Hey, this is my first story, and its a kind of a true story. Basically after my first break-up, it’s the story of a friend who helped me get over it. Hope you like it.
It was around the time Summer becomes Autumn in 2010 and I was only 16. I had my very first girlfriend and I was very pleased with how we were going. We had hit the 3 month mark, and I was elated, I couldn’t comprehend our relationship going any better. Evidently, she could.
Pheobe dumped me on a Thursday, during the lunch break at school. I was devastated. I found myself questioning how this could happen, what went wrong, what could I have done. As you do. In the face of these questions, she responded with, “I think we should just be friends.” I can tell you, there are no crueller words to say to a horny 16 year old boy. As she pranced away from our brief break-up talk and I felt the weight of the world crashing down on me, the bell rang, signalling classes to resume. It’s a strange feeling, taking the biggest blow to your self-esteem to date and then having to immediately go to Mrs. Johanson’s English class. Tell me if you can relate.
Going through your first break up is a totally unique experience of emotion and insecurity. You have moments where you think it’s the end of the world. There are moments when you find yourself angry at her, for even being alive. There are moments when you think it’s a good thing, that now you can have any woman you want. There are moments when you realise that you can’t have any woman that you want, and that finding another is probably impossible. These are followed up by moments that you realise that yes, finding another woman is definitely going to be impossible. But the thought that entered my mind the most was that she was over me, and I wasn’t over her.
I had to see Pheobe everyday at school. Philmore High is a big school, you’d think I’d be able to avoid her, but we shared many of the same friends, so she was always just kind of… there. And every time I saw her, I saw all of her. I saw her cute button nose and the little patch of freckles dotted around it. I saw her deep, brown eyes, full of character and rich in beauty. I saw her long, flowing hair, a glowing shade of auburn. I saw her sexy, dark skin tone. I saw her cute, a-cup titties. And I saw her ass. The sexiest, roundest, bubbliest ass you will ever see on a 16 year old girl, and I fell in love with her all over again.
Being around her was agony. I realise now how melodramatic it all was, but then, you always realise that you’ve embarrassed yourself after it’s already happened. Anyways, being around her was agony. I confided in a lot of people my heart-felled emotions on the subject. I imagine they grew weary of it quickly, but I kept coming back to them with more.
My favourite confidants were female. My guy friends were just growing into their sense of humours, whenever I would come to any of them for advice or whatever, they would aptly say, “Let me just stop you there,” and just walk away. I didn’t care much for that joke. But Joanne would listen. As would Bella. And Rachael and Nicole. They all gave me the same advice. That I had a lot of pent up emotion and sexual tension and I some how needed to relieve that. Little did they know, that this sexual tension would inevitably be taken out on one of them
I didn’t take heed of their advice, at first. The girls told me that I must let out my pent up emotion, but I was determined to not let my emotions get the better of me. In hindsight, I suppose I should have. Perhaps I should have let the misery take hold of me, and then I would be able to let go. Instead, I became bound to a very subdued, mediocre mood for the next two months.
As such, I became lethargic. No longer did sports or anything of an active nature. My friends could only seem to drag me out to movies and stuff of a similar nature, because I thought I would bring them down if it were anything more. It was about two months later, that a couple friends decided to do a little LOST marathon at my house. LOST was a weird show, and there were a few of us who took pleasure in getting together now and then and making merciless fun of it.
It was a mild day, and a group of four of us got round to watch it. Besides me, there were two other guys, and a girl: Jade. We watched about 4 or 5 episodes of it, which was about as much as four restless teenagers could bare. We hurled abuse at characters and condemned the writers. Despite my state, I did have a lot of fun. But as the day got later, the guy who brought the DVD’s had to go and do some last minute revision for a test he had the next day.
After this, the three of us talked briefly. Jade and Rob asked me how I was doing since the break-up, and I replied, “Never better” with a weak smile, as I always did.
Not long after, the two proceeded to wrestle briefly. Jade was very sexually charged, she was the only one in our little group who had actually had sex. Rob and Jade had an off and on relationship. Though they had never had sex, they definitely had some kind of chemistry. Their fire had been cooling though, ever since Jade had been exploring her sexuality with other guys. Despite himself, Rob was a very innocent kid and Jade was a little too much woman for him.
As they wrestled, I got a chance to check Jade out for myself. Jade, though an extremely nice girl was a renowned slut, and the thought of her shaking her cute little body over some guys’ dick had given me countless boners. Jade had nice long legs, and a cute little ass, that were wrapped up nicely in a white pair of skinny jeans. She wore a loose top, that when hanging low, would allow me to see part of her bra and her cleavage. Jade had incredible tits, big C- cups which were fantastic for her age. Jade had short, light brown hair, just a little shorter then shoulder length and her normally curly hair had been straightened, and it hung over her face very seductively.
Eventually, Rob had to leave, as he had clearly gotten a boner that he didn’t want Jade to see it. Jade did see and she laughed loudly as soon as he had shut the door behind him. She then turned and smiled at me, and I smiled back and crossed my legs, trying to conceal the fact that I too, had gotten a boner.
Jade was still laying on the floor, breathing heavily after the wrestling and I watched her great breasts heaving. As I stared and my cock grew larger in my pants, Jade pretended to be oblivious to the way my eyes were curling around her hot body. She got up and sat just across from me and looked into my eyes.
“Are you sure you’re okay? Since the break-up with Pheobe?” she asked sympathetically.
Though my eyes feasted hungrily on Jade’s body, her every curve, filling my member with more blood, my brain warned me that she was trying to be serious with me, and I reluctantly looked up to meet her eyes.
“I’m trying to be okay.” I said, honestly. “ But sometimes it’s a little hard…”
Without saying anything, Jade gave me a sympathetic smile and touched my leg. Inspired by Rob from before, I playfully grabbed her hand and pulled her towards me, and pretty soon, Jade and I were wrestling just as she and Rob had been earlier.
As we fought, I brushed my hands by her breasts and her ass and she brushed my dick with her hands a couple times too. Eventually, I pinned her down, grabbing both her wrists and laying her on the ground. As she hit the ground, her loose shirt fell beneath her chest, and I saw her entire bra. It was sexy, lacy bra, mainly orange and black. The colours mingled seductively over her huge tits, and inbetween her large breasts, there was a tiny black ribbon placed on the bridge of the bra.
Without thinking, I said, “Nice bra,” and was immediately embarrassed. Jade giggled encouraging though, and said, “Thanks. I can give you a better look if you want.” Without waiting for my reply, she rolled me on my back, she perched herself over my crotch and took off her shirt, nice and slowly. I watched her big tits, not saying anything, not believing my luck.
Jade smiled, and lowered herself onto me so that my head was inbetween her breasts. They were soft and warm and my dick began to feel like it was going to burst from my pants. Just then, she lowered herself lower still, so that our crotches were touching and she let out a small gasp of surprise as she felt my throbbing cock against her.
I apologised quickly, but then smiled cheekily and told her she couldn’t really blame me for being hard right now. Jade sat up, and smiled smugly down at me and said, “Baby, men get hard exactly when I want them to, and for you, that was about 10 minutes ago.”
I was at a loss for words, as I was legitimately unaware she even knew that I was hard, let alone that she was actively trying to get me that way. But before I could respond, Jade reached behind her and unstrapped her bra, and her naked breasts burst forward. They were large, perky with big brown nipples perfectly placed in the centre of each of them.
As I was still taking them in, she grabbed my shirt and started to pull me, as she rolled onto her back so that now I was on top of her. She then stroked my arm, and pulled my hand gently so that it rested on her bare breast. These were the first and best breasts I had ever gotten the privilege to touch, and I took full advantage of this brand new experience. I stroked it gently to begin with and then cupped it and caressed and massaged it. They were soft and smooth, juicy, firm, perky and full of life. As my hand enjoyed her right breast, I leaned over to kiss and suck at her other nipple. It was soft and sensitive and Jade squeaked softly as I danced my tongue over it lovingly.
Jade’s breathing increased to a slight pant. After a minute, inbetween breaths, she whispered, kiss me. I moved my left hand over her left breast, and she moved her hands over mine, and I kissed my way gently up her neck til I reached her soft, supple lips. Our lips mingled shyly at first, but as our tongues got involved, our confidence and passions grew.
As our lips and tongues locked, and all four of our hands helped caress her sensitive bosom, I lowered myself onto her a little further so that my hard cock touched her leg, and I began to dry hump her. As I began to do this, she smiled widely, and she could no longer kiss back, so I moved my lips to her neck as she began to moan softly.
As if unable to bare any longer that her hands weren’t around my cock, she pushed me off her gently so that I was sitting down, and then began to rub my dick through my jeans. Though this feeling was better then than any I had experienced before, and I did not want to interrupt this, there was a question I had to ask.
“Why are you being so good to me?” I asked
Jade smiled, her eyes still fixed on my crotch. “Because you deserve it,” she smiled. “You’ve had a rough couple of months, and I just wanted to make you feel good again. Besides, surely you’ve noticed I’ve had a bit of a crush on you for a while now.”
I was a little taken aback by this. “Me? Really? I thought you had a thing for Rob.”
“Rob is just a boy, and I know now that you are a man,” she said, while still stroking my dick through my pants and eyeing it greedily. I kissed her on the forehead softly, and she looked up so that our lips could meet. We kissed briefly, and then she reluctantly pulled away. She then grinned at me and told me to go sit on the couch. I did as I was told, and she followed. As I sat, she got on her knees before me and resumed rubbing my dick. She looked up at me and asked if she could take it out of my pants. I complied without hesitation.
She removed my cock from my pants and held it at its base, admiring it as she rubbed the base gently. She then began to salivate and made a move to put it in her mouth, but then thought better of it and looked up at me as if asking for permission. I nodded my head enthusiastically, and she smiled softly.
She clearly wanted to savour the moment, she began to rub a little more vigorously as she thought about the best way to enjoy my cock. She then decided to give it a little lick, right near the head, and as she touched me with her tongue, it felt like ecstasy. She followed that with a few more gentle licks, like a cat lapping up its milk. My dick began pulsating wildly, and she grinned at her handywork. She then looked up, and saw the anticipation in my face. Then she decided to finally put it in her mouth.
She opened her mouth wide and her tongue slightly poking out. She touched the head with her tongue first and then wrapped her lips around it and she pushed herself down onto my shaft as I watched my dick disappear into her mouth. She moved slowly at first, gently rolling her lips up and down my shaft, but then the movements of her head and neck became more exaggerated as she rocked my cock deeper into her mouth. And then she started using her well trained tongue, first to flick against the bottom of my cock, and then she began to curl it around me.
I didn’t think it could get any better when she began to suck. Her saliva swirled around me as the intense pressure on my dick intensified further. Experiencing uncontrollable pleasure, I began to pant, as she moaned soothingly.
She then began to cradle and gently squeeze my balls, and she pushed herself down on my cock, so that I felt the tip of my cock against her tender throat. Jade must have known that this was my first blow job, and she threw everything at me to make sure it was an unbeatable experience.
Being a virgin, I wasn’t going to be able to hold out long in the face of a dick sucking pro. I felt myself starting to cum and I began to warn Jade of what was to come. But Jade was attached to my cock. She continued slurping on my dick and squeezed my balls a little tighter to signal to me that she was ready.
Without hesitation, I ejaculated deep in her mouth, and she gulped down the cum happily. She continued sucking and licking, decreasing her intensity, until she knew she had sucked me dry. She swallowed what remained in her mouth and pulled herself unwillingly off my cock. She then proceeded to gently kiss my tender penis and then looked up and beamed at me.
I was exhausted, but I still managed to greet her face warmly with a long, passionate kiss. Jade knew that after that, I wouldn’t be able to stand up again for a while, so she collected her things, put back on her shirt but leaving the bra as a little gift for me. She then come back over to me, gave my cock another gentle kiss and then tucked it back into my pants. She then smiled at me and whispered in my ear, “Let’s do this again… If you can handle it.” She then placed her bra over my lap, and left without another word.
I felt like chasing after her, asking her to spend the night, but I was well aware my legs would give out if I tried to get up. Instead, I leaned back into my chair and picked up her bra. As I stared at it, I told myself, next time, I’m fucking her.
That next week, every time I tried to talk to her about the blowjob or the possibility of a next one, she would smile slyly and say that it would happen in good time. It wasn’t til one Friday night, two weeks from that night that it came up again. We were chatting on facebook and I mentioned to her that my parents and my sister would be out of the house all day on the Saturday, to which she aptly responded with, “When should I come over?”
I grinned widely. I maintained an air of causality though, and responded with, “How about 12?”
Jade didn’t miss a beat. She responded within seconds with, “I’ll bring the condoms.” My dick sprang to life at those words, but before I had a chance to reply, she went offline.
I went to bed early that night, pulling my dick and dreaming of what was to come tomorrow.
* * *
I paced behind my front door. I was impatiently waiting for her to come. It was 12.14pm. Every minute that morning sank by as slowly as an hour and since 12 every minute had been like a day. I was nervous about losing my virginity, excited to be able to have sex, anxious for her to come. A lot of emotions were going through my head. I almost didn’t notice when she knocked on the door. But once I saw her silhouette through the glass door, I sprang for it. As I opened it she smiled at me and walked in coolly.
As she walked in, my mouth fell open as I took in how she looked. Her hair had been grown out a bit, and styled sexier than I’ve ever seen it. It was a little wavy, and it sailed down to her chest. Her breasts were more perfect then ever, with a sexy little slit of cleavage creeping out of her tight, black tube top that held her breasts together so nicely. She wore a short, black skirt that fell loosely over an ass that never looked so good. She wore dark stockings that wrapped around her powerful legs and lead down to a black pair of high heels.
My dick jumped at the sight of her. “You like?” she asked, cutely. Her pink lipstick shone as her lips moved. I slowly walked over to her and kissed her passionately on the mouth. She kissed back too, desperately trying to match my enthusiasm. My hands fell to her ass and I clutched onto her sweet behind as I pulled her closer. Our tounges locked and our bodies drew closer when suddenly she stopped and pushed me softly.
She waited to speak as she enjoyed the anticipation in my eyes. “How about we take this to your bedroom?” She didn’t wait for me to respond, she just put a pack of condoms in my hands and then walked off to my bedroom.
I allowed myself just a minute to thank myself for the position I’d gotten myself in before following her. When I walked into my bedroom, I could see that Jade had already taken off her heels and stockings and her tanned legs were crossed and pointed in my direction. She gazed at me and bit her lower lip. I moved towards her, fell to my knees and started kissing her leg. I kissed and licked my way up her long, shapely legs til I reached the inner thigh of her left leg. Then, she started to spread her legs, just enough so that I could get my first glimpse of her panties. Not surprisingly, they were black.
I continued to lovingly kiss and lick and suck at her thighs until she spread her legs a little more, then I dived at her pussy. I kissed and licked the front of her panties with renewed vigour, and Jade giggled with anticipation. I continued to do so until I felt her panties get a little damp, and I knew it wasn’t just my saliva doing that. I then glazed my way up each leg with my hands til I found her panties, and I slowly slid them off.
I then returned to her pussy. It was bald and dripping and oh so sexy. I thirstily scooped her juices in my mouth and then kissed and licked her, forcing my tongue in further every second. She started to pant and as I started to get my fingers involved she began to moan. Soon, she wrapped her legs around my neck and started to push my face deep into her vagina. Eventually, it became too much enticement to bear and I broke away from her pussy and stood above her.
On the bed, she fumbled for the box of condoms and we both hurriedly took one out and opened its wrapper. I then speedily took of my shirt, and Jade began to kiss my chest passionately as I removed my pants. Then, we both helped roll the condom onto my now rock hard dick and then Jade grabbed my cock, began to lay back as she guided me to her pussy. The moment felt surreal. I felt like I was about to throw up as she rested the head of my cock against her pussy lips. I looked into her face and she smiled warmly.
I pushed myself into her. For a moment, I didn’t even move. I just gaped as I experienced the most incredible feeling ever. A tight, warm pussy was wrapped around my tender cock. I slowly began to rock my self, gradually, out then in, in then out. Jade squeaked a little as she watched my dick slide further and further inside her. I started going harder and faster. Jade started rocking her hips in sync with my dick ramming her. Her face was all pleasure and the sight oh it made me cum. It was the most explosive ejaculation I’d ever had and Jade laughed as she felt the throbbing inside of her. I felt incredible. I collapsed on top of her, panting and out of breath.
When I started to regain my breath, I said to her, “Thank you. That was the best feeling I’ve ever had.”
Jade then flipped me on my back and smiled down on me mischievously. “Oh no,” she said, laughing a little. “You’re not done yet. Why did you think I bought the 12 pack of condoms?”
I grinned back up at her and slid her tongue into my mouth. We kissed, passionately, and she moved her hand down to massage my tender cock. With skilled hands like hers, and with her hot body on top of me, it wasn’t long before I was hard again.
Jade dived for the condoms. She slid one of them over my cock and then got on her knees and hovered above me. She swayed her hips, nice and slowly just above my pelvis and stared deep into my eyes, being the little cock-tease that she is. She then lowered herself onto me, steadying my cock with her hands as she let it glide into her pussy. She then rested her hands on my chest and started to roll her hips on top of me. She panted slightly, her eyes closed and her chin pointed straight ahead, concentrating on the feeling inside of her.
As Jade rode my cock, I grabbed her nice little ass, and helped her rock herself on my dick. My dick was hard, yet fragile and sensitive to her every movement, making the pleasure all the more extreme. I felt like id be able to last a little longer this time, so I figured I might try experimenting with the positions.
I grabbed her waist, then rolled myself on top, and Jade yelped excitedly as she knew I was taking control now. I reluctantly slid my cock out of her pussy, then flipped her on her chest and started pulling her waist upwards and towards me. She knew what I wanted, and that was doggy style.
On her hands and knees, she smiled over her shoulder and looked back and watched as slowly began to push myself into her pussy, that felt even tighter than before. I pushed all the way in, and just let myself rest inside her, her pussy wrapped tighter around me than ever before. I then stated fucking her, and then started to absolutely slam her pussy, wanting to cum more than ever before, and Jade started moaning with pleasure.
I fucked her hard, and she started to cum all over my dick. As her orgasm died down, mine started, and I pulled out of her, took off the condom, flipped her back on her back and jacked myself off over her. A big, huge load all over her stomach, some of which she scooped up and put in her mouth.
Jade and I ended up using another 3 of those 12 condoms that day. We were both exhausted, and couldn’t fuck one minute more. She showered and then got dressed, and left me the box of condoms with 7 remaining. On her way out of the door, she said that she assumed id find a use for them soon, with a wink. I looked forward to being able to do this again her, but at school on Monday she assured me it never will, and it had to be a one off thing. So instead, resolved to look forward to the next girl id get to sleep with…