I pick Jeremy to be the first to fuck my ass.

Jeremy is by far the nicest guy I know. His warm eyes aren't afraid to look into mine. His touch is gentle, communicating respect. He has a great sense of humor even though he doesn't know any jokes. His humor comes from everyday life. He never misses any silly little thing that I do; he is always paying attention. Almost nothing is sexier than that. And he seems to genuinely like women, especially me.

So I decided that Jeremy would be the one. My curiosity had evolved over the last few months to something much more. I wanted this to happen; really I needed it to happen soon and on my own terms. There is only one problem. Of all my male friends, Jeremy has the biggest cock by far. Both long and thick, it is not the perfect combination for the task at hand. But in my mind Jeremy was the logical choice. It simply had to be him. I would just have to find a way to make it work.

--- Scene 1: The Phone Call

"Hi, Jeremy, this is Emily."

"Hi sweet thing. What's up babe?"

"Not much. I was hoping you were free to come over tomorrow night. I have a bottle of Beaujolais that is about to celebrate its second birthday. We can't let happen can we?"

He laughed, "No that would be a crime. What time Em?"

--- Scene 2: The Shower Ritual (No fucking yet. Be patient.)

Men think they are always ready for sex. They don't really know what it means to get ready for sex. A gal is lucky to get the guy with a clean shave and no bad breath. A man never prepares for sex like a woman does. Women love the preparation part. It's all part of the game.

It starts days ahead of time: shopping for a new pair of panties; sending all the candidate outfits to the cleaners; inspecting every inch of cloth for the tiniest flaw; shining the shoes; better yet, buying new shoes; stocking the refrigerator with his favorite snacks and beverages; and one mustn't forget breakfast supplies just in case.

The shower ritual is my favorite part of foreplay. Everything must be cleaned in the proper sequence. First, I remove every trace of makeup and fingernail polish. Right before I start the shower I thoroughly wash my hands. How can a girl clean her body with dirty hands, I think to myself?

The shower itself starts with at least 10 minutes of the hottest water I can stand cascading on my head and neck and breasts. I spend a good bit of this time thinking about the guy I'm preparing to fuck. When I reach the proper mental state, I move on to the next step, the body shave. I shave practically everything: my legs, my armpits, and my pussy.

As I shave my pussy, I never miss the opportunity to spread my lips and check the status of all my female parts: yep, fully operational. But perhaps I need to double and triple check the key parts around my clit. This can take quite some time (grin).

Next I shampoo and condition my hair. As I do this, my mind drifts back through my greatest hits of sexual encounters. Like the time I wrapped this same, freshly washed hair around Brian's cock and jerked him off right into it. Two shampoos in one day. How lucky can a girl get?

After my hair, I meticulously clean every square inch of my body: between every toe, deep into every crevice, and along every curve. A girl never knows where her lover's mouth might venture.

Once all the parts are clean, I clean myself again with a good shower gel. For Jeremy that night I chose "Vanilla Birthday Cake." Jeremy loves eating birthday cake.

After the shower I do my makeup and hair. I keep it simple stupid. We are having sex after all, not going to a state dinner. Finally I end as I began: with my fingernails. For sex I always choose red: black underwear with red nails. The kinds of men I like do not want innovation; they want a woman.

--- Scene 3: Baiting the Hook (Still no fucking. Sorry.)

"Hi Jeremy. Come on in." I greet him with a kiss and hug.

"Wow Emily! What's the occasion?"

Evidently he liked my outfit: a little black dress that is way too short; black heels; no stockings or panty hose. We give each other a hug, but I made it linger a bit. I can tell my scent is tempting him to get closer and closer. Jeremy really didn't stand a chance.

"I feel underdressed Emily."

I wonder why he thinks that. He's wearing the standard guy uniform: jeans and t-shirt with loafers; no socks. However everything seems clean enough and he smells great too. Even more importantly his jeans are sporting an exceptionally fine ass and an even finer bulge up front.

"Wow what is the occasion Emily? Really. I thought we were staying in. We going someplace?" he asked.

What a silly boy. Sure big guy. Just you wait and see.

"No silly. I just wanted to look good for you." I told him as I batted my eyes and gave him my innocent little girl look.

"Oh wow you look great! By the way, I smell a birthday cake? Is it someone's birthday?" Jeremy said. He took his eyes off me for just an instant to look around. Little did he know his "cake" was the brunette standing right in front of him.

"You look GREAT too, Jeremy." I told him. "I'm so glad you could make it tonight. Come on in."

I touched his arm to give him a gentle pull into my apartment. Then I make a point of closing the door, locking the dead bolt, and latching the security chain. His face glanced at mine. I could see his Adams apple make a little gulping motion in his throat. I smiled back. I think he was finally getting the point.

--- Scene 4: The Bottle of Wine (We still aren't fucking yet. Deal with it.)

Well into our second glass of wine Jeremy realized just how much I needed to get laid that night. No guy could be that dumb. He was smart enough to know that I still wanted to be wooed carefully. My forwardness had made me vulnerable and a little insecure. Plus I was sitting on the couch right next to him in a little black dress that was not designed for sitting. He couldn't keep his eyes off my long white legs. Jeremy's job now was to be the man and treat me right. I had made all the preparations. Now it was his turn for affirmative action.

A man must be very careful what they say to a woman in the heat of passion. Total bullshit or any sign of weakness can undo 30 minutes of foreplay. Thank God Jeremy instinctively knows this.

He whispered softly in my ear, "Emily, you look so incredibly beautiful tonight. I'm so glad you invited me over. Hey are you the birthday cake I smell?"

I responded with a big blush and a little smile. Then he kissed me. Our lips were closed at the start of the kiss but didn't stay that way for long. As our mouths opened to each other the kiss became the first official act of sex.

I'm a very aggressive kisser; not that night however. My mood that night was much more passive and receptive. I yielded to his wine flavored tongue in my mouth and gently sucked on it. It probed my mouth with growing passion. He paused to check for my response. I gave him the signal he was waiting for; my tongue licked his lips delicately and then traced the surface of his teeth top and bottom. My growing passion f***ed me to I suck his lower lip and melt deeper into his arms.

His mouth returned to dominate our kiss. My hand traced along his flat, hard stomach, and then moved downwards towards his belt. His hips rotated slightly, encouraging my exploration. Soon, my hand found his bulging manhood under his jeans. I gasped. The size of cock never ceases to amaze me. His breath caught in his throat, so I gave him my breath to breathe. My air saturated him with lust. Jeremy's lungs decoded the meaning of all this instantly. In response, his cock strained within his pants.

Once the cock is hard the rest is inevitable.

--- Scene 5: The Surprise! (Finally the fucking finale)

Jeremy and I were soon naked on the bed, the blankets long since thrown to the floor. His mouth had visited every hidden place on my body. He had already licked my clit through a starter orgasm. Now it was cocksucking time.

Jeremy knelt beside me; his hand on the headboard balanced his body; his other hand was wrapped around the base of his long cock. The part of his dick that was sticking out of his hand was still long by any standards and he was offering it to little old me.

I find sucking really big cocks to be a challenge. Jeremy has the biggest and thickest one I have known. I am simply incapable of taking much of it into my mouth. It makes me feel totally inadequate. I take pride in being a really good cocksucker, but how can I ever prove it to him. How could any woman give him a proper blowjob? But he was oh so gentle and understanding with me that night. I shouldn't have worried.

My tongue licked along the shaft concentrating on the sensitive underside and head. I opened my mouth wide and took some of the giant helmet head inside. My tongue probed the long slit that is his cock hole. My fingers tried to circle his shaft near the middle but the dick was far too thick. On second thought it was my fingers that were too short. I tightened my grip and drew my hand toward my mouth. The cock responded as I had planned. The shaft under my hand became even harder and the big head throbbed. I saw the first drops of pre-cum. I put my lips around the mouth of his cock and took a drink. The taste was very subtle; mostly I tasted the saltiness. The texture was liquid silk. His juice mixed with the taste of his saliva already in my mouth from an earlier kiss. Soon all that I could taste or smell was Jeremy.

"Emily, please, sweet. Please stop. Stop or I'm gonna cum. Oh shit."

Maybe I wasn't such a bad cocksucker after all. I pulled my mouth back from him. His hand moved away from his cock leaving me to hold it. I hefted the monster before my eyes admiring the sight: swollen, red, wet, weeping, and above all hard. "Oh shit" is exactly right. This is exactly why I'm here on earth: to get fucked by this thing.

The day that my mind can't recall the image of Jeremy's cock at that moment is the day that I die.

More pre-cum oozed out and I couldn't help but lick it off. I was risking catastrophe but a girl has to do what a girl has to do. His eyes were tightly shut and his breathe stopped again. He was right on the fucking edge.

I wouldn't let him cum like that. Not that night. We had other business to attend to. I removed my mouth and hand from his cock; it bent downward a bit from its massive weight.

"Please fuck me now Jeremy. Please." My plea was not up for negotiation.

He smiled at me and moved between my legs. We both let his cock go unattended for a moment. It really needed a rest. He sat back on his heels, and d****d my spread legs over his thighs. His hands spread my pussy, exposing my total wetness. He leaned down and gently kissed my clit.

"Oh, YESSS." I groaned.

He continued to lick around my clit for just a few minutes; then he sat back up between my legs.

"Play with your pussy, Emily. I want to watch. Like the old days."

"Yes sir," I think to myself without saying it out loud.

Without hesitation my fingers went straight to my pussy. He and I had masturbated together before so I was quite comfortable doing this with him again. I knew how much he enjoyed watching me play with myself.

I began to stroke the side of my clit slowly and circle it with two fingers; he took his massive weapon in his hand and began to masturbate for me too. What a glorious sight that was. What a glorious fucking sight indeed. His face was racked with lust, studying my every move, staring fixed at my pussy, while his large, tanned hand pumped slowly up and down. His cock grew fucking HUGE. It seemed to me to reach up past his belly button. My whole body started to shudder. Oh, God. I stopped masturbating and tried to get his attention.

"Jeremy. Jeremy. Please stop for a second. OK?"

He looked up at me with those big blue eyes. It was time for me to give him my little surprise.

"I want you to fuck me in the ass." A stunned look washed over Jeremy's face.

"Wha..." was all he could muster at first.

I repeated my plea in a low whisper.

"I want you to be the first to fuck me back there. I want you to fuck my ass."

"But, but, but. Emily, are you sure about this? I've never..."

"Yes, Jeremy, I'm sure."

"But, Emily, no one has ever, you know. I've never even tried that with another girl before. Is it even possible? Won't I hurt you?"

Jeremy was not being arrogant about his big dick. He was genuinely worried.

"I don't think so sweetheart. If we take it slow I think I can do it. And I know you'll be gentle with me."

After some more reassurances Jeremy agreed to try. I had him put a big pillow under my butt so my ass was high off the bed. I reached for the KY jelly somebody (I wonder who?) had left under the pillow.

"Please use this OK Jeremy?" I asked a little sheepishly. "And please use your fingers first. It will help me open up for you."

I pulled my knees back to nearly my chest, my ass angled high up towards his face. He put the jelly on his index finger and brought it to my asshole. Gently he spread it around, lovingly coating every part. He put an even bigger blob of KY on his finger and tried to push it into me.

"Jeeesus Emily; you're way too tight. Are you sure about this?"

"Go ahead before I loose my nerve dummy. Put it in. Put your finger in me."

I felt his finger push at my opening again. It resisted at first but there was too much lubricant to stop it.

"Aaaahhhh" escaped from my lips as his finger penetrated me to the second knuckle.

"Are you OK Emily?"

"Oh, yes. It feels kinda funny. But a good kinda funny. It's OK. Keep going Jeremy."

Soon his long index finger was slowly fucking my ass back and forth. My ass muscles clinched down hard several times, each time amazing Jeremy with their power.

"Damn you're tight. Damn you're tight." he repeated over and over.

I grabbed his wrist to give him encouragement. When the muscles in my ass would clinch down too hard, my hand would hold his wrist still signaling him to wait. Then I would close my eyes and concentrate on relaxing. Sometimes this would take many seconds, but eventually my hand would loosen the grip on his wrist and he would continue finger fucking me.

"More lube and two fingers now, OK Jeremy? I think I'm ready for more."

After five minutes of stretching my asshole with two fingers, we graduated to three. Incredibly, my virgin asshole seemed able to adapt to the invasion. Now I sensed it was time for the main event.

"I think I'm ready for you sweetheart. But please put lots of stuff on your cock, OK?"

"Sure Emily. I still can't believe we're doing this. I can't fucking believe this. Oh, wow, you are so incredible."

Jeremy's cock had subsided a bit during my extended ass stretching exercise. However as soon as he applied the lube to his cock and started to stroke himself, it quickly returned to full mast. "Damn" was the only thought I had as I watched it grow back. I was getting really nervous. It really didn't seem possible. He applied even more lube to the end of his cock and my asshole and he brought his cock to me. It was poised right at the entrance to my bowels awaiting final clearance for entry.

"Are you ready?" he asked.

I answer with a nervous smile.

"You tell me when to stop. Try to relax."

I knew I was in good hands.

Jeremy pressed the head of his cock on my asshole; that big fucker was at least ten times bigger than the little gape we had opened in my asshole. Even worse was the shape of the head of his cock: it has a very blunt shape. A cock with a pointier head would be better for ass fucking I suppose. But there was no denying it. Here I was: spread-eagled, totally lubed up, and reamed out. This was what I had asked for; now I had to face the music.

He pushed harder. Nothing happened except my entire asshole got pushed in a little.

He pushed even harder. My asshole pushed in a little more. Still no penetration. He pusher even harder.

"Ahhhh. Ahhhh. Ahhhh"

I couldn't speak now but my hand on his hip signaled him to continue.

"Ahhhh Ahhhh AH!" A jolt of real pain hit me.

He pulled back, quickly squeezed another massive blob of lube on the end of his cock, and moved it back in. He looked even more determined to get his cock in me this time.

The pressure increased, then doubled, then tripled.

"Oh, Ahhhh, Ahhh, Ah, AH!" I was starting to hyperventilate. It was making me really dizzy.

"PUSH HARDER GOD DAMN IT!" I yelled and he obeyed.

Finally my asshole surrendered. He was in. The head of his big fucking cock was in my virgin ass.

"OH OH OH ..." I repeated a million times.

My mind was reeling. I kept telling myself to relax. I could hear his voice in the background. "Are you OK Emily? Are you OK? What should I do? Are you OK?"

In my mind I was thinking: "Of course I'm OK you stupid fucking idiot. This is fucking fantastic." However I seemed to have lost the ability to speak.

Finally I managed to say one word out loud,

"More."

So he resumed his pushing. Now that his entire cockhead was inside my ass, the tight ring of my ass had clinched around his shaft. This part was a little easier. Soon a totally weird feeling of fullness came over me.

"Oooo wow. What's this?" I think to myself.

Part of the feeling felt like a big turd moving the wrong fuckin' way into my ass. Another part, the good part, was a burning heat that quickly spread up to my pussy. I was catching on fire from the inside out and it was driving me nuts.

Jeremy could not push his cock straight in and out like a normal fuck. It was way too tight for that. Instead he used a slow little rocking motion: first in a little; then out a little; then in a little deeper; then out a little. As he did this, I could see sweat breaking out on his forehead. My sphincter could literally feel his cock swelling. It transmitted every last detail of his cock shaft directly to my brain. I had no idea that my asshole was so sensitive or so talented.

I watched him as he brought his thumb up to his mouth to wet it. Then he moved it back down to my pussy: my poor, forgotten, lonely, overheated pussy. But sweet Jeremy did not forget it. His thumb traced up and down my engorged pussy lips. He collected some of the swampy mess he found there and spread it around my clit.

His big thumb began a gentle circling motion around my clit. He did not press too hard like some men do; his touch was oh so light and just the right speed. It took about 15 seconds of this before I started cumming.

The first orgasm hit me like a lightening bolt right out of blue sky. Sharp. Intense. Completely unexpected. His thumb kept right on circling. The second orgasm hit me about a minute after the first. This one was deeper and more powerful, like rolling thunder. My butt was high off the bed and my back was arched. My head rolled back and I started grunting and screaming. The orgasms grew stronger and blended into one long unbelievable sequence of earthquakes. I came again and again and again. My hips were dancing up and down, bouncing uncontrollably on the monster pole stuck up my ass. Jeremy on the other hand wisely did not move a muscle.

As my orgasms subsided my mind began to clear. Now I could truly focus on the moment. This gorgeous young man with the big cock and the bigger heart was fucking me senseless. So what if he was fucking my ass and not my pussy. This was fucking in the purest sense of the word.

I focused on Jeremy's face. Beads of sweat covered his forehead and his cheeks had turned a dark red. His eyes were tightly shut. His expression seemed almost one of pain. I could tell he wanted this to last longer. Obviously it was not to be. Jeremy was only human.

His cock was engorged to its full size. Rigid, tall, and proud, like the mast of a great sailing ship. Perhaps four long inches remained outside my body, holding my ass cheeks apart. The fullness inside my belly told me that much more of his cock was deep inside of me
Slowly, almost imperceptibly, Jeremy drew back an inch or so; my tight sphincter implored him not to leave. Gently, the cock would pause briefly and return pushed by the manly f***e of my gentle lover. I could feel the head of his cock pulsate at the brink of orgasm. Poor Jeremy was trying so hard not to cum. He kept his eyes closed and his brow furrowed. His breaths were long and deep. This was about all any man could take.

Mercifully Jeremy's thumb had left my clit thereby letting my head clear. I was absolutely full of cock, stretched to my utter limit. The feeling is extremely hard to describe. It was more than just a mixture of pleasure and pain; I was in a state of total vulnerability and complete submission.

Jeremy's face and the incredible state of his cock told me everything I needed to know. He had never felt anything quite like this. We both knew instinctively we would probably never be able to recreate this moment again. What a gift to be able to give to a man.

"Jeremy sweetheart. Please open your eyes." My voice had returned to me and it was clear, calm and loving.

"That's better sweetheart. Now look into my eyes. Talk to me Jeremy. I want you to tell me what this feels like to you."

He groaned. Any man with a hard cock is no great conversationalist. A well hung man is at a double disadvantage. His poor bl**d-starved brain was no smarter than that of a wart hog. But, bless his soul, Jeremy tried to talk anyway.

"Ugg. So smooth inside. Ah. Ah. So tight. LL. LLLL. Looks. Looks. Looks great! Fuckin' great! I can't I can't..."

"Jeremy, please look into my eyes again. That's it lover. That's better. Now relax baby. It's time to just let it go. You need to cum now. I want to feel you when cum in my ass. Go on baby do it. Do it now. For me. Just let it happen."

My voice was soft and gentle, my instructions plain and clear. I saw the tension in his face disappear and his body give in to the orgasm. From deep in my bowels I could feel the head of his great cock grow even larger. I was literally impaled on his spear of a cock and its head was blowing up inside me like a balloon.

Jeremy lifted his hips involuntarily and pulled my body up with it. Two more inches of thick cock pushed into the core of my being. My dear sweet man did not pump or thrust at me. I watched as his big blue eyes rolled up into their sockets. I watched as his face contorted in anticipation of the sweet agony of release. Incredibly he made no sound. The sound was trapped inside his body. Only his cum could escape.

The entire bed started to vibrate in respond to the quivering of his thighs. His big hands squeezed at my hips. Then abruptly his quivering stopped; he became completely still. No motion at all. His face turned an even deeper shade of red. I spotted just a hint of shuddering of his jaw muscles. Soon my sensitive asshole detected his merciful release. He was finally cumming. My lover was cumming in my ass.

I did not believe it was possible to feel so much with my ass. The first pulse of cum moved with great f***e up the channel that runs along the bottom of his cock past the slight resistance of my anal ring. My insides tracked his cum those last five or six inches deep into my anus. Then I could feel a pocket of extra fullness develop as my bowels made room for his load of semen.

The second volley of cum was at least twice the amount of the first. The third volley was nearly as big as the second. The fourth, fifth, and sixth were still massive but I could tell they were growing smaller. Soon all I was left with was his shuddering. My big, strong man was reduced to helplessness; Jeremy was completely drained of all his virility.

At first the gigantic pool of semen inside me just gave me this sense of fullness. After a few moments the sensitive skin inside detected a wave of heat as my body absorbed his hot load. It was like a time bomb. Fucked in the ass by a delayed reaction cum-bomb. What a way to go!

My once virgin ass reacted rather strangely to the hot cum. It contracted. HARD.

"Ahhhh! God" was poor Jeremy's reaction as his spent prick was squeezed to death.

With his cock emptied of its potency he had no defenses left. My powerful muscles had rung the remaining bl**d out his cock. He pulled back: first one inch, then two, then three, then four, then five. As soon as the rim of his cock head reached the opening, my powerful ass muscle unceremoniously expelled the rest in a flash.

He crumpled beside me on the bed. I took him in my arms and kissed him softly. I placed my leg across his tummy. He was defenseless. It became my responsibility to protect him from harm until he recovered his strength. I love this part of sex.

As he rested, I glanced down as his limp cock still red from its ordeal. How placid it looked. My mind wandered to the sensations coming from my body. My ass was aching but there was no sharp pain. My finger found my sore asshole and probed the gaping opening. I gently pushed my finger inside to the second knuckle. Oooooh that felt weird. I withdrew it. It mostly smelled of his cum with just the faintest hint of essence of me. It is by far the nastiest smell ever to have entered my nose and without a double the sexiest.

So, I DID IT!

My womanly repertoire is now complete.

To the right person, under the right circumstances, I can finally say,

"No holes are barred."

THE END

100% (10/0)
 
Categories: AnalFirst Time
Posted by fotisampini
11 months ago    Views: 3,607
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