The First Time

Author's note: Many thanks to Luxx, Onyx03 and TheMasterBaiter for their help in brainstorming and editing.

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The first time I had sex, it was not with a lover.

In fact, I was not even at home. I was in Barcelona with a family friend, George. Because it is a city that never sleeps and the way you're blinded by it's beautiful lights, this city remains my favourite. I can still remember the thrill of walking down the streets at night. It was full of merchants and because of that it was noisy. The street food was probably the most exciting thing. As soon as I stepped out of my hotel, I could see the different tapas carts. I preferred the gambas al ajillo; George liked the calamars.

It was my eighteenth birthday and my parents had allowed me to travel as an adult outside my home country, but only if George agreed to come with me. He quickly agreed. He was my best friend and despite the age gap of eleven years, we were close. He saw me grow and turn from a girl into a young woman.

At the tender age of eighteen, I was not ugly but I was not pretty either. At least, I did not feel like it. It was not that I lacked confidence but, it was just that I never gained the attention that I hoped for. I remember feeling like I was unattractive when I walked around in the city. The other girls had curves in all the right places and when I looked at them, I recall feeling attracted to them. George, on the other hand could be compared to a good wine - The older he became, the finer he got. With broad shoulders and a jawline that you could grate cheese on, he did make heads turn.

It all happened on the day after my birthday. We were at some sort of club and we had already enjoyed some drinks. He had a few glasses of whiskey and, on his suggestion, I had some vodka mixed with Red Bull. It's still my favourite drink.

Oddly, it was not my first time drinking. He was the one who introduced me, during my sixteenth birthday, to whiskey. I enjoyed it but that night; I did not want to feel posh or fancy. I wanted to feel the buzz of the alcohol. After a couple of cocktails, we were still sitting at the bar and despite a few girls approaching him, George did not pay them any attention. It seemed that he wanted to focus on me. I assumed he wanted to protect me.

"You know, you can go have fun." I said.

"And leave you all alone while I satisfy those girls?"

"I won't be alone. In fact, I don't plan on going to our hotel tonight."

He raised his eyebrows, "Emma, are you telling me that you plan on losing your virginity here? With someone you barely know?"

I laughed, "What's the big deal about it? Don't tell me you knew Samantha's favourite colour when you snuck her into your room and fucked her."

Samantha was the one who took George virginity, at the youthful age of fifteen. I tend to believe that she was the person who moulded George's preferences in girls; tall brunettes.

Despite me finding what I had said being funny, he did not.

"It is very far from pleasant to hear this from you. You need to do it with someone you trust and who will respect you, Emma. Not some man you've just met in a bar. Don't you want something special, something that will be pleasant to recall? "

While what he said did make sense, it was completely unfair. At that epoch, I did not have any male friends. My school days were spent among girls in a Catholic school and the only males I knew were younger than me; I was their tutor.

"That's not fair. You know you're the only guy friend I have, G."

"Tough luck then. Make some friends, nerd."

He was wrong and I was stubborn. I had come to Barcelona to lose my virginity. I was not going to back down that easily. As we continued to sip our drinks, I continued to think about my mission. Then, I started joining the dots.

George was a man.

I trusted him.

I needed to fuck a man who I trusted.

Bingo.

I knew that I would need to convince him that I really wanted him to deflower me, to make me a woman. But I was confident that I could do that. I knew George. I knew that he liked me, and that he did not see me like a little sister. He would not have shared the things he told me with his sister. He treated me like his best friend. I wanted him to make me a woman because I trusted him. I remember when I saw him in this new way that night. I knew that he would take care of me and that he would make it worthwhile. I did not want romance. I didn't want petals on the bed. I knew that deep down, I really wanted someone that I could trust.

I don't remember what he had been saying before I told him my idea, but I do remember his "What the fuck" expression after I explained it. He was very hostile at first, saying that he did not want to lose our friendship and that my parents would probably kill him. I put forward arguments that he could not refute. I reminded him of the trust we had in each other and added the not so gentle threat of opening my legs to anyone passing if he did not take me this instant. He cussed himself at showing me the arts of arguing. Eventually, he agreed.

From there, and until we reached his room at our hotel, things happened in a blur. But I do remember the thrill that I got on the ride back when he gently placed his big hand on my inner thigh, as if to ask for permission. I granted it to him by kissing him.

My first kiss was with my best friend, in the back of a taxi.

I guess that was my first makeout as well. His hands did not leave my hair. He was gentle. I was clumsy in my kissing, I was probably his worst but he did not say anything. I could feel him smiling in the middle of it and I remember tugging on his lower lip, something I had seen on Gossip Girl.

When he grunted and asked in a thick, excited voice, "I can feel your enthusiasm. This is the last time I'm asking. Are you good?" I felt proud of myself. I gained a little bit of confidence.

I did not reply. Instead, I climbed on top of him the small taxi, grabbed his hands and put them under my dress. Then I resumed kissing him. As his hands roamed over my body and squeezed my breast through my bra, I felt his cock stiffen under me. The bulge caused my panties to press against my cunt. I realized how wet I actually was. My clit was tingling and I could feel myself clenching while my juices leaked out of me. I recall not being able to control myself and slowly started moving my hips. It felt so good. It was in a perfect position and I could feel more and more sparks going through my body.

At that time, I had never experienced an orgasm. Not because I wanted to wait but because I could not. After several masturbation sessions, no matter how I touched myself, I was only left frustrated. I would go to the very edge only to stay there. I could not figure out what I had to do. I felt guilty that I did not know my own body.

However, this time I could feel myself going higher than I ever had with the amount of pleasure that I was getting from rubbing my cunt against his erection. I knew that I was about to come. I stopped kissing him and buried my face in the crook of his neck, biting his skin and whimpering. Writing this makes me wet as I remember how he winced and then growled when my teeth pierced his skin. I felt him growing harder and bigger under me and making the pressure on my clit stronger. I closed my eyes as my breathing became more erratic. I knew that I was ready to have my first orgasm. I felt how close it was.

To this day, I can still feel the anger and frustration that I felt when George put his hands on my hips, preventing me from moving them. I fell from the height so quickly that I clenched his shirt in my fist and groaned. I pulled away from his neck and looked at him with fury in my eyes. That bastard was smirking. I could see that he was enjoying the power he had by refusing my pleasure.

He grabbed my face, kissed me and made me sit next to him, "Not here. The driver is watching us."

I rolled my eyes at him but did not say anything.

He did not stop touching me, however, running his hands over my body; making my skin sensitive and flushed. He kept me in a constant state of arousal. He kept stroking my legs and eventually, his hands went inside the top of my dress and he started fondling my small breasts. It was that day that I learned how sensitive my nipples are. He pinched and pulled them mercilessly. I can still remember the confusing ache and pleasure coursing through my body and going directly to my pussy. My back arched from something that I had never experienced before. I wanted to pull back but at the same time, I did not want him to stop. I had never played with my own body this way and there I was, discovering myself because my best friend was playing with my body. When my eyes closed, he realised that I was getting overwhelmed with sensations and he stopped torturing my nipples but continued to roam his hand over the rest of my body.

The ride had never seemed so long. I was dripping wet by the time we arrived and I probably left a stain on the seat. I could feel that the back of my dress was soaked because the wind made the cold cloth stick to my ass. After throwing some bills to the driver, we strode through the lobby to the lift. Inside, we continued to kiss. I felt almost awkward because I did not know what to do with my hands until I figured that I should probably copy him. Just when I was about to slide my hand under his shirt to feel his bare skin, the door of the lift opened and we walked through the corridor to his room.

Now that I think about it, not a lot of words were exchanged. It might have been because of how comfortable we were with each other or because he was embarrassed as well. Our breathing, the sound of my heels on the floor, and the clicking of the closing door were the only sounds that could be heard.

He led me to the front of his bed and I stood in front of him. For a very brief moment, nothing happened. It was like we were frozen. When I realised that he was not going to do anything, I quickly moved my hands up to the first button of his shirt. I remember how sweaty my palms were as I undressed him. I brushed it off as the anticipation. However, I know that I was somewhat scared.

What if my first time really was supposed to be my first boyfriend?

I did not allow myself to get disrupted by those thoughts. After untucking his shirt from his pants, I tried pulling it off him. He chuckled when he saw me struggling and removed it himself. He tossed it somewhere in the room and we were back to being still.

Was I supposed to take off my own dress even though I undressed him?

I remember vividly the anxious feeling I had of being nervous that he would change his mind. So, I turned around, grabbed my hair, pulling it to one side. I did so to expose the zipper of my dress; hoping that he would get the message. I felt his trembling hands touch my back before he unzipped it.

The atmosphere was tensed so I tried saying something funny.

"So you usually wait for girls to tell you to undress them?"

He stayed silent for a couple of seconds and then he smirked.

"They are usually already naked and waiting for me."

We both chuckled while I rolled my eyes. I felt proud of myself for making him smile. My dress fell on the ground and I stepped out of it. I stayed in front of him with my matching lingerie and high heels.

"You really planned this, huh?"

I nodded. I did not trust my voice at this point. I did not want him to think that I had changed my mind, but he was right, I did plan it.

I got closer to him and traced his body with my hands. At that time, I did not dare touch his nipples. I was foolish. I should have. My hands went down the front of his pants until I felt soft hair grazing my palm. I could tell he was somewhat excited as well, I could see his muscles twitch as if he was straining to hold them. I reached for his belt and unbuckled it.

I don't know why I did what I'm going to tell you about next, but one thing I am sure of, it was a bad idea.

In one swift moment, I just dropped to my knees and pulled down his pants. The way George sucked his breath in should have been a warning. He was not expecting this and I am sure that he was not expecting me to yank down his boxers as well. His cock sprang out and was in front of my face. He did not say anything but just watched me.

I was in awe. I tried jerking him off quickly, not wanting to make him change his mind. I was probably really bad at it. It was my first time touching a cock. I still remember how it felt, the rough and still somewhat smooth texture. How it was heavier than I had imagined and how it was oozing cum.

Then, without using spit or the oozing cum, I tried jerking him off way too hard. At that time, I thought I was doing a good job. I didn't think anything of it when he quickly grabbed my hand and told me, "Tonight is about you, not about me," but I'm sure he did it just to stop me from hurting him.

He helped me back up and then turned around, gently pushing me onto the bed. The moment my back touched the mattress, I froze. I remember thinking 'shit's about to get real.'

He came down to my face and quickly gave me a peck on the lips. He slowly travelled back down and placed kisses all over my body. It did feel good. I guess because it was my first time experiencing someone else's lips on my body, it was electrical.

He did not remove my bralette, just pushed it down exposing my breasts to him. He sucked on my nipples and for the first time, my back arched. I reveled in this new type of pleasure that made me buck my hips and put my hand in his hair. It was almost too much but at the same time, it felt so right. It was an aching pleasure that I did not want to stop.

He did not leave my other nipple without attention though. He used his rough fingers to pull and pinch it. I felt both of my nipples hardened and when he pulled back, I whined. I did not understand what was happening to me but I knew that I loved it.

He moved to my stomach, slowly rubbing his hands over my skin and kissing me everywhere. He smiled when he heard me and laughed because of how ticklish I was. He kissed my belly button one last time before moving to my panty covered mound. He gently blew on it and oddly, it felt good. However, I had not realised that he was stopping me from moving my hips by wrapping his arm around me until I instinctively bucked them.

He raised my hips, pulled down my panties and put them away. At first, I did not want him to go down on me, I was too shy and too insecure about what he might think. I was worried about my scent and how I tasted down there. I was surprised when he slowly rubbed my freshly shaved pussy with his palm. Later, he told me that he was appreciating the view. He told me that he went slowly because he wanted me to be sure about my decision.

However, I did not have time to tell him that I was too insecure. He used one of his big hands to raise my hips and the other, to slowly explore my cunt. He collected the moisture that was coming out of me and rubbed it around till my wetness completely covered my sex. He licked me all the way down to my ass and then back up to the very top of my lips where he started toying with my clit. My hips were writhing on their own, and I remember having to fight just to keep my eyes open.

I wanted to see what he was doing to me.

It felt oh, so good. It was at that moment that I realised that although I did give the same treatment to myself when masturbating, it is different when it is someone else doing it to me. It was the anticipation and the desperate waiting that made everything more arousing and more pleasurable.

After he had me squirming on the bed under his fingers, he lowered his face, licking and sucking my clit. At this point, I could feel my clit pulsating in his hot mouth. I remember how he looked up at me, and how sexy the whole situation was. The way he was looking at me made me feel so vulnerable and yet so good about myself. He was letting out moans and groans, almost growling while continuing his blissful assault on my body.

Because of how submerged I was in these new feelings, I almost did not notice one of his very thick fingers at my entrance. It was impossible for me to tense up as my mind was totally focused on the pleasure. When he slid it in, I realized that one of his fingers was thicker than two of my fingers, which is what I normally used on myself. He fingered me until he suddenly added a second finger and started to slowly stretch me. I felt a slight burn but with his mouth on me, the burn added to the pleasure.

"Your cunt is so tight, Emma."

My eyes widened. Something shot into me. It felt good to hear this crude word coming from his mouth. It was the first time that I heard him using such words. I felt myself clench around his fingers and my hips would have bucked violently if he was not holding me down.

He must have noticed because he smirked before going back to work on me. He continued moaning, while fingering me. Eventually, he found my g-spot and started to rub it. I kept clenching on his fingers, as if my body did not believe what was happening.

Then I felt it...

...the building pleasure accumulating inside me. The pleasure again became too much, but I did not want, would not ALLOW it to stop. My hand went to his hair, pulling him closer to me while clenching my thighs around his head. I did not want it to stop. It kept going and going, becoming more intense with each lick, suck and movement of his fingers. My mouth was slack, I was moaning loudly and when I looked down, I saw him looking at me. He saw me and knew.

He started moving more furiously wanting to take me over the edge. What really made me cum was when he started humming and growling. He became so animalistic. The foreign and unexpected vibrations pushed me over the top and I came. My very first orgasm was an intense one, my hips kept bucking and I pulled him closer to me. I arched my back and I felt pleasure coursing through my body. I remember tears were streaming down my face.

I could not move for some seconds, my mind too focused on the pleasure that I had been chasing for years. Then, the sparks became less and less intense until he slowed and his touches became too much. I parted my thighs and he moved his face away from me. I could see his face glistening with my juices and I could feel my thighs covered in them as well. He finally removed his fingers which were drenched in my juices as well.

He looked at me into my eyes and looked back his fingers,

"Taste yourself. You taste good."

He moved his fingers to my mouth and gently probed my mouth with them. I parted my lips and when he moved his fingers inside my mouth, I closed my mouth and began to suck. Not being too experienced, I remember my teeth grazing his fingers. I can imagine him thanking the Gods for not letting me suck him at that time.

I was tasting myself for the first time and I liked it. I tasted pretty good, almost tasteless with a slight tang to it. I could see him, admiring me while I sucked his fingers clean.

He eventually pulled away and sat back, still looking at me. I felt how uncertain he was, I guess he was unsure about the outcome of our actions, but I did not want him to stop. Not when I was so close to my goal. In order to encourage him, I propped myself up and kissed him.

"It's okay, you know? I want this. I promise nothing's gonna change after this alright, G?"

He kissed me back and nodded, but he looked as if he could not believe what was happening. He pushed me back onto the mattress and continued kissing me. I like to think that he was as nervous as I was.

He got back on his knees, spat in his hand and started stroking his hard cock. From my position his cock seemed thick, almost thicker than my wrist. I was worried about the pain that I was going to feel.