Obsessive Olivia

My name is Olivia. At the time of this story I was fourteen years old, and a Freshman in High School. I was physically and emotionally very mature. I was 5 feet, 1 inches tall, and had long blond hair. I had the body of a women with 34D breasts, a small waist, and full hips.

My family had an apartment, over the garage, that they rented to boarders. A day before school started, they told me they had rented it out. I watched as a very handsome, twenty one year old man moved his stuff in. I didn't have time to meet him, I had school the next day.

The first day of classes, of my Freshman year, I went to fourth hour English class, and got quite a surprise. There in the front of the room teaching, was the same man who had just moved into my garage.

He introduced himself to the class as Mr. Cooper, and said this was his first teaching assignment. He outlined the course syllabus and rules, and then began the first unit, poetry.

I am a romantic at heart, so when he started reading, How Do I Love Thee? Let Me Count The Ways by Elizabeth Barrett Browning, I just couldn't keep my eyes off him. He looked like a young Robert Redford, with blond hair and blue eyes. He was dressed like a professor in a brown corduroy sports coat with arm patches.

After class I introduced myself, and told him we were neighbors. He told me he looked forward to talking to me soon. I could hardly wait.

That evening, after dinner, I climbed the outside steps, leading to the apartment, and knocked at the door. Mr. Cooper opened it up.

"Hi," I said, "I came by to talk as you said."

"Sorry, Olivia," he said, "but I really have to unpack."

"That's OK, maybe I can help." I said, walking right in.

I was dressed in short/shorts and a tight tube top, quite sexy for a fourteen year old. He took a double take and then led me to a group of boxes. As I handed him the books from inside, he placed them on a nearby shelf.

"This is quite a poetry collection, Mr. Cooper." I observed.

"Oh, as long as we're neighbors," he said, "you can call me Tom, outside of school."

"OK, Tom," I said. "I sure like your taste in poetry."

"You like the Romantics?" he asked.

"They're my favorites." I said, flipping through a book.

"You can borrow them anytime you want." he said.

"I also like to write poems." I continued.

"I'd love to read some." he said, "And don't worry, I won't grade them."

I laughed and helped him unpack until it was time for me to go home.

The next few weeks were great. In class, I hung on every word Mr. Cooper spoke and afterschool, I helped Tom unpack and organize the apartment. We talked constantly and I was completely surprised we had so much in common.

After he was settled in, I continued coming over and started helping him grade papers and do record keeping. We talked a lot about about poetry and literature. He became more of a mentor than a teacher. The relationship was totally professional.

That changed suddenly for me. One night, I got up from bed to use the bathroom. My window overlooked his bedroom. As I glanced out, I noticed he had forgotten to close his drapes. He was asleep on his back, and the moonlight illuminated the whole room. Tom was completely nude. As he lay there, my eyes went right to the area between his legs. His penis was flaccid, but even in that state, it appeared to be eight inches long.

I couldn't believe it. I suspected his penis was big, from seeing the outline in his pants, but I never figured it was this large. My hand automatically went down into my panties and started rubbing my clitoris. I was still a virgin but all I could think of was how that thing would feel inside me.

I rubbed and rubbed until my whole body exploded. I knew right then and there, that Tom would have to be the one, to take my virginity.

***

The next day, afterschool, I went to Tom's apartment as usual. This time I wore a cotton dress, that came mid thigh.

"Tom," I said, "I wrote a poem last night. Would you like to read it?"

"You know I would." he said, as I handed him the paper.

It read:

I am an innocent, budding flower.
My petals have never been opened.
I have not been ready,
Until I met you.
Like the sun, you fill me with warmth.
Like the breeze, you chill my stem.
I do not fear the pain.
I do not fear the bleeding of my sap.
Say the word,
And my petals will open for you.

"Wow, that's quite a poem!" Tom said.

"Then will you?" I asked.

"Will I what?" Tom answered.

"Will you, be the one to open my petals?" I said.

"Well if you're talking about what I think you are, the answer is NO! I am your teacher and you are only fourteen. That would be wrong on so many levels." he replied.

"Have you ever had a virgin?" I asked.

"Not that it's any of your business, but no." Tom answered.

"Oh you will, you will." I said as I stood up and threw my arms around him, and gave him a big hug and passionate, open mouthed kiss.

Tom didn't have time to react, as I pressed my fourteen year old, 34D breasts into his chest. His penis reacted, however, and pressed into my crotch.

I broke the embrace, and left, leaving Tom to ponder what had just happened.

***

The next day I wore the same dress to school. It was very short and tight. When I sat down, it rode well up my thighs. I took a seat in the front row. Throughout class, I crossed and uncrossed my legs. From his angle, I'm sure Tom could see all the way up to the crotch of my panties. He seemed to be having a bit of trouble concentrating during the lesson.

On my way out of class, I dropped off another poem.

Virginity is a special gift.
One that is as good received, as given.
To receive a memory, one will never forget,
To receive a brief pain, to shape one's character,
To receive pleasure, beyond description,
And to receive the gift of womanhood, finally.
Give me the ultimate gift, and accept my gift to you.

I went to his apartment, afterschool, to see what he thought.

"I'm sorry Olivia," he said, "I just don't think we can do it. You're too young, besides, there are risks. You could get pregnant."

"That's not a problem." I replied. "I've been on the pill for six months. My parents are very liberal."

"You mean they're OK with you having sex?" he asked.

"Let's just say, they let me come over here, whenever I want." I answered.

"And I really don't think young is a big problem now, is it?" I asked, standing and twirling around in my dress.

"Well you are pretty in that little girl dress." he said.

"I know, and I can see that you find little girls sexy." I said, as I walked over and squeezed the growing bulge in his pants.

"I think we should see if there is anything else you like, before saying no to me." I continued. "See you tomorrow."

***

The next day after class, I dropped off another poem.

Cheerleader, Beach Beauty, Ballerina.
Everyman's fantasy. Everyman's downfall.
Panty, bikini, leotard.
Which makes you most hard?
Could these be the key?
To have you break me.

I arrived at Tom's apartment hauling my backpack. He was doing some paperwork. I was determined to lose my virginity by the end of the evening. The first thing I did was ask to use the bathroom.

I came out dressed in a cheerleader outfit I had borrowed from my girlfriend. It consisted of a short, pleated skirt, and a tight fitting tube top. I didn't know any cheers, so I just went over and talked to Tom. As I sat down, my skirt rode up past my thighs, and the crotch of my white, cotton bikini panties stuck out. My 34D breasts, pushed at the tube top.

"What's going on here?" he asked.

"Well if you don't want to take my virginity, maybe you'll take one of my friend's. Do you like cheerleaders?" I asked.

"Everybody likes cheerleaders." he answered.

"Have you ever sat in the stands and wondered what was beneath those panties? Have you ever had a cheerleader?" I continued. "You know, we all have a reputation of being loose." I stood up, bent my knee, and put my leg up on his seat.

I took his hand and put it on my thigh and moved it up to the crotch of my panties. "I'm not loose, at least this part of me isn't." I whispered.

Then I moved his hands, up to my breasts. "Have you ever wanted to feel a cheerleaders breasts?" I asked. "How about beneath their top?

As he reached under the tube top, I backed away and went back to the bathroom.

Returning a few moments later, I appeared in my favorite bathing suit. It was a red, skimpy cut, bikini. The bottoms were so small, they barely covered my pubic area. The top could barely contain my 34D breasts.

"Have you ever been at the beach, and fantasized about the young teen girls there?" I asked.

"Have you ever compared their cameltoes?" I asked sitting on the desk and spreading my legs.

"Has your penis, ever poked out the bottom of your trunks, just thinking about them?" I said, reaching out and rubbing his bulge.

Loosening the strap of my top, I leaned forward. One of the cups of my bra top lifted up. Have you ever wanted to suck a fourteen year old's nipple?" I said, pushing it into his mouth.

His lips clamped around me, as his hand reached for my crotch. After letting him rub me down there for a few minutes, I got up and went back to the bathroom.

This time I returned in a black leotard and white ballet slippers. The material outlined my pussy quite nicely and the thin material around my nipples, left little to the imagination.

Having taken ballet, I knew quite a few moves. I danced over to Tom, on my toes.

"Have you ever stopped at the window of a ballet school, and peered in at the young teen dancers?" I asked.

"Have you ever wanted to feel the firm butt of a dancer's body." I asked, facing backwards, moving towards him.

He reached out and started massaging my backside.

Turning around, I continued. "Have you ever wanted to press your chest onto a pair of leotard covered soft breasts?" I asked, leaning into him. As I did, I could really feel his penis digging into my crotch.

Pulling away and pointing the toes of my right leg, up to the ceiling, and putting my crotch in his face, I asked, "Have you ever wanted to know how a fourteen year old pussy tasted?"

Tom pulled me forward, and placed his mouth on my pussy, over the cloth of my leotard. He licked, pressing the cloth into my slit and landing at my clitoris on top.

"OK Mr. Cooper, I mean Tom, I'll ask you once more. Would you like to have a virgin?"

Tom didn't say a word, he didn't have to, he laid me on his couch, pulled the crotch of my leotard aside, and started to eat my pussy, for all I was worth.

After just ten minutes, I exploded in the biggest orgasm of my life, but I still didn't know what his answer was.

I found out shortly, as he reached up and peeled the leotard completely off. There I lay, vulnerable before him, with my breasts heaving upward, and my nipples as erect as little erasers.

There I was, a naked fourteen year old, my long legs spread open to his grateful gaze. My pussy was almost bare, with no pubic hair at all, like a preteen, yet my pussy lips were plush and plump, like those of a twenty year old.

Tom took a minute to strip. I finally got an up close look, at what I had only seen from afar. His penis, now erect, was at least ten inches long and a good two inches in diameter.

I reached out to feel it. I knew now more than ever, I wanted this penis inside of me, I wanted this penis to break my cherry, I wanted this penis to make me a woman.

"Are you sure you want to do this?" Tom asked. "It may hurt."

"Oh I want it to hurt, I want to know I have become a woman, I want to feel the pain turn into pleasure, I want us both to remember this forever." I shouted. "TAKE ME! BREAK ME! BREAK ME!"

Tom centered his penis over my vaginal opening and started to push forward. He immediately hit my hymen. After some gentle rocking back and forth, he pulled all the way out and pushed forward with all of his strength. I felt a sharp pain and then a burning sensation as he busted through my barrier. I let out scream, both of pain and relief, relief that I was finally a woman.

As Tom pumped in and out, I sobbed in pain. After a while, "Ouch, Ouch, Ouch!" was replaced by, "Oh, Oh, Oh!" as the pain turned to pleasure.

The head of his penis was rubbing against every nerve ending in my vagina. The top of his massive shaft was hitting my clitoris on every stroke.

I felt my vagina expand and contract in an almost continuous orgasm. Tom must have had some good stamina, for he continued to pump in and out, in and out for a whole half hour.

It was more pleasure than I could have ever imagined. Finally I wrapped my legs around his hips, and pulled Tom in as deep as I could. As I started another orgasm, I felt his massive penis start to throb, and then a hot wetness swept inside me.

He had cum deep inside my pussy. We lay there, coupled together, until his penis deflated, and popped out. A huge load of waxy semen followed, by a smattering of blood.

"Tom," I whispered, "did you like taking a virgin?"

All he could do was nod yes.

***

The next day, after class, I handed him another poem. It was short, to the point, and poignant.

Thanks for taking me, breaking me, and making me, A woman.

We made love, almost every day, for the whole school year. At the end of that time, he got a job in another city and I never saw him again.

And as they said, I never forgot my first, especially since his penis spoiled me forever...

More stories to come...