I could still recall Sean as an innocent, cherubic-looking grade nine student four years earlier. He would have been about fifteen at the time and in my friend Gayle’s home room that year. Even then he had a lovely quality about him; he was a gentle little kid, but already good-looking in a very nascent, undeveloped sort of way. By the time he reached grade twelve and enrolled in my elective art class, he had blossomed into a very handsome young man of eighteen. He was easily one of the best-looking students at the high school where I taught, but was too timid and soft-spoken to ever be a member of the ‘pretty people’ elite. Still, he always seemed to be in the company of pretty girls; all kinds of girls for that matter, and it was probably because he was among that rare breed of high school-age boys, the ones that had more girl friends than guy friends, that made him an object of suspicion among guys his age. The previous year, in grade eleven, he had been a constant companion of a very pretty grade twelve student named, Christine. They made a lovely couple, but the following September it was rumoured that the two of them had ‘broken up’. Student romances were, sad to say, always fun to observe from the sidelines — like some teenage soap opera that helped alleviate some of the boredom some of us teachers felt from time to time.
Classes started that September and my grade twelve art class was a nice group. I always enjoyed my grade twelves; being only a year away from ‘reality’ tended to make them a great deal more mature than grade elevens.
Stepping out of our ‘teacher shoes’ for a moment one day, Gayle and I observed how much of a ‘hotbod’ Sean really had become! Standing and giggling together conspiratorially in the hall, we watched him walk by on his way to class. He looked to be about 6’ 2”; slim with broad shoulders, and, ahem … quite a sexy-looking butt from where we were both standing. He had thick black hair cropped short, beautiful blue eyes, a gorgeous, and a smile that could melt your heart. It was then that I first heard of his ‘reputation’. Always the terrible gossip, Gayle whispered that she’d overheard a few of Christine’s girlfriends talking about how incredibly well-endowed Sean was.
“Apparently it’s absolutely HUGE,” she giggled.
We both jokingly lamented the fact that we couldn’t remember guys looking that good, and having THOSE kinds of reputations, when WE were in high school. Suddenly, as we were laughing, Sean seemed to hear us — he stopped, turned, and smiled in our direction. The two of us were a bit scared that he had overheard us — but then thought not.
My name is Jane, and at twenty-nine, I had been teaching art at the school for five years. I’d always enjoyed being creative, and although I never envisioned myself teaching art to high school students, I enjoyed it nevertheless. I had been separated from my husband for about a year that September, and my love life was still non-existent at the time. I had gone out on a couple of dates, but nothing had ever come of it. Gayle always teases me that my classes are full of boys who are only there to stare at my body. I’ve always laughed it off, but I suppose in a few cases she might have been right. I guess I would say that I’m a reasonably attractive woman, however immodest that may sound. But the real reason for my friend’s kidding, however, was the size of my boobs, which are quite large in relation to the rest of my body. I’ve been extremely busty since my own high school days and wear a 34HH size bra. Otherwise I’m a fairly petite 5’ 4”, 130 lbs; with dark brown hair and green eyes. I would be telling lies if I didn’t admit to noticing boys on more than a few occasions – no doubt hormones racing – staring at my chest.
This brings me back to Sean. That Fall I began to notice that he was paying me a great deal of attention — despite being quiet and rather shy. He was always extra attentive in class, asking questions, staying after class on several occasions, and even paying me compliments on what I happened to be wearing that particular day. He was quite the charmer, and I started to wonder if he wasn’t developing a bit of a school-boy crush on me.
The truth was I found him a pleasure to be around. He was a very talented sketch artist, and was so eager to learn anything I might be able to teach him. I could see that he was gifted with a tremendous amount of natural ability, and was a wonderfully creative young man. But looking back on it now, I realize that I should have been more honest with myself, because the REAL truth was that we were BOTH developing crushes on each other!
As much as I hate to admit it, and perhaps that’s partly why I wasn’t as honest with myself as I should have been, I was quickly falling for one of my eighteen year-old students. Not something you want known, even among your closest friends.
I don’t know if I was extra vulnerable because I was single and alone again after three years of marriage. I do know that I Kartal escort felt like a school girl all over again in his presence. I always knew where he was in the room. I was forever stealing glances at him from behind my easel during class. I even started wearing sexier things to work; miniskirts and tight tops. I found him so incredibly sweet and innocent — I felt an overwhelming desire to mother him; yet at the same time there was an undeniable sexual attraction. What made my heart REALLY go pitter-patter, however, was the fact that Sean seemed to be equally infatuated with ME. Sometimes the tension between us was unbelievably intense, and I didn’t have a clue where things were going. I DID know that I could get myself into a lot of hot water if I wasn’t careful. Still, something had to break. With each passing week, I was falling harder and harder.
One night, the two of us had been at the school ‘til fairly late; we’d been working on preparing an exhibit for the school’s upcoming fine arts festival. We were both ravenous, so I took the initiative and suggested we have dinner together after which I could drive him home. Sean blushed — then, ever the charmingly earnest one, used practicality as an excuse and agreed that we both needed to eat something. He also deftly skirted the fact that what was really happening was that I was asking him out on a date — my student, eleven years my junior!
That night marked the first time Sean had, at my insistence, called me by my first name instead of ‘Ms. Cleland’. It was unseasonably warm that evening, and I had the top down on my car as I drove Sean to my favourite Italian restaurant. My blouse was unbuttoned a bit, and the wind blew it open to expose my white lace bra. Turning to look at Sean, I noticed him glance at my cleavage. I felt an immediate wave of heat pass through me, and a dampness form in my panties.
As hungry as I was, I could barely eat; such was the electricity in the air between us that night. The waitress was about my age, which made me slightly uncomfortable at first — and for awhile I kept searching her face for a reaction to the fact that I was having what was obviously a romantic, candlelit dinner with someone much much younger.
We flirted all through dinner, had two glasses of wine each, and even succumbed to playing ‘footsie’ under the table. Sean kept blushing at my teasing and looked so cute when I insisted on picking up the tab. Just in case his parents found out about our dinner, I told him that it was for all his help leading up the festival. The truth was I wanted nothing more than to take him home to my bed, tear off his clothes, and have my way with him!
In the parking lot, Sean gallantly opened the driver’s side door for me. And as I moved towards the door, I was overcome with a bold instinct and reached up and kissed him on the lips. A thrilling current of lusty energy seemed to whip through our bodies; we kissed passionately for what seemed like an eternity. We were both trembling. But even in the heat of the moment, I noted that Sean was an excellent kisser. I tasted his young, full lips; his deliciously wet tongue.
Suddenly, seized by the craziness of what I was doing, I stepped back. Two simultaneously rambling, nervous and awkward apologies followed. Sean sweetly confessed his feelings for me; I avoided the issue by denying everything, saying that it was the wine and that I didn’t know what had come over me. I could see that he was hurt by this, and so for a moment I gently took his hand in mine.
I dropped him off in front of his parent’s house and raced home. One the way, I scolded myself for allowing such a predicament to happen. But at the same time, I was incredibly confused and had such mixed feelings. In a few short weeks I had developed strong feelings for Sean. I knew it was wrong, yet felt hopelessly incapable of cutting things off. The fact of the matter was that I was incredibly sexually attracted to him; I wanted so badly to make love to him. That night in the shower – softly teasing my clit with the pulsing water from the shower head – I fantasized about doing just that and experienced an incredibly intense orgasm.
A few days later I was in the local mall, treating myself to some new clothes — seeing as my birthday was soon approaching. I hadn’t seen Sean since the night of our kiss, but we had exchanged several telephone calls and e-mails — several of which were heartfelt declarations on his part. Though I longed to be as open with him as he was with me, I was worried that things had already gone too far.
I happened to be in a lingerie store and had just finished trying on a few bra and panties sets. I love buying lingerie, but am often frustrated by the fact that the really pretty bras are only made for women who are a size C-cup or smaller. On that particular occasion, however, I had found two really nice silk bras in my size with matching thong panties. One look at the price, however, and I quickly Kurtköy Escort decided to forego the expense. Then, just as I was stepping out of the change room I saw Sean standing there waiting for me. My heart leaped into my throat. As much as I was loathe to admit it to myself, I was thrilled to see him. He looked so sexy in his black leather car coat, black pants and tight grey v-neck sweater.
We spoke for awhile there in the store and the longer I stared into those beautiful blue, bedroom eyes of his, and went weak in the knees from his sweetly innocent smile, the easier it was to forget about the difference in our ages and the fact that I was his teacher.
He ended up walking me to my car, and I drove away feeling frustrated.
Over the next few weeks, things only intensified even further. It got to the point where I was slipping notes into his locker and he was chatting with me on the phone late at night while I was lying in bed.
One day, in the teacher’s room, two male gym teachers were joking amongst themselves about something funny that had happened that day. Curiosity got the better of me, so I asked them what was so amusing. They seemed reluctant to share the anecdote, and said that it involved a funny incident in the boys shower after swim class. Of course, that only made me more curious. Finally, after making me promise I wouldn’t repeat it to anyone else, they told me. Apparently there was a grade twelve student who had a reputation for being extremely well endowed, to the point where the gym teachers who had been witness to his physical ‘asset’ in the locker room had nicknamed him ‘Hugo’ (pronounced “Huge-o”). That day, a young girl from the girl’s swim team had accidentally wandered into the boy’s shower area just as the boy in question was rinsing off in the nude. The two of them came face to face, and, witnessing the size of his endowment, the girl shrieked and ran away. As they retold the story, one of the teachers inadvertently revealed the boy’s name — it was Sean! When I heard his name, I blushed every shade of red. Luckily, the two of them thought it was the story that had shocked me and not the mention of Sean’s name!
Having never really placed a great deal of importance on the size of a man’s penis before, I was surprised at my reaction. Initially, I had blushed because of the surprise coincidence and because I was afraid my feelings for Sean might be discovered. Later, however, I found myself daydreaming about the idea of experiencing a lover with a large sex organ. I confess that it only added to Sean’s mystique. I remembered a girlfriend once telling me how she’d once dated a guy who was very big, and how amazing their love-making had been once she’d gotten accustomed to his size.
It was definitely Sean’s charm, beautiful eyes, handsome smile, and lovely physique that I had found so irresistible — but his legendary ‘gift’ was nonetheless intriguing.
One night – it was my birthday, actually – having opted for a quiet night alone instead of dinner out with friends, I had made a fire and was sitting in front of it, relaxing with a lovely glass of chilled white wine, when the phone rang. It was Sean, and he said that he had something that he had to drop off that night. I said that it was alright, and he said that he’d be over shortly. I was thrilled, nervously excited, and anxious all at the same time. I took a quick shower, hurriedly put on some make-up, and applied a few drops of my favourite perfume in strategic places. I also lit a bunch of candles to create a sultry, relaxing ambiance.
About twenty minutes later, the doorbell rang. I answered it and there stood Sean, looking so adorable and sexy … with a dozen long-stemmed roses and a beautifully-wrapped present.
“Happy birthday, Ms. … I mean, Jane,” he said.
I was unbelievably touched! I didn’t know how he had found out, but at that particular moment I really didn’t care. Cooing with affection, I kissed him warmly on the lips.
“Come in, sweetie,” I said.
I took the flowers into the kitchen, put them in a glass vase, and returned to the living room with another wine glass in hand. Sean was sitting on the couch. I poured him a glass of wine and ‘kissed’ our glasses in a toast. The whole moment felt unbelievably romantic and sexually-charged. My heart was still all aflutter about the flowers when Sean presented me with the present. I think we both blushed, and I know I was beaming.
I untied the lovely ribbon, and proceeded to unwrap the present. Inside the box were both sets of expensive, silk bra and panties sets that I’d tried on that day in the lingerie shop! Though I was rather taken aback at the fact that I was receiving a gift of sexy lingerie from a teenage boy, I was still incredibly touched by his obvious thoughtfulness.
I asked him how he knew I wore a size 34HH bra, to which he responded that he’d gone back that day and had the clerk retrieve the ones I’d just tried on then returned. Maltepe Escort Again, it felt slightly bizarre realizing that one of my students knew what size bra and panties I wore! Still, I was overwhelmed by the gesture and leaned forward and gave him another soft kiss on the lips. One kiss quickly led to another, then another. Before I knew it, we were necking passionately on the couch. Suddenly, I realized I could feel a warm swelling in the front of Sean’s pants. I brushed against it with my hand and it felt impossibly large. But in the heat of the moment I didn’t really pay much attention.
“You’re so sweet, “ I cooed, “the least I can do is try on what you bought me and see if you approve. You’re a very bad boy,” I added, “You shouldn’t have spent so much money on an old woman like me.”
“I think you’re incredibly beautiful and not old at all!” he shot back with touching sincerity.
I smiled at him warmly.
Deciding then and there that there was no turning back, I went to my bedroom and quickly changed into the beautiful, purple silk bra and panties. The bra was a push-up and gave my huge boobs lots of support and mounds of cleavage. The thong panties were so comfortable despite being incredibly brief — the feeling of expensive silk against my pussy and breasts felt exquisite. I covered myself with my big, fluffy terry-cloth robe and returned to the living room.
I definitely had Sean’s attention. I took another sip of wine for courage and opened my robe to model his present.
I’m not sure what went through his mind as he took those first few looks at my skimpily-attired body. But there he was, feasting his eyes on the – if I may say so – voluptuous body of his high school teacher clad only in sexy bra and panties! His eyes widened noticeably when he saw for the first time just how large my breasts were.
“Well, what do you think?” I asked.
“You have an amazing body,” he stammered bashfully.
I snuggled up next to him on the couch. Taking his hand in mine, I kissed him sweetly once again.
“I think you have a beautiful body, too, Sean,” I answered. Then, staring into his eyes, I gently placed his hand on one of my heavy breasts.
“I’m not sure if you really know my feelings, Sean. The truth is, although I’m your teacher and am much older than you – speaking only as a woman – I’m very attracted to you” I said. “I hope that doesn’t make you uncomfortable.”
Sean swallowed hard. His voice was so small and timid-sounding.
“I really, really like you, too, Ms … I mean, Jane” he answered.
With one trembling hand still in mine and the other caressing my breast, I got up and led him to my bedroom. My heart was beating a mile a minute; I suspect his was, too.
I let my robe drop to the floor and began to slowly undress him. His whole body was shaking slightly. I stood on my tippy-toes and kissed him tenderly.
“Don’t be nervous, sweetheart,” I cooed with an almost motherly tone. “I promise I won’t bite.”
He was soon left with nothing but a singlet t-shirt (which I happen to find dead sexy) and a pair of boxer briefs. He had such a beautiful, toned body — smooth and sculpted; with a lovely flat tummy and a strong-looking chest. While Sean peeled off his singlet, I got down on my knees to give special attention to the enormous-looking protrusion in his boxers; one that seemed to extend along the entire length of his underwear!
I looked up into his beautiful blue eyes and then removed his last restraint. As I pulled down his boxers, the biggest, weightiest-looking penis I’d ever seen sprang forth!
“OH MY GOD, SWEETHEART!!!” I gasped. “It’s SO BIG”
Indeed, it was. In fact, I had never laid eyes on anything like it. It was still just semi-hard and yet appeared to be as big as my forearm; circumcised, extremely thick and smooth, with a large vein running along the shaft and a plump, plum-size head. It was mesmerizing and intimidating all at the same time.
I reached up and gently gripped it along the underside of the heavy shaft. It felt even bigger to the touch; so thick and fleshy.
“Christine must have been a little shocked when she saw you for the first time, too” I said.
“She was kind of afraid of it,” he answered shyly.
“Well, that’s understandable — she’s just a young girl” I said. “I think it’s beautiful — and very impressive. But it is also very very big, so we’re going to have to go very slowly at first, okay, sweetie?”
Sean nodded dutifully.
I stood up and we kissed passionately; groping each other with our hands.
I unhooked my bra and pressed my huge breasts against his chest. Sean’s enormous penis – hot and quickly hardening – was pressed against my tummy. The bigger it got, the more I began to question whether or not sex would actually be possible — if it doesn’t fit, then it doesn’t fit!
My large nipples were swollen and puffy, and my young lover played them perfectly — suckling and kissing them gently.
“You’re not so shy anymore, are you” I whispered.
I then sat him down on the edge of the bed and began to lovingly stroke his huge organ with both of my hands. His cock responded by expanding and hardening even further until it was a thick and hard monster.