Toy Boy Ch. 01

Story Info
Teacher Jenny bumps into ex-student Michael in the street.
3k words
4.31
39.7k
29
5

Part 1 of the 6 part series

Updated 09/25/2022
Created 07/24/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I wanted to try a different perspective for this attempt. Plus this takes things much slower, and is about as realistic as I could make it, whilst staying in the "erotic" genre of course. My initial thought was to write this as a two-sided "he said, she said" type thing, but I got too engrossed in the one side of the story, and so never bothered with the other side. Anyway, I hope you enjoy this humble offering.

Teacher Jenny bumps into ex-student Michael in the street, twice, and decides to seduce him by dressing to impress.

Chapter 1 – A Chance Meeting

Michael was a geek. There was no getting round it. I had arrived at the school as a newly qualified teacher fresh out of university the same year he had arrived at the school as an eleven year-old boy. I had hardly noticed Michael for those first couple of years or so. All puppy-fat and pre-teen angst, he had been almost invisible compared to the older jocks and more outgoing students. Yet even then, there was a quiet calm and assurance that spoke of a subtle maturity beyond his years.

As he had passed through the school years, the puppy-fat had given way as he grew up, literally, before my eyes. When he left the school for the local sixth-form at age sixteen, he was well over six feet tall, and as lean as a rake. As far as I knew, he hadn't had a single girlfriend in all that time, although I could see he was extremely interested in girls. They just weren't interested in him – he was a geek as I said – and that wasn't what most teenage girls look for.

As the only female science teacher in the school, I drew some attention from the male members of staff, as well as many of the older boys. I have long hair, and long legs despite my short stature (I'm just 5-foot-4), which is usually more than enough to cause most men to start acting like idiots. However, I knew that too much attention from either male colleagues or from students, much as I might like it personally, wasn't good for my career in the long-term. So to try and discourage the more lascivious looks, I very quickly learned to hide myself under shapeless sweaters and trousers, along with flat shoes. I would tie back my long mousey-blonde hair into a tight bun, usually held in place with a simple wooden barrette, wear the barest minimum of makeup, and just some very simple stud-earrings. It seemed to work for the most-part although really it just wasn't me, or how I would have liked to dress. So to compensate, I would dress to please myself at weekends. The sweaters and slacks would give way to short skirts, sky-high heels, and wonderfully huge over-the-top earrings. Plus I would enjoy experimenting with my hair and makeup much more, trying different looks and styles just to ring the changes and to indulge my imagination and sense of fun. It almost became a double-life: the semi-illicit much more glamorous weekend-me, and the publicly frumpy school-me, and I enjoyed the contrast.

In those final couple of years before Michael left, I could see his admiring glances whenever he saw me, but he did his best to hide it. I was still one of the youngest female teachers in the school, and there were a fair few of the boys who had the usual schoolboy crushes from afar on several of the female staff, you come to expect it, and I actually quite enjoyed the attention. It was flattering to think that I could elicit the attentions of these burgeoning young men many years my junior. Of course fraternisation was completely forbidden, and to be honest, despite the shy, and sometimes not-so-shy, glances of lust that would come my way from many of the boys, I just wasn't interested. I had seen a series of boyfriends come and go in that time, and whilst I enjoyed the attention of the students, I considered them all far too young and immature.

All except Michael. As he grew, his maturity only increased, and I slowly found myself drawn to his quietly assured manner – especially in his last year or so at the school. And then he was gone. He finished his exams in his final year, and left for higher education. I hardly gave him another thought as the school year moved on and we prepared for a new intake of young students. He was just one more student, albeit one of the more appealing ones, who had passed through the system and moved on to continue his education in the local sixth-form college. Michael was certainly smart enough to go on to university, but that was out of my hands now.

* * *

A couple of years passed, and I had hardly given Michael a second thought in all that time. I had broken up with my last boyfriend several months previously, and was enjoying the freedom that I suddenly found myself having. As the school summer break started I had shrugged off the frumpy clothes of school-me and was making the most of the warm weather. So it came as something of a slight shock to the system when I bumped into Michael in the town centre whilst out shopping one day. He smiled warmly as he saw me, and I found myself smiling back.

"Hello Miss," he said walking towards me on the street, "I hardly recognised you at first."

I also hardly recognised him at first. He had really grown up in the past couple of years. Gone was the gangling schoolboy. He had filled out nicely and I could tell immediately that here was the body of a fit youngmanbeneath the casual shirt and tight denim jeans. My stomach did a little involuntary somersault.

Then I blushed slightly as I realised that my short denim skirt that didn't even reach half-way down my thighs, four-inch high stiletto-heeled sandals, large hoop earrings, plus bold smoky eyeliner and mascara was all very different from the prim school-marm that I tried to portray to the staff and students. I attempted to cover up my discomfort with some banalities.

"Oh, hello Michael." I said "Yes, you're right, this is me in my 'civvies'." Then I quickly tried to change the subject, hoping to brush off the obvious difference in my appearance as a mere triviality. "Anyway, how are you doing these days? It must be two years since you left St Anne's?"

"Yes," he replied "just finished my A-levels and hoping my grades will be good enough to get me into my first choice of 'uni in the autumn."

As he spoke, I could see him trying not to keep staring at my eyes, or glancing down at my long legs exposed by the short skirt, and how my high-heels made my legs look. We chatted amiably for a few minutes about his university plans, but all the time I could see he was trying to hide his admiring looks. I suddenly felt both very flattered, and yet also very exposed and quite coy. He had matured since leaving school, there was a quiet assuredness that seemed to make him older and wiser than his years, and as we spoke I felt my initial slight embarrassment lifting. What did it matter if he now saw that I was an attractive woman? We weren't student and teacher any more, and I was allowed to dress how I liked. In fact, I found myself leaning in slightly and altering my posture to try and subtly show off my legs to him. I knew they were my best feature, and I normally liked showing them off whenever I had a chance.

It seemed to work, and he clearly got slightly uncomfortable as a noticeable bulge started to appear in his trousers. My work done, we exchanged a last few banal pleasantries before I made my excuses and headed off. As I walked away, I slyly glanced at his reflection in the shop windows. He was openly watching my bottom as I walked away. The high-heels gave my walk a distinct wiggle that I did my best to emphasise without being too obvious about it. I couldn't help but smile.

It was only later that I wondered at my own behaviour. What had I been thinking, flirting with the innocent lad like that? I was a tease. Yet I had enjoyed the attention, and it had been fun to think of his cock twitching in his trousers and him unable to do anything about it. Just remembering him looking at my legs, my body, gave me a little tingle inside that came as something of a surprise.

* * *

The following week I bumped into Michael again in the town centre as I was having some retail therapy. At first I thought it was coincidence, but I quickly realised that he might very well have been hanging around waiting for me. I was looking in the window of a shoe shop at a pair of beautiful black suede high-heeled strappy sandals, with full five-inch stiletto heels, ankle straps, and a small half-inch platform, when I heard a familiar "Hello Miss" from behind me.

"Hello again." I replied. "You'll have to start calling me by my real name if we're to keep meeting like this." I was shocked at my own brazenness, but was enjoying myself all the same. There was something happening here that I liked, and I didn't want it to end.

"OK Miss... erm..."

"Jenny" I prompted.

"OK, ...Jenny", he said, hesitantly.

"Do you like those?" I asked, nodding towards the shoes.

"Oh yes, I think you'd look fantastic in them." He said, a bit too quickly, and then blushed a deep red as he realised what he'd said.

"Then I'll buy them!" I replied with a giggle, and taking him by the wrist, I dragged him into the shop. I quickly found the shoes I'd been looking at, and asked the assistant for my size. Michael was looking particularly nervous, and hardly knew where to put his eyes as I slipped off the comfortable old four-inch high cork-heeled wedge sandals I had been wearing so I could try on the new shoes. Bending low on the little bench to do up the ankle straps I could see in the mirror that Michael was looking down my blouse at my breasts in my small white lacy bra. I took my time, letting him have an eyeful. My breasts aren't very large, I'm a 34B for those of you gentle readers who are interested in numbers, but I'm proud that they are still firm, with pert nipples that can really stand out when I'm aroused. Under Michael's shy gaze I could feel my nipples hardening. I knew I was teasing him, and I really wasn't at all sure exactly why I was doing it, but it was fun, and also quite flattering, to see the affect I was having on him - and him-on-me come to that. All I knew was that I was actually enjoying having him admire my body.

Standing up, I paraded back and forth in front of him in the new shoes, twirling round at the end of each length of the aisle making my short, light-cotton, summery A-line skirt flare up around my thighs. I didn't often wear such high heels, but I knew how to walk in them, and even higher when I wanted, and I especially enjoyed the feelings of power and sexuality that all high-heels gave me. The higher the better! Michael was so funny that I had to physically stifle my giggles. He had gone almost beetroot red, and had a very noticeable bugle in his trousers.

"So, do you like them on me?" I asked, as if it was the most natural thing in the world.

"Y, y, yes..." He stammered, hardly able to talk. "You look wonderful."

"Thank you." I said with a genuine smile, and I sat down again to take off the shoes, making sure Michael got a good view of my legs as I did so. "I like them too, so I'll definitely take them then." and handing the shoes to the shop assistant who hovered near-by, I headed for the check-out.

"That was fun." I said as we left the left the shop a few minutes later. "Let's go get a coffee to celebrate my new shoes?"

He hardly had much choice, and trailed after me like a little lost puppy before I grabbed his arm and made him walk next to me, threading my arm through his elbow. A little later, sitting in the Costa store, he seemed to start to relax as he realised that I wasn't going to bite. He even managed to remember to stop calling me "Miss" after a few false starts, and we talked happily about the world in general for nearly an hour. I very gently pumped him for information. Despite a few slight blushes of embarrassment, he eventually admitted that he had never had a "proper girlfriend" as he put it, although he had had several crushes from afar. His few faltering advances had always been spurned by the girls at school, and none of his affections had been returned. So for now he had thrown himself back into his studies, and had given up on the idea of a girlfriend for the time being. I also found out what he likes in a girl, and discovered that he was a very visual person – liking all the classic clichés: short skirts, high heels, lingerie, stockings, and suspenders. Plus he liked girls in heavier makeup, which was slightly unusual, but since I enjoyed experimenting with makeup, I thought that could be fun. In fact it explained why he kept looking at my eyes as if he were studying them – he was admiring my makeup! As I liked experimenting with cosmetics when I was out of school, I thought I could use this fact to my advantage, and have some fun myself at the same time. I suddenly felt that I wanted to look good for him, as well as for myself.

Knowing he was still a virgin gave me a little thrill, and as we talked, I could feel myself being drawn to him. He was mature and sensible, more so than several boyfriends I'd had who were almost twice his age, and his innocence was quite appealing in a strange way. When the time came for him to leave, I had already made up my mind about what I wanted to have happen. Now I just had to figure out how I was going to make it happen.

"Michael, I was wondering if you could help me out with something?" I asked as he was getting ready to leave.

"Of course I'll help if I can," he replied, "but what could you possibly want my help for?" I could see he was curious, and I got the distinct impression that he was looking for an excuse to see me again too. At least, that's what I hoped.

"My car has just gone into the garage for some repairs for a couple of days, and so I was wondering if you could drive me? You do have your licence don't you?" It was pretty feeble I knew, but it was also sort-of true. My car actually did have to go into the garage, but I would normally take any of the various forms of public transport quite happily for the few days it wasn't available to me. Plus I didn't really have anywhere specific I needed to go.

"Oh yes, I passed my test well over a year ago." Michael said with a smile. Either he didn't see how weak my excuse was, or he chose to deliberately ignore it. "I've only got a banger of a car though. I can't afford better but it gets me around, so are you sure it'll be OK?"

"So long as it goes, and is reasonably reliable, then I'm sure it will be fine." I assured him, and thinking fast I quickly came up with an idea. "Are you free tomorrow? I was thinking about going into London for some special shopping if that's OK with you? I'll pay you for your petrol of course! Then you can do what you like in town whilst I do my shopping. I'm sure you don't want to follow me through girly-clothes stores and shoe-shops all day."

The smile on his face was wide and warm. London was over an hour-and-a-half's drive from here, so we would have at least three hours together in the car, there and back.

"That's fine." He said. "I can visit my favourite Science Fiction bookshop, and meet you back at the car at a pre-arranged time?" I could see he was happy to have an excuse to do something he enjoyed, and I was relieved to see that he wasn't embarrassed to admit his geeky hobby to me. I knew exactly which bookshop he was referring to, an ex-boyfriend had dragged me there many years ago, and I'd found it surprisingly interesting – much to his disappointment. I think he'd wanted to keep it as "his thing", although his interests were different to mine. I'd found I preferred classic old science fiction novels rather than the recent TV and movie memorabilia he had been into, which bored me to tears. But for tomorrow I had a plan slowly formulating in my mind. I was happy for Michael to do whatever he wanted in London. What I wanted was to visit some specialist shops I knew of – I was going to give Michael a real visual treat in the near future!

"Do you mean 'Forbidden Planet'?" I asked, getting back to his favourite hobby.

"You... You know it?" He was clearly stunned that I'd even heard of the famous bookshop.

"Oh yes, I quite like some science fiction," I admitted, and Michael beamed like a Cheshire cat. "I am a scientist after all. Anyway, how about you pick me up just after nine a.m. tomorrow?" Then he took my address and we swapped mobile phone numbers.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
5 Comments
The MouseThe Mouseover 10 years ago
Makes a nice change ...

… to have a believable, slow build-up to a story. Of the stories I've read - or tried to - lately, many have been far too much the "wham bam, thank you ma'am" type. Looking forward to many more chapters from you.

mammoetmammoetover 10 years ago
great read

keep going, nice story, hope to read chapter 2 soon.

mdwdirectmdwdirectover 10 years ago
Looking forward to the next chapter

Very good story so far!

Zach_lost_in_AusZach_lost_in_Ausover 10 years ago
More...

...please! Got my attention and left me wanting the story to continue.

lesliejoneslesliejonesover 10 years ago
Good pacing

I enjoyed this story segment. It's an excellent starting chapter. You've developed the narrator as an interesting vibrant character and I liked how you took your time getting this going. I look forward to more.

Share this Story

READ MORE OF THIS SERIES

Toy Boy Series Info

Similar Stories

Moms at the Beach Ch. 01 Newly single Moms make tempting targets for enamored sons.in Mature
Party with the Neighbor MILFs A teen joins his four mature women neighbors.in Mature
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
Mrs. Young Ch. 01 My best friend's mom takes care of my morning wood.in Mature
Milf Tails: After Midnight Steven has a late night encounter with his best friend's mom.in Mature
More Stories