My First Time – first post by 'Nick' by throwaway99

A literotic sexstories: My First Time – first post by 'Nick' by throwaway99 ,
Losing my virginity to my best friend.
My First TimeCall me Nicolas, that way I keep some sort of anonymity. I’m 20, from London, England and I’m probably, definitely a sex addict. Not that i’m complaining though, I mean it’s great. To give a bit of context, I’m 6’4, very athletic and blessed down there, if you know what I mean. I didn’t know I was big, big until I had my first sexual experience. I was pretty young, 14 actually, and as you can imagine pretty horny constantly. I began masturbating younger than that, me and a friend of mine would go to his after school and jerk off to whatever we could find, pictures of celebrities and sometimes his older sister. I know, incredibly perverted, but we were kids. One thing I noticed at the time was that his cock looked bigger than mine, so I assumed mine wasn’t all that big. When I had my first sexual experience I realised I was wrong, very wrong.

My best friend Melissa is one of the sweetest, most caring and beautiful girls you’ll ever meet. I’ve loved her since we were kids, but for some reason we’ve always had this understanding that we couldn’t be together. When I think about her I think she’s the perfect girl but I just could never be with her. It’s weird but not worth wasting time debating I think. She also happened to be my next door neighbour growing up and in high school I would go over to her house to do homework. Her mum was a nurse so she would get home late, and her father wasn’t around so it would just be us. By 14, we would constantly hear about people in our year group who would fingering girls, getting blowjobs and having sex. Obviously upon reflection I realise all these kids were clearing lying but at that time you don’t know that, at least I didn’t. I hadn’t even had my first kiss and neither had Melissa. One time we were in her bedroom, watching something on TV and talking when we got onto the topic of masturbating. I asked her if she had ever tried it and she admitted to me that she had. The thought of her touching herself was enough to turn me on a bit, but when I asked what she would masturbate to, her answer made me harder than I’ve ever been in my entire life.

‘Honestly’ she said cautiously ‘You, Nick’.

I was shocked, I mean I would think about her every time I’d go home having spent the night revising with her so I was surprised that she would do the same. I told her this, to comfort her as I realised she was pretty embarrassed to admit it. She smiled, and laughed, and quietly whispered ‘thank you’ , still obviously embarrassed. She looked down and said abruptly ‘Nick, are you hard?’

In my state of surprise I didn’t realise my bulge was pushing against my joggers. I quickly scrambled to cover with my jumper, but Melissa put her hand on my arm and said ‘Wait, can I see it?’ Again I was shocked, but a sudden urge of confidence rained over me and I said ‘Sure, if you take your top off’.

I should mention even at this point, Melissa’s body was incredible. She was probably 5’2, slim build with a cute ass and the best set of tits in the year. Fantasizing about her has always been a guilty pleasure of mine. I found it rather exciting walking to school with her and her being unaware of the fact that the night before I was jerking off thinking about her sexy body. It’s worth mentioning that at this point I was probably 5’7 or 5’8 and skinny as piss.

She laughed at my request and blushed, and said ‘okay’. She took her top off to reveal her beautiful set of large tits, way too large for a girl that slim, held up in a lacy red bra. She licked her lips and ushered for me to take off my trousers, which I did happily. I rushed to take my joggers off when reality struck and my insecurities returned. I realised I was sitting there with a bulge I would consider small. I looked at my cock, feeling the pressure of an erection leave it, when I looked at Melissa, her mouth wide and a small amount of saliva dripping from the corner. ‘Wow’, she said, ‘That thing looks big’. I was taken aback by her comment, ‘How big is it’ she asked

‘I don’t know’ I responded

‘You don’t know, you’ve never measured it’ She asked bewildered

‘No I don’t think so’ I replied still stunned

She laughed at this ‘Guess we are going to find out then’. She got up and walked towards her schoolbag, picking up a 30cm ruler and bringing it back to the bed. She smiled and laid the ruler next to me. ‘Can I’ She began ‘Can I get your cock out please’. I nodded and she pulled down my boxers to reveal my incredibly hard cock. She raised the ruler to my dick and read out ‘7 inches’. I looked at her and asked ‘Okay, is that a good size?’. She smiled and replied ‘I think the average is 5 inches for fully grown men’. I don’t know why I had never measured up, I guess I didn’t wanna measure it to read out 3 or 4 inches even though it obviously wouldn’t have, but everyone at school would say they have huge cocks: 8 inches, 9 inches, 10 etc. I think it was at that moment I realised everyone who said stuff like that was clearly lying and, more importantly, I was blessed. 14 with a 7 inch cock sitting beside the hottest girl in the year with her tits practically out, ‘don’t mess this up’ I thought to myself as a sudden wave of confidence filled my body.

I turned to Melissa, looking from her beautiful hazel eyes to her soft pink lips, and finally down to her large breasts that sat there ideally. ‘Since you’ve seen my dick, can I see your tits’. She went slightly red in the face, looking down and touching her breasts in an attempt to hide them for a split second before looking up back at me. Again she smiled at me with her beautiful smile, ‘okay’ she said ‘that seems fair’. She released her red bra to reveal her 34D breasts. Instinctively, I reached out and grabbed them firmly and I felt precum leave my cock. Melissa reacted by grabbing my cock and stroking it. I was infatuated by my best friend’s tits, they were the sexiest things i’ve even seen with my own two eyes. I couldn’t draw my eyes away from them, but when I inevitably did, my eyes were drawn to hers; she was staring at me. I let my right hand go from her right breast and continued massaging the other with my hand and moved to her face. She continued wanking me off slowly, and we lent in and shared our first kiss.

As our lips separated, a sudden urge of sexual confidence ran through my body. She took off her trousers and I took off my shirt, we were finally fully naked. I slipped my right hand down her neck, past her tits towards her pussy. I knew very little about what to do when I got there so I winged it and used my porn knowledge to my advantage. Find the clit and play with it, I thought. I did such a thing, locating and fiddling the clit for a while whilst I kissed her and kissed her neck and she began wanking me off harder, her grip tightening around my hard cock. Eventually I lowered my hand and felt her wet pussy; she was practically dripping. I looked at her and she nodded her head, and I inserted my middle finger into her pussy and began fingerfucking her. She moaned in delight as I slowly fingered her tight pussy. My dick felt harder and harder and I knew I was soon to cum. I began fingering Melissa harder and harder, eventually shoving my index finger in there to make sure she was really getting off on it. She moaned and moaned before looking me dead in my eyes ‘Nick, I want you to fuck me’.

My hand couldn’t stop fingering her, but her question froze me inside. I couldn’t say, I didn’t want to say no but I was still surprised, I mean I shouldn’t have all things considered but I didn’t wake up that morning knowing I was going to lose my virginity. We didn’t have any condoms but I didn’t really know enough about sex education to care at this point. I smiled back at her, kissed her and removed my fingers from her cunt. I sat up and got in between her legs and lowered my body so that my cock sat on top of her stomach. My cock looked as if it would hit her belly button when inside, which got us both excited. I placed my left hand on her left leg and gripped my cock hard with my right hand, it was still dry but her pussy was dripping wet so I didn’t think it would be a problem. I slowly began pushing my cock into her wet pussy, she screamed as the tip broke the seal but encouraged me to keeping on going, her screams got louder with every inch, to the point where she covered her mouth with a pillow; no one else was home but my family lived right next door, if they heard her screaming we would be fucked. I inserted about 4 inches of cock inside her and began slowly fucking her with just that, thinking it might warm her up so that I can get the whole thing in. It worked, as within a minute or so I had got my entire 7 inch cock inside of her and i was fucking her. She began to cry, which made me want to stop. ‘Shit, are you okay’ I said to her, I was about to pull out my cock but she grabbed my hand ‘No, don’t stop I love it. Fuck me please’. With that my cock harden fully again and I began fucking her. At first slowly, her moans loud and right in my ear, but my sexual desire wanted, no needed, more and I began upping the tempo. My hard cock began pounding away at Melissa’s slim frame, her cries became louder but she kept encouraging me to fuck her harder. It felt like I had been possessed by some sex crazed demon as I lifted myself from Melissa’s grasp and grabbed her neck with my hands, choking her. She whimpered ‘Yes daddy, i’m cumming daddy’ and I felt her first orgasm on my massive cock. I kept up like this for a while, giving her time to breathe every now and again but for the most part choking her and she came again.

She whimpered as I pulled my cock out and turned her around, exposing her cute ass in the doggy style position. The temptation to destroy her asshole was there, but ultimately I decided against it, instead I rammed my cock inside her cunt again, fucking her senseless and pulling her hair making her cry, but her seductive moans were enough to confirm to me she was loving every second of this violent fuck. I let go of her hair and reached around and grabbed her neck, pulling her closer to me. With one hand I choked her and the other I molested her big tits. I began to whisper sweet nothings in her ear, demanding she was all mine now and I only I could fuck her, saying she had to best tits i’ve ever seen and so on, all the while brutally fucking her tight little virgin cunt. I felt the sensation of my cock about to cum so I let her go from my embrace, pulled out and came all over her ass.

We laid there for a moment, not really saying anything. I got up abruptly and got dressed, heading back home where my parents greeted me, asked about my day and if I had done anything fun, for which I told them it was pretty standard. I rushed to my bathroom to run myself a shower, where I observed and admired my large cock length in the mirror. My phone buzzed, disrupting the music that had been playing and I went to see who it was. It was Melissa. My mind quickly went to the worst case scenarios, she was upset that I had gone too hard, she didn’t like being choked or she was going to tell everyone at school that I was bad and embarrass me. I was shook, but I opened the message, expecting the worst. ‘Thanks for tonight, you walking tomorrow?’ It read. I replied ‘No problem, and yeah see you tomorrow’ to which she replied with a smiley face. I wanked off in the shower, and headed to bed, but before I fell asleep I had an idea. I looked at the books I had purchased for school and I found a black book, completely empty with nothing but blank lined pages. I took a pen and wrote down as my first entrant, ‘Melissa’ and the date. I don’t know what impulsed me to do this, other than having seen it on a TV show I think, where a popular ladies man keeps a list of all the women he has slept with. I suppose I was envious and I wanted my own, and not to mention I wanted to fuck a lot more.

I spoke to Melissa the day after on our way to school. We decided to keep it a secret that we had fucked because it would damage Melissa’s reputation, I mean I was popular so it wasn’t like the had fucked some tramp or druggy, but the fact she wasn’t a virgin meant girls would call her a slut and boys would think they could fuck her to, which Melissa didn’t want. I was fine with keeping it a secret to, I didn’t want to be like one of those lads who go around saying how many girls they’ve fucked but everyone knows they are lying and they just end up looking like wetwipes. We also agreed not to make a big deal about the fact we had fucked, but to be friends with benefits. Considering how horny we both were, and considering I would go to her house 3 times a week after school anyway, it meant we would have sex a lot. At first it was weird, but it quickly became the new norm for us both. We would be best friends in school, no flirting or anything like that but not repressing anything at the same time, and then when we went back to hers to ‘study’, we’d have lots of sex.