Lola's First Letter

Dear Mr. Jameson,

I know this is kind of weird and kids don't usually write letters to their teachers anymore, but I just wanted to let you know you're appreciated. My aunt and grandma were teachers and they always complain about how unappreciated they felt, so I thought I should let you know that you're my favorite teacher. Before your class, I hated math, but you make it almost bearable lol. You explain everything really well without making me feel as dumb as I usually do in Math. Thank you so much for that.

Also, I wanted to tell you that I think you're super cute! From the first day of class, I noticed how hot you are. You're so tall and fit and handsome. You look so strong when you wear your fitted shirts on Fridays! OMG! I so want to squeeze your bicep whenever you're around me! I know this is so immature of me to have this schoolgirl crush on my teacher but...whatever! I can't help it! You're so sexy!

At least I'm being mature enough to tell you about it I guess. And I know this is kind of wrong and weird, but I just wanted to express myself somehow.

Love, Your New Favorite Student, Lola

PS. Don't tell anybody about this letter. Please! Please! Please! Don't tell! Our little secret!

The letter was signed in elaborate, flowing cursive handwriting with a heart for the "O" in Lola. Underneath the postscript was a wet, faintly pink outline of a pair of full little lips. Lola had accented her letter with a kiss.

I have to admit it felt good to be appreciated as a teacher and admired as a man, especially by a young, probably sixteen or seventeen-year-old girl. I would keep her letter a secret but wondered who had written it. There were no students in the entire school (that I knew of) named Lola, so it had to be a pseudonym. I figured it to be a good idea to keep my secret admirer anonymous. If a simple letter made it sound so alluring to have a young paramour, I couldn't risk what I'd do if I met the doting girl.

A month later, just when the stimulating effects of the first letter and the knowledge of my young admirer began to fade, Lola sent another letter, this one bolder.

Lola's Second Letter

Dear Mr. Jameson,

It's me again, your super secret admirer. I wanted to let you know that you're still always on my mind even though I have a boyfriend now. But don't be jealous, if I could, I'd choose you over him in a heartbeat! And I'm not sure it's gonna last anyway. I think all he wants is sex. Ugh, is that all boys ever think about?

No need to worry though, Mr. Jameson. I'm a virgin and I plan on staying one for a long time. I'm saving myself for my favorite teacher! Just teasing! Well, Mostly... To be honest, I still think you're hella sexy. Everything about you turns me on. The way you command the classroom, demanding our respect. The way you show that you care about us by being nice but also kind of tough. And when you get close to me to help me with my work, I get so hot! I can't stop stealing glances at your sexy body.

My boyfriend is handsome but he has absolutely nothing on you. I so wish I were your age or you were mine. Or that certain laws didn't exist. Oh, I wish I knew what you thought of me! But I'm so scared to tell you who I am. I guess I'll have to settle for writing my letters and living out the fantasies in my mind.

Yes, I fantasize about you! At night, I think about your lips on mine. I think about your hands on my skin. I think about your strong arms all over my body, embracing my tight, curvy frame. Sometimes I even think about you undressing me and putting your hands where they don't belong! Oh, it makes me so hot I have to touch myself. It's all I can do to satisfy my craving for you.

OMG! I've said too much. I probably shouldn't send this.

Love, your horniest student, Lola

The letter was signed in the same way, with a heart for an "O" and a pair of pinkish, translucent lips that smelled of strawberry. After reading the letter, I wasn't surprised to notice my cock had gone erect. I convinced myself I wouldn't do anything untoward, but I had to find out who this girl was.

It didn't take too long to figure it out. At first, I monitored the reactions of girls I would help in class, trying to detect signs of nervousness or admiration. That provided me with a list of several suspects. It turned out I had the same effect on many a teenage girl. The biggest clue as to my secret admirer's identity hit me right in the eyes when I wasn't expecting it. A student, Brandy Sherwood, decided to apply lip gloss to her already moist and lustrous lips, pursing them together and kissing the air. Only then did I realize I'd watched the cute, cognac-skinned girl do it half a dozen times before. I was all but sure I'd found my girl.

I watched her over the next couple of days and she gave no tell. Not in her reaction and demeanor anyway, but I did get close enough to acquire the scent of the strawberry gloss that coated her pretty lips in a pink, transparent gel. It was the same fragrance from her letters and I could imagine her kissing the paper with those luscious lips, thinking of me.

I checked her student profile on my computer, seeing that her middle name was Delores, the name from which the nickname Lola comes. I'd scoured my attendance list before, checking the profile of every girl in my classes with the middle initial L. There were no girls with the middle name Lola or anything close to it. It'd never occurred to me to check for Delores.

Having confirmed the identity of my young sweetheart, I started paying more attention to the girl. Brandy was an understated brown beauty, her skin the color of smooth, strong liquor and sweet honey. She wore her deep chocolate hair in an African style, her natural curls a wild, kinky frizzle. Her eyes were an inviting warm brown, whispering of sweetness, chastity, and innocence. Her dress was almost always modest, long skirts with stockings or tights and wool sweaters on top of neat blouses. Very classy.

Brandy was a little bit of a nerd but by no means was she a shy girl. She had groups of friends and she talked and laughed often, her lively eyes dancing with mirth, her deep dimples accenting her pretty smile. As I observed her, I found her to be a particularly popular girl. It was clear to me that she could have any boy she wanted, for she attracted the not-so-subtle attention of a diverse cast of them as the weeks progressed. Why she was crushing on a plain (albeit handsome) white Math teacher twice her age was beyond my understanding. It did not, however, escape the grasp of my ego.

The things she'd written, I would have said, belied her chaste, casual demeanor. But really, who doesn't have a secret sexual side? And Brandy's sexual side belonged only to me. Popular Brandy was known by everyone, the students, the teachers, and the administration. They all only knew Brandy the intelligent, witty, friendly, funny, and mild-mannered young girl her parents had raised. But I knew Lola, a young girl caught up and captivated by her blossoming sexual desires. And I was secretly, completely enamored with her.

Her third letter, sent to me just before Christmas break, simultaneously whet my apatite for Lola and roused jealousy I didn't know I harbored.

Lola's Third Letter

Dear Mr. Jameson,

I don't know who to talk to right now. Or, I guess, I don't want to talk to anyone, so I'm writing you. Strangely, I feel like you are the only one who really knows me. Like I can show you parts of myself that no one else will ever get to see. It sounds weird even to me, but I think you would know just the right thing to say to me right now. I wish I wasn't such a wimp so I could talk to you.

I just feel... I don't know, cheap, I guess. Not like a slut or something but I feel let down. I just had sex with my boyfriend and it was not at all what I envisioned. It was over before it even started to feel good. It was so quiet and sneaky because he didn't want his parents to catch us. He kept shushing me the whole time. And he sent me home before I got a chance to talk about it. Kevin's not a bad guy, not really. He's a really nice boy but, I don't know if that's what I want. I don't think he even knew what to do with me. It was my first time and it didn't even hurt. It was like he was afraid he was gonna break me or something.

I'm sure you would have known what to do with me, Mr. Jameson, wouldn't you? You do when I fantasize about you. I wonder how you would have made love to me. I think you would have pressed me against a wall and kissed me for a long time to get me all excited, your hands caressing me all over. When I moan, you start to unbutton my blouse. I'm shaking so much but I let you take off my top because you know what you're doing. I trust you.

You tell me I'm beautiful, whispering in my ear as I stand in only my bra and skirt. You take my hand and put it between your legs. I gasp as you make me massage your big dick. It comes to life in my hand. I moan softly. You groan in my ear. My panties are soaking wet. I quiver when you slide your hand up between my thighs. I flush with embarrassment as you react to my arousal.

You massage my pussy through my panties as you kiss my neck. I rub up and down your long, hard cock through your slacks. So thick. So alive. It turns me on. I want to touch the real thing. Your kisses go down from my neck to my soft, heaving chest and you lick me in between my breasts. I gasp when you squeeze your big strong hand inside my bra cup and pull out one of my titties. I squeeze your big dick when you take my nipple in your mouth and suck it so hard it hurts. You peel my other cup down off me, and now both my titties are exposed and you kiss and lick them. I'm giddy and nervous and horny.

You can tell by how frantically I'm grabbing and rubbing your cock that I need to feel it in my hands. You loosen your belt fast and unfasten your pants faster. I gasp when I feel your hot, white, throbbing cock in my hand. It's so big and hard! My wet panties suddenly feel like a nuisance as you massage my young, hot pussy through the soaked cotton, and I silently pray that you relieve me of them. You read my mind and excitement pulses through my heart as you slide my white panties down to my knees.

When you slip your middle finger inside my coochie, I quiver as I cum. It feels so much better when you touch me than when I masturbate. I nip my lip and my eyes roll up in my head as you slide your finger up inside my tight, wet pussy again and again and again. You kiss me as I climax, pressing me against the wall as my knees turn to water. You make me taste myself off your sticky fingers. I indulge.

Your hard, heavy cock is still in my hand and I silently beg you to put it inside me. You read my mind again, because you know I'm such a horny girl. You command me to turn around. I obey. My panties drop from my knees to my feet as I turn around and place my hands on the wall.

You lift my skirt and press your hips against me so I can feel your throbbing cock against my butt. I don't know how your big dick is gonna fit inside my tiny pussy - even one finger felt snug in my hole - but I know I want it so bad. When you put it in me, it stretches me. Still, you slide your long cock all the way inside me. You feel so big and I feel so tiny as you take me. It hurts and feels so good at the same time. As you fuck me hard, I scream and cry and whimper as loud as I want. We both cum at the same time, you filling me up as I crumble into pleasure.

Oh God, Mr. Jameson. Thinking about you makes me so horny. I'm so wet right now. I wish it was you who took my virginity instead! I have to stop writing now. If I don't make myself cum right now I think I might die!

Always thinking of you, Lola

The letter was again stamped with the gel of her perfectly shaped lips.

I was awestruck, trying to sift through a mix of emotions as I reread Lola's letter. She had given a part of herself away that I thought belonged to me. How could I ever think this teenage girl's sex belonged to me in the first place? And then there was her fantasy about me. My God! My cock grew hard just reading it and imagining what her body looked like underneath all those layers of clothing. What it would be like to undress her, feel her, take her. I suppressed my guilt as I built my own fantasy sex scene with Lola, telling myself they were just fantasies, and that I would never do these things in real life. I contemplated writing her back but thought better of it.

During the two weeks of Winter break, my mind kept returning to Lola. As the excitement of her sexual fantasy waned, the tinge of jealousy rose to the surface. I knew I had no right to it but there it was, taunting me, telling me that I should have pursued her after I received her first or second letter. I could have had a flower-fresh virgin all to myself but I blew it. Then I'd berate myself for even entertaining such an immoral thought. I was her teacher and twice her age. How could I regret missing out on a sexual relationship with a girl so young, a girl her parents trusted me to mentor and protect?

I should be responsible, I thought. I should tell her she can't be having these fantasies about me, and that she certainly can't be writing to me about them. If my daughter were crushing on her teacher, I'd want him to set her straight, not indulge in the forbidden fantasy. This was but one of the many conclusions I'd drawn over break. I have to admit that Lola, or rather, Brandy, had me somewhat confused.

When school resumed, I was much more in control of my thoughts. Though my mind remained on Brandy, the contents of those thoughts were a bit more chaste. I still felt a sense of pride that I could draw the desire of such a beautiful young lady but felt confident that I wouldn't do anything inappropriate. During the second week back, I was grading quizzes. After grading Brandy Sherwood's quiz, a smirk surfaced on my lips as I looked over her excellent work. I felt proud that I'd taught her well and proud that we shared a sneaky secret. I had no reservations about writing on her paper, 'Awesome job, Lola!'

When I returned the quizzes, I watched as Brandy's proud smile transformed into a shocked expression. Her eyes flicked up to mine and I smirked at her very briefly before turning away to finish passing out the papers. She said nothing for the rest of the class, wearing a blank, worried expression. When the bell rang, she was the first to exit, striding out of my classroom with urgency without even sparing me a glance. Only then did I consider the fact that she'd said in her letters that she was afraid to reveal her identity. She must've been embarrassed, or worse, afraid I'd take advantage of her. I felt guilty.

Thankfully though, she came to visit me after school the same day. I was cautiously pleased to see her.

"Mr. Jameson," she said and hesitated, "Umm... About those letters...I don't want you to get the wrong idea. I... I'm not really like that. I don't want you to think I'm some weirdo stalker or a slut."

"No, I don't think that," I assured her.

"I mean, you are my favorite teacher. And I do think you're really good-looking. But all the other stuff... The sex stuff... I just wrote it in the heat of the moment, y'know? And I only sent them because... Because... Well, I don't know why I sent them." She began to look increasingly nervous.

I smiled reassuringly. "It's okay, Brandy. I get it. I had crushes on a couple of teachers when I was in school. And believe me, if I wasn't terrified I would have let them know how I felt too."

Brandy relaxed some. "Right... Right." She took a deep breath. "And, Mr. Jameson, I didn't expect you to like...do anything about what I wrote. I didn't even think you would figure me out."

"So, why did you write those things in the first place?" I asked, successfully keeping the disappointment out of my tone, replacing it with genuine curiosity.

"I don't know. I think I just wanted to express myself. You know they say teenagers are all always horny." She giggled sweetly. "I think I just wanted to explore that part of me...and to let someone else see that part of me too. I know, it's stupid." A cute, coy smile threatened to spread across Brandy's lips.

"It's not stupid," I said. "I think it's a healthy way to express yourself. And you're pretty talented. I could visualize...uh, I mean, uh..." Brandy laughed at my discomfort. "I just mean that your writing skills are pretty advanced."

"Thank you, Mr. Jameson," she beamed. "I'm glad I came to talk to you. I didn't know what you would think at first. But you're pretty cool."

I smiled. "As are you." She extended her hand and we shook, a bit formally, beaming wide smiles at one another. God, she is cute, I thought as I shook her soft hand longer than necessary.

I released her and she turned to leave. "Bye, Mr. Jameson," she said, pausing at the door to turn and wave.

"See you tomorrow, Lola," I said happily. Her face suffusing with glee, Brandy gave a coquettish smile, nipped her lip, and curtsied prettily before proceeding down the hallway. It was the cutest thing I had ever seen. My heart glowed.

A relationship grew from there. A platonic relationship. Brandy became almost like a little sister to me. She'd visit me in the morning before my first class every day, and most days after classes had ended. We'd talk about everything and nothing, about high school and college, relationships and sex. I told her about my estranged wife and the events that led to our separation. I'd give her advice whenever she was going through with her boyfriend, who she eventually broke up with. She asked my opinion about another boy and only began to date him after I gave my approval. We were friends, I realized as the weeks passed.

Brandy was much more mature than her years. She spoke like an adult, thought like an adult, and reasoned like an adult. She respected the boundary between us and didn't attempt to cross any lines. However, she did flirt with her eyes or with a few, slick words from time to time. And the scant few times that she hugged me she held me long and tight, the feel of her young, soft body and the scent of her curly hair captivating me, causing me to look forward to her next letter.

Yes, I continued to receive letters from Lola. They grew frequent and increasingly graphic as the months progressed. This young girl had a dirtier mind than most grown men I knew. She wrote of how she'd just love - not like, not want, but love -to suck me off. She fantasized about my fingers going in each orifice and my cum leaking out of all three of her willing holes. Lola's mind was a sexual playground, filled with leashes and handcuffs, vibrators and anal toys, deviant roles, and sexy games to play. But when I talked to Brandy, she was all sweet and chaste. If only she knew how badly I wanted to join her in her salacious fantasy world and fulfill every perverted desire her alter ego had shared with me.

I attributed the increase in Lola's apparent horniness to the change in weather. As the sun shined longer and hotter, raising the temperature and foreshadowing summer, the teenage libido grows ravenous. This was evidenced not only by the frequency and intensity of Lola's love letters but the way she dressed. Wholesome, full-length dresses, skirts with stockings, long-sleeved blouses, and sweaters slowly transitioned to more revealing attire. I feasted on the lustrous brown skin revealed beneath the hemline of medium-length shorts and ogled the curve of her swollen breasts beneath thin tops.

One day, Lola had gone without a bra, greeting me with a smile and her two, fine nipple points first thing in the morning. She had to know what she was doing to me, smiling and flirting with her eyes as the tips behind her thin top tightened, her two, stiff nipples imprinting the soft fabric. Midway through the day she was called down to the principal's office over the PA system. When I saw her later, I couldn't make out the shape of her enticing nipples at all, no matter how hard I tried. After school, she told me that Principal Mackie made her cover her nubs with bandaids. I wasn't aware they still did that.

Our relationship became very comfortable, but for the most part, platonic. That was until the day she was sent to after-school detention...