It was Early Summer (Christmas Edition)

It was early summer, I mean really early summer, as in it had only been summer for a few days, early June-ish. Anyway, it was early summer, I was eighteen but still in high school and living with my parents. I still didn’t have a car and my cell phone was shit, so my contact with the outside world was very limited, luckily these limitations did not, however, prevent me from having a great deal of friends. Indeed, I am a very likable person, and I am not being cocky or presumptuous when I say that either, it is simply a fact. People seem to be drawn to me, nerds, popular kids, assholes, white trash, emo kids, those kids you never knew existed until they started hanging around you, gangbangers, honor students, you name it and I’ll bet you twenty three and a half dollars (That’s as much as I have at the moment) that at least one member of the group you name will consider his/her self my friend.

Sadly, I’m the kind of person that chicks dig but, you know, not in a romantic way. I have so many bros who are women you would not believe; every single one of them I dated for about six minutes before they decided that they preferred just being “Friends.” And you know what? I do it. Most guys when they hear “Just friends” say “yeah whatever,” then leave forever, but me, I keep up with them, texting, talking, going out for coffee, playing video games, cigarettes, friend stuff. And I’m not going to tell you that I’m totally ok with this, because it kind of really pisses me off, but honestly until “she” came into my life I didn’t care nearly as much. Her name was Allison, and I’ll be damned if she wasn’t the most beautiful person I had ever seen, and although she was a college freshman she was only a year older than I was (she had skipped fifth grade). She was attending college in my area, and we would run into each other in town, on the streets, in restaurants, and whenever we would run into each other, she would talk, I would laugh and nod accordingly, then I would talk a bit, and HOLY FUCK was I happy, elated in fact. Just talking to her made me sweat, she was just so smart and funny and beautiful. And despite the fact that I wanted to be her best friend with all my heart, the last thing I wanted to be was JUST her friend, because despite all the perks of friendship, often times there are things that one simply does not do with friends. Kissing for example, sure, maybe a kiss or two on the cheek after not seeing one another for a long period of time, but on the lips? I think not. Blowjobs are an even better example; go ask your girlfriend for a blowjob, (if you have one) there’s a damn better chance of actually getting one from her than if you ask your best friend to give you one, “Hey Billy, blow me!” “Fuck off, stupid cunt!” See, what did I tell you? Maybe if your BFF is a girl then you might have a better chance, but still, my point is that it is not proper for friends to interact sexually. It is just not done.

So now you can see why it mattered so much that this relationship between Allison and I amount to something greater than friendship. And I would have my chance to make this happen, as soon a school let out.

You see, my parents and my younger sister were leaving on an all expenses paid, month long trip to London starting on the first of July. Yeah, you know how Tops does that Monopoly thing every year where you put the ticket thingies on the little Monopoly board they give you? Well last year my family won the grand prize, three tickets to London, England where they would stay at a five star hotel for free for four whole weeks, along with five thousand dollars of spending money. Sounds absolutely fantabulous, right? Right, but there were only three tickets, remember?

So me and my father flipped a coin to see who would go, (My mother and my sister already had guaranteed spots because my mother was absolutely heart set on going, and plus she was the one who had found Park Place, anyway, so there was no way she was getting left behind. And my sister is eleven, if she got left behind she would flip the fuck out, I mean like AHHHHHHHHHHHOLYFUCKINGSHITANDEEEEEEEEKKKKKKKKK, the stuff that mental breakdowns are made of). So it was me and pops left, and that rat bastard called heads… Do you know which side gazed skyward that day? Heads, fucking heads. Hence it was declared that twas I who would be left ashore as my family sailed first class through the skies towards European Paradise.

At first I thought it would be ok, be home alone for a whole month, smoke inside, throw a couple parties, invite all my friends, get my dealer to hook me up with a shitload of booze, maybe even invite Allison over… All of a sudden I didn’t feel so bad about being left behind. Then, my mother and father decided that it would be best if I was looked after by a responsible adult while they were away. So they took my key, and after a great deal of research they called Ms. Panermen.

Now, let me give you a bit of background information on Ms. P, Ms. P is my high school science teacher, although she doesn’t have to be. A few years ago her husband won the lottery, receiving a grand total of eight million dollars. Two months after he did this, Ms. P filed for a divorce, effectively taking four million dollars from her husband. Sadly though, in the process her husband won their children, who then immigrated to Tahiti. So Ms. P was left a very rich woman with a hole in her heart where children had been. So she became a high school science teacher and took up babysitting. Ms. Panermen is about 34 years old and is, in my book, a rather attractive woman, with dark hair falling just below her shoulders and lips that could only be described as luscious, along with sumptuous portions in the places that really count. She is also a fun person to be around and in a way, reminds me a little of Allison, a little.

You see, I have no personal quarrel with Ms. P, we are friends and honestly I would be kind of really pumped to stay at her place for a month if it weren’t for the fact that I had already made plans. So I begged my parents to allow me to stay by myself, I promised I would behave but they would have none of it. I was to stay with Ms. P and that was that.

So they left and I stayed, and pretty much I spent the entire first week smoking cigarettes with my friends under the highway over pass. It was chill, but we could have been partying at my place with a few six packs and a few games of Candy Land (Candy Land is the bomb, Queen Frosteen, bitch!) or maybe even making my move on Allison, who knows? All I know is that it could have been a shitload better than it was.

But you know what? I will give Ms. P some credit (By then we were on a first name basis, so I was calling her Charlotte) she was really making an effort to make me feel at home, she let me come and go as I pleased, she bought me all the foods I liked, and even knit me a blanket, but I think she sensed that I was unhappy. So one late evening, I was actually feeling pretty happy because I had spent the afternoon with Allison, I had asked her out on a formal date and she had said she said yes! Anyway, Charlotte approached me and said “Hey, Billy… I’ve noticed kind of down in the dumps lately…”

I smiled and looked up, not fully interpreting what she had said, “What?” I asked dumbly, my eyes glazed over in a euphoric haze.

“Billy?” She asked, concerned, “are you alright?”

“Sensing her concern I forced myself down from the clouds and back into her living room, “Hum…? Yes, of course!” I declared as I brushed away the few clouds still lingered above my head, “What makes you say that?”

“You seemed a little, out of it.” She chuckled.

What she did next was the most unexpected thing… EVER. She leaned in and kissed me, right on the mouth. At first I was too surprised to do anything, and she was so warm and soft…

Then I remembered Allison, we had a date! God this is so fucked up! I remember thinking right before I pulled away from her embrace. “Charlotte, what the FUCK?!?” I shouted, now confused and a little angry.

“It’s okay,” She assured me, “I’m just trying to cheer you up a bit”

“What? Why… With this… lips…Huh! What?” I began babbling, I may have been overreacting a bit but, at the time it seemed as if reality was beginning to crumble around me. “No No No, this is really fucking fucked up. What is going on?”

“Billy, don’t fight it, I just want to help…” She said, looking at me with such a look that I could tell that she really did care, and I know this is weird but let me tell you, I’ve always been able to read people pretty well and, well, in that moment her gaze conveyed such a feeling of love, hot passionate love, that I realized I was being a bit overdramatic.

“I’m sorry, Charlotte, it’s just that you surprised me” I told her, inhaling deeply, making a desperate attempt to take hold of my nerves, “It’s okay”

Charlotte sighed, licked her lips and sat down next to me, “I’m sorry Bill, it’s just…” she trailed off.

“Just what?” I asked her, this was obviously not just about me.

She Sniffed loudly, as if she were about to cry, I could see that she wanted to, now. “It’s just…” she let out a small sob, “I’ve been so lonely!” This is when all hell broke loose, soon my science teacher was nestled into my shoulder, letting loose tears in torrents. “It’s just… You seemed so (sob) sad.” She cried, “I thought if I tried to please you with my body, you might cheer up.”

“Oh, Charlotte,” I said, chuckling, “First, we’re not inside a fifteen year old boy’s sex fantasy so that will not be necessary, second thing is, I haven’t been sad, I’ve just had a lot of things on my mind is all” God was that really fucking hard to say. Do you know what it is like to have the sex drive of an eighteen year old boy and turn down sex with someone you desperately want to sex with? It’s nearly fucking impossible. The only thing that was keeping me from pushing that fine woman onto her hands and knees and fucking her from behind till she passes out was Allison.

“God, Billy, you’re such a good person” she said, lifting her head from my shoulder too wipe her tears, “Anybody else would’ve just taken the opportunity and fucked me silly…Wait… You’re not gay are you?” Oh my fucking shit, what the FUCK??!?!?! I screamed so loud in my head that I was sure she could hear, but I kept my face calm and my voice firm,

“No, of course not, what kind of question is that?” I asked her, making a light smile and laughing dryly.

She giggled, “I just thought I’d ask” she said, her tears where beginning to dry now and I was glad, “Please, just kiss me, this is for me now…”

Whoa, not sure what to tell her, I have a girlfriend? But I don’t, yet and I’ve never been much of a liar, repressing all the fucked up shit in my head is easy, but when it comes to telling outright lies I’m no good. FUCK! I was going to have to do it, man I wanted to do it, more than anything I wanted to do it, FINE! “Ok,” I said then leaned in, her breath smelled sweet, comparable to rose petals. I felt her dark hair against my skin, it gave me chills it was so soft.

She closed her eyes as our lips met, again so warm and soft… She moaned quietly, I couldn’t help it. I slipped my tongue past my lips, past hers and into her mouth so it hugged hers. Her eyes opened for a second, as if to protest, but realizing that this was her chance she embraced the moment and slipped hers into mine.

It felt as though my body was not my own, my mind screamed in agony as the guilt of this act consumed me, against my parents, my best friend, the girl I love, damn.

Sadly this was only fuel for my body; soon my arms reached under her blouse and began caressing those beautiful mounds of flesh which sat proudly atop her chest. I could feel the lace of her bra under my fingers, her lips on mine. I wanted this. Fuck did I want this! She began to unbutton my shirt… and my mind gave way. This was it, I suddenly leaned harder into her kisses, my hands flew as they undid the latch of her bra and she pulled away, just for a moment to remove her blouse, and as soon as it was off my lips flew to hers again and my hands leapt to her chest. Her nipples were hard as rock and I began to alternate rubbing her nipples between my thumb and for finger. She pulled away from my lips just to let out a loud moan, a great earth shattering moan.

“Billy!” She exclaimed, lifting her head towards the ceiling, “More!” She shouted, my mouth moved to her breasts, my tongue licking and stroking each of her nipples passionately. But I did not linger, for I had something much greater in mind.

I undid the button on her skirt and pulled it away, revealing a pair of pink panties, I leaned in and placed a single kiss on it, her body seemed to vibrate, and such was the energy her pleasure was releasing. She gasped as I slowly began to slide her panties down her thighs, past her ankles, the finally past her small bare feet.

When I looked up I almost went mad, I wanted to take it then and there, but even though my mind was clouded by these sexual acts I still knew that it wasn’t quite time yet, there was still much to do. My head was now buried between her legs; it was trim, hot, and beautiful. I laid my mouth on her burning hot pussy and began to run my tongue along the lips of her pussy.

“AHHhhhhhhhhh!!” She piped as I slipped my tongue inside, testing the waters, if you will. I removed my tongue and raised my head about an inch and a half, right on the level with her clitoris which was now clearly visible, round and red I began to massage it with my tongue. Then in a move so fast it was barely visible I moved my hand from its resting place on her bulbous bosom and slipped three fingers into her hungry pussy. “Billy, don’t stop!” She cried, and I wasn’t about to. I began to slide my fingers in and out. Inside it was like her mouth had been, warm and moist and soft, but different in a sense that is almost impossible to describe, if you’ve ever been inside a vagina you know what I’m talking about, that feeling you try desperately to put into words  but ultimately fail in the end. A mixture of joy and lust and purity and guilt and trust and love and just every emotion in between put into one euphoric feeling.

I moved my other hand to where I was, licked it, located her tight little bud and slowly pushed my finger inside. “FUUUUUCCCKK” she screamed, “I’m gonna come!” That had done it; I pulled it out and focused all my energy into her pussy. I could feel her tunnels constrict as she began to orgasm but that did not stop me, I continued on even harder than before, “Aa-aa-aHhhhhheeee” She screamed as she had one orgasm after another until finally she there exhausted.

“Wow, Billy. I never came like that before,” she gasped “But now it’s your turn.” She sat up and peered at my cock which was standing hard and tall, hungry for pleasure. I sprawled out on the couch, and there between my legs sat my gorgeous science teacher, completely naked, my dick firmly grasped in her small hands.

She too started with a single kiss, a single kiss on the head of my dick and involuntarily my body shook with anticipation. She started slow, her lips pursed as she began to move her mouth up and down my dick; her tongue seemed to be magic, caressing all the right places. She began to go deeper and deeper; I could feel myself inside her throat. I held it as long as I could, but I still came sooner than I would have liked. My hot milk poured itself into her mouth and she swallowed every bit of it. Wow I thought as she began to lick up the remaining drops of semen that still lingered on my dick.

She stood up, I stood up, I laid on the couch, she laid spooned up against me. Together we laid there, just her and me, we talked some, but mostly we just lay there feeling each other, being there with each other. The guilt did not return as I thought it would. Tomorrow was tomorrow, today is today. In those moments it seemed like there was nothing more in the world than Charlotte and I.

Then she said, “Ready for round two?”

“Yes!” I chuckled; I was ready for this, ready for her. “Do you have any condoms?” I asked. All I heard was “SHIT!” then some angry mumbling, “Ha!” I laughed, “I have one, don’t worry” I said picking up my pants and removing my wallet.

“Phew!”  She exhaled “That was close” I pulled the condom out of my wallet. It was an old latex Trojan, I had been carrying it around since I was twelve. Time for your moment of glory, my old friend I thought, smiling at it. Wow, VAGINAL SEX. I’ll be honest with you; this is my first time having actual sex. Sure I’ve gotten blowjobs and hand jobs and junk, but this is the first time it’s for real. I took a deep breath, then said,

“Shall we adjourn to the bedroom my dear?” She nodded and pointed down a short little hallway. We walked down it, hand in hand. When we began to near the end of the hallway, she unclasped her hand and rushed ahead and began to knock on the door. “What’s going on?” I asked her,

“Look,” she said, and opened the door. There she was, seemingly glowing in the dim light; more beautiful than I had ever imagined, every bit of her was visible.

“Allison?” I asked, “Is that you” She nodded, and I ran to her arms outstretched. “How did you get here?”

“Charlotte told me about you, and how much you really care about me. No man has ever cared that much about me before.” She said. I felt a pang of guilt as I realized that the real reason I had entered the bedroom was to fuck another woman. Fuck, fuck fuck fuckity fuck fuck fuck. Now I gotta tell the FUCKING truth!

“Allison, what about Charlotte and I? You’re not offended?”

“Of course not, silly!” She laughed, “You did not know I was here, you did not know that I really wanted you, and anyway, I’d rather just join you two!” With this she jumped on the bed and beckoned us forward.

I walked slowly, as if in a dream, a dream in which if I moved too fast I would wake up and lose it forever. More beautiful than anything she sat there, the light glancing of her breast just so, made it seem as though they were alight, like some holy objects able to grant eternal life and more. I reached the bed and she looked up at me, “This might be a bit soon, but I think I love you” I told her, “From the moment I met you I knew. You’re the most wonderful thing on this earth, Allison.” I turned to Charlotte, “You’re number two Charlotte!” I exclaimed, she began to fake pout and we all laughed.

I crawled onto the bed, kissing Allison on the lips for the first time. It was everything I imagined and more; so hot and passionate was that kiss, I could hardly contain myself. We lay there for a few moments, kissing again and again. Then Charlotte joined us, she kissed me first, then Allison. When the kiss broke Charlotte asked,

“Okay, who gets to ride his dick first?” of course Charlotte nominated herself and Allison nominated herself, so I suggested Rock Paper Scissors. Both found this a reasonable way to settle this… Allison won.

She lay there, legs spread; her perfect vagina beckoned as I put on the ancient condom. I crawled forward, my dick large and erect. I leaned over her and we kissed as I positioned myself over her hot pussy, I could feel the heat radiate from it. She really wanted me!  I gave her one last kiss, and then looked down to see what I was doing; I was perfectly positioned… Here goes nothing I thought, then slowly began to insert myself into her. Ah… God! So warm, so moist! She began to moan when I was about halfway in, she began digging her nails into my back, and her nipples became erect before my eyes.

When I was all the way in I stopped, I felt her and the warmth that she gave off, and I looked up at Ms. P who was watching patiently looking for something to do. Allison looked up for a moment as well, and upon seeing Charlotte she seemed to get an idea. “Hey, Charlotte, why don’t you come sit on my face?” She suggested, “I can eat your pussy while Billy licks your ass!”

Charlotte didn’t need to be asked twice, she climbed onto the bed and squatted over Allison’s face, her asshole facing me.

I began to make small thrusts, my dick slid in and out of her vagina. “Ahhh!” I exclaimed, the pleasure of being inside the woman of my dreams surge through my body. I buried my face into Ms. P’s ass, my tongue making small circles around her small asshole. Allison looked at me over Charlotte’s leg,

“I… I think I… Lov...” She began to say before Charlotte guided her head back to her vagina.

I continued thrusting, faster and harder now. I could hear Allison’s moans growing louder and I buried my head deeper into Charlotte’s shapely ass to keep from doing the same. Charlotte had begun screaming as she began experiencing the first wave of an orgasm, I was pumping my lower body almost at full speed now, I wanted to come but I feared it was still too early. I held on to it with all my strength, Corpses, spaghetti and meat sauce, landfills! But it was no use, I could not hold on to any of these unpleasant thoughts for more than a moment, so hot and wet, so beautiful… FUCK…!

Semen was surging though me now and into the elderly condom, Allison was coming now as well, “AH… AH… AHhhhhhhhh!” she wailed, I tried with all my might to continue plunging in and out of that glorious vagina so she could finish climaxing, but soon, I could do no more and fell exhausted onto the bodies of two of the most beautiful women I had ever met.

We lay there for a while in the glow, kissing occasionally, but mostly we just laid there feeling ourselves next to each other, my satisfied cock still resting inside that most glorious of holes. Charlotte had climbed down from Allison’s face and was now lying behind me, cuddling my back. All was good, and then Charlotte said something troubling.

“My turn!” she said, standing up.

“Fuck!” I said, “Really?” Wow, that girl has some stamina! I loved having problems like these, having one too many women wanting to ride my cock. But Charlotte had been so great about all this; I couldn’t give up on her now!

Lucky for me the solution came to me before I knew what was happening, Charlotte had gone into the bathroom and emerged with something tightly clenched in her fist, “What is tha…” I began to say but was stopped short as a small blue capsule shot down my windpipe.  “Hack! Cough! Wheeze!” I gasped, before finally dislodging it and swallowing it. “What was that?” I asked, but I think I knew the answer already, because my penis was growing hard once again.

“I’m so sorry!” Charlotte said as she tried not to laugh. Did I tell you how much I love Ms. P’s laugh? It’s just so deep and true, the kind of sound that you want to hear all the time, it’s the kind of sound that makes you want to be a good person, you know what I mean, everybody has heard a laugh similar to this before.

“Viagra!” She said now, a contented smile on her face. This woman was absolutely heart set on getting her turn… My dick was growing even harder now; it was almost at its full ten and a half inch glory. I finally built up the will power to remove it from Allison's vagina. I removed the old condom, realizing that we had another problem on our hands. We didn’t have a second condom.

“Uhhh… guys?” I said, “Either of you wouldn’t happen to have another condom, would you?” I was getting a little frightened now. The Viagra was making me horny as a stallion, and I feared without another condom I might have nothing to do with all this sexual energy.

“What’s wrong with that one?” asked Charlotte, then a look of great concern spread across her face, “Oh god, did that one break?”

“No, no! That’s not what happened at all!” I exclaimed, reassuring her, “But shouldn’t we use a different one now?” This is what I had always thought; change the condom after each time, right? But Charlotte didn’t seem to think this was the case.

“We’ll just use that one, because I don’t have any more, and I’m pretty certain Allison doesn’t either.” She said, I looked over at Allison who was shaking her head.

“Alright!” I said, “You’ve had more sex than I have, Charlotte!”  With this I walked over to the bathroom where I made my best attempt to wash out all my semen. When I returned, I looked on in horror as Charlotte helped Allison to strap on a strap on, the large pink prosthetic protruding outwards.

“Fuck no!” I shouted, trying to hide my disdain, “That better not be for me!”

At first all I got as a response was laughter, until Charlotte finally said, “Of course not, silly! This is for MY back end!” Then I understood, Charlotte was going to be between me and Allison! It all made sense, my disgust fading, I exhaled,

“Phew! Thank god, I was about to start running!” I said, relief running through my veins now. I turned to Charlotte then, her nipples hard and her pussy dripping with anticipation, “You ready?” I asked, putting on the condom.

“Oh, Yes!” She exclaimed, “More than ready! Billy, you lie down first, then me then Allison.”

“Sounds like a plan!” I told her, doing as she asked. I lay on the bed, and then she climbed on top of me, her juicy breasts pressed up against my chest. She kissed me then, slipping her tongue into my mouth. I returned the favor as she slid my dick into her awaiting twat; she was slightly looser than Allison had been, but in a good way. It was to be expected, since she was thirty four and had had two children; in fact, if you consider these factors then she was actually tighter than one might expect. In any case, I liked being inside her.

We continued kissing and she began to bob lightly on my penis as Allison took position over Charlotte’s ass.  Then once again my life got more complicated. As Charlotte made a particularly hard thrust the latex of the condom gave way. “Fuck!” She said, I could tell she had felt it. Allison removed herself from Charlotte’s anus.

“What’s wrong?” Allison asked, her perfect breasts bouncing as she sat up.

“The damn condom broke!” I told her, pulling myself out of Charlotte’s warm pussy. God damn it! Now what was I going to do?

“Why don’t I just turn over?” Charlotte suggested, “Billy can take my ass, and Allison can take my pussy!” That woman is a genius, strapons can’t get women pregnant, and neither can fucking them in the ass!

“Charlotte,” I grinned, “You’re a genius!” We kissed once more, and then she flipped over so her anus was resting on my dick. Her little bud was on fire, so hot was she! I spat on my hand then brought it down to her butt, where I rubbed it gingerly into her tight butt hole. Charlotte moaned lightly as I did so. I pulled my hand away, and then positioned my dick so her butthole was once again resting on its head.

“Ok!” I called out, “All set!” And with that, Charlotte began to lower herself slowly onto my dick. Her anus was much tighter than her pussy, even tighter than Allison’s pussy! Although, not quite as wet. She took her time, lowering herself a little bit at a time, clenching and unclenching her anus accordingly. It felt good, really good! I liked being inside her ass.

She continued lowering herself until she sat, my entire dick inside her, all the while Allison watching and waiting patiently until Charlotte had gotten situated. Once fully on my penis, Charlotte invited Allison to take her pussy. Allison climbed atop Charlotte, and they kissed as I had, hard and lovingly. Allison then inserted her dildo into Charlotte’s steamy vagina. I began to move in and out slowly and Allison did the same. Charlotte moaned loudly, her body afire with pleasure. I reached my hand around her back and took hold of one of her large breasts. I kept moving my dick slowly; I was in no rush this time. But Allison seemed to be, she was already fucking like her life depended on it, her lovely tits bouncing with every rapid thrust. I found myself fucking faster just took keep up with her.

Charlotte leaned and turned her head back so she was facing me, we began to kiss but she stopped to let out an enormous moan as I began to thrust harder, plunging my dick into the dark recesses of her anus. For a little I had been worried about getting shit all over my penis but it soon became evident that she had thoroughly washed all that out. I’m not sure when she did this; it must have been right before she made her move on me.

Allison was breathing hard now; beads of sweat began to roll down her face. “Okay back there, Billy?” She asked.

“Yeah,” I grunted, Charlotte was screaming now, her anus clenching tight, making it difficult for me to slide my dick in and out. I could tell she was coming, hard. But Allison and I persisted, however and within moments she was having another orgasm. I could feel myself about to come now. I wasn’t going to stop myself this time; I simply fucked her ass harder than I’d ever fucked before, my hard dick pushing through her anus with great amounts of force. Charlotte Howled louder now,

“OoohhhhhHHHHHhh!” She cried. Then I popped like a cork, I found myself moaning as well and I held on to her large breasts like my life depended on it. Allison too my right hand and pressed it to her breast. The strap on must have been a two way one, because she too was coming. My hot milk filled her burning rectum, and was very out of breath.

We then lay in a heap, all inside one another, hand in hand, covered in sweet smelling sweat.

That day marked the first of many. Three weeks left with nothing to do but be with one another and fuck. Me, Allison, and Charlotte.