Confessions of a Red Hot Red Head

Entry Two: Mr. Pain.

Dear readers: First, I would like to answer some comments left on my last story. Yes, that is how the events naturally occurred. Of course, I omitted random events and facts in the effort of flow, but yes, I was a 22-year-old virgin when I met C. I also hated every single thing about myself. I have no idea where these notions came from, but I honestly believed that topping the scale at over 300 pounds, no one would ever want to be with me. I thought big women should take whatever they were offered because the chance would likely never come around again. Please take note that it was my own cowardice and embarrassment that lead me to never pressing charges, not the NDA that I signed. That document, which I later found to be completely fraudulent, would never hold up in the court of law. I simply was too scared to go through the he said she said process at my small liberal arts school.

Now, with all that being said, I can tell you in full confidence that being with the politician, no matter how horrendous the final act between us, probably saved my life. Walking out of that hotel room, I made a promise to myself that I would never be that girl again. I would never share myself with another person until I liked myself enough to show some self-respect. It was in that moment that I made a commitment to change every facet of my life. I had four months before I took flight to the land of my ancestors to go to graduate school—I was bound and determined to set foot on the Emerald Isle a whole new version of my self.

When I walked into Ireland's oldest and most prestigious college, I weighed 85 pounds less. A whole summer of working out for hours a day and eating a several calorically restricted diet brought about a change in my shape... It also brought about a change in my self-confidence. With my chin length perfected curled deep red pageboy haircut, MAC makeup, and a whole new and sexier wardrobe- I hit the clubs and pubs with a vengeance. I was living life and loving every minute of it- that is until I ended up in the hospital, and before I knew it, on a plane back to the U.S. for surgery.

And that, boys and girls, is how I came upon my hottest high school crush, while filling a prescription, in my hometown grocery store.

Mr. Pain.

E. and I had been great friends for a few years in high school. When I first moved from my major metropolitan home city to a small rural county in the country after my parent's bankruptcy, I thought for sure I was going to die of pure boredom. Back then; my style was more dark and dangerous than anything else. With my elephant bottom JNCO jeans, fishnet sleeves, sarcastic tees, and coffin backpack- I was surely going to make a statement walking into the small country school for the first time. Luckily for me, the country is full of kids who want nothing more than to be different from everyone else. E. was one of twenty students at my school who looked like me, listened to music like mine, and hated "conformity" (yes, while dressing and talking just like one another). E. was one of my three best guy friends, he was also the subject of every schoolgirl fantasy I could envision. He was a track god, lean and mean with an exotic look from his Hispanic mother. I use to go to his house and buy five-dollar joints, just so I could hang out with him one-on-one. Of course, I never told him that I liked him. Couple that with the fact that by Junior year I had become more focused on getting into a good college than hanging out and getting stoned, and you can see why after he graduated, we never saw one another again.

That is until I was walking through the aisles of the grocery store and I saw E. standing there, contemplating one bag of chips over another. Spurred on by my new look and resounding confidence, I went up behind him and said, "Well, if you have the munchies- always go for the cheesy option."

Turning around he said, "Thanks. I'll keep that in mi—.... Red?"

Instantly, I felt a wave o pride that he did not recognize me off the bat. Most people from H.S. don't upon first glance; so much about me has changed, right down to my newfound ability to make eye contact.

"Got any smoke to go with those?" I asked while fluttering my long lashes.

"Sure, back at my place, wanna go spark up and catch up?" he responded.

With that I picked up my prescription while he checked out and before I could even contemplate what was happening, I was following him back to the house he shared with some work buddies. All along the drive I kept playing to possible outcomes in my head. One, we would chill, find we had nothing in common anymore, and then I would go home and take care of myself wishing things would have turned out differently. Or, two, I could make something different happen. I could stop being irrationally afraid of rejection and just go after what I could never have in High School. I could do the ultimate former fat girl move—hook up with someone who never saw you as you were before. In all honesty, isn't that the fantasy most big women have in their heads... 'If I could just get skinny person X, Y, or Z will finally notice me?"

We ended up on his couch, watching some comic book movie while he rolled us his trademark fatty. We chatted a bit, reminiscing good times, horrible teachers, and recapping the last seven years since we had seen one another. After two hours of smoking and talking, I figured the night would turn out like option one. But, to my surprise, he looked at me while passing the J and I felt a spark.

"So... I have to tell you Red, you look fucking sensational. I love what you did with your hair." He said with smoldering eyes.

Gathering up all my courage I responded, "Thanks, E. You look pretty damn good yourself."

And that is all it took. We collided into a mass of writhing tongues and groping hands. E. surprised me by taking my bottom lip and biting it between his teeth. The moan that escaped me was nothing short primal. He broke the kiss and looked into my eyes with amusement.

"Like a little pain do we?" He asked.

"I... I don't know. Honestly, you are only the second person I have been with and the first guy—well he was rough, but I can't say I really liked it." I answered embarrassed.

"Trust me Red, there is a difference between pain for pleasure and pain for power. I personally love the former, so have at it." He said while leaning in to reconnect our lips.

I took what he said and mulled it over while kissing him in earnest. I loved the feeling of his teeth clamping down on my lip. Did that mean that I could enjoy a level of pain with sex? I wondered if I was always like this, or if C. had caused this within me do to my introduction to sex. I was determined to simply act and not overthink. Who knew if this was a one time thing? And, if it were, why would I waste a single moment second guessing myself? I began to kiss him more savagely. Mimicking his earlier actions, I sucked his bottom lip into my mouth and bit down, gently at first, but then I heard him groan, and in response, I doubled the pressure of my teeth on his soft flesh. His hands came up and gripped my ringlets, pulling roughly, but not rough enough to cause discomfort. I found the act extremely hot so I took to sucking and biting his neck. We broke long enough for him to take off his shirt and I continued my tour of his body by focusing on his nipples.

"Fuck!" He spurred when I sucked and bit his right nipple hard...my teeth pulling his nipple taunt and my tongue flicking mercilessly all around the hard little nub. The pressure on the back of my head increased- and I knew he was enthralled. I didn't make this choice consciously, but somehow I determined that I was going to be the fuck of his life... that if I finally got to be with the guy I had wanted throughout the formative years of my adolescence, I was going to make sure he remember this for as long as I would. I moved on to his left nipple, mirroring what I had done to the right.

"Jesus Christ, yeah! Fucking bite me. Shit, that feels so fucking good." He was streaming compliments and obscenities for the whole ten minutes I spent doing nothing but tormenting his nipples. I took no prisoners and he left me inflict an amount of pain I know any other man would be crying from.

He pulled my hair and I released his nipple. Claiming my mouth as his, he reverently stroked my tongue with his own and then did the classic male move, slowly lowering me by the hair to his still jeaned groin. In all my session with the politician, one thing I learned to master, was giving head. So I went at it with absolutely no abandon. I popped his button, and undid his zipper. He leaned back against the couch and in one fell swoop, took of his pants and boxers. His cinnamon colored skin was dusted with dark curly hairs, starting around his cock and continuing down his lean runners legs. I began by tongue bathing his member. Working from the bottom, flicking my tongue a few times at the apex of his cock and testicles- his hands gripped the couch cusions and his eyes screwed up tight. Making my way up the six inches to his swollen head, I made sure to get a lot of moisture all over his shaft and swirled his head repeatedly with the flat of my tongue.

"Stop fucking teasing me a suck it!" He yelped.

I did as asked and impaled my mouth on his dick. Sucking as hard as I could, I used my right hand to grip the base of his shaft while my left was busy gripping and groping his drooping balls. I rotated my head, right left up and down, while sucking. I turned into a cock sucking cyclone and his hands were grasping at the couch, the air, various parts of my body, and finally settled into my hair. He used this new leverage to lift me up and down his cock at his own pace and as the head moved into my throat I heard him whimper with need.

"Fuck girl, I'm going to cum." He breathed.

Breaking contact to look up into his eyes I challenged him "I'm ready when you are." And I went right back to sucking the very life out of him with everything I had to give. In my most brazen moment, I slightly barred my teeth on his head and gently bite down.

"God, aww shit... fuck!" he was gasping for air and soon began to pump a sticky substance down my throat.

He used his hand in my hair to make me come up from his oversensitive member.

"Where... the fuck.... Did you learn how to do that?" He asked in awe.

"I had a very difficult teacher" was all I said in response.

He grabbed me by the hand and lead me to his bedroom. Turning on some Disturb (which I have no idea if for nostalgia, or because he still listened to their music) he pushed me onto his bed and turned off the lights. Joining me on his bachelor bed (unmade, one sheet, one pillow) I noticed he had dark purple hickies surrounding both of his sexy little nipples.

"Shit E. I'm sorry, did I hurt you?" I asked abashed.

"No. Never. I fucking love it... If you haven't figured this out by now, I really, really enjoy the use of pain in pleasure- especially when it I am on the receiving end." He said while twisting his fingers into my hair.

"My turn" He announced with a smile.

He returned to kissing me softly, then with more force. Taking my tongue into his mouth he sucked and bite it while I writhed beneath him. He was between my legs, his naked stirring sex was agonizingly rubbing against my clit as he circled his hips and ground into me while kissing my neck, licking and biting my ear lobes, and groping my chest. A series of small moans and gasps escaped my lips as he spent more time offering pleasure to me than any man before. He went to put his hand under my shirt, but I stopped him- still not comfortable enough in my own skin to be naked in front of a sexual conquest. He got the message and slid his hand up my deep purple mini skirt instead. His fingers were playing with my most vulnerable parts, something I had never felt and I was in pure ecstasy. I had no idea what I was missing with C. These feelings, this amazement was the stuff of erotic legend.

"Fuck me" I pleaded.

He got up to get a condom, and I quickly removed my boy shorts. Looking up at him embarrassed I said "Its been almost a year" as a way of warning him to go slow.

A smile spread across his face as he replied "No worries" and slowly, agonizingly, he applied pressure and worked himself to the hilt. I let out a garbled breath as he bottomed out inside of me. He was going so slow, taking care not to hurt me. As sweet as that was, after about two minutes I wanted, I needed more. I needed the passion, the heat, that only comes from no holds barred fucking. I gripped his ass in my hands and forced him into me deeper and harder than he had before.

"Impaient are we?" he chuckled.

With that, he took off the kid gloves and started to fuck me with the roughness I thought I didn't want, but I absolutely needed. In moments we were sheened in sweat. His arms were rigid from hoisting himself over me, his balls slapping against me with every labored stroke. The feeling in the pit of my stomach that was intensifying with each pump was invigorating.

This was the best sex of my life, and I didn't want to waste a second—so I decided to be brave and ask him for what I wanted. I made my motive clear, putting pressure on his leg and using my right side to get him to switch, he took note and stopped. He layed down on the bed and I began my tour of his amazing body all over again. I visited his neck, nipped at his earlobes, tortured his nipples and kissed and sucked my way down to his happy trail. I sucked his stomach flesh into my mouth and bite down about a half inch from the start of his cock- he groaned and clawed and the sheets. When I started to lick and roll his balls in my mouth...

"Enough. I can't take anymore- let me fuck you." He begged.

I complied by straddling his hips in total fear; fear that I would break his slender frame, fear that I would lose my nerve. Gathering up all my will power, I gripped his dick in my hand and angled it into my wet and needy core. I slowly began to ride him as he gripped my hips and helped me gain a rhythm. The pounding rock music spurred on my desires and soon, I was matching every drumbeat to the rock of my hips. I no longer cared if I was a plus sized woman, I no longer cared if this was the man of my teenage dreams... at this point all I cared about was finally getting to experience one of the mysterious of a woman's life—the big O. I began to ride him not for his pleasure, but for my own. The feeling of his cock inside of me, brushing up against my G spot and my clit grinding against his pubic mound was simply outstanding. I was covered in sweat. Lost in the sexual wonder that was occurring within me, I racked my nails down his sides.

He screamed "Fuck yes, make it hurt baby!"

I quickly realized that while a little pain for pleasure can be a good thing when receiving, there is nothing better in this world than a man, completely at your mercy, asking you take control, take the power, and cause them pain. I bite, I scratched, I squeezed and I rode him as though this were the last time I would ever have sex. We continued in this daunting rhythm of bouncing and he started to thrust his hips up into me, making his cock go even deeper. I was lost; I was becoming a newer version of myself with every stroke. Sweating out the self-conscious scarred little girl I was becoming a wanton fucking machine... and I was loving every moment of it.

My right hand wondered on its own accord down to my clit and I began to rub myself senseless while riding his cock. E. was holding onto one of my hips and one of my tits while I shimmied and swayed above him. That roller coaster feeling returned, and I began to hope and pray he wouldn't come before I got the chance.

As if reading my thoughts he said "I'm going to cum... hurry"

I leaned down and kissed him passionately, severely biting his lip in the process. When I released his lip, I saw a staining of red and I knew I broke skin. His strangled cry told me that was completely okay and I knew he couldn't hold out any longer. Instantaneously I felt him begin to empty within me, his breathing ragged.

"Fuck.... I'm sorry" he said embarrassed as I collapsed on top of his chest. He was stroking me back in small circles, allowing me to catch my breath. When my sense returned, I slowly dislodged from him from my sex and rolled over onto the bed.

"Did you?..." He inquired.

"No, but its okay—I never have." I answered turning as red as my hair.

"Next time" he responded.

We fell asleep in the post-coital high. We I woke up, the early morning sun was beginning to show and I knew it was time for me to go. All those insecurities I felt for so many years came washing back over me, and suddenly, I had to get out of there before he awoke and told me what a mistake that had been.

As I opened his bedroom door, I heard him stir from his slumber.

"What time is it?" he asked sleepily.

"Early, I've got to go." I said not turning around.

Before I could get out the door, I felt him behind me.

"Thanks for last night gorgeous. I hope we can do it again sometime. Soon. " He said while planting soft kisses on the back of my neck.

"How soon?" I asked as I turned and captured his lips passionately.

E. and I had sex five more times before I finally got up to return home.

Dehydrated and totally spent, I left with a smile on my face and an amazing feeling of fulfillment, both within the deepest part of my conscience and my core. I knew that a new me was born in the sweat and sway of that night. I now knew that I could be sexual and sensual without fear of being too big for comfort.