would overwhelm the pain.

Only his head was in and he kept pushing deeper and deeper.

I winched and tried to pull away but he held me fast and before long his cock was in my rectum all nine inches of it to his balls.

He didn’t move.

“You’re a virgin,” he said.

I bit my lip and nodded.

He stayed in my not moving as I slowly rubbed my cock. Then he started to stroke me. He moved very slowly at first. The lube did its job and soon he was moving in and out like a slow piston.

As much as I yearned to be ass fucked it still was uncomfortable but I took it none the less. I took it like man and let him free in me.

His hands were on the back of my knees and he pushed my feet up to my head raising up off the bed for leverage as the urge to climax grew in him.

He was enjoying it.

I was enjoying it too now. I was stretched and I was going to cum soon. I’d been rubbing my dick slowly to delay the release but as the pace of his pounding increased I wanted to cum. I wanted it to squirt up on my stomach.

He grunted and panted the sound of flesh smacking loud in the room.

My heart was racing and my skin was clammy with sweat. So was his.

I closed my eyes. Hot cum shot from my cock onto my stomach over and over until only a dribble oozed down the side of my cock white and creamy and thick.

I opened my eyes to see Mr. Helms throw his head back and open his mouth.

Because of the condom I didn’t feel his cum in me but I knew he came. It was all over his face as it had been over Joe’s face when his first load wet my throat.

He stayed in me until he grew flaccid.

On the bed we lay breathing hard. The total elapsed time was two hours since he arrived.

It was another hour before he took me again. This time I was on my stomach and my ass in the air taking not only a pounding but brutal smacks that I felt sure was turning my chocolate brown ass red with welts.

The pain and mix of pleasure was sweet but I was sure it wasn’t for me.

He came on me then that second time. He whipped his condom off at the last minute and shot cum onto my back and my ass more than I would have expected for a second time.

The third and last time any discomfort from anal penetration was subsided. I rode him gingerly. He was on his back and I was on him facing him with one hand on his chest and the other reached back and playing with his shaved balls.

An hour of bouncing on him resulted in a sweet climax for him into another condom and a sweeter one from me onto his stomach, which I gladly lapped up for his enjoyment.

We spent the rest of the night talking and laying naked in the bed spent.

The next day we parted company. He left first and then I.

In class it was as if nothing ever happened. He didn’t seek me out any more than anyone else nor did he invite me to coffee or to his office again. I’d been a prize and he’d won it and he was moving on.

I later heard that he had a thing for black boys. I didn’t care. He was my first and I knew he wouldn’t be my last. My next goal in life after the kiss, the suck and the fuck was now to find a buck to be mine in other words to find a partner for life.