Tiffany’s First

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– Chapter I – Introduction –

I woke up on a Tuesday morning. I was so excited because it was my first day of my senior year in high school. I couldn’t bring myself to take out the long braids I always wore in my hair. I had decided on a short plaid pleated skirt and a white top. I liked wearing button tops now that my breasts were almost fully developed. At eighteen I was wearing a full b-cup. The bra and panties I wore were the ones I had bought at Victoria Secrets. I saved up the whole summer so I could buy my lingerie from there. I slipped on my canvas shoes and left for school. Mom wouldn’t allow me to wear make-up so I had to wait till I got to school to put it on. I was sneaky about that but it was a special occasion. My history teacher was going to be Mr. Yeoman.

I had always known him as Uncle Matt. He wasn’t really my uncle. My brother was twelve years older then myself. Brian and Matt had been friends since before I was born. I grew up tagging along and bugging the two of them. But when they went to college, it changed. Matt was going to be a teacher and Brian was going for business. I was only six when they left. They graduated from college when I turned eleven. I was just beginning puberty. My body was changing. Then out of nowhere I noticed how handsome Matt was. He got his masters over seas in England. He was there for only two years studying and teaching. But that was enough time for him to develop an accent, which hasn’t lessened since his return to the states. He took a position in my school district last year. Instantly the female attendance in his class became perfect. He was cute, funny, and smart. Even the junior-high girls dreamt and talked of him often. I was the envy of all because I knew him. He came to my house often to visit Brian when my brother was in town. I was lucky enough to have him kiss my cheek when he arrived. He would tell me how grown up I was becoming. He told me how pretty I was and how he just loved my braids. But he had no idea that I dreamt of him. He had no idea how big my crush for him was.

I walked into the school and saw Matt standing by the teacher’s lounge door. He was speaking to some of the faculty when he noticed me come in.

“Hello Tiff, how are you today?” Tiff was his pet name for me.

I walked up to him and scolded, “Mr. Yeoman, I told you to call me Tiffany.” We had already spoken about boundaries at school. He was supposed to treat me as a young lady and I was suppose to remember not to hug him and kiss his cheek on school grounds.

“Oh yes, I am so sorry Tiffany. You’re in my American History class 8th period.”

“I know. You told me last week. Easy ‘A’?”

“No. You’re going to have to do twice the homework.”

“Not funny.” The bell rang and I rushed to get to homeroom.

The day went pretty fast. Before long I was sitting in the front row of Mr. Yeoman’s class. I was sure to be in the middle of the front row. The day had apparently been a little tough for him because his tie was loosened and his sleeves rolled up. He was a little over six foot, short blonde hair, thin, and an incredible dresser. He looked so good. But the most handsome thing about him was his face, or rather his eyes. He had a strong jaw line and perfect lips. But as I’ve mentioned, it was the eyes that the girls talked about. They literally changed color. Depending on what he was wearing and his mood his eyes went from a brilliant blue, to green, to grey. He taught with enthusiasm. Most teachers gave us names and dates, but he gave us stories and excitement. What gave me the most excitement was watching him walk across the classroom. His ass was perfectly round and proportioned. The pants he wore made the most of it by hugging it just enough to let me imagine the rest.

– Chapter II – A Tease –

I guess some time during my panting I let my guard down. By the end of the class I found that I had uncrossed my legs. But the thing that pleased me was that I noticed Mr. Yeoman glanced down to have a peek. Is it possible that he was beginning to see me as something other than a little girl? Did he just accidentally notice my legs uncrossed or did he look purposely to see if I was wearing any panties? The bell rang and I grabbed my books to leave.

“Tiffany?” He spoke.

“Yes Mr. Yeoman?”

“I wanted to speak to you for a second.” He said as the classroom cleared. We were left alone.


“Now that the day is over, would you like a ride home?”

“Yes, thank you. Can I call you Matt now?”

“Sure Tiff, now let’s get out of here.” We walked to his car. He drove a 1998 Mustang Convertible. I loved it. He opened the door for me as I untied my hair and let the braids unravel. My hair was down to my waist and wavy from being braided all day. He got in the car and stared at me for a second.

“What’s wrong Uncle Matt?”

“Nothing. I just hadn’t realized how beautiful you’ve become.” I blushed. He had always called me pretty but never beautiful. We pulled out of the school parking lot. My şanlıurfa escort skirt flew up from the wind. Matt’s eyes dropped to my legs. I shyly pulled it down.

The next day I wore a black mini-skirt but this time I skipped the panties. Eighth period came and I sat in my usual seat. Ten minutes into the class I purposely uncrossed my legs and opened them wide. Just as I expected he looked. Well, he looked almost through the whole class. The following day, I wore pants but this time I unbuttoned my shirt to the middle of my chest. He looked again. I always acted as if it was by complete accident like I was an innocent that wasn’t aware of my own sexuality. But I knew how to attract his attention. He never mentioned anything to me and aside from the occasional ride home, we were never alone. The whole semester continued like that until Christmas break.

I went to the Christmas dance with Bobby. I wore this pink dress and heels. Mr. Yeoman was a chaperone. Half way through the dance, Bobby starts dancing with Vanessa Marsh. He ignored me the entire night. I sat on the stairs outside the gym crying. My eyes red from crying and my head lying on my knees, I felt a hand rest on my shoulder. I lifted my head to see Matt standing there. “Are you okay Tiff?”

“Men are scum.”

“Ohhh, Bobby. Yes I saw him dancing with that stupid, pimply-faced girl.” I just smiled.

“If she is so ugly, then why is he with her?”

“She probably puts out.” He smiled. He could make me laugh.

“Maybe I should put out then.”

“No you don’t. You wait for someone special.”

“How will I know when it’s the right time?”

“When you’re in love and you’re thirty.”

“That’s old.”

“You only say that because you’re so young.”

“I’m not that young. Tell me, Matt. Is sex that important to boys?”

“Well, it depends on the boy. Someone who loves you and respects you will be more concerned about it being the right time for you. Someone like Bobby is more concerned about what his friends want him to do. Forget about it.”

“What does it feel like?”

“What does sex feel like?”

“Yes, if you don’t mind telling me?”

“Well, when it’s wonderful it can be an incredible experience.”

“And when it’s not?”

“For women especially, it can make you feel cheap and embarrassed. Make sure it’s wonderful for you. Okay Tiffany?”

“Okay, Matt.”

“Hey? Guess what?”


“I’m staying at your house for Christmas.”

“Really? That’s wonderful. Why?”

“Well, Brian is bringing home his fiancé and he would like me to stay there. My family is going to be in Europe so it’s great to be spending time with my second family and my favourite little sister.”

“I’m not so little anymore.”

“I know.” He smiled a bit like he was recalling the games I had played all year so far.

– Chapter III – A Dream –

Christmas week came and I was overcome with excitement. Brian was coming home that day and Matt was on his way over. I dressed especially for him. I braided my hair and put on a pair of leggings and football jersey. He loved Penn State so I had an ample supply of their apparel. There was a knock at the door. I ran as fast as I could. I opened the door to find all three standing there. “Brian! Matt! Felicia!” I jumped into their arms and kissed each one.

“My baby-sister. Oh, I’ve missed you.”

“I’ve missed you. Let me see the ring.” Felicia lifted her hand to show me the 1/2 carat diamond Brian had bought her.

“You’ll be a bridesmaid, right?” She asked.

“Oh yes! I’d love to.” I always wanted to be a bridesmaid.

“Don’t forget about me.” Matt was talking to me just like he always had.

“I’m so happy you’re here, Matt. Come in.” They came in and brushed the snow off their coats. Matt grabbed a chunk of ice and looked at me deviously. “No Matt! Don’t even think about it!”

“Come here Tiffers.” “No way!” I said as I ran towards the kitchen. He chased me. I got to the table when he caught me. Kicking and punching I fought him off but to no avail. He tackled me to the floor and the snow slid down my neck into the cleavage of my bra. I got up screaming and dancing around as I struggled to relieve myself of the intense cold. I guess in the excitement of it all I must have exposed my bra a bit because Matt was sort of staring at me with this shocked look on his face. We just started laughing to break the tense moment.

We spent the next few hours with all of us talking about Brian’s wedding. We had just six months to plan the whole thing but honestly I wasn’t paying attention to any of it. I couldn’t help but watch Matt the entire time. He did this thing with his fingers rolling his knuckles one after the other. He would stop for a second to flash me those eyes. I had never seen that look from him before. It affected me in a way I had never felt before. I went upstairs to change and listen to music. Before I knew it, it was one in the morning. I was always a night owl. I crept downstairs to get a drink.

I wore a black chemise. I figured everyone was sleeping so I didn’t bother to throw on my robe. I walked into the kitchen and opened the refrigerator door. “Who’s that?” I heard a voice ask.

“Tiffany.” I answered. A figure stepped out of the darkness. It was Matt.

“Tiffany. Shouldn’t you…” he paused as he looked at my body. He shook his head as if he was bringing himself to his senses. “…You should be in bed.”

“No. I always stay up late.” He just kept staring. I was positive now that he did see me as more than Brian’s baby-sister. Seeing him in his silk pyjama pants made me want him more than ever. I wanted him right then and there. “Matt, can you do me a favor?”

“Sure Honey, what do you want?”

“Keep me company for a while. I have some homework I need help on. My tyrant of a history teacher gave us an assignment due when we get back.”

“Well, he must be a real bastard. What are you working on?”

“Civil War…” We walked upstairs as we talked about the assignment. I opened the door to my bedroom and invited him in. He had been in my bedroom a thousand times and thought nothing of it. I noticed the deep breath he took as he walked into my room this time. It was going to be different.

Chapter IV – Seduction

We walked into the bedroom. My book-bag was in the corner of the room. I bent over to pick it up just right so Matt could see my ass. I wasn’t wearing any panties. I stood up and carried my notes over to him. “Now Mr. Yeoman. Would you help me with my paper?”

“Why yes, Tiffany. Let me see your notes.” I handed them to him bending over just enough so he could see a bit of my breasts. We sat on my bed. My room was so girlish. I had a double canapé bed with pink ruffled comforter. There were stuffed animals and dolls everywhere. He looked so out of place sitting on my bed. His bare chest and arms were accentuated as he placed his elbows on his knees reading my notes. “God Tiffany, I can barely read these. You need to write more legibly. It will make studying easier.” He pushed his gold-rimmed glasses back from the tip of his nose. I sat beside him pulling my feet up to my chest. I purposely slid the skirt of my nightie down to my hips. Matt noticed this but I just went on.

“Take off your glasses, Matt. I’ve never seen you without them.”

“All right.” He took them off. His eyes became a brilliant blue.

“Your eyes are even more beautiful then I imagined.” I said as I turned to him. I looked straight into his eyes.

“Why thank you, Tiffers.”

“Don’t call me that!” I became irritated. “I’m not a baby. God, Matt, what’s wrong with you? Don’t you think I’m sexy?”

“I’m sorry, Tiffany.” He gently put his hands on my shoulders. “You’re so young. I can’t think of you like that. But yes, you are beautiful.”

“But not beautiful enough for you?”

“You’re too young.”

“But I want you.”

“You don’t even know what that entails, Tiffany. Is that why you’ve been doing those things in class?”

“What things?” I said in a baby-doll voice with an innocent look.

“You know. Now that could get you in trouble if it was with any other man. You are quite beautiful.”

“And you’ve enjoyed the view, haven’t you?”

“No, I’ve been avoiding looking at you when you do that. I thought it was just an accident but now I know different. I need you to stop that.”

“So you don’t like what you see?”

“I haven’t seen anything.”

“Oh really?” I stood up and slipped off my nighty. “So what do you think?”

“Tiffany!” He turned his head. “Please, get dressed.”


“You have no idea what you’re asking for.”

“I want you to kiss me.”

“When you’re like that, you’re asking for more then a kiss.”

“What then?”

“You’re asking me to make love to you.”

I lifted his head to look at me. “Then make love to me, Mr. Yeoman.”

His face changed. He stood up and wrapped his arms around me. “Are you sure this is what you want?” He grabbed my head and kissed my lips hard. It was my first real kiss so I wasn’t quite sure what to do. Our lips parted and his tongue slipped into my mouth down my throat. I did the same to him. He pulled away and looked into my eyes.

“Yes, Mr. Yeoman. Teach me how to make love and tell me what to do.”

“Then later you will learn exactly what my tongue can do.” He turned and threw me on the bed. I could feel my pussy getting wetter and wetter from the sheer anticipation of his body on top of mine. He stood above me as he took off his pants. I stared at his body. He was long and thin. His cock was stiff and bigger than I had ever thought a man’s cock was. “Are you sure you want this?”

“Tell me what you want me to do.” I said as I spread my legs for him. I was a little scared but curious.

“No, Honey, we don’t start with that. This is going to last all night. Now come here and touch this.” He ordered as he stroked his cock.

“Yes Mr. Yeoman.” I said as I sat up and touched him for the first time. His cock was throbbing and hard. The tip was covered with a liquid. He pushed my head down until my face was right in front of it.

“Now, I want you to taste it, Tiffany. Open your mouth.” I obeyed. “Now I want you to suck on my cock.” Not sure how to please him, I took his cock into my mouth. He grabbed my hair and moved my head back and forth. I sucked just like he told me to. He moaned and called my name. “Tiffany! Ohhh Tiffany! That’s right. Just like that.” I continued for a while then suddenly he said, “Stop.”

“Did I do something wrong?”

“No Honey,” he stroked my hair gently. “I want to touch you.” He laid me back on my back and began to kiss my neck. Desire stirred up inside me. My body reacted in a way I had not experienced. His hands went further down to my breasts. He caressed them right before he took me into his mouth. He sucked and bit each nipple. He moved down further to my stomach. His hands gently parted my legs as his mouth moved down further to my pussy. I wasn’t sure what he was about to do but I trusted him. His tongue tickled my clitoris.

It was like nothing else I had ever felt. His mouth barely touching he gently sucked and licked my pussy until my back suddenly arched and my entire body tensed. “Ohhhh Matt! I… I… I can’t move…”

“You’re coming, Tiffany. That’s the first of many orgasms for you tonight.” His hand reached up and grabbed my wrist. “Do you touch yourself?” He pulled my hand to my pussy.

“No of course not.” I was lying.

“Don’t lie, Tiffany.”

“Yes, sometimes.”

“Have you ever felt your pussy this wet?” He pushed my fingers inside me.

“No. Never.”

“Have you ever made yourself come?”

“No. I never have.”

“Well you will tonight. I want you to masturbate now, Tiffany.”

“No. I can’t do that.”

“Do as I say!” He ordered me. I obeyed as I put my fingers in and out of my pussy. “No. Not like that. Stroke your clit, Honey.” I massaged my clitoris with my fingers. He was right. That was better. “Lightly, Tiffany…… that’s it. Just like that. How does that feel?”

“Feels good, Mr. Yeoman.”

“Faster, Tiffany, here let me help.” He slipped two fingers inside me and moved them back and forth fast and hard. I could feel the orgasm building up inside me like I was about to explode. Then all of a sudden it happened and my pussy tightened so much, he couldn’t pull his fingers out of me. “Oh Tiffany. You are so tight. Are you ready to make love now?” I nodded my head unable to speak from coming so hard. “All right then. Spread your legs wide.”

I was a gymnast for a long time so I was quite flexible. I opened my legs into a split. He knelt over me for a few moments stroking his cock. Then he laid above me holding his body up with one hand and holding his cock with the other. He kissed my gently and whispered, “Now it might hurt a little at first, Tiffany. Tell me if it does and I will be more gentle.” With that I felt the tip of him push against my pussy. I got scared all of a sudden and tensed up. He stroked my hair and said, “Relax, Tiffany.” I took a deep breath and relaxed. Slowly his cock entered me. I was so tight that the pain radiated through my body. He must have seen the look on my face because he stopped half way in and asked, “Are you okay? Do you want to stop?”

“No, Matt. I want this. Please don’t stop.”

“Okay Sweetness.” He kissed me. He plunged his cock all the way inside me and began moving in and out. His cock pushed against the very bottom of my pussy. Passion overcame my pain as I moved with him. He pushed harder inside me and faster all the while sucking my breasts and caressing my body.

He rolled us over and pushed me so I was sitting on top of him. He grabbed my hips and urged me to bounce up and down while grinding my pussy. His cock moved around inside me. I cupped my breasts as my back arched completely until my head hit his knees. His hands clutched my waist as he realized I had lost control of my body. He picked me up and threw me on the bed once more.

Forcefully he plunged his cock inside me. It hit so hard that I did not know if it was pain or pleasure that I was feeling. Again and again, harder, faster he fucked me. His hands clutched my shoulders as he thrust inside me. I came time after time until I seemed in a constant orgasmic state. I couldn’t move so I let him do what he wanted as fast as he wanted. “I’m going to come now, Tiffany. And I’m going to come all over you.” He said with a few strong, deep stokes then he took out his cock and stroked it until hot, whitish liquid exploded all over my breasts, stomach, and pussy. Matt whipped a bit off my stomach with one of his fingers and put it into my mouth. “How do you like the taste of that?” He asked like he wasn’t looking for an answer. I smiled.

Matt grabbed a towel from my bathroom and covered my body with it. I had bled a bit through it all. I wrapped myself in it as he laid next to me and held me in his arms. He kissed my cheek lightly. “Are you all right, Sweetness?”

“That was wonderful, Matt.” I said as I turned to curl up in his arms.

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